WO2023054344A1 - Composé, matériau de transport de trous et élément de conversion photoélectrique l'utilisant - Google Patents

Composé, matériau de transport de trous et élément de conversion photoélectrique l'utilisant Download PDF

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WO2023054344A1
WO2023054344A1 PCT/JP2022/035899 JP2022035899W WO2023054344A1 WO 2023054344 A1 WO2023054344 A1 WO 2023054344A1 JP 2022035899 W JP2022035899 W JP 2022035899W WO 2023054344 A1 WO2023054344 A1 WO 2023054344A1
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group
carbon atoms
photoelectric conversion
linear
substituent
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友也 大倉
俊昭 伊東
秀聡 高橋
洋 佐藤
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保土谷化学工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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

Definitions

  • the present invention relates to a compound, a hole transport material, and a photoelectric conversion device using the same.
  • Patent Document 1 Non-Patent Documents 1-2).
  • Perovskite solar cells often use a hole-transporting material in the element.
  • the purpose of use is to (1) improve the photoelectric conversion efficiency by enhancing the function of selectively transporting holes, and (2) bond with the perovskite photoelectric conversion layer to create a perovskite material that is susceptible to moisture and oxygen.
  • Protect for example, Non-Patent Document 3
  • Spiro-OMeTAD a spirobifluorene-based organic compound
  • is often used as a standard hole-transporting material but the use of acridone- and thioxanthone-based organic compounds has also been proposed (eg, Non-Patent Document 4).
  • the problem to be solved by the present invention is a compound useful as a hole-transporting material for a photoelectric conversion device capable of efficiently extracting current, and a hole-transporting layer containing the compound that has good photoelectric conversion characteristics.
  • An object of the present invention is to provide a suitable photoelectric conversion element and solar cell.
  • the inventors have made extensive studies on improving photoelectric conversion characteristics. As a result, the inventors designed and developed a compound having a specific structure, and used it as a hole transport layer in a photoelectric conversion device to achieve high photoelectric conversion efficiency. and a highly durable photoelectric conversion device and perovskite solar cell. That is, the gist of the present invention is as follows.
  • R 1 to R 20 each independently represent a hydrogen atom, a halogen atom, a carboxyl group, a trimethylsilyl group, or an optionally substituted linear or branched chain having 1 to 20 carbon atoms.
  • X 1 and X 2 represent divalent groups and may be the same or different.
  • Y represents an oxygen atom, a sulfur atom or CR21R22 ;
  • R 21 and R 22 are each independently an optionally substituted linear or branched acyl group having 1 to 10 carbon atoms, or an optionally substituted carbon atom It represents a linear or branched alkoxycarbonyl group of number 1 to 10, which may be bonded together to form a ring.
  • R 23 is a hydrogen atom, an optionally substituted linear or branched C 1-20 alkyl group, an optionally substituted C 2-20 linear It represents a chain or branched alkenyl group, or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms.
  • R 24 to R 29 each independently have a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 10 carbon atoms, or a substituent.
  • a linear or branched alkenyl group having 2 to 10 carbon atoms which may be optionally substituted a cycloalkyl group having 3 to 10 carbon atoms which may have a substituent
  • a carbon which may have a substituent represents an aromatic hydrocarbon group having 6 to 18 atoms, or a heterocyclic group having 5 to 18 ring forming atoms which may have a substituent
  • R 24 and R 25 , R 26 and R 27 , and R 28 and R 29 may combine with each other to form a ring.
  • Z represents an oxygen atom, a sulfur atom or a selenium atom.
  • m and n each independently represent an integer of 0 to 2; However, both m and n cannot be 0.
  • R 1 to R 20 each have a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituent. an alkoxy group of 1 to 20 carbon atoms which may be substituted, a thio group of 1 to 18 carbon atoms which may be substituted, an amino group of 1 to 20 carbon atoms which may be substituted A compound that is
  • a hole transport material comprising the above compound.
  • a photoelectric conversion element and a perovskite solar cell having good photoelectric conversion efficiency and high durability can be obtained.
  • the compound of the present invention can be used as a hole-transporting material, and is suitable for photoelectric conversion devices and perovskite solar cells.
  • the photoelectric conversion device of the present invention typically comprises a conductive support 1, an electron transport layer 2, a photoelectric conversion layer 3, a hole transport layer 4, and a counter electrode 5, as shown in the schematic cross-sectional view of FIG. have.
  • the compound represented by the general formula (1) which is the hole-transporting material of the present invention, will be specifically described below, but the present invention is not limited thereto.
  • each of R 1 to R 20 is independently a hydrogen atom, a halogen atom, a carboxyl group, a trimethylsilyl group, a linear chain having 1 to 20 carbon atoms which may be substituted, or Branched alkyl group, optionally substituted linear or branched C 2-20 alkenyl group, optionally substituted C 3-10 cycloalkyl a linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent, a cycloalkoxy group having 3 to 10 carbon atoms which may have a substituent, a substituent A linear or branched acyl group having 1 to 20 carbon atoms which may have a thio group having 1 to 18 carbon atoms which may have a substituent an amino group having 1 to 20 carbon atoms which may be substituted, an aromatic hydrocarbon group having 6 to 36 carbon atoms which may be substituted, or a heterocyclic group having 5 to 36 ring atoms which may have
  • the “halogen atom” represented by R 1 to R 20 includes fluorine, chlorine, bromine and iodine.
  • the "linear or branched alkyl group optionally having 1 to 20 carbon atoms" represented by R 1 to R 20 20 linear or branched alkyl groups” specifically include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, Examples include n-pentyl group, isopentyl group, n-hexyl group, 2-ethylhexyl group, heptyl group, octyl group, isooctyl group, nonyl group and decyl group.
  • linear or branched alkenyl group optionally having 2 to 20 carbon atoms represented by R 1 to R 20
  • the linear or branched alkenyl group of 20 specifically includes ethenyl group (vinyl group), 1-propenyl group, 2-propenyl group (allyl group), 1-methylethenyl group, 1-butenyl group, 2 -butenyl group, 1-pentenyl group, 1-hexenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, or two or more of these alkenyl groups having 2 carbon atoms
  • a linear or branched alkenyl group of up to 20 can be mentioned.
  • the "cycloalkyl group having 3 to 10 carbon atoms" in the “cycloalkyl group having 3 to 10 carbon atoms which may have a substituent" represented by R 1 to R 20 Specific examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group and the like. can be done.
  • the "linear or branched alkoxy group having 1 to 20 carbon atoms optionally having a substituent" represented by R 1 to R 20 20 linear or branched alkoxy group” specifically includes methoxy group, ethoxy group, propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, heptyloxy group, octyl oxy group, nonyloxy group, decyloxy group, isopropoxy group, isobutoxy group, s-butoxy group, t-butoxy group, isooctyloxy group, t-octyloxy group, phenoxy group, tolyloxy group, biphenylyloxy group, terfenyloxy group Ryloxy group, naphthyloxy group, anthryloxy group, phenanthryloxy group, fluorenyloxy group, indenyloxy group and the like can be mentioned.
  • branched cycloalkoxy group having 3 to 10 carbon atoms
  • the branched cycloalkoxy group include a cyclopropoxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a 4-methylcyclohexyloxy group, and the like.
  • the "linear or branched acyl group optionally having 1 to 20 carbon atoms" represented by R 1 to R 20 20 linear or branched acyl group” specifically includes an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a benzoylacetyl group, a benzoyl group, and the like.
  • it contains an alkyl chain it includes those in which hydrogen atoms are completely substituted with fluorine atoms (perfluorination). Further, it may be one (--CO--N ⁇ ) bonded to an amino group.
  • the "thio group having 1 to 18 carbon atoms" in the "optionally substituted thio group having 1 to 18 carbon atoms" represented by R 1 to R 20 includes: Specific examples include a methylthio group, an ethylthio group, a propylthio group, a phenylthio group and a biphenylthio group.
  • the “amino group having 1 to 20 carbon atoms” in the “amino group having 1 to 20 carbon atoms which may have a substituent” represented by R 1 to R 20 includes: Specific examples of monosubstituted amino groups include ethylamino group, acetylamino group and phenylamino group, and disubstituted amino groups include diethylamino group, diphenylamino group and acetylphenylamino group.
  • hydrocarbon group include phenyl group, biphenyl group, terphenyl group, naphthyl group, biphenyl group, anthracenyl group (anthryl group), phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluorane Examples include a thenyl group and a triphenylenyl group.
  • the aromatic hydrocarbon group includes a "condensed polycyclic aromatic group".
  • the "heterocyclic group having 5 to 36 ring-forming atoms which may be substituted" represented by R 1 to R 20 "group” specifically includes a pyridyl group, a pyrimidylinyl group, a triazinyl group, a thienyl group, a furyl group (furanyl group), a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a quinolyl group, an isoquinolyl group, a napthyldinyl group, and an acridinyl group.
  • phenanthrolinyl group benzofuranyl group, benzothienyl group, oxazolyl group, indolyl group, carbazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzo A thienyl group, a carbonylyl group, and the like can be mentioned.
  • R 1 to R 20 a linear or branched alkyl group having 1 to 18 carbon atoms optionally having a substituent", “having a substituent A linear or branched alkenyl group having 2 to 20 carbon atoms which may be substituted", "a cycloalkyl group having 3 to 10 carbon atoms which may have A linear or branched alkoxy group having 1 to 20 carbon atoms which may be A linear or branched acyl group having 1 to 20 carbon atoms which may be an amino group having 1 to 20 carbon atoms which may be substituted", “an aromatic hydrocarbon group having 6 to 36 carbon atoms which may be substituted", or "5 to 5 ring atoms which may be substituted"
  • the "substituent" in the "heterocyclic group of 36” specifically includes halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a cyano group;
  • R 1 to R 20 each have a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituent.
  • a linear or branched alkoxy group having 1 to 20 carbon atoms which may be substituted, a thio group having 1 to 18 carbon atoms which may have a substituent, or a carbon atom which may have a substituent It is preferably an amino group having a number of 1 to 20, a hydrogen atom, a linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent, even if it has a substituent It is more preferably a thio group having 1 to 18 carbon atoms, or an amino group having 1 to 20 carbon atoms which may have a substituent, a hydrogen atom, or a straight chain having 1 to 20 carbon atoms.
  • R 1 to R 5 , R 6 to R 10 , R 11 to R 15 , and R 16 to R 20 are adjacent groups via a single bond, an oxygen atom, a sulfur atom, or a selenium atom. or a bond through a nitrogen atom to form a ring
  • R 5 and R 6 and R 15 and R 16 are They may be joined together to form a ring by a bond or a bond through a nitrogen atom.
  • R 5 and R 6 and R 15 and R 16 form a ring, they are preferably bonded to each other via a single bond, an oxygen atom, or a sulfur atom to form a ring. are more preferably bonded to each other to form a carbazole ring.
  • R 1 to R 4 , R 7 to R 10 , R 11 to R 14 and R 17 to R 20 are hydrogen atoms or carbon atoms
  • a diphenylamino group having a linear or branched alkoxy group having 1 to 20 atoms as a substituent is preferred.
  • Y represents an oxygen atom, a sulfur atom or CR 21 R 22 , and R 21 and R 22 each independently represents a nitrile group and the number of carbon atoms which may have a substituent. It represents an acyl group of 1 to 10 or an alkoxycarbonyl group of 1 to 10 carbon atoms which may have a substituent. Y is preferably electron-withdrawing and is preferably an oxygen atom.
  • the “linear or branched acyl group having 1 to 10 carbon atoms optionally having a substituent” represented by R 21 and R 22 10 linear or branched acyl group” includes “optionally substituted C 1 to C 20 acyl groups represented by R 1 to R 20 in general formula (1) , the same ones as ⁇ an optionally substituted linear or branched acyl group having 1 to 10 carbon atoms'' can be mentioned.
  • the "linear or branched alkoxycarbonyl group having 1 to 10 carbon atoms” represented by R 21 and R 22 the "linear or branched The alkoxycarbonyl group of” specifically includes a methoxycarbonyl group, an ethoxycarbonyl group, etc., and when an alkyl chain is included, hydrogen atoms are completely substituted with fluorine atoms (perfluorinated). including.
  • R 21 and R 22 may be bonded to each other via a single bond, an oxygen atom, a sulfur atom, a selenium atom or a nitrogen atom to form a ring.
  • an acidic heterocyclic ring such as a barbituric acid type, a thiobarbituric acid type, or an indanedione type.
  • R 23 is a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, an optionally substituted carbon It represents a linear or branched alkenyl group having 2 to 20 atoms, or a cycloalkyl group having 3 to 10 carbon atoms which may have a substituent.
  • R 23 is preferably an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, and a linear or branched alkyl group having 1 to 10 carbon atoms. more preferably a group.
  • the “linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent” represented by R 23 The “chain or branched alkyl group” includes “linear or branched alkyl group optionally having a substituent and having 1 to 20 carbon atoms represented by R 1 to R 20 in the general formula (1). and the same as the "alkyl group having a shape" can be mentioned.
  • the “linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent” represented by R 23 The “chain or branched alkenyl group” includes “linear or branched alkenyl groups optionally having substituent(s) of 2 to 20 carbon atoms represented by R 1 to R 20 in the general formula (1). and the same as the "alkenyl group in the form of a
  • the "cycloalkyl group having 3 to 10 carbon atoms" in the "cycloalkyl group having 3 to 10 carbon atoms which may have a substituent" represented by R 23 includes:
  • the same as the “optionally substituted cycloalkyl group having 3 to 10 carbon atoms” represented by R 1 to R 20 can be mentioned.
  • X 1 and X 2 are preferably divalent groups represented by general formula (2).
  • R 24 to R 29 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, a substituent A linear or branched alkenyl group having 2 to 10 carbon atoms which may have a cycloalkyl group having 3 to 10 carbon atoms which may have a substituent, a substituent represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be optionally substituted, or a heterocyclic group having 5 to 18 ring atoms which may have a substituent.
  • R 24 to R 29 are preferably hydrogen atoms.
  • the linear or branched alkyl group of 10 includes “linear groups having 1 to 20 optionally substituted carbon atoms represented by R 1 to R 20 in the general formula (1).
  • the same ones as the “linear or branched alkyl group having 1 to 10 carbon atoms” can be mentioned.
  • the linear or branched alkenyl group of 10" is represented by R 1 to R 20 in the general formula (1), and the “linear group optionally having a substituent and having 2 to 20 carbon atoms Among the “linear or branched alkenyl groups", the same ones as the “linear or branched alkenyl groups having 2 to 10 carbon atoms" can be mentioned.
  • the “cycloalkyl group having 3 to 10 carbon atoms” in the “cycloalkyl group having 3 to 10 carbon atoms which may have a substituent” represented by R 24 to R 29 examples thereof include the same as the “optionally substituted cycloalkyl group having 3 to 10 carbon atoms” represented by R 1 to R 20 in general formula (1).
  • the “ hydrocarbon group” includes “ carbon The same groups as those described in "aromatic hydrocarbon group having 6 to 18 atoms" can be mentioned.
  • R 24 and R 25 , R 26 and R 27 and R 28 and R 29 are bonded to each other via a single bond, an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom. and may form a ring.
  • Z represents an oxygen atom, a sulfur atom or a selenium atom, and Z is preferably a sulfur atom.
  • m and n each represent an integer of 0 to 2, and when m is 0, n is 1 or 2, and when n is 0, m is 1 or 2. That is, there is no case where either one of m and n is 1 or more and both are 0. m is preferably 1 and n is preferably 0 or 1. Further, the acridone derivative portion (including the case where Y is CR 21 R 22 ) which is the central skeleton of general formula (1) and the group represented by general formula (2) are a phenyl group and a 5-membered ring It may be bonded to either heterocyclic group.
  • m is 1 and n is 0 or 1.
  • n is 1, the acridone derivative moiety, which is the central skeleton of general formula (1), and a 5-membered heterocyclic group are bonded. is preferred.
  • the hole-transporting material of the present invention represented by the general formula (1) can be synthesized by a known method.
  • Examples of the method for purifying the compound represented by the general formula (1) of the present invention include purification by column chromatography, purification by adsorption using silica gel, activated carbon, activated clay, etc., and recrystallization or crystallization with a solvent. It is effective to use these methods in combination to increase the purity of the compound represented by the general formula (1). Also, identification of these compounds can be performed by nuclear magnetic resonance spectroscopy (NMR).
  • NMR nuclear magnetic resonance spectroscopy
  • the photoelectric conversion device of the present invention preferably comprises a conductive support 1, an electron transport layer 2, a photoelectric conversion layer 3, a hole transport layer 4, and a counter electrode 5, as shown in FIG. not something.
  • the photoelectric conversion device of the present invention is preferably used as a solar cell, more preferably a perovskite photoelectric conversion device, but is not limited to this.
  • a perovskite-type photoelectric conversion element may comprise a conductive support (electrode) 1, an electron transport layer 2, a photoelectric conversion layer (perovskite layer) 3, a hole transport layer 4, and a counter electrode 5 in this order.
  • it may be composed in the order of a conductive support, a hole transport layer, a photoelectric conversion layer (perovskite layer), an electron transport layer, and a counter electrode.
  • the conductive support 1 shown in FIG. 1 must have translucency capable of transmitting light that contributes to photoelectric conversion. Further, the conductive support is preferably a conductive substrate because it is a member having a function of extracting current from the photoelectric conversion layer.
  • conductive materials include tin-doped indium oxide (ITO), zinc-doped indium oxide (IZO), tungsten-doped indium oxide (IWO), zinc aluminum oxide (AZO), fluorine Conductive transparent oxide semiconductors such as doped tin oxide (FTO), indium oxide (In 2 O 3 ), and indium-tin composite oxide can be mentioned, but tin-doped indium oxide (ITO) and fluorine-doped oxide It is preferable to use tin (FTO) or the like.
  • the electron transport layer 2 shown in FIG. Although it is preferable that the electron transport layer 2 is formed on the substrate, it is not particularly limited.
  • the electron transport layer is used to improve the efficiency of electron transfer from the photoelectric conversion layer to the electrode and to block the transfer of holes.
  • the semiconductor forming the electron transport layer examples include tin oxide (SnO, SnO 2 , SnO 3 etc.), titanium oxide (TiO 2 etc.), tungsten oxide (WO 2 , WO 3 , W 2 O 3, etc.), zinc oxide (ZnO), niobium oxide ( Nb2O5 , etc.), tantalum oxide ( Ta2O5, etc.), yttrium oxide ( Y2O3 , etc. ), strontium titanate (SrTiO3 , etc.), etc.
  • Metal oxides metal sulfides such as titanium sulfide, zinc sulfide, zirconium sulfide, copper sulfide, tin sulfide, indium sulfide, tungsten sulfide, cadmium sulfide, silver sulfide; titanium selenide, zirconium selenide, indium selenide, selenide Metal selenides such as tungsten; elemental semiconductors such as silicon and germanium; In the present invention, it is preferable to use one or more selected from tin oxide, titanium oxide, and zinc oxide as the semiconductor.
  • a commercially available paste containing the semiconductor fine particles may be used, or a paste (electron transport layer coating liquid) prepared by dispersing commercially available semiconductor fine powder in a solvent may be used.
  • the solvent used in preparing the paste include water; alcohol solvents such as methanol, ethanol and isopropyl alcohol; ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; n-hexane, cyclohexane, benzene, Examples include, but are not limited to, hydrocarbon solvents such as toluene. Also, these solvents can be used singly or as a mixed solvent of two or more.
  • the powder may be ground in a mortar or the like.
  • a surfactant or the like to prevent the semiconductor fine particles from aggregating, and to increase the viscosity, it is preferable to add a thickener such as polyethylene glycol.
  • the electron transport layer can be obtained using a known film forming method depending on the material to be formed.
  • a method for forming the electron transport layer any coating method using a coating liquid can be used. Spin coating method, inkjet method, doctor blade method, drop casting method, squeegee method, screen printing method, reverse roll coating method, gravure coating method, kiss coating method, roll brush method, spray coating method, air knife coating method, wire barber coating method , a method of coating a conductive substrate by a wet coating method such as a pipe doctor method, an impregnation/coating method, or a curtain coating method, and then baking to remove solvents and additives to form a film, a sputtering method, a vapor deposition method, Examples include, but are not limited to, electrodeposition, electrodeposition, microwave irradiation, and the like.
  • the present invention it is preferable to form a film by a spin coating method using the electron transport layer coating liquid prepared by the above method, but the method is not limited to this.
  • the conditions for spin coating can be set as appropriate.
  • the atmosphere in which the film is formed is not particularly limited, and the atmosphere may be used.
  • the thickness of the electron transport layer is preferably from 5 nm to 100 nm, and preferably from 10 nm to 50 nm, when a dense electron transport layer is used. It is more preferable to have In the present invention, when a porous (mesoporous) metal oxide is used in addition to the dense layer, the film thickness is usually preferably 20 to 200 nm or less, more preferably 50 to 150 nm. preferable.
  • a photoelectric conversion layer (perovskite layer) 3 is preferably formed on the electron transport layer 2 shown in FIG.
  • the perovskite material that is the photoelectric conversion layer represents a series of materials having a structure represented by the general formula ABX3 .
  • any coating method can be used, and the same method as the method for forming the electron transport layer can be used. .
  • the perovskite precursor a commercially available material may be used, and in the present invention, it is preferable to use a precursor composed of lead halide, methylammonium halide, formamidine halide, and cesium halide with an arbitrary composition. , but not limited to.
  • the solvent for the perovskite precursor solution of the present invention includes, but is not limited to, N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), ⁇ -butyrolactone, etc., from the viewpoint of solubility of the precursor. These solvents may be used singly or in combination of two or more, and it is preferable to use a mixed solution of N,N-dimethylformamide and dimethylsulfoxide.
  • DMF N,N-dimethylformamide
  • DMSO dimethylsulfoxide
  • ⁇ -butyrolactone ⁇ -butyrolactone
  • the atmosphere during film formation of the photoelectric conversion layer is preferably a dry atmosphere from the viewpoint of preventing the contamination of moisture to produce highly efficient perovskite solar cells with good reproducibility.
  • a dry inert gas atmosphere is more preferred.
  • the temperature for heating the photoelectric conversion layer (perovskite layer) with a hot plate or the like is preferably 50 to 200°C, more preferably 70 to 150°C, from the viewpoint of generating perovskite material from the precursor.
  • the heating time is preferably about 10 to 90 minutes, more preferably about 10 to 60 minutes.
  • the film thickness of the photoelectric conversion layer (perovskite layer) of the present invention is determined from the viewpoint of further suppressing performance deterioration due to defects and peeling, and from the viewpoint that the photoelectric conversion layer has a sufficient light absorption rate and the device resistance does not become too high. 50 to 1000 nm, more preferably 300 to 700 nm, in order to
  • the hole transport layer 4 shown in FIG. 1 is a layer having a function of transporting holes, and is a layer located between the photoelectric conversion layer (perovskite layer) 3 and the counter electrode 5. be.
  • the hole transport layer is used to improve the efficiency of hole transfer from the photoelectric conversion layer to the electrode and to block the transfer of electrons.
  • the hole transport layer can use, for example, a conductor, a semiconductor, an organic hole transport material, or the like, and may contain an additive for the purpose of further improving the hole transport properties.
  • the hole-transporting layer in the photoelectric conversion element of the present invention is a layer containing the compound represented by the general formula (1) as a hole-transporting material.
  • the hole-transporting material two or more of the compounds represented by the general formula (1) may be used in combination, or may be used in combination with other hole-transporting materials that do not belong to the present invention.
  • compound semiconductors containing monovalent copper such as CuI, CuInSe 2 and CuS
  • GaP GaP
  • NiO, CoO, FeO and Bi 2 Compounds containing metals other than copper, such as O 3 , MoO 2 , Cr 2 O 3 , etc., may be mentioned, and these metal oxides may be mixed in the hole-transporting layer and laminated on the hole-transporting material.
  • organic hole transport materials include polythiophene derivatives such as poly-3-hexylthiophene (P3HT) and polyethylenedioxythiophene (PEDOT); fluorene derivatives such as di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD); carbazole derivatives such as polyvinylcarbazole; poly[bis(4-phenyl)(2,4,6-trimethyl) phenyl)amine] (PTAA); diphenylamine derivatives; polysilane derivatives; and polyaniline derivatives.
  • polythiophene derivatives such as poly-3-hexylthiophene (P3HT) and polyethylenedioxythiophene (PEDOT); fluorene derivatives such as di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD); carbazole derivatives such as polyvinylcarbazole; poly[
  • Any coating method can be used as a method for coating the hole transport layer of the photoelectric conversion element of the present invention using a coating liquid, and the same method as the method for forming the electron transport layer can be used.
  • solvents used in the hole transport layer coating solution during film formation include benzene, toluene, xylene, mesitylene, tetralin (1,2,3,4-tetrahydronaphthalene), and monochlorobenzene (chlorobenzene).
  • o-dichlorobenzene m-dichlorobenzene, p-dichlorobenzene, nitrobenzene
  • aromatic organic solvents such as dichloromethane, chloroform, 1,2-dichloroethane, 1,1,2-trichloroethane, alkyl halides such as dichloromethane Organic solvent
  • Nitrile solvents such as benzonitrile and acetonitrile
  • Ether solvents such as tetrahydrofuran, dioxane, diisopropyl ether, c-pentyl methyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol monomethyl ether
  • Ethyl acetate, propylene glycol Ester solvents such as monomethyl ether acetate
  • the film thickness of the hole transport layer is preferably 5 to 500 nm, more preferably 10 nm to 250 nm, from the viewpoint of further improving the photoelectric conversion efficiency.
  • the atmosphere during film formation of the hole transport layer is preferably a dry atmosphere from the viewpoint of preventing the contamination of moisture to produce highly efficient perovskite solar cells with good reproducibility. Moreover, it is preferable to use a dehydrated solvent having a water content of 10 ppm or less.
  • the hole transport layer may contain a dopant (or an oxidizing agent) or a basic compound (or a basic additive) as additives. Adding an additive to the hole transport layer to improve the carrier concentration of the hole transport material in the hole transport layer (doping) leads to an improvement in the photoelectric conversion efficiency of the photoelectric conversion device.
  • the amount of the additive is preferably 3.5 equivalents or less with respect to 1 equivalent of the hole-transporting material.
  • the hole transport layer contains a dopant
  • specific examples of the dopant include lithium bis(trifluoromethylsulfonyl)imide (LiTFSI), bis(trifluoromethanesulfonyl)imide silver, tris(2-(1H-pyrazole-1 -yl)-4-tert-butylpyridine)cobalt(III) tri[bis(trifluoromethane)sulfonimide] (FK209), NOSbF 6 , SbCl 5 , SbF 5 and the like.
  • LiTFSI lithium bis(trifluoromethylsulfonyl)imide
  • LiTFSI lithium bis(trifluoromethylsulfonyl)imide
  • a dopant when used, it is preferably 2.0 equivalents or less, more preferably 0.5 equivalents or less, relative to 1 equivalent of the hole transport material. Containing a dopant, which is an additive, in the hole transport layer leads to an improvement in the photoelectric conversion efficiency of the photoelectric conversion element, but lowers the durability of the photoelectric conversion element using an organic compound and shortens the life of the entire element. There is a concern that it will be lost (for example, Non-Patent Document 3). Therefore, development of a photoelectric conversion element having a hole transport layer with a reduced dopant content is desired. Moreover, if the content can be reduced, it is possible to reduce the additive cost and the manufacturing process cost.
  • the hole transport layer may contain a basic compound (basic additive) as an additive.
  • basic compounds include 4-tert-butylpyridine (tBP), 2-picoline, 2,6-lutidine and the like.
  • tBP 4-tert-butylpyridine
  • 2-picoline 2-picoline
  • 2,6-lutidine 2,6-lutidine
  • a basic compound is often used in combination with a dopant.
  • a dopant it is desirable to use it in combination, and it is preferable to use tert-butylpyridine.
  • a basic compound when used, it is preferably 5 equivalents or less, more preferably 3 equivalents or less, relative to 1 equivalent of the hole transport material.
  • the counter electrode 5 shown in FIG. 1 is arranged opposite to the conductive support 1 and formed on the hole transport layer 4 so that charges can be exchanged with the hole transport layer.
  • a metal electrode as a counter electrode on the hole transport layer 4.
  • An electron blocking layer made of an organic material or an inorganic compound semiconductor is provided between the hole transport layer 4 and the counter electrode 5. can also be added.
  • specific materials used for the counter electrode include metals such as platinum, titanium, stainless steel, aluminum, gold, silver, nickel, magnesium, chromium, cobalt, copper, and alloys thereof.
  • metals such as platinum, titanium, stainless steel, aluminum, gold, silver, nickel, magnesium, chromium, cobalt, copper, and alloys thereof.
  • gold, silver, or a silver alloy because it exhibits high electrical conductivity even in a thin film.
  • silver and gold alloys, silver and copper alloys, silver and palladium alloys, silver and copper alloys, and silver and copper alloys are selected in order to improve the stability of thin films that are less susceptible to sulfidation or chlorination. Examples include palladium alloys and silver-platinum alloys.
  • a material that can form a counter electrode by a method such as vapor deposition is preferred.
  • its film thickness is preferably 10 nm or more, more preferably 50 nm or more, in order to obtain good conductivity.
  • the conductive support becomes the cathode and the counter electrode becomes the anode.
  • Light such as sunlight is preferably applied from the conductive support side.
  • the photoelectric conversion layer perovskite layer
  • the photoelectric conversion layer absorbs light and enters an excited state, generating electrons and holes.
  • the electrons move through the electron-transporting layer and the holes move through the hole-transporting layer to the electrode, thereby causing a current to flow and functioning as a photoelectric conversion element.
  • short-circuit current density represents the current per 1 cm 2 that flows between both terminals when the output terminals are short-circuited
  • the open-circuit voltage represents the voltage between the two terminals when the output terminals are open-circuited
  • the fill factor is the maximum output (product of current and voltage) divided by the product of short-circuit current density and open-circuit voltage, and is mainly affected by internal resistance.
  • the photoelectric conversion efficiency is obtained as a value obtained by dividing the maximum output (W) by the light intensity (W) per 1 cm 2 and multiplying the value by 100, expressed as a percentage.
  • the photoelectric conversion device of the present invention can be applied to perovskite solar cells, various optical sensors, and the like.
  • a photoelectric conversion element containing, as a hole transport layer, a hole transport material containing the compound represented by the general formula (1) serves as a cell, and the required number of cells are arranged to form a module. It can be obtained by arranging and providing predetermined electric wiring.
  • a compound of the following formula (12) (0.10 g), a compound of the following formula (13) (0.34 g), an aqueous potassium carbonate solution (0.42 g, manufactured by Kanto Kagaku Co., Ltd.), toluene (10 mL), ethanol (10 mL) were placed in a reaction vessel. 2.5 mL) and water (2.5 mL) were added, and the mixture was degassed and replaced with argon. Tetrakistriphenylphosphine palladium (0.01 g, manufactured by Kanto Kagaku Co., Ltd.) was added to the reaction solution, degassed again, and heated under reflux for 7 hours in an argon atmosphere.
  • Example 1 Preparation of photoelectric conversion element and evaluation of photoelectric conversion characteristics
  • An ITO film-coated glass conductive support 1, Geomatec's FLAT ITO film-coated glass
  • a tin oxide layer (electron transport layer 2) having a thickness of about 20 nm was formed by heating at 150° C. for 30 minutes on a hot plate.
  • Formamidine hydroiodide (1M, manufactured by Tokyo Kasei Co., Ltd.), lead iodide (II) (1.1M, manufactured by Tokyo Kasei Co., Ltd.), methylamine hydrobromide ( 0.2 M, manufactured by Tokyo Kasei Co., Ltd.) and lead (II) bromide (0.2 M, manufactured by Tokyo Kasei Co., Ltd.) were dissolved in a mixed solvent of dimethylformamide and dimethyl sulfoxide at a volume ratio of 4:1.
  • a dimethyl sulfoxide solution of cesium iodide (1.5 M, manufactured by Tokyo Chemical Industry Co., Ltd.) was added thereto so that the amount of cesium charged was 5% in composition ratio, to prepare a perovskite precursor solution.
  • the prepared perovskite precursor solution was dropped onto the tin oxide thin film and spin-coated, and 0.3 mL of chlorobenzene was dropped during spin-coating to form a perovskite precursor film. After that, by heating at 100° C. for 1 hour using a hot plate, a Cs(MAFA)Pb(IBr) 3 layer (photoelectric conversion layer) having a film thickness of about 500 nm was formed.
  • a chlorobenzene solution containing 150 mM 4-tert-butylpyridine and 25 mM lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) was prepared in a glove box under a nitrogen stream.
  • Compound (A-1) which is a hole transport material obtained in Synthesis Example 1
  • the Cs(MAFA)Pb(IBr) 3 layer photoelectric conversion layer
  • a gold electrode (counter electrode 6) was formed on the hole transport layer 5 by forming a film of gold to a thickness of 80 to 100 nm at a degree of vacuum of about 1 ⁇ 10 ⁇ 4 Pa by a vacuum deposition method to prepare a photoelectric conversion device. .
  • Table 1 shows the initial photoelectric conversion efficiency ratio obtained by dividing the obtained initial photoelectric conversion efficiency by the initial photoelectric conversion efficiency of the photoelectric conversion element of Comparative Example 1.
  • Table 2 shows the results of calculating the retention rate (%) over time after storage for 30 days from the initial photoelectric conversion efficiency measurement using the following formula (a-1).
  • Example 2 Preparation of photoelectric conversion element and evaluation of photoelectric conversion characteristics 4-tert-butylpyridine and bis(trifluoromethanesulfonyl)imidelithium as dopants were dissolved in chlorobenzene in a glove box under a nitrogen stream.
  • the compound (A-41) which is the hole transport material obtained in Synthesis Example 3, was dissolved in this chlorobenzene solution to a concentration of 20 mM, and 3 equivalents of the above 4-tert-butylpyridine was added to the compound (A-41).
  • bis(trifluoromethanesulfonyl)imide lithium was adjusted to 0.5 equivalent to prepare a coating solution for a hole transport layer.
  • the hole transport layer coating solution was spin-coated on the Cs(MAFA)Pb(IBr) 3 layer (photoelectric conversion layer) at 100 ° C., and the film thickness was about 200 nm. formed a layer.
  • a photoelectric conversion element was produced in the same manner as in Example 1 except for the above, and the initial photoelectric conversion efficiency and the photoelectric conversion efficiency after storage for 28 days were measured in the same manner as in Example 1. Also, using these, the retention rate (%) over time after storage for 28 days was calculated from the above formula (a-1). Table 1 shows the initial photoelectric conversion efficiency, and Table 3 shows the retention rate (%).
  • Example 3 A photoelectric conversion element was produced in the same manner as in Example 2 except that the dopant 4-tert-butylpyridine and bis(trifluoromethanesulfonyl)imide lithium were not used, and the initial photoelectric conversion efficiency was measured in the same manner as in Example 2. , and photoelectric conversion efficiency after storage for 28 days. Table 3 shows the results of calculating retention rate (%) over time after storage for 28 days using the above formula (a-1).
  • Example 4 A photoelectric conversion device was prepared in the same manner as in Example 2, except that the hole-transporting material compound (A-21) obtained in Synthesis Example 2 was dissolved in a chlorobenzene solution at 50 mM, and spin-coated at room temperature. As in Example 2, the initial photoelectric conversion efficiency and the photoelectric conversion efficiency after storage for 28 days were measured. Using these, Table 3 shows the results of calculating the retention rate (%) over time after storage for 28 days according to the above formula (a-1).
  • Example 5 A photoelectric conversion device was prepared in the same manner as in Example 2, except that the hole-transporting material compound (A-59) obtained in Synthesis Example 4 was dissolved in a chlorobenzene solution at 30 mM and spin-coated at room temperature. As in Example 2, the initial photoelectric conversion efficiency and the photoelectric conversion efficiency after storage for 28 days were measured. Using these, Table 3 shows the results of calculating the retention rate (%) over time after storage for 28 days according to the above formula (a-1).
  • Example 6 A photoelectric conversion element was produced in the same manner as in Example 5, except that 4-tert-butylpyridine and bis(trifluoromethanesulfonyl)imide lithium as dopants were not used and spin coating was performed at 50 ° C. The initial photoelectric conversion efficiency and the photoelectric conversion efficiency after storage for 28 days were measured in the same manner as in . Using these, Table 3 shows the results of calculating the retention rate (%) over time after storage for 28 days according to the above formula (a-1).
  • Example 1 A photoelectric conversion element was produced in the same manner as in Example 1 except that Spiro-OMeTAD (manufactured by Sigma-Aldrich), which is a standard hole transport material represented by the following formula (B-1), was used, and photoelectric conversion was performed. Efficiency was measured. The initial photoelectric conversion efficiency was 9.1%. Further, as an evaluation of durability, Table 2 shows the results of calculating the retention rate (%) after storage for 30 days from the initial photoelectric conversion efficiency measurement using the above formula (a-1).
  • Spiro-OMeTAD manufactured by Sigma-Aldrich
  • B-1 a standard hole transport material represented by the following formula (B-1)
  • Example 2 A photoelectric conversion element was produced and implemented in the same manner as in Example 4 except that Spiro-OMeTAD (manufactured by Sigma-Aldrich), which is a standard hole transport material represented by the following formula (B-1), was used.
  • Spiro-OMeTAD manufactured by Sigma-Aldrich
  • the initial photoelectric conversion efficiency and the photoelectric conversion efficiency after storage for 28 days were measured in the same manner as in Example 2.
  • the initial photoelectric conversion efficiency was 16.0%.
  • the retention rate (%) was calculated from the above formula (a-1). Retention rates are shown in Table 3.
  • the compounds (A-1), (A-21), (A-41) and (A-59) having an acridone derivative skeleton of the present invention were used as hole transport materials. It can be seen that the photoelectric conversion element using a standard hole-transporting material exhibits sufficient photoelectric conversion efficiency and high durability as compared with a photoelectric conversion element using a standard hole-transporting material.
  • the compounds (A-41) and (A-59) of the present invention are used, even if no dopant is used, the retention is higher than when the compound (B-1), which is a standard hole transport material, is used. It was found that a photoelectric conversion element having a high efficiency and high durability can be produced. From this, the photoelectric conversion element using the compound of the present invention can reduce the manufacturing cost by not adding a dopant and a basic additive as additives, and is a simple method that does not require an addition operation. Fabrication by process is possible.
  • a photoelectric conversion device using the compound of the present invention as a hole transport material exhibits good photoelectric conversion efficiency and can provide clean energy as a solar cell capable of efficiently converting sunlight energy into electric energy. It is also possible to expand to EL and image sensors.

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Abstract

Le problème à résoudre par la présente invention est de fournir : un composé qui est utile en tant que matériau de transport de trous pour des éléments de conversion photoélectrique qui peuvent extraire de manière efficace un courant électrique; un élément de conversion photoélectrique et une cellule solaire, dont chacun utilise le composé dans une couche de transport de trous et qui a des caractéristiques de conversion photoélectrique satisfaisantes.　La présente invention concerne un composé qui est représenté par la formule générale (1). La présente invention concerne également : un matériau de transport de trous qui est composé d'un composé représenté par la formule générale (1); et un élément de conversion photoélectrique utilisant ce matériau de transport de trous. Les définitions des symboles dans la formule sont telles que décrites dans la description.
PCT/JP2022/035899 2021-09-29 2022-09-27 Composé, matériau de transport de trous et élément de conversion photoélectrique l'utilisant WO2023054344A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10251633A (ja) * 1997-03-17 1998-09-22 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子
JP2017092336A (ja) * 2015-11-13 2017-05-25 三菱製紙株式会社 全固体型の光電変換素子
CN111484468A (zh) * 2019-01-25 2020-08-04 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10251633A (ja) * 1997-03-17 1998-09-22 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子
JP2017092336A (ja) * 2015-11-13 2017-05-25 三菱製紙株式会社 全固体型の光電変換素子
CN111484468A (zh) * 2019-01-25 2020-08-04 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
AWASTHI ANKUR A; GUPTA NIKITA; SIDDIQUI QAMAR T; PARAB PRADNYA; PALIT DIPAK K; BOSE SANGITA; AGARWAL NEERAJ: "Synthesis of acridone-naphthylamine derivative and its thermally-activated delayed fluorescence studies for application in OLEDs", JOURNAL OF CHEMICAL SCIENCES, vol. 131, no. 9, 4 October 2019 (2019-10-04), New Delhi, XP036899504, ISSN: 0974-3626, DOI: 10.1007/s12039-019-1667-9 *
LE HUONG T., SALEAH RUSRINA, KUNGWAN NAWEE, NGHIEM MAI‐PHUONG, GOUBARD FABRICE, BUI THANH‐TUÂN: "Synthesis, Thermal, Optical and Electrochemical Properties of Acridone and Thioxanthone Based Push‐Pull Molecules", CHEMISTRYSELECT, vol. 5, no. 48, 30 December 2020 (2020-12-30), DE , pages 15180 - 15189, XP093053518, ISSN: 2365-6549, DOI: 10.1002/slct.202003376 *
SHARMA BHARAT K., SHAIKH AZAM M., AGARWAL NEERAJ, KAMBLE RAJESH M.: "Synthesis, photophysical and electrochemical studies of acridone-amine based donor–acceptors for hole transport materials", RSC ADVANCES, vol. 6, no. 21, 1 January 2016 (2016-01-01), pages 17129 - 17137, XP093053520, DOI: 10.1039/C5RA25115J *

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