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  • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
  • C07F9/3839—Polyphosphonic acids
  • C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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  • C07F9/02—Phosphorus compounds
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  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/0029—Processes of manufacture
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  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/20—Light-sensitive devices
  • H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
  • H01G9/2009—Solid electrolytes
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  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/20—Light-sensitive devices
  • H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
  • H01G9/2018—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte characterised by the ionic charge transport species, e.g. redox shuttles
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  • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
  • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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  • H10K30/80—Constructional details
  • H10K30/81—Electrodes
  • H10K30/82—Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
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  • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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  • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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  • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
  • H10K2102/10—Transparent electrodes, e.g. using graphene
  • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
  • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E10/00—Energy generation through renewable energy sources
  • Y02E10/50—Photovoltaic [PV] energy
  • Y02E10/542—Dye sensitized solar cells
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E10/00—Energy generation through renewable energy sources
  • Y02E10/50—Photovoltaic [PV] energy
  • Y02E10/549—Organic PV cells

Definitions

• the present invention seeks to provide HTMs that are relatively tolerant of perovskite processing and any patterned surface such as pyramidal structured silicon with a height of several microns that can be formed by wet chemical etching, such as in solar cells is common, have been processed, can conformally cover.
• ZDZ (II) wherein Z and D are homocyclic or at least one of Z or D comprises a heteroatom selected from the group consisting of N, S, O, Si and Z is a Cs or C ⁇ substituted or unsubstituted aromatic group D is N or a C 8 or C 8 aromatic group wherein two carbon atoms of the aromatic group D are each bonded to one of the two aromatic Z groups, a tricycloundecane
• R is a substituent
• the FMs act as a passivating agent that reduces pad carrier recombination between the TCO and the perovskite, as well as a means of modifying the wettability of the TCO.
• a preparation without FMs is always possible and for selected proportions HTF, F and A without any disadvantage.
• the proportion x of HTM in the mixture is in the range of 0.02 to 1.
• n is preferably 1 or 2.
• D is a Cs or C6 heteroaromatic group, wherein the heteroatom is N, Si, S and / or O.
• the linking fragment L is one that is selected from Ci to C 9 - alkylene, C 4 - to C2o-arylene, C 4 - to C2o-heteroarylene, C 4 - to C2o-alkylarylene, C 4 - to C2o-heteroalkylarylene, wherein the heteroatoms are selected from O, N, S, Se, Si and wherein said alkylenes, arylenes, heteroarylenes, alkylarylenes, heteroalkylarylenes, heteroalkylarylenes, if they comprise three or more carbon atoms, can be linear, branched or cyclic , in particular selected from one of
• dashed lines represent the bond connecting L to the HTF of Formula II or III.
• dashed lines represent the bond by which A is joined to L according to any one of the preceding claims and R 'is preferably aliphatic.
• Another aspect of the invention is the provision of a hole-conducting material comprising the inventive compound.
• Yet another aspect of the present invention relates to an opto-electrical and / or photoelectric device comprising the inventive compound according to one of the aforementioned embodiments.
• the optoelectrical and / or photoelectric device comprises a hole-conducting material, wherein the hole-conducting material comprises the compound of formula II or III.
• the optoelectronic and / or photoelectrochemical component is preferably a photovoltaic solid-state device which is a solid-state solar cell which contains an organic-inorganic perovskite as a sensitizing molecule in the form of
• perovskite in the sense of this description refers to the "perovskite structure” and not specifically to the perovskite material CaTiCb.
• perovskite includes any material and preferably refers to any material having the same crystal structure type as calcium titanium oxide and to materials wherein the divalent cation is replaced by two separate monovalent cations.
• the perovskite structure has the general stoichiometry AMX 3 , where "A” and “M” are cations and "X” is an anion. The cations "A” and "M” can
• the perovskite formulas include structures having one (1), two (2), three (3) or four (4) cations, which may be the same or different, and / or one or two (2) anions and / or metal atoms carrying two or three positive charges according to the formulas given elsewhere in this specification.
• organic-inorganic perovskite layer material of the optoelectronic and / or photoelectrochemical component has a perovskite structure of one of the following formulas:
• a 1 , A 2 , A 3 , A 4 are either organic monovalent cations or mixtures thereof, which are independently selected from primary, secondary, tertiary or
• quaternary organic ammonium compounds including N-containing fletero rings and ring systems, wherein A and A 'are independently 1 to 60 carbon atoms and 1 to 20 fletero atoms (such as methyl ammonium or ammonium amininium) or inorganic cations (such as Na, K, Rb, Cs) exhibit.
• B is an organic divalent cation selected from primary, secondary, tertiary or quaternary organic ammonium compounds having 1 to 60 carbon atoms and 2 to 20 heteroatoms and having two positively charged nitrogen atoms;
• - M is a divalent metal cation selected from the group consisting of Cu 2+ , Ni 2+ , Co 2+ , Fe 2+ , Mn 2+ , Cr, Pd 2+ , Cd 2+ , Ge 2+ , Sn 2 + , Pb 2+ , Eu 2+ or Yb 2+ ;
• - N is selected from the group of Bi 3+ and Sb 3+ ;
• - X is independently selected from Cf, Br, G, NCS, CN and NCO ⁇ X may also be a mixture of the listed halides / anions.
• the compound of the invention for forming a SAM is characterized as follows.
• the anchor group A is made of a
• the hole-conducting fragment HTF is selected from the formula (II) (Z-D-Z) wherein D is N and Z is a C6-cyclic aromatic group substituted with a methoxy group. Another preferred
• Embodiment corresponds to the previously described, wherein Z is not with a
• Methoxy group is substituted. Both embodiments have in common that they can be prepared without filler molecules (FM), and without losses in their characterizing properties and stability.
• FM filler molecules
• Another aspect of the present invention is the use of the inventive compound as a hole-conducting material in an optoelectronic and / or
• the method for forming the inventive compound as SAM on a TCO for use in inverted architecture perovskite solar cells is to be realized by two methods, one method comprising the steps:
• L is a linking fragment
• A is an anchor group
• HTF is a hole-conducting
• Tricyclotridecane or a tricyclotetradecane derivative Tricyclotridecane or a tricyclotetradecane derivative
• R is a substituent, where the FM is generally a molecule or mixture of molecules selected from an anchor group (eg, phosphonic acid, phosphoric acid, sulfuric acid, sulfonic acid,
• an anchor group eg, phosphonic acid, phosphoric acid, sulfuric acid, sulfonic acid
• Examples of an FM are ethyl or
• Butylphosphonic acid (“C2" or “C4") or (aminomethyl) phosphonic acid.
• the solvent for the solution any liquid capable of dissolving the compound and guaranteeing the immersion of a surface can be selected.
• the concentration of the compound in the solution is preferably in the range of 0.01 to 100 mM per liter.
• the time for immersing the surface to form the SAM should be at least sufficient for the molecules to bind to the oxide surface and is preferably in the
• the substrate is then thermally baked and / or washed.
• the compounds according to the invention, with and without FM are spin-coated in a solution (for example, by rotary evaporation). The optimal procedure for the selected HTM and possible substrates should be determined experimentally if necessary.
• FIG. 5 A) FTIR absorption spectra of monolayers on Si / ITO substrate prepared from (a)
• Fig. 6 A) contact angle dependence on percentage of V1036 in the SAM composition; B) equilibrium contact angle of perovskite solution to 100% C4 SAM; PTAA; 100% V1036 SAM.
• Fig. 7 J-V characteristic of the most powerful PSCs with PTAA and SAM HTMs.
• Figure 8 JV characteristic of forward and backward scanning of the most powerful PSC with PTAA and 10% V1036 90% C4 SAM HTMs.
• B EQE and integrated Jsc of the most powerful PSC with PTAA and 10% V1036 90% C4 SA-HTMs. The inset shows the statistical distribution of the Jsc.
• Fig. 9. REMs of PTAA and 10% V1036 90% C4, above and in cross section.
• V olecular vibrations of CN bonds are visible as intense bands near 1238 cm 4 .
• Two average intensity bands near 1438 to 1442 and 1461 to 1466 cm 4 contain a high proportion of symmetric and asymmetric CFb deformation vibrations of the methoxy group.
• Control device with PTAA showed a slightly higher efficiency of 18.4% PCE.
• Sum frequency is generated when infrared and visible pulses overlap in time and space on the sample surface. All spectra in this work were recorded with a polarization combination ssp (s - SPG, s - VIS, p - IR). The intensity of the visible beam has been attenuated to avoid damaging the samples ( ⁇ 30 m ⁇ ). The generated sum frequency light is filtered with a monochromator and detected with a photomultiplier tube (PMT).
• PMT photomultiplier tube
• the SA-HTMs were formed by the above method.
• the HTM SAMs were obtained by immersing UV ozone-treated ITO substrates in a 1 mM / L solution of the corresponding phosphonic acid molecules dissolved in isopropanol for 20 hours, followed by annealing at 100 ° C for 1 hour, followed by washing with isopropanol and chlorobenzene.
• mixtures of V1036 and n-butylphosphonic acid (C4) with different ratios were investigated in addition to the pure V1036 SAM.
• the perovskite coated sample is annealed for 60 minutes on a hot plate at 100 ° C.
• R ' hydrogen, Cl- to C9-alkyl group
• R "' hydrogen, alkyl (Cl to C12)
• V1036 and mixed V1036 and n-butylphosphonic acid (C4) SAMs were prepared by immersing UV ozone-treated ITO substrates in a 1 mM solution of
• the V1193 in a solution was photographed on ITO substrates and then annealed at 100 C for 10 minutes. Washing is optional in this case.
• the VI 193 shows the VI 036 improved properties, as can be seen from FIG.
• HTM SAMs according to the invention, V1036, VI 193, VI 194 and for comparison also to PTAA, in a diagram.
• the data comes from a component analysis.
• the measured parameters were determined at a light intensity equivalent to a sun (AM 1.5 g standard).
• the bars show the largest measured photoluminescent lifetimes.
• the area between the curved solid lines indicates the maximum and minimum QFLS values that were measured (from 3 Vl036 samples, 8 VI 193 samples and 9 VI l94 samples). Error bars for open circuit voltage Voc and efficiencies indicate standard deviation, from measurements on 38 Vl036 cells, 56 PTAA cells, 42VI 193 cells and 40Vl94 cells. A clear correlation between efficiency, Voc, photoluminescence (PL) lifetimes and QFLS can be seen.
• the SAMs VI 193 and VI 194 outperform PTAA, the current standard in highly efficient inverted perovskite solar cells, in PL lifetime, QFLS, and device performance.
• the values for VI 036 approximate those of PTAA.
• the dashed line indicates the PL lifetime on glass as a reference.
• the HTM SAMs according to the invention are distinct from PTAA
• the new HTM may possibly be extended to serve as a model system for substrate-based perovskite nucleation and passivation control.

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