Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
  • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
  • C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2603/00—Systems containing at least three condensed rings
  • C07C2603/93—Spiro compounds
  • C07C2603/94—Spiro compounds containing "free" spiro atoms
• • 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

• variables R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 independently of each other have the meaning of aryl or hetaryl, with the proviso that not all of the radicals R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 are identical, to the use of compounds of general formula I in organic electronics applications, especially in organic field effect transistors, in organic photodetectors and organic solar cells, specifically in dye-sensitized solar cells and bulk heterojunction solar cells, and to an organic field effect transistor, a dye-sensitized solar cell and a bulk heterojunction solar cell comprising compounds of general formula I.
• DSCs Dye-sensitized solar cells
• the construction of a DSC is generally based on a glass substrate, which is coated with a transparent conductive layer, the working electrode.
• An n-conductive metal oxide is generally applied to this electrode or in the vicinity thereof, for example an approx. 2-20 ⁇ -thick nanoporous titanium dioxide layer (T1O2).
• T1O2 ⁇ -thick nanoporous titanium dioxide layer
• a monolayer of a light- sensitive dye for example a ruthenium complex
• the counterelectrode may optionally have a catalytic layer of a metal, for example platinum, with a thickness of a few ⁇ .
• the area between the two electrodes is filled with a redox electrolyte, for example a solution of iodine ( ) and lithium iodide (Lil).
• the function of the DSC is based on the fact that light is absorbed by the dye, and electrons are transferred from the excited dye to the n-semiconductive metal oxide semiconductor and migrate thereon to the anode, whereas the electrolyte ensures that the charges are balanced via the cathode.
• the n-semiconductive metal oxide, the dye and the (usually liquid) electrolyte are thus the most important constituents of the DSC, though cells comprising liquid electrolyte in many cases suffer from nonoptimal sealing, which leads to stability problems.
• Various materials have therefore been studied for their suitability as solid electrolytes/p-semiconductors.
• Solid DSCs comprising fluorine and tin difluoride doped CsSn as hole conducting material and displaying efficiencies of around 10% were reported by In Chung et al. (Nature Vol. 485, May 24, 2012, 486-490)
• Organic polymers are also used as solid p-semiconductors.
• examples thereof include polypyrrole, poly(3,4-ethylenedioxythiophene), carbazole-based polymers, polyaniline, poly(4- undecyl-2,2'-bithiophene), poly(3-octylthiophene), poly(triphenyldiamine) and poly(N- vinylcarbazole).
• poly(N-vinylcarbazole) the efficiencies reach up to 2%; with a PEDOT (poly(3,4-ethylenedioxythiophene), polymerized in situ, an efficiency of 2.9% was even achieved (Xia et al. J. Phys. Chem.
• WO 98/48433 A1 reports the use of the organic compound 2,2',7,7'-tetrakis(N,N-di-p- methoxyphenyl-amine)-9,9'-spirobifluorene ("spiro-MeOTAD") in DSCs as hole transporting material.
• spiro-MeOTAD 2,2',7,7'-tetrakis(N,N-di-p- methoxyphenyl-amine)-9,9'-spirobifluorene
• Spiro-MeOTAD is likewise examined by Snaith, H. J.; Moule, A. J.; Klein, C; Meerholz, K.; Friend, R. H.; Gratzel (M. Nano Lett.; (Letter); 2007; 7(1 1 ); 3372-3376) as hole transporting material in DSCs.
• photocurrent is directly dependent on the yield in the hole transition from the oxidized dye to the solid p-conductor. This depends essentially on two factors: first on the degree of penetration of the p-semiconductor into the oxide pores, and second on the thermodynamic driving force for the charge transfer, i.e. especially on the difference in the free enthalpy ⁇ between dye and p- conductor.
• the photoactive layer comprises the acceptor and donor compound(s) as a bicontinuous phase.
• the acceptor compound As a result of photoinduced charge transfer from the excited state of the donor compound to the acceptor compound, owing to the spatial proximity of the compounds, a rapid charge separation compared to other relaxation procedures takes place, and the holes and electrons which arise are removed via the corresponding electrodes.
• further layers for example hole or electron transport layers, are often applied in order to increase the efficiency of such cells.
• the donor materials used in such BHJ cells have usually been polymers, for example polyvinylphenylenes or polythiophenes, or dyes from the class of the phthalocyanines, e.g. zinc phthalocyanine or vanadyl phthalocyanine, and the acceptor materials used have been fullerene and fullerene derivatives and also various perylenes.
• Photoactive layers composed of the donor/acceptor pairs poly(3-hexyl-thiophene) (“P3HT”)/ [6,6]-phenyl-C6i-butyric acid methyl ester (“PCBM”), poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene) (“OC1C10- PPV”)/PCBM and zinc phthalocyanine/fullerene have been and are being researched intensively.
• P3HT poly(3-hexyl-thiophene)
• PCBM poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene)
• OC1C10- PPV poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene)
• PCBM poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1
• R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 independently of each other have the meaning of aryl or hetaryl, with the proviso that not all of the radicals R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 are identical.
• X C(R 8 R 9 ) 2 NR 10 , oxygen or sulfur, and R 6 to R 10 hydrogen, alkyl, cycloalkyl, aryl or hetaryl.
• Lg leaving group In general, the leaving group Lg can be any group known to a person skilled in the art as being prone to easily leave the molecule. Typically, Lg consists of or comprises strongly electron- withdrawing atoms or moieties and, thus, is normally split off as anionic species.
• Lg are chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate and triflate which, in view of the aforesaid, leave the molecule as chloride, bromide, iodide, brosylate, nosylate, tosylate, mesylate or triflate anion.
• R 5 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 6 R 7 , where in case of two or more substituents (p equal or greater than 2) these may be identical or different, p 0, 1 , 2, 3, 4 or 5,
• R 6 to R 10 hydrogen, alkyl, cycloalkyl, aryl or hetaryl.
• the Buchwald-Hartwig amination reaction is a well established synthetic route and the reaction conditions can easily be determined by a person skilled in the art. Conversion of aryl bromides to arylamines is specifically addressed in the publication by Guram, A.S.; Rennels, R.A.; Buchwald, S.L. (1995), "A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines", Angewandte Chemie International Edition 34 (12): 1348-1350.
• the abovementioned compounds of general formula I and II and their preferred embodiments are particularly suited for organic electronics applications, especially in organic field effect transistors, dye-sensitized solar cells and bulk heterojunction solar cells with generally low tendency of crystallization and thus enhanced long term stability of the resulting organic electronic devices.
• these compounds typically function as hole transporting materials.
• Another objective of the instant invention is the use of compounds of general formula I and their preferred embodiments in organic electronics applications. Specifically, the
• Another preffered objective of the instant invention is the use of compounds of general formula I and their preferred embodiments in dye-sensitized solar cells and bulk heterojunction solar cells. Further objectives of the instant invention pertain to field effect transistor, dye-sensitized solar cells and bulk heterojunction solar cells comprising compounds of general formula I and their preferred embodiments.
• alkyl, aryl or heteroaryl represents unsubstituted or substituted alkyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl.
• Alkyl comprises straight-chain or branched alkyl.
• Alkyl is preferably Ci-C3o-alkyl, especially Ci- C2o-alkyl and most preferably Ci-Ci2-alkyl.
• alkyl groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n- octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
• branched alkyl groups can be represented by the following formula in which
• R a is selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the Rs
• R a radicals is an integer from 2 to 29.
• the R a radicals are preferably selected from Ci- to Ci2-alkyl, especially Ci- to Cs-alkyl.
• Preferred branched alkyl radicals of the above formula are, for example:
• AlkyI also comprises alkyl radicals whose carbon chains may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, -NR b -, -SO- and/or
• R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
• Substituted alkyl groups may, depending on the length of the alkyl chain, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
• Aryl-substituted alkyl radicals have at least one unsubstituted or substituted aryl group, as defined below.
• the alkyl group of the aralkyi radical may bear at least one further substituent and/or be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, - NR b -, -SO- and/or -SO2- where R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
• Arylalkyl is preferably phenyl-Ci-Cio-alkyl, more preferably phenyl-Ci-C4-alkyl, for example benzyl,
• Halogen-substituted alkyl groups comprise a straight-chain or branched alkyl group in which at least one hydrogen atom or all hydrogen atoms are replaced by halogen.
• the halogen atoms are preferably selected from fluorine, chlorine and bromine, especially fluorine and chlorine.
• haloalkyl groups are especially chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,
• unsubstituted and substituted alkyl radicals which may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -NR b -, -CO-, -SO- and/or -
• dicyclopentylamino dicyclohexylamino, dicycloheptylamino, diphenylamino and dibenzylamino; formylamino, acetylamino, propionylamino and benzoylamino; carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butyl- aminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl,
• octylaminocarbonyl nonylaminocarbonyl, decylaminocarbonyl and phenylamino-carbonyl; aminosulfonyl, n-dodecylaminosulfonyl, ⁇ , ⁇ -diphenylaminosulfonyl, and
• N,N-bis(4-chlorophenyl)aminosulfonyl methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl hexoxycarbonyl, dodecyloxycarbonyl, octadecyloxycarbonyl, phenoxycarbonyl, (4-tert-butylphenoxy)carbonyl and
• cycloalkyi denotes a cycloaliphatic radical having preferably 3 to 10, more preferably 5 to 8, carbon atoms.
• Examples of cycloalkyi groups are especially cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
• Substituted cycloalkyi groups may, depending on the ring size, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents.
• cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.
• substituted cycloalkyi groups are especially 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclopentyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 2-, 3- and 4-propylcyclohexyl, 2-, 3- and 4-isopropylcyclohexyl, 2-, 3- and 4-butylcyclohexyl, 2-, 3- and 4-sec.
• substituted and unsubstituted cycloalkyi groups are cyclopropyl, cyclobutyl, cyclopentyl, 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclo-pentyl, cyclohexyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 3- and 4-propylcyclohexyl, 3- and 4- isopropylcyclohexyl, 3- and 4-butylcyclohexyl, 3- and 4-sec-butylcyclohexyl, 3- and 4-tert- butylcyclohexyl, cycloheptyl, 2-, 3- and 4-methyl-cycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 3- and 4-propylcycloheptyl, 3- and 4-iso-propylcycloheptyl, 3- and 4-butylcycloheptyl,
• aryl comprises mono- or polycyclic aromatic hydrocarbon radicals and monocyclic aromatic hydrocarbon radicals which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
• Aryl has preferably 6 to 14, more preferably 6 to 10, carbon atoms. Examples of aryl are especially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl and pyrenyl, especially phenyl, naphthyl and fluorenyl.
• Substituted aryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyi, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
• the alkyl, alkoxy, alkylamino, alkylthio, cycloalkyi, heterocycloalkyl, aryl and hetaryl substituents on the aryl may in turn be unsubstituted or substituted.
• the substituents on the aryl are preferably selected from alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, fluorine, chlorine, bromine, cyano and nitro.
• Substituted aryl is more preferably substituted phenyl which generally bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents.
• Substituted aryl is preferably aryl substituted by at least one alkyi group ("alkaryl").
• Alkaryl groups may, depending on the size of the aromatic ring system, have one or more (e.g. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more than 9) alkyi substituents.
• alkyi substituents may be unsubstituted or substituted.
• the alkaryl groups have exclusively unsubstituted alkyi substituents.
• Alkaryl is preferably phenyl which bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, alkyi substituents.
• Aryl which bears one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6- diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6- dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and
• unsubstituted or substituted aryl also apply to unsubstituted or substituted aryloxy and unsubstituted or substituted arylthio.
• aryloxy are phenoxy and naphthyloxy.
• hetaryl comprises heteroaromatic, mono- or polycyclic groups and monocyclic groups which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
• ring carbon atoms these have 1 , 2, 3, 4 or more than 4 of the ring heteroatoms.
• the heteroatoms are preferably selected from oxygen, nitrogen, selenium and sulfur.
• the hetaryl groups have preferably 5 to 18, e.g. 5, 6, 8, 9, 10, 1 1 , 12, 13 or 14, ring atoms.
• Monocyclic hetaryl groups are preferably 5- or 6-membered hetaryl groups, such as 2-furyl (furan-2-yl), 3-furyl (furan-3-yl), 2-thienyl (thiophen-2-yl), 3-thienyl (thiophen-3-yl), selenophen-2- yl, selenophen-3-yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, pyrrol-1 -yl, imidazol-2-yl, imidazol-1 -yl, imidazol-4-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 3-isoxazolyl, 4-isoxazolyl, 5- isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazoly
• Polycyclic hetaryl has 2, 3, 4 or more than 4 fused rings.
• the fused-on rings may be aromatic, saturated or partly unsaturated.
• polycyclic hetaryl groups are quinolinyl, isoquinolinyl, indolyl, isoindolyl, indolizinyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzoxadiazolyl; benzothiadiazolyl, benzoxazinyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzotriazinyl, benzoselenophenyl,
• thienothiophenyl thienopyrimidyl, thiazolothiazolyl, dibenzopyrrolyl (carbazolyl), dibenzofuranyl, dibenzothiophenyl, naphtho[2,3-b]thiophenyl, naphtha[2,3-b]furyl, dihydroindolyl,
• Substituted heteroaryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
• Halogen substituents are preferably fluorine, chlorine or bromine.
• the substituents are preferably selected from Ci-C6-alkyl, Ci-C6-alkoxy, hydroxyl, carboxyl, halogen and cyano.
• DSCs generally comprise the following elements: an electrically conductive layer (being part of or forming the working electrode or anode), a photosensitive layer generally comprising a semi- conductive metal oxide and a photosensitive dye, a charge transfer layer and another electrically conductive layer (being part of or forming the counter electrode or cathode).
• ⁇ ⁇ 2 blocking layer was prepared on a fluorine-doped tin oxide (FTO)-covered glass substrate using spray pyrolysis (cf. B. Peng, G. Jungmann, C. Jager, D. Haarer, H. W. Schmidt, M. Thelakkat, Coord. Chem. Rev. 2004, 248, 1479).
• a ⁇ 2 paste (Dyesol), diluted with terpineol, was applied by screen printing, resulting in a film thickness of 1.7 ⁇ .
• the hole transporting material spiro- MeOTAD (commercially availble from Merck KGaA, Darmstadt as SHT-263 livilux ® ) and compounds HTM1 , HTM2 and HTM3 were applied by spin-coating from a solution in DCM (200 mg/mL) also containing 20 mM Li(CFsS02)2N . Fabrication of the device was completed by evaporation of 200 nm of silver as the counter electrode. The active area of the sDSC was defined by the size of these contacts (0.13 cm 2 ), and the cells were masked by an aperture of the same area for measurements.
• the samples were illuminated with monochromatic light from the quartz monochromator with deuterium lamp.
• the power of the incident light beam was (2-5) ⁇ 10 -8 W.
• the negative voltage of -300 V was supplied to the sample substrate.
• the counter-electrode with the 4.5x15 mm 2 slit for illumination was placed at 8 mm distance from the sample surface.
• the counter-electrode was connected to the input of the BK2-16 type electrometer, working in the open input regime, for the photocurrent measurement.
• the 10 "15 - 10 "12 A strong photocurrent was flowing in the circuit under illumination.
• the photocurrent J is strongly dependent on the incident light photon energy hv.
• the J 0 5 f(hv) dependence was plotted.
• Figure 1 Comparison of the lifetime of DSCs comprising hole transporting materials HTM1 , HTM2 and HTM3 according to the instant invention versus a DSC comprising spiro-MeOTAD.
• HTM1 , HTM2 and HTM3 the long term stability of the corresponding DSCs is significantly enhanced over the DSC comprising spiro-MeOTAD. All DSCs were sealed and constantly kept at 60°C and 30% humidity after fabrication.
• Figure 2 Exemplification of the initial condition, i.e. at 25°C after fabrication and before heat treatment, of the the spiro-MeOTAD coating on the silver back electrode of the cells. No spiro- MeOTAD crystals were visible under an optical microscope with crossed polarizers.

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