EP2347460A1 - Mérocyanines pour la fabrication de couches photoactives pour des cellules solaires organiques et des photodétecteurs organiques - Google Patents

Mérocyanines pour la fabrication de couches photoactives pour des cellules solaires organiques et des photodétecteurs organiques

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Publication number
EP2347460A1
EP2347460A1 EP09741311A EP09741311A EP2347460A1 EP 2347460 A1 EP2347460 A1 EP 2347460A1 EP 09741311 A EP09741311 A EP 09741311A EP 09741311 A EP09741311 A EP 09741311A EP 2347460 A1 EP2347460 A1 EP 2347460A1
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Prior art keywords
alkyl
alkylene
aryl
derivatives
component
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German (de)
English (en)
Inventor
Helmut Reichelt
Jae Hyung Hwang
Rüdiger Sens
Jan SCHÖNEBOOM
Peter Erk
Ingmar Bruder
Antti Ojala
Frank WÜRTHNER
Klaus Meerholz
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BASF SE
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BASF SE
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/652—Cyanine dyes
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    • B82—NANOTECHNOLOGY
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    • C07D209/04—Indoles; Hydrogenated indoles
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
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    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
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    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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    • C09B23/10—The polymethine chain containing an even number of >CH- groups
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    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
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    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
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    • 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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    • 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
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    • 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
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • 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 the use of mixtures containing as components
  • NR 110 2 wherein both R 110 together with the N-atom to which they are attached, can form a five- or six-membered saturated ring, or one of R 110 forms with the carbon atom of the benzene ring, which ⁇ -constantly to Carbon atom bearing the NR 110 2 group is a five- or six-membered saturated ring, SR 110 or OR 110 ,
  • L 1 is a divalent aryl or hetaryl radical
  • L 2 is a divalent, optionally mono- or poly-fused carbocycle or heterocycle, which on the one hand with B, on the other hand via the units X 100 and X 101 and the remaining part of the molecule with A in ⁇ -conjugation, or a grouping
  • R 100 is alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cyclylalkyl, arylalkyl or aryl
  • R 110 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cyclylalkyl, arylalkyl or aryl,
  • R 101 is alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cyclylalkyl, arylalkyl, aryl or hetaryl,
  • R 111 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cyclylalkyl, arylalkyl, aryl or hetaryl,
  • R 115 is H, alkyl, partially or perfluorinated alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cyclylalkyl, arylalkyl, Aryl, NHCO-R 100 or N (CO-R 100 ) 2 ,
  • R 118 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 , SR 110 , hetaryl, halogen, NO 2 or
  • the carbon chains of the alkyl and cycloalkyl radicals may be interrupted by one or two non-adjacent oxygen atoms
  • the radicals R 115 and R 210 in formula IIIa together may form a fused benzene ring optionally substituted by R 118
  • the radical R 100 can form a benzannelation which is optionally substituted by R 118 to give this carbon atom and the abovementioned variables, if they occur more than once, may be identical or different from one another,
  • K2) one or more compounds which act accordingly as component K1) as electron acceptor or electron donor,
  • organic semiconductors based on low-molecular or polymeric materials will increasingly be used in addition to the classical inorganic semiconductors. These have many advantages over the classical inorganic semiconductors, for example a better substrate compatibility and better processability of the semiconductor components based on them.
  • Organic Electronics “focuses on the development of new materials and manufacturing processes for the fabrication of electronic devices based on organic semiconductor layers, such as organic field-effect transistors (OFET) and organic light-emitting diodes (OLEDs) eg for use in displays) and organic photovoltaics.
  • OFET organic field-effect transistors
  • OLED organic light-emitting diodes
  • Direct conversion of solar energy into electrical energy in solar cells relies on the internal photoeffect of a semiconductor material, i. the generation of electron-hole pairs by absorption of photons and the separation of the negative and positive charge carriers at a p-n junction or a Schottky contact.
  • the photovoltaic voltage thus generated can cause a photocurrent in an external circuit, through which the solar cell gives off its power.
  • the semiconductor can absorb only those photons that have an energy that is greater than its band gap.
  • the size of the semiconductor band gap thus determines the proportion of sunlight that can be converted into electrical energy.
  • organic solar cells will outperform the traditional silicon-based solar cells because of lower cost, lower weight, the ability to produce flexible and / or colored cells, better ability to fine tune the bandgap. There is thus a great need for organic semiconductors which are suitable for the production of organic solar cells.
  • organic solar cells In order to use solar energy as effectively as possible, organic solar cells usually consist of two absorbing materials with different electron affinity or different ionization behavior. One material then acts as a p-type conductor (electron donor), the other as an n-type conductor (electron acceptor).
  • the first organic solar cells consisted of a two-layer system of a copper phthalocyanine as the p-type conductor and PTCBI as the n-type conductor and showed an efficiency of 1%. In order to use as many as possible incident photons are relatively high
  • Layer thicknesses used eg 100 nm.
  • the excited state generated by the absorbed photons must be a pn junction ("pn-junction") to create a hole and an electron, which then flows to the anode and cathode.
  • pn-junction pn junction
  • organic semiconductors have only excited-state diffusion lengths of up to 10 nm. Even by the best known fabrication methods, the distance over which the excited state must be propagated can be reduced to a minimum of 10 to 30 nm.
  • the photoactive layer contains the acceptor and donor compound (s) as a bicontinuous phase.
  • the acceptor and donor compound s
  • photo-induced charge transfer from the excited state of the donor compound to the acceptor compound causes rapid charge separation compared with other relaxation processes, and the resulting holes and electrons are removed via the corresponding electrodes.
  • Between the electrodes and the photoactive layer are often other layers, such. Hole or electron transport layers, to increase the efficiency of such cells.
  • polymers such as polyvinylphenylenes or polythiophenes, or dyes from the class of phthalocyanines, z.
  • Zn or Vanadylphthalocyanin As Zn or Vanadylphthalocyanin, and used as acceptor fullerene and fullerene derivatives and various perylenes.
  • Photoactive layers of the donor / acceptor pairs Poly (3-hexyl-thiophene) (“P3HT”) / [6,6] -phenyl-C 6- i-butyl acid methyl ester (“PCBM”), poly (2 - Methoxy-5- (3,7-dimethyloctyloxy) -1, 4-phenylenevinylene) (“OCiCio-PPV”) / PCBM and Zn phthalocyanine / fulleren investigated.
  • Halogen refers to fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine.
  • Alkyl is to be understood as meaning substituted or unsubstituted C 1 -C 20 -alkyl radicals. Preference is given to C 1 to C 10 -alkyl radicals, more preferably C 1 to C 6 -alkyl radicals.
  • the alkyl radicals can be both straight-chain and branched.
  • the alkyl radicals may be substituted by one or more substituents selected from the group consisting of C 1 -C 20 -alkoxy, halogen, preferably F, and C 6 -C 8 -aryl, which in turn may be substituted or unsubstituted.
  • Suitable aryl substituents as well as suitable alkoxy and halogen substituents are mentioned below.
  • suitable alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl and octyl and derivatives of the cited alkyl groups with C ⁇ -Cso-aryl, C 1 -C 20 -alkoxy and / or halogen, in particular F, substituted , for example CF3.
  • n-isomers of the radicals mentioned and branched isomers such as isopropyl, isobutyl, isopentyl, sec-butyl, tert-butyl, neopentyl, 3,3-dimethylbutyl, 3-ethylhexyl, etc. are included.
  • Preferred alkyl groups are methyl, ethyl, tert-butyl and CF3.
  • Cycloalkyl is to be understood as meaning substituted or unsubstituted C 3 -C 20 -alkyl radicals.
  • C3 to C10-alkyl radicals are preferred, particularly preferably C3 to C5-alkyl radicals.
  • the cycloalkyl radicals may carry one or more of the substituents mentioned with respect to the alkyl radicals.
  • Suitable cyclic alkyl groups which may likewise be unsubstituted or substituted by the radicals mentioned above with regard to the alkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. If appropriate, these may also be polycyclic ring systems, such as decalinyl, norbornyl, bornanyl or adamantyl.
  • alkyl which is interrupted by one or two non-adjacent oxygen atoms is, for example, 3-methoxyethyl, 2- and 3-methoxy-propyl, 2-ethoxyethyl, 2- and 3-ethoxypropyl, 2-propoxyethyl, 2- and 3-propoxypropyl
  • 2-butoxyethyl, 2- and 3-butoxypropyl, 3,6-dioxaheptoyl and 3,6-dioxaoctyl is, for example, 3-methoxyethyl, 2- and 3-methoxy-propyl, 2-ethoxyethyl, 2- and 3-ethoxypropyl, 2-propoxyethyl, 2- and 3-propoxypropyl.
  • Suitable aryls are C ⁇ -Cso-aryl radicals derived from monocyclic, bicyclic or tricyclic aromatics which contain no ring heteroatoms. Unless they are monocyclic systems, the term aryl for the second ring also means the saturated form (perhydroform) or the partially unsaturated form (for example the dihydroform or tetrahydroformyl), provided the respective forms are known and stable , That is, in the present invention, the term aryl includes, for example, bicyclic or tricyclic radicals in which both both and all three radicals are aromatic, as well as bicyclic or tricyclic radicals in which only one ring is aromatic, and tricyclic radicals wherein two rings are aromatic.
  • aryl examples include: phenyl, naphthyl, indanyl, 1, 2-dihydronaphthenyl, 1, 4-dihydronaphthenyl, indenyl, anthracenyl, phenanthrenyl or 1, 2,3,4-tetrahydronaphthyl.
  • Particularly preferred are C ⁇ -Cio-aryl radicals, for example phenyl or naphthyl, very particularly preferably C ⁇ -aryl radicals, for example phenyl.
  • the aryl radicals may be unsubstituted or substituted by a plurality of further radicals. Suitable further radicals are selected from the group consisting of C 1 -C 20 -alkyl, C 6 -C 30 -aryl or substituents with donor or acceptor action, suitable substituents having donor or acceptor activity being:
  • Preferred substituents with donor or acceptor action are selected from the group consisting of:
  • Cr to C 2 o-alkoxy preferably CrC ⁇ -alkoxy, particularly preferably ethoxy or methoxy
  • C6-C 3 o-aryloxy preferably C ⁇ -Cio-aryloxy, most preferably phenyloxy
  • SiR 3 where the three radicals R are preferably each independently substituted or unsubstituted alkyl or substituted or unsubstituted phenyl, halogen radicals, preferably F, Cl, Br, more preferably F or Cl, most preferably F, halogenated Ci-C 2 o Alkyl radicals, preferably halogenated Ci-C ⁇ -alkyl radicals, most preferably fluorinated CrC ⁇ -alkyl radicals, for.
  • CF 3 CH 2 F, CHF 2 or C 2 F 5 ;
  • Amino preferably dimethylamino, diethylamino or diphenylamino;
  • OH pseudohalo radicals, preferably CN, SCN or OCN, more preferably CN, -C (O) OCrC 4 -alkyl, preferably -C (O) OMe, P (O) R 2 , preferably P (O) Ph 2 or SO 2 R 2 , preferably SO 2 Ph.
  • R in particular Ci-C 2 o alkyl or C6-C 3 O- aryl.
  • Ci-C 6 -alkylene-O-CO-alkyl and -C 6 - alkylene-0-COO-alkyl are derived from the above-described alkyl groups by binding to the moieties Ci-Ce Alkylene-COO, Ci-C 6 -alkylene-O-CO and CrC 6 - alkylene-O-CO-0, wherein the CrC ⁇ -alkylene units are preferably linear. In particular, C 2 -C 4 - alkylene units are suitable.
  • Arylalkyl in particular aryl-CrC 2 o-alkyl groups are mentioned. They are derived from the abovementioned alkyl and aryl groups by formal replacement of a hydrogen atom of the linear or branched alkyl chain by an aryl group. For example, may be mentioned as the preferred arylalkyl benzyl.
  • Hetaryl is to be understood as meaning unsubstituted or substituted heteroaryl radicals having from 5 to 30 ring atoms, which may be monocyclic, bicyclic or tricyclic, some of which can be derived from the abovementioned aryl in which at least one carbon atom in the aryl skeleton is replaced by a heteroatom is replaced.
  • Preferred heteroatoms are N, O and S.
  • the hetaryl radicals have 5 to 13 ring atoms.
  • the skeleton of the heteroaryl radicals is selected from systems such as pyridine and five-membered heteroaromatics such as thiophene, pyrrole, imidazole or furan.
  • backbones may optionally be fused with one or two six-membered aromatic radicals.
  • Suitable anellated heteroaromatics are carbazolyl, benzimidazolyl, benzofuryl, dibenzofuryl or dibenzothiophenyl.
  • the backbone may be substituted at one, several or all substitutable positions, suitable substituents being those already mentioned under the definition of C ⁇ -Cso-aryl.
  • the hetaryl radicals are preferably unsubstituted.
  • Suitable hetaryl radicals are, for example, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, furan -2-yl, furan-3-yl and imidazol-2-yl and the corresponding benzanell faced radicals, in particular carbazolyl, benzimidazolyl, benzofuryl, dibenzofuryl or dibenzothiophenyl.
  • the divalent aryl or hetaryl radicals of the definition of L 1 are derived from the abovementioned aryl and hetaryl radicals by the formal removal of a further hydrogen atom.
  • the component K1 can take over the role of the electron donor, and accordingly the component K2 assumes the role of the electron acceptor. Alternatively, however, the component K1 can also assume the role of the electron acceptor, and accordingly component K2 acts as an electron donor.
  • the way in which the respective component acts depends on the energy of the HOMO or LUMO of the component K1 in relation to the energy of the HOMO or LUMO of the component K2.
  • the compounds of component K1 are typically merocyanines, which usually appear as electron donors. In particular, this is the case if, as component K2, rylene or fullerene derivatives are used, which then generally act as electron acceptors. However, these roles can be reversed in a specific case.
  • component K2 can also obey the structural definition of component K1, so that a compound of the formula I, IIa, IIb, IIIa, INb, INc or Nie the role of the electron donor and another compound of the formula I, IIa, IIb, lilac, INb, INc, and can never assume the role of the electron acceptor.
  • Preferred compounds to be used according to the invention of the formulas I, IIa and / or IIb in component K1 are characterized in that L 2 denotes a group which is selected from the group
  • R 102 arylalkyl, aryl or hetaryl
  • R 112 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 or SR 110 ,
  • R 113 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cycloalkyl, arylalkyl, aryl, hetaryl , NH-aryl, N (aryl) 2 , NHCO-R 100 or N (CO-R 100 ) 2 , R 114 is H, alkyl or partially or perfluorinated alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl or C 1 -C 6 -alkylene-O-CO-O-alkyl,
  • R 116 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cycloalkyl, arylalkyl, aryl, CO 2 R 110 or CN
  • R 117 is H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O-CO-alkyl, C 1 -C 6 -alkylene-O-CO-O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 , SR 110 halogen or hetaryl,
  • component K2 is one or more compounds selected from the group
  • polycyclic aromatic hydrocarbons and their derivatives in particular naphthalene and its derivatives, rylenes, in particular perylene, terrylene and quaterrylene, and their derivatives, Azene, in particular anthracene, tetracene, in particular rubrene, pentacene and derivatives thereof, pyrene and derivatives thereof,
  • thiophenes oligo-thiophenes, condensed / fused thiophenes, such as thienothiophene and bithienothiophene, and derivatives thereof,
  • mixtures which are characterized in that component K2 is one or more fullerenes and / or fullerene derivatives.
  • Q is C 1 -C 10 -alkylene
  • R is aryl or arylalkyl
  • Ci-Cio-Alkylen is in particular a linear chain - (CH2) m -, with m equal to 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 to understand.
  • R denotes a C 1 -C 4 -alkyl radical, in particular a methyl radical
  • Q denotes a propylene chain - (CH 2) 3
  • R represents an optionally substituted phenyl or 2 Thienyl stands.
  • the fullerene derivative is [6,6] -phenyl-C6i- butylklaremethylester ("PCBM").
  • fullerenes may be mentioned C ⁇ o, C70, C76, Cso, Cs2, Cs 4, Cs ⁇ , C90 and C94, in particular the C ⁇ o and C70.
  • An overview of fullerenes which can be used according to the invention is provided, for example, by the monograph by A. Hirsch, M. Brettreich, "Fullerenes: Chemistry and Reactions", Wiley-VCH, Weinheim 2005.
  • component K2 is a C60 fullerene of the formula k2
  • the mixtures to be used according to the invention are characterized in that component K1 is present in a proportion of 10 to 90% by mass, in particular 20 to 80% by mass, and component K2 in a proportion of 90 to 10% by mass, in particular 80% to 20% by mass, is present, wherein the proportions of the components K1 and K2, in each case based on the total mass of the components K1 and K2, supplement to 100% by mass.
  • a compound of formula IIa with a unit L 2 -00 is listed below by way of example:
  • a process for the preparation of photoactive layers which is characterized in that one or more of the compounds of the general formulas I, IIa, IIb, IIIa, IIIb, INb, INc, INd and / or or component K1, even taking into account their preferences, and one or more compounds of component K2, also taking into account their preferences, are deposited on a substrate simultaneously, successively or in alternating sequence by vacuum sublimation.
  • the method is characterized in that the component K1 in a proportion of 10 to 90% by mass, in particular 20 to 80% by mass, and the component K2 in a proportion of 90 to 10% by mass, in particular 80 to 20 mass -%, deposited on the substrate, wherein the proportions of the components K1 and K2, in each case based on the total mass of the components K1 and K2, supplement to 100 mass%.
  • organic solar cells and organic photodetectors which contain photoactive layers which have been prepared using the above-described mixtures containing components K1 and K2, or using the preferred embodiments of the mixtures also described above.
  • Organic solar cells are usually layered and usually comprise at least the following layers: electrode, photoactive layer and counter electrode. These layers are usually on a conventional substrate.
  • Suitable substrates are e.g. oxidic materials, such as glass, quartz, ceramics, SiO 2, etc., polymers, such as polyvinyl chloride, polyolefins, e.g. Polyethylene and polypropylene, polyesters, fluoropolymers, polyamides, polyurethanes, polyalkyl (meth) acrylates, polystyrene and mixtures and composites thereof, and combinations of the substrates listed above.
  • oxidic materials such as glass, quartz, ceramics, SiO 2, etc.
  • polymers such as polyvinyl chloride, polyolefins, e.g. Polyethylene and polypropylene, polyesters, fluoropolymers, polyamides, polyurethanes, polyalkyl (meth) acrylates, polystyrene and mixtures and composites thereof, and
  • Suitable materials for the one electrode are in particular metals, such as e.g. the alkali metals Li, Na, K, Rb and Cs, the alkaline earth metals Mg, Ca and Ba, Pt, Au, Ag, Cu, Al, In, metal alloys, e.g. based on Pt, Au, Ag, Cu, etc. and special Mg / Ag alloys, but also alkali metal fluorides, such as LiF, NaF, KF, RbF and CsF, and mixtures of alkali metal fluorides and alkali metals.
  • the electrode used is preferably a material that essentially reflects the incident light. These include, for example, metal films of Al, Ag, Au, In, Mg, Mg / Al, Ca, etc.
  • the counter electrode consists of a material substantially transparent to incident light, e.g. As ITO, doped ITO, ZnO, TiO 2, Cu, Ag, Au and Pt, the latter metals are present in correspondingly thin layers.
  • an electrode / counterelectrode should be regarded as "transparent” if at least 50% of the radiation intensity is transmitted in the wavelength range in which the photoactive layer absorbs radiation. In the case of several photoactive layers, an electrode / counterelectrode should be considered “transparent” if at least 50% of the radiation intensity is transmitted in the wavelength ranges in which the photoactive layers absorb radiation.
  • one or more further layers may be present in the organic solar cells and photodetectors according to the invention, for example electron transporting layers ("ETL”) and / or hole transporting layers (“HTL”) and / or or blocking layers, eg, exciton-blocking layers ("EBL", exciton blocking layers), which usually do not absorb the incident light, or else layers which serve as charge transport layers and at the same time improve contact with one or both electrodes of the solar cell .
  • ETL and HTL may also be doped to give pin-type cells as they are For example, in the publication by J. Drechsel et al., Thin Solid Films 451-452 (2004), 515-517.
  • organic solar cells are further e.g. in WO 2004/083958 A2, US 2005/0098726 A1 and US 2005/0224905 A1, to which reference is made in its entirety.
  • Photodetectors essentially have a structure analogous to organic solar cells, but they are operated with a suitable bias voltage, which generates a corresponding current flow as measurement response when radiation energy is applied.
  • the processing of the photoactive layers can be carried out from solution.
  • the components K1 and K2 can already be solved together, but also be present separately as a solution of the component K1 and solution of the component K2, wherein the
  • concentrations of components K1 and K2 are typically about a few g / l to tens of g / l of solvent.
  • Suitable solvents are all liquids which evaporate without residue and have sufficient solubility for the components K1 and K2.
  • suitable compounds here are aromatic compounds, such as benzene, toluene, xylene, mesitylene, chlorobenzene or dichlorobenzene, trialkylamines, nitrogen-containing heterocycles, N, N-disubstituted aliphatic carboxylic acid amides, such as dimethylformamide, diethylformamide, dimethylacetamide or dimethylbutyramide, N -Alkyllactams, such as N-methylpyrrolidone, linear and cyclic ketones, such as methyl ethyl ketone, cyclopentanone or cyclohexanone, cyclic ethers, such as tetrahydrofuran, or alcohols, such as methanol, ethanol, propanol, isopropanol or butanol.
  • aromatic compounds such as benzene, tolu
  • mixtures of the abovementioned solvents can also be used.
  • Suitable methods for applying the photoactive layers of the invention of the liquid phase are known in the art.
  • processing by means of spin coating is advantageous, since the thickness of the photoactive layer can be controlled in a simple manner by the amount and / or concentration of the solution used and the rotational speed and / or rotation time.
  • the processing of the solution is usually carried out at room temperature.
  • the components K1 and K2 are separated from the gas phase, in particular by vacuum sublimation.
  • the compounds of the formulas I, IIa, IIb, IIIa, INb, INc, INd and N can generally be purified by sublimation. can already derive starting parameters for the vapor deposition. Usually, temperatures between 100 and 200 ° C. are used for the deposition, but they can also be increased to a range of 300 to 400 ° C., depending on the stability of the compounds of components K1 and K2.
  • mixtures are also claimed which contain as components one or more of the compounds of general formulas I, IIa, IIb, IIIa, INb, INc, INd and / or Nie of component K1, also taking into account the preferences given , and one or more compounds of component K2, also taking into account their preferences listed.
  • the mixtures according to the invention are characterized in that the component K1 in a proportion of 10 to 90% by mass, in particular 20 to 80% by mass, and the component K2 in a proportion of 90 to 10% by mass, in particular 80 to 20% by mass, is present, wherein the proportions of the components K1 and K2, in each case based on the total mass of the components K1 and K2, supplement to 100% by mass.
  • the structure comprises the following layers:
  • Layer 1 1 is a transparent, conductive layer, for example ITO, FTO or ZnO, which is optionally pretreated, for example, with oxygen plasma, UV / ozone rinsing, etc.
  • this layer must be so thin that only little light absorption occurs, but on the other hand thick enough to ensure a satisfactory lateral charge transport within the layer.
  • the thickness of the layer is 20-200 nm and it is deposited on a substrate such as glass or a flexible polymer (for example PET).
  • Layer 12 consists of one or more HTLs with a high ionization potential (> 5.0 eV, preferably 5.5 eV).
  • This layer can either consist of organic material, such as poly (3,4-ethylenedioxythiophene) doped with poly (styrenesulfonate) (PEDOT-PSS), or, for example, of Ir-DPBIC (Tris-N, N'-diphenylbenzimidazol-2-ylidene).
  • organic material such as poly (3,4-ethylenedioxythiophene) doped with poly (styrenesulfonate) (PEDOT-PSS), or, for example, of Ir-DPBIC (Tris-N, N'-diphenylbenzimidazol-2-ylidene).
  • the layer thickness is 0-150 nm.
  • layer 12 is composed of organic material, it can be mixed with a p-type dopant whose LUMO energy is in the same or lower energy range as the HOMO of the HTL.
  • dopants are, for example, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 TCNQ), WO 3 , MoO 3 , or the substances described in WO 2007/071450 A1.
  • Layer 13 consists of the electron donor. Usually, the layer should be so thick that it absorbs as much light as possible, but on the other hand, sufficiently thin, in order to be able to effectively dissipate the charges formed. As a rule, the thickness is 5-200 nm.
  • Layer 14 consists of the electron acceptor. Again, as for layer 13, the thickness should be sufficient to absorb as much light as possible, but on the other hand, the charges formed must be effectively dissipated. Usually, this layer also has a thickness of 5-200 nm.
  • Layer 15 is an EBL / ETL and should have a larger optical bandgap than the materials of layer 14 to reflect the exitons, yet still have sufficient electron transport properties.
  • Suitable compounds are 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline (BCP), 4,7-diphenyl-1, 10-phenanthroline (Bphen), 1, 3-bis [2- (2, 2'-bipyridin-6-yl) 1, 3,4-oxadizo-5-yl] benzene (BPY-OXD), ZnO, TiO 2, etc.
  • BCP 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline
  • Bphen 4,7-diphenyl-1, 10-phenanthroline (Bphen)
  • BPY-OXD 1, 3-bis [2- (2, 2'-bipyridin-6-yl) 1, 3,4-oxadizo-5-yl] benzene
  • ZnO TiO 2 etc.
  • this may
  • Suitable materials are Cs 2 CO 3 , pyronin B (PyB), described, for example, in WO 2003/070822 A2, Rodamine B, described, for example, in WO 2005/036667 A1, Cobaltocene and those in WO 2007 / 071450 A1 mentioned connections.
  • the layer thickness is usually 0-150 nm.
  • Layer 16 is made of a low work function material.
  • these are metals such as Ag, Al, Ca, Mg or their mixtures.
  • the layer thickness is usually 50-1000 nm and should be chosen sufficiently so that most of the light is reflected in the wavelength range of 350-1200 nm.
  • the usual pressures during the vapor deposition are between 10 " 4 and 10 " 9 mbar.
  • the deposition rate usually varies between 0.01 nm / second and 10 nm / second.
  • the temperature of the substrate during the deposition can be varied in a temperature range between -100 0 C and 200 0 C in order to influence the morphology of the corresponding layer targeted.
  • the deposition rate is usually between 0.1 nm / second and 2.0 nm / second.
  • an annealing at 60 0 C to 100 0 C for a few minutes to a few can Connect hours to achieve a more intimate contact of the layers.
  • a treatment with solvent vapor for example of toluene, xylene, chloroform, N-methylpyrrolidone, dimethylformamide, ethyl acetate, chlorobenzene and dichloromethane or other solvents for the appropriate duration can be made.
  • the structure comprises the following layers:
  • the layers 21 and 22 correspond to the layers 11 and 12 of structure A).
  • the layer 23 can be produced by co-evaporation or by solution processing with customary solvents - this has already been described above.
  • the proportion of the electron donor in both cases is preferably 10 to 90% by mass, in particular 20 to 80% by mass.
  • the proportion of electron acceptor is in addition to 100% by mass.
  • the layer must be so thick that enough light is absorbed, but still so thin that the charge carriers can be effectively dissipated.
  • the layer is 5 - 500 nm thick.
  • the ETL layer 24 may consist of one or more layers of low LUMO energy ( ⁇ 3.5 eV) materials.
  • These layers can either consist of organic compounds, such as C60 fullerene, BCP, Bphen or BPY-OXD, or of inorganic compounds, such as ZnO, OO2, etc., and are generally between 0 nm and 150 nm thick. In the case of organic layers, these may be mixed with the dopants already mentioned above.
  • Layers 25 and 26 correspond to layers 15 and 16 of structure A). Similarly, the deposition rates and aftertreatments correspond to those of structure A).
  • the structure comprises the following layers:
  • Tandem cells contain two or more subcells, which are usually connected in series, with recombination layers being arranged between the individual subcells.
  • Layer 31 corresponds to the structure of the aforementioned layers 1 1 and 21 of structure A) and B).
  • the layers 32 and 34 are individual subcells and correspond in function to individual cells as in structure A) and B) with the difference that they do not contain electrodes 11/16 and 21/26.
  • the subcells therefore consist of the layers 12 to 15 of the structure A) or 22 to 25 of the structure B).
  • the sub-cells can either contain all merocyanines as component K1 or K2 or a sub-cell contains one or more merocyanines and the remaining sub-cells contain combinations of other materials, such as C60-fullerene / Zn-phthalocyanine, oligothiophene (for example DCV5T) / C60-fullerene ( as described in WO 2006/092134 A1), or one of the sub-cells is a dye-sensitized solar cell (DSSC) or a polymer cell, such as in the combination
  • DSSC dye-sensitized solar cell
  • both cells of the structure A) and of the structure B) can be contained as subcells.
  • the combination of materials / subcells is chosen so that the light absorptions of the subcells do not overlap too much, but in total cover the spectrum of sunlight, which leads to an increase in the current efficiency.
  • considering optical interferences taking place in the cell it makes sense to place a subcell having absorption in the shorter wavelength range closer to the electrode 36 than a subcell having absorption in the longer wavelength range.
  • the recombination layer 33 causes the recombination of oppositely charged charge carriers in adjacent subcells.
  • Metal clusters for example of Ag or Au, can act as active constituents in the recombination layer, or the recombination layer consists of a combination of highly doped n- and p-conducting layers (as described, for example, in WO 2004/083958 A2).
  • layer thicknesses of 0.5 to 20 nm are usually set, and in the case of the combined doped layers, thicknesses of 5 to 150 nm are set.
  • Further subcells can be applied to the subcell 34, in which case further recombination layers, such as layer 33, must also be present.
  • the material for the electrode 36 depends on the polarity of the subcells. At normal polarity, the aforementioned low work function metals such as Ag, Al, Mg, and Ca are contemplated. In inverted polarity, high workfunction materials are commonly used, such as Au, Pt, PEDOT-PSS.
  • tandem cells which contain subcells connected in series
  • the sub-voltages add up, but the total current is limited by the sub-cell with the lowest current / current density. Therefore, the individual subcells should be optimized so that their individual current strengths / current densities have similar values.
  • the merocyanines also referred to as Mcy hereinafter
  • Mcy merocyanines
  • NPD from the company Alfa Aesar; once sublimated
  • the ITO was sputtered onto the glass substrate to a thickness of 140 nm.
  • the resistivity was 200 ⁇ cm and the roughness mean square (RMS) ⁇ 5 nm.
  • the substrate was treated with ozone for 20 minutes prior to deposition of the further layers under UV light.
  • Cells of structure A) and B) were prepared under high vacuum (pressure ⁇ 10 " 6 mbar).
  • the cell of structure A) (ITO / merocyanine / C60 / Bphen / Ag) was prepared by sequential deposition of the merocyanine and C60 on the ITO substrate. The deposition rate was 0.1 nm / second for both layers. The evaporation temperatures of the merocyanines are listed in Table 1. C60 was deposited at 400 ° C. After the Bphen layer had been applied, finally, a 100 nm thick Ag layer was vapor-deposited as a top electrode. The cell had an area of 0.031 cm 2 .
  • composition B ITO / (merocyanine: C60 - 1: 1 by weight) / C60 / Bphen / Ag
  • the merocyanine and the C60 were coevaporated and deposited on the ITO at the same deposition rate of 0.1 nm / Second applied, so that in the mixed active layer, a mass ratio of 1: 1 was present.
  • the Bphen and Ag layers were identical to the corresponding layers of structure A).
  • An AM 1.5 simulator from Solar Light Co. Inc. with xenon lamp (model 16S-150 V3) was used.
  • the UV range below 415 nm was filtered out and the current-voltage measurements were made at ambient conditions.
  • the intensity of the solar simulator was calibrated with a monocrystalline FZ solar cell (Fraunhofer ISE) and the deviation factor was determined to be almost 1.0.
  • Thickness thickness (mV) (mA / cm 2 ) (%)

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Abstract

La présente invention concerne l'utilisation de mélanges qui contiennent comme composant K1) une ou plusieurs mérocyanines sélectionnées dans le groupe des composés de formules générales (I), (IIa), (IIb), (IIIa), (IIIb), (IIIc), (IIId) et (IIIe) comme définies plus précisément dans la description, comme donneur et/ou accepteur d'électrons, et comme composant K2) un ou plusieurs composés qui agissent comme accepteur et/ou donneur d'électrons à l'opposé des composants K1), pour la fabrication de couches photoactives pour des cellules solaires organiques et des photodétecteurs organiques. L'invention porte également sur un procédé de fabrication de couches photoactives, sur des cellules solaires organiques et des photodétecteurs organiques correspondants, ainsi que sur des mélanges qui contiennent comme composants un ou plusieurs composés de formules générales (I), (IIa), (IIb), (IIIa), (IIIb), (IIIc), (IIId) et (IIIe) et/ou (IIIe) du composant K1, comme défini plus précisément dans la description, et un ou plusieurs composés du composant K2.
EP09741311A 2008-10-31 2009-10-30 Mérocyanines pour la fabrication de couches photoactives pour des cellules solaires organiques et des photodétecteurs organiques Withdrawn EP2347460A1 (fr)

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