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Definitions

• the present invention relates to compounds of the general formulas (I) and (II), their use as electron donor and / or electron acceptor material in an optoelectronic component and to an optoelectronic component containing at least one compound as defined herein.
• optoelectronic component includes organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs), organic solar cells (OSCs), organic optical Detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs) understood.
• OICs organic integrated circuits
• OFETs organic field effect transistors
• OFTs organic thin film transistors
• OLETs organic light emitting transistors
• OSCs organic solar cells
• organic optical Detectors organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs) understood.
• small molecules are understood as meaning non-polymeric organic, monodisperse molecules in the mass range between 100 and 2000 grams / mole. So far, the typical efficiencies of 10-20% for inorganic solar cells have not yet been achieved. But organic solar cells are subject to the same physical limitations such as inorganic solar cells, which is why, after appropriate development work at least theoretically similar efficiencies are expected.
• Organic solar cells consist of a series of thin layers (which are typically each 1 nm to 1 m thick) of organic materials, which are preferably vapor-deposited in vacuum or sputtered from solution.
• the electrical contacting can be effected by metal layers, transparent conductive oxides (TCOs) and / or transparent conductive polymers (PEDOT-PSS, PANI).
• a solar cell converts light energy into electrical energy.
• photoactive is understood here, namely the conversion of light energy into electrical energy.
• solar cells do not directly generate free charge carriers by light, but due to a less pronounced attenuation of the mutual attraction, quasiparticles, so-called excitons (electrically neutral excitation states, bound electron-hole pairs) are formed. Only in a second step, these excitons are separated into free charge carriers, which then contribute to the electric current flow.
• organic-based devices over conventional inorganic-based devices (semiconductors such as silicon, gallium arsenide) is the sometimes extremely high optical absorption coefficients (up to 2x10 5 cm 1 ), which allow efficient absorber layers of just a few nanometers thickness to be produced. so that offers the opportunity to produce very thin solar cells with low material and energy costs. Further technological aspects are the low costs, the organic semiconductor materials used being very cost-effective when produced in large quantities; the possibility of producing flexible large-area components on plastic films, and the almost unlimited possibilities of variation and the unlimited availability of organic chemistry.
• organic solar cells Since no high temperatures are required in the production process (substrate temperatures of a maximum of 1 10 ° C. are not exceeded), it is possible to use organic solar cells as components both flexibly and over a large area on inexpensive substrates, e.g. Metal foil, plastic film or plastic fabric to produce. This opens up new fields of application which remain closed to conventional solar cells. Due to the almost unlimited number of different organic compounds, the materials can be tailored to their specific task.
• n or p denotes an n- or p-type doping, which leads to an increase in the density of free electrons or holes in the thermal equilibrium state.
• i-layer designates an undoped layer (intrinsic layer).
• One or more i-layer (s) may consist of layers of a material as well as a mixture of two materials (so-called interpenetrating networks).
• the charge carrier pairs in organic semiconductors are not freely present after absorption, as already mentioned, but exist as exciton quasiparticles. In order to harness the energy present in the exciton as electrical energy, this exciton must be separated into free charge carriers.
• the photoactive interface can be used as an organic donor-acceptor interface (CW Tang, Appl. Phys. Lett., 1986, 48, 183) or an inorganic semiconductor interface (B. O'Regan, M. Grätzel, Nature, 1991 , 353, 737).
• the excitons pass through diffusion to such an active interface, where electrons and holes are separated. This can lie between the p (n) layer and the i-layer or between two i-layers. In the built-in electric field of the solar cell, the electrons are now transported to the n-area and the holes to the p-area.
• the transport layers are transparent or largely transparent materials with a wide band gap (wide-gap).
• wide-gap materials in this case materials are referred to, the absorption maximum in the wavelength range ⁇ 450 nm, preferably at ⁇ 400 nm.
• an organic material is referred to as hole-conducting if in the material the charge carriers formed as a result of light absorption and charge separation at a heterojunction ("photogenerated charge carriers") are transported in the form of holes
• photogenerated charge carriers are transported in the form of holes
• an organic material is said to be electron conducting when photogenerated carriers are transported in the form of electrons in the material
• An interface region between the electron-conducting and hole-conducting materials is referred to as a heterojunction.
• a heterojunction between the electron-conducting and the hole-conducting material is referred to as a photoactive heterojunction when excitation states in which charge carriers are bound and which are also called excitons formed by light absorption in the electron-conducting and / or hole-conducting material are in the region of the hetero Transition are separated into the individual charge carriers, namely electrons and holes, which in turn are then transported by the electron-conducting material / the hole-conducting material to contacts where electrical energy can be tapped.
• a heterojunction between the electron-conducting and the hole-conducting material is referred to as a flat or planar heterojunction when the interface between the electron-conducting and the hole-conducting material is formed as a substantially contiguous surface between the two material regions, namely a region of the electron-conducting material and a portion of the hole-conducting material (see CW Tang, Appl Phys Lett, 1986, 48 (2), 183-185; or N. Karl et al., Mol. Cryst. Liq. Cryst, 1994, 252; 243-258).
• a heterojunction between the electron-conducting and the hole-conducting material is a volume heterojunction when the electron-conducting material and the hole-conducting material are at least partially mixed with each other, so that the interface between the electron-conducting and the hole-conducting material comprises a plurality of interface portions which overlay the volume of the material mixture are distributed (see, for example, CJ Brabec et al., Adv. Funct. Mater., 201 1, 11, 15).
• materials of photoactive layers in organic photoactive devices have a high absorption coefficient in as broad a wavelength range as possible, which is tuned to the solar spectrum.
• the im Haibieitermateriai by absorption-generated exciton should be able to diffuse without large energy losses to the photoactive heterojunction, whereby an occurring Stokes shift should be as low as possible.
• Long exciton diffusion lengths make it possible to maximize the thickness of the organic layers in which absorbed light contributes to the photocurrent, thus further improving the efficiency of the organic photoactive device.
• a highest occupied energy level (HOMO) and a lowest unoccupied energy level (LUMO) of the organic acceptor material (electron-conducting material) and the organic donor material (hole-conducting material) are preferably to be selected such that efficient separation of the excitons in Electrons on the acceptor material and holes on the donor material takes place, on the other hand, the free energy of the system of generated electron and hole is as large as possible. The latter leads to a maximization of the idle photovoltage of the device.
• the charge carriers should be spatially separated quickly. Good electron transport on the acceptor material and good hole transport on donor material ensures low losses and leads to a good filling factor of the current-voltage characteristic of the organic photoactive component
• WO 2006092134 A1 discloses compounds which have an acceptor-donor-acceptor structure, the donor block having an extended ⁇ system.
• WO 2009051390 discloses thiophene-based acceptor-donor dyes for use in dye-sensitive solar cells.
• WO 002008145172 A1 introduces novel phthalocyanines for use in solar cells.
• US 7655809 B2 discloses compounds of 5 condensed carbon cycles in series and their use as organic semiconductors.
• WO 20061 1 151 1 A1 and WO 20071 16001 A2 disclose rylenetetracarboxylic acid derivatives for use as active layers in photovoltaics.
• the object of the invention is therefore to provide an organic material which is vaporizable in a vacuum and can be used as an electron donor and / or electron acceptor material in an optoelectronic component, in particular as a light absorber in an organic solar cell.
• the organic material is characterized by a photoactive region comprising a photoactive volume heterojunction between an electron-conducting organic material and a hole-conducting organic material.
• the organic material is a conjugated donor-acceptor oligomer (D-A oligomer) wherein the donor moiety (D) is an extended ⁇ electron donor block comprising a quinoidal system.
• D-A oligomer conjugated donor-acceptor oligomer
• the compounds of the invention are characterized by increased thermal stability, so that their use in evaporation systems is possible. With the compounds of the invention, the entire solar spectrum in the visible and in the near infrared spectral range can be covered.
• a first subject of the present invention is therefore a compound of general formula (I) or general formula (II) in which
• Y, Y 1 , Y 2 , Z, Z 1 and Z 2 are each independently oxygen, sulfur, selenium or NR 3 ;
• X is a substituted or unsubstituted quinoid aromatic, quinoidal polyaromatic, quinoid heteroaromatic or quinoidal polyheteroaromatic;
• R and R 2 are each, independently of one another, hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl, C 1 -C -20 -perfluoroalkyl, substituted or unsubstituted benzyl or halogen, or R 1 and R 2 together form a substituted or unsubstituted aromatic, heteroaromatic or alicyclic, optionally containing heteroatoms;
• R 3 is hydrogen, C 1 -C 20 alkyl, aryl, heteroaryl or benzyl
• A is CN, COOH, COOR 4 , perfluoroalkyl, pyridyl, pyrimidinyl, triazinyl, 1, 3,4-oxadiazolyl, 1, 3,4-thiadiazolyl, perfluoropyridyl, tetrafluorobenzonitrile, trifluoroisophthalonitrile, phenyl (R 5 ) s or tolyl (R) 4, wherein, in Pyrimidyi, triazinyl, 1, 3,4-oxadiazolyl and 1, 3,4-thiadiazolyl any hydrogens may be replaced by F and / or CN;
• R 4 is C 1 -C 20 alkyl, aryl, benzyl or C 1 -C 20 perfluoroalkyl
• R 5 with each occurrence independently of one another is hydrogen, Cl, I, Br, F, CN or CF 3, the compound not being a compound of the following compounds 13a to 21a:
• a further subject of the present invention is, moreover, the use of at least one compound of the general formula (I) and / or (II) in which
• Y, Y 1 , Y 2 , Z, Z 1 and Z 2 are each independently oxygen, sulfur or NR 3 ;
• X is a substituted or unsubstituted quinoid aromatic, quinoidal polyaromatic, quinoid heteroaromatic or quinoidal polyheteroaromatic;
• R and R 2 are each independently hydrogen, C1-C20 alkyl, or R and R 2 together form a substituted or unsubstituted aromatics, heteroaromatics or alicyclic optionally containing heteroatoms;
• R 3 is hydrogen, C 1 -C 20 alkyl, aryl, heteroaryl or benzyl
• A is CN, COOH, COOR 4 , perfluoroalkyl, pyridyl, pyrimidinyl, triazinyl, 1, 3,4-oxadiazolyl, 1, 3,4-thiadiazolyl, perfluoropyridyl, tetrafluorobenzonitrile, trifluoroisophthalodinitrile, phenyl (R 5 ) s or tolyl (R 5 ) .i wherein, in pyrimidyl, triazinyl, 1, 3,4-oxadiazolyl and 1, 3,4-thiadiazolyl any hydrogens may be replaced by F and / or CN and / or Cl; and
• R 5 with each occurrence is independently of one another hydrogen, Cl, I, Br, F, CN or CF 3, as light absorber or IR absorber, in particular in an optoelectronic component, for example an organic electroluminescent device (OLED), an organic integrated circuit (O IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, a organic photoreceptor, an organic field quench device (O-FQD), an organic light-emitting electrochemical cell (O-LEC), an organic laser diode (O-laser), as well as in non-linear optics applications.
• OLED organic electroluminescent device
• O IC organic integrated circuit
• OF-FET organic field effect transistor
• OF-TFT organic thin film transistor
• O-LET organic light emitting transistor
• O-SC organic solar cell
• O-SC organic optical detector
• O-FQD organic field que
• light refers to visible light, i.e., electromagnetic radiation in the wavelength range of 350 to 780 nm.
• a “light absorber” is a compound that can absorb light in at least a portion of that wavelength range.
• NIR near infrared
• NIR absorber is a compound that absorbs radiation in at least a portion of this wavelength range can.
• the invention also relates to optoelectronic components, such as those mentioned above, which contain at least one of the compounds as defined above.
• the compounds of the invention are compounds of general structural formula (I).
• the definitions already given above apply.
• the part of the molecule which is active as electron donor (D) is formed from the block of R 1 , R 2 , the aromatic including the variables Y, Y 1 , Y 2 , Z, Z 1 and Z 2 and the quinoid part X together, and the part of the molecule acting as electron acceptor (A) from the cyano end group and the variable A together.
• variables Y, Y 1 , Y 2 , Z, Z 1 , Z 2 and X are each bivalent groups.
• the term "bivalent" means that the respective groups are each bonded to the remainder of the molecule according to formula (I) via two molecular atoms, which means that, for example, if X is defined as a benzoquinoid substituent, the benzoquinoid substituent is bivalent such that it is coupled to the rest of the molecule via the two double bonds of formula (I) or (II).
• an aryl group within the meaning of this invention contains from 6 to 60 aromatic ring atoms and a heteroaryl group within the meaning of this invention contains from 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
• an aryl group or heteroaryl group is either a monocyclic aromatic group, such as e.g. Phenyl, or a monocyclic heteroaromatic group, for example pyridinyl, pyrimidinyl or thienyl, or a fused (fused) aromatic or heteroaromatic polycyclic group, for example naphthalenyl, phenanthrenyl or carbazolyl.
• a condensed (fused) aromatic or heteroaromatic polycycle consists of two or more simple aromatic or heteroaromatic rings condensed together.
• an Aryi (Ar) group which may be substituted in each case with further radicals, in particular groups understood, which are selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyrenyl, dihydropyrenyl, Chrysenyl, perylenyl, fluoranthenyl, benzanthracenyl, benzphenanthrenyl, tetracenyi, pentacenyl and benzpyrenyl, wherein the above groups may each be substituted or unsubstituted, wherein the substituents for example, be selected from substituted or unsubstituted straight-chain alkyl, Aikoxy- or thioalkyl groups having 1 to 20 carbon atoms or substituted or unsubstituted, branched or cyclic alkyl, Aikoxy- or thioalkyl groups having 3 to 20
• substituents of the aryl groups are in turn substituted, their substituents are selected from straight-chain alkyl, Aikoxy- or thioalkyl groups having 1 to 20 carbon atoms, cyclic or branched alkyl, Aikoxy- or thioalkyl groups having 3 to 20 C. -Atomen, alkenyl or Aikinyl phenomenon having 2 to 20 carbon atoms, carboxyl, hydroxyl, thiol, amino, or nitrile groups, unsubstituted aryl or heteroaryl groups, as defined below, and halogens, especially F and Cl.
• a heteroaryl (HetAr) group which may be substituted in each case with further radicals and which may be linked via an arbitrary position on the aromatic, in particular means a group which is selected from the group consisting of furanyl, Difuranyl, terfuranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, dithienyl, terthienyl, benzothienyl, isobenzothienyl, benzodithienyl, benzotrithienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, Benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenothiaziny
• quinoid is understood to mean a structural motif which, while abolishing the aromaticity, of aromatic analogues Derives structures, wherein the quinoid structure motif represents a mesomeric boundary structure of the analogous aromatic structure and forms a conjugated double bond system.
• variable X denotes a quinoid aromatic, a quinoid polyaromatic, a quinoid heteroaromatic or a quinonoid polyheterroate.
• the chionoid structural motif X is a bivalent substituent, which means that the quinoid structural motif X has in each case one carbon double bond to the rest of the acceptor moiety A and to the donor moiety consisting of the cyano end group and the Variables A is bound.
• the quinoid aromatics include, for example, benzoquinone, naphthaquinone, anthraquinone, fluorenoquinone, and other benzoquinone-derived fused structural motifs, wherein the above groups may each be substituted or unsubstituted.
• the substituents are preferably selected from the above-described substituents described in connection with the aryl groups.
• Chinoid polyaromatics are to be understood as meaning those structural motifs which are composed of the exemplified quinoid aromatics such that two or more quinoid aromatics are connected to one another via a carbon double bond, so that a conjugated ⁇ electron system is present.
• the two or more quinoid aromatics which make up the quinoidal polyaromatic according to the present invention may be selected independently of one another, for example from the group consisting of benzoquinone, naphthaquinone, anthraquinone, fluorenquinone and other benzoquinone-derived fused-on structural motifs each of the above groups may be substituted or unsubstituted. When substituted, the substituents are preferably selected from the above-described substituents described in connection with the aryl groups.
• the quinoid heteroaromatics include, for example, the quinoid forms of thiophene, thienothiophene, dithienothiophene, furan, furofuran, difurofuran, pyridine, pyrrole, pyrrolopyrrole, dipyrrolopyrrole motifs, and also benzoquinone, naphthaquinone, anthraquinone, Fluorenquinone and other benzoquinone derived fused structural motifs containing at least one heteroatom, preferably selected from O, S and N.
• the said quinoid heteroaromatics may also be substituted or unsubstituted. When substituted, the substituents are preferably selected from substituents described above, which have been described in connection with the Aryi jury selected.
• Chinoid polyheteroaromatics are to be understood as meaning those structural motifs which are composed of the exemplified quinoid heteroaromatics such that two or more quinoid heteroaromatics are connected to one another via a carbon double bond, so that a conjugated ⁇ electron system is present.
• the two or more quinoid heteroaromatics which make up the quinoid polyheteroaromatic for the purposes of the present invention may be selected independently of one another, for example from the group consisting of the quinolines of thiophene, thienothiophene, dithienothiophene, bithienyl, trithienyl .Furan, furofuran, difurofuran, pyridine, pyrrole, pyrrolopyrrole, dipyrrolopyrrole motifs, as well as benzoquinone, naphthaquinone, anthraquinone, fluorenoquinone and other, derived from benzoquinone, annellated structural motifs, wherein the above groups are each substituted or unsubstituted could be.
• the substituents are preferably selected from the above-described substituents described in connection with the aryl groups.
• Y and Z are each independently S or NR 3 ;
• X is a quinoid heteroaromatic radical selected from substituted or unsubstituted quinoid thiophene, thienothiophene or dithienothiophene, or a quinoid aromatic selected from substituted or unsubstituted benzoquinone, naphthaquinone, anthraquinone or fluorenquinone;
• R 1 and R 2 are each independently selected from hydrogen, methyl, ethyl, n-propyl, c-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl - (amyl), 2-pentyl (sec-pentyl), 3-pentyl, 2-methylbutyl, 3-methylbutyl (iso-pentyl), 3-methylbut-2-yl, 2-methylbut 2-methylbut 2-methylbut 2-methylbut 2-methylbut 2-
• Y, Y 1 , Y 2 , Z, Z 1 and Z 2 are each independently O, S or NR 3 ;
• X is a quinoid heteroaromatic radical selected from substituted or unsubstituted quinoid thiophene, thienothiophene or dithienothiophene, or a quinoid aromatic selected from substituted or unsubstituted benzoquinone, naphthaquinone, anthraquinone or fluorenquinone; are R !
• R 2 are each independently selected from hydrogen, methyl, ethyl, n-propyl, c-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl (amyl -), 2-pentyi (sec-pentyl), 3-pentyl, 2-methylbutyl, 3-methylbutyl (iso-pentyl), 3-methylbut-2-yi, 2-methylbut-2 yl, 2,2-Dimethyipropyl- (neo-pentyl), n-hexyl or c-hexyl groups, and their alkoxy and thioalkyl, substituted or unsubstituted benzyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, or R 1 and R 2 together form a substituted or unsubstituted benzyl, naphthyl or an
• Y and Z are each S;
• R 1 and R 2 are each independently hydrogen, methyl, ethyl, n-butyl, n-hexyl, benzyl or para-methyl benzyl, or R 1 and R 2 together are benzyl, 4,5-dimethyl benzyl, 4,5-dimethoxybenzyl, 4, 5-di-n-butylbenzyl, 4, 5-di-n-hexylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• X is quinoid dithienothiophene or 3,5-dimethyldithienothiophene; and
• A is CN.
• Et is ethyl
• Prop is propyl, especially n-propyl
• But is butyl, especially n-butyl
• Hex is hexyl, especially n-hexyl
• hept is heptyl , in particular n-heptyl
• Oct for octyl, in particular n-octyl
• Non for nonyl, in particular n-nonyl.
• Y is NR 3 and Z is S
• R and R 2 are each independently hydrogen, methyl, ethyl, n-butyl, n-hexyl, benzyl or para-methylbenzyl, or R 1 and R 2 together are benzyl, 4, 5-dimethylbenzyl -, 4,5-dimethoxybenzyl, 4, 5-di-n-butyl benzyl, 4, 5-di-n-hexyi benzyl, naphthylene or 5,6-Dimethylnaphthylring form;
• X is quinoid dithienothiophene or 3,5-dimethyldithienothiophene;
• a CN is; and R 3 is a methyl, ethyl, n-butyl or n-hexyl group.
• Y and Z are each independently O, S or NR 3 ;
• R 1 and R 2 are each independently hydrogen, methyl, ethyl, isopropyl, n-butyl, n-hexyl, benzyl or para-methylbenzyl, or R 1 and R 2 together are benzyl, 4 , 5-dimethylbenzyl, 4,5-dimethoxybenzyl, 4, 5-diethylbenzyl, 4, 5-di-propylbenzyl, 4, 5-di-n-butylbenzyl, 4, 5-di- n-hexyi benzyl, 3,4,5,6-tetramethylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• X quinoides benzene, thienothiophene, dimethyl thienothiophene, dithienothiophene, 3,5-dimethy
• Y and Z are each S;
• R 1 and R 2 are each independently hydrogen, methyl, ethyl, n-butyl, n-hexyl, benzyl or para-methyl benzyl, or R 1 and R 2 together are benzyl, 4,5-dimethyl benzyl-, 4,5- Dimethoxybenzyl, 4,5-di-n-butylbenzyl, 4,5-di-n-hexylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• X fluoroquinone or 9-dimethylfluorenquinone; and
• A is CN.
• Y and Z are each NR 3 ;
• R 1 and R 2 are each independently hydrogen, methyl, ethyl, n-butyl, n-hexyl, benzyl or para-methylbenzyl, or R 1 and R 2 together are benzyl, 4,5-dimethyl benzyl, 4,5-dimethoxybenzyl, 4,5-di-n-butylbenzyl, 4,5-di-n-hexylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• X fluoroquinone or 9-dimethylfluorenquinone;
• a CN is; and R 3 with each occurrence is independently a methyl, ethyl, n-butyl or n-hexyl group.
• Y and Z are each independently S or NR 3 ;
• R 1 and R 2 are each independently of one another hydrogen, a methyl, ethyl, n-butyl, n-hexyl, benzyl, para-methylbenzyl or tobolyl group, or R 1 and R 2 together form a benzyl, 4 , 5-dimethylbenzyl, 4,5-dimethoxybenzyl, 4, 5-di-n-butylbenzyl, 4,5-di-n-hexylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• X quinoides N-methylcarbazole, N-isopropylcarbazole, fluorene quinone or 9-dimethylfluorenequinone;
• a CN is; and
• R 3 is a methyl, ethyl, n-butyl or n
• Y and Z are each independently S, O or NR 3 ;
• R 1 and R 2 are each independently hydrogen, a methyl, ethyl or Methylthio group, or R 1 and R 2 together form a benzyl, 4-methylbenzyl or 4,5-dimethyl benzyl ring or a 2,3-dihydrodithiine residue;
• X quinoides bithiophene, trithiophene, 3,4-dimethyl-2,2'-bithienyl, 3-methyl-2,2'-bithienyl, 4-ethyl-2,2'-bithienyl, 3-methyl-2- (3- pyridyl) thiophene, 4-propyl-2- (3-pyridyl) thiophene, 3,4-dimethyl-2- (3-pyridyl) thiophene or 3,4-dibutyl-2- (3-pyri
• Y and Z are each independently S or NR 3 ;
• R 1 and R 2 are each independently of one another hydrogen, a methyl, ethyl, n-butyl, n-hexyl, benzyl, para-methylbenzyl or tobolyl group, or R 1 and R 2 together form a benzyl, 4 , 5-dimethylbenzyl, 4,5-dimethoxybenzyl, 4, 5-di-n-butylbenzyl, 4, 5-di-n-hexylbenzyl, naphthyl or 5,6-dimethylnaphthyl ring;
• Y 1 , Y 2 , Z 1 and Z 2 are each S;
• X is chinoides thiophene, 3,4-dimethylthiophene, 3,4-diethylthiophene, 3,4-difluorothiophene, dithienothioph
• the present invention moreover relates to the use of at least one compound of the formula (I) or (II) in an optoelectronic component.
• the optoelectronic device is OSCs having a photoactive organic layer.
• This photoactive layer includes low molecular weight compounds, oligomers, polymers or mixtures thereof as organic coating materials.
• a preferably opaque or semitransparent electrode is applied as the cover contact layer.
• the optoelectronic component is arranged on a flexibly designed substrate.
• a flexible substrate is understood to be a substrate which ensures deformability as a result of external forces. As a result, such flexible substrates are also suitable for mounting on curved surfaces.
• Flexible substrates include, but are not limited to, plastic or metal foils.
• the coating is carried out for producing an optoelectronic component by means of vacuum processing of organic compounds according to the invention, so that advantageously can be dispensed for the production of optoelectronic device high temperature steps above 160 ° C, preferably the deposition at substrate temperatures below 90 ° C, more preferably at below 30 ° C.
• the compounds used according to the invention for producing the optoelectronic component have a low evaporation temperature, preferably ⁇ 300 ° C., particularly preferably ⁇ 250 ° C. In various embodiments, however, the evaporation temperature is at least 120 ° C. It is particularly advantageous if the organic compounds according to the invention are sublimable in a high vacuum.
• the coating for producing an optoelectronic component takes place by means of solvent processing of the compounds described herein. Due to the availability of commercial spray robots, this application method can advantageously be easily scaled to industrial roll-to-roll standards.
• the optoelectronic component in the sense of the present invention is a generic solar cell.
• Such an optoelectronic component usually has a layer structure, wherein the respectively lowest and uppermost layer are formed as an electrode and counter electrode for electrical contacting.
• the optoelectronic component is arranged on a substrate, such as, for example, glass, plastic (PET, etc.) or a metal strip.
• At least one organic layer comprising at least one organic compound is arranged between the substrate-near electrode and the counterelectrode.
• organic compound here are organic low molecular weight compounds, oligomers, Polymers or mixtures are used.
• the organic layer is a photoactive layer.
• the optoelectronic component is designed as a tandem or multiple component. In this case, at least two optoelectronic components are deposited as a layer system one above the other.
• additional layers for coating or encapsulating the component or other components may be connected to or under the contact and base layers.
• the organic layer is formed as one or more thin layers of vacuum-processed low molecular weight compounds or organic polymers.
• vacuum-processed low molecular compounds and polymers based optoelectronic devices are known in the art (Walzer et al., Chemical reviews 2007, 107 (4), 1233-1271, Peumans et al., J. Appl. Phys , 93 (7), 3693-3722).
• the organic layer is deposited on a substrate using vacuum processable compounds of the inventive compounds described herein.
• the organic layer is wet-chemically deposited on a substrate using solutions.
• the compound of the invention is selected from the group consisting of compounds 1a-1h, 2a-2j, 3a-3h, 4a-4l, 5a-5n, 6a-6l, 7a-7p, 8a-8h, 9a-9zz, 10a-10s, 1 1a-1 1 r, 12a-12p, 16a-16t as defined above.
• the optoelectronic component is an organic solar cell (OSC).
• OSC organic solar cell
• the organic layer is a light-absorbing layer, wherein the compound according to the invention acts as a light absorber.
• ITO indium-tin-oxide
• PET Polyethylene terephthalate
• the organic layer comprises at least one compound of the general formula (I) and / or (II) as described herein, and optionally another low molecular weight compound, an oligomer and / or a polymer of a donor and an acceptor compound, or a layer sequence of Donor and acceptor compounds. There may be more intermediate layers.
• the at least one active layer of the optoelectronic component absorbs the widest possible spectral range of the incident light.
• the electrodes of the optoelectronic component consist of metal, a conductive oxide, in particular ITO, ZnO: Al or another TCO (Transparent Conductive Oxide) or a conductive polymer, in particular PEDOT / PSS (poly (3,4-) ethylenedioxythiophene) poly (styrenesulfonate)) or PANI (polyaniline).
• the electrode which is arranged on the substrate is translucent for light or at least transparent in a certain light wavelength range. Translucency refers to the partial translucency of a material, so that the respective material for light has a transmittance of at most 100% and at least 1%, at least in a certain range of light wavelengths.
• the optoelectronic component is translucent at least in a certain range of light wavelengths for light.
• compounds of the invention as described herein are used as light absorbers in combination with electron acceptors, such as fullerenes, preferably C60 or C70 fullerenes, and fullerene derivatives such as 1- (3-methoxycarbonyl) propyl-1-1- Phenyl (6,6) C61 (PCBM) used as so-called photoactive mixed layers in optoelectronic devices.
• electron acceptors such as fullerenes, preferably C60 or C70 fullerenes
• fullerene derivatives such as 1- (3-methoxycarbonyl) propyl-1-1- Phenyl (6,6) C61 (PCBM) used as so-called photoactive mixed layers in optoelectronic devices.
• electrons are advantageously transferred from the compound according to the invention to the electron acceptor, which then can usually reach the electrode via a thin electron transport layer.
• Organic solar cells may also include two or more photoactive layers (multi-junction devices), wherein the two photoactive layers are usually housed in individual mostly directly vertically stacked solar cells are connected in series via a so-called recombination, which has already been implemented in different versions.
• photoactive layers multi-junction devices
• the materials are processed from solution and thus a further applied layer very easily leads to the underlying layers being dissolved, dissolved or their morphology changed.
• polymer-based organic solar cells therefore, only a very limited number of multilayer systems can be produced and only by using different material and solvent systems which do not or hardly influence each other during production.
• a multilayer solar cell consists for example of a structure as shown in Figure 1 (in the example shown, a so-called tandem solar cell with two photoactive layers compared to a single cell). After the first subcell (counted from the substrate), the layer stack is continued directly with the hole- or electron-conducting layer (depending on the design as a pin or nip structure), and the cover contact is applied only after the complete second subcell. The combination of electron and hole-guiding layer in the middle between the two single cells is called recombination contact.
• complementary absorber layers each consisting of an electron donor and a suitable acceptor material, of which one or more of these materials comprise the compounds of general formula (I) and / or (II) described herein, are used for the two photoactive layers.
• Complementary in this case means that the absorption bands of the absorber molecules overlap only slightly or not at all.
• a larger area of the solar spectrum can be used for power generation.
• a multi-junction solar cell can also be made with identical materials in the photoactive layers of two or more subcells.
• the donor material in one or more subcells may each consist of one or more compounds according to the invention.
• the aforementioned multi-junction solar cells can be implemented as a parallel-connected cell-without fundamental changes in the mode of operation of the component.
• the compounds according to the invention are used as light absorbers in so-called cascade structures.
• the photoactive layer of a solar cell described above consists of a sequence of several donor molecules followed by several acceptor molecules (depending on the design as a pin or nip structure in reverse order).
• multiple donors may also be mixed with multiple acceptors to form the photoactive layer, thereby covering a wider spectral range of sunlight.
• the compounds of the invention can also be used as electron acceptor molecules.
• the compounds of the invention as described herein also find use as IR absorbers as well as in NLO (non-linear optics) applications.
• Synthesis Example 13 2 - ((2E, 5'E) -5 '- (5-Methylbenzo [d] [1'-dithiol] -ylidene-SH.S'Hp ⁇ ' - bithiophenylidenes] -5-ylidene) malononitrile
• the preparation is analogous to Synthesis Example 6, starting from 5-methyl-2- (methylthio) - benzo [d] [1, 3] dithiol-1-ium-tetrafluoroborat.
• Exemplary solar cells First solar cells using representatives of the above materials as absorbers with electron donating properties were prepared. An optimization is still pending.
• the absorption spectrum of the compound 24 (2- (5- (4,5-bis (methylthio) -1,3-dithiol-2-ylidene) thiophene-2 (5H) -ylidene) -malononitrile shown in the first Synthesis Example has a strong absorption in the visible range, the strong vibration bands indicate a good molecular layer order, which should have a positive effect on the charge carrier transport.
• the test solar cell 1 an example of a volume-heterojunction solar cell in which the above-mentioned compound 24 of Synthetic Example 1 is used as a donor is shown. In addition to a high open terminal voltage, this example has an extremely high short-circuit current density for an unoptimized cell. The external quantum efficiency is over 50% at maximum.
• compound 16a exhibits unique absorption behavior in a very broad range from 500 to 1000 nm, covering a wide range of solar spectrum down to the most neglected infrared range.
• Compound 16a was also tested in a test structural solar cell and also achieved a high photocurrent and for a infrared absorber a high voltage of 0.39V.

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