CHEMICAL COMPOUND, USE OF AT LEAST SUCH A CHEMICAL COMPOUND IN AN OPTOELECTRONIC COMPONENT, AND OPTOELECTRONIC COMPONENT WITH AT LEAST SUCH A CHEMICAL COMPOUND

Description

[0001] The present invention relates to a chemical compound of general formula I, the use of at least one such compound in an optoelectronic device, and an optoelectronic device with at least one such compound.

[0002] Organic electronics utilizes circuits made of electrically conductive polymers or small organic molecules. Organic semiconductors can perform various functions in an electronic component, such as charge transport, radiation absorption, or radiation emission, with one or more functions being fulfilled simultaneously. Optoelectronic components can include displays, data storage devices, or transistors, but also organic optoelectronic components, such as photovoltaic elements, especially solar cells, and photodetectors, which have a photoactive layer in which charge carriers, particularly bound electron-hole pairs (excitons), are generated upon exposure to electromagnetic radiation. The excitons reach such an interface by diffusion, where electrons and holes are separated.The material that accepts the electrons is called the acceptor, and the material that accepts the holes is called the donor.

[0003] Organic optoelectronic devices enable the conversion of electromagnetic radiation into electric current by utilizing the photoelectric effect. Such conversion of electromagnetic radiation requires absorber materials that exhibit good absorption properties.

[0004] Organic optoelectronic devices are known from the prior art. WO2004083958A2 discloses a photoactive device, in particular a solar cell, consisting of organic layers of one or more stacked pi-, ni- and / or pin-diodes.

[0005] A known prior art design for an organic solar cell consists of a pin or nip diode (Martin Pfeiffer, "Controlled doping of organic vacuum deposited dye layers: basics and applications", PhD thesis TU-Dresden, 1999, and WO2011 / 161108A1). A pin solar cell comprises a substrate with a usually transparent electrode, p-layer(s), i-layer(s), n-layer(s), and a counter electrode. Here, n and p denote n- or p-doping, which leads to an increase in the density of free electrons or holes, respectively, in thermal equilibrium. Such layers are primarily understood as transport layers. The term i-layer refers to an undoped layer (intrinsic layer) with an absorber material or a mixture of several absorber materials. One or more i-layers can consist of a mixture of two or more materials (bulk heterojunctions).An absorber material, or absorber, is understood to be a compound that absorbs light in a specific wavelength range. Accordingly, an absorber layer is understood to be a layer in an optoelectronic component that contains at least one absorber material.

[0006] Numerous polymeric and non-polymeric absorber materials for organic photovoltaic elements in the red and near-infrared (NIR) range between approximately 600 and 1400 nm are known from the prior art. Among non-polymeric absorber materials, those of the BODIPY class have proven particularly suitable for the near-infrared spectral range. In particular, the use of meso-CF3-substituted derivatives has proven effective, enabling the achievement of suitable energy levels and thus high photovoltages combined with long-wavelength absorption ranges.

[0007] WO 2015 036 529 A1 discloses the use of a pyrrolopyrrole-based compound in an organic electronics device.

[0008] WO 2010 133 208 A1 discloses an organic semiconductor comprising several layers, wherein at least one of the layers comprises a material with an azabodipy backbone.

[0009] Umezawa et al. (J. Am. Chem. Soc. 2008, 130, 5, 1550-1551) discloses BODIPY structures as fluorescent dyes that are unsubstituted in the meso position or bear a fluorinated alkyl chain.

[0010] Li et al. (Boron dipyrromethene (BODIPY) with meso-perfluorinated alkyl substituents as near infrared donors in organic solar cells, J. Mater. Chem. A, 2018, 6, 18583-18591) discloses BODIPY structures that carry perfluorinated alkyl chains in the meso position and can be used as NIR donor materials in organic solar cells.

[0011] Shimogawa et al. (Chem. Lett. 2013, 42, 986-988) revealed the influence of dibenzo- and dithieno-fused structures at the β,γ bond in BODIPY frameworks. Electrochemical and photophysical measurements showed an effective increase in the electron-withdrawing effect of the BODIPY frameworks with a red-shifted absorption.

[0012] Chen et al. (J. Org. Chem. 2000, 65, 2900-2906) disclose modified 4,4-Difluoro-4-Bora-3a,4a-Diaza-s-Indacene (BODIPY) dyes with extended conjugation and restricted bond rotation.

[0013] WO2010104875 A1 reveals connection BDF-NIR1.

[0014] The absorbers known from the prior art in the red and near-infrared range are unsatisfactory. While the known absorber materials are suitable for photoactive layers in organic photovoltaic elements, i.e., organic solar cells, their absorption properties need to be improved, particularly to make organic photovoltaic elements competitive with conventional silicon-based solar cells. The efficiency of an organic photovoltaic element depends, among other things, on the absorption behavior of the organic materials, i.e., the absorber materials, in the photoactive layer. Furthermore, a fundamental problem in vacuum processing is the limited vaporizability of organic materials, as their thermal stability is insufficient for evaporation in a vacuum, thus severely restricting the choice of absorbers.Low melting and decomposition points limit the evaporability and thus the achievable deposition rate, meaning that many materials that are in principle suitable as absorbers cannot be used on an industrial scale.

[0015] The invention is therefore based on the objective of providing chemical compounds, the use of at least one such chemical compound in an optoelectronic device, and an optoelectronic device with at least one such compound, wherein the aforementioned disadvantages do not occur, and wherein the chemical compounds in particular have improved absorption properties and at the same time exhibit improved evaporability, i.e., high melting and decomposition points, in particular low evaporation temperatures without decomposing.

[0016] The problem is solved by the subject matter of the independent claims. Advantageous embodiments arise from the dependent claims.

[0017] The problem is solved in particular by a chemical compound of the general formula I, where X1 and X2 independently O, S or N-R8 are R8 selected from the group consisting of H, alkyl, aryl and heteroaryl, preferably R8 selected from the group consisting of H, alkyl, and aryl, R1 being a substituted homocyclic 6-ring, wherein at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR8 with R8 C1-C4-alkyl, or is a substituted or unsubstituted heterocyclic 5-ring or 6-ring, wherein the heterocyclic 5-ring or 6-ring has at least one sp2-hybridized N atom with a lone pair of electrons and / or has at least one heteroatom selected from O, S, or N, wherein at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR9 with R9 C1-C4 alkyl is substituted, R2 and R7 are independently selected from the group consisting of H, halogen, CN, alkyl,fluorinated or partially fluorinated alkyl, and unsaturated alkyl, R4 and R5 are independently selected from the group consisting of H, halogen, CN, alkyl, fluorinated or partially fluorinated alkyl, unsaturated alkyl, and alkoxy, and R3 and R6 are independently selected from the group consisting of H, halogen, CN, alkyl, fluorinated or partially fluorinated alkyl, unsaturated alkyl, and alkoxy, and R3 and R6 are independently selected from the group consisting of R3 and R6, respectively, a substituted or unsubstituted homocyclic 6-membered ring or a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring.

[0018] According to the invention, compounds of general formula I are BODIPY dyes, which preferably have a 5- or 6-membered heteroaryl ring, or a 6-membered aryl ring with at least one substituent selected from the group consisting of Cl, CN, and F, in the meso position of the BODIPY backbone. Preferably, the pyrrole rings of the BODIPY backbone are fused to a further cyclic system.

[0019] Substitution is understood to mean, in particular, the replacement of H by a substituent. A substituent is understood to be, in particular, any atom or group of atoms other than hydrogen, preferably a halogen, an alkyl group (the alkyl group may be linear or branched), an alkenyl group, an alkynyl group, an amino group, an alkoxy group, a thioalkoxy group, an aryl group, or a heteroaryl group. A halogen is understood to be, in particular, F, Cl, or Br, preferably F.

[0020] A heteroatom, in particular a heteroatom in the general formula I, is understood to be, in particular, an atom selected from the group consisting of O, S, Se, Si, B, N or P, preferably selected from the group consisting of O, S, Se or N.

[0021] The chemical compounds of general formula I according to the invention offer advantages compared to the prior art. Advantageously, improved absorbers for optoelectronic components can be provided. Advantageously, absorber materials for the red and near-infrared spectral range with high absorption strength and particularly good vaporizability are provided. Advantageously, compounds of general formula I absorb red and near-infrared light in a wavelength range of 600 to 1000 nm. Advantageously, the filling factors FF are particularly high. Advantageously, the compounds according to the invention are better suited for vacuum processing for the formation of photovoltaic cells. Advantageously, the vaporizability is increased, in particular the vaporizability without decomposition, and the compounds are thermally stable at a temperature of 300°C or higher.This allows the compounds to be processed in a vacuum without decomposition. Surprisingly, it was found that by using an at least partially fluorinated aryl substituent instead of an at least partially fluorinated alkyl chain, a significantly higher melting and decomposition point can be achieved, while the evaporation temperature increases only slightly. Advantageously, the color variability of organic photovoltaic cells can be increased. Advantageously, the absorption of light in the visible range below 650 nm is relatively low, which is why the compounds according to the invention are very well suited for the production of semi-transparent or transparent organic solar cells or photodetectors.

[0022] According to a further development of the invention, X1 and X2 are S or X1 and X2 are O, and / or wherein at least one H atom in the homocyclic 6-ring and / or in the heterocyclic 5-ring or 6-ring R1 is substituted by F or CF3, preferably by F. This allows the advantageous effects of the present invention to be realized in a special way.

[0023] In a preferred embodiment of the invention, R3 and / or R6 is a homocyclic 6-ring, wherein at least one H atom is substituted by an alkyl group, an alkoxy group and / or an F atom.

[0024] According to a further development of the invention, R3 and R4 and / or R5 and R6 each together form a heterocyclic 5-membered or 6-membered ring with at least one heteroatom selected from O, S, or N, preferably O or S, wherein the heterocyclic 5-membered or 6-membered ring is preferably unsubstituted, or form a homocyclic 6-membered ring. This allows the advantageous effects of the present invention to be realized in a particularly effective manner.

[0025] In a preferred embodiment of the invention, R3 and R4 and / or R5 and R6 do not together form a heterocyclic 5-ring or 6-ring.

[0026] In a preferred embodiment of the invention, X1 and R6, preferably R8 and R6, and / or X2 and R3, preferably R8 and R3, together form a heterocyclic five-membered ring or six-membered ring with at least one heteroatom selected from the group consisting of S, O and N, or a homocyclic six-membered ring, preferably a heterocyclic five-membered ring.

[0027] In a preferred embodiment of the invention, X1 and R7, preferably R8 and R7, and / or X2 and R2, preferably R8 and R2, together form a heterocyclic five-membered ring or six-membered ring with at least one heteroatom selected from the group consisting of O, S and N, or a homocyclic six-membered ring, preferably a heterocyclic five-membered ring.

[0028] According to a further development of the invention, R1 is a homocyclic 6-ring with the condition R1 equal to C 6 H n F 5-n with n=0,1,2,3,4. This allows the advantageous effects of the present invention to be realized in a particularly advantageous way.

[0029] According to a further development of the invention, it is provided that R1 is selected from the group consisting of: where * denotes the connection to the compound of general formula I, where Y is independently selected from the group consisting of Cl, CN, F and CF3, preferably YF, and where H atoms are substituted or unsubstituted, preferably unsubstituted. This allows the advantageous effects of the present invention to be realized in a special way.

[0030] According to a further development of the invention, it is provided that R3 and R6 are selected independently of each other from the group consisting of where * denotes the linkage to the compound of general formula I, where U is selected from the group consisting of O, S and NR19, where R19 is selected from the group consisting of H, halogen, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, alkenyl, aryl, and heteroaryl, preferably UO or S, and where Z is independently selected from the group consisting of H, halogen, preferably F, CF3, CN, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkenyl, alkoxy, N-alkyl, NAlkyl2, aryl, and heteroaryl, where preferably R3 and R6 are the same. This allows the advantageous effects of the present invention to be realized in a special way.

[0031] In a preferred embodiment of the invention, Z is independently selected from the group consisting of halogen, preferably F, CF3, and CN, with Z being particularly preferred. In an alternatively preferred embodiment of the invention, Z is methyl, methoxy, ethyl, or ethoxy.

[0032] In a preferred embodiment of the invention, R3 and R6 are selected independently of each other from where * denotes the linkage to the compound of general formula I, Z2 is selected from the group consisting of O, S, and N-R11, wherein R11 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl, Y3 is N or C-R12, wherein R12 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, wherein preferably at least one H is substituted, preferably by CN or F, Y4 is N or C-R13, wherein R13 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, wherein preferably at least one H is substituted, preferably by CN or F, and wherein preferably R12 and R13 are combined with each other in the form are homocyclic or heterocyclic in a ring structure, and R10 is selected from the group consisting of H, halogen,Alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, heteroaryl, alkenyl, and an electron-withdrawing alkyl group with at least one C=C double bond, wherein preferably at least one H is substituted by CN or F.

[0033] In a preferred embodiment of the invention, the H atoms in Y3 and / or Y4 are at least partially substituted by alkyl, alkoxy or F.

[0034] In a preferred embodiment, positions Y3 and Y4 are CH.

[0035] In a preferred embodiment of the invention, group R3 is the same as group R6.

[0036] In a preferred embodiment of the invention, X1 equals X2, R2 equals R7, R4 equals R5, and R3 equals R6.

[0037] In a preferred embodiment of the invention, X1 and X2 are equal to O or S, R2 and R7 are H, R4 and R5 are H, and R3 is equal to R6.

[0038] According to a further development of the invention, it is provided that R3 and / or R6 are further annealed, and / or R1 is a monocyclic 5-ring or 6-ring.

[0039] In a preferred embodiment of the invention, R3 and / or R6 is annealed with at least one further 5-ring or 6-ring, preferably with two further 5-rings and / or 6-rings, wherein the at least one 5-ring and / or the at least one 6-ring is a substituted or unsubstituted aryl or heteroaryl ring.

[0040] In an alternative preferred embodiment of the invention, R3 and / or R6 are not further annealed.

[0041] According to a further development of the invention, it is provided that R2 and R7 are independently selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R2 and R7 are H, and / or R4 and R5 are independently selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R4 and R5 are H.

[0042] According to a further development of the invention, R1 is a heterocyclic 5-ring or 6-ring with at least one sp2-hybridized N atom with a lone pair of electrons in the ring system, preferably R1 is selected from the group consisting of substituted or unsubstituted imidazole, pyrazole, triazole, tetrazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, oxazole, isoxazole, thiazole, and isothiazole.

[0043] In a particularly preferred embodiment of the invention, R1 is not a substituted and / or not a non-substituted thiophene, preferably not a non-substituted thiophene.

[0044] In a particularly preferred embodiment of the invention, R1 is not a substituted and / or non-substituted furan, preferably not a non-substituted furan.

[0045] In a particularly preferred embodiment of the invention, R1 is not a substituted and / or non-substituted pyrrole, preferably not a non-substituted pyrrole.

[0046] In a preferred embodiment of the invention, the heterocyclic 5-ring or 6-ring, or the homocyclic 6-ring, is not further annealed.

[0047] According to a further development of the invention, the compound is selected from the group consisting of:

[0048] According to a further development of the invention, it is provided that all H atoms in R1 are substituted by a halogen, CF3 or CN, preferably all H atoms are substituted by F.

[0049] The compounds according to the invention relate in particular to so-called small molecules. Small molecules are understood to be, in particular, non-polymeric organic molecules with monodisperse molar masses between 100 and 2000 g / mol, which exist in a solid phase at normal pressure (atmospheric pressure) and at room temperature. In particular, the small molecules are photoactive, whereby photoactivity is understood to mean that the molecules change their charge state and / or their polarization state upon exposure to light. The photoactive molecules exhibit, in particular, absorption of electromagnetic radiation in a specific wavelength range, whereby the absorbed electromagnetic radiation, i.e., photons, are converted into excitons.

[0050] According to a further development of the invention, the compound is provided to have a molar weight of 300-1500 g / mol.

[0051] In a preferred embodiment of the invention, the compounds according to the invention do not have a ring structure between R3 and R4 and / or between R5 and R6.

[0052] In a preferred embodiment of the invention, the connection is formed in a mirror-symmetrical manner with respect to the axis through R1 and B.

[0053] The object of the present invention is also achieved by providing for the use of at least one compound according to the invention in an optoelectronic component, particularly according to one of the previously described embodiments. The use of the at least one compound in the optoelectronic component offers, in particular, the advantages already explained in connection with the compound according to the invention.

[0054] According to a further development of the invention, it is provided that the compound according to the invention is used in an organic optoelectronic device, preferably an organic solar cell, an OLED, an OFET, or an organic photodetector.

[0055] In a preferred embodiment of the invention, the at least one compound according to the invention is used as an absorber material in a photoactive layer of the optoelectronic device. In a preferred embodiment of the invention, the compound according to the invention is used as a donor in a donor-acceptor heterojunction.

[0056] The object of the present invention is also achieved by providing an optoelectronic component with a layer system, particularly according to one of the previously described embodiments, wherein at least one layer of the layer system comprises a compound according to the invention. In this case, at least one layer of the layer system comprises at least one compound according to the invention. This results in particular advantages for the optoelectronic component that have already been explained in connection with the compound according to the invention and the use of the at least one compound according to the invention in an optoelectronic component. The optoelectronic component comprises a first electrode, a second electrode, and a layer system, wherein the layer system is arranged between the first electrode and the second electrode.

[0057] According to a further development of the invention, the optoelectronic component is an organic optoelectronic component, preferably an organic solar cell, an OFET, an OLED or an organic photodetector.

[0058] According to a further development of the invention, the optoelectronic component is provided to have a layer system with at least one photoactive layer, preferably a light-absorbing photoactive layer, wherein the at least one photoactive layer comprises the at least one compound according to the invention.

[0059] In a preferred embodiment of the invention, the at least one photoactive layer is an absorber layer; preferably, the at least one compound is an absorber material.

[0060] In a preferred embodiment of the invention, the photoactive layer is arranged between the first electrode and the second electrode.

[0061] In a preferred embodiment of the invention, the layer system comprises at least two photoactive layers, preferably at least three photoactive layers, or preferably at least four photoactive layers.

[0062] An organic optoelectronic device is understood to be, in particular, a photovoltaic element with at least one organic photoactive layer, wherein the organic photoactive layer comprises at least one compound according to the invention. An organic photovoltaic element enables the conversion of electromagnetic radiation, especially in the wavelength range of visible light, into electric current by utilizing the photoelectric effect. In this sense, the term "photoactive" is understood as the conversion of light energy into electrical energy. In contrast to inorganic solar cells, free charge carriers are not directly generated by light in organic photovoltaic elements; instead, excitons, i.e., electrically neutral excitation states (bound electron-hole pairs), are formed first.Only in a second step are these excitons separated into free charge carriers in a photoactive donor-acceptor junction, which then contribute to the electric current flow.

[0063] In a preferred embodiment of the invention, the photoactive layer is formed as a mixed layer of at least one compound according to the invention and at least one further compound, or as a mixed layer of at least one compound according to the invention and at least two further compounds, wherein the compounds are preferably absorber materials.

[0064] In a preferred embodiment of the invention, the layer system of the optoelectronic component comprises at least one transport layer, wherein the at least one transport layer is doped, partially doped, or undoped. A transport layer is understood in particular to be a layer of a layer system that transports charge carriers of a certain type and preferably absorbs electromagnetic radiation largely only in a range of < 450 nm.

[0065] In a preferred embodiment of the invention, the optoelectronic component has a substrate, wherein the first electrode or the second electrode is arranged on the substrate, in particular one of the electrodes of the optoelectronic component can be applied directly to the substrate, wherein the layer system is arranged between the first electrode and the second electrode.

[0066] In a preferred embodiment of the invention, the compound and / or a layer containing the at least one compound is deposited by means of vacuum processing, gas phase deposition or solvent processing, in particular preferably by means of vacuum processing.

[0067] The invention will be explained in more detail below with reference to the drawings. The drawings show: Fig. 1 a schematic representation of an exemplary embodiment of an optoelectronic component in cross-section; Fig. 2 a graphical representation of the absorption spectrum of the compound (1); Fig. 3 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (1), measured on an organic optoelectronic device; Fig. 4 a graphical representation of the absorption spectrum of the compound (3); Fig. 5a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (3), measured on an organic optoelectronic device; Fig. 6 a graphical representation of the absorption spectrum of the compound (5); Fig. 7 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (5), measured on an organic optoelectronic device; Fig. 8 a graphical representation of the absorption spectrum of the compound (8); Fig. 9 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (8), measured on an organic optoelectronic device; Fig. 10 a graphical representation of the absorption spectrum of the compound (10); Fig. 11a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with the compound (10), measured on an organic optoelectronic device; Fig. 12 a graphical representation of the absorption spectrum of the compound (14); Fig. 13 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (14), measured on an organic optoelectronic device; Fig. 14 a graphical representation of the absorption spectrum of the compound (15); Fig. 15 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (15), measured on an organic optoelectronic device; Fig. 16 a graphical representation of the absorption spectrum of the compound (29); Fig. 17a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (29), measured on an organic optoelectronic device; Fig. 18 a graphical representation of the absorption spectrum of compound (32); and Fig. 19 a graphical representation of the current-voltage curve, the spectral external quantum yield and the fill factor of a BHJ cell with compound (32), measured on an organic optoelectronic device. Examples of implementation

[0068] Fig. 1 Figure 1 shows a schematic cross-sectional representation of an exemplary embodiment of an optoelectronic component. The optoelectronic component comprises at least one chemical compound of the general formula I.

[0069] The optoelectronic component according to the invention has a layer system 7, wherein at least one layer of the layer system 7 has a compound according to the invention.

[0070] In one embodiment of the invention, the optoelectronic component is an organic optoelectronic component, preferably an organic solar cell, an OFET, an OLED, or an organic photodetector. In this exemplary embodiment, the optoelectronic component is an organic solar cell.

[0071] The optoelectronic component comprises a first electrode 2, a second electrode 6, and a layer system 7, wherein the layer system 7 is arranged between the first electrode 2 and the second electrode 6. At least one layer of the layer system 7 has at least one connection according to the invention.

[0072] In a further embodiment of the invention, the optoelectronic component has a layer system 7 with at least one photoactive layer 4, preferably a light-absorbing photoactive layer 4, wherein the at least one photoactive layer 4 has the at least one compound according to the invention.

[0073] In a further embodiment of the invention, the layer system 7 has at least two photoactive layers 4, preferably at least three photoactive layers 4, or preferably at least four photoactive layers 4.

[0074] In one embodiment, the organic solar cell has a substrate 1, e.g., made of glass, on which an electrode 2 is located, comprising, for example, ITO. Arranged on this is the layer system 7 with an electron-transporting layer 3 (ETL) and a photoactive layer 4 with at least one compound according to the invention, a p-type donor material, and an n-type acceptor material, e.g., C60 fullerene, either as a flat heterojunction or as a bulk heterojunction. Above this is a p-doped hole transport layer 5 (HTL) and an electrode 6 made of gold or aluminum, configured as a bulk heterojunction.

[0075] In a further embodiment of the invention, the photoactive layer 4 is designed as a mixed layer of the at least one compound according to the invention and at least one further compound, or as a mixed layer of the at least one compound according to the invention and at least two further compounds, wherein the compounds are absorber materials.

[0076] In a further embodiment of the invention, the optoelectronic component is configured as a tandem cell, triple cell, or multiple cell. In this configuration, two or more photoactive layers 4 are stacked on top of each other, wherein the photoactive layers 4 are made of the same or different materials or material mixtures.

[0077] The individual components of a component according to the invention can be produced by evaporation in a vacuum, with or without a carrier gas, or by processing a solution or suspension, such as in coating or printing. Individual layers can also be applied by sputtering. This is particularly suitable for the base contact. The production of the layers by evaporation in a vacuum is advantageous, as the support substrate can be heated.

[0078] In a further embodiment of the invention, the optoelectronic component is a flexible optoelectronic component. For the purposes of the present invention, a flexible optoelectronic component is understood to be a component that is partially deformable as a result of an external force. This makes such flexible components suitable for placement on curved surfaces.

[0079] The general method for producing the compounds according to the invention is known to those skilled in the art from the prior art. In this context, particular reference is made to international applications WO2007126052A1 and EP3617214A1.

[0080] The chemical compound of general formula I has the following structure:

[0081] X1 and X2 are independently O, S or N-R8, with R8 selected from the group consisting of H, alkyl, aryl, and heteroaryl; R1 is a substituted homocyclic 6-ring, wherein at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR8 with R8 C1-C4 alkyl; or a substituted or unsubstituted heterocyclic 5-ring or 6-ring, wherein the heterocyclic 5-ring or 6-ring has at least one sp2-hybridized N atom with a lone pair of electrons and / or has at least one heteroatom selected from O, S, or N, wherein at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR9 with R9 C1-C4 alkyl. R2 and R7 are independently selected from the group consisting of H, halogen, CN, alkyl, fluorinated or partially fluorinated alkyl, and unsaturated alkyl.R4 and R5 are independently selected from the group consisting of H, halogen, CN, alkyl, fluorinated or partially fluorinated alkyl, unsaturated alkyl, and alkoxy. R3 and R6 are independently selected from the group consisting of a substituted or unsubstituted homocyclic 6-membered ring or a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring.

[0082] In one embodiment of the invention, X1 and X2 are S or X1 and X2 are O, and / or at least one H atom in the homocyclic 6-ring and / or in the heterocyclic 5-ring or 6-ring R1 is substituted by F or CF3, preferably by F.

[0083] In a further embodiment of the invention, R3 and R4 and / or R5 and R6 each together form a heterocyclic 5-ring or 6-ring with at least one heteroatom selected from O, S or N, preferably O or S, wherein preferably the heterocyclic 5-ring or 6-ring is not substituted, or form a homocyclic 6-ring.

[0084] In a further embodiment of the invention, R1 is a homocyclic 6-ring with the condition R1 equal to C 6 H n F 5-n with n=0,1,2,3,4.

[0085] In a further embodiment of the invention, R1 is selected from the group consisting of: where * denotes the connection to the compound of general formula I, where Y is independently selected from the group consisting of Cl, CN, F and CF3, preferably YF, and where H atoms are substituted or unsubstituted.

[0086] In a further embodiment of the invention, R3 and R6 are independently selected from the group consisting of where * denotes the linkage to the compound of general formula I, wherein U is selected from the group consisting of O, S and NR19, wherein R19 is selected from the group consisting of H, halogen, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, alkenyl, aryl, and heteroaryl, preferably UO or S, and wherein Z is independently selected from the group consisting of H, halogen, preferably F, CF3, CN, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkenyl, alkoxy, N-alkyl, NAlkyl2, aryl, and heteroaryl, wherein preferably R3 and R6 are the same.

[0087] In a further embodiment of the invention, R3 and / or R6 are further annealed, and / or R1 is a monocyclic 5-ring or 6-ring.

[0088] In a further embodiment of the invention, R2 and R7 are independently selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R2 and R7 are H, and / or R4 and R5 are independently selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R4 and R5 are H.

[0089] In a further embodiment of the invention, R1 is a heterocyclic 5-ring or 6-ring with at least one sp2-hybridized N atom with a lone pair of electrons in the ring system, preferably R1 is selected from the group consisting of substituted or unsubstituted imidazole, pyrazole, triazole, tetrazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, oxazole, isoxazole, thiazole, and isothiazole.

[0090] In a further embodiment of the invention, the compound is selected from the group consisting of:

[0091] In a further embodiment of the invention, all H atoms in R1 are substituted by a halogen or CN, preferably all H atoms are substituted by F.

[0092] In a further embodiment of the invention, the compound has a molar weight of 300-1500 g / mol.

[0093] The compound according to the invention is used in one embodiment of the invention in an optoelectronic device, preferably an organic optoelectronic device, in particular preferably an organic solar cell, an OLED, an OFET, or an organic photodetector.

[0094] Figures 2 to 21 below illustrate specific embodiments of the chemical compound according to the invention with the general formula I and its optical properties. The parameters open-circuit voltage Uoc, short-circuit current Jsc, and fill factor FF each refer to the same photovoltaic cell configuration.

[0095] Fig. 2 Figure 1 shows a graphical representation of the absorption spectrum of the compound (1).

[0096] The absorption spectra (optical density versus wavelength in nm) of compounds (1) to (32) were measured for 30 nm thick vacuum-deposited layers on quartz glass and in a solution of dichloromethane.

[0097] Fig. 3Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (1), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0098] The current-voltage curve contains key figures that characterize the organic solar cell. The most important of these are the fill factor FF, the open-circuit voltage Uoc, and the short-circuit current Jsc.

[0099] To investigate the compounds, specifically their use as absorber materials in organic optoelectronic devices, the current-voltage curve of a BHJ cell was measured. In this embodiment, the BHJ cell has a 15 nm thick layer of C60 on the ITO layer. Compound (1) was deposited onto this layer together with C60 at a thickness of 30 nm. This layer is followed by a 10 nm thick layer of BPAPF (9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene). This is followed by another 45 nm thick layer comprising BPAPF and NDP9. This is followed by another 1 nm thick layer of NDP9, and then a 50 nm thick gold layer.ITO serves as electrode 2, and the adjacent fullerene C60 as electron transport layer (ETL) 3. This is followed by the photoactive layer 4 with C60 as the electron acceptor material and the respective absorber, followed by BPAPF (9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene) as hole transport layer (HTL) 5 and BPAPF doped with NDP9 (Novaled AG), followed by a gold electrode 6. According to the invention, a semiconducting device contains at least one layer in a layer system of a compound of general formula I.

[0100] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (1) :C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF:NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined. The cell parameters were measured under AM1.5 illumination (AM = Air Mass; AM = 1.5 indicates that the global irradiance is < 1000 W / m² at this spectrum; AM = 1.5 is the standard value for measuring solar modules), where the photoactive layer comprises a bulk heterojunction (BHJ).

[0101] In the optoelectronic device with connection (1), the fill factor FF is 69.7%, the open-circuit voltage Uoc is 0.71 V, and the short-circuit current Jsc is 10.2 mA / cm². The cell efficiency of such an optoelectronic device, in particular a solar cell, with connection (1) is 5.05%.

[0102] Compound (1) exhibits good vaporizability in a vacuum. The vaporization temperature of compound (1) is 230°C, while the decomposition temperature is 377°C. In comparison, a corresponding reference compound (1), which has a CF3 group instead of a C6F5 group in the meso position of compound (1), shows a vaporization temperature of 215°C and a decomposition temperature 60°C lower, at 317°C.

[0103] Fig. 4 Figure 3 shows a graphical representation of the absorption spectrum of the compound.

[0104] Fig. 5 Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (3), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0105] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (3): C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (3), the fill factor FF is 73.4%, the open-circuit voltage Uoc is 0.69 V, and the short-circuit current Jsc is 11.4 mA / cm². The cell efficiency of such an optoelectronic device, particularly a solar cell, with Compound (3) is 5.77%.

[0106] Compound (3) exhibits good evaporability in a vacuum.

[0107] Fig. 6 Figure 5 shows a graphical representation of the absorption spectrum of the compound.

[0108] Fig. 7Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (5), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0109] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (5): C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (5), the fill factor FF is 71.7%, the open-circuit voltage Uoc is 0.95 V, and the short-circuit current Jsc is 9.4 mA / cm². The cell efficiency of such an optoelectronic device, particularly a solar cell, with Compound (5) is 6.40%.

[0110] Fig. 8shows a graphical representation of the absorption spectrum of compound (8).

[0111] Fig. 9 Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (8), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0112] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (8): C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (8), the fill factor FF is 70.4%, the open-circuit voltage Uoc is 0.72 V, and the short-circuit current Jsc is 11.0 mA / cm². The cell efficiency of such an optoelectronic device, particularly a solar cell, with Compound (8) is 5.58%.

[0113] Fig. 10 shows a graphical representation of the absorption spectrum of compound (10).

[0114] Fig. 11Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (10), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0115] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (10) :C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF:NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (10), the fill factor FF is 67.6%, the open-circuit voltage Uoc is 0.90 V, and the short-circuit current Jsc is 9.6 mA / cm². The cell efficiency of such an optoelectronic device, particularly a solar cell, with Compound (10) is 5.84%.

[0116] Fig. 12shows a graphical representation of the absorption spectrum of compound (14).

[0117] Fig. 13 Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (14), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0118] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (14) :C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF:NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (14), the fill factor FF is 65.0%, the open-circuit voltage Uoc is 0.91 V, and the short-circuit current Jsc is 10.2 mA / cm². The cell efficiency of such an optoelectronic device, in particular a solar cell, with Compound (14) is 6.03%.

[0119] Fig. 14 shows a graphical representation of the absorption spectrum of compound (15).

[0120] Fig. 15Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (15), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0121] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (15) :C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF:NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (15), the fill factor FF is 67.7%, the open-circuit voltage Uoc is 0.95 V, and the short-circuit current Jsc is 9.7 mA / cm². The cell efficiency of such an optoelectronic device, particularly a solar cell, with Compound (15) is 6.24%.

[0122] Fig. 16shows a graphical representation of the absorption spectrum of compound (29).

[0123] Fig. 17 Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (29), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0124] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (29): C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (29), the fill factor FF is 64.0%, the open-circuit voltage Uoc is 0.68 V, and the short-circuit current Jsc is 12.6 mA / cm². The cell efficiency of such an optoelectronic device, in particular a solar cell, with Compound (29) is 5.48%.

[0125] Fig. 18 shows a graphical representation of the absorption spectrum of compound (32).

[0126] Fig. 19Figure 1 shows a graphical representation of the current-voltage curve, the spectral external quantum yield, and the fill factor of a BHJ cell with compound (32), measured on an organic optoelectronic device. In this embodiment, the optoelectronic device is an organic solar cell.

[0127] The current-voltage curve of a BHJ cell with the following structure: ITO / C60 (15 nm) / Compound (32): C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) was determined, where the photoactive layer 4 comprises a bulk heterojunction (BHJ). In the optoelectronic device with Compound (32), the fill factor FF is 69.9%, the open-circuit voltage Uoc is 1.0 V, and the short-circuit current Jsc is 9.4 mA / cm². The cell efficiency of such an optoelectronic device, in particular a solar cell, with Compound (32) is 6.57%.

[0128] The advantageous properties of the compounds according to the invention are also evident in the parameters open-circuit voltage Uoc, short-circuit current Jsc, and fill factor FF, even with identical solar cell structures. The compounds according to the invention exhibit not only improved absorption properties but also suitable charge transport properties. The experimental data for compounds (1), (3), (5), (8), (10), (14), (15), (29), and (32), with their absorption properties and the current-voltage waveforms measured in organic solar cells, demonstrate that these compounds are very well suited for use in organic solar cells and other organic optoelectronic devices.

[0129] Table 1 shows the absorption maxima of compounds (1) to (32) in solution and in film. Table 1 Connection Absorption maximum [nm] in solution Absorption maximum [nm] in the film Melting point [°C] 700 775 378 682 754 718 808 671 738 314 672 741 302 669 735 310 693 743 728 828 677 746 233 678 739 271 730 821 666 614 727 827 308 673 733 290 669 726 315 680 742 234 652 704 307 671 731 352 715 797 306 650 698 277 742 835 651 701 332 711 787 311 650 694 338 670 732 312 648 700 318 651 702 329 652 702 303 724 816 299 660 720 303 659 713 310 670 743 660 707 323 661 717 306 715 815 659 711 297 665 726 316 731 823 349 697 776 334 750 298 738 301 665 729 364 667 731 348 735 832 306 668 742 397 725 821 307 659 707 324 671 744 371 718 808 314 652 704 304 667 738 350 661 314 661 295

[0130] The optical properties were determined experimentally. The absorption maxima Amax were determined in a cuvette containing dichloromethane and from 30 nm thick vacuum vapor deposition layers on quartz glass using a photometer. Surprisingly, it was found that compounds (1) to (32) in the film exhibit particularly broad absorption in the near-infrared range above 650 nm, which is no longer visible to the human eye. Furthermore, it was shown that compounds (1) to (32) possess high thermal stability and can be vaporized in a vacuum without decomposition. The melting temperatures determined by DSC are shown in Table 1.

[0131] Table 2 shows the photovoltaic parameters Voc, Jsc, and FF of the compounds (1) to (32) according to the invention in direct comparison. The cells have the following structure: glass with ITO / C60 (15 nm) / absorber: C60 (30 nm, 3:2, 90°C) / BPAPF (10 nm) / BPAPF: NDP9 (45 nm, 10 wt% NDP9) / NDP9 (1 nm) / Au (50 nm) and were measured under AM1.5 illumination (AM = Air Mass; AM = 1.5; at this spectrum, the global irradiance is < 1000 W / m²; AM = 1.5 is the standard value for measuring solar modules). Table 2 Connection Voc [V] Jsc [mA / cm²< ] FF [%] Eff [%] (1) 0,71 10,2 69,7 5,05 (2) 0,87 9,6 70,3 5,87 (3) 0,69 11,4 73,4 5,77 (5) 0,95 9,4 71,7 6,40 (8) 0,72 11,0 70,4 5,58 (10) 0,90 9,6 67,6 5,84 (13) 0,74 12,0 70,0 6,22 (14) 0,91 10,2 65,0 6,03 (15) 0,95 9,7 67,7 6,24 (29) 0,68 12,6 64,0 5,48 (32) 1,0 9,4 69,9 6,57 (37) 0,70 11,7 67,5 5,53 (38) 0,97 9,6 67,3 6,27 (41) 0,98 8,5 69,3 5,77 (43) 0,72 11,0 62,4 4,94 (45) 0,97 8,8 63,5 5,42 (47) 0,76 10,3 63,8 4,99 (48) 0,76 10,5 69,8 5,57 (49) 0,76 10,3 73,1 5,73 (54) 0,79 11,3 63,6 5,68

[0132] The experimental data of the compounds according to the invention, with the absorption properties of the compounds and the current-voltage profiles measured in organic solar cells, demonstrate that the compounds according to the invention are very well suited for use in organic solar cells and other organic optoelectronic components.

Claims

1. Chemical compound according to general formula I, where X1 and X2 independently of one another are O, S or N-R8, with R8 selected from the group consisting of H, alkyl, aryl, and heteroaryl, R1 is a substituted homocyclic 6-membered ring, where at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR8, with R8 being C1-C4 alkyl, or is a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring, where the heterocyclic 5-membered ring or 6-membered ring has at least one sp2 hybridized N atom with a free electron pair and / or has at least one heteroatom selected from O, S, or N, where in the substituted heterocyclic 5-membered ring or 6-membered ring at least one H atom is substituted by an electron-withdrawing substituent selected from the group consisting of F, Cl, CN, CF3, and COR9, with R9 being C1-C4 alkyl, R2 and R7 independently of one another are selected from the group consisting of H, halogen, CN, alkyl, fluorinated or part-fluorinated alkyl, and unsaturated alkyl, R4 and R5 independently of one another are selected from the group consisting of H, halogen, CN, alkyl, fluorinated or part-fluorinated alkyl, unsaturated alkyl, and alkoxy, and R3 and R6 independently of one another are a substituted or unsubstituted homocyclic 6-membered ring or a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring.

2. Chemical compound according to Claim 1, where X1 and X2 are S or X1 and X2 are O, and / or where at least one H atom in the homocyclic 6-membered ring and / or in the heterocyclic 5-membered ring or 6-membered ring R1 is substituted by F or CF3, preferably by F.

3. Chemical compound according to Claim 1 or 2, where R3 and R4 and / or R5 and R6 in each case together form a heterocyclic 5-membered ring or 6-membered ring having at least one heteroatom selected from O, S or N, preferably O or S, where preferably the heterocyclic 5-membered ring or 6-membered ring is unsubstituted, or form a homocyclic 6-membered ring.

4. Chemical compound according to any of the preceding claims, where R1 is a homocyclic 6-membered ring with the condition that R1 is C6HnF5-n, where n = 0, 1, 2, 3, 4.

5. Chemical compound according to any of the preceding claims, where R1 is selected from the group consisting of: where * denotes the attachment to the compound of the general formula I, where Y independently at each occurrence is selected from the group consisting of Cl, CN, F, and CF3, preferably Y is F, and where H atoms are substituted or unsubstituted.

6. Chemical compound according to any of the preceding claims, where R3 and R6 independently of one another are selected from the group consisting of where * denotes the attachment to the compound of the general formula I, where U is selected from the group consisting of O, S, and NR19, where R19 is selected from the group consisting of H, halogen, alkyl, fluorinated alkyl, part-fluorinated alkyl, alkoxy, alkenyl, aryl, and heteroaryl, preferably U is O or S, and where Z independently of one another is selected from the group consisting of H, halogen, preferably F, CF3, CN, alkyl, fluorinated alkyl, part-fluorinated alkyl, alkenyl, alkoxy, N-alkyl, Nalkyl2, aryl, and heteroaryl, where preferably R3 and R6 are identical.

7. Chemical compound according to any of the preceding claims, where R3 and / or R6 are additionally fused, and / or R1 is a monocyclic 5-membered ring or 6-membered ring.

8. Chemical compound according to any of the preceding claims, where R2 and R7 independently of one another are selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R2 and R7 are H, and / or R4 and R5 independently of one another are selected from the group consisting of H, halogen, CN, and C1-C4 alkyl, preferably R4 and R5 are H.

9. Chemical compound according to any of the preceding claims, where R1 is a heterocyclic 5-membered ring or 6-membered ring having at least one sp2-hybridized N atom with a free electron pair in the ring system, preferably R1 is selected from the group consisting of substituted or unsubstituted imidazole, pyrazole, triazole, tetrazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, oxazole, isoxazole, thiazole, and isothiazole.

10. Chemical compound according to any of the preceding claims, where the compound is selected from the group consisting of:

11. Chemical compound according to any of the preceding claims, where all the H atoms in R1 are substituted by a halogen or CN, preferably all the H atoms are substituted by F.

12. Chemical compound according to any of the preceding claims, where the compound has a molar weight of 300-1500 g / mol.

13. Use of at least one compound according to any of Claims 1 to 12 in an optoelectronic component, preferably an organic optoelectronic component, especially preferably an organic solar cell, an OLED, an OFET, or an organic photodetector.

14. Optoelectronic component having a layer system, where at least one layer of the layer system comprises a compound according to any of Claims 1 to 12, where the optoelectronic component is preferably an organic optoelectronic component, especially preferably an organic solar cell, an OFET, an OLED, or an organic photodetector.

15. Optoelectronic component according to Claim 14, where the optoelectronic component has a layer system with at least one photoactive layer, preferably a light-absorbing photoactive layer, where the at least one photoactive layer comprises the at least one compound according to any of Claims 1 to 12.