Chemical compositions, optoelectronic components comprising at least one chemical composition of this type and the use of at least one chemical composition of this type in optoelectronic components - Patent Application 20070122999

Abstract

The present invention relates to a chemical composition, an optoelectronic component (10) comprising at least one chemical composition of this type, and the use of at least one chemical composition of this type in an optoelectronic component (10).

Description

[Technical Field]

[0001] The present invention relates to compounds, to optoelectronic components comprising at least one compound of this type and to the use of at least one compound of this type in optoelectronic components. [Background technology]

[0002] Organic optoelectronic components have a photoactive layer in which charge carriers, specifically bound electron-hole pairs (excitons), are generated by incident electromagnetic radiation. Through diffusion, the excitons reach an interface where the electrons and holes are separated from each other. Materials that accept electrons are called acceptors, and materials that accept holes are called donors. Organic optoelectronic components can convert electromagnetic radiation into electrical current by utilizing the photoelectric effect. This type of conversion of electromagnetic radiation requires absorbing materials that exhibit good absorption properties.

[0003] Organic optoelectronic components are well known in the prior art. Patent Document 1 discloses a photoactive component, particularly a solar cell, consisting of one or more organic layers of pI, nI, and / or pI diodes stacked on top of each other. Patent Document 2 discloses the structure of an organic solar cell consisting of a pI or nIp diode. A pI solar cell consists of a substrate on which electrodes are arranged, a p-layer, an i-layer, an n-layer, and a counter electrode. In this context, n and p refer to n-type and p-type doping, respectively, which increases the density of free electrons / holes at thermal equilibrium. The term "i-layer" refers to an undoped layer (intrinsic layer) containing an absorbing material or a mixture of two or more absorbing materials. One or more i-layers here may consist of a single material (planar heterojunction) or a mixture of two or more materials (bulk heterojunction). An absorbing material, i.e., an absorber, is understood to mean, in particular, a compound that absorbs light in a specific wavelength range. An absorber layer is therefore understood to mean, in particular, a layer in an optoelectronic component that contains at least one absorbing material.

[0004] From the prior art, a large number of polymeric and non-polymeric absorbing materials for organic photovoltaic devices in the red and near-infrared (NIR) spectral range of 600 nm to 1400 nm are known. In the field of non-polymeric absorbing materials, a group of materials, in particular BODIPY substances, have been found to be suitable for the near-infrared spectral range.

[0005] Non-Patent Document 1 discloses a fluorescent dye-type BODIPY structure in which the meso position is unsubstituted or has a fluorinated alkyl chain.

[0006] Non-Patent Document 2 discloses a BODIPY structure that has a perfluoroalkyl chain at the meso position and can be used as a NIR donor material in organic solar cells.

[0007] Absorbers in the red and near-infrared spectral range known from the prior art have not been satisfactory to date. While known absorbing materials are suitable for the photoactive layer of organic photovoltaic devices, i.e., organic solar cells, there is a need to improve the absorption characteristics of absorbing materials. The efficiency of organic photovoltaic devices depends on factors such as the absorption behavior of the organic material, i.e., the absorbing material, in the photoactive layer. There is a particular need for absorbing materials, particularly donors, with steep absorption edges for use in the NIR subcell of tandem or multijunction solar cells. To avoid parasitic absorption with adjacent subcells, the absorption band of the NIR absorber should preferably not extend too far into the red spectral range. Absorbing materials that combine relatively low parasitic absorption with the red subcell with a relatively steep absorption spectrum are particularly desirable. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] International Publication No. 2004 / 083958A2 Pamphlet [Patent Document 2] International Publication No. 2011 / 161108A1 Brochure [Non-patent literature]

[0009] [Non-Patent Document 1] Umezawa et al. (“Bright,Color-Tunable Fluorescent Dyes in the Visible-Near-Infrared Region”, J.Am.Chem.Soc.,2008,130,5,1550-1551) [Non-patent document 2] Li et al. (“Small Molecule Near-Infrared Boron Dipyrromethene Donors for Organic Tandem Solar Cells”, J.Am.Chem. Soc., 2017, 139, 13636-13639) Summary of the Invention [Problem to be solved by the invention]

[0010] It is therefore an object of the present invention to provide compounds which do not have the listed drawbacks and in particular have a steep absorption edge together with improved absorption properties, optoelectronic components comprising at least one compound of this type and the use of at least one compound of this type in optoelectronic components. [Means for solving the problem]

[0011] This object is achieved by the subject matter of the independent claims. Advantageous configurations will become apparent from the dependent claims.

[0012] For this purpose, in particular compounds of the general formula Ia or Ib [ka] In the compound X1 and X2 are each independently O, S, or NR6, R6 is selected from the group consisting of H, alkyl, alkoxy, amino, aryl, and heteroaryl, R1 is selected from the group consisting of F, fluorinated or partially fluorinated alkyl, and a 5- or 6-membered aromatic heterocyclic ring or a 6-membered aromatic homocyclic ring, R2 and R3 are each independently selected from the group consisting of H, halogen, CN, alkyl, alkoxy, amino, aryl, and heteroaryl, R4 and R5 are each independently selected from the group consisting of halogen, preferably F, and a fluorinated or partially fluorinated alkyl, and Z is, in each occurrence, O, S, CH2, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13 , N.H., N.R. 14 , PR 15 and R is independently selected from the group consisting of 11 , R 12 , R 13 , R 14 and R 15 are each independently selected from the group consisting of halogen, alkyl, alkoxy, amino, aryl, and heteroaryl; n is independently 1 or 2; R and R and / or R and R 10 is achieved by compounds characterized in that, in each case together, they form a heterocyclic five- or six-membered ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, or form a homocyclic six-membered ring, which in each case can be fused to a further ring.

[0013] According to the present invention, the molecular structure of BODIPY compounds is made more rigid by introducing a bridging unit between the BODIPY core and two side units, in particular by a five- or six-membered ring between the BODIPY core and each of the two side units, with the BODIPY core being fused on either side to a side unit, in particular one comprising at least two rings. The resulting rigidification or planarization of the molecular structure of BODIPY compounds results in a steeper absorption edge and a red-shift of the absorption maximum.

[0014] Substitution is understood to mean in particular the replacement of H by a substituent. Substituents are understood to mean in particular all atoms and atomic groups except hydrogen, preferably halogen, alkyl groups (which may be linear or branched), alkenyl groups, alkynyl groups, amino groups, alkoxy groups, thioalkoxy groups, aryl groups or heteroaryl groups. Halogen is understood to mean in particular F, Cl or Br, preferably F.

[0015] Heteroatoms are understood to mean in particular atoms selected from the group consisting of O, S, Se, Si, B, N or P, preferably atoms selected from the group consisting of O, S or N.

[0016] The compounds of the present invention have advantages over the prior art. Advantageously, they can provide improved absorbing materials, especially donors, for optoelectronic components. Advantageously, the compounds have a steep absorption edge above 850 nm, preferably above 870 nm, more preferably above 900 nm, making them particularly suitable for use in subcells of tandem or multi-junction solar cells. The absorption edge of the bridged compounds has a steeper profile, especially compared to the corresponding unbridged compounds. The present invention advantageously provides materials absorbing in the red and near-infrared spectral range that have sharp absorption edges and relatively low parasitic absorption, particularly in subcells of tandem or multijunction cells. Preferably, the absorption of the compounds does not extend into the NIR region. Advantageously, overlap with the absorption region of the red subcell is reduced. Advantageously, the compounds of the present invention have particularly good volatility.

[0017] In the context of the present invention, a bridged compound, in contrast to a non-bridged compound, is understood to mean a BODIPY compound which has a bridge unit between the BODIPY core and each of the two flanking units of the BODIPY core, in particular a BODIPY compound which has a 5- or 6-membered ring between the BODIPY core and each of the two flanking units, the BODIPY core being fused on both sides with flanking units which in particular comprise at least two rings.

[0018] Absorption edge is understood to mean an abrupt transition from weak to strong absorption which occurs in particular at a particular location in the electromagnetic spectrum.

[0019] According to one development of the invention, R1 is selected from the group consisting of F, CF3, C2F5 and a five- or six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring, preferably a five- or six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring in which at least one hydrogen atom is replaced by F, Cl and / or CF3, preferably a six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring in which at least two hydrogen atoms are replaced by F, Cl and / or CF3.

[0020] According to one development of the invention, R7 and R8 and / or R9 and R 10 are, in each case, taken together to form an aromatic homocyclic six-membered ring, preferably wherein at least one hydrogen atom of the homocyclic six-membered ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the homocyclic six-membered ring is not fused to a further ring.

[0021] According to one development of the invention, R7 and R8 and / or R9 and R 10 are, in each occurrence, taken together to form an aromatic five- or six-membered heterocyclic ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, and preferably at least one hydrogen atom of the five- or six-membered heterocyclic ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the five- or six-membered heterocyclic ring is not fused to a further ring.

[0022] In a preferred embodiment of the present invention, R7 and R8 and / or R9 and R 10 in each occurrence, together form a heterocyclic 5- or 6-membered ring containing at least one heteroatom selected from O, S, or N, preferably an unsubstituted heterocyclic 5- or 6-membered ring or an isocyclic 6-membered ring.

[0023] In a preferred embodiment of the present invention, X1 is the same as X2.

[0024] In a preferred embodiment of the invention, R2 and R3 are H or alkyl, preferably H, methyl, ethyl or propyl.

[0025] In a preferred embodiment of the present invention, R4 and R5 are selected from the group consisting of F and CF3, and particularly preferably, R4 and R5 are F.

[0026] According to one development of the invention, R2 is the same as R3, R4 is the same as R5, and / or R7 and R8 are the same as R9 and R 10 is the same as

[0027] In a preferred embodiment of the invention, Z and n are the same in each occurrence.

[0028] In a preferred embodiment of the present invention, R7 is the same as R9 and R8 is R 10 is the same as

[0029] In a preferred embodiment of the present invention, R1 is a heterocyclic 5- or 6-membered ring containing at least one sp2 hybridized nitrogen atom having a free electron pair in the ring system, and 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.

[0030] According to one development of the invention, the compounds have the general formula IIa, IIb, IIc and / or IId: [ka] (wherein U, V, and W in formula IIa and IIb each independently represent CR 16 ,O,S,N,NR 17 and R 16 and R 17 are each independently selected from the group consisting of H, halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; T, U, V, and W in Formulae IIc and IId are each independently selected from the group consisting of CH, CR 18 and N, R 18 is, at each occurrence, independently selected from the group consisting of halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; U, V, and W in Formulae IIa and IIb or T, U, V, and W in Formulae IIc and IId can be fused to a heterocyclic 5- or 6-membered ring or a homocyclic 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, and N; Z is, at each occurrence, O, S, CH, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13 , N.H., N.R. 14 , PR 15 and R is independently selected from the group consisting of 11 , R 12 , R13 , R 14 and R 15 are each independently selected from the group consisting of alkyl, alkoxy, amino, aryl, and heteroaryl, and n, in each occurrence, is independently 1 or 2. It has.

[0031] In a preferred embodiment of the invention, X1 and X2 are O or S, R2 and R3 are H, and R4 and R5 are F.

[0032] According to one development of the invention, at least one of U, V and W in formulae IIa and IIb is O or S, preferably U or W, and T, U, V and W in formulae IIc and IId are each independently CH and CR 18 and R 18 is, at each occurrence, independently selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl, and / or at least U or V in formulas IIc and IId is selected from the group consisting of CR 18 and R 18 is selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl; or T, U, V, and W in Formulas IIc and IId are each independently CH or CR 18 and R 18 is alkyl, and preferably T, U, V and W in formulae IIc and IId are H.

[0033] In a preferred embodiment of the present invention, U, V, W in formula IIa or IIb or T, U, V, W in formula IIc or IId are fused with at least one other homocyclic or heterocyclic 5- or 6-membered ring, preferably a heteroaromatic 5- or 6-membered ring or a homoaromatic 6-membered ring.

[0034] In a preferred embodiment of the present invention, X1 and / or X2 are each independently selected from the group consisting of R 11 , R 12 , R 13 , R 14 or R 15together with the aryloxy group to form a heterocyclic 5- or 6-membered ring or a homocyclic 6-membered ring containing at least one heteroatom selected from the group consisting of O, S and N, preferably a heterocyclic 5-membered ring.

[0035] According to one development of the invention, Z is in each case O, S, CH2, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13 , N.H., N.R. 14 , PR 15 and R is independently selected from the group consisting of 11 , R 12 , R 13 , R 14 and R 15 are each independently selected from the group consisting of alkyl, alkoxy, preferably alkyl, or Z, at each occurrence, is O, S, CH, CHR 11 and CR 12 R 13 and R is independently selected from the group consisting of 11 , R 12 and R 13 are each independently selected from the group consisting of alkyl, aryl, and heteroaryl, and / or n is 1.

[0036] In a particularly preferred embodiment of the present invention, Z is CH, CHR 11 , C.R. 12 R 13 and R 11 , R 12 and R 13 are each independently alkyl, preferably methyl, ethyl, propyl or isopropyl.

[0037] According to one development of the invention, R4 and R5 are F and / or X1 and X2 are O or S, respectively.

[0038] According to one development of the invention, R2 and R3 are each independently selected from the group consisting of H, alkyl, alkoxy, aryl and heteroaryl, and R2 and R3 are preferably H or alkyl, particularly preferably H, methyl, ethyl or propyl.

[0039] According to one development of the invention, Z is CH2, CHR 11 and CR 12 R 13 Selected from R 11 , R 12 and R 13 are each independently selected from the group consisting of alkyl, alkoxy, aryl and heteroaryl, preferably H or alkyl, and / or n is 1.

[0040] In an alternative preferred embodiment of the invention, the ring in formulae IIa, IIb, IIc and IId is not fused to an additional ring.

[0041] In a preferred embodiment of the invention, the compound has mirror symmetry about the axis passing through R1 and B.

[0042] According to one development of the invention, the compound is: [ka] [ka] [ka] is selected from the group consisting of:

[0043] The compounds of the present invention particularly relate to "small molecules". Small molecules are understood to mean, in particular, non-polymeric organic molecules with a monodisperse molar mass of 100 to 2000 g / mol that are in the solid phase at standard pressure (atmospheric pressure) and room temperature. In particular, small molecules are photoactive. Photoactivity is understood to mean that the molecule undergoes a change in charge and / or polarization state when exposed to light. Photoactive molecules exhibit, in particular, absorption of electromagnetic radiation within a defined wavelength range, and the absorbed electromagnetic radiation, i.e., photons, are converted into excitons. In a preferred embodiment of the present invention, the compounds have a molecular weight of 300 to 1500 g / mol.

[0044] The object of the present invention is also achieved by providing an optoelectronic component, in particular an optoelectronic component according to any of the exemplary embodiments described above, comprising a first electrode, a second electrode, and a layer system arranged between the first and second electrodes. In the optoelectronic component, at least one layer of the layer system comprises at least one compound of the present invention. For optoelectronic components comprising at least one compound, this has the advantages already described, in particular in relation to the compounds of the present invention.

[0045] According to one development of the invention, the optoelectronic component comprises a layer system with at least one photoactive layer, preferably a light-absorbing photoactive layer, wherein the at least one photoactive layer comprises at least one compound.

[0046] In a preferred embodiment of the present invention, at least one photoactive layer is an absorbing layer, and preferably at least one compound is an absorbing material, particularly preferably a donor.

[0047] In a preferred embodiment of the present invention, the layer system comprises at least two photoactive layers, preferably at least three photoactive layers or preferably at least four photoactive layers.

[0048] According to one development of the invention, the optoelectronic component is an organic photovoltaic element, an OFET (organic field-effect transistor), an OLED (organic light-emitting diode) or an organic photodetector. Organic photovoltaic elements make it possible to convert electromagnetic radiation, in particular in the visible light wavelength range, into electrical current by utilizing the photoelectric effect. In this context, the term "photoactive" is understood to mean the conversion of light energy into electrical energy.

[0049] The object of the present invention is also achieved by providing the use of the compounds of the present invention in optoelectronic components, in particular according to one of the above-mentioned exemplary embodiments, which use of the compounds in optoelectronic components has in particular the advantages already explained in relation to the compounds of the present invention and optoelectronic components comprising at least one compound.

[0050] According to a further development of the invention, the compounds according to the invention are used in organic photovoltaics, OFETs (organic field effect transistors), OLEDs (organic light emitting diodes) or organic photodetectors.

[0051] In a preferred embodiment of the present invention, at least one compound of the present invention is used as an absorbing material in a photoactive layer of an optoelectronic component. In a preferred embodiment of the present invention, a compound of the present invention is used as a donor in a donor-acceptor heterojunction.

[0052] In a preferred embodiment of the present invention, the layer system of the optoelectronic component comprises at least one transport layer, which is doped, partially doped or undoped. Preferably, the layer system comprises at least one electron transport layer (ETL) and at least one hole transport layer (HTL).

[0053] In a preferred embodiment of the present invention, the compounds and / or layers comprising at least one compound are deposited by vacuum processing, vapor deposition or solvent processing, particularly preferably by vacuum processing.

[0054] The invention will be explained in more detail below with reference to the drawings. [Brief explanation of the drawings]

[0055] [Figure 1] 1 shows a schematic cross-sectional view of an exemplary embodiment of an optoelectronic component; [Figure 2] 1 shows a graphical representation of the absorption spectra of inventive and non-inventive compounds. [Figure 3] 1 shows a graphical representation of the current-voltage curve, spectral external quantum yield and fill factor of a BHJ cell containing compound (02) measured on an organic optoelectronic device. [Figure 4] 1 shows a graphical representation of the current-voltage curve, spectral external quantum yield and fill factor of a BHJ cell containing compound (03) measured on an organic optoelectronic device. [Figure 5] 1 shows a graphical representation of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound (12) measured on an organic optoelectronic device. [Figure 6] 1 shows a graphical representation of the current-voltage curve, spectral external quantum yield, and fill factor of a PHJ cell containing compound (12) measured on an organic optoelectronic device. DETAILED DESCRIPTION OF THE INVENTION

[0056] 1 shows a schematic diagram of an exemplary embodiment of an optoelectronic component in cross section. The optoelectronic component 10 here comprises at least one compound of general formula Ia or Ib.

[0057] The optoelectronic component 10 comprises a first electrode 2, a second electrode 6 and a layer system 7, which is arranged between the first electrode 2 and the second electrode 6. At least one layer of the layer system 7 here comprises at least one compound according to the invention.

[0058] In one configuration of the present invention, the optoelectronic component 10 comprises a layer system 7 having at least one photoactive layer 4, preferably a light-absorbing photoactive layer 4, wherein the at least one photoactive layer 4 comprises at least one compound. The optoelectronic component 10 can be an organic photovoltaic device, an OFET (organic field-effect transistor), an OLED (organic light-emitting diode), or an organic photodetector. In this exemplary embodiment, the optoelectronic component 10 is an organic photovoltaic device.

[0059] In this exemplary embodiment, the organic photovoltaic device comprises a layer system 7 having at least one photoactive layer 4, preferably a light-absorbing photoactive layer 4, wherein the at least one photoactive layer 4 comprises at least one compound of the present invention.

[0060] In one exemplary embodiment, an organic photovoltaic device comprises a substrate 1, e.g., made of glass, on which an electrode 2, e.g., made of ITO, is disposed. A layer system 7 is disposed thereon, comprising an electron transport layer 3 (ETL) and a photoactive layer 4, which comprises at least one compound of the present invention as a p-type conductive donor material and an n-type conductive acceptor material, e.g., C60 fullerene. The active layer 4 can be formed as either a planar heterojunction (PHJ) or a bulk heterojunction (BHJ). A p-type doped hole transport layer 5 (HTL) and an electrode 6, e.g., made of gold or aluminum, are disposed thereon.

[0061] In a further configuration of the invention, the photoactive layer 4 is formed as a mixed layer of at least one compound of the invention and at least one additional compound or at least one compound of the invention and at least two additional compounds, which compounds are absorbing materials.

[0062] In a further configuration of the invention, the layer system 7 comprises at least two photoactive layers 4 , preferably at least three photoactive layers 4 or preferably at least four photoactive layers 4 .

[0063] In a further configuration of the invention, the optoelectronic component 10 is formed as a tandem cell, triple cell or multi-cell, in which two or more photoactive layers 4 are stacked on top of each other and are made of the same or different materials or material mixtures.

[0064] The individual layers of the optoelectronic component 10 of the present invention can be produced by evaporation under reduced pressure with or without a carrier gas or by processing a solution or suspension, for example during coating or printing. The individual layers can also be applied by sputtering. This is particularly possible for the base contact. It is advantageous to produce the layers by evaporation under reduced pressure, for which the supporting substrate can be heated.

[0065] The general methods for preparing the compounds of the invention are known to those skilled in the art from the prior art, in this regard reference is made in particular to the international application WO 2007 / 126052 A1.

[0066] Compounds of general formula Ia or Ib have the following structure: [ka] wherein X1 and X2 are each independently O, S, or NR6; R6 is selected from the group consisting of H, alkyl, alkoxy, amino, aryl, and heteroaryl; R1 is selected from the group consisting of F, fluorinated or partially fluorinated alkyl, and a 5- or 6-membered aromatic heterocyclic ring or a 6-membered aromatic homocyclic ring; R2 and R3 are each independently selected from the group consisting of H, halogen, CN, alkyl, alkoxy, amino, aryl, and heteroaryl; R4 and R5 are each independently selected from the group consisting of halogen, preferably F, and a fluorinated or partially fluorinated alkyl; and Z, in each occurrence, is O, S, CH2, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13 , N.H., N.R. 14, PR 15 and R is independently selected from the group consisting of 11 , R 12 , R 13 , R 14 and R 15 are each independently selected from the group consisting of halogen, alkyl, alkoxy, amino, aryl, and heteroaryl; n, in each occurrence, is independently 1 or 2; R and R and / or R and R 10 in each case together form a heterocyclic 5- or 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, or form a homocyclic 6-membered ring, which heterocyclic 5- or 6-membered ring or homocyclic 6-membered ring can in each case be fused to a further ring It has.

[0067] In one aspect of the invention, R1 is selected from the group consisting of F, CF3, C2F5 and a five- or six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring, preferably a five- or six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring in which at least one hydrogen atom is replaced by F, Cl and / or CF3, preferably a six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring in which at least two hydrogen atoms are replaced by F, Cl and / or CF3.

[0068] In a further configuration of the invention, R7 and R8 and / or R9 and R 10 are, in each case, taken together to form an aromatic homocyclic six-membered ring, preferably wherein at least one hydrogen atom of the homocyclic six-membered ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the homocyclic six-membered ring is not fused to a further ring.

[0069] In a further configuration of the invention, R7 and R8 and / or R9 and R 10are, in each occurrence, taken together to form an aromatic five- or six-membered heterocyclic ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, and preferably at least one hydrogen atom of the five- or six-membered heterocyclic ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the five- or six-membered heterocyclic ring is not fused to a further ring.

[0070] In a further configuration of the invention, R2 is the same as R3, R4 is the same as R5, and / or R7 and R8 are the same as R9 and R 10 is the same as

[0071] In a further aspect of the invention, the compounds have the general formula IIa, IIb, IIc and / or IId: [ka] (wherein U, V, and W in formula IIa and IIb each independently represent CR 16 ,O,S,N,NR 17 and R 16 and R 17 are each independently selected from the group consisting of H, halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; T, U, V, and W in Formulae IIc and IId are each independently selected from the group consisting of CH, CR 18 and N, R 18 is, at each occurrence, independently selected from the group consisting of halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; U, V, and W in Formulae IIa and IIb or T, U, V, and W in Formulae IIc and IId can be fused to a heterocyclic 5- or 6-membered ring or a homocyclic 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, and N; Z is, at each occurrence, O, S, CH, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13, N.H., N.R. 14 , PR 15 and R is independently selected from the group consisting of 11 , R 12 , R 13 , R 14 and R 15 are each independently selected from the group consisting of alkyl, alkoxy, amino, aryl, and heteroaryl, and n, in each occurrence, is independently 1 or 2. It has.

[0072] In a further aspect of the invention, at least one of U, V and W in formulae IIa and IIb is O or S, preferably U or W, and T, U, V and W in formulae IIc and IId are each independently CH and CR 18 and R 18 is, at each occurrence, independently selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl; and / or At least U or V in formula IIc and IId is CR 18 and R 18 is selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl; or T, U, V, and W in Formulas IIc and IId are each independently CH or CR 18 and R 18 is alkyl, and preferably T, U, V and W in formulae IIc and IId are H.

[0073] In a further embodiment of the invention, Z is in each case O, S, CH, CHR 11 , C.R. 12 R 13 , SiHR 11 , SiR 12 R 13 , N.H., N.R. 14 , PR 15 and R is independently selected from the group consisting of 11 , R 12 , R 13 , R 14 and R 15are each independently selected from the group consisting of alkyl, alkoxy, preferably alkyl, or Z, in each occurrence, is O, S, CH, CHR 11 and CR 12 R 13 and R is independently selected from the group consisting of 11 , R 12 and R 13 are each independently selected from the group consisting of alkyl, aryl, and heteroaryl, and / or n is 1.

[0074] In a further configuration of the invention, R4 and R5 are F and / or X1 and X2 are O or S, respectively.

[0075] In a further aspect of the invention, R2 and R3 are each independently selected from the group consisting of H, alkyl, alkoxy, aryl and heteroaryl, and R2 and R3 are preferably H or alkyl, more preferably H, methyl, ethyl or propyl.

[0076] In a further aspect of the invention, Z is CH2, CHR 11 and CR 12 R 13 Selected from R 11 , R 12 and R 13 are each independently selected from the group consisting of alkyl, alkoxy, aryl and heteroaryl, preferably H or alkyl, and / or n is 1.

[0077] FIG. 2 shows a graph depicting the absorption spectra of a compound of the present invention and a compound that is not a compound of the present invention.

[0078] The absorption spectra of compounds (2), (3), and (12) of the present invention are compared with those of compounds C02 and C14, which are not compounds of the present invention. The absorption spectra (optical density (nm) vs. wavelength) of the compounds were measured in each case on quartz glass and on 30 nm thick vacuum-deposited layers in dichloromethane solution.

[0079] Crosslinked compounds (2), (3) and (12) show an absorption region that is shifted to the red spectral range of visible light compared to uncrosslinked compounds C02 and C14.

[0080] 3-6 that follow show certain exemplary embodiments of organic photovoltaic devices comprising the inventive compounds of general formula I.

[0081] 3 shows a graph depicting the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell including compound (02) measured on an organic optoelectronic component 10. In this exemplary embodiment, the optoelectronic component 10 is an organic photovoltaic device.

[0082] The current-voltage curve contains the indices that characterize an organic photovoltaic device, the most important of which are the fill factor FF, the open circuit voltage Uoc, and the short circuit current Jsc.

[0083] To investigate the compound's use as an absorber in organic photovoltaic devices, the current-voltage curve of a BHJ cell was measured. In this exemplary embodiment, a BHJ cell on an ITO layer had a 15 nm thick C60 layer 3. A 30 nm thick layer of compound (02) was coated on top of this layer with C60 at a molar ratio of 2:3 at 90 °C as the photoactive layer 4. This layer was followed by a 10 nm thick BF-DBP layer, which was then followed by a 45 nm thick layer of BF-DBP with 4.1 wt% NDP9 as the hole transport layer 5. This layer was adjacent to another 1 nm thick layer containing NDP9, which was then followed by a 50 nm thick gold layer. Here, ITO served as the electrode 2, and the adjacent fullerene C60 served as the electron transport layer (ETL) 3. This layer is adjacent to the photoactive layer 4, which contains C60 as the electron acceptor material and the respective absorber, followed by BF-DBP as the hole transport layer (HTL) 5 and BF-DBP doped with NDP9 (Novaled AG), which is then followed by a gold electrode 6.

[0084] The current-voltage curve of a BHJ cell with the following structure was determined: ITO / C60 (15 nm) / Compound (02):C60 (30 nm, 3:2, 90 °C) / BF-DBP (10 nm) / BF-DBP:NDP9 (45 nm, 4.1 wt% NDP9) / NDP9 (1 nm) / Au (50 nm). The cell parameters were measured under AM 1.5 illumination (AM = air mass, AM = 1.5; in this spectrum, the total radiant power is 1000 W / m). 2 (where AM=1.5 is the default value for measuring solar cell modules.) The photoactive layer 4 here comprises a bulk heterojunction (BHJ).

[0085] In the organic photovoltaic device containing compound (02), the fill factor FF was 55.6%, the open circuit voltage Uoc was 0.58 V, and the short circuit current Jsc was 10.8 mA / cm 2 The cell efficiency of this type of optoelectronic component 10, particularly a photovoltaic device, containing compound (02) is 3.48%. Compound (02) exhibits excellent volatility under reduced pressure.

[0086] 4 shows graphs depicting the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound (03) measured on an organic optoelectronic component 10. In this exemplary embodiment, the optoelectronic component 10 is an organic photovoltaic device. The structure of the BHJ cell corresponds to that of the cell of FIG. 3 in which compound (03) was used as the donor in the photoactive layer 4.

[0087] In the organic photovoltaic device containing compound (03), the fill factor FF was 61.5%, the open circuit voltage Uoc was 0.69 V, and the short circuit current Jsc was 9.9 mA / cm 2 The cell efficiency of this type of optoelectronic component 10, particularly a photovoltaic device, containing compound (03) is 4.20%. Compound (03) exhibits excellent volatility under reduced pressure.

[0088] FIG. 5 shows graphs depicting the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound (12) measured on an organic optoelectronic component 10. In this exemplary embodiment, optoelectronic component 10 is an organic photovoltaic device. The structure of the BHJ cell corresponds to that of the cell in FIG. 3 in which compound (12) was used as the donor in photoactive layer 4.

[0089] In the organic photovoltaic device containing compound (12), the fill factor FF was 53.7%, the open circuit voltage Uoc was 0.74 V, and the short circuit current Jsc was 9.7 mA / cm 2 The cell efficiency of this type of optoelectronic component 10, particularly a photovoltaic device, containing compound (12) is 3.85%. Compound (12) exhibits excellent volatility under reduced pressure.

[0090] 6 shows graphs depicting the current-voltage curve, spectral external quantum yield, and fill factor of a PHJ cell including compound (12) measured on an organic optoelectronic component 10. In this exemplary embodiment, the optoelectronic component 10 is an organic photovoltaic device.

[0091] The current-voltage curve of a PHJ cell was determined, which had the following structure: ITO / C60 (15 nm) / Compound (12) (6 nm, 20 °C) / BF-DBP (10 nm) / BF-DBP:NDP9 (45 nm, 4 wt% NDP9) / NDP9 (1 nm) / Au (50 nm). The photoactive layer 4 here comprises a planar heterojunction (PHJ).

[0092] In the organic photovoltaic device containing compound (12), the fill factor FF was 70.0%, the open circuit voltage Uoc was 0.67 V, and the short circuit current Jsc was 7.2 mA / cm 2 The cell efficiency of this type of optoelectronic component 10, in particular a photovoltaic device, containing compound (12) is 3.38%.

[0093] The advantageous properties of the compounds of the present invention are specifically demonstrated by their absorption properties, especially compared to non-crosslinked compounds that are not compounds of the present invention. Table 1 summarizes the absorption maxima and slopes of compounds (01)-(15) in solution and in films, compared to compounds C02, C03, C05, and C14, which are not compounds of the present invention. [ka]

[0094] [Table 1]

[0095] [Table 2]

[0096] [Table 3]

[0097] [Table 4]

[0098] The tangent to the inflection point of the long-wave absorption edge is determined to determine the slope, which is the reciprocal of the difference between the abscissa (eV) of the inflection point and the zero point (eV) of the tangent.

[0099] The optical properties were determined experimentally. The absorption maximum λmax was determined using a photometer in a cuvette containing dichloromethane on a 30 nm thick vacuum-deposited layer on quartz glass. Surprisingly, in films, compounds (01) to (15) were found to have absorption maxima shifted in particular to the near-infrared spectral range, in particular above 750 nm, preferably above 780 nm, and more preferably above 800 nm. In addition, the crosslinked compounds (01) to (15) have particularly steep absorption edges compared to the corresponding uncrosslinked compounds in each case.

[0100] For example, the absorption edge of cyclopentadiene-bridged compound (02) is 11.58 e / V, which is steeper than the absorption edge of compound C02 (6.96 e / V). The absorption edge of cyclopentadiene-bridged compound (03) is 10.05 e / V, which is steeper than the absorption edge of compound C03 (5.11 e / V). Pyridine-bridged compounds (08), (11), and (12), pyran-bridged compounds (05) and (06), and cyclopentadiene-bridged compound (10) also show steeper absorption edges than compound C05.

[0101] Table 2 shows the photovoltaic parameters Voc, Jsc and FF of the compounds (01) to (15) of the present invention. The cells have the following structure: BHJ cell: ITO / glass with C60 (15 nm) / absorber: C60 (30 nm, 3:2, 90 °C) / BF-DBP (10 nm) / BF-DBP:NDP9 (45 nm, 4 wt% NDP9) / NDP9 (1 nm) / Au (50 nm); PHJ cell: ITO / C60 with glass (15 nm) / absorber (6 nm, 20 °C) / BF-DBP (10 nm) / BF-DBP:NDP9 (45 nm, 4 wt% NDP9) / NDP9 (1 nm) / Au (50 nm); measured under AM 1.5 illumination (AM = air mass, AM = 1.5; for this spectrum, the total radiant power is 1000 W / m 2 and AM=1.5 is the default value for measuring solar modules).

[0102] BF-DBP: Hole transport material [ka]

[0103] [Table 5]

[0104] *In cells containing compounds (01) and (014), the hole transport material BF-DBP was replaced by the hole transport material HTM081 from Merck AG.

[0105] It was also found that compounds (01) to (15) have high thermal stability and can be evaporated under reduced pressure without decomposition.

[0106] Experimental data for the compounds of the present invention, including the absorption properties of the compounds and current-voltage curves measured in organic photovoltaic devices, indicate that the compounds of the present invention are highly suitable for use in organic photovoltaic devices and other organic optoelectronic components.

[0107] synthesis The basic synthetic methods for preparing compounds of general formula Ia or Ib are known from WO 2007126052 A1, Bartellmess et al. ("meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties", New Journal of Chemistry, 37(9), 2663-2668; 2013) and Li et al. ("Small Molecule Near-Infrared Boron Dipyrromethene Donors for Organic Tandem Solar Cells", J. Am. Chem. Soc., 2017, 139, 13636-13639). [Example]

[0108] The following is an exemplary embodiment of the synthesis of the compounds of the present invention, in which the aldehyde shown here is used to prepare the corresponding BODIPY according to Umezawa et al. (J. Am. Chem. Soc., 2008, 130, 5, 1550-1551) or Yang et al. (Chem. Commun., 2013, 49, 3940-3942).

[0109] [ka]

[0110] General procedure for A2: Compound A1 (1 equivalent) was dissolved in 50 volumes of anhydrous THF (tetrahydrofuran) at -30°C and treated dropwise with n-BuLi (2.5 mol / L, 1.40 equivalents). The mixture was stirred at -30°C for 30 minutes, treated with methyl iodide (1.60 equivalents), and then warmed to 20°C overnight. The mixture was added to semi-concentrated ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and saturated NaCl solution. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: DCM / PE 20:80) afforded compound A2 as a colorless solid (97%).

[0111] General procedure for A3: A solution of dimethylformamide (1.30 equiv.) in 2 volumes of anhydrous DCM was treated with phosphorus oxychloride (1.20 equiv.) at 0°C and stirred at 0°C for 30 minutes. This solution was then added dropwise to a solution of compound A2 (1 equiv.) in 8 volumes of anhydrous DCM at 0°C. The mixture was stirred at 20°C for 2 hours. The mixture was then treated with 25 volumes of NaOH solution (1 M) and stirred for 40 minutes. The organic phase was separated, and the aqueous phase was extracted with DCM. The organic phase was washed with water and saturated NaCl solution. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: DCM / EtOAc / PE 55:5:40) afforded compound A3 as a yellow solid (86%).

[0112] [ka]

[0113] General procedure for A5: A solution of methyl 2-bromo-5-methoxybenzoate A4 (1 equivalent) and 2-thiopheneboronic acid (1.10 equivalents) in 10 volumes of isopropanol was treated with a solution of potassium phosphate (1.20 equivalents) in 2.5 volumes of water and degassed for 20 minutes. Bis(tri-tert-butylphosphine)palladium(0) (0.005 equivalents) was then added, and the mixture was stirred at 20 °C for 2 hours. The mixture was added to water and extracted three times with DCM. The organic phase was washed with water and saturated NaCl solution. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: EtOAc) afforded compound A5 as a reddish oil (97%).

[0114] General procedure for A6: A solution of compound A5 (1 equiv.) in 8 volumes of anhydrous THF was treated at -10 °C with a solution of methylmagnesium bromide (3.4 mol / L in THF) (3 equiv.) dropwise under stirring. The mixture was stirred at 40 °C for 3 h, cooled to -10 °C, and treated with the slow addition of HCl solution (1 M, 2 equiv.). Saturated ammonium chloride solution was then added until a pH of 7-8 was reached. The mixture was extracted three times with DCM. The organic phase was dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / EtOAc 83:17) afforded compound A6 as a yellow oil (87%).

[0115] General procedure for A7: A solution of compound A6 (1 equivalent) in 30 volumes of anhydrous DCM was treated with dropwise addition of methanesulfonic acid (2 equivalents) at -78°C. The mixture was stirred at -78°C for 30 minutes, then warmed to 0°C and treated with saturated sodium bicarbonate solution. The mixture was then extracted three times with DCM. The organic phase was washed with water, dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 67:33) afforded compound A7 as a colorless oil (65%).

[0116] General procedure for A8: A solution of dimethylformamide (1.50 equiv.) in 5 volumes of anhydrous DCM was treated with phosphorus oxychloride (1.50 equiv.) at 0° C. and stirred at 0° C. for 30 minutes. This solution was then added dropwise to a solution of compound A7 (1 equiv.) in 3 volumes of anhydrous DCM at 0° C. The mixture was stirred at 20° C. for 1.5 hours. The mixture was then treated with 25 volumes of NaOH solution (1 M) and stirred for 2 hours. The organic phase was separated and washed with water. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: DCM) afforded compound A8 as a yellow solid (96%).

[0117] [ka]

[0118] General procedure for A10: A solution of 4-bromo-3-nitrotoluene A9 (1 equivalent) and 2-thiopheneboronic acid (1.10 equivalents) in 18 volumes of isopropanol was treated with a solution of potassium phosphate (1.20 equivalents) in 4.5 volumes of water, and the mixture was degassed for 20 minutes. Bis(tri-tert-butylphosphine)palladium(0) (0.01 equivalents) was then added, and the mixture was stirred at 20 °C for 2 hours. The mixture was added to water and extracted three times with DCM. The organic phase was washed with water and saturated NaCl solution. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 67:33) afforded compound A10 as a colorless oil (99%).

[0119] General procedure for A11: A solution of compound 10 (1 equivalent) in triethyl phosphite (5 equivalents) was stirred under reflux for 16 hours. The mixture was then cooled to 20°C, and the solvent was removed by distillation under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 75:25) afforded compound A11 as a colorless oil (52%).

[0120] General procedure for A12: A solution of compound A11 (1 equivalent) and potassium hydroxide (2.10 equivalents) in 12 volumes of anhydrous DMSO was treated with isopropyl iodide (2 equivalents) and stirred at 20 °C for 2 days. The mixture was then added to water and extracted three times with EtOAc. The organic phase was dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 67:33) afforded compound A12 as a colorless solid (92%).

[0121] General procedure for A13: A solution of dimethylformamide (1.50 equiv.) in 4 volumes of anhydrous DCM was treated with phosphorus oxychloride (1.60 equiv.) at 0° C. and stirred at 0° C. for 40 minutes. This solution was then added dropwise to a solution of compound A12 (1 equiv.) in 4 volumes of anhydrous DCM at 0° C. The mixture was stirred at 20° C. for 2.5 hours. The mixture was then treated with 25 volumes of NaOH solution (1 M) and stirred for 2 hours. The organic phase was separated and washed with water. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: EtOAc) afforded compound A13 as a yellow solid (96%).

[0122] [ka]

[0123] A14 Basic Procedure: International Publication No. 2022126179A1 Brochure

[0124] General procedure for A15: A solution of compound A14 (1 equivalent) and potassium hydroxide (2.60 equivalents) in 12 volumes of anhydrous DMSO was treated with isopropyl iodide (2.50 equivalents) and stirred at 20 °C for 3 hours. The mixture was then added to water and extracted three times with EtOAc. The organic phase was dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 67:33) afforded compound A15 as a colorless solid (86%).

[0125] General procedure for A16: A solution of dimethylformamide (1.60 equiv.) in 4 volumes of anhydrous DCM was treated with phosphorus oxychloride (1.50 equiv.) at 0° C. and stirred at 0° C. for 40 minutes. This solution was then added dropwise to a solution of compound A15 (1 equiv.) in 4 volumes of anhydrous DCM at 0° C. The mixture was stirred at 20° C. for 1.5 hours. The mixture was then treated with 30 volumes of NaOH solution (1 M) and stirred for 2 hours. The organic phase was separated and washed with water. It was then dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel column chromatography (eluent: PE / DCM 50:50) afforded compound A16 as an orange solid (90%).

[0126] [ka]

[0127] Basic procedure for A17: Yan et al. (J. Org. Chem., 2008, 73, 17, 6587-6594)

[0128] [ka]

[0129] Basic procedure for A18: Svoboda et al. (Collect. Czech. Chem. Commun., 1996, 61, 888-900)

Claims

1. General Formula Ia or Ib 【Chemistry 1】 In the compound X １ and X ２ are each independently O, S or NR ６ and R ６ is selected from the group consisting of H, alkyl, alkoxy, amino, aryl, and heteroaryl; R １ is selected from the group consisting of F, fluorinated or partially fluorinated alkyl and a 5- or 6-membered aromatic heterocyclic ring or a 6-membered aromatic homocyclic ring; R ２ and R ３ are each independently selected from the group consisting of H, halogen, CN, alkyl, alkoxy, amino, aryl, and heteroaryl; R ４ and R ５ are each independently selected from the group consisting of halogen, preferably F, and fluorinated or partially fluorinated alkyl; Z, in each occurrence, is O, S, CH ２ , CHR １１ , C.R. １２ R １３ , SiHR １１ , SiR １２ R １３ , N.H., N.R. １４ , P.R. １５ and R １１ , R １２ , R １３ , R １４ and R １５ are each independently selected from the group consisting of halogen, alkyl, alkoxy, amino, aryl, and heteroaryl; and n, in each occurrence, is independently 1 or 2; R ７ and R ８ and / or R ９ and R １０ in each case together form a heterocyclic 5- or 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, or form a homocyclic 6-membered ring, which in each case can be fused to a further ring.

2. R １ , F, CF ３ , C ２ F ５ and aromatic heterocyclic 5- or 6-membered rings or aromatic homocyclic 6-membered rings, preferably in which at least one hydrogen atom is F, Cl and / or CF ３ an aromatic heterocyclic 5- or 6-membered ring or an aromatic homocyclic 6-membered ring, preferably substituted with at least two hydrogen atoms by F, Cl and / or CF ３ 2. The compound of claim 1, wherein the ring is selected from the group consisting of a six-membered aromatic heterocyclic ring or a six-membered aromatic homocyclic ring substituted by:

3. R ７ and R ８ and / or R ９ and R １０ are, in each case, taken together to form an aromatic homocyclic six-membered ring, preferably wherein at least one hydrogen atom of the homocyclic six-membered ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the homocyclic six-membered ring is not fused to a further ring.

4. R ７ and R ８ and / or R ９ and R １０ and in each case together form an aromatic heterocyclic 5- or 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, N, Si or P, and preferably at least one hydrogen atom of the heterocyclic 5- or 6-membered ring is replaced by halogen, alkyl, alkoxy, aryl or heteroaryl, and / or the heterocyclic 5- or 6-membered ring is not fused to a further ring.

5. R ２ is R ３ is the same as R ４ is R ５ and / or R ７ and R ８ is R ９ and R １０ The compound of claim 1, wherein

6. General formula IIa, IIb, IIc and / or IId: 【Chemistry 2】 wherein U, V, and W in Formula IIa and IIb are each independently CR １６ ,O,S,N,NR １７ and R １６ and R １７ are each independently selected from the group consisting of H, halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; T, U, V, and W in formula IIc and IId are each independently CH, CR １８ and N, R １８ is, at each occurrence, independently selected from the group consisting of halogen, alkyl, alkoxy, alkylthiooxy, amino, aryl, and heteroaryl; and U, V, and W in Formulae IIa and IIb or T, U, V, and W in Formulae IIc and IId can be fused to a heterocyclic 5- or 6-membered ring or a homocyclic 6-membered ring containing at least one heteroatom selected from the group consisting of O, S, and N; Z, in each occurrence, is O, S, CH ２ , CHR １１ , C.R. １２ R １３ , SiHR １１ , SiR １２ R １３ , N.H., N.R. １４ , P.R. １５ and R １１ , R １２ , R １３ , R １４ and R １５ are each independently selected from the group consisting of alkyl, alkoxy, amino, aryl, and heteroaryl, and n, in each occurrence, is independently 1 or 2.

2. The compound of claim 1 having the formula:

7. at least one of U, V and W in formulae IIa and IIb is O or S, preferably U or W; T, U, V, and W in formula IIc and IId are each independently CH and CR １８ and R １８ is, at each occurrence, independently selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl; and / or At least U or V in formula IIc and IId is CR １８ and R １８ is selected from the group consisting of alkyl, alkoxy, aryl, and heteroaryl; or T, U, V, and W in Formulas IIc and IId are each independently CH or CR １８ and R １８ is alkyl, and preferably T, U, V and W in formulae IIc and IId are H.

8. Z, in each occurrence, is O, S, CH ２ , CHR １１ , C.R. １２ R １３ , SiHR １１ , SiR １２ R １３ , N.R. １４ , P.R. １５ and R １１ , R １２ , R １３ , R １４ and R １５ are each independently selected from the group consisting of alkyl, alkoxy, preferably alkyl, or Z is each occurrence O, S, CH ２ , CHR １１ and CR １２ R １３ and R １１ , R １２ and R １３ are each independently selected from the group consisting of alkyl, aryl, and heteroaryl, and / or n is 1.

9. R ４ and R ５ is F and / or X １ and X ２ The compound of claim 1 , wherein each of is O or S.

10. R ２ and R ３ are each independently selected from the group consisting of H, alkyl, alkoxy, aryl, and heteroaryl; R ２ and R ３ is preferably H or alkyl, particularly preferably H, methyl, ethyl or propyl.

11. Z is CH ２ , CHR １１ and CR １２ R １３ and R １１ , R １２ and R １３ is each independently selected from the group consisting of alkyl, alkoxy, aryl and heteroaryl, preferably H or alkyl, and / or n is 1.

12. below: 【Transformation 3】 【Chemistry 4】 2. The compound of claim 1 selected from the group consisting of:

13. 13. An optoelectronic component (10) comprising a first electrode (2), a second electrode (6) and a layer system (7) arranged between the first electrode (2) and the second electrode (6), characterized in that at least one layer of the layer system (7) comprises at least one compound according to any one of claims 1 to 12.

14. 14. The optoelectronic component (10) according to claim 13, comprising 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) comprises the at least one compound, and wherein the optoelectronic component (10) is preferably an organic photovoltaic element, an OFET (organic field-effect transistor), an OLED (organic light-emitting diode) or an organic photodetector.

15. Use of a compound according to any one of claims 1 to 12 in an optoelectronic component (10), preferably an organic photovoltaic device, an OFET (organic field effect transistor), an OLED (organic light emitting diode) or an organic photodetector.

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