Organic semiconductor compound having indole group, organic optoelectronic component comprising that type of compound, and use of that type of compound

Abstract

To provide a compound useful as a material for an optoelectronic component.SOLUTION: The invention relates to a compound represented by Formula III or IV, where X and Z are each O, and R2 and R3 are each independently an electron-withdrawing alkyl group having a C-C double bond substituted with two cyano groups.SELECTED DRAWING: Figure 2

Description

Technical Field

[0001] The present invention relates to compounds of general formula I, optoelectronic components containing such compounds, and the use of such compounds in optoelectronic components.

Background Art

[0002] Circuits made from electrically conductive polymers or small organic molecules are used in organic electronics. Organic optoelectronic components can be, for example, displays, data storage means, or transistors. These components also include organic optoelectronic components, especially organic optoactive components, especially solar cells and photodetectors having an optoactive layer in which incident electromagnetic radiation results in the generation of charge carriers, especially electron-hole pairs (excitons) bound to each other.

[0003] Optoactive optoelectronic components utilize the photoelectric effect to enable the conversion of electromagnetic radiation into an electric current. Such conversion of electromagnetic radiation requires absorber materials that exhibit good absorbability. Further optoelectronic components are light-emitting electroluminescent components that emit light when an electric current flows through them. Optoelectronic components include at least two electrodes, one electrode being applied to a substrate and the other electrode functioning as a counter electrode. Between the electrodes, there is at least one optoactive layer, preferably an organic optoactive layer. Further layers, such as charge carrier transport layers, can additionally be arranged between the electrodes.

[0004] Numerous absorber materials for organic solar cells are known from the prior art.

[0005] Patent Document 1 of the international patent application discloses an organic compound which is an organic compound characterized by strong absorption in the short-wave spectral region of visible light. The use of this compound for organic electronic components and a method for preparing this compound are also disclosed.

[0006] Patent Document 2 of the international patent application discloses an organic semiconductor material and its use in organic components. Since this organic material can function as a functional component in organic electronic components, it can bring about improved absorption in organic solar cells or has an increased charge carrier mobility.

[0007] The absorber materials disclosed in the prior art are suitable for the light-active layer of organic solar cells. However, in particular, in order to make organic solar cells (OPVs) competitive with conventional silicon-based solar cells, it is necessary to improve the efficiency of the absorber materials. Specific drawbacks resulting from the prior art are, in particular, in the region of 0.9 V or more, preferably in the region of 0.94 V or more, or preferably in the region of 0.95 V or more, especially in the region of 1 V, in constructing a solar cell having an open-circuit voltage Uoc, especially in the blue / green region of visible light, the efficiency of the absorber material having a high absorption coefficient is not appropriate. In particular, at wavelengths in the region of 500 - 600 nm, the absorption of known organic compounds of small molecules, especially absorber molecules, for organic optoelectronic components is not appropriate. This effect means that photons within this wavelength range cannot be utilized sufficiently.

[0008] The search for semiconductor organic materials that, when used in organic optoelectronic components, bring about an improvement in the properties of these components, especially the absorption of electromagnetic radiation, is continuing.

Prior Art Documents

Patent Documents

[0009]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0010] Accordingly, an object of the present invention is to provide an organic compound having improved absorbency suitable for use in organic optoelectronic components, an optoelectronic component containing at least one such compound, and the use of such a compound in an optoelectronic component, provided that the listed drawbacks do not occur, specifically, the absorption of electromagnetic radiation is improved and / or the efficiency of an organic solar cell is increased.

Means for Solving the Problems

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

[0012] This object is, in particular, of the general formula I

Chemical Formula

Chemical Formula

[0013] Specifically, the present invention relates to an A-D-A dye of a compound of general formula I, where the central structural unit is an indole unit. The presence of a furan group or a thiophene group (specifically on the indole unit) and the presence of at least one double bond on the furan group or the thiophene group (preferably arranged in proximity to at least one electron-withdrawing group) improve the properties of the absorber material.

[0014] In a preferred embodiment of the present invention, group Ia and / or group Ib have at least one electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F), and particularly preferably, group Ia and group Ib have at least one electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F).

[0015] In a preferred embodiment of the present invention, R9 and R10 are not homocyclically or heterocyclically bonded to each other in the form of a ring structure.

[0016] In a preferred embodiment of the present invention, R5 and R6 are not homocyclically or heterocyclically bonded to each other in the form of a ring structure.

[0017] In a preferred embodiment of the present invention, the central indole unit, particularly the pyrrole ring of the indole unit, does not have any further fused aromatic system.

[0018] In a preferred embodiment of the present invention, the pyrrole ring is a fused unit containing furan, particularly benzofuran.

[0019] Substitution is specifically understood to mean the substitution of H by a substituent. A substituent specifically means all atoms and atomic groups other than hydrogen, preferably a halogen group, an alkyl group (where the alkyl group may be linear or branched), an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, an aryl group, or a heteroaryl group. Halogen specifically means F, Cl, or Br, preferably F.

[0020] In a preferred embodiment of the present invention, the carbon atoms in the alkyl group are not replaced at all by heteroatoms.

[0021] In a preferred embodiment of the present invention, R2 and R3 are not hydrogen atoms.

[0022] In a preferred embodiment of the present invention, either A1 or A4 is not a hydrogen atom. In a particularly preferred embodiment of the present invention, A1 and A4 are hydrogen atoms.

[0023] A heteroatom, particularly the heteroatom in general formula I, specifically means an atom selected from the group consisting of O, S, Se, Si, B, N, and P, preferably an atom selected from the group consisting of O, S, Se, and N.

[0024] In an alternatively preferred embodiment, the central indole unit, in particular the pyrrole ring of the indole unit, has at least one fused homo- or hetero-cyclic ring structure.

[0025] In a preferred embodiment of the present invention, the ring structure formed between R5 and R6 and / or between R9 and R10 has at least one double bond and is preferably aromatic.

[0026] The compounds of the present invention are in particular small molecules. A small molecule is specifically understood to mean a non-polymeric organic molecule having a monodisperse molar mass of 100 to 2000 g / mol that exists in the solid phase at standard pressure (the air pressure of the ambient atmosphere) and room temperature. Specifically, a small molecule is photoactive, and "photoactive" is understood to mean that the molecule undergoes a change in its charged state and / or polarization state when light is supplied. A specific characteristic of a photoactive molecule is the absorption of electromagnetic radiation within a defined wavelength range that involves the conversion of the absorbed electromagnetic radiation, i.e., photons, into excitons.

[0027] In a preferred embodiment of the present invention, the aryl groups and heteroaryl groups of general formulas I, II, III, IV, V, VI, VII, and / or VIII are C5-C10 aryl groups and C5-C10 heteroaryl groups.

[0028] In a preferred embodiment of the present invention, Y1, Y2, Y3, and Y4 are each independently selected from the group consisting of N, CH, CF, C-CH3, C-CF3, C-C2H5, C-C3H8, C-OCH3, C-OC2H5, C-SCH3, C-SC2H5.

[0029] In a preferred embodiment of the present invention, the cyclic or acyclic alkyl groups of the compounds of the present invention are linear or branched, and the alkyl groups are preferably C1-C5 alkyl groups.

[0030] In a preferred embodiment of the present invention, at least one of positions Y1, Y2, 3, and Y4 is N, preferably at least one of positions Y1 or Y2 is N, and / or at least one of positions Y3 or Y4 is N. Thereby, in particular, a decrease in the highest occupied molecular orbital (HOMO) associated with a shift in the absorption spectrum of the compound of the present invention towards shorter wavelengths is achieved.

[0031] In a particularly preferred embodiment of the present invention, Y1, Y2, Y3, and Y4 are each CH. In this case, the two 5-membered rings are each a furan ring with or without further substitution.

[0032] The compounds of the present invention have advantages compared to the prior art. Advantageously, the compounds of the present invention have surprisingly good absorption properties in a relatively broad spectral region of visible light from 500 to 700 nm, and specifically, surprisingly high absorption was observed in the spectral region of about 500 to 700 nm. Advantageously, absorber materials are provided that have improved absorption within the wavelength range of the blue / green region of visible light. Surprisingly, the central structural unit of the compounds of the present invention, namely the central indole unit, is very suitable for obtaining compounds with the desired absorbability. The compounds of the present invention advantageously have sufficient thermal, chemical, and electrochemical stability to meet the requirements typically demanded in the manufacture and operation of photoactive organic electronic components. Specifically, this compound can be easily evaporated under reduced pressure, especially without residues. Advantageously, the compounds of the present invention have charge carrier transport properties and are thus suitable for use in organic optoelectronic components, especially organic solar cells. Advantageously, this compound has very good transport properties and, in particular, has particularly suitable energy levels. Surprisingly, it has been found that the compounds of the present invention have particularly good absorption of electromagnetic radiation, especially light in the visible spectral region, due to the central structural element of the indole unit. For this reason, in particular, the efficiency of organic optoelectronic components increases and / or the charge carrier mobility in the photoactive layer increases. Advantageously, the compounds of the present invention have a high absorption coefficient. Advantageously, the open-circuit voltage Uoc is greater than 0.9 V, preferably greater than 0.94 V, and particularly preferably greater than 0.95 V.

[0033] In one development form of the present invention, the compound has the general formula II [Chemical formula] (wherein R1 is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl, R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy, and alkyl, and X and Z are each independently O or S) and is a compound of

[0034] In one development form of the present invention, the compound has the general formula VII [Chemical formula] (wherein R1 is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl, R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy, and alkyl, and Z is O or S, provided that A1 or A4 is preferably a hydrogen atom) and is a compound of

[0035] In a preferred embodiment of the present invention, at least two of A1, A2, A3, or A4 are each independently a group Ia [Chemical formula] and the other A1, A2, A3, or A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and amino.

[0036] In one development form of the present invention, at least one of A1, A2, A3, or A4 is independently [Chemical formula] (In the formula, R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or acyclic alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be substituted by CN or F), R3 is preferably an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be substituted by CN or F), R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, and aryl (wherein H may be substituted in each case), R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, aryl (wherein H may be substituted in each case), provided that R9 and R10 may be bonded to each other homocyclically or heterocyclically in the form of a ring structure) is.

[0037] In a preferred embodiment of the present invention, at least two of the groups A1, A2, A3, or A4 are each independently

Chemical formula

[0038] In one development form of the present invention, the compound has the general formula III and / or IV [Chemical formula] (wherein R1 is H or alkyl, X and Z are each independently O or S, A1, A3, and A4, or A1, A2, and A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl, R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be optionally substituted by CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be optionally substituted by CN or F), provided that preferably X and Z are O, R4 is H, and R5 and R6 are H) is the compound.

[0039] In a preferred embodiment of the present invention, the compound has the general formula X [Chemical formula] (wherein R1 is H or alkyl, X and Z are each independently O or S, A2, A3, and A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl, R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be substituted by CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one C-C double bond (wherein H may be substituted by CN or F). However, preferably, X and Z are O, R4 is H, and R5 and R6 are H) is a compound of.

[0040] In a preferred embodiment of the present invention, in the compound of general formula X, A2, A3, and A4 are each H.

[0041] In a preferred embodiment of the present invention, the compound has the general formula XI

Chemical formula

[0042] In a preferred embodiment of the present invention, in the compound of general formula XI, A1, A2, and A3 are each H.

[0043] In a preferred embodiment of the present invention, the compound of general formula I has N at positions Y1 and / or Y2 of formula Ia and / or at positions Y3 and / or Y4 of formula IIa.

Chemical formula

[0044] As a result, in particular, the resulting optical properties, especially light absorption, are more advantageous than those of equivalent compounds having atoms other than O.

[0045] In one development form of the present invention, in formula III, A1, A3, and A4 are H (formula V), and in formula IV, A1, A2, and A4 are H (formula VI)

Chemical formula

[0046] In one development form of the present invention, the compound is of general formula VIII and / or IX

Chemical formula

[0047] In a preferred embodiment of the present invention, the compound has the general formula XII [Chemical formula] (wherein R1 is H or alkyl, X and Z are each independently O or S, R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, aryl (wherein H may be optionally substituted in each case), R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, aryl (wherein H may be optionally substituted in each case), provided that R9 and R10 may be bonded to each other homocyclically or heterocyclically in the form of a ring structure, R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, aryl (wherein H may be optionally substituted in each case), R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, aryl (wherein H may be optionally substituted in each case), provided that R5 and R6 may be bonded to each other homocyclically or heterocyclically in the form of a ring structure, However, preferably, R5 and R6 are H, and R9 and R10 are H. Here, R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F), preferably, R3 is an electron-withdrawing alkyl group having at least one C-C double bond, and R2 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or acyclic alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F), preferably, R2 is an electron-withdrawing alkyl group having at least one C-C double bond) is a compound of

[0048] In a preferred embodiment of the present invention, X and / or Z is O, where the structure is especially a substituted furan ring. Preferably, at least one furan ring in the groups A1, A2, A3, A4, or A5 on the central indole unit increases the absorption by the compound.

[0049] In a preferred embodiment of the present invention, group A5 is the same as at least one of groups A1, A2, A3, and A4.

[0050] In a preferred embodiment of the present invention, R4 is H, methyl, propyl, or isopropyl, and when X and Z are O, R4 is H, and R5 and R6 are H.

[0051] In a preferred embodiment of the present invention, R2 in group Ib has an electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F), and / or R3 in group Ia has an electron-withdrawing alkyl group having at least one C-C double bond (where H may be substituted by CN or F).

[0052] In a preferred embodiment of the present invention, R2 and / or R3 have at least two C-C double bonds.

[0053] In one development form of the present invention, R2 and R3 are each independently

Chemical formula

[0054] In a preferred embodiment of the present invention, R2 and / or R3 are each independently in each case

Chemical formula

[0055] In a further development form of the present invention, R2 and R3 are each independently [Chemical formula] (wherein * represents attachment to a group of general formula Ia and / or Ib, provided that R2 and R3 are preferably the same) is selected from the group consisting of.

[0056] In one development form of the present invention, the compound is [Chemical formula] [Chemical formula] [Chemical formula] is selected from the group consisting of.

[0057] In one development form of the present invention, the compound is F7 and / or F16 [Chemical formula] is.

[0058] In a preferred embodiment of the present invention, X is the same as Z, R2 is the same as R3, R5 is the same as R9, and R6 is the same as R10.

[0059] In a preferred embodiment of the present invention, the compound of general formula I additionally has a 5-membered or 6-membered ring formed by R5 and R6 and / or R9 and R10, and this 5-membered or 6-membered ring may be further substituted at additional positions.

[0060] Organic single or tandem cells are known from the prior art. The German Patent Application Publication No. 102004014046 A1 discloses a photovoltaic component, in particular a solar cell, consisting of organic layers of one or more pi, ni, and / or pin diodes stacked on top of each other. The International Patent Application Publication No. 201116108 A1 pamphlet discloses a photovoltaic component having at least two photovoltaic layer systems, at least two different transport layer systems of the same type of charge carrier between the photovoltaic layer systems, and at least one organic layer system disposed between the electrodes, the photovoltaic component having an electrode and a counter electrode, wherein one transport layer system is matched to the energy of one of the two photovoltaic layer systems and the other transport layer system is transparent.

[0061] The object of the present invention is also achieved by providing a optoelectronic component containing at least one compound of the present invention, in particular one according to one of the above exemplary embodiments. In the optoelectronic component, this brings the advantages already revealed, in particular in connection with the compounds of the present invention. The optoelectronic component includes a first electrode, a second electrode, and a layer system disposed between the first electrode and the second electrode. Characteristically, at least one layer of the layer system contains at least one compound of the present invention.

[0062] The efficiency of an optoelectronic component, in particular an organic optoelectronic component, depends on factors including the absorption characteristics of the compound, i.e., the absorber material. Here, advantageous properties are, in particular, high absorption and absorption in a wide region of the available spectrum of electromagnetic radiation, so that photons of various wavelengths can be used for power generation.

[0063] Optoelectronic components, in particular organic optoelectronic components, are specifically understood to mean components containing organic conductor or semiconductor materials, in particular transistors, light-emitting organic components, organic photovoltaic devices, photodetectors, or organic solar cells. A solar cell containing at least one compound of the present invention enables particularly efficient utilization of the short-wave spectrum of visible light.

[0064] An organic photovoltaic device (OPV) specifically means a photovoltaic device having at least one organic photoactive layer comprising at least one compound of the present invention. A photoactive organic optoelectronic component enables the conversion of electromagnetic radiation, for example within the visible light wavelength range, into an electric current by utilizing the photovoltaic effect. The conversion requires an organic semiconductor material that exhibits sufficiently good absorbency.

[0065] In a preferred embodiment of the present invention, the optoelectronic component is a solar cell, FET, LED, or photodetector, preferably an organic solar cell (OPV), OFET, OLED, or organic photodetector.

[0066] Here, the organic electronic component includes an electrode and a counter electrode together with an organic photoactive layer disposed between the electrodes. This organic photoactive layer has important functions for the optoelectronic component, specifically charge carrier transport functions such as hole transport (p-conductivity) or electron transport (n-conductivity). The organic photoactive layer is specifically a photoactive layer in which excitons (electron-hole pairs) are formed by the radiation of visible light, UV rays, and / or IR rays. The organic material is applied in the form of a thin film or in small amounts by printing, glue bonding, coating, vapor deposition, or other forms on a foil. All processes used for electronic components on glass, ceramic, or semiconductor substrates can similarly be used for the production of thin layers.

[0067] In one development form of the present invention, the layer system has at least one photoactive layer, preferably an absorber layer, and at least one photoactive layer contains at least one compound of the present invention. In a preferred embodiment of the present invention, the photoactive layer is disposed between a first electrode and a second electrode.

[0068] In one development form of the present invention, the layer system has at least two photoactive layers, preferably at least three photoactive layers, or preferably at least four photoactive layers, preferably absorber layers.

[0069] In a preferred embodiment of the present invention, the organic solar cell has a photoactive layer that contains at least one organic donor material in contact with at least one organic acceptor material, and the donor material and the acceptor material form a donor-acceptor heterojunction, specifically a so-called bulk heterojunction (BHJ), and the photoactive layer contains at least one compound of the present invention.

[0070] In a preferred embodiment of the present invention, the optoelectronic component includes at least one additional layer, preferably at least one charge transport layer, especially an electron transport layer and / or a hole transport layer.

[0071] In a preferred embodiment of the present invention, at least one charge transport layer, especially at least one electron transport layer and / or at least one hole transport layer, contains at least one compound of the present invention.

[0072] In a preferred embodiment of the present invention, the organic solar cell is a single cell, or a tandem, triple, quadruple, or other multiple cell.

[0073] A tandem cell specifically preferably means that two functional cells are spatially stacked and sequentially connected between a first electrode and a second electrode, provided that one or more intermediate layers may be disposed between the cells. Therefore, a multiple cell or a multi-junction cell is understood to mean that more than two functional cells are spatially stacked and sequentially connected, provided that an intermediate layer may be arranged between the cells.

[0074] In a preferred embodiment of the present invention, the optoelectronic component includes a substrate together with a layer system disposed on the substrate between a first electrode and a second electrode, specifically, one of the electrodes of the optoelectronic component may be directly applied to the substrate.

[0075] In one development form of the present invention, the photoactive layer takes the form of a mixed layer of at least one compound of the present invention and at least one further compound, or a mixed layer of at least one compound of the present invention and at least two further compounds, and preferably, the compound is an absorber material.

[0076] In a preferred embodiment of the present invention, the optoelectronic component takes the form of a nip, ni, ip, pnip, pni, pip, nipn, nin, ipn, pnipn, or pipn cell, or a combination of nip, ni, ip, pnip, pni, pip, nipn, nin, ipn, pnipn, or pipn cells containing at least one i layer.

[0077] The i layer is specifically understood to mean an intrinsic undoped layer. One or more i layers can consist of a mixture of two or more materials called a bulk heterojunction (BHJ) having a mutual penetration network, or else a single material (planar heterojunction, PHJ).

[0078] In a preferred embodiment, the compound of the present invention and / or a layer containing at least one compound of the present invention can be deposited using vacuum treatment, vapor deposition, or solvent treatment, and particularly preferably using vacuum treatment.

[0079] The object of the present invention is also achieved by providing the use of the compound of the present invention in an optoelectronic component, preferably an organic optoelectronic component, specifically one according to one of the above examples. The use of the compound of the present invention in an optoelectronic component brings about the advantages already revealed in connection with the compound of the present invention and an optoelectronic component containing at least one compound of the present invention.

[0080] In a preferred embodiment of the present invention, the optoelectronic component, preferably an organic optoelectronic component, is an organic solar cell.

[0081] Hereinafter, some specific examples of the compounds of the present invention and their optical properties are described. Table 1 shows an overview of the melting points and absorption maxima (in nm and eV units in solvent (SO)) of such compounds of the present invention. The relevant absorption spectra of the compounds listed in Table 1 are shown in Figures 3 to 15. The spectral data relate to a vacuum vapor deposition layer on quartz glass having a thickness of 30 nm.

[0082] [Table 1]

[0083] TIFF2025093915000025.tif234170

[0084] TIFF2025093915000026.tif78170

[0085] The optical properties were determined experimentally. The absorption maximum λmax was determined in a dilute solution in a cuvette in dichloromethane using a photometer. The measured absorption maxima of all the compounds described are 530 - 610 nm.

[0086] It is noteworthy that the compounds of the present invention have particularly strong absorption within a broad spectrum of visible light. Therefore, the compounds of the present invention enable the absorption of photons over a relatively broad spectral region including a high proportion of short - wave visible sunlight and the conversion of its electrical energy.

[0087] Since the compounds of the present invention have particularly good radiation absorption rates, it can be inferred from the absorption spectra in Table 1 that they have a relatively high optical concentration integral value in the visible spectral region. Here, the "integral value" means the area under the curve of the absorption spectrum, which is an important characteristic of the suitability of the material as a light - active material.

[0088] Table 2 shows a direct comparison of various parameters of the compounds of the present invention. The photovoltaic parameters of open - circuit voltage Uoc, short - circuit current Jsc, and fill factor FF relate to the same structure of the solar cell in each case.

[0089] For the inspection of the compounds of the present invention, i.e., their use as absorber materials in organic optoelectronic components, under AM1.5 illumination (AM = air mass, AM = 1.5, in this spectrum the total radiant power is 1000 W / m 2 , AM = 1.5) which is the standard value for solar module measurements), in a BHJ cell with a glass having a structure: ITO / C60(15 nm) / compound of the present invention (absorber material):C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm), the current-voltage curve of the photoactive layer was measured with the bulk heterojunction (BHJ). A transparent cover contact made of ITO (indium tin oxide) is applied to the glass substrate. Here, ITO functions as an electrode, the adjacent fullerene C60 functions as an electron transport layer (ETL), in contact with which are a photoactive C60 layer as an electron acceptor material and each compound of the present invention as a hole acceptor material (donor material), followed by BPAPF (9,9-bis[4-(N,N-bis(biphenyl-4-yl)amino)phenyl]-9H-fluorene) as a hole transport layer (HTL) and BPAPF doped with NDP9 (Novaled AG), and then an electrode made of aluminum (see Figure 2).

[0090] The advantageous synergistic effect of the compounds of the present invention having a furan group or a thiophene group due to the interaction with the indole unit is shown in Table 2.

[0091]

Table 2

[0092] Particularly advantageous properties of the compounds of the present invention are also demonstrated by the photovoltaic parameters of open circuit voltage Uoc, short circuit current Jsc, and fill factor FF in the same solar cell structure. The compounds of the present invention are suggested to have not only improved absorbability but also excellent charge carrier transportability by the increase in the fill factor FF. Depending on the charge transportability and absorbability, a high photocurrent can be achieved with a good fill factor. Therefore, it is possible to manufacture tandem / triple / quadruple or multi-junction solar cells that are very well combined. Among the compounds shown in Table 2, compounds F3, F4, F6, F8, F9, and F13 have the highest optical properties. Furthermore, in particular, in these compounds, the highest cell efficiency (eff), that is, the highest efficiency, of the organic solar cells produced therefrom is achieved. Among these compounds, F6 and F9 have the highest efficiency in solar cells. These compounds each have a furan ring and / or a thiophene ring, particularly one furan ring each, on the 5-membered ring and the 6-membered ring of the central indole unit. In addition, an H or a methyl group, an ethyl group, a propyl group, or a butyl group, particularly an isopropyl group, an isobutyl group, or an s-butyl group on the N of the pyrrole ring of the central indole unit is advantageous. Preferably, additional 5-membered rings (Ia, IIa) are attached to the 2'-position and 6'-position of the central indole unit. The two outer 5-membered rings (Ia, IIa) preferably each have a dicyanovinyl group and / or a butadienyldicyano group.

[0093] The present invention will be described in more detail hereinafter with reference to the drawings. The figures show the following.

Brief Description of the Drawings

[0094]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Figure 11

Figure 12

Figure 13

Figure 14

Figure 15

Embodiments for Carrying Out the Invention

[0095] Examples Figure 1 shows an example of a synthetic scheme for the synthesis of the compounds of the present invention.

[0096] The general preparation of the compounds of the present invention is known to those skilled in the art from the prior art. In this regard, in particular, refer to International Publication Pamphlet No. WO 2017 / 114937 A1 and International Publication Pamphlet No. WO 2017 / 114938 A1 of the international application.

[0097] Figure 1 shows the general synthesis of the compounds of the present invention. Thus, Compounds F2, F3, F4, F5, F6, F8, F9, F10, F11, F12, F14, F15, F17, and F18 can be obtained simply and in good yields. Compounds F1, F7, F13, and F16 are prepared by the syntheses disclosed in International Publication Pamphlet No. WO 2017 / 114937 A1 and International Publication Pamphlet No. WO 2017 / 114938 A1 of the international application. The linking positions of the substituents (Ia, IIa) to the central indole unit are summarized in Table 3.

[0098]

Table 3

[0099] General formula I

Chem.

Chem.

Chemical formula

[0100] In one configuration of the present invention, the compound is of general formula II

Chemical formula

[0101] In a further configuration of the present invention, the compound is of general formula VII

Chemical formula

[0102] In a further configuration of the present invention, at least one of A1, A2, A3, or A4 is independently

Chemical formula

[0103] In a further configuration of the present invention, the compound is of general formula III and / or IV

Chemical formula

[0104] In a further configuration of the present invention, in formula III, A1, A3, and A4 are H (formula V), and in formula IV, A1, A2, and A4 are H (formula VI)

Chemical formula

[0105] In a further configuration of the present invention, the compound is of general formula VIII and / or IX

Chemical formula

[0106] In a further configuration of the present invention, R2 and R3 are each independently

Chemical formula

[0107] In a further configuration of the present invention, R2 and R3 are each independently [Chemical formula] (wherein * represents attachment to a group of general formula Ia and / or Ib, provided that R2 and R3 are preferably the same) selected from the group consisting of

[0108] In a further configuration of the present invention, the compound is [Chemical formula] [Chemical formula] [Chemical formula] selected from the group consisting of

[0109] In a further configuration of the present invention, the compound is F7 and / or F 16 [Chemical formula] is.

[0110] Figure 2 shows a schematic cross-sectional view of an embodiment of an optoelectronic component.

[0111] The optoelectronic component includes a first electrode 1, a second electrode 2, and a layer system 7, and the layer system 7 is disposed between the first electrode 1 and the second electrode 2. At least one layer of the layer system 7 contains at least one compound of the present invention.

[0112] In one configuration of the present invention, the optoelectronic component is an organic solar cell, an OFET, an OLED, or an organic photodetector.

[0113] The structures of organic solar cells known from the prior art consist of pin or nip diodes (Martin Pfeiffer, “Controlled doping of organic vacuum deposited dye layers: basics and applications”, Ph.D. thesis TU - Dresden, 1999 and WO 2011 / 161108 A1 pamphlet). A pin solar cell consists of a substrate (usually in contact with a transparent base contact), a p - layer, an i - layer, an n - layer, and a top contact. A nip solar cell consists of a substrate (usually in contact with a transparent base contact), an n - layer, an i - layer, a p - layer, and a top contact.

[0114] In this example, the optoelectronic component is a solar cell. The solar cell has, for example, a substrate 1 made of glass, on which there is an electrode 2 containing, for example, ITO. On top of that, an electron transport layer 3 (ETL) and a light - active layer 4 containing at least one p - conductive donor material and one n - conductive acceptor material, such as C60 fullerene, of the compounds of the present invention, either in a planar heterojunction or a bulk heterojunction, are disposed. On top of that, a p - doped hole transport layer 5 (HTL) and an electrode 6 made of aluminum are disposed.

[0115] In a further configuration of the present invention, the layer system 7 has at least one light - active layer 4, preferably an absorber layer, and at least one light - active layer 4 contains at least one compound of the present invention.

[0116] In a further configuration of the present invention, the layer system 7 has at least two light - active layers, preferably at least three light - active layers, or preferably at least four light - active layers.

[0117] In a further configuration of the present invention, the light - active layer takes the form of a mixed layer of at least one compound of the present invention and at least one further compound, or a mixed layer of at least one compound of the present invention and at least two further compounds, and the compounds are preferably absorber materials.

[0118] In a further configuration of the present invention, the optoelectronic component has further functional layers, which are, inter alia, in the form of tandem cells, triple cells, or multiple cells.

[0119] The following Figures 3 to 15 give specific examples of the compounds of the present invention and their optical properties.

[0120] Figure 3 shows a graph (A) of the absorption spectrum of compound F1, and graphs (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound F1, measured in an organic optoelectronic component in the form of an organic solar cell.

[0121] The absorption spectra (optical density against wavelength in nm) were measured for vacuum-deposited layers 30 nm thick of the respective compounds F1 to F13 on quartz glass.

[0122] The current-voltage curve includes indicators characterizing the organic solar cell. The most important indicators here are the fill factor FF, the open-circuit voltage Uoc, and the short-circuit current Jsc.

[0123] In a specific case, the BHJ cell on the ITO layer has a C60 layer with a thickness of 15 nm. Compound F1 was applied to this layer together with C60 at a thickness of 30 nm. Following this layer is a BPAPF layer with a thickness of 10 nm, and on top of that, there is a further layer with a thickness of 30 nm containing BPAPF and NDP9. The proportion of BPAPF in this layer is 10 weight percent based on the entire layer. This layer is in contact with a further layer with a thickness of 1 nm containing NDP9, followed by an aluminum layer with a thickness of 100 nm. Using a photoactive layer characterized by a bulk heterojunction (BHJ), the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F1:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F1, the fill factor FF is 62.7%, the open-circuit voltage Uoc is 0.83 V, and the short-circuit current Jsc is 10.8 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F1 is 5.62%.

[0124] Compound F1 further exhibits particularly good evaporability at temperatures up to a final temperature of 240 °C to 255 °C.

[0125] Figure 4 shows a graph (A) of the absorption spectrum of compound F2, and graphs (B) of the current-voltage curve, spectral external quantum efficiency, and fill factor of a BHJ cell containing compound F2 measured in an organic optoelectronic component in the form of an organic solar cell.

[0126] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F2:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F2, the fill factor FF is 61.7%, the open-circuit voltage Uoc is 1.02 V, and the short-circuit current Jsc is 8.0 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F2 is 5.03%.

[0127] Figure 5 shows a graph (A) of the absorption spectrum of compound F3 and graphs (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound F3 measured in an optoelectronic component in the form of an organic solar cell.

[0128] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F3:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F3, the fill factor FF is 73.8%, the open-circuit voltage Uoc is 0.98 V, and the short-circuit current Jsc is 11.5 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F3 is 8.32%. F3 exhibits particularly good transport properties together with a high fill factor FF.

[0129] Figure 6 shows a graph (A) of the absorption spectrum of compound F4 and graphs (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound F4 measured in an optoelectronic component in the form of an organic solar cell.

[0130] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F4:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F4, the fill factor FF is 72.1%, the open-circuit voltage Uoc is 0.94 V, and the short-circuit current Jsc is 11.9 mA / cm2. The cell efficiency of this type of optoelectronic component, especially the solar cell, containing compound F4 is 8.07%.

[0131] Figure 7 shows a graph (A) of the absorption spectrum of compound F5, and graphs (B) of the current-voltage curve, spectral external quantum efficiency, and fill factor of a BHJ cell containing compound F5, measured in an optoelectronic component in the form of an organic solar cell.

[0132] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F5:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F5, the fill factor FF is 62.3%, the open-circuit voltage Uoc is 1.01 V, and the short-circuit current Jsc is 7.7 mA / cm2. The cell efficiency of this type of optoelectronic component, especially the solar cell, containing compound F5 is 4.85%.

[0133] Figure 8 shows a graph (A) of the absorption spectrum of compound F6, and graphs (B) of the current-voltage curve, spectral external quantum efficiency, and fill factor of a BHJ cell containing compound F6, measured in an optoelectronic component in the form of an organic solar cell.

[0134] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / Compound F6:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing Compound F6, the fill factor FF is 72.5%, the open-circuit voltage Uoc is 0.96 V, and the short-circuit current Jsc is 13.8 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing Compound F6 is 9.60%.

[0135] Figure 9 shows a graph (A) of the absorption spectrum of Compound F7, and graphs (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing Compound F7, measured in an optoelectronic component in the form of an organic solar cell.

[0136] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F7:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing Compound F7, the fill factor FF is 63.6%, the open-circuit voltage Uoc is 1.0 V, and the short-circuit current Jsc is 9.8 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing Compound F1 is 6.23%.

[0137] Figure 10 shows a graph (A) of the absorption spectrum of Compound F8, and graphs (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing Compound F8, measured in an optoelectronic component in the form of an organic solar cell.

[0138] Using a bulk heterojunction (BHJ) as the light-active layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F8:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F8, the fill factor FF is 67.9%, the open-circuit voltage Uoc is 0.98 V, and the short-circuit current Jsc is 12.8 mA / cm2. The cell efficiency of this type of optoelectronic component, especially the solar cell, containing compound F8 is 8.52%. Compound F8 shows particularly stable behavior under vacuum deposition.

[0139] Figure 11 shows a graph (A) of the absorption spectrum of compound F9 and a graph (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound F9 measured in an organic optoelectronic component in the form of an organic solar cell.

[0140] Using a bulk heterojunction (BHJ) as the light-active layer, the current-voltage curve of a BHJ cell with the structure: ITO / C60(15 nm) / F9:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F9, the fill factor FF is 70.3%, the open-circuit voltage Uoc is 0.98 V, and the short-circuit current Jsc is 13.6 mA / cm2. The cell efficiency of this type of optoelectronic component, especially the solar cell, containing compound F9 is 9.37%.

[0141] Figure 12 shows a graph (A) of the absorption spectrum of compound F10 and a graph (B) of the current-voltage curve, spectral external quantum yield, and fill factor of a BHJ cell containing compound F10 measured in an organic optoelectronic component in the form of an organic solar cell.

[0142] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F10:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F10, the fill factor FF is 56.5%, the open-circuit voltage Uoc is 1.01 V, and the short-circuit current Jsc is 11.8 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F1 is 6.73%.

[0143] Figure 13 shows a graph (A) of the absorption spectrum of compound F11, and graphs (B) of the current-voltage curve, spectral external quantum efficiency, and fill factor of a BHJ cell containing compound F11, measured in an optoelectronic component in the form of an organic solar cell.

[0144] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F11:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F11, the fill factor FF is 56.7%, the open-circuit voltage Uoc is 0.98 V, and the short-circuit current Jsc is 11.3 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F11 is 6.28%.

[0145] Figure 14 shows a graph (A) of the absorption spectrum of compound F12, and graphs (B) of the current-voltage curve, spectral external quantum efficiency, and fill factor of a BHJ cell containing compound F12, measured in an optoelectronic component in the form of an organic solar cell.

[0146] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F12:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F12, the fill factor FF is 50.7%, the open-circuit voltage Uoc is 1.03 V, and the short-circuit current Jsc is 8.9 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F12 is 4.65%.

[0147] Figure 15 shows a graph of the spectral external quantum yield and fill factor of a BHJ cell containing compound F13, measured in an organic optoelectronic component in the form of an organic solar cell.

[0148] Using a bulk heterojunction (BHJ) as the photoactive layer, the current-voltage curve of a BHJ cell having the structure: ITO / C60(15 nm) / F13:C60(30 nm, 3:2, 50 °C) / BPAPF(10 nm) / BPAPF:NDP9(30 nm, 10 wt% NDP9) / NDP9(1 nm) / Al(100 nm) was determined. In the optoelectronic component containing compound F13, the fill factor FF is 70.3%, the open-circuit voltage Uoc is 0.87 V, and the short-circuit current Jsc is 12.2 mA / cm2. The cell efficiency of this type of optoelectronic component, especially a solar cell, containing compound F13 is 7.46%.

[0149] The compounds of the present invention are very suitable for use in organic solar cells and other organic optoelectronic components, and in particular, enabling an open-circuit voltage Uoc of more than 0.9 V is demonstrated from the experimental data of compounds F1 to F13 including the absorbability of the compounds and the current-voltage curves measured in organic solar cells.

Claims

1. Compounds of general formula III and / or IV 【Chemistry 7】 (In the formula, R １ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl; R ４ is selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open chain alkyl, amino, aryl, and alkenyl; X and Z are each O; A １ , A ３ , and A ４ , or A １ , A ２ , and A ４ are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl; R ９ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, aryl, where H in each case may be optionally substituted; R １０ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; However, R ９ and R １０ may be homocyclically or heterocyclically linked to each other in the form of a ring structure. R ５ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; R ６ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; provided that R5 and R6 may be homocyclically or heterocyclically bonded to each other in the form of a ring structure; and R ２ and R ３ are each independently 【Chemistry 13】 (In the formula, ＊ indicates a bond to the group of general formula III and / or IV) is selected from the group consisting of:

2. R ４ is H, and R ５ and R ６ The compound of claim 1 , wherein

3. In formula III, A １ , A ３ and A ４ is H (shown as formula V); In formula IV, A １ , A ２ and A ４ is H (shown as Formula VI); The compound of claim 1. 【Chemistry 8】

4. R ５ and R ６ The compound of claim 3 , wherein

5. Compounds of general formula X and / or XI 【Chemistry 9】 【Chemistry 10】 (In the formula, R １ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl; R ４ is selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open chain alkyl, amino, aryl, and alkenyl; X and Z are each independently O or S; A １ , A ３ , and A ４ , or A １ , A ２ , and A ４ are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl; R ９ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, aryl, where H in each case may be optionally substituted; R １０ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; However, R ９ and R １０ may be homocyclically or heterocyclically linked to each other in the form of a ring structure. R ５ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; R ６ is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open chain alkyl, alkenyl, and aryl, where H, in each case, may be substituted; provided that R5 and R6 may be homocyclically or heterocyclically bonded to each other in the form of a ring structure; and R ２ and R ３ are each independently 【Chemistry 13】 (In the formula, ＊ indicates a bond to the group of general formula III and / or IV) is selected from the group consisting of:

6. The compound of claim 5 , wherein X and Z are each O.

7. X and Z are O, R ４ is H, and R ５ and R6 is H.

8. R ２ and R ３ The compound according to claim 1 or 5, wherein are identical.

9. 10. The compound of claim 1 or 5, wherein the compound is selected from the group consisting of: 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】

10. 10. An optoelectronic component comprising a first electrode (2), a second electrode (3) and a layer system (7) arranged between the first electrode (1) and the second electrode (2), at least one layer of the layer system (7) comprising at least one compound according to any one of the preceding claims.

11. The optoelectronic component according to claim 10, wherein the optoelectronic component is an organic solar cell, an OFET, an OLED or an organic photodetector.

12. 11. The optoelectronic component according to claim 10, wherein the layer system (7) comprises at least one optically active layer (4), the at least one optically active layer (4) comprising at least one compound according to any one of claims 1 to 9.

13. 13. The optoelectronic component according to claim 12, wherein the optically active layer (4) is formed as a mixed layer consisting of at least one compound according to any one of claims 1 to 9 and at least one further compound or as a mixed layer consisting of at least one compound according to any one of claims 1 to 9 and at least two further compounds.

Images