Organic semiconductor compounds having indole groups, organic optoelectronic components containing the compound of the type, and use of the compound of the type.

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 a compound of general formula I, an optoelectronic component containing such compound, and the use of such compound in an optoelectronic component. [Background technology]

[0002] Circuits fabricated 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, particularly organic photoactive components, including solar cells and photodetectors having a photoactive layer in which an incident electromagnetic beam causes the generation of charge carriers, particularly bound electron-hole pairs (excitons).

[0003] Photoactive optoelectronic components utilize the photoelectric effect to enable the conversion of electromagnetic waves into electric currents. Such electromagnetic wave conversion requires absorbent materials that exhibit good absorption properties. Further optoelectronic components are light-emitting electroluminescent components that emit light when an electric current flows through them. A photoelectronic component includes at least two electrodes, one applied to a substrate and the other acting as a counter electrode. Between the electrodes is at least one photoactive layer, preferably an organic photoactive layer. Further layers, such as charge carrier transport layers, can be additionally placed between the electrodes.

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

[0005] Patent Document 1 of the international patent application discloses 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, which can function as a functional component in organic electronic components, resulting in improved absorption in organic solar cells or increased charge carrier mobility.

[0007] While absorber materials disclosed in the prior art are suitable for the photoactive layer of organic solar cells, improvements in the efficiency of absorber materials are necessary, particularly to enable organic solar cells (OPVs) to compete with conventional silicon-based solar cells. A specific drawback of the prior art is that the efficiency of absorber materials with high absorption coefficients is not adequate, particularly in the blue / green region of visible light, when constructing solar cells having an open-circuit voltage Uoc in the region of 0.9V or higher, preferably 0.94V or higher, or preferably 0.95V or higher, and especially in the region of 1V. In particular, at wavelengths in the 500-600nm range, the absorption of known organic compounds for small molecules used in organic optoelectronic components, especially absorber molecules, is not adequate. This effect is that photons in this wavelength range cannot be utilized to a sufficient extent.

[0008] The search for semiconductor organic materials that improve the properties of organic optoelectronic components, particularly their electromagnetic wave absorption, when used in such components, continues. [Prior art documents] [Patent Documents]

[0009] [Patent Document 1] International Publication No. 2017 / 114937A1 Pamphlet [Patent Document 2] International Publication No. 2017 / 114938A1 Pamphlet [Overview of the project] [Problems that the invention aims to solve]

[0010] Accordingly, an object of the present invention is to provide an organic compound having improved absorption properties suitable for use in organic optoelectronic components, an optoelectronic component comprising at least one such compound, and the use of such compound in an optoelectronic component, without causing the aforementioned drawbacks, and specifically, improving the absorption of electromagnetic waves and / or increasing the efficiency of the organic solar cell. [Means for solving the problem]

[0011] This objective is achieved by the subject matter of the independent claim. The advantageous configuration is evident from the dependent claim.

[0012] The purpose of this work is, in particular, General Formula I [ka] (In the formula, R1 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl. R4 is selected from the group consisting of H, halogens, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, and alkenyl, and electron-withdrawing alkyl groups having at least one CC double bond (where H may be substituted with CN or F). At least one A1, A2, A3, or A4 is independently based on the base Ia in each case. [ka] (Here, for each case, * This represents the attachment of a compound of general formula I, Z is selected from the group consisting of O, S, Se, and N-R8 (where R8 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl). Y3 is N or C-R9, where R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, and aryl (where H may be optionally substituted in each case), Y4 is N or C-R10, where R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, and aryl (where H may be optionally substituted in each case), provided that R9 and R10 may be linked to each other in the form of a ring structure homocyclically or heterocyclically, and 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 (where H may be substituted by CN or F) and each of the other A1, A2, A3, or A4 is independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and amino, and A5 is H, alkyl, alkoxy, and group Ib [Chemical formula] (where * represents attachment to the compound of general formula I, X is selected from the group consisting of O, S, Se, and N-R7, where R7 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl) Y1 is N or C-R5, where R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, and aryl (where H may be optionally substituted in each case), Y2 is N or C-R6, where R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or acyclic alkyl, alkenyl, and aryl (where H may be optionally substituted in each case), provided that R5 and R6 may be homocyclically or heterocyclically bonded to each other in the form of a ring structure, 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) selected from the group consisting of characterized in that is achieved by providing a compound of

[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 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 homocyclic or heterocyclically bonded to each other in the form of a ring structure.

[0017] In preferred embodiments of the present invention, the central indole unit, particularly the pyrrole ring of the indole unit, does not have any further condensed aromatic systems.

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

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

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

[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 a heteroatom in general formula I, is understood to specifically mean an atom selected from the group consisting of O, S, Se, Si, B, N, and P, preferably selected from the group consisting of O, S, Se, and N.

[0024] In alternatively preferred embodiments, the central indole unit, particularly the pyrrole ring of the indole unit, has at least one fused homocyclic or heterocyclic 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 an aromatic system.

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

[0027] In preferred embodiments of the present invention, the aryl group and heteroaryl group 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, and C-SC2H5.

[0029] In preferred embodiments of the present invention, the cyclic or open-chain alkyl group of the compound of the present invention is linear or branched, and the alkyl group is preferably a C1-C5 alkyl group.

[0030] In preferred embodiments of the present invention, at least one of positions Y1, Y2, 3, and Y4 is N, preferably at least one position Y1 or Y2 is N and / or at least one position Y3 or Y4 is N. This achieves, in particular, a decrease in the highest occupied molecular orbital (HOMO) of electrons, accompanied by a shift in the absorption spectrum of the compound of the present invention to shorter wavelengths.

[0031] In a particularly preferred embodiment of the present invention, Y1, Y2, Y3, and Y4 are each CH. In this case, the two five-membered rings are each furan rings 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 exhibit remarkably good absorption properties over a relatively broad spectral range of visible light from 500 to 700 nm, and specifically, remarkably high absorption was observed in the spectral range of approximately 500 to 700 nm. Advantageously, an absorber material with improved absorption within the wavelength range of the blue / green region of visible light is provided. Remarkably, the central structural unit, i.e., the central indole unit, of the compounds of the present invention is extremely suitable for obtaining compounds with desired absorbency. Advantageously, the compounds of the present invention possess sufficient thermal, chemical, and electrochemical stability to meet the demands typically required in the manufacture and operation of photoactive organic electronic components, and specifically, this compound can be readily evaporated under reduced pressure, particularly without residue. Advantageously, the compounds of the present invention possess charge carrier transport properties, making them suitable for use in organic optoelectronic components, particularly organic solar cells. Advantageously, this compound has very good transport properties and, in particular, a particularly suitable energy level. Remarkably, the compounds of the present invention have been found to have particularly good absorption of electromagnetic light, particularly light in the visible spectral region, due to the central structural element of the indole unit. Therefore, in particular, the efficiency of the organic optoelectronic component is increased and / or the charge carrier mobility of the photoactive layer is increased. Advantageously, the compounds of the present invention have a high absorption coefficient. Advantageously, the open-circuit voltage Uoc is greater than 0.9V, preferably greater than 0.94V, and particularly preferably greater than 0.95V.

[0033] In one advanced form of the present invention, the compound is general formula II [ka] (In the formula, 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, independently, either O or S. It is a compound of [the compound].

[0034] In one advanced form of the present invention, the compound is of general formula VII [ka] (In the formula, 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, where A1 or A4 is preferably a hydrogen atom. It is a compound of [the compound].

[0035] In a preferred embodiment of the present invention, at least two A1, A2, A3, or A4 are each independently based on the base Ia [ka] 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 evolved form of the present invention, at least one A1, A2, A3, or A4 is independently, [ka] (wherein R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, alkenyl, and electron-withdrawing alkyl groups having at least one CC double bond (wherein H may be substituted with CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one CC double bond (wherein H may be substituted with CN or F), R9 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (where H may be substituted in each case), R10 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case), provided that R9 and R10 are homocyclic or heterocyclically linked to each other in the form of a ring structure. That is the case.

[0037] In a preferred embodiment of the present invention, at least two of the bases A1, A2, A3, or A4 are, each independently, [ka] (wherein R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, alkenyl, and electron-withdrawing alkyl groups having at least one CC double bond (wherein H may be substituted with CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one CC double bond (wherein H may be substituted with CN or F), R9 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (where H may be substituted in each case), R10 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case), provided that R9 and R10 are homocyclic or heterocyclically linked to each other in the form of a ring structure. That is the case.

[0038] In one advanced form of the present invention, the compound is of general formula III and / or IV [ka] (In the formula, R1 is H or alkyl, X and Z are independently either O or S. A1, A3, and A4, or A1, A2, and A4, are each independently selected from the group consisting of H, halogens, 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 electron-withdrawing alkyl groups having at least one CC double bond (where H may be substituted with CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one CC double bond (where H may be substituted with CN or F). However, preferably, X and Z are O, R4 is H, and R5 and R6 are H. It is a compound of [the compound].

[0039] In a preferred embodiment of the present invention, the compound is of general formula X [ka] (In the formula, R1 is H or alkyl, X and Z are independently either O or S. A2, A3, and A4 are each independently selected from the group consisting of H, halogens, 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 electron-withdrawing alkyl groups having at least one CC double bond (where H may be substituted with CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one CC double bond (where H may be substituted with CN or F). However, preferably, X and Z are O, R4 is H, and R5 and R6 are H. It is a compound of [the compound].

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

[0041] In preferred embodiments of the present invention, the compound is of general formula XI [ka] (In the formula, R1 is H or alkyl, X and Z are independently either O or S. A1, A2, and A3 are each independently selected from the group consisting of H, halogens, 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 electron-withdrawing alkyl groups having at least one CC double bond (where H may be substituted with CN or F), and R3 is preferably an electron-withdrawing alkyl group having at least one CC double bond (where H may be substituted with CN or F). However, preferably, X and Z are O, R4 is H, and R5 and R6 are H. It is a compound of [the compound].

[0042] In a preferred embodiment of the present invention, A1, A2, and A3 in the compound of general formula XI 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 at positions Y3 and / or Y4 of formula IIa. [ka]

[0044] As a result, the resulting optical properties, particularly light absorption, are more favorable than those of equivalent compounds containing atoms other than oxygen.

[0045] In one advanced form of the present invention, In equation III, A1, A3, and A4 are H (equation V), and in equation IV, A1, A2, and A4 are H (equation VI). [ka] In the formula, X and Z are each independently O or S, and R5 and R6 are preferably H. This exceptionally realizes the advantageous effects of the present invention.

[0046] In one advanced form of the present invention, the compound is of general formula VIII and / or IX [ka] (In the formula, R1 is H or alkyl, X and Z are independently either O or S. R9 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case). R10 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case), provided that R9 and R10 are homocyclic or heterocyclically linked to each other in the form of a ring structure. R5 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case). R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (where H may be substituted in each case), provided that R5 and R6 may be homocyclic or heterocyclically linked to each other in the form of a ring structure. However, preferably, R5 and R6 are H, and R9 and R10 are H. It is a compound of [the compound].

[0047] In a preferred embodiment of the present invention, the compound is of general formula XII [ka] (In the formula, R1 is H or alkyl, X and Z are independently either O or S. R9 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case). R10 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case), provided that R9 and R10 are homocyclic or heterocyclically linked to each other in the form of a ring structure. R5 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case). R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (where H may be substituted in each case), provided that R5 and R6 may be homocyclic or heterocyclically linked to each other 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 electron-withdrawing alkyl having at least one CC double bond (where H may be substituted with CN or F), preferably R3 is an electron-withdrawing alkyl having at least one CC double bond, and R2 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, alkenyl, and electron-withdrawing alkyl having at least one CC double bond (where H may be substituted with CN or F), preferably R2 is an electron-withdrawing alkyl having at least one CC double bond. It is a compound of [the compound].

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

[0049] In a preferred embodiment of the present invention, group A5 is identical to 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 CC double bond (where H may be substituted with CN or F), and / or R3 in group Ia has an electron-withdrawing alkyl group having at least one CC double bond (where H may be substituted with CN or F).

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

[0053] In one advanced form of the present invention, R2 and R3 are each independent of each other. [ka] (In the formula, n is 1, 2, 3, or 4, * This represents the attachment of general formula Ia and / or Ib to the base, R11, R12, and R13 are each independently selected from the group consisting of H, halogens, CN, COO-alkyl, alkenyl, alkynyl, alkoxy, cyclic or open-chain alkyl, cyclic or open-chain alkenyl (wherein H may be substituted with halogen or CN in each case), provided that both R11 and R12 are not H. This exceptionally enables the advantageous effects of the present invention.

[0054] In a preferred embodiment of the present invention, R2 and / or R3 are independently of each case. [ka] (wherein m is 0, 1, or 2, and l is 0, 1, or 2, R11, R12, R13, R14, R15, and R16 are each independently selected from the group consisting of H, halogens, CN, COO-alkyl, alkenyl, alkynyl, alkoxy, cyclic or open-chain alkyl, cyclic or open-chain alkenyl (wherein H may be substituted with halogen or CN in each case), provided that both R11 and R12 are not H. Therefore, the presence of numerous CN groups makes it possible to achieve specific and favorable acceptor activity for the R2 and / or R3 groups.

[0055] In a further development of the present invention, R2 and R3 are each independently, [ka] (In the formula, * (wherein R2 and R3 are preferably the same) It is selected from the group consisting of the following.

[0056] In one advanced form of the present invention, the compound is [ka] [ka] [ka] It is selected from the group consisting of the following.

[0057] In one advanced form of the present invention, the compound is F7 and / or F16 [ka] That is the case.

[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 preferred embodiments of the present invention, the compound of general formula I additionally has a five-membered ring or a six-membered ring formed by R5 and R6 and / or R9 and R10, the five-membered ring or the six-membered ring may be substituted at further positions.

[0060] Organic single or tandem cells are known from the prior art. German Patent Application Publication No. 102004014046A1 discloses a photoactive component, particularly a solar cell, comprising one or more organic layers of pi, ni, and / or pin diodes stacked together. International Patent Application Publication No. 201116108A1 discloses a photoactive component having electrodes and counter electrodes, comprising at least one organic layer system disposed between electrodes, having at least two photoactive layer systems and at least two different transport layer systems of the same charge carrier type between the photoactive layer systems, characterized in that one transport layer system is matched to the energy of one of the two photoactive layer systems and the other transport layer system is transparent.

[0061] The object of the present invention is also achieved by providing an optoelectronic component comprising at least one compound of the present invention, in particular, relating to one of the exemplary embodiments described above. In the optoelectronic component, this brings about the advantages already revealed in relation to the compound of the present invention, in particular. The optoelectronic component comprises a first electrode, a second electrode, and a layer system, the layer system being positioned between the first electrode and the second electrode, characterized in that at least one layer of the layer system comprises at least one compound of the present invention.

[0062] The efficiency of organic optoelectronic components depends on factors including the absorption properties of the compound, i.e., the absorber material. Advantageous properties here are particularly high absorption and absorption over a broad spectrum of usable electromagnetic waves, as these allow photons of various wavelengths to be utilized for power generation.

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

[0064] An organic photovoltaic element (OPV) is understood to specifically mean a photovoltaic element having at least one organic photoactive layer comprising at least one compound of the present invention. Photoactive organic optoelectronic components enable the conversion of electromagnetic rays, such as those within the visible light wavelength range, into electric current by utilizing the photoelectric effect. The conversion requires an organic semiconductor material that exhibits sufficiently good absorption.

[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), OFT, OLED, or organic photodetector.

[0066] Here, the organic electronic component includes electrodes and counter electrodes, in particular, along 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). Specifically, the organic photoactive layer is a photoactive layer in which excitons (electron-hole pairs) are formed by emission of visible light, UV rays, and / or IR rays. The organic material is applied in the form of a thin film or small amount on a foil by printing, glue bonding, coating, vapor deposition, or other methods. 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 advanced embodiment of the present invention, the layer system has at least one photoactive layer, preferably an absorber layer, and the 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 advanced form 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, preferably an absorber layer.

[0069] In a preferred embodiment of the present invention, the organic solar cell has a photoactive layer containing at least one organic donor material in contact with at least one organic acceptor material, wherein the donor material and 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 further layer, preferably at least one charge transport layer, in particular an electron transport layer and / or a hole transport layer.

[0071] In preferred embodiments of the present invention, at least one charge transport layer, in particular at least one electron transport layer and / or at least one hole transport layer, comprises at least one compound of the present invention.

[0072] In preferred embodiments 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 is specifically understood to mean two functional cells that are spatially stacked and sequentially connected to each other, preferably between a first electrode and a second electrode, although one or more intermediate layers may be provided between the cells. Therefore, a multiple cell or multi-junction cell is understood to mean two or more functional cells that are spatially stacked and sequentially connected to each other, although intermediate layers may be provided 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, and specifically, one of the electrodes of the optoelectronic component may be directly applied to the substrate.

[0075] In one advanced 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, preferably the compounds being absorbent materials.

[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 cell containing at least one i layer.

[0077] The i-layer is specifically understood to mean an intrinsic undoped layer. One or more i-layers may consist of one material (planar heterojunction, PHJ) or a mixture of two or more materials called a bulk heterojunction (BHJ) with an interpenetrating network.

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

[0079] The object of the present invention is also achieved by providing the use of the compounds of the present invention in optoelectronic components, preferably organic optoelectronic components, and particularly those relating to one of the above embodiments. The use of the compounds of the present invention in optoelectronic components brings, in particular, the advantages already revealed in connection with the compounds of the present invention and optoelectronic components comprising at least one of the compounds 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] The following sections describe some specific examples of the compounds of the present invention and their optical properties. Table 1 outlines the melting points and absorption maxima (in nm and eV units in solvent (SO)) of these compounds of the present invention. The relevant absorption spectra of the compounds listed in Table 1 are shown in Figures 3-15. The spectral data pertain to a vacuum vapor deposition layer on quartz glass with a thickness of 30 nm.

[0082] [Table 1]

[0083] TIFF0007840446000024.tif234170

[0084] TIFF0007840446000025.tif78170

[0085] The optical properties were determined experimentally. The absorption maximum λmax was determined using a photometer in dilute solutions in cuvettes in dichloromethane. The measured absorption maximums for all listed compounds were between 530 and 610 nm.

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

[0087] The compounds of the present invention have particularly good radiation absorption rates, and therefore, it can be inferred from the absorption spectra in Table 1 that they have relatively high optical density integral values ​​in the visible spectral region. Here, "integral value" refers to the area under the curve of the absorption spectrum, which is an important characteristic of the suitability of the material as a photoactive material.

[0088] Table 2 directly compares various parameters of the compounds of the present invention. The photovoltaic parameters of the open-circuit voltage Uoc, short-circuit current Jsc, and curve factor FF pertain to the same solar cell structure in each case.

[0089] In testing the compound of the present invention, specifically its use as an absorber material in organic optoelectronic components, AM1.5 illumination (AM = air mass, AM = 1.5, in this spectrum the total radiation power is 1000 W / m²) is used. 2 Current-voltage curves were measured in a BHJ cell having glass with the following 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), with the photoactive layer being a bulk heterojunction (BHJ). A transparent cover contact made of ITO (indium tin oxide) was applied to the glass substrate. In this structure, ITO acts as an electrode, and the adjacent fullerene C60 acts as an electron transport layer (ETL). Adjacent to this are a photoactive C60 layer as an electron acceptor material and the respective compounds of the present invention as hole acceptor materials (donor materials), followed by a hole transport layer (HTL) consisting of BPAPF (9,9-bis[4-(N,N-bis(biphenyl-4-yl)amino)phenyl]-9H-fluorene) and BPAPF doped with NDP9 (Novaled AG), and finally an electrode made of aluminum (see Figure 2).

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

[0091] [Table 2]

[0092] The particularly advantageous properties of the compounds of the present invention are also demonstrated by the photovoltaic parameters of the open-circuit voltage Uoc, short-circuit current Jsc, and curve factor FF in the same solar cell structure. The increased curve factor FF suggests that the compounds of the present invention possess not only improved absorptive properties but also excellent charge carrier transport properties. Depending on the charge transport and absorptive properties, high photocurrents can be achieved along with good curve factors. Therefore, it is possible to manufacture tandem / triple / quadruple or multi-junction solar cells that are very well combined. Of the compounds shown in Table 2, compounds F3, F4, F6, F8, F9, and F13 have the best optical properties, and moreover, in particular, the best cell efficiency (eff) i.e., the best efficiency, is achieved in organic solar cells manufactured from these compounds, and of these compounds, F6 and F9 have the best efficiency in solar cells. Each of these compounds has a furan ring and / or thiophene ring, particularly one furan ring each, on a 5-membered ring and a 6-membered ring on a central indole unit. In addition, a hydrogen atom on the nitrogen atom of the pyrrole ring of the central indole unit, or a methyl, ethyl, propyl, or butyl group, particularly an isopropyl, isobutyl, or s-butyl group, is advantageous. Preferably, further five-membered rings (Ia, IIa) are attached to the 2' and 6' positions of the central indole unit. The two outer five-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 below with reference to the drawings. The drawings show the following: [Brief explanation of the drawing]

[0094] [Figure 1] An example of a synthesis scheme for the synthesis of the compound of the present invention. [Figure 2] A schematic cross-sectional view of an example of an optoelectronic component. [Figure 3] Graphs of the absorption spectrum of compound F1, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F1, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 4] Graphs of the absorption spectrum of compound F2, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F2, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 5] Graphs of the absorption spectrum of compound F3, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F3, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 6] Graphs of the absorption spectrum of compound F4, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F4, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 7] Graphs of the absorption spectrum of compound F5, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F5, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 8] Graphs of the absorption spectrum of compound F6, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F6, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 9] Graphs of the absorption spectrum of compound F7, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F7, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 10] Graphs of the absorption spectrum of compound F8, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F8, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 11] Graphs of the absorption spectrum of compound F9, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F9, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 12]Graphs of the absorption spectrum of compound F10, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F10, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 13] Graphs of the absorption spectrum of compound F11, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F11, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 14] Graphs of the absorption spectrum of compound F12, as well as graphs of the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F12, measured in an organic optoelectronic component in the form of an organic solar cell. [Figure 15] Graphs showing the current-voltage curve, spectral extraquantum yield, and curve factor of a BHJ cell containing compound F13, measured in an organic optoelectronic component in the form of an organic solar cell. [Modes for carrying out the invention]

[0095] Examples Figure 1 shows an example of a synthesis scheme for the synthesis of the compound 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, please refer in particular to the International Publication Brochures 2017114937A1 and 2017114938A1 of the international applications.

[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 yield. Compounds F1, F7, F13, and F16 are prepared by the synthesis disclosed in International Publication Brochures 2017114937A1 and 2017114938A1 of the international application. The attachment positions of substituents (Ia, IIa) to the central indole unit are summarized in Table 3.

[0098] [Table 3]

[0099] General formula I [ka] The compounds of the present invention are characterized in that R1 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl, and R4 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, and at least one A1, A2, A3, or A4 is independently, in each case, group Ia [ka] (Here, for each case, * The symbol represents attachment to a compound of general formula I, and Z is selected from the group consisting of O, S, Se, and N-R8 (where R8 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl). Y3 is N or C-R9 (where R9 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (where H may be substituted in each case)), Y4 is N or C-R10 (where R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (where H may be substituted in each case)), provided that R9 and R10 may be homocyclic or heterocyclically bonded to each other in the form of a ring structure, and R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, alkenyl, and electron-withdrawing alkyl having at least one CC double bond (where H may be substituted with CN or F)), 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, and A5 is H, alkyl, alkoxy, and group Ib [ka] (Here, *represents attachment to a compound of general formula I, where X is selected from the group consisting of O, S, Se, and N-R7 (where R7 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl), Y1 is N or C-R5 (where R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (where H may be substituted in each case)), and Y2 is N or C-R6 (where R6 is H, halogen, alkoxy, branched or linear R5 and R6 are selected from the group consisting of cyclic or open-chain alkyls, alkenyls, and aryls (wherein H may be substituted in each case), provided that R5 and R6 are homocyclic or heterocyclically linked to each other in the form of a ring structure, and R2 is selected from the group consisting of H, alkoxys, alkyls, fluorinated alkyls, partially fluorinated alkyls, branched or linear cyclic or open-chain alkyls, aminos, aryls, alkenyls, and electron-withdrawing alkyls having at least one CC double bond (wherein H may be substituted with CN or F). Selected from the group consisting of, It is characterized by the following:

[0100] In one embodiment of the present invention, the compound is of general formula II [ka] (In the formula, R1 is preferably selected from the group consisting of H and alkyl, 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) It is a compound of [the compound].

[0101] In a further embodiment of the present invention, the compound is of general formula VII [ka] (In the formula, 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.) It is a compound of [the compound].

[0102] In a further configuration of the present invention, at least one A1, A2, A3, or A4 is independently, [ka] (In the formula, R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, alkenyl, and electron-withdrawing alkyl having at least one CC double bond (wherein H may be substituted with CN or F); R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, aryl (wherein H may be substituted in each case); and R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (wherein H may be substituted in each case), provided that R9 and R10 are linked to each other in a homocyclic or heterocyclic manner in the form of a ring structure.) That is the case.

[0103] In a further embodiment of the present invention, the compound is of general formula III and / or IV [ka] (wherein R1 is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl, X and Z are each independently O or S, and R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and electron-withdrawing alkyl groups having at least one CC double bond (where H may be substituted with CN or F), However, preferably, X and Z are O, R4 is H, and R5 and R6 are H. It is a compound of [the compound].

[0104] In a further embodiment 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). [ka] (In the formula, X and Z are independently either O or S, R5 and R6 are preferably H).

[0105] In a further embodiment of the present invention, the compound is of general formula VIII and / or IX. [ka] (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 open-chain alkyl, alkenyl, and aryl (wherein H may be substituted in each case), and R10 is selected from the group consisting of H, halogen, alkoxy, branched or linear cyclic or open-chain alkyl, alkenyl, and aryl (wherein H may be substituted in each case), provided that R9 and R10 are homozygous with each other in the form of a ring structure) R5 may be linked cyclically or heterocyclically, and R5 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (where H may be substituted in each case), and R6 is selected from the group consisting of H, halogens, alkoxys, branched or linear cyclic or open-chain alkyls, alkenyls, and aryls (where H may be substituted in each case), provided that R5 and R6 may be linked 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. It is a compound of [the compound].

[0106] In a further configuration of the present invention, R2 and R3 are each independently, [ka] (In the formula, n is 1, 2, 3, or 4, * In each case, R11 represents the attachment of general formula Ia and / or Ib to a group, and R11, R12, and R13 are each independently selected from the group consisting of H, halogen, CN, COO-alkyl, alkenyl, alkynyl, alkoxy, cyclic or open-chain alkyl, cyclic or open-chain alkenyl (wherein each case H may be substituted with halogen or CN), provided that both R11 and R12 are not H, provided that R11 and R12 are preferably CN. That is the case.

[0107] In a further configuration of the present invention, R2 and R3 are each independently

Chemical formula

[0108] In a further configuration of the present invention, the compound is

Chemical formula

Chemical formula

Chemical formula

[0109] In a further configuration of the present invention, the compound is F7 and / or F 16[[ID=,39]]

Chemical formula

[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] Organic solar cell structures known from 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 International Publication No. 2011 / 161108A1). 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 embodiment, the optoelectronic component is a solar cell. The solar cell has, for example, a glass substrate 1, on which electrodes 2 containing, for example, ITO are present. On top of that, an electron transport layer 3 (ETL) and a photoactive layer 4 containing at least one p-conducting donor material and an n-conducting acceptor material, such as C60 fullerene, are disposed in either a planar heterojunction or a bulk heterojunction. On top of that, a p-doped hole transport layer 5 (HTL) and an aluminum electrode 6 are disposed.

[0115] In a further configuration of the present invention, the layer system 7 has at least one photoactive layer 4, preferably an absorber layer, and the at least one photoactive 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 optically active layers, preferably at least three optically active layers, or preferably at least four optically active layers.

[0117] In a further configuration 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, wherein the compounds are preferably absorbent materials.

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

[0119] Figures 3 to 15 below illustrate specific examples of the compounds of the present invention and their optical properties.

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

[0121] Absorption spectra (optical density for each wavelength in nanometer units) were measured in 30 nm thick vacuum-deposited layers of each compound F1-F13 on quartz glass.

[0122] The current-voltage curve contains indicators that characterize organic solar cells. The most important indicators here are the curve 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 15 nm thick C60 layer. Compound F1 was applied to this layer together with C60 to a thickness of 30 nm. Following this layer is a 10 nm thick BPAPF layer, and on top of that is a further 30 nm thick layer containing BPAPF and NDP9. The proportion of BPAPF in this layer is 10 wt percent relative to the entire layer. This layer is adjacent to a further 1 nm thick layer containing NDP9, followed by a 100 nm thick aluminum layer. Using a photoactive layer characterized by a bulk heterojunction (BHJ), the current-voltage curve of a BHJ cell with 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 optoelectronic components containing compound F1, the curve factor FF is 62.7%, the open-circuit voltage Uoc is 0.83V, and the short-circuit current Jsc is 10.8mA / cm2. The battery efficiency of this type of optoelectronic component containing compound F1, particularly in solar cells, is 5.62%.

[0124] Compound F1 also exhibits particularly good evaporability at temperatures ranging from 240°C to 255°C.

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

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

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

[0128] The current-voltage curve of a BHJ cell with the structure: ITO / C60(15nm) / F3:C60(30nm, 3:2, 50℃) / BPAPF(10nm) / BPAPF:NDP9(30nm, 10 wt%NDP9) / NDP9(1nm) / Al(100nm) was determined using a bulk heterojunction (BHJ) as the photoactive layer. For optoelectronic components containing compound F3, the curve factor FF was 73.8%, the open-circuit voltage Uoc was 0.98V, and the short-circuit current Jsc was 11.5mA / cm2. The battery efficiency of this type of optoelectronic component containing compound F3, particularly in solar cells, was 8.32%. F3 exhibits particularly good transportability along with a high curve factor FF.

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

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

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

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

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

[0134] The current-voltage curve of a BHJ cell with 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 using a bulk heterojunction (BHJ) as the photoactive layer. In the optoelectronic component containing compound F6, the curve factor FF was 72.5%, the open-circuit voltage Uoc was 0.96 V, and the short-circuit current Jsc was 13.8 mA / cm². The battery efficiency of this type of optoelectronic component containing compound F6, particularly in solar cells, was 9.60%.

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

[0136] The current-voltage curves of BHJ cells with the structure: ITO / C60(15nm) / F7:C60(30nm, 3:2, 50℃) / BPAPF(10nm) / BPAPF:NDP9(30nm, 10 wt%NDP9) / NDP9(1nm) / Al(100nm) were determined using a bulk heterojunction (BHJ) as the photoactive layer. For optoelectronic components containing compound F7, the curve factor FF was 63.6%, the open-circuit voltage Uoc was 1.0V, and the short-circuit current Jsc was 9.8mA / cm2. The battery efficiency of this type of optoelectronic component, particularly solar cells, containing compound F1 was 6.23%.

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

[0138] The current-voltage curve of a BHJ cell with the structure: ITO / C60(15nm) / F8:C60(30nm, 3:2, 50℃) / BPAPF(10nm) / BPAPF:NDP9(30nm, 10 wt%NDP9) / NDP9(1nm) / Al(100nm) was determined using a bulk heterojunction (BHJ) as the photoactive layer. For optoelectronic components containing compound F8, the curve factor FF was 67.9%, the open-circuit voltage Uoc was 0.98V, and the short-circuit current Jsc was 12.8mA / cm2. The battery efficiency of this type of optoelectronic component containing compound F8, particularly in solar cells, was 8.52%. Compound F8 exhibits particularly stable behavior under vacuum deposition.

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

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

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

[0142] The current-voltage curves of BHJ cells with the structure: ITO / C60(15nm) / F10:C60(30nm, 3:2, 50℃) / BPAPF(10nm) / BPAPF:NDP9(30nm, 10 wt%NDP9) / NDP9(1nm) / Al(100nm) were determined using a bulk heterojunction (BHJ) as the photoactive layer. For optoelectronic components containing compound F10, the curve factor FF was 56.5%, the open-circuit voltage Uoc was 1.01V, and the short-circuit current Jsc was 11.8mA / cm2. The battery efficiency of this type of optoelectronic component, particularly solar cells, containing compound F10 was 6.73%.

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

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

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

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

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

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

[0149] The compounds of the present invention are highly suitable for use in organic solar cells and other organic optoelectronic components, and in particular, the ability to enable open-circuit voltages Uoc greater than 0.9V is demonstrated by experimental data of compounds F1 to F13, including the absorption properties of the compounds and current-voltage curves measured in organic solar cells.

Claims

1. General formula III and / or IV 【Transformation 7】 (In the formula, R １ This is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and s-butyl; R ４ This is selected from the group consisting of H, halogens, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, amino, aryl, and alkenyl; X and Z are O, respectively; A １ A ３ and A ４ , or A １ A ２ and A ４ Each of these is independently selected from the group consisting of H, halogens, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl; R ９ is selected from the group consisting of H, 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, R １０ This is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R5 is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R ６ is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups, and R2 and R ３ However, each operates independently. 【Chemistry 13】 (In the formula, ＊ (This indicates bonding with a group of general formula III and / or IV.) (Selected from the group consisting of) A compound of [unclear].

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

3. In equation III, A １ A ３ and A ４ H is (shown as equation V), In formula IV, A １ A ２ and A ４ H is (shown as equation VI), The compound according to claim 1. 【Transformation 8】

4. R ５ and R ６ The compound according to claim 3, wherein is H.

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, halogens, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear cyclic or open-chain alkyl, amino, aryl, and alkenyl; X and Z are independently either O or S. A １ A ３ , and A ４ , or A １ A ２ , and A ４ Each of these is independently selected from the group consisting of H, halogens, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl. R ９ This is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R １０ This is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R5 is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R ６ This is selected from the group consisting of H, halogen groups, alkyl groups (where the alkyl group may be linear or branched), alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, or heteroaryl groups. R2 and R ３ However, each operates independently. 【Chemistry 13】 (In the formula, ＊ (This indicates bonding with a group of general formula III and / or IV.) It is selected from the group consisting of the following.

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

7. X and Z are O, R ４ H is R ５ and R ６ The compound according to claim 5, wherein is H.

8. R ２ and R ３ The compound according to claim 1 or 5, wherein the same property is found.

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

10. A photoelectronic component comprising a first electrode (2), a second electrode (3), and a layer system, wherein the layer system (7) is disposed between the first electrode (1) and the second electrode (2), and at least one layer of the layer system (7) comprises at least one compound according to any one of claims 1 to 9.

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. The optoelectronic component according to claim 10, wherein the layer system (7) has at least one photoactive layer (4), and the at least one photoactive layer (4) has at least one compound according to any one of claims 1 to 9.

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

Images