Optoelectronic component having photoactive layer designed as planar heterojunction

Abstract

The invention relates to an optoelectronic component comprising a bottom electrode (2), a top electrode (6) and a layer system (7) having at least one photoactive layer (4). The layer system is arranged between the bottom electrode and the top electrode, and at least one photoactive layer is designed as a planar heterojunction (PHJ), the at least one photoactive layer designed as a planar heterojunction having at least one compound of general formula I. The invention also relates to the use of such compounds of general formula I in optoelectronic components and to a compound of general formula II.

Description

Technical Field

[0001] The present invention relates to an optoelectronic component having at least one photoactive layer in the form of a planar heterojunction (PHJ), wherein the at least one photoactive layer comprises a compound of the general formula I, and to the use of such a compound of the general formula I in an optoelectronic component. Background Art

[0002] Optoelectronic components can be displays, data storage media or transistors, but also photovoltaic elements (especially solar cells) and photodetectors, which have a photoactive layer in which the incidence of electromagnetic radiation generates electron-hole pairs (excitons). Excitons reach such an interface by diffusion, at which the electrons and holes are separated from each other. The material that accepts the electrons is called an acceptor, and the material that accepts the holes is called a donor. Organic optoelectronic components make it possible to convert electromagnetic radiation into electric current using the photoelectric effect. This conversion of electromagnetic radiation requires absorber materials that show good absorption characteristics.

[0003] Organic optoelectronic components are known from the prior art.

[0004] WO 2004083958 A2 discloses a photoactive component, in particular a solar cell, which consists of organic layers of one or more pi, ni and / or pin diodes stacked on top of one another.

[0005] WO 2011161108A1 discloses a structure of an organic solar cell as a pin or nip diode. A pin solar cell consists of a substrate on which a generally transparent electrode is arranged, one or more p layers, one or more i layers, one or more n layers, and a counter electrode. In this context, n and p refer to n-doping and p-doping, respectively, which increase the density of free electrons / holes in a thermal equilibrium state. Such layers should be understood as being primarily transport layers. The term "i layer" refers to an undoped layer (intrinsic layer) having an absorber material or a mixture of two or more absorber materials (planar heterojunction). One or more i layers here can be composed of a mixture of two or more materials (bulk heterojunction), i.e., at least one donor and at least one acceptor. In particular, an absorber material (i.e., an absorber) refers to a compound that absorbs light within a specific wavelength range. In particular, an absorber layer correspondingly refers to a layer in an optoelectronic component that contains at least one absorber material.

[0006] The prior art discloses a number of polymeric and non-polymeric absorber materials for organic photovoltaic elements in the red and near infrared (NIR) region between about 600 and about 1400 nm. In the field of non-polymeric absorber materials, materials from the substance class of BODIPY have been found to be particularly suitable for the near infrared spectral region, which means that suitable energy levels and therefore high photovoltages can be achieved at the same time in the long-wave absorption region.

[0007] EP 3 014 674 A1 discloses an organic electronic component comprising at least one organic layer between two electrodes, wherein the organic layer comprises at least one compound from the group of BODIPY.

[0008] Bartelmess et al. (“meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties”, New Journal of Chemistry, 2013, 37(9), 2663-2668) disclosed the synthesis of meso-pyridyl-substituted BODIPY compounds and their optical and electrochemical properties.

[0009] Absorbers known from the prior art cannot be used with sufficient efficiency for commercial use in planar heterojunctions for electronic components. Known absorber materials show in particular low efficiency. The efficiency of organic photovoltaic elements depends on factors including the absorption characteristics of the organic material in the photoactive layer, i.e. the absorber material. Although known absorber materials are suitable for the photoactive layer in organic photovoltaic elements, i.e. organic solar cells, there is a need to improve the absorption characteristics of absorber materials.

[0010] However, a disadvantage is that planar heterojunctions (PHJs) do not have good suitability for use in electronic components, especially in photovoltaic elements, especially since the efficiency of photovoltaic elements can be greatly limited due to the limited exciton diffusion length in such layers. Therefore, PHJ cells have not been an option for industrial photovoltaic elements to date.

[0011] However, since the efficiency of photovoltaic elements is improved and the production is simplified, it is desirable to use PHJs in photovoltaic elements. There is a demand for absorber materials which have high absorption, in particular in the red and near-infrared spectral regions, and which therefore lead to high efficiencies in PHJs. In BHJs, each component must form microdomains connected to each other in closed percolation paths, since otherwise charge transport may not occur. A particularly relevant factor here is the size of the individual microdomains, where too large individual domains lead to losses in photocurrent. Optimal process parameters for their production are achievable, but with difficulty, so that the industrially achievable efficiency of BHJs is lower than is possible under idealized laboratory conditions. In contrast, PHJs are much less demanding on process parameters, since the morphology of the individual layers inherently has fewer degrees of freedom that need to be controlled compared to BHJs. Summary of the invention

[0012] It is therefore an object of the present invention to provide an optoelectronic component having at least one photoactive layer in the form of a planar heterojunction comprising a compound of the general formula I, and the use of the compound of the general formula I in a photoactive layer in the form of a planar heterojunction in an optoelectronic component, wherein the mentioned disadvantages do not occur and wherein the use of planar heterojunctions is possible, in particular without limiting the efficiency of the photovoltaic element in the process.

[0013] This object is achieved by the subject matter of the independent claims. Advantageous configurations are evident from the dependent claims.

[0014] This object is achieved in particular by providing an optoelectronic component, preferably a photovoltaic element, having a base electrode, a top electrode and a layer system having at least one photoactive layer, wherein the layer system is arranged between the base electrode and the top electrode, wherein the at least one photoactive layer is in the form of a planar heterojunction (PHJ), and wherein the at least one photoactive layer in the form of a planar heterojunction comprises at least one compound of the general formula I

[0015]

[0016] Wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5;

[0017] Wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5;

[0018] Wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5;

[0019] wherein Z1 and Z2 are independently selected from the group consisting of: F, Cl, CN, CF3, C2F5, OCH3 and OC2H5;

[0020] wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3;

[0021] wherein R3 and R5 are independently selected from the group consisting of H, halogen, CN, unsubstituted and aryl- or heteroaryl-substituted alkyl, unsubstituted and aryl- or heteroaryl-substituted alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O and N, and unsubstituted and alkyl-substituted homocyclic 6-membered rings, wherein the unsubstituted or substituted heterocyclic 5- or 6-membered ring, or the unsubstituted or substituted homocyclic 6-membered ring may be fused to another unsubstituted or substituted heterocyclic 5- or 6-membered ring;

[0022] wherein R4 and R6 are independently selected from the group consisting of: H, halogen, CN, alkyl, alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O or N, and unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted homocyclic 6-membered rings;

[0023] Or wherein R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted heterocyclic 5- or 6-membered ring, preferably with at least one heteroatom selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted homocyclic 6-membered ring.

[0024] In particular, substitution means the exchange of H with a substituent. In particular, a substituent means any atom or atom group other than hydrogen, preferably a halogen (preferably F, Cl or Br, particularly preferably F), an alkyl group (wherein the alkyl group may be linear or branched), an alkenyl group, an alkynyl group, an amino group, an alkoxy group, a thioalkoxy group, an aryl group, or a heteroaryl group.

[0025] In particular, heteroatoms, especially heteroatoms in the general formula I, are atoms selected from the group consisting of O, S, Se and N.

[0026] In a preferred embodiment of the present invention, Y1 is selected from the group consisting of N and CR21, wherein R21 is H, C1-C4-alkyl, or halogen, preferably F or Cl; Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; and Y3 is selected from the group consisting of N and CR23, wherein R23 is H, C1-C4-alkyl, or halogen, preferably F or Cl.

[0027] In a preferred embodiment of the present invention, R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl)2, with the proviso that at least R1 or R2 is Br, Cl or CF3.

[0028] In a preferred embodiment of the present invention, in the substituted alkenyl, O-alkyl or S-alkyl in R3 and R5, the hydrogen atoms are replaced by groups selected from the following: unsubstituted and substituted heterocyclic 5-membered or 6-membered rings, preferably having at least one heteroatom selected from S, O and N, and unsubstituted and substituted homocyclic 6-membered rings.

[0029] In a preferred embodiment of the present invention, in R3 and / or R5, the unsubstituted or substituted heterocyclic 5-membered ring or 6-membered ring, or the unsubstituted or substituted homocyclic 6-membered ring is further fused to at least one additional heterocyclic 5-membered ring or 6-membered ring, or to at least one homocyclic 6-membered ring, preferably to an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S and O.

[0030] In a preferred embodiment of the present invention, R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted heterocyclic 5- or 6-membered ring, preferably with at least one heteroatom selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted homocyclic 6-membered ring.

[0031] In a preferred embodiment of the present invention, the unsubstituted or substituted heterocyclic 5-membered or 6-membered ring, or the unsubstituted or substituted homocyclic 6-membered ring formed between R3 and R4 and / or between R5 and R6 has no further fusion.

[0032] In a preferred embodiment of the present invention, R4 and R6 are independently selected from the group consisting of: H, halogen, CN, and unsubstituted and substituted alkyl. In a particularly preferred embodiment, R4 and R6 are H.

[0033] In a preferred embodiment of the present invention, R4 and R6 are the same, and / or R3 and R5 are the same.

[0034] In a preferred embodiment of the present invention, Z1 is identical to Z2, R3 is identical to R5, and R4 is identical to R6.

[0035] In particular, an optoelectronic component means a photovoltaic element having at least one organic photoactive layer, wherein the organic photoactive layer comprises at least one compound of the present invention. Organic photovoltaic elements allow the conversion of electromagnetic radiation, in particular in the visible wavelength range, into electric current by means of the photoelectric effect. In this context, the term "photoactive" means the conversion of light energy into electrical energy. Compared to inorganic solar cells, in the case of organic photovoltaic elements, excitons, i.e. electrically neutral excited states (bound electron-hole pairs), are first formed, rather than free charge carriers being generated directly by light. Only in a second step, these excitons are separated into free charge carriers at the photoactive donor-acceptor junction, which then contribute to the flow of electric current.

[0036] The optoelectronic components of the present invention have advantages compared to the prior art. Advantageously, an improved absorber for a planar heterojunction in an optoelectronic component can be provided. The use of planar heterojunctions has hitherto been possible but with difficulty due to the limited diffusion length in the planar heterojunction which limits the efficiency of optoelectronic components based on planar heterojunctions. However, it is desirable to use planar heterojunctions in optoelectronic components because they are easier to produce compared to bulk heterojunctions. Advantageously, the compounds of the present invention enable an improved EQE to be achieved in optoelectronic components having a planar heterojunction. max (maximum external quantum yield). Advantageously, the compounds of the present invention enable the use of planar heterojunctions in commercial optoelectronic components, which are particularly easier to produce than bulk heterojunctions. Advantageously, absorber materials for the red and near-infrared spectral regions with high absorption intensity and particularly good vaporizability are also provided for planar heterojunctions, which absorber materials can be processed under reduced pressure without decomposition. Advantageously, the spatial configuration of the groups in the meso position of the BODIPY base skeleton leads in particular to a preferred spatial arrangement of the compounds in the photoactive layer. The effect of the improved PHJ cell appears to be caused by the increased exciton diffusion length. Advantageously, the compounds of the present invention show exceptionally good properties in planar heterojunctions (PHJs), in particular enabling higher layer thicknesses of solar cells and therefore higher efficiencies.

[0037] In a preferred embodiment of the present invention, Z1 and Z2 are each F or CF3.

[0038] In a particularly preferred embodiment of the present invention, in R1 and R2, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl)2 are substituted, preferably substituted by substituents selected from the group consisting of: F, Cl, CN, CF3 and COR8, wherein R8 is C1-C4-alkyl.

[0039] In one development of the invention, it is the case that Z1 and Z2 are F; and / or R1 and R2 are independently selected from the group consisting of: H, F, Br, Cl, CN, Me, Et, OMe, SMe, OEt, SEt, Pr and iPr, with the proviso that at least R1 or R2 is Br, Cl or CF3, wherein preferably, R1 and R2 are not H; or R1 and R2 are independently selected from the group consisting of: Cl, Br, CF3, CN, Me, Et, OMe, SMe, OEt and SEt, with the proviso that at least R1 or R2 is Cl, Br, CF3 or Me; or, preferably, R1 and R2 are selected from the group consisting of: Br, Cl, CF3, CHF2, CH2F and CH3.

[0040] In a particularly preferred embodiment of the present invention, R1 and R2 are independently selected from the group consisting of Cl, CN, Me, Et, OMe, SMe, OEt and SEt, with the proviso that at least R1 or R2 is Cl.

[0041] In one development of the invention, it is the case that Y1 is selected from the group consisting of N and CR21, wherein R21 is H or Cl, and / or Y2 is selected from the group consisting of N and CR22, wherein R22 is H, CH3, O-CH3, S-CH3, F, Cl, CF3 or SF5, preferably N or CH, and / or Y3 is selected from the group consisting of N and CR23, wherein R23 is H or Cl; wherein, preferably, one Y1, Y2, Y3 is N, or two Y1, Y2, Y3 are N.

[0042] In a preferred embodiment of the present invention, Y1 is N or CH, and / or Y2 is N, CH or C-halogen, preferably CF or C-Cl, and / or Y3 is N and CH, wherein, preferably, at least one Y1, Y2, Y3 is N, or at least two Y1, Y2, Y3 are N.

[0043] In a preferred embodiment of the present invention, Y1 is N, Y2 is CH, and Y3 is N, or Y1 is N, Y2 is C-halogen, preferably CF or C-Cl, and Y3 is N, or Y1 is CH, Y2 is N, and Y3 is CH, or Y1 is CH, Y2 is CH, and Y3 is CH, and / or Y1 is CH, Y2 is C-halogen, preferably CF or C-Cl, and Y3 is CH.

[0044] In one development of the invention, it is the case that R3 and R4 and / or R5 and R6 form an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring with at least one heteroatom selected from O, S and N, preferably selected from O and S, or an unsubstituted or substituted homocyclic 6-membered ring, or that R3 and R4 and / or R5 and R6 form an unsubstituted or substituted heterocyclic 5-membered ring, preferably a substituted heterocyclic 5-membered ring, or an unsubstituted or substituted homocyclic 6-membered ring, preferably an unsubstituted homocyclic 6-membered ring, with at least one heteroatom selected from O, S and N, preferably O and S.

[0045] In a preferred embodiment of the present invention, the substituted heterocyclic 5-membered or 6-membered ring formed between R3 and R4 and / or between R5 and R6, respectively, preferably with at least one heteroatom selected from S, O and N, is substituted and selected from the group consisting of halogen, CN, alkyl, O-alkyl, S-alkyl, preferably unsubstituted and substituted heterocyclic 5-membered or 6-membered rings with heteroatoms independently selected from S, O and N, and unsubstituted and substituted homocyclic 6-membered rings. In a preferred embodiment of the present invention, the homocyclic 6-membered ring is unsubstituted.

[0046] In a preferred embodiment of the present invention, the respectively substituted homocyclic 6-membered ring formed between R3 and R4 and / or R5 and R6 is substituted and selected from the group consisting of halogen, CN, alkyl, O-alkyl, S-alkyl, preferably unsubstituted and substituted heterocyclic 5-membered or 6-membered rings with heteroatoms independently selected from S, O and N, and unsubstituted and substituted homocyclic 6-membered rings. In a preferred embodiment of the present invention, the homocyclic 6-membered ring is unsubstituted.

[0047] In a preferred embodiment of the present invention, R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from S, O and N. In a preferred embodiment of the present invention, R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or substituted furanyl ring or a thienyl ring.

[0048] In a preferred embodiment of the present invention, an unsubstituted or substituted heterocyclic 5-membered ring or 6-membered ring, or an unsubstituted or substituted homocyclic 6-membered ring formed by R3 and R4 and / or R5 and R6 is fused to an unsubstituted or substituted thienyl ring or furanyl ring.

[0049] In a preferred embodiment of the invention, R3 and R4 and / or R5 and R6 in each case together form an unsubstituted heterocyclic 5- or 6-membered ring which preferably has at least one heteroatom selected from S, O and N.

[0050] In a preferred embodiment of the invention, R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or substituted homocyclic 6-membered ring, and R3 and R4 and / or R5 and R6 in each case together do not form a heterocyclic 5-membered or 6-membered ring.

[0051] In one development of the invention, it is the case that at least one compound is a compound of the general formula II

[0052]

[0053] wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, preferably C1-C4-alkyl, O-alkyl, S-alkyl, or halogen, preferably F or Cl;

[0054] wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, preferably C1-C4-alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3;

[0055] wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, preferably C1-C4-alkyl, O-alkyl, S-alkyl, or halogen, preferably F or Cl;

[0056] Where Z1 and Z2 are F or CF3;

[0057] wherein X1 and X2 are independently O, S or N-R8, wherein R8 is selected from the group consisting of H, alkyl and aryl, wherein, preferably, X1 and X2 are S or X1 and X2 are O;

[0058] wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3, preferably Br or Cl;

[0059] wherein R13 and R15 are independently selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl;

[0060] wherein R14 and R16 are independently selected from the group consisting of: unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5-membered or 6-membered rings, preferably having heteroatoms independently selected from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered rings, preferably selected from unsubstituted and substituted heterocyclic 5-membered rings and unsubstituted and substituted homocyclic 6-membered rings.

[0061] In a preferred embodiment of the present invention, R14 and R16 are substituted heterocyclic 5-membered rings, wherein at least one hydrogen atom, preferably one hydrogen atom in the heterocyclic 5-membered ring is substituted, preferably substituted by a substituent selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl. In a preferred embodiment of the present invention, R14 and / or R16 have no additional fusion.

[0062] In a preferred embodiment of the present invention, R14 and R16 are independently unsubstituted or substituted furanyl ring or thienyl ring.

[0063] In a preferred embodiment of the present invention, X1 and X2 are S or X1 and X2 are O; particularly preferably, X1 and X2 are O.

[0064] In a preferred embodiment of the present invention, in R14 and R16, at least one hydrogen atom of the homocyclic 6-membered ring and / or the heterocyclic 5-membered ring or 6-membered ring is substituted by F or CF3, preferably by F.

[0065] In a preferred embodiment of the present invention, R13 and R15 are H.

[0066] In a preferred embodiment of the present invention, R13 and R15 are the same, and / or R14 and R16 are the same.

[0067] In a preferred embodiment of the present invention, Z1 is the same as Z2, R13 is the same as R15, and R14 is the same as R16.

[0068] In a preferred embodiment of the present invention, X1 and X2 are O or S, R13 and R15 are H, and R14 and R16 are unsubstituted or substituted heterocyclic 5-membered or 6-membered rings, preferably with heteroatoms selected from S, O and N, or unsubstituted or substituted homocyclic 6-membered rings, preferably substituted heterocyclic 5-membered rings.

[0069] In a preferred embodiment of the present invention, R13 and R14 and / or R15 and R16 in each case form an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from S, O and N, or an unsubstituted or substituted homocyclic 6-membered ring.

[0070] In a preferred embodiment of the present invention, R13 and R14 and / or R15 and R16 in each case form an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N.

[0071] In a preferred embodiment of the present invention, the compounds of the present invention do not have a ring structure between R13 and R14 and / or between R15 and R16.

[0072] In a development of the invention, it is the case that R14 and R16 are independently selected from the group consisting of:

[0073]

[0074] wherein X3 is O, S, or N-R9, wherein R9 is selected from the group consisting of H, alkyl, and aryl;

[0075] Wherein R17 to R19 and R31 to R35 are independently selected from the group consisting of: H, halogen, preferably F and Cl, CN, alkyl, preferably C1-C4-alkyl, O-alkyl, preferably O-C1-C4-alkyl, and S-alkyl, preferably S-C1-C4-alkyl, wherein preferably at least one hydrogen atom in R31 to R35 is replaced by F.

[0076] In a preferred embodiment of the present invention, R17 and / or R18, preferably R17 and R18, are H.

[0077] In a preferred embodiment of the present invention, at least R31 and R35 are H.

[0078] In a preferred embodiment of the present invention, R31, R32, R34 and R35 are H.

[0079] In another preferred embodiment, R31 to R35 are H.

[0080] In one development of the invention, it is the case that Z1 and Z2 are F and R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CF3, CHF2, CH2F and CH3, with the proviso that at least R1 or R2 is Br, Cl or CF3, preferably Br or Cl.

[0081] In one development of the invention, it is the case that Y1 and Y3 are CH and Y2 is CR22, preferably wherein CR22 is selected from the group consisting of F, Br, Cl and CN, or that Y1 is CR21, Y2 is N and Y3 is CR23, preferably wherein CR21 and CR23 are H or methyl, or that Y1 is N, Y2 is CR22 and Y3 is N, preferably wherein CR22 is H or methyl.

[0082] In a preferred embodiment of the present invention, R1 and R2 are each F or Cl.

[0083] In one development of the invention, it is the case that at least one compound is a compound of the general formula III

[0084]

[0085] Where X1 and X2 are independently O or S, wherein R 40 is H, Cl or F, preferably H, and wherein Hal is F, Br or Cl. In a particularly preferred embodiment of the present invention, the meso substituent on the BODIPY base skeleton is (4)-3,5-dichloropyridine, ie wherein each Hal=Cl and R40=H.

[0086] In one development of the invention, it is the case that at least one compound is a compound of the general formula IV

[0087]

[0088] Where X1 and X2 are independently O or S, wherein R 41 is H, F, Cl, Br, CF3 or C1-C4-alkyl, preferably H, particularly preferably H, F or Cl, and wherein Hal is Br, Cl or F.

[0089] In one development of the invention, it is the case that at least one compound is a compound of the general formula V

[0090]

[0091] Where X1 and X2 are independently O or S, wherein R 42 is H, F, Cl, CF3 or C1-C4-alkyl, and wherein Hal is Br, Cl or F.

[0092] In a preferred embodiment of the present invention, the at least one compound is a compound having the general formula III, a compound having the general formula VI, and a compound having the general formula III.

[0093] In one development of the invention, it is the case that R 14 and R 16 is independently an unsubstituted or halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N, preferably O and S, wherein, preferably, R19, R17 and R19, or R18 and R19 are substituted, or unsubstituted or halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered ring, wherein, preferably, R32, R33, or R32 and R34 are substituted, or R31 to R35 are H.

[0094] In one development of the invention, the compound is selected from the group consisting of:

[0095]

[0096]

[0097]

[0098] In a preferred embodiment of the invention, the compound is in mirror-symmetric form with respect to the axis passing through B and forms a meso position.

[0099] The general synthesis for preparing compounds of the present invention having a BODIPY-based skeleton and a 4-pyridylmeso group is known from Bartellmess et al. (“meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties”, New Journal of Chemistry, 37(9), 2663-2668; 2013).

[0100] The compounds of the present invention are particularly related to "small molecules". In particular, small molecules are understood to mean non-polymeric organic molecules having a monodisperse molar mass of between 100 and 2000 g / mol which are in the solid phase at standard pressure (the air pressure of the ambient atmosphere) and room temperature. In particular, these small molecules are photoactive, "photoactive" meaning that the molecule undergoes a change in its charge state and / or its polarization state when exposed to light. The specific feature of photoactive molecules is the absorption of electromagnetic radiation in a defined wavelength range, wherein the absorbed electromagnetic radiation (i.e. photons) is converted into excitons.

[0101] In one development of the invention, it is the case that the optoelectronic component is an organic optoelectronic component, preferably an organic photovoltaic element, an OFET, an OLED or an organic photodetector, particularly preferably an organic photovoltaic element.

[0102] In a preferred embodiment of the invention, at least one photoactive layer is an absorber layer; preferably, at least one compound is an absorber material.

[0103] At least one photoactive layer in the form of a planar heterojunction (PHJ) has a donor layer having at least one compound according to the invention as a donor; and an acceptor layer arranged on the donor layer, preferably directly on the donor layer, and having at least one acceptor; preferably, the acceptor is a fullerene, particularly preferably C60, or a fullerene derivative. The acceptor may alternatively be a non-fullerene acceptor (NFA).

[0104] In an alternative embodiment of the present invention, at least one photoactive layer in the form of a planar heterojunction (PHJ) has an acceptor layer which comprises at least one compound according to the invention as acceptor.

[0105] In a preferred embodiment of the invention, the donor layer of the PHJ cell has a layer thickness of 5 nm to 50 nm, preferably 5 to 20 nm, preferably 7 to 15 nm.

[0106] In a preferred embodiment of the invention, the acceptor layer of the PHJ cell has a layer thickness of 5 nm to 50 nm, preferably 7 to 15 nm, preferably 5 to 20 nm.

[0107] In a preferred embodiment of the invention, the layer system of the optoelectronic component has at least two photoactive layers, preferably at least three photoactive layers or preferably at least four photoactive layers.

[0108] In a preferred embodiment of the present invention, the compound and / or the layer comprising at least one compound is deposited by vapor deposition or solvent processing, more preferably by vacuum processing.

[0109] The objects of the present invention are also achieved by providing the use of at least one compound according to the invention in an optoelectronic component, preferably an organic optoelectronic component, in particular a photoactive layer in the form of a planar heterojunction (PHJ) according to one of the above working examples. The use of the at least one compound in an optoelectronic component in particular produces the advantages already explained in conjunction with the optoelectronic component according to the invention comprising the at least one compound.

[0110] In one development of the invention, it is the case that the compounds according to the invention are used in an organic optoelectronic component, preferably an organic photovoltaic element, an OLED, an OFET, or an organic photodetector.

[0111] In a preferred embodiment of the present invention, at least one compound according to the present invention is used as absorber material in a photoactive layer of an optoelectronic component.In a preferred embodiment of the present invention, the compound according to the present invention is used as donor in a donor-acceptor heterojunction.

[0112] In a preferred embodiment of the invention, the optoelectronic component comprises a substrate, wherein the first electrode or the second electrode is arranged on the substrate; in particular, one of the electrodes of the optoelectronic component can be applied directly to the substrate, wherein the layer system is arranged between the first electrode and the second electrode.

[0113] The object of the present invention is also achieved by providing a compound of the general formula II, in particular according to one of the working examples described above. For the compound of the general formula II, the advantages already explained in conjunction with the optoelectronic component of the invention occur in particular.

[0114]

[0115] Wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3;

[0116] Wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3;

[0117] Wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3;

[0118] Where Z1 and Z2 are F or CF3;

[0119] wherein X1 and X2 are independently O, S or N-R8, wherein R8 is selected from the group consisting of H, alkyl and aryl, wherein, preferably, X1 and X2 are S or X1 and X2 are O;

[0120] wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3;

[0121] wherein R13 and R15 are independently selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl;

[0122] wherein R14 and R16 are independently selected from the group consisting of: unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5-membered or 6-membered rings, preferably having heteroatoms independently selected from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered rings, preferably selected from unsubstituted and substituted heterocyclic 5-membered rings and unsubstituted and substituted homocyclic 6-membered rings.

[0123] In a preferred embodiment of the present invention, in the compound with general formula II, R14 and R16 are substituted heterocyclic 5-membered rings, wherein at least one hydrogen atom, preferably one hydrogen atom in the heterocyclic 5-membered ring is substituted, preferably substituted by a substituent selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl. In a preferred embodiment of the present invention, R14 and / or R16 have no additional fusion.

[0124] In a preferred embodiment of the present invention, in the compound having the general formula II, X1 and X2 are S or X1 and X2 are O; particularly preferably, X1 and X2 are O.

[0125] In a preferred embodiment of the present invention, in the compound having the general formula II, in R14 and R16, at least one hydrogen atom of the homocyclic 6-membered ring and / or the heterocyclic 5-membered ring or 6-membered ring is substituted by F or CF3, preferably by F.

[0126] In a preferred embodiment of the present invention, in the compound having the general formula II, R13 and R15 are H.

[0127] In a preferred embodiment of the present invention, in the compound having the general formula II, R13 and R15 are the same, and / or R14 and R16 are the same.

[0128] In a preferred embodiment of the present invention, in the compound having the general formula II, Z1 is the same as Z2, R13 is the same as R15, and R14 is the same as R16.

[0129] In a preferred embodiment of the present invention, in the compound having the general formula II, X1 and X2 are O or S, R13 and R15 are H, and R14 and R16 are unsubstituted or substituted heterocyclic 5-membered ring or 6-membered ring, preferably having heteroatoms selected from S, O and N, or unsubstituted or substituted homocyclic 6-membered ring, preferably substituted heterocyclic 5-membered ring.

[0130] In a preferred embodiment of the present invention, in the compounds of the general formula II, R13 and R14 and / or R15 and R16 in each case form an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from S, O and N, or an unsubstituted or substituted homocyclic 6-membered ring.

[0131] In a preferred embodiment of the present invention, in the compounds of the general formula II, R13 and R14 and / or R15 and R16 in each case form an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N.

[0132] In a preferred embodiment of the present invention, the compound having the general formula II does not have a ring structure between R13 and R14 and / or between R15 and R16.

[0133] In a preferred embodiment of the present invention, in the compound having the general formula II, R14 and R16 are independently selected from the group consisting of:

[0134]

[0135] wherein X3 is O, S, or N-R9, wherein R9 is selected from the group consisting of H, alkyl, and aryl;

[0136] Wherein R17 to R19 and R31 to R35 are independently selected from the group consisting of: H, halogen, preferably F and Cl, CN, alkyl, preferably C1-C4-alkyl, O-alkyl, preferably O-C1-C4-alkyl, and S-alkyl, preferably S-C1-C4-alkyl, wherein preferably at least one hydrogen atom is substituted by F.

[0137] In a preferred embodiment of the present invention, in the compound having the general formula II, R17 and / or R18, preferably R17 and R18 are H.

[0138] In a preferred embodiment of the present invention, in the compound having the general formula II, at least R31 and R35 are H.

[0139] In a preferred embodiment of the present invention, in the compound having the general formula II, R31, R32, R34 and R35 are H.

[0140] In another preferred embodiment of the present invention, in the compound having the general formula II, R31 to R35 are H.

[0141] In another preferred embodiment of the present invention, in the compound having the general formula II, Z1 and Z2 are F, and R1 and R2 are independently selected from the group consisting of H, F, Cl and Br, with the proviso that at least R1 or R2 is Br or Cl.

[0142] In further preferred embodiments of the present invention, in compounds of formula II, Y1 and Y3 are CH and Y2 is CR22, preferably wherein CR22 is selected from the group consisting of F, Br, Cl and CN, or Y1 is CR21, Y2 is N and Y3 is CR23, preferably wherein CR21 and CR23 are H or methyl, or Y1 is N, Y2 is CR22 and Y3 is N, preferably wherein CR22 is H or methyl, wherein R1 and R2 are in each case preferably F or Cl.

[0143] In another preferred embodiment of the present invention, at least one compound is a compound having the general formula III

[0144]

[0145] Where X1 and X2 are independently O or S, wherein R 40 is H, Cl or F, preferably H, and wherein Hal is Br, Cl or F. In a particularly preferred embodiment of the present invention, the meso substituent on the BODIPY base skeleton is (4)-3,5-dichloropyridine, ie wherein each Hal═Cl and R40═H.

[0146] In another preferred embodiment of the present invention, at least one compound is a compound having the general formula IV

[0147]

[0148] Where X1 and X2 are independently O or S, wherein R 41 is H, Cl or F, preferably H, and wherein Hal is Br, Cl or F.

[0149] In another preferred embodiment of the present invention, at least one compound is a compound having the general formula V

[0150]

[0151] Where X1 and X2 are independently O or S, wherein R 42 is H, C1-C4-alkyl, Cl or F, and wherein Hal is Br, Cl or F.

[0152] In another preferred embodiment of the present invention, in the compound having the general formula II, R 14 and R 16is an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N, preferably O and S, wherein, preferably, R19, R17 and R19, or R18 and R19 are substituted, or an unsubstituted or substituted homocyclic 6-membered ring, wherein, preferably, R32, R33, or R32 and R34 are substituted, or R31 to R35 are H. BRIEF DESCRIPTION OF THE DRAWINGS

[0153] The present invention will be explained in detail below with reference to the accompanying drawings. The accompanying drawings show:

[0154] Figure 1 is a schematic cross-sectional view of a working example of an optoelectronic component;

[0155] Figure 2 is a schematic diagram of a working example of a synthetic scheme for synthesizing compounds of the present invention;

[0156] Figure 3 is a graph of current-voltage curves, spectral external quantum yield and fill factor of a PHJ cell comprising compound (40) measured on an organic optoelectronic component;

[0157] Figure 4 is a graph of the absorption spectrum of compound (40); and

[0158] Figure 5 is the maximum external quantum efficiency (EQE max ). DETAILED DESCRIPTION

[0159] Working Example

[0160] Figure 1 A schematic cross-sectional view of a working example of an optoelectronic component 10 is shown.

[0161] In this working example, the optoelectronic component 10 is an organic photovoltaic element.

[0162] The optoelectronic component 10 has a substrate 1. Arranged on top of the substrate 1 are a base electrode 2, a cover electrode 6 and a layer system 7 comprising at least one photoactive layer 4, wherein the layer system 7 is arranged between the base electrode 2 and the cover electrode 6. At least one photoactive layer 4 takes the form of a planar heterojunction (PHJ). At least one photoactive layer 4 in the form of a planar heterojunction has an acceptor layer and a donor layer. The donor layer of the photoactive layer 4 contains at least one compound having the general formula I as a donor. In this working example, the acceptor layer of the photoactive layer 4 has fullerene C60 as an acceptor; however, the acceptor can alternatively also be a fullerene derivative or a non-fullerene acceptor (NFA). The compound having the general formula I has the following structure:

[0163]

[0164] wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5;

[0165] wherein Z1 and Z2 are independently selected from the group consisting of: F, Cl, CN, CF3, C2F5, OCH3 and OC2H5;

[0166] wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3;

[0167] wherein R3 and R5 are independently selected from the group consisting of H, halogen, CN, unsubstituted and aryl- or heteroaryl-substituted alkyl, unsubstituted and aryl- or heteroaryl-substituted alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O or N, and unsubstituted and alkyl-substituted homocyclic 6-membered rings, wherein the unsubstituted or substituted heterocyclic 5- or 6-membered ring, or the unsubstituted or substituted homocyclic 6-membered ring may be fused to another unsubstituted or substituted heterocyclic 5- or 6-membered ring;

[0168] wherein R4 and R6 are independently selected from the group consisting of: H, halogen, CN, alkyl, alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O and N, and unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted homocyclic 6-membered rings;

[0169] wherein R3 and R4 and / or R5 and R6 can in each case together form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heterocyclic 5- or 6-membered ring, preferably with at least one heteroatom selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted homocyclic 6-membered ring.

[0170] The general preparation of the compounds according to the invention is known to the person skilled in the art from the prior art. In this context, reference is made in particular to the international applications WO 2007126052 A1 and EP 3617214 A1.

[0171] In one configuration of the invention, the optoelectronic component 10 comprises a layer system 7 having at least one light-absorbing photoactive layer 4 , wherein the at least one light-absorbing photoactive layer 4 comprises at least one compound of the general formula I.

[0172] In another configuration of the invention, the layer system 7 has at least two photoactive layers 4, preferably at least three photoactive layers 4 or preferably at least four photoactive layers 4. In a further configuration of the invention, the optoelectronic component 10 is formed as a double cell, triple cell or multicell.

[0173] In a working example, the organic photovoltaic element has a substrate 1 made of glass, but the substrate 1 can also be formed by a film, such as a PET film. On top of the substrate 1 is a base electrode 2, for example made of ITO. Arranged on the base electrode is a layer system 7, which has an electron transport layer 3 (ETL) and a photoactive layer 4 in the form of a planar heterojunction, the photoactive layer having at least one compound of the present invention as a donor material and an acceptor material, such as fullerene C60. Arranged above the photoactive layer is a p-doped hole transport layer 5 (HTL) and a top electrode 6 made of gold or aluminum.

[0174] In one configuration of the invention, the optoelectronic component 10 comprising a compound of the general formula I in a photoactive layer 4 in the form of a planar heterojunction is an organic optoelectronic component, preferably an organic photovoltaic element, an OFET, an OLED or an organic photodetector.

[0175] The organic material is printed, glued, coated, vapor deposited or otherwise applied to the foil in the form of a thin film or small volume. Useful methods for producing thin layers are likewise those which are also used for electronic devices on glass, ceramic or semiconductor supports. In the present working example, vacuum evaporation is used to produce the layer system.

[0176] Figure 2 Schematic representation showing a working example of a synthetic scheme for synthesizing compounds of the invention.

[0177] The experimental procedure for synthesizing compounds of general formula I is shown in Figure 2 .

[0178] General Procedure for Step 2-A:

[0179] Aldehyde A (1.00 equivalent) is dissolved / suspended in 9vol anhydrous ethanol. Ethyl trifluoroacetate (1.50 equivalent) is added, and the resulting mixture is cooled to 0°C. Subsequently, sodium ethoxide solution (21wt%, 1.50 equivalent) is added, and after 5min, ethyl 2-azidoacetate (1.50 equivalent) is gradually added in 10min at a temperature below 5°C. The mixture is then stirred at 0°C for 30min and gradually warmed to room temperature while continuing to stir for 4 hours. The reaction mixture is dissolved in 21vol ethanol, and the precipitate is filtered out and washed with cooling anhydrous ethanol to obtain intermediate B.

[0180] General Procedure for Step 2-B:

[0181] Intermediate B is dissolved in toluene, and the resulting solution is dried over anhydrous sodium sulfate and filtered. Under argon, 43vol anhydrous toluene is loaded into a flask and heated under reflux. The solution of intermediate B is introduced into a dropping funnel, and gradually added to the toluene heated under reflux in 15min. The resulting solution is heated for another 15min. The solvent is removed under reduced pressure to obtain a brown solid as a crude product. The crude product is suspended in 8vol petroleum ether, and is processed with ultrasound. The resulting precipitate is filtered out, washed with petroleum ether and dried under reduced pressure to obtain pyrrole ester C.

[0182] General Procedure for Step 3-A:

[0183] Pyrrolyl ester C (1.00 eq) was suspended in 19 vol ethanol and 5.0 eq of NaOH in 4 vol water was added. The mixture was stirred at 75° C. for 1 hour and then 7.0 eq of AcOH in 11 vol water was added to obtain a pH of about 4. The product was filtered off and washed with water and then toluene to give pyrrolyl acid D.

[0184] General Procedure for Step 3-B:

[0185] Pyrrolic acid D (1.00 equivalent) was dissolved in 21 vol ethanolamine. The mixture was heated to 150°C and stirred for 4 hours. After cooling to 50°C, 32 vol heptane was added. The mixture was further cooled to 10°C, and the product was filtered off, washed with water and heptane and dried under reduced pressure to give pyrrole E.

[0186] General procedure for step 4:

[0187] Pyrrole E (2.00 eq.) and aldehyde (1.00 eq.) were dissolved / suspended in 30 vol of dichloromethane. Trifluoroacetic acid (0.10 eq.) was added dropwise at room temperature and the mixture was stirred for 3 hours. Chloroquinone (1.05 eq.) was added dropwise over 5 min and the mixture was mixed at room temperature for 30 min. The mixture was diluted with 25 vol of methanol and then concentrated under reduced pressure (40 ° C. in a water bath) to remove dichloromethane to a large extent. Subsequently, the resulting suspension was stirred at 0 ° C. for 90 min and then filtered. The separated solid was washed with cold methanol and dried under reduced pressure to obtain dipyrrin F.

[0188] General procedure for step 5 (synthesis):

[0189] Dipyrromethene F (1.00 equiv) was suspended in 42 vol of anhydrous toluene. The mixture was stirred at 55°C, and N,N-diisopropylethylamine (1.50 equiv) was added. A solution of boron trifluoride diethyl ether (4.00 equiv) in 10 vol of anhydrous toluene was gradually added. The mixture was stirred at 55°C until the dissolution was complete. The reaction mixture was cooled to 0°C and stirred at this temperature for one hour. The precipitate was filtered, washed with toluene and methanol, and then dried under reduced pressure to obtain crude BODIPY G. The crude BODIPY G was purified by recrystallization, and purified BODIPY G was obtained.

[0190] Synthesis of compounds:

[0191] Synthesis of 5-phenylfuran-2-carboxaldehyde A-1

[0192]

[0193] The synthesis of 5-phenylfuran-2-carbaldehyde A-1 can be carried out according to Li et al. (J. Am. Chem. Soc [Journal of the American Chemical Society]. 2017, 139(39), 13636-13639).

[0194] Synthesis of pyrrolyl ester C-1

[0195]

[0196] According to step 2-A and step 2-B, compound 5-phenylfuran-2-carbaldehyde A-1 (8.61 g, 50.0 mmol) was used to isolate compound C-1 (8.33 g, 65% yield) in the form of a white to light brown solid. 1H NMR (400 MHz, acetone-d6) δ 10.70 (m, 1H), 7.82 (m, 2H), 7.44 (m, 2H), 7.32 (m, 1H), 7.03 (m, 1H), 6.78 (m, 1H), 4.30 (q, J = 8.0 Hz, 2H), 1.33 (t, J = 8.0 Hz, 3H).

[0197] Synthesis of Pyrrolic Acid D-1

[0198]

[0199] According to the general method of step 3-A, using pyrrolyl ester C-1 (58.0 g, 0.227 mol), compound D-1 (50.3 g, 97% yield) was isolated as a beige solid.

[0200] Synthesis of Pyrrole E-1

[0201]

[0202] According to the general method of step 3-B, pyrrolic acid D-1 (50.0 g, 0.220 mol) was used to isolate compound E-1 (36.6 g, 91% yield) in the form of a light brown solid. 1H NMR (400 MHz, acetone-d6) δ 9.86 (m, 1H), 7.73 (m, 2H), 7.37 (m, 2H), 7.21 (m, 1H), 6.96 (m, 1H), 6.88 (m, 1H), 6.11 (m, 1H).

[0203] Synthesis of Dipyrromethene F-1

[0204]

[0205] According to the general procedure of step 4, using pyrrole E-1 (5.13 g, 28.0 mmol) and 3,5-dichloro-4-pyridinecarboxaldehyde (2.54 g, 14.0 mmol), compound F-1 (6.30 g, 86% yield) was isolated as a green crystalline solid.

[0206] Synthesis of BODIPY G-1

[0207]

[0208] Compound G-1 was isolated according to the general procedure of step 5 using dipyrromethene F-1 (6.30 g, 12.1 mmol) and purified by recrystallization in toluene (800 ml). A green crystalline solid was obtained (4.10 g, 60% yield).

[0209] Figure 3 A graph showing the current-voltage curve, the spectral external quantum efficiency and the fill factor of a PHJ cell comprising compound (40) measured on an organic optoelectronic component 10 is shown. Identical and functionally identical elements are given the same reference numerals and reference is therefore made to the above description in this respect. In this working example, the optoelectronic component 10 is an organic photovoltaic element.

[0210] In order to examine these compounds, ie their use as absorber materials in organic optoelectronic components 10, the current-voltage curves of PHJ cells were measured ( Figure 3 A), and plotted the external quantum yield as a function of wavelength ( Figure 3 B). The current-voltage curve contains indicators that characterize organic photovoltaic devices. The most important indicators here are the fill factor FF, the open circuit voltage U oc and short-circuit current Jsc.

[0211] The current-voltage curve of the PHJ cell with the following configuration was determined: glass with ITO / C60 (15 nm) / compound (40) (10 nm, RT) / NHT169 (10 nm) / NHT169:NDP9 (45 nm, 9.9 wt%) / NDP9 (1 nm) / Au (50 nm). Under AM1.5 illumination (AM = air mass; AM = 1.5; in this spectrum, the global radiant power is 1000 W / m 2 ; AM = 1.5 as a standard value for analyzing solar modules), wherein the photoactive layer includes a planar heterojunction (PHJ). In the photoactive layer 4, the donor layer of compound (40) and the acceptor layer of C60 are applied separately in the form of a planar heterojunction. ITO is used as the substrate electrode 2 here, and the adjacent fullerene C60 is used as the electron transport layer (ETL) 3, adjacent to which is the photoactive layer 4 having an acceptor layer and a donor layer arranged on the electron transport layer 3, followed by NHT169 as a hole transport layer (HTL) 5 and NDP9-doped NHT169. The top electrode is formed of gold. NDP9 is a commercial p-dopant from Novaled GmbH. NHT169 is an HTL matrix material from Novaled GmbH.

[0212] The individual layers of the optoelectronic component 10, in particular the photoactive layer 4, can be applied under reduced pressure by evaporating the corresponding materials. Compound (40) exhibits good evaporability under reduced pressure.

[0213] In an optoelectronic component containing the compound (40) in a planar heterojunction, the fill factor FF is 73.1% and the open circuit voltage U oc The EQE of this organic photovoltaic element is 0.99 V and the short-circuit current Jsc is 11.2 mA / cm2. max It is 84%.

[0214] Figure 4 A diagram showing the absorption spectrum of compound (40) is shown. Identical and functionally identical elements are given the same reference numerals, and reference is therefore made to the above description in this respect.

[0215] The structure of the optoelectronic component 10 corresponds to Figure 2 structure; the donor in the photoactive layer 4 in the form of a planar heterojunction is also compound (40).

[0216] The absorption maximum λmax of compound (40) is 743 nm.

[0217] Figure 5 The maximum external quantum yield (EQEmax) of a number of working examples of the compounds according to the invention in an optoelectronic component 10 is shown. Identical and functionally identical elements are given the same reference numerals and reference is therefore made to the above description in this respect. In the working example, the optoelectronic component 10 is an organic photovoltaic element.

[0218] The structure of the optoelectronic component 10 corresponds to Figure 2 of structures in which the donors in the photoactive layer 4 , in each case in the form of a planar heterojunction, are different.

[0219] The following donors from the compounds of the invention having the general formula I were used:

[0220]

[0221]

[0222]

[0223]

[0224] Table 1 shows the absorption maximum λmax of various compounds of the present invention in the film. The optical properties were determined experimentally. The absorption maximum λmax was determined by a photometer from a 30 nm thick vacuum vapor deposition layer on quartz glass. Table 1 shows the photovoltaic parameters Uoc, Jsc and FF of various compounds of the present invention and the corresponding EQE max The maximum EQE is called EQE max, and is the basic parameter used to describe the efficiency of photovoltaic elements. The efficiency of photovoltaic elements increases with the EQE of the corresponding spectral region. max The EQE of the compounds of the present invention max In the range of 60% to 84%.

[0225] Table 1

[0226]

[0227]

[0228] The EQE of a specific working example of the compound of the present invention having the general formula I in a PHJ cell of an organic photovoltaic element, according to the meso group and the side groups on the BODIPY basic skeleton (corresponding to R14 / R16 of the compound having the general formula III) is max An overview of Figure 5 The PHJ cells containing the compounds according to the invention show particularly high EQE max , especially compared to non-inventive compounds, especially non-inventive BODIPY compounds that do not have the structural features of the invention at the meso position.

[0229] Experimental data of the compounds according to the invention in a photoactive layer 4 in the form of a planar heterojunction in an organic photovoltaic element demonstrate that the compounds according to the invention have very good suitability as absorber materials in a planar heterojunction and lead to photovoltaic elements having such a photoactive layer 4 having improved efficiencies.

Claims

1. An optoelectronic component, preferably a photovoltaic element, having a base electrode, a top electrode and a layer system having at least one photoactive layer, wherein the layer system is arranged between the base electrode and the top electrode, wherein the at least one photoactive layer is in the form of a planar heterojunction (PHJ), and wherein the at least one photoactive layer in the form of a planar heterojunction comprises at least one compound of the general formula I Wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; Wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; Wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN, CF3 or SF5; wherein Z1 and Z2 are independently selected from the group consisting of: F, Cl, CN, CF3, C2F5, OCH3 and OC2H5; wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3; wherein R3 and R5 are independently selected from the group consisting of H, halogen, CN, unsubstituted and aryl- or heteroaryl-substituted alkyl, unsubstituted and aryl- or heteroaryl-substituted alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O or N, and unsubstituted and alkyl-substituted homocyclic 6-membered rings, wherein the unsubstituted or substituted heterocyclic 5- or 6-membered ring, or the unsubstituted or substituted homocyclic 6-membered ring may be fused to another unsubstituted or substituted heterocyclic 5- or 6-membered ring; wherein R4 and R6 are independently selected from the group consisting of: H, halogen, CN, alkyl, alkenyl, O-alkyl, S-alkyl, preferably unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5- and 6-membered rings having at least one heteroatom selected from S, O and N, and unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted homocyclic 6-membered rings; Or wherein R3 and R4 and / or R5 and R6 in each case together form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted heterocyclic 5- or 6-membered ring, preferably with at least one heteroatom selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted homocyclic 6-membered ring.

2. The optoelectronic component according to claim 1, wherein Z1 and Z2 are F; and / or wherein R1 and R2 are independently selected from the group consisting of H, F, Cl, Br, CN, CF3, Me, Et, OMe, SMe, OEt, SEt, Pr, and iPr, provided that at least R1 or R2 is Br or Cl, wherein, preferably, R1 and R2 are not H; or wherein R1 and R2 are independently selected from the group consisting of Cl, Br, CF3, CN, Me, Et, OMe, SMe, OEt, and SEt, provided that at least R1 or R2 is Cl, Br, CF3 or Me; or wherein R1 and R2 are selected from the group consisting of Br, Cl, CF3, CHF2 and CH2F.

3. The optoelectronic component according to claim 1 or 2, wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H or Cl, and / or wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, CH3, O-CH3, S-CH3, F, Cl, CF3 or SF5, preferably N or CH, and / or wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H or Cl; in, Preferably, one Y1, Y2, Y3 is N, or two Y1, Y2, Y3 are N.

4. The optoelectronic component as claimed in any one of the preceding claims, wherein R3 and R4 and / or R5 and R6 form an unsubstituted or substituted heterocyclic 5-membered ring or 6-membered ring having at least one heteroatom selected from O, S and N, preferably selected from O and S, or an unsubstituted or substituted homocyclic 6-membered ring, or wherein R3 and R4 and / or R5 and R6 form an unsubstituted or substituted heterocyclic 5-membered ring, preferably a substituted heterocyclic 5-membered ring, or an unsubstituted or substituted homocyclic 6-membered ring, preferably an unsubstituted homocyclic 6-membered ring, having at least one heteroatom selected from O, S and N, preferably O and S.

5. The optoelectronic component as claimed in any one of the preceding claims, wherein The at least one compound is a compound having the general formula II Wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Where Z1 and Z2 are F or CF3; wherein X1 and X2 are independently O, S or N-R8, wherein R8 is selected from the group consisting of H, alkyl and aryl, wherein preferably, X1 and X2 are S or X1 and X2 are O; wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CH2F, CHF2 or CH3; wherein R13 and R15 are independently selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl; wherein R14 and R16 are independently selected from the group consisting of: unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5-membered or 6-membered rings, preferably having heteroatoms independently selected from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered rings, preferably selected from unsubstituted and substituted heterocyclic 5-membered rings and unsubstituted and substituted homocyclic 6-membered rings.

6. The optoelectronic component according to claim 5, wherein: R14 and R16 are independently selected from the group consisting of: wherein X3 is O, S, or N-R9, wherein R9 is selected from the group consisting of H, alkyl, and aryl; Wherein R17 to R19 and R31 to R35 are independently selected from the group consisting of: H, halogen, preferably F and Cl, CN, alkyl, preferably C1-C4-alkyl, O-alkyl, preferably O-C1-C4-alkyl, and S-alkyl, preferably S-C1-C4-alkyl, wherein preferably at least one hydrogen atom is substituted by F.

7. The optoelectronic component according to claim 5 or 6, wherein: Z1 and Z2 are F, and wherein R1 and R2 are independently selected from the group consisting of H, F, Cl, Br, CH3, CH2F, CHF2 and CF3, with the proviso that at least R1 or R2 is Br, Cl or CF3.

8. An optoelectronic component as claimed in any one of the preceding claims, wherein Y1 and Y3 are CH and Y2 is CR22, preferably wherein CR22 is selected from F, Br, Cl and CN, or Y1 is CR21, Y2 is N and Y3 is CR23, preferably wherein CR21 and CR23 are H or methyl, or Y1 is N, Y2 is CR22 and Y3 is N, preferably wherein CR22 is H or methyl.

9. The optoelectronic component as claimed in any one of the preceding claims, wherein The at least one compound is a compound having the general formula III Where X1 and X2 are independently O or S, wherein R 40 is H, Cl or F, preferably H, and wherein Hal is Br, Cl or F.

10. The optoelectronic component as claimed in any one of the preceding claims, wherein The at least one compound is a compound having the general formula IV Where X1 and X2 are independently O or S, wherein R 41 is H, F, Cl, Br, CF3 or C1-C4-alkyl, preferably H or Cl, and wherein Hal is Br, Cl or F.

11. An optoelectronic component as claimed in any one of the preceding claims, wherein The at least one compound is a compound having the general formula V Where X1 and X2 are independently O or S, wherein R 42 is H, F, Cl, CF3 or C1-C4-alkyl, and wherein Hal is Br, Cl or F.

12. An optoelectronic component as claimed in any one of the preceding claims, wherein: R 14 and R 16 is independently an unsubstituted or halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N, preferably O and S, wherein preferably R19, or R17 and R19, or R18 and R19 are substituted, or unsubstituted or halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered ring, wherein, preferably, R32, R33, or R32 and R34 are substituted, or preferably, R31 to R35 are H.

13. An optoelectronic component as claimed in any one of the preceding claims, wherein: The compound is selected from the group consisting of:

14. Use of at least one compound according to any one of claims 1 to 13 in a photoactive layer in the form of a planar heterojunction (PHJ) in an optoelectronic component, preferably an organic optoelectronic component, wherein The organic optoelectronic component is preferably an organic photovoltaic element, an OLED, an OFET, or an organic photodetector.

15. A compound having the general formula II Wherein Y1 is selected from the group consisting of N and CR21, wherein R21 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Wherein Y2 is selected from the group consisting of N and CR22, wherein R22 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Wherein Y3 is selected from the group consisting of N and CR23, wherein R23 is H, alkyl, O-alkyl, S-alkyl, halogen, preferably F or Cl, CN or CF3; Where Z1 and Z2 are F or CF3; wherein X1 and X2 are independently O, S or N-R8, wherein R8 is selected from the group consisting of H, alkyl and aryl, wherein Preferably, X1 and X2 are S or X1 and X2 are O; wherein R1 and R2 are independently selected from the group consisting of: H, F, Cl, Br, CN, CF3, CHF2, CH2F, C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl), provided that at least R1 or R2 is Br, Cl, CF3, CHF2, CH2F or CH3; wherein R13 and R15 are independently selected from the group consisting of: H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl; wherein R14 and R16 are independently selected from the group consisting of: unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5-membered or 6-membered rings, preferably having heteroatoms independently selected from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted homocyclic 6-membered rings, preferably selected from unsubstituted and substituted heterocyclic 5-membered rings and unsubstituted and substituted homocyclic 6-membered rings.

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