Optoelectronic component having a photoactive layer designed as a planar heterojunction

Abstract

The present invention relates to an optoelectronic component comprising a layer system (7) having a bottom electrode (2), a top electrode (6), and 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), where at least one photoactive layer designed as a planar heterojunction has at least one chemical compound of general formula I. The present invention also relates to the use of such a compound of general formula I in an optoelectronic component and to a chemical 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 contains a chemical compound of general formula I, and the present invention further relates to the use of such a compound of general formula I in an optoelectronic component.

Background Art

[0002] Optoelectronic components can be displays, data storage media or transistors, but can also be photovoltaic devices, especially solar cells and photodetectors, which have a photoactive layer in which electron-hole pairs (excitons) are formed by the incidence of electromagnetic waves. The excitons reach an interface where the electrons and holes are separated from each other by diffusion. The material that accepts electrons is called an acceptor, and the material that accepts holes is called a donor. Organic optoelectronic components utilize the photovoltaic effect to achieve the conversion of electromagnetic waves into an electric current. For this type of conversion of electromagnetic waves, an absorbing material showing good absorption characteristics is required.

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

[0004] Patent Document 1 discloses a photoactive component, especially a solar cell, consisting of one or more organic layers of pi, ni and / or pin diodes laminated on each other.

[0005] Patent Document 2 discloses the structure of an organic solar cell as a pin or nip diode. A pin solar cell typically consists of a substrate on which a transparent electrode is disposed, a p-layer, an i-layer, an n-layer, and a counter electrode. In this context, n and p respectively mean n- and p-doping, which result in an increase in the free electron / hole density in the thermal equilibrium state. Such layers should be mainly understood as transport layers. The term "i-layer" refers to an undoped layer (intrinsic layer) having a single absorption material or a mixture of two or more absorption materials (planar heterojunction). Here, one or more i-layers can be composed of a mixture of two or more materials (bulk heterojunction) containing at least one donor and at least one acceptor. In particular, an absorption material, that is, an absorber, means a compound that absorbs light within a specific wavelength range. Thus, in particular, an absorber layer means a layer in an optoelectronic component containing at least one absorption material.

[0006] In the prior art, numerous polymeric and non-polymeric absorption materials for organic optoelectronic devices in the red and near-infrared (NIR) regions of approximately 600 to approximately 1400 nm have been disclosed. In the field of non-polymeric absorption materials, in particular, materials from the BODIPY substance classification have been found to be suitable in the near-infrared spectral region, which means that suitable energy levels, and thus high optoelectromotive force, can be achieved simultaneously in the long-wavelength absorption region.

[0007] Patent Document 3 discloses an organic electronic component comprising at least one organic layer between two electrodes, and the organic layer contains at least one compound from the group of BODIPY.

[0008] Non-Patent Document 1 discloses 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 of electronic components. Known absorption materials exhibit particularly low efficiency. The efficiency of an organic photovoltaic device depends on factors including the absorption characteristics of the organic material in the photoactive layer, i.e., the absorption material. Known absorption materials are suitable for the photoactive layer in an organic photovoltaic device, i.e., an organic solar cell, but there is a need for improvement in the absorption characteristics of the absorption material.

[0010] However, planar heterojunctions (PHJs) have the drawback of not being suitable for use in electronic components, particularly photovoltaic devices, which is especially because, presumably as a result of the limited exciton diffusion distance in such layers, the efficiency of the photovoltaic device has been greatly limited. Therefore, hitherto, PHJ cells have not been an option for industrial use in photovoltaic devices.

[0011] However, it would be desirable to use PHJs in photovoltaic devices in order to improve the efficiency of the photovoltaic devices and simplify their manufacture. In particular, there is a need for absorption materials that have high absorption in the red and near-infrared spectral regions and thus result in high efficiency in PHJs. In a BHJ, each component must form microdomains interconnected by a closed percolation path; otherwise, charge transport does not occur. Here, a particularly relevant factor is the size of the individual microdomains, and if the individual domains are too large, it leads to a loss of photocurrent. The optimal process parameters for its manufacture are difficult to achieve, and thus the industrially achievable efficiency of BHJs is inferior to what is possible under idealized laboratory conditions. In contrast, PHJs have significantly lower requirements for process parameters because they have fewer degrees of freedom to control the morphology of the individual layers compared to BHJs.

Prior Art Documents

Patent Documents

[0012]

Patent Document 1

[0013] [Non-Patent Document 1] Bartelmess et al. (“meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties”, New Journal of Chemistry, 2013, 37(9), 2663-2668) [Non-Patent Document 2] Li et al. (J. Am. Chem. Soc. 2017, 139(39), 13636-13639) [Summary of the Invention] [Problems to be Solved by the Invention]

[0014] Accordingly, an object of the present invention is to provide an optoelectronic component having at least one photoactive layer in the form of a planar heterojunction containing a chemical compound of general formula I, and to provide the use of the chemical compound of general formula I in the photoactive layer in the form of a planar heterojunction in an optoelectronic component, wherein the above disadvantages do not occur, and in particular, the use of a planar heterojunction is possible without limiting the efficiency of the photovoltaic device during the process. [Means for Solving the Problems]

[0015] This object is achieved by the subject matter of the independent claims. Advantageous configurations are apparent from the dependent claims.

[0016] This object is achieved in particular by providing an optoelectronic component, preferably a photovoltaic cell, having a layer system with a base electrode, a top electrode, and at least one photoactive layer, the layer system being arranged between the base electrode and the top electrode, where at least one photoactive layer is in the form of a planar heterojunction (PHJ), and where at least one photoactive layer in the form of a planar heterojunction comprises at least one chemical compound of general formula I

Chemical formula

[0017] In particular, substitution means the replacement of H by a substituent. In particular, a substituent means any atom and atomic group other than hydrogen, preferably a halogen, preferably F, Cl or Br, particularly preferably F, an alkyl group, where the alkyl group can 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.

[0018] In particular, a heteroatom means, in particular, with respect to the heteroatom in general formula I, an atom selected from the group consisting of O, S, Se and N.

[0019] In a preferred embodiment of the present invention, Y1 is selected from the group consisting of N and CR 21 wherein R 21 is H, C1-C4-alkyl, or a halogen, preferably F or Cl; Y2 is selected from the group consisting of N and CR 22 wherein R 22 is H, alkyl, O-alkyl, S-alkyl, a halogen such as preferably F or Cl, CN, CF3 or SF5; and Y3 is selected from the group consisting of N and CR 23 wherein R 23 is H, C1-C4-alkyl, or a halogen, preferably F or Cl.

[0020] In a preferred embodiment of the present invention, R 1 and R 2 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, provided that at least R 1 or R 2 is Br, Cl or CF3.

[0021] In a preferred embodiment of the present invention, in the substituted alkenyl, O-alkyl or S-alkyl at R3 and R5, the hydrogen atom is preferably substituted with a group selected from an unsubstituted and substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from S, O and N, and an unsubstituted and substituted monocyclic 6-membered ring.

[0022] In a preferred embodiment of the present invention, R 3 and / or R 5 In, the unsubstituted or substituted heterocyclic 5-membered or 6-membered ring, or the unsubstituted or substituted monocyclic 6-membered ring is preferably further condensed to at least one further heterocyclic 5-membered or 6-membered ring, or at least one monocyclic 6-membered ring, preferably an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S and O.

[0023] In a preferred embodiment of the present invention, R 3 and R 4 , and / or, R 5 and R 6 In each case, together, preferably form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted monocyclic 6-membered ring.

[0024] In a preferred embodiment of the present invention, R 3 and R 4 , and / or, R 5 and R 6 The unsubstituted or substituted heterocyclic 5-membered or 6-membered ring, or the unsubstituted or substituted monocyclic 6-membered ring formed between has no further condensation.

[0025] In a preferred embodiment of the present invention, R 4 and R 6is independently selected from the group consisting of H, halogen, CN, and unsubstituted and substituted alkyl. In a particularly preferred embodiment, R 4 and R 6 are H.

[0026] In a preferred embodiment of the present invention, R 4 and R 6 are the same, and / or R 3 and R 5 are the same.

[0027] In a preferred embodiment of the present invention, Z1 is the same as Z2, R 3 is the same as R 5 and R 4 is the same as R 6 and the same.

[0028] In particular, an optoelectronic component means a photovoltaic device having at least one organic photoactive layer, and the organic photoactive layer contains at least one compound of the present invention. The organic photovoltaic device utilizes the photovoltaic effect and enables the conversion of electromagnetic waves, particularly within the visible light wavelength range, into an electric current. In this context, the term "photoactive" means the conversion of light energy into electrical energy. In contrast to inorganic solar cells, in the case of organic photovoltaic devices, free charge carriers are not directly generated by light, but first excitons are formed, i.e., an electrically neutral excited state (bound electron-hole pair) is formed. Only in a second step are these excitons separated into free charge carriers at a photoactive donor-acceptor junction and then contribute to the flow of current.

[0029] The optoelectronic component of the present invention has advantages compared to the prior art. Advantageously, it is possible to provide an improved absorber for planar heterojunctions in optoelectronic components. Due to the limited diffusion distance in planar heterojunctions that limits the efficiency of optoelectronic components based on planar heterojunctions, planar heterojunctions have not been usable without difficulties until now. However, compared to bulk heterojunctions, the use of planar heterojunctions in optoelectronic components is desirable because the manufacturing is easy. Advantageously, the compound of the present invention enables an improvement in EQE max (maximum external quantum efficiency) in optoelectronic components having planar heterojunctions. Advantageously, the compound of the present invention enables the use of planar heterojunctions in commercially available optoelectronic components that can be manufactured particularly more easily compared to bulk heterojunctions. Advantageously, absorption materials for the red and near-infrared spectral regions having high absorption intensity and particularly good evaporability are provided for planar heterojunctions, and these can also be processed without decomposition particularly even under reduced pressure. Advantageously, the configuration of the groups at the meso position of the BODIPY basic skeleton brings about a preferred spatial arrangement of the compound particularly in the photoactive layer. The improved effect of the PHJ cell seems to be due to an increase in the exciton diffusion distance. Advantageously, the compound of the present invention shows very good properties in planar heterojunctions (PHJ), particularly enabling a larger layer thickness, and as a result, enabling a higher efficiency of the solar cell.

[0030] In a preferred embodiment of the present invention, Z1 and Z2 are each F or CF3.

[0031] In a particularly preferred embodiment of the present invention, R 1 and R 2 in C1-C4-alkyl, O-C1-C4-alkyl, S-C1-C4-alkyl and N-(C1-C4-alkyl)2 are preferably F, Cl, CN, CF3 and COR 8 (where R 8 is C1-C4-alkyl) are substituted with substituents selected from the group consisting of.

[0032] In one development form of the present invention, it is as follows: Z1 and Z2 are F; and / or, R 1 and R 2 are independently selected from the group consisting of H, F, Br, Cl, CN, Me, Et, OMe, SMe, OEt, SEt, Pr and iPr, provided that at least R 1 or R 2 is Br, Cl or CF3, where preferably, R 1 and R 2 is not H; or, R 1 and R 2 are independently selected from the group consisting of Cl, Br, CF3, CN, Me, Et, OMe, SMe, OEt and SEt, provided that at least R 1 or R 2 is Cl, Br, CF3 or Me; or, preferably, R 1 and R 2 are selected from the group consisting of Br, Cl, CF3, CHF2, CH2F and CH3.

[0033] In a particularly preferred embodiment of the present invention, R 1 and R 2 are independently selected from the group consisting of Cl, CN, Me, Et, OMe, SMe, OEt and SEt, provided that at least R 1 or R 2 is Cl.

[0034] In one development form of the present invention, it is as follows: Y1 is selected from the group consisting of N and CR 21 , where R 21 is H or Cl, and / or, Y2 is selected from the group consisting of N and CR 22 , where R 22 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 CR 23 , where R 23is H or Cl; wherein preferably, one of Y1, Y2, Y3 is N, or two of Y1, Y2, Y3 are N.

[0035] In a preferred embodiment of the present invention, Y1 is N or CH, and / or Y2 is N, CH or C-halogen, preferably C-F or C-Cl, and / or Y3 is N and CH, wherein preferably, at least one of Y1, Y2, Y3 is N, or at least two of Y1, Y2, Y3 are N.

[0036] 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 C-F 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 C-F or C-Cl, and Y3 is CH.

[0037] In one development form of the present invention, it is as follows: R 3 and R 4 and / or, R 5 and R 6 form an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having at least one heteroatom selected from O, S and N, preferably O and S, or an unsubstituted or substituted homocyclic 6-membered ring, or R 3 and R 4 and / or, R 5 and R 6 form an unsubstituted or substituted heterocyclic 5-membered ring, preferably a substituted heterocyclic 5-membered ring having at least one heteroatom selected from O, S and N, preferably O and S, or an unsubstituted or substituted homocyclic 6-membered ring, preferably an unsubstituted homocyclic 6-membered ring.

[0038] In a preferred embodiment of the present invention, R 3 and R4 and / or, R 5 and R 6 The heterocyclic 5- or 6-membered ring formed between them, preferably having at least one heteroatom selected from S, O, and N, and each being substituted, is substituted with one selected from the group consisting of halogen, CN, alkyl, O-alkyl, S-alkyl, unsubstituted and substituted heterocyclic 5- or 6-membered rings preferably having a heteroatom independently selected from S, O, and N, and unsubstituted and substituted monocyclic 6-membered rings. In a preferred embodiment of the present invention, the monocyclic 6-membered ring is unsubstituted.

[0039] In a preferred embodiment of the present invention, R 3 and R 4 and / or, R 5 and R 6 The substituted monocyclic 6-membered ring formed between them is substituted with one selected from the group consisting of halogen, CN, alkyl, O-alkyl, S-alkyl, unsubstituted and substituted heterocyclic 5- or 6-membered rings preferably having a heteroatom independently selected from S, O, and N, and unsubstituted and substituted monocyclic 6-membered rings. In a preferred embodiment of the present invention, the monocyclic 6-membered ring is unsubstituted.

[0040] In a preferred embodiment of the present invention, R 3 and R 4 and / or, R 5 and R 6 In each case, together form an unsubstituted or substituted heterocyclic 5- or 6-membered ring having at least one heteroatom selected from S, O, and N. In a preferred embodiment of the present invention, R 3 and R 4 and / or, R 5 and R 6 In each case, together form an unsubstituted or substituted furanyl ring or thienyl ring.

[0041] In a preferred embodiment of the present invention, R 3 and R 4 and / or, R 5and R 6 Alternatively, an unsubstituted or substituted heteroaryl 5-membered or 6-membered ring formed by an unsubstituted or substituted monocyclic 6-membered ring is fused to an unsubstituted or substituted thienyl ring or furanyl ring.

[0042] In a preferred embodiment of the present invention, R 3 and R 4 and / or R 5 and R 6 in each case together form an unsubstituted heteroaryl 5-membered or 6-membered ring preferably having at least one heteroatom selected from S, O and N.

[0043] In a preferred embodiment of the present invention, R 3 and R 4 and / or R 5 and R 6 in each case together form an unsubstituted or substituted monocyclic 6-membered ring, and R 3 and R 4 and / or R 5 and R 6 in each case together do not form a heteroaryl 5-membered or 6-membered ring.

[0044] In one development of the present invention, it is as follows: at least one chemical compound is a compound of general formula II [Chemical formula] (wherein Y1 is selected from the group consisting of N and CR 21 wherein R 21 is H, alkyl (preferably C1-C4-alkyl), O-alkyl, S-alkyl, or halogen, preferably F or Cl; Y2 is selected from the group consisting of N and CR 22 wherein R 22 is H, alkyl (preferably C1-C4-alkyl), O-alkyl, S-alkyl, halogen such as preferably F or Cl, CN or CF3; Y3 is N and CR23 selected from the group consisting of, wherein R 23 is H, alkyl (preferably C1-C4-alkyl), O-alkyl, S-alkyl, or halogen, preferably F or Cl; Z1 and Z2 are F or CF3; X1 and X2 are, independently, O, S or N-R 8 wherein R 8 is selected from the group consisting of H, alkyl and aryl, wherein preferably X1 and X2 are S, or X1 and X2 are O; R 1 and R 2 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, provided that at least R 1 or R 2 is Br, Cl, CF3, CHF2, CH2F or CH3, preferably Br or Cl; R 13 and R 15 are independently selected from the group consisting of H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl; R 14 and R 16 are preferably selected independently from S, O and N and have unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5- or 6-membered rings, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered rings, preferably selected independently from the group consisting of unsubstituted and substituted heterocyclic 5-membered rings, and unsubstituted and substituted monocyclic 6-membered rings) is.

[0045] In a preferred embodiment of the present invention, R 14 and R 16is a substituted complex cyclic 5-membered ring, wherein at least one hydrogen atom, preferably one hydrogen atom, in the complex cyclic 5-membered ring is preferably substituted with 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, R 14 and / or R 16 has no further condensation.

[0046] In a preferred embodiment of the present invention, R 14 and R 16 are independently an unsubstituted or substituted furanyl ring or thienyl ring.

[0047] 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.

[0048] In a preferred embodiment of the present invention, in R 14 and R 16 , at least one hydrogen atom of the monocyclic 6-membered ring and / or at least one hydrogen atom of the complex cyclic 5-membered ring or 6-membered ring is substituted with F or CF3, preferably F.

[0049] In a preferred embodiment of the present invention, R 13 and R 15 are H.

[0050] In a preferred embodiment of the present invention, R 13 and R 15 are the same, and / or R 14 and R 16 are the same.

[0051] In a preferred embodiment of the present invention, Z1 is the same as Z2, R 13 is the same as R 15 and, R 14 is the same as R 16 and the same.

[0052] In a preferred embodiment of the present invention, X1 and X2 are O or S, and R 13 and R 15 are H, and R 14 and R 16 are preferably an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having a heteroatom selected from S, O, and N, or an unsubstituted or substituted monocyclic 6-membered ring, preferably a substituted heterocyclic 5-membered ring.

[0053] In a preferred embodiment of the present invention, R 13 and R 14 , and / or R 15 and R 16 each 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 monocyclic 6-membered ring.

[0054] In a preferred embodiment of the present invention, R 13 and R 14 , and / or R 15 and R 16 each form an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O, and N.

[0055] In a preferred embodiment of the present invention, the compound of the present invention does not have a ring structure between R 13 and R 14 , and / or between R 15 and R 16 .

[0056] In a developed form of the present invention, it is as follows: R 14 and R 16 are

Chemical formula

[0057] In a preferred embodiment of the present invention, R 17 and / or R 18 is H, preferably R 17 and R 18 is.

[0058] In a preferred embodiment of the present invention, at least R 31 and R 35 is H.

[0059] In a preferred embodiment of the present invention, R 31 R 32 R 34 and R 35 is H.

[0060] In a more preferred embodiment, R 31 ~R 35 is H.

[0061] In a development form of the present invention, it is as follows: 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, provided that at least R 1 or R 2 is Br, Cl, or CF3, preferably Br or Cl.

[0062] In a development form of the present invention, it is as follows: Y1 and Y3 are CH, and Y2 is CR 22and preferably CR 22 is selected from the group consisting of F, Br, Cl and CN, or Y1 is CR 21 where Y2 is N and Y3 is CR 23 and preferably where CR 21 and CR 23 are H or methyl, or Y1 is N, Y2 is CR 22 and Y3 is N, preferably where CR 22 is H or methyl.

[0063] In a preferred embodiment of the present invention, R 1 and R 2 are each F or Cl.

[0064] In one development form of the present invention, it is as follows: at least one chemical compound is a compound of general formula III

Chemical formula

[0065] In one development form of the present invention, it is as follows: at least one chemical compound is a compound of general formula IV

Chemical formula

[0066] In one development form of the present invention, it is as follows: At least one chemical compound is a compound of general formula V [Chemical formula] (wherein X1 and X2 are independently O or S, where R 42 is H, F, Cl, CF3 or C1-C4-alkyl, and where Hal is Br, Cl or F) is.

[0067] In a preferred embodiment of the present invention, at least one chemical compound is a compound of general formula III, a compound of general formula VI, and a compound of general formula III.

[0068] In one development form of the present invention, it is as follows: R 14 and R 16 are each 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, where preferably, R 19 , R 17 and R 19 , or R 18 and R 19 are a substituted or unsubstituted or halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered ring, where preferably, R 32 , R 33 , or R 32 and R 34 are substituted, or R 31 ~R 35 is H.

[0069] In one development form of the present invention, the compound is as follows: [Chemical formula] [Chemical formula]

Chem.

Chem.

[0070] In a preferred embodiment of the present invention, the compound is in a mirror-symmetric form about the axis passing through B, and a meso position is formed.

[0071] General syntheses related to the preparation of the compounds of the present invention having a BODIPY basic skeleton and a 4-pyridyl meso group are known from Non-Patent Document 1 (Bartellmess et al. (“meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties”, New Journal of Chemistry, 37(9), 2663-2668; 2013)).

[0072] The compounds of the present invention relate particularly to "small molecules". In particular, a small molecule means a non-polymeric organic molecule having a monodisperse molar mass of 100 to 2000 g / mol, which is in the solid phase at standard pressure (the atmospheric pressure of the ambient atmosphere) and room temperature. In particular, the small molecule is photoactive, and "photoactive" means that the molecule changes its charge state and / or polarization state when exposed to light. A specific feature of a photoactive molecule is the absorption of electromagnetic waves within a defined wavelength range, which is accompanied by the conversion of the absorbed electromagnetic waves, i.e., photons, into excitons.

[0073] In one development form of the present invention, it is as follows: The optoelectronic component is an organic optoelectronic component, preferably an organic photovoltaic device, OFET, OLED or organic photodetector, particularly preferably an organic photovoltaic device.

[0074] In a preferred embodiment of the present invention, at least one photoactive layer is an absorber layer; preferably, at least one compound is an absorbing material.

[0075] At least one photoactive layer in the form of a planar heterojunction (PHJ) has a donor layer having at least one compound of the present invention as a donor, and an acceptor layer disposed thereon, preferably disposed directly thereon and having at least one acceptor; preferably, the acceptor is a fullerene, particularly preferably C60, or a fullerene derivative. Alternatively, the acceptor may be a non-fullerene acceptor (NFA).

[0076] 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 containing at least one compound of the present invention as an acceptor.

[0077] In a preferred embodiment of the present 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.

[0078] In a preferred embodiment of the present 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.

[0079] In a preferred embodiment of the present 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.

[0080] In a preferred embodiment of the present invention, the compound and / or the layer having at least one compound is deposited by vapor deposition or solvent treatment, more preferably by vacuum treatment.

[0081] The object of the present invention is also achieved by providing the use of at least one compound of the present invention in the photoactive layer in the form of a planar heterojunction (PHJ) in optoelectronic components, preferably organic optoelectronic components, particularly those according to one of the above embodiments. The use of at least one compound in optoelectronic components brings about the advantages already elucidated in connection with the optoelectronic components of the present invention comprising at least one compound.

[0082] In one development of the present invention, it is as follows: The compounds of the present invention are used in organic optoelectronic components, preferably organic photovoltaic devices, OLEDs, OFETs, or organic photodetectors.

[0083] In a preferred embodiment of the present invention, at least one compound of the present invention is used in the photoactive layer of an optoelectronic component as an absorption material. In a preferred embodiment of the present invention, the compounds of the present invention are used as donors in donor-acceptor heterojunctions.

[0084] In a preferred embodiment of the present invention, the optoelectronic component comprises a substrate, where the first electrode or the second electrode is disposed on the substrate; in particular, one of the electrodes of the optoelectronic component may be applied directly to the substrate, where the layer system is disposed between the first electrode and the second electrode.

[0085] The object of the present invention is also a chemical compound of general formula II, particularly according to one of the above embodiments [Chemical formula] (wherein Y1 is selected from the group consisting of N and CR 21 and R 21 is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF3; Y2 is selected from the group consisting of N and CR 22 and R 22is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF3; Y3 is selected from the group consisting of N and CR 23 wherein R 23 is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF3; Z1 and Z2 are F or CF3; X1 and X2 are independently O, S or N-R 8 wherein R 8 is selected from the group consisting of H, alkyl and aryl, wherein preferably X1 and X2 are S, or X1 and X2 are O; R 1 and R 2 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, provided that at least R 1 or R 2 is Br, Cl, CF3, CHF2, CH2F or CH3; R 13 and R 15 are independently selected from the group consisting of H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C1-C4-alkyl; R 14 and R 16 are preferably independently selected from unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted heterocyclic 5-membered or 6-membered rings, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered rings having a heteroatom preferably independently selected from S, O and N, preferably from the group consisting of unsubstituted and substituted heterocyclic 5-membered rings, and unsubstituted and substituted monocyclic 6-membered rings) This is achieved by providing. For the chemical compounds of general formula II, this brings in particular the advantages already elucidated in connection with the optoelectronic components of the present invention.

[0086] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 14 and R 16 are substituted heterocyclic 5-membered rings, where at least one hydrogen atom, preferably one hydrogen atom, in the heterocyclic 5-membered ring is 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, R 14 and / or R 16 has no further condensation.

[0087] In a preferred embodiment of the present invention, in the chemical compound of general formula II, X1 and X2 are S or X1 and X2 are O; particularly preferably, X1 and X2 are O.

[0088] In a preferred embodiment of the present invention, in the chemical compound of general formula II, in R14 and R16, at least one hydrogen atom of the monocyclic 6-membered ring and / or at least one hydrogen atom of the heterocyclic 5-membered ring or 6-membered ring is substituted by F or CF3, preferably F.

[0089] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 13 and R 15 are H.

[0090] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 13 and R 15 are the same, and / or R 14 and R 16 are the same.

[0091] In a preferred embodiment of the present invention, in the chemical compound of general formula II, Z1 is the same as Z2, and R 13 is R15 is identical to, and, R 14 is R 16 is identical to.

[0092] In a preferred embodiment of the present invention, in the chemical compound of general formula II, X1 and X2 are O or S, R 13 and R 15 are H, and, R 14 and R 16 is preferably an unsubstituted or substituted heterocyclic 5-membered or 6-membered ring having a heteroatom selected from S, O and N, or an unsubstituted or substituted carbocyclic 6-membered ring, preferably a substituted heterocyclic 5-membered ring.

[0093] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 13 and R 14 , and / or, R 15 and R 16 forms, in each case, 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 carbocyclic 6-membered ring.

[0094] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 13 and R 14 , and / or, R 15 and R 16 forms, in each case, an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N.

[0095] In a preferred embodiment of the present invention, the chemical compound of general formula II does not have a ring structure between R 13 and R 14 , and / or, between R 15 and R 16 .

[0096] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 14 and R 16 are [Chemical formula] (wherein, X3 is O, S or N-R 9 and R 9 is selected from the group consisting of H, alkyl and aryl; R 17 ~R 19 and R 31 ~R 35 and R are independently selected from the group consisting of.

[0097] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 17 and / or R 18 is H, preferably R 17 and R 18 are.

[0098] In a preferred embodiment of the present invention, in the chemical compound of general formula II, at least R 31 and R 35 is H.

[0099] In a preferred embodiment of the present invention, in the chemical compound of general formula II, R 31 R 32 R 34 and R 35 are H.

[0100] In a more preferred embodiment of the present invention, in the chemical compound of general formula II, R 31 ~R 35 is H.

[0101] In a more preferred embodiment of the present invention, in the chemical compound of general formula II, Z1 and Z2 are F, and R 1 and R2 is independently selected from the group consisting of H, F, Cl, and Br, provided that at least R 1 or R 2 is Br or Cl.

[0102] In a further preferred embodiment of the present invention, in the chemical compound of general formula II, Y1 and Y3 are CH, and Y2 is CR 22 wherein preferably CR 22 is selected from the group consisting of F, Br, Cl, and CN, or Y1 is CR 21 where Y2 is N, and Y3 is CR 23 wherein preferably CR 21 and CR 23 are H or methyl, or Y1 is N, Y2 is CR 22 where Y3 is N, preferably CR 22 is H or methyl, where R 1 and R 2 are, in each case, preferably F or Cl.

[0103] In a further preferred embodiment of the present invention, at least one chemical compound is a compound of general formula III

Chemical formula

[0104] In a further preferred embodiment of the present invention, at least one chemical compound is a compound of general formula IV

Chemical formula

[0105] In a further preferred embodiment of the present invention, at least one chemical compound is a compound of general formula V

Chemical formula

[0106] In a further preferred embodiment of the present invention, in the chemical compound of general formula II, R 14 and R 16 is an unsubstituted or substituted heterocyclic 5-membered ring having at least one heteroatom selected from S, O and N, preferably O and S, where preferably R 19 , R 17 and R 19 , or R 18 and R 19 is a substituted or unsubstituted or substituted monocyclic 6-membered ring, where preferably R 32 , R 33 , or R 32 and R 34 is substituted, or R 31 ~R 35 is H.

[0107] Hereinafter, the present invention will be described in detail with reference to the drawings. The drawings are as follows.

Brief description of the drawings

[0108]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Mode for Carrying Out the Invention

[0109]

Examples

[0110] Figure 1 shows a schematic cross-sectional view of an example of the optoelectronic component 10.

[0111] In this example, the optoelectronic component 10 is an organic photovoltaic device.

[0112] The optoelectronic component 10 has a substrate 1. On the substrate 1, a layer system 7 including a base electrode 2, a cover electrode 6, and at least one photoactive layer 4 is disposed, and the layer system 7 is disposed between the base electrode 2 and the cover electrode 6. At least one photoactive layer 4 is in 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 chemical compound of general formula I as a donor. In this example, the acceptor layer of the photoactive layer 4 has fullerene C60 as an acceptor; however, the acceptor may alternatively be a fullerene derivative or a non-fullerene acceptor (NFA). The chemical compound of general formula I has the following structure:

Chemical formula

[0113] The general preparation of the compounds of the invention is known to the person skilled in the art from the prior art. In this context, reference is made in particular to Patent Document 4 (International Publication No. WO 2007 / 126052 A1 pamphlet) and Patent Document 5 (European Patent Application Publication No. EP 3617214 A1).

[0114] In one configuration of the invention, the optoelectronic component 10 has a layer system 7 having at least one light-absorbing photoactive layer 4, where the at least one light-absorbing photoactive layer 4 contains at least one compound of general formula I.

[0115] 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 tandem cell, triple cell or multi-cell.

[0116] In one embodiment, the organic optoelectronic device has a glass substrate 1, which may be formed of, for example, a PET film. On the substrate 1, a base electrode 2 made of, for example, ITO is provided. On top of that, a layer system 7 is arranged having an electron transport layer 3 (ETL) and a photoactive layer 4 in the form of a planar heterojunction having at least one compound of the present invention as a donor material and an acceptor material such as fullerene C60. On top of the latter, a p-doped hole transport layer 5 (HTL) and an upper electrode 6 made of gold or aluminum are arranged.

[0117] In one configuration of the present invention, an optoelectronic component 10 containing a compound of general formula I in a photoactive layer 4 in the form of a planar heterojunction is an organic optoelectronic component, preferably an organic optoelectronic device, OFET, OLED or organic photodetector.

[0118] The organic materials are applied to the foil in the form of thin films or small volumes by printing, bonding, coating, evaporation, or other methods. Useful methods for the production of thin layers are likewise those used in electronics on glass, ceramic or semiconductor carriers. Vacuum evaporation was used for the production of the layer system in this example.

[0119] Figure 2 shows a schematic diagram of an example of a synthesis scheme for the synthesis of the compound of the present invention.

[0120] The experimental procedure for the synthesis of the compound of general formula I is shown in Figure 2.

[0121] Basic procedure for step 2-A: Aldehyde A (1.00 equivalent) was dissolved / suspended in 9 vol of absolute ethanol. Ethyl trifluoroacetate (1.50 equivalents) was added and the resulting mixture was cooled to 0 °C. Then, sodium ethoxide solution (21 wt%, 1.50 equivalents) was added and after 5 minutes, ethyl 2-azidoacetate (1.50 equivalents) was slowly added within 10 minutes at a temperature below 5 °C. The mixture was then stirred at 0 °C for 30 minutes and slowly warmed to room temperature while stirring was continued for 4 hours. The reaction mixture was dissolved in 21 vol of ethanol, the precipitate was filtered off and washed with cooled absolute ethanol to obtain Intermediate B.

[0122] Basic procedure according to Step 2-B: Intermediate B was dissolved in toluene, the resulting solution was dried over anhydrous sodium sulfate and filtered. 43 vol of anhydrous toluene was charged into a flask under an argon atmosphere and heated under reflux. The solution of Intermediate B was introduced into a dropping funnel and slowly added to the toluene within 15 minutes while heating under reflux. The resulting solution was heated for a further 15 minutes. The solvent was removed under reduced pressure to obtain a brown solid as the crude product. The crude product was suspended in 8 vol of petroleum ether and treated with ultrasound. The resulting precipitate was filtered off, washed with petroleum ether and dried under reduced pressure to obtain pyrrole ester C.

[0123] Basic procedure according to Step 3-A: Pyrrole ester C (1.00 equivalent) was suspended in 19 vol of ethanol and a solution of 5.0 equivalents of NaOH in 4 vol of water was added. The mixture was stirred at 75 °C for 1 hour and then 7.0 equivalents of AcOH in 11 vol of water was added to achieve a pH of approximately 4. The product was filtered off and washed with water and then toluene to obtain pyrrole acid D.

[0124] Basic procedure according to Step 3-B: Pyrrole acid D (1.00 equivalent) was dissolved in 21 vol of ethanolamine. The mixture was heated to 150 °C and stirred for 4 hours. After cooling to 50 °C, 32 vol of 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 obtain pyrrole E.

[0125] Basic procedure according to Step 4: Pyrrole E (2.00 equivalents) and aldehyde (1.00 equivalent) were dissolved / suspended in 30 vol of dichloromethane. Trifluoroacetic acid (0.10 equivalent) was added dropwise at room temperature, and the mixture was stirred for 3 hours. p-Chloranil (1.05 equivalents) was added dropwise over 5 minutes, and the mixture was mixed at room temperature for 30 minutes. The mixture was diluted with 25 vol of methanol and then concentrated under reduced pressure (40 °C in a water bath) to remove most of the dichloromethane. Then, the resulting suspension was stirred at 0 °C for 90 minutes and then filtered. The isolated solid was washed with cold methanol and dried under reduced pressure to obtain dipyrin F.

[0126] Basic procedure (synthesis) according to Step 5: Dipyrin F (1.00 equivalent) was suspended in 42 vol of anhydrous toluene. The mixture was stirred at 55 °C, and N,N-diisopropylethylamine (1.50 equivalents) was added. A solution of boron trifluoride diethyl etherate (4.00 equivalents) in 10 vol of anhydrous toluene was slowly added. The mixture was stirred at 55 °C until dissolution was complete. The reaction mixture was cooled to 0 °C and stirred at that temperature for 1 hour. The precipitate was filtered off, washed with toluene and methanol, and then dried under reduced pressure to obtain crude BODIPY G. The crude BODIPY G was purified by recrystallization to obtain purified BODIPY G.

[0127] Synthesis of compounds: Synthesis of 5-phenylfuran-2-carbaldehyde A-1 [Chemical formula] The synthesis of 5-phenylfuran-2-carbaldehyde A-1 can be carried out according to Non-Patent Document 2 (Li et al. (J. Am. Chem. Soc. 2017, 139(39), 13636-13639)).

[0128] Synthesis of pyrrole ester C-1

Chemical formula

[0129] Synthesis of pyrrole acid D-1

Chemical formula

[0130] Synthesis of pyrrole E-1

Chemical formula

[0131] Synthesis of Dipyrin F-1

Chem.

[0132] Synthesis of BODIPY G-1

Chem.

[0133] Figure 3 shows the current-voltage curve graph, spectral external quantum efficiency, and fill factor of the PHJ cell containing compound (40) measured with the organic optoelectronic component 10. The same reference numerals are given to equivalent and functionally equivalent elements, and for this point, refer to the above description. In this example, the optoelectronic component 10 is an organic photovoltaic device.

[0134] To examine the compound, i.e., its use as an absorption material in the organic optoelectronic component 10, the current-voltage curve of the PHJ cell was measured (Figure 3A), and the external quantum efficiency with respect to wavelength was plotted (Figure 3B). The current-voltage curve includes indicators characterizing the organic photovoltaic device. Here, the most important indicators are the fill factor FF, open-circuit voltage U oc , and short-circuit current Jsc.

[0135] Structure: The current-voltage curve of a PHJ cell having glass + 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) was measured. The cell parameters were measured under AM1.5 illumination (AM = air mass; AM = 1.5; in this spectrum, the total solar irradiance is 1000 W / m 2 ; as a standard value for the analysis of solar modules, AM = 1.5), where the photoactive layer contains a planar heterojunction (PHJ). In the photoactive layer 4, the donor layer of Compound (40) was applied separately from the acceptor layer of C60 in the form of a planar heterojunction. Here, ITO functions as the base electrode 2, the adjacent fullerene C60 functions as the electron transport layer (ETL) 3, adjacent to which is a photoactive layer 4 having an acceptor layer and a donor layer disposed on the electron transport layer 3, followed by NHT169 as the hole transport layer (HTL) 5 and NDP9-doped NHT169. The top electrode is made of gold. NDP9 is a commercially available p-dopant from Novaled GmbH. NHT169 is an HTL matrix material from Novaled GmbH.

[0136] The individual layers of the optoelectronic component 10, in particular the photoactive layer 4, can be applied by evaporating the corresponding materials under reduced pressure. Compound (40) exhibits good evaporability under reduced pressure.

[0137] In an optoelectronic component containing Compound (40) in a planar heterojunction, the fill factor FF is 73.1%, the open circuit voltage U oc is 0.99 V, and the short circuit current Jsc is 11.2 mA / cm 2 . The EQE max of such an organic photovoltaic device is 84%.

[0138] Figure 4 shows a graph of the absorption spectrum of Compound (40). Equivalent and functionally equivalent elements are denoted by the same reference signs; for this, refer to the above description.

[0139] The structure of the optoelectronic component 10 corresponds to that of FIG. 2; the donor in the photoactive layer 4 in the form of a planar heterojunction is likewise the compound (40).

[0140] The absorption maximum λmax of the compound (40) is 743 nm.

[0141] FIG. 5 shows the maximum external quantum efficiency (EQEmax) of a plurality of Examples 10 of the compound of the present invention in an optoelectronic component. The same reference numerals are given to equivalent and functionally equivalent elements; for this, reference is made to the above description. In this example, the optoelectronic component 10 is an organic photovoltaic device.

[0142] The structure of the optoelectronic component 10 corresponds to that of FIG. 2, and in each case, the donor in the photoactive layer 4 in the form of a planar heterojunction is different.

[0143] The following donors derived from the compound of general formula I of the present invention were used.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0144] Table 1 shows the absorption maximum λmax of a plurality of compounds of the present invention in a film. The optical properties were determined experimentally. The absorption maximum λmax was determined from a 30 nm thick vacuum deposited layer on quartz glass using a photometer. Table 1 shows the photovoltaic parameters Uoc, Jsc and FF of a plurality of compounds of the present invention, together with their respective EQE max along with. The maximum EQE is denoted as EQE max and is an important parameter for explaining the efficiency of a photovoltaic device. The EQE in the corresponding spectral region maxThe higher it is, the higher the efficiency of the photo - electric power generation element. The EQE of the compound of the present invention max is in the range of 60% to 84%.

[0145]

Table 1

[0146] EQE according to a specific example of the chemical compound of general formula I of the present invention in the PHJ cell of the organic photo - electric power generation element max is outlined in accordance with the meso - group and side - groups (corresponding to R in the compound having general formula III) on the BODIPY basic skeleton, as outlined in FIG. 5. The corresponding compound numbers are shown in parentheses for each case. The PHJ cell containing the compound of the present invention shows a particularly high EQE 14 / R 16 compared with compounds that are not of the present invention, especially BODIPY compounds that do not have the structural features of the present invention at the meso - position. max is shown.

[0147] The experimental data of the compound of the present invention in the photoactive layer 4, which is in the form of a planar heterojunction in the organic photo - electric power generation element, demonstrate that the compound of the present invention has very good compatibility as an absorption material in the planar heterojunction and brings about improved efficiency of the photo - electric power generation element having such a photoactive layer 4.

Claims

1. An optoelectronic component, preferably a photovoltaic device, having a layer system comprising a base electrode, a top electrode and at least one photoactive layer, said layer system being disposed between said base electrode and said top electrode, and at least one photoactive layer being in the form of a planar heterojunction (PHJ), and said at least one photoactive layer in the form of a planar heterojunction comprising at least one chemical compound of general formula I 【Chemical 1】 (wherein, Y １ is selected from the group consisting of N and CR ２１ and, where R ２１ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN, CF ３ or SF ５ ; Y ２ is selected from the group consisting of N and CR ２２ wherein, R ２２ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN, CF ３ or SF ５ ; Y ３ is selected from the group consisting of N and CR ２３ wherein R ２３ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN, CF ３ or SF ５ ; Z １ and Z ２ are independently selected from the group consisting of F, Cl, CN, CF ３ , C ２ F ５ , OCH ３ and OC ２ H ５ ; and are independently selected from the group consisting of R １ and R ２ are independently selected from the group consisting of H, F, Cl, Br, CN, CF ３ , CHF ２ , CH ２ F, C １ ~C ４ -alkyl, O-C １ ~C ４ -alkyl, S-C １ ~C ４ -alkyl and N-(C １ ~C ４ -alkyl), provided that at least R ２ or R １ is Br, Cl, CF ２ , CHF ３ , CH ２ F or CH ２ F and CH ３ ; R ３ and R ５ 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, unsubstituted and alkyl-substituted heterocyclic 5-membered and 6-membered rings having at least one heteroatom selected from S, O or N, and unsubstituted and alkyl-substituted monocyclic 6-membered rings, wherein the unsubstituted or substituted heterocyclic 5-membered or 6-membered ring, or the unsubstituted or substituted monocyclic 6-membered ring may be fused to a further unsubstituted or substituted heterocyclic 5-membered or 6-membered ring; R ４ and R ６ are independently selected from the group consisting of H, halogen, CN, alkyl, alkenyl, O-alkyl, S-alkyl, unsubstituted and halogen-, alkyl- and / or O-alkyl-substituted heterocyclic 5-membered 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 monocyclic 6-membered rings; or R ３ and R ４ and / or R ５ and R ６ in each case together form an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted heterocyclic 5- or 6-membered ring having at least one heteroatom preferably selected from S, O and N, or an unsubstituted or halogen-, alkyl-, O-alkyl-, aryl- and / or heteroaryl-substituted homocyclic 6-membered ring) An optoelectronic component comprising:

2. Z １ and Z ２ is F; and / or R １ and R ２ are independently selected from the group consisting of H, F, Cl, Br, CN, CF ３ , Me, Et, OMe, SMe, OEt, SEt, Pr and iPr, provided that at least R １ or R ２ is Br or Cl, where preferably R １ and R ２ are not H; or R １ and R ２ are each independently selected from the group consisting of Cl, Br, CF ３ , CN, Me, Et, OMe, SMe, OEt and SEt, provided that at least one of R １ or R ２ is Cl, Br, CF ３ or Me; or R １ and R ２ are selected from the group consisting of Br, Cl, CF ３ , CHF ２ and CH ２ F, the optoelectronic component according to claim 1.

3. Y １ is selected from the group consisting of N and CR ２１ wherein R ２１ is H or Cl, and / or Y ２ is selected from the group consisting of N and CR ２２ , where R ２２ is H, CH ３ , O-CH ３ , S-CH ３ , F, Cl, CF ３ or SF ５ , preferably N or CH, and / or Y ３ is selected from the group consisting of N and CR ２３ , where R ２３ is H or Cl; Here, preferably, one Y １ , Y ２ , Y ３ is N, or two Ys １ , Y ２ , Y ３ are N, the optoelectronic component according to claim 1 or claim 2.

4. R ３ and R ４ and / or, R ５ and R ６ is an unsubstituted or substituted heterocyclic 5- or 6-membered ring having at least one heteroatom selected from O, S and N, preferably O and S, or forms an unsubstituted or substituted monocyclic 6-membered ring, or R3 and R4, and / or, R ５ and R ６ is an unsubstituted or substituted heterocyclic 5-membered ring, preferably a substituted heterocyclic 5-membered ring having at least one heteroatom selected from O, S and N, preferably O and S, or forms an unsubstituted or substituted monocyclic 6-membered ring, preferably an unsubstituted monocyclic 6-membered ring, the optoelectronic component according to claim 1.

5. Said at least one chemical compound is a compound of general formula II [Chemical 2] (wherein, Y １ is selected from the group consisting of N and CR ２１ and, wherein, R ２１ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Y ２ is selected from the group consisting of N and CR ２２ wherein R ２２ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Y ３ is selected from the group consisting of N and CR ２３ wherein R ２３ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Z １ and Z ２ is F or CF ３ ; X １ and X ２ each independently is O, S or N—R ８ wherein R ８ is selected from the group consisting of H, alkyl and aryl Preferably, X １ and X ２ is S, or X １ and X ２ is O; R １ and R ２ are independently selected from the group consisting of H, F, Cl, Br, CN, CF ３ , CHF ２ , CH ２ F, C １ ~C ４ -alkyl, O-C １ ~C ４ -alkyl, S-C １ ~C ４ -alkyl and N-(C １ ~C ４ -alkyl), provided that at least R ２ or R １ is Br, Cl, CF ２ , CH ３ F, CHF ２ or CH ２ is; ３ and; R １３ and R １５ are independently selected from the group consisting of H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C １ ~C ４ -alkyl; R １４ and R １６ is preferably selected independently 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 having a heteroatom selected independently from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered rings, preferably selected independently from the group consisting of unsubstituted and substituted heterocyclic 5-membered rings, and unsubstituted and substituted monocyclic 6-membered rings) The optoelectronic component according to claim 1, wherein:

6. R １４ and R １６ are [Chemical 3] (wherein, X ３ is O, S or N-R ９ and R ９ is selected from the group consisting of H, alkyl and aryl; R １７ ~R １９ and R ３１ ~R ３５ are independently selected from the group consisting of H, halogen (preferably F and Cl), CN, alkyl (preferably C １ ~C ４ -alkyl), O-alkyl (preferably O-C １ ~C ４ -alkyl), and S-alkyl (preferably S-C １ ~C ４ -alkyl), where preferably at least one hydrogen atom is substituted with F) The optoelectronic component according to claim 5, which is independently selected from the group consisting of:

7. Z １ and Z ２ is F, and R １ and R ２ are independently selected from the group consisting of H, F, Cl, Br, CH ３ , CH ２ F, CHF ２ and CF ３ , provided that at least R １ or R ２ is Br, Cl or CF ３ The optoelectronic component according to claim 5 or claim 6

8. Y １ and Y ３ is CH, and Y ２ is CR ２２ and preferably CR ２２ is selected from F, Br, Cl and CN, or Y １ is CR ２１ and Y ２ is N, and Y ３ is CR ２３ and preferably CR ２１ and CR ２３ is H or methyl, or Y １ is N, and Y ２ is CR ２２ and Y ３ is N, and preferably CR ２２ is H or methyl, the optoelectronic component according to claim 1.

9. Said at least one chemical compound is a compound of general formula III 【Chemical Formula 4】 (wherein, X １ and X ２ are independently O or S, R ４０ is H, Cl or F, preferably H, and Hal is Br, Cl or F) The optoelectronic component according to claim 1, wherein:

10. Said at least one chemical compound is a compound of general formula IV 【Chemical Formula 5】 (wherein X １ and X ２ are independently O or S, where R ４１ is H, F, Cl, Br, CF ３ or C １ to C ４ -alkyl, preferably H or Cl, and where Hal is Br, Cl or F) The optoelectronic component according to claim 1, wherein:

11. Said at least one chemical compound is a compound of general formula V 【Chemical Formula 6】 (wherein, X １ and X ２ are each independently O or S, where R ４２ is H, F, Cl, CF ３ or C １ to C ４ -alkyl, and wherein Hal is Br, Cl or F) The optoelectronic component according to claim 1, wherein:

12. R １４ and R １６ are each, 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, R １９ , or, R １７ and R １９ , or, R １８ and R １９ are a substituted or unsubstituted or halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered ring, wherein preferably, R ３２ , R ３３ , or, R ３２ and R ３４ are substituted or, preferably, R ３１ to R ３５ is H, the optoelectronic component according to claim 1.

13. Said compound is: 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical Formula 10】 The optoelectronic component according to claim 1, which is selected from the group consisting of:

14. Use of at least one compound according to claim 1 in a photoactive layer in the form of a planar heterojunction (PHJ) in an optoelectronic component, preferably an organic optoelectronic component, said organic optoelectronic component preferably being an organic photovoltaic device, an OLED, an OFET or an organic photodetector.

15. A chemical compound of general formula II 【Chemical 11】 (wherein, Y １ is selected from the group consisting of N and CR ２１ and, wherein R ２１ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Y ２ is selected from the group consisting of N and CR ２２ wherein R ２２ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Y ３ is selected from the group consisting of N and CR ２３ wherein R ２３ is H, alkyl, O-alkyl, S-alkyl, preferably a halogen such as F or Cl, CN or CF ３ ; Z １ and Z ２ is F or CF ３ ; X １ and X ２ each independently is O, S or N—R ８ wherein R ８ is selected from the group consisting of H, alkyl and aryl, and preferably X １ and X ２ is S, or X １ and X ２ is O; R １ and R ２ are independently selected from the group consisting of H, F, Cl, Br, CN, CF ３ , CHF ２ , CH ２ F, C １ ~C ４ -alkyl, O-C １ ~C ４ -alkyl, S-C １ ~C ４ -alkyl and N-(C １ ~C ４ -alkyl), provided that at least R ２ or R １ is Br, Cl, CF ２ , CHF ３ , CH ２ F or CH ２ F or CH ３ ; R １３ and R １５ are each independently selected from the group consisting of H, halogen, CN, alkyl, O-alkyl and S-alkyl, preferably H or C １ ~C ４ -alkyl; R １４ and R １６ is preferably selected independently 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 having a heteroatom selected independently from S, O and N, and unsubstituted and halogen-, alkyl-, fluorinated alkyl-, O-alkyl- and / or fluorinated O-alkyl-substituted monocyclic 6-membered rings, preferably selected independently from the group consisting of unsubstituted and substituted heterocyclic 5-membered rings, and unsubstituted and substituted monocyclic 6-membered rings).

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