Solar cell containing an adamantane- and / or diadamantane-based passivation layer
The adamantane-based passivation layer addresses the scalability and recombination issues in perovskite solar cells by reducing non-radiative recombination at interfaces, enhancing solar cell efficiency through vacuum deposition.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- KARLSRUHER INST FUR TECH
- Filing Date
- 2025-10-20
- Publication Date
- 2026-04-30
AI Technical Summary
Existing passivation layers for perovskite-based solar cells are not scalable without negatively impacting underlying layers, and there is a need for materials that reduce recombination losses at the interfaces between the absorber and charge transport layers.
A passivation layer based on adamantane and/or diamond compounds applied via vacuum deposition, which separates charge carriers at the interface to reduce non-radiative recombination.
The adamantane-based passivation layer effectively reduces recombination losses, enabling scalable application without affecting the underlying absorber layer, thereby improving solar cell performance.
Smart Images

Figure IMGF000005_0001 
Figure IMGF000006_0001 
Figure IMGF000024_0001
Abstract
Description
[0001] Solar cell containing an adamantane and / or a diadamantane-based passivation layer
[0002] TECHNICAL AREA
[0003] The present invention relates to a solar cell, a method for its manufacture and a solar cell obtainable by this method.
[0004] INTRODUCTION
[0005] DE 102009025977 A1 relates to a solar cell and a manufacturing process for a solar cell, wherein the solar cell comprises a semiconductor layer and a passivation layer arranged on a surface of the semiconductor layer for passivating the semiconductor layer surface, wherein the passivation layer comprises a chemically passivating passivation sublayer and a field-effect passivating passivation sublayer, which are arranged one above the other on the semiconductor layer surface.
[0006] US 2011 / 0284068 A1 relates to a method and structure for achieving extremely low surface recombination rates through highly efficient surface passivation in crystalline silicon solar cells using a two-layer passivation scheme that also functions as efficient ARC. The two-layer passivation consists of a first thin layer of wet-chemically deposited oxide or a thin layer of hydrogenated amorphous silicon. A second layer of amorphous hydrogenated silicon nitride is deposited onto the wet-chemical oxide or the amorphous silicon layer. After this deposition, an annealing process is performed to further improve the surface passivation. Yen-Hung Lin et al., “Bandgap-universal passivation enables stable perovskite solar cells with low photovoltage loss”, Science, 384, 767-775 (2024) concerns an amino-silane-based passivation layer deposited from the gas phase for metal halide perovskite solar cells.
[0007] Zhengchi Yang et al., "Self-healing and efficient flexible perovskite solar cells enabled by hostguest interaction and a 2S / 3S heterostructure", Journal of Materials Chemistry A: Materials for Energy and Sustainability, 10(42), 22445 (2022) concerns the incorporation of a self-healing terpolymer based on a host-guest interaction in a 2D / 3D heterostructure perovskite layer.
[0008] Mohammad Mahdi Tavakoli et al., “Adamantanes Enhance the Photovoltaic Performance and Operational Stability of Perovskite Solar Cells by Effective Mitigation of Interfacial Defect States”, Advanced Energy Materials, 8(19), 1800275 (2018) concerns the incorporation of adamantane (AD) and 1-adamantylamine (ADA) into perovskite solar cells applied using antisolvent or spin-coating methods.
[0009] Li Tan et al., “Quantitative Surface Passivation Through Drop-on-Demand Inkjet Printing Enables Highly Efficient Perovskite Solar Cells,” Advanced Energy Materials, 14(27), 2400549 (2024) concerns the drop-on-demand inkjet printing of 2-adamantylamine hydrochloride (2-ADAHCI).
[0010] Qian Zhou et al., “Revealing Steric-Hidrance-Dependent Buried Interface Defect Passivation Mechanism in Efficient and Stable Perovskite Solar Cells with Mitigated Tensile Stress”, Advanced Functional Materials, 32(36), 2205507 (2022) concerns adamantane-based passivators - in particular 2-adamantanone (AD), 1-adamantanecarboxylic acid (ADCA) and 1-adamantaneacetic acid (ADAA) - for modifying the SnQ2 / perovskite interface.
[0011] Jose M. Obrero-Perez et al., “Ultrathin Plasma Polymer Passiavation of Perovskite Solar Cells for Improved Stability and Reproducibility”, Advanced Energy Materials, 12(32), 2200812 (2022) concerns adamantane-containing passivation layers applied using Remote Plasma-Assisted Vacuum Deposition (RPAVD).
[0012] Although passivation layers already exist for silicon-based solar cells, the need for a passivation layer, especially for perovskite-based solar cells, remains. Furthermore, the passivation layers and materials for silicon and perovskite-based solar cells differ fundamentally in their functionality, material composition, layer thickness, etc. A particular challenge with perovskite-based solar cells is applying the passivation layer in a scalable manner without negatively impacting the underlying layers.
[0013] DETAILED DESCRIPTION
[0014] Therefore, an objective of the present invention was to provide a passivation layer for solar cells that reduces recombination losses at the interfaces between the absorber layer and the charge transport layer. The non-radiative recombination of charge carriers between the electron transport layer and the perovskite absorber limits the achievable power output of the device. Without adhering to a specific theory, TPA is an organic insulator that separates charge carriers at the interface, thereby reducing non-radiative recombination. A particular advantage is that TPA is the first adamantane-based material that can be successfully used as a passivation layer in a solar cell via vacuum deposition. Furthermore, an objective of the present invention was to produce solar cells with a passivation layer in a simple and cost-effective manner.Furthermore, an objective of the present invention was to establish a scalable application method that does not negatively affect the underlying absorber layer. In particular, solvent-based application can partially dissolve the perovskite absorber layer.
[0015] This task is solved by a solar cell comprising a passivation layer based on adamantane and / or diamond compounds and a method for its manufacture.
[0016] The present invention relates to a solar cell, wherein the solar cell is a single solar cell or a subcell of a multi-junction solar cell, comprising the solar cell
[0017] an absorber layer, one or more passivation layers, an electron transport layer conductively connected to at least one negative electrode of the solar cell, a hole transport layer conductively connected to at least one positive electrode of the solar cell; wherein the one or more passivation layers are a compound of formula (A)
[0018]
[0019] include;
[0020] wobei R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind;
[0021] wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Sauerstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1, -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1 , alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable; and / or wherein one or more passivation layers are a compound of formula (B)
[0022]
[0023] include;
[0024] where RT, R2', R3', and R4' are independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylheteroalkyl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkylalkyl, heterocycloalkylheteroalkyl, aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl,
[0025] Haloalkyl, haloalkenyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkenyloxy, alkynyloxy, cycloalkylkoxy, heterocycloalkyloxy, aryloxy, arylalkyloxy, phenoxy, benzyloxy, heteroaryloxy, amino, alkylamino, aminoalkyl, acylamino, arylamino, sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1 , alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected;
[0026] wherein R9', R10', R11', R12', R13' and R14' independently of each other from the group consisting of hydrogen, oxygen, halogen, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylheteroalkyl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkylalkyl, heterocycloalkylheteroalkyl,
[0027] Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1The groupings selected are alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of which may be substituted. According to the present invention, the terms "hole transport layer" and "electron transport layer" generally denote any charge transport layers that enable the selective extraction of the corresponding charge carriers. Furthermore, the term "absorber layer" generally denotes any layer or layer system that includes at least one charge carrier-generating layer.
[0028] In the context of the present invention, the term "alkyl" refers to acyclic saturated hydrocarbon residues which may be branched or linear and unsubstituted or at least monosubstituted, as in the case of Ci-Cao-alkyl, 1 to 30 (i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 24). i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) carbon atoms, or, as in the case of Ci-Cs alkyl, substituted with 1 to 5 (i.e., 1, 2, 3, 4 or 5) carbon atoms. In the context of the present invention, it is conceivable that if one or more of the substituents represent an alkyl or comprise a singly or multiply substituted alkyl, this is preferably substituted with 1, 2, 3, 4 or 5, particularly preferably with 1, 2 or 3, substituents which are independently selected from the group consisting of F, CI, Br, I, -OH, -NO2, -CN, -SH, -NH2,-N(Ci-5-alkyl)2, -N(Ci-5-alkyl)(phenyl), -N(CI-5-alkyl)(CH2-phenyl), -N(Ci-5-alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-Ci-5-alkyl, -C(=O)-phenyl, -C(=S)-Ci-5-alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-Ci-5-alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-Ci-5-alkyl, -C(=O)-N(Ci-5-alkyl)2, -S(=O)-Ci-5-alkyl, -S(=O)-phenyl, -S(=O)2-Ci-s-alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein the above-mentioned Ci-s alkyl groups are linear or branched, and the above-mentioned phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents, which are independently selected from the group consisting of F, CI, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2HS, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl.
[0029] In connection with the present invention, an unsubstituted linear C1-Cso alkyl preferably refers to an alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl and tetracosyl; more preferably selected from the group consisting of hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl and tetracosyl; preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and pentadecyl; preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl;and even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl.;
[0030] In connection with the present invention, an unsubstituted branched Ci-Cao alkyl preferably refers to an alkyl selected from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, neo-pentyl, 2-methyl-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, 2,6-dimethyl-4-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso-hexadecyl, iso-octadecyl, iso-eicosyl and 3-pinanyl-methyl. preferably selected from the group consisting of 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, Iso-hexadecyl, iso-octadecyl, iso-eicosyl, 2-methyltricosyl, 2-ethyldocosyl, 3-ethylhenicosyl, 3-ethylicosy I, 4-propylhenicosyl, propylnonadecyl, 6-butyldodecyl and 5-ethylundecyl.In the context of the present invention, a polysubstituted alkyl is understood to be an alkyl that is either poly-, preferably di-, or trisubstituted, either at different or the same carbon atom, for example, trisubstituted at the same carbon atom as in the case of -CF3, or at different positions as in the case of -(CHCl)-(CH2F). The polysubstitution can occur with the same or different substituents. Representative examples of substituents include, among others, -CH3, -CF3, -CF2H, -CFH2, -(CH2)-OH, -(CH2)-NH2, -(CH2)-CN,-(CH2)-(CF3),-(CH2)-(CHF2),-(CH2)-(CH2F), -(CH2)-(CH2)-O-CH3, -(CH2)-(CH2)-NH2, -(CH2)-(CH2)-CN, -(CF2)-(CF3), -(CH2)-(CH2)-(CF3), and -(CH2)-(CH2)-(CH2)-O-CH3.
[0031] In the context of the present invention, a substituted, linear or branched Ci-Cso alkyl also refers to a branched or linear saturated hydrocarbon group with Ci-Cso carbon atoms substituted with functional groups selected from the group consisting of F, CI, Br, I, -OH, 2-furanyl, -NO2, -CN, -SH, -NH2, -N(Ci-5-alkyl)2, -N(Ci-5-alkyl)(phenyl), -N(Ci-5-alkyl)(CH2-phenyl), -N(Ci-5-alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-Ci-5-alkyl, -C(=O)-phenyl, -C(=S)-Ci-5-alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-Ci-5-alkyl, -C(=O)-)phenyl, -C(=O)-NH2, -C(=O)-NH-Ci-5-alkyl, -C(=O)-N(Ci-5-alkyl)2, -S(=O)-Ci-5-alkyl, -S(=O)-phenyl, -S(=O)2-Ci-5-alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein the above-mentioned Ci-s-alkyl groups are each linear or branched and the above-mentioned phenyl groups are preferably unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents,which are independently selected from the group consisting of F, CI, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2HS, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl.
[0032] In the context of the present invention, a substituted, linear or branched C1-C30 alkyl also refers to a branched or linear saturated hydrocarbon group with C1-C30 carbon atoms substituted with functional groups selected from the group consisting of hydroxy, alkoxy, C(=O)R, CN and SR, preferably selected from the group consisting of 1-methoxymethyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxybutyl, 2-hydroxybutyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecyl, 1-Methoxy-Hexadecyl, 1-Methoxy-Heptadecyl, 1-Methoxy-Octadecyl, 1-Methoxy-Nonadecyl, 1-Methoxy-Eicosyl, 1-Methoxy-Henicosyl, 1-Methoxy-Docosyl, 1-Methoxy-Tricosyl, 1-Methoxy-Tetracosyl, 2-Methoxy-Propyl, 2-Methoxy-Butyl, 2-Methoxy-Pentyl, 2-Methoxyhexyl, 2-Methoxyheptyl,2-Methoxyoctyl, 2-Methoxynonyl, Decyl, 2-Methoxyundecyl, 2-Methoxydodecyl, 2-Methoxytridecyl, 2-Methoxytetradecyl, 2-Methoxypentadecyl, 2-Methoxyhexadecyl, 2-Methoxyheptadecyl, 2-Methoxyoctadecyl, 2-Methoxynonadecyl, 2-Methoxyeicosyl, 2-Methoxyhenicosyl, 2-Methoxydocosyl, 2-Methoxytricosyl, 2-Methoxy-Tetracosyl, 1 -Acetoxy-Methyl, 1 -Acetoxy- Ethyl, 1 -Acetoxy-Propyl, 1 -Acetoxy-Butyl, 1 -Acetoxy-Pentyl, 1 -Acetoxy- Hexyl, 1 -Acetoxy-Heptyl, 1 -Acetoxy-Octyl, 1 -Acetoxy-Nonyl, Decyl, 1-Cyano-Undecyl, 1-Cyano-Dodecyl, 1 -Cyano-Tridecyl, 1 -Cyano-Tetradecyl, 1 -Cyano-Pentadecyl, 1 -Cyano-Hexadecyl, 1-Cyano-Heptadecyl, 1 -Cyano-Octadecyl, 1 -Cyano-Nonadecyl, 1 -Cyano-Eicosyl, 1-Cyano-Henicosyl, 1 -Cyano-Docosyl, 1 -Cyano-Tricosyl, 1 -Cyano-Tetracosyl, 2-Cyano-Propyl, 2-Cyano-Butyl, 2-Cyano-Pentyl, 2-Cyano-Hexyl, 2-Cyano-Heptyl, 2-Cyano-Octyl, 2-Cyano-Nonyl, Decyl, 2-Cyano-Undecyl, 2-Cyano-Dodecyl, 2-Cyano-Tridecyl, 2-Cyano-Tetradecyl, 2-Cyano-Pentadecyl, 2-Cyano-Hexadecyl,2-Cyano-Heptadecyl, 2-Cyano-Octadecyl, 2-Cyano-Nonadecyl, 2-Cyano-Eicosyl, 2-Cyano-Henicosyl, 2-Cyano-Docosyl, 2-Cyano-Tricosyl, 2-Cyano-Tetracosyl, 1 -Thioylmethyl, 1 -Thioylethyl, 1-Thioylpropyl, 1-Thioylbutyl, 1 -Thioylpentyl, 1-Thioylhexyl, 1 -Thioylheptyl, 1 -Thioyloctyl, 1 -Thioylnonyl, Decyl, 1-Thioyl-Undecyl, 1-Thioyl-Dodecyl, 1-Thioyl-Tridecyl, 1-Thioyl-Tetradecyl, 1-Thioyl-Pentadecyl, 1-Thioyl-Hexadecyl, 1-Thioyl-Heptadecyl, 1-Thioyl-Octadecyl, 1-Thioyl-Nonadecyl, 1-Thioyl-Eicosyl, 1-Thioyl-Henicosyl, 1-Thioyl-Docosyl, 1-Thioyl-Tricosyl und 1-Thioyl-Tetracosyl.,
[0033] In the context of the present invention, the term "alkenyl" refers to unsubstituted, linear C2-C3o-alkenyl. Representative examples of alkenyl include 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-Undecenyl, 2-Undecenyl, 1-Dodecenyl, 2-Dodecenyl, 1-Tridecenyl, 2-Tridecenyl, 1-Tetradecenyl, 2-Tetradecenyl, 1-Pentadecenyl, 2-Pentadecenyl, 1-Hexadecenyl, 2-Hexadecenyl, 1 -heptadecenyl, 2-heptadecenyl, 1-Octadecenyl, 2-Octadecenyl, 1-Nonadecenyl, 2-Nonadecenyl, 1-Eicosenyl and 2-Eicosenyl, more preferably selected from 1-Hexenyl, 2-Hexenyl, 1-Heptenyl, 2-Heptenyl, 1-Octenyl, 2-Octenyl, 1-Nonenyl, 2-Nonenyl, 1-Decenyl, 2-Decenyl, 1-Undecenyl, 2-Undecenyl, 1-Dodecenyl, 2-Dodecenyl, 1-Tridecenyl, 2-Tridecenyl, 1-Tetradecenyl, 2-Tetradecenyl, 1-Pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-Hexadecenyl, 1-Heptadecenyl, 2-Heptadecenyl, 1-Octadecenyl, 2-Octadecenyl,1 -Nonadecenyl, 2-Nonadecenyl, 1-Eicosenyl und 2-Eicosenyl, 20-Henicosenyl, 2-Docosenyl, 6-Tricosenyl und 2-Tetracosenyl.,
[0034] Repräsentative Beispiele für unsubstituiertes verzweigtes C2-C3o-Alkenyl sind unter anderem Isopropenyl, Iso-Butenyl, Neo-Pentenyl, 2-Ethyl-Hexenyl, 2-Propyl-Heptenyl, 2-Butyl-Octenyl, 2-Pentyl-Nonenyl, 2-Hexyl-Decenyl, Iso-Hexenyl, Iso-Heptenyl, Iso-Octenyl, Iso-Nonenyl, Iso-Decenyl, Iso-Dodecenyl, Iso-Tetradecenyl, Iso-Hexadecenyl, Iso-Octadecenyl, Iso-Eicosenyl, 2-Methyltricosenyl, 2-Ethyldocosenyl, 3-Ethylhenicosenyl, 3-Ethylicosenyl, 4-Propylhenicosenyl, 4-Propylnonadecenyl, 6-Butyldodecenyl, 5-Ethylundedcenyl, 1,4-Hexadienyl, 1,3-Hexadienyl, 2,5-Hexadienyl, 3,5-Hexadienyl, 2,4-Hexadienyl, 1,3,5-Hexatrienyl, 1,3,6-Heptatrienyl, 1,4,7-Octatrienyl oder 2-Methyl-1,3, 5-Hexatrienyl, 1,3,5,7-Octatetraenyl, 1,3,5,8-Nonatetraenyl, 1,4,7,10-Undecatetraenyl, 2-Ethyl-1,3,6,8-Nonatetraenyl, 2-Ethyl-1,3,5,8-nonatetraenyl, 1,3,5,7,9-decapentaenyl, 1,4,6,8,10-undecapentaenyl, und 1,4,6,9,11-dodecapentaenyl.
[0035] In the context of the present invention, a substituted, linear or branched C2-C3o-alkenyl refers to a branched or linear unsaturated hydrocarbon group having C2-Cso carbon atoms, which is substituted with functional groups selected from alkoxy, C(=O)R, CN and SR; wherein R is hydrogen, substituted or unsubstituted, linear or branched Ci-Cso-alkyl, substituted or unsubstituted, linear or branched C2-C30-alkenyl, substituted or unsubstituted Cs-Cso-cycloalkyl, substituted or unsubstituted Cs-Cso-cycloalkenyl, substituted or unsubstituted Ce-Cso-aryl, substituted or unsubstituted CyCso-arylalkyl.
[0036] In the context of the present invention, the term "alkenyl" further refers to a branched or linear unsaturated hydrocarbon group having C2-C30 carbon atoms, which is substituted with functional groups selected from alkoxy, C(=O)R, CN and SR; preferably selected from the group consisting of 1-methoxyethyleneyl, 2-methoxypropenyl, 4-methoxybutenyl, 3-methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-Methoxytridec-5-enyl, 3-Methoxy-Tetradic-5-enyl, 3-Methoxy-Pentade-12-enyl, 10-Methoxy-Hexadec-15-enyl, 12-Methoxy-Heptadic-16-enyl, 1-Methoxy-Octadec-3-enyl, 1-Methoxy-Nonadec-2-enyl, 1-Methoxy-Eicos-20-enyl, 1-Methoxy-Henicos-2-enyl, 1-Methoxy-Docos-4-enyl, 1-Methoxy-Tricos-22-enyl, 1-Methoxy-Tetracos-23-enyl, 2-Methoxy-prop-1-enyl, 2-Methoxy-but-1-enyl, 2-Methoxy-pent-4-enyl, 2-Methoxy-hex-2-enyl, 2-Methoxy-hept-3-enyl, 2-Methoxy-oct-7-enyl, 2-Methoxy-non-5-enyl,2-Methoxy-undec-10-enyl, 2-Methoxy-dodec-4-enyl, 2-Methoxy-tridec-12-enyl, 2-Methoxy-tetradic-10-enyl, 2-Methoxy-pentadec-14-enyl, 2-Methoxy-Hexadec-1-enyl, 2-Methoxy-Heptadic-1-enyl, 2-Methoxy-Octadic-12-enyl, 2-Methoxy-Nonadec-10-enyl, 2-Methoxy-Eicos-18-enyl, 2-Methoxy-Henicos-2-enyl, 2-Methoxy-Docos-3-enyl, 20-Methoxy-Tricos-2-enyl, 21-Methoxy-Tetracos-4-enyl, 1-Acetoxy-Ethenyl, 1 -Acetoxy- Prop- 1 -enyl, 1-Acetoxy-but-2-enyl, 1-Acetoxy-pent-4-enyl, 1-Acetoxy-hex-2-enyl, 1-Acetoxy-hept-1-enyl, 1-Acetoxy-oct-7-enyl, 1-Acetoxy-non-2-enyl, 5-Acetoxy-dec-3-enyl, 1-Acetoxy-undec-10-enyl, 1-Acetoxy-dodec-2-enyl, 1-Acetoxy-tridec-12-enyl, 10-Acetoxy-tetradec-2-enyl, 15-Acetoxy-pentadec-2-enyl, 10-Acetoxy-hexadec-2-enyl, 11-Acetoxy-heptadec-1-enyl, 13-Acetoxy-octadec-2-enyl, 1-Acetoxy-nonadec-14-enyl, 20-Acetoxy-eicos-19-enyl, 1-Acetoxy-henicos-2-enyl, 1-Acetoxy-docos-10-enyl, 1-Acetoxy-tricos-22-enyl, 1-Acetoxy-tetracos-23-enyl, 1-Cyano-eth-1-enyl, 1-Cyano-prop-2-enyl, 1-Cyano-but-2-enyl,1-Cyano-pent-3-enyl, 1-Cyano-hex-5-enyl, 1-Cyano-hept-6-enyl, 1-Cyano-oct-2-enyl, 1-Cyano-non-3-enyl, 11-Cyano-undec-2-enyl, 10-Cyano-dodec-2-enyl, 10-Cyano-tridec-12-enyl, 1-Cyano-tetradec-3-enyl, 1-Cyano-pentadec-14-enyl, 1-Cyano hexadec-15-enyl, 1-Cyano heptadec-2-enyl, 1-Cyano octadec-3-enyl, 1-Cyano nonadec-18-enyl, 1-Cyano eicos-10-enyl, 1-Cyano henicos-20-enyl, 15-Cyano docos-3-enyl, 1-Cyano-tricos-20-enyl, 1-Cyano-tetracos-2-enyl, 2-Cyano-prop-2-enyl, 2-Cyano-but-1-enyl, 2-Cyano-pent-1-enyl, 2-Cyano-hex-3-enyl, 2-Cyano-hept-6-enyl, 2-Cyano-oct-1-enyl, 2-Cyano-non-8-enyl, 2-Cyano-undec-10-enyl, 2-Cyano-dodec-1-enyl, 2-Cyano-tridec-12-enyl, 2-Cyano-tetradec-10-enyl, 2-Cyano-pentadec-3-enyl, 2-Cyano-Hexadec-2-enyl, 2-Cyano-Heptadec-1-enyl, 2-Cyano-Octadec-12-enyl, 2-Cyano-Nonadec-15-enyl, 2-Cyano-Eicos-1-enyl, 2-Cyano-Henicos-5-enyl, 2-Cyano-docos-20-enyl, 2-Cyano-tricos-22-enyl, 2-Cyano-tetracos-20-enyl, 1-Thionyl-eth-1-enyl, 1-Thionyl-prop-2-enyl, 1-Thionyl-but-2-enyl,1-Thionyl-pent-4-enyl, 1-Thionyl-hex-2-enyl, 1-Thionyl-hept-5-enyl, 1-Thionyl-oct-3-enyl, 1-Thionyl-non-5-enyl, 1-Thionyl-undec-10-enyl, 1-Thionyl-dodec-11-enyl, 1-Thionyl-tridec-2-enyl, 1-Thionyl-tetradec-4-enyl, 1-Thionyl-pentadec-5-enyl, 1-Thionyl-hexadec-3-enyl, 1-Thionyl-heptadec-2-enyl, 1-Thionyl-octadec-3-enyl, 1-Thionyl-Nonadec-15-enyl, 1-Thionyl-Eicos-18-enyl, 1-Thionyl-Henicos-20-enyl, 1-Thionyl-Docos-21-enyl, 1-Thionyl-Tricos-20-enyl und 1-Thionyl-Tetracos-22-enyl.,
[0037] In the context of the present invention, the term "heteroalkyl" refers to an alkyl group in which one or more carbon atoms are each replaced by a heteroatom selected independently from the group consisting of oxygen, sulfur, and nitrogen (NH₄). A heteroalkyl preferably comprises 1, 2, or 3 heteroatoms selected independently from the group consisting of oxygen, sulfur, and nitrogen (NH₄) as chain members. Furthermore, a heteroalkyl can have 2 to 12 members, preferably 2 to 6 members.
[0038] In the context of the present invention, the term "heteroalkenyl" refers to an alkenyl group in which one or more carbon atoms are each replaced by a heteroatom selected independently from the group consisting of oxygen, sulfur, and nitrogen (NH₄). A heteroalkenyl preferably comprises 1, 2, or 3 heteroatoms selected independently from the group consisting of oxygen, sulfur, and nitrogen (NH₄) as chain members. Furthermore, a heteroalkenyl can have 3 to 12 members, preferably 3 to 6 members.
[0039] In the context of the present invention, the term "cycloalkyl" refers to a monocyclic and bicyclic saturated cycloaliphatic residue having 5 to 30 carbon atoms. Representative examples of unsubstituted or branched monocyclic and bicyclic Cs-Cso cycloalkyls include, among others, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, and bicyclo[3.1.1]heptyl.
[0040] In the context of the present invention, a monocyclic and bicyclic C5-C30 cycloalkyl can be further branched with one or more identical or different alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, etc. Representative examples of branched monocyclic and bicyclic Cs-Cw cycloalkyls include, among others, methylcyclohexyl and dimethylcyclohexyl.
[0041] In the context of the present invention, the term "cycloalkenyl" refers to a monocyclic and bicyclic unsaturated cycloaliphatic residue with 5 to 30 carbon atoms, containing one or more double bonds. Representative examples of Cs-Cso cycloalkenyl include cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cycloononenyl, and cyclodecenyl. These residues may be branched with one or more identical or different alkyl groups, preferably with methyl, ethyl, n-propyl, or isopropyl. Representative examples of branched mono- and bicyclic Cs-Cso cycloalkenyl residues include, among others, methylcyclohexenyl and
[0042] Dimethylcyclohexenyl. In the context of the present invention, the term "heterocycloalkyl" means a non-aromatic monocyclic or polycyclic ring with 5 to 30 ring members, in which at least one carbon atom is replaced by at least one heteroatom selected from O, S, and N. Representative examples of heterocycloalkyls include, among others, aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl, and pyranyl.
[0043] In the context of the present invention, the term "heterocycloalkenyl" refers to a non-aromatic unsaturated monocyclic or polycyclic ring with 5 to 30 ring members, in which at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S and N and which has at least one double bond. Representative examples include (2,3)-dihydrofuranyl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1,4)-dihydropyridin-1 -yl, di-hydropyranyl, 2,3-Dihydropyrazol-1-yl, 2,3-Dihydropyrazol-2-yl, 2,3-Dihydropyrazol-3-yl, 2,3-Dihydropyrazol-4-yl, 2,3-Dihydropyrazol-5-yl, 3.4-Dihydropyrazol-1-yl, 3,4-Dihydropyrazol-3-yl, 3,4-Dihydropyrazol-4-yl, 3, 4-Dihydropyrazol-5-yl, 4,5-Dihydropyrazol-1-yl, 4,5-Dihydropyrazol-3-yl, 4,5-Dihydropyrazol-4-yl, 4,5-Dihydropyrazol-5-yl, 2,3-Dihydrooxazol-2-yl, 2,3-Dihydrooxazol-3-yl, 2,3-Dihydrooxazol-4-yl, 2,3-Dihydrooxazol-5-yl, 3, 4-Dihydrooxazol-2-yl, 3,4-Dihydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl, 4,5-Dihydropyrazol-2-yl, 4,5-Dihydropyrazol-3-yl, 4,5-Dihydropyrazol-4-yl, 4,5-Dihydropyrazol-5-yl, 2,5-Dihydrothienyl and (1,2,3,4)-Tetrahydropyridin-1-yl.
[0044] In the context of the present invention, the term "aryl" refers to aromatic compounds that may have more than one aromatic ring. Representative examples of substituted and unsubstituted C6-C30 aryl include, among others, phenyl, benzyl, cyclohexyl(phenyl)methyl, naphthyl, anthracenyl, tetraphenyl, phenalenyl, and phenanthrenyl.
[0045] In the context of the present invention, the term "heteroaryl" refers to a mono- or polycyclic, preferably a mono-, bi- or tricyclic aromatic hydrocarbon residue with preferably 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 ring members, particularly preferably with 5, 6, 9, 10, 13 or 14 ring members, and most preferably with 5 or 6 ring members in which one or more carbon atoms as ring members are replaced by heteroatoms, each of which is independently selected from the group consisting of oxygen, sulfur and nitrogen (NH₃). A heteroaryl can contain 1, 2, 3, 4, or 5, preferably 1, 2, or 3, heteroatom(s) as ring member(s), each independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH₃). A heteroaryl can be unsubstituted, simply substituted, or identically or differently multiply substituted.
[0046] Representative examples of heteroaryl include thienyl, furyl, pyrrolyl, pyrazolyl, pyrazinyl, pyranyl, triazolyl, pyridinyl, imidazolyl, indolyl, isoindolyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[d]thiazolyl, benzodiazolyl, benzotriazolyl, benzoxazolyl, benzisoxazolyl, thiazolyl, Thiadiazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridazinyl, pyrimidinyl, indazolyl, quinoxalinyl, quinazolinyl, quinolinyl, naphthridinyl and isoquinolinyl.
[0047] In the context of the present invention, the term "arylalkyl" refers to an aryl ring bonded to an alkyl chain. Representative examples of arylalkyls include, among others, 1-phenylmethyl, 1-phenylethyl, 1-phenylpropyl, 1-phenylbutyl, 1-methyl-1-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl, 3-phenylbutyl, and 2-methyl-3-phenylpropyl.
[0048] In the context of the present invention, it is conceivable that if one or more of the substituents represent an aryl, heteroaryl or arylalkyl, or comprise an aryl or heteroaryl that is singly or multiply substituted, it may preferably be substituted with 1, 2, 3, 4 or 5, particularly preferably with 1, 2 or 3, substituents that are independently selected from the group consisting of F, CI, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C1-5 alkyl, -(CH2)-O-Ci-5-alkyl, -C 2.5 alkenyl, -C 2.5alkynyl, -C C-Si(CH3)3, -C=C-Si(C2Hs)3, -S-Ci-5-alkyl, -S-phenyl, -S-CH2-phenyl, -O-Ci-5-alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-Ci-5-alkyl, -S(=O)-Ci-5-alkyl, -NH-Ci-5-alkyl, N(Ci-5alkyl)2, -C(=O)-O-Ci-5-alkyl, -C(=O)-H; -C(=O)-Ci-5-alkyl, -CH2-OC(=O)-phenyl, -OC(=O)-phenyl, -NH-S(=O)2-Ci-5-alkyl, -NH-C(=O)-Ci-5-alkyl, -C(=O)-NH2, -C(=O)-NH-Ci-5-alkyl, -C(=O)-N(Ci-5-alkyl)2, pyrazolyl, phenyl, furyl (furanyl), thiazolyl, thiadiazolyl, thiophenyl (thienyl), benzyl and phenethyl, wherein the above-mentioned C1-5-alkyl groups are each linear or branched and the cyclic substituents or the cyclic groups of these substituents themselves are unsubstituted or substituted with 1, 2, 3, 4 or 5, preferably with 1, 2, 3 or 4, substituents which are independently selected from the group consisting from F, CI, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C1.5 alkyl, -(CH2)-O-CI-5-alkyl, -C2-5 alkenyl, -C2.salkynyl, -C=C-Si(CH3)3, -C=C-Si(C2H5)3, -S-Ci-5-alkyl, -S-phenyl, -S-CH2-phenyl, -O-Ci-5-alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2and -S-CH2F; Particularly preferred are the substituents each independently selected from the group consisting of F, CI, Br, I, -CN, -NO2Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Isobutyl, 2-Butyl, tert-Butyl, n-Pentyl, Neopentyl, Ethenyl, Allyl, Ethynyl, Propynyl, -C=C-Si(CH3)3, -C=C-Si(C2Hs)3, -CH2-O- CH3, -CH2-O-C2H5, -SH, -NH2, -C(=O)-OH, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH. 3I-S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -OC(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -0-CHF2, -0-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=0)2-phenyl, pyrazolyl, phenyl, -N(CH3)2, -N(C2H5)2, -NH-CH3, -NH-C2H5, -CH2-OC(=O)-phenyl, -NH-S(=O)2-CH3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-OC(CH3)3, -C(=O)-H, -C(=O)-CH3, -C(=O)-C2H5, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -OC(=O)-phenyl, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, Phenyl, Furyl (Furanyl), Thiadiazolyl, Thiophenyl (Thienyl) and Benzyl, wherein the cyclic substituents or the cyclic groups of these substituents are themselves unsubstituted or substituted with 1, 2, 3, 4 or 5, preferably with 1, 2, 3 or 4, substituents which are independently selected from the group consisting of F, CI, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, isobutyl, 2-butyl, tert.-Butyl, n-Pentyl, Neopentyl, Ethenyl, Allyl, Ethynyl, Propynyl, -C C-Si(CH3)3, -C C-Si(C2H5)3, -CH2-O-CH3, -CH2-O-C2H5, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH3, -S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -O-C(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -0-CHF2, -0-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F.
[0049] Im Kontext der vorliegenden Erfindung kann ein substituiertes Aryl ausgewählt werden aus der Gruppe bestehend aus 2-Methylphenyl, 3-Methylphenyl, 4-Methylphenyl, 2-Fluorphenyl, 3-Fluorphenyl, 4-Fluorphenyl, 2-Cyanophenyl, 3-Cyanophenyl, 4-Cyanophenyl, 2-Aminophenyl, 3-Aminophenyl, 4-Aminophenyl, 2-Dimethylaminophenyl, 3-Dimethylaminophenyl, 4-Dimethylaminophenyl, 2-Methylaminophenyl, 3-Methylaminophenyl, 4-Methylaminophenyl, 2-Acetylphenyl, 3-Acetylphenyl, 4-Acetylphenyl, 2-Methylsulfinylphenyl, 3-Methylsulfinylphenyl, 4-Methylsulfinylphenyl, 2-Methylsulfonylphenyl, 3-Methylsulfonylphenyl, 4-Methylsulfonylphenyl, 2-Methoxyphenyl, 3-Methoxyphenyl, 4-Methoxyphenyl, 2-Chlorphenyl, 3-Chlorphenyl, 4-Chlorphenyl, 2-Ethoxyphenyl, 3-Ethoxyphenyl, 4-Ethoxyphenyl, 2-Trifluormethylphenyl, 3-Trifluormethylphenyl, 4-Trifluormethylphenyl, 2-Difluormethylphenyl, 3-Difluormethylphenyl, 4-Difluormethylphenyl, 2-Fluormethylphenyl, 3-Fluormethylphenyl, 4-Fluormethylphenyl, 2-Nitrophenyl, 3-Nitrophenyl,4-Nitrophenyl, 2-Ethylphenyl, 3-Ethylphenyl, 4-Ethylphenyl, 2-Propylphenyl, 3-Propylphenyl, 4-Propylphenyl, 2-lsopropylphenyl, 3-lsopropylphenyl, 4 Isopropylphenyl, 2-tert.-Butylphenyl, 3-tert.-Butylphenyl, 4-tert. Butylphenyl, 2-Carboxyphenyl, 3-Carboxyphenyl, 4-Carboxyphenyl, 2-Ethinylphenyl, 3-Ethinylphenyl, 4-Ethinylphenyl, 2-Ethinylphenyl, 3-Ethinylphenyl, 4-Ethinylphenyl, 2-Allylphenyl, 3-Allylphenyl, 4-Allylphenyl, 2-Trimethylsilanylethinylphenyl, 3-Trimethylsilanylethynylphenyl, 4-Trimethylsilanylethynylphenyl, 2-Formylphenyl, 3-Formylphenyl, 4-Formylphenyl, 2-Acetaminophenyl, 3-Acetaminophenyl, 4-Acetaminophenyl, 2-Dimethylaminocarbonylphenyl, 3-Dimethylaminocarbonylphenyl, 4-Dimethylaminocarbonylphenyl, 2-Methoxymethylphenyl, 3-Methoxymethylphenyl, 4- Methoxymethylphenyl, 2-Ethoxymethylphenyl, 3-Ethoxymethylphenyl, 4-Ethoxymethylphenyl, 2-Aminocarbonylphenyl, 3-Aminocarbonylphenyl, 4-Aminocarbonylphenyl, 2- Methylaminocarbonylphenyl, 3-Methylaminocarbonylphenyl,4-Methylaminocarbonylphenyl, 2-Carboxymethylesterphenyl, 3-Carboxymethylesterphenyl, 4-Carboxymethylesterphenyl, 2-Carboxyethylesterphenyl, 3-Carboxyethylesterphenyl, 4-Carboxyethylesterphenyl, 2-Carboxy-tert. - Butylesterphenyl, 3-Carboxy-tert.-butylesterphenyl, 4-Carboxy-tert.- Butylesterphenyl, 2-Methylmercaptophenyl, 3-Methylmercaptophenyl, 4-Methylmercaptophenyl, 2-Ethylmercaptophenyl, 3-Ethylmercaptophenyl, 4-Ethylmercaptophenyl, 2-Biphenyl, 3-Biphenyl, 4-Biphenyl, 2-Bromphenyl, 3-Bromphenyl, 4-Bromphenyl, 2-Jodphenyl, 3-Jodphenyl, 4-Jodphenyl, 2-Trifluormethoxyphenyl, 3-Trifluormethoxyphenyl, 4-Trifluormethoxyphenyl, 2-Fluor- 3-trifluormethylphenyl, 2-Fluor-4-methylphenyl, (2,3)-Difluorphenyl, (2,3)-Dimethylphenyl, (2,3)-Dichlorphenyl, 3-Fluor-2-trifluormethylphenyl, (2,4)-Dichlorphenyl, (2,4)-Difluorphenyl, 4-Fluor-2-trifluormethylphenyl, (2,4)-Dimethoxyphenyl, 2-Chlor-4-fluorphenyl, 2-Chlor-4-nitrophenyl, 2-Chlor-4-methylphenyl, 2-Chlor-5-trifluormethylphenyl,2-Chlor-5-methoxyphenyl, 2-Brom-5-trifluormethylphenyl, 2-Brom-5-methoxyphenyl, (2,4)-Dibromphenyl, (2,4)-Dimethylphenyl, 2-Fluor-4-trifluormethylphenyl, (2,5)-Difluorphenyl, 2-Fluor-5-trifluormethylphenyl, 5-Fluor-2-trifluormethylphenyl, 5-Chlor-2-trifluormethylphenyl, 5-Brom-2-trifluormethylphenyl, (2,5)-Dimethoxyphenyl, (2,5)-Bis-trifluormethylphenyl, (2,5)-Dichlorphenyl, (2,5)-Dibromphenyl, 2-Methoxy-5-nitrophenyl, 2-Fluoro-6-trifluoro-methylphenyl, (2,6)-Dimethoxyphenyl, (2, 6)-Dimethylphenyl, (2,6)-Dichlorphenyl, 2-Chlor-6-fluorphenyl, 2-Brom-6-chlorphenyl, 2-Brom-6-fluorphenyl, (2,6)-Difluorphenyl, (2, 6)-Difluor-3-methylphenyl, (2,6)-Dibromphenyl, (2,6)-Dichlorphenyl, 3-Chlor-2-fluorphenyl, 3-Chlor-5-methylphenyl, (3,4)-Dichlorphenyl, (3,4)-Dimethylphenyl, 3-Methyl-4-methoxyphenyl, 4-Chlor-3-nitrophenyl, (3,4)-Dimethoxyphenyl, 4-Fluor-3-trifluormethylphenyl, 3-Fluor-4-trifluormethylphenyl, (3,4)-Difluorphenyl, 3-Cyano-4-fluorphenyl, 3-Cyano-4-methylphenyl,3-Cyano-4-methoxyphenyl, 3-Brom-4-fluorphenyl, 3-Brom-4-methylphenyl, 3-Brom-4-methoxyphenyl, 4-Chlor-2-fluorphenyl, 4-Chlor-3-trifluormethyl, 4-Brom-3-methylphenyl, 4-Brom-5-methylphenyl, 3-Chlor-4-fluorphenyl, 4-Fluor-3-nitrophenyl, 4-Brom-3-nitrophenyl, (3,4)-Dibromphenyl, 4-Chlor-3-methylphenyl, 4-Brom-3-methylphenyl, 4-Fluor-3-methylphenyl, 3-Fluor-4-methylphenyl, 3-Fluor-5-methylphenyl, 2-Fluor-3-methylphenyl, 4-Methyl-3-nitrophenyl, (3,5)-Dimethoxyphenyl, (3,5)-Dimethylphenyl, (3,5)-Bis-trifluormethylphenyl, (3,5)-Difluorophenyl, (3,5)-Dinitrophenyl, (3,5)-Dichlorophenyl, 3-Fluor-5-trifluormethylphenyl, 5-Fluor-3-trifluormethylphenyl, (3,5)-Dibromphenyl, 5-Chlor-4-fluorphenyl, 5-Chlor-4-fluorphenyl, 5-Brom-4-methylphenyl, (2,3,4)-Trifluorphenyl, (2,3,4)-Trichlorphenyl, (2,3,6)-Trifluorphenyl, 5-Chlor-2-methoxyphenyl, (2,3)-Difluor-4-methyl, (2,4,5)-Trifluorphenyl, (2,4,5)-Trichlorphenyl, (2,4)-Dichlor-5-fluorphenyl, (2,4, 6)-Trichlorphenyl, (2,4,6)-Trimethylphenyl, (2,4,6)-Trifluorphenyl, (2,4,6)-Trimethoxyphenyl, (3,4,5)-Trimethoxyphenyl, (2,3,4, 5)-Tetrafluorphenyl, 4-Methoxy-(2,3,6)-trimethylphenyl, 4-Methoxy-(2,3,6)- trimethylphenyl, 4-Chlor-2,5-dimethylphenyl, 2-Chlor-6-fluor-3-methylphenyl, 6-Chlor-2-fluor-3-methyl, (2,4,6)-trimethylphenyl und (2,3,4,5,6)-Pentafluorphenyl.,
[0050] Im Kontext der vorliegenden Erfindung sind Beispiele für ein substituiertes Heteroaryl 3-Methylpyrid-2-yl, 4-Methylpyrid-2-yl, 5-Methylpyrid-2-yl, 6-Methylpyrid-2-yl, 2-Methylpyrid-3-yl, 4-Methylpyrid-3-yl, 5-Methylpyrid-3-yl, 6-Methylpyrid-3-yl, 2-Methylpyrid-4-yl, 3-Methylpyrid-4-yl, 3-Fluoropyrid-2-yl, 4-Fluoropyrid-2-yl, 5-Fluoropyrid-2-yl, 6-Fluoropyrid-2-yl, 3-Chloropyrid-2-yl, 4-Chloropyrid-2-yl, 5-Chlorpyrid-2-yl, 6-Chlorpyrid-2-yl, 3-Trifluormethylpyrid-2-yl, 4-T rifl uormethy I py rid-2-y 1 , 5-T rifl uorm ethyl pyrid-2-yl , 6-T rifl uorm ethyl pyrid-2-yl , 3-Methoxypyrid-2-yl, 4-Methoxypyrid-2-yl, 5-Methoxypyrid-2-yl, 6-Methoxypyrid-2-yl, 4-Methylthiazol-2-yl, 5-Methylthiazol-2-yl, 4-T rifluormethylthiazol-2-yl, 5-T rifluormethylthiazol-2-yl, 4-Chlorthiazol-2-yl, 5-Chlorthiazol-2-yl, 4-Bromothiazol-2-yl, 5-Bromothiazol-2-yl, 4-Fluorothiazol-2-yl, 5-Fluorothiazol-2-yl, 4-Cyanothiazol-2-yl, 5-Cyanothiazol-2-yl, 4-Methoxythiazol-2-yl, 5-Methoxythiazol-2-yl, 4-Methyloxazol-2-yl,5-Methyloxazol-2-yl, 4-Trifluormethyloxazol-2-yl, 5-Trifluormethyloxazol-2-yl, 4-Chlorooxazol-2-yl, 5-Chlorooxazol-2-yl, 4-Bromooxazol-2-yl, 5-Bromooxazol-2-yl, 4-Fluorooxazol-2-yl, 5-Fluorooxazol-2-yl, 4-Cyanooxazol-2-yl, 5-Cyanooxazol-2-yl, 4-Methoxyoxazol-2-yl, 5-Methoxyoxazol-2-yl, 2-Methyl-(1 ,2,4)-thiadiazol-5-yl, 2-T rifluormethyl-(1 , 2 , 4)-thiad iazoly l-5-y 1 , 2-Chlor-(1 , 2 ,4)-thi ad iazol-5-y 1 , 2-fluoro-(1 ,2,4)-thiadiazol-5-yl, 2-methoxy-(1,2,4)-thiadiazol-5-yl, 2-cyano-(1,2, 4)-thiadiazol-5-yl, 2-Methyl-(1,2,4)-oxadiazol-5-yl, 2-Trifluormethyl-(1,2,4)-oxadiazol-5-yl, 2-Chlor-(1,2, 4)-Oxadiazol-5-yl, 2-Fluor-(1 ,2,4)-oxadiazol-5-yl, 2-Methoxy-(1 ,2,4)-oxadiazol-5-yl und 2-Cyano-(1 ,2,4)-oxadiazol-5-yi.,
[0051] Es ist bevorzugt, dass R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, Cs-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, C5-C30 Heteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, C6-C30 Arylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR',-NHCOR‘, -NHCOOR', -NHCONHR', Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind. Es ist bevorzugt, dass R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, Cs-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, C5-C30 Heteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy,Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, C6-C30 Arylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, -COOH, -COR', -COOR', -CONHR', -NHCOR', -NHCOOR', -NHCONHR', and Acyl, each of these groups being substitutable, are selected.
[0052] It is preferred that R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Csocycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, C5-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, Hydroxy, C1-C30 Hydroxyalkyl, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, benzyloxy, and C5-C30 heteroaryloxy, each of these groups being substitutable, have been selected.
[0053] It is preferred that R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, C5-Cso heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, each of these groups may be substituted.
[0054] It is preferred that R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, secbutyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, secbutyl, tert-butyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, and ethyl. It is preferred that R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C3o alkynyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkyl heteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl,C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, C5-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR‘, -NHCOR', -NHCOOR', -NHCONHR', Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind.,
[0055] It is preferred that R9', R10', R11', R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkyl heteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, Ce-Cso aryl, C6-C30 arylalkyl, Ce-Cso arylalkenyl, C6-C30 arylheteroalkyl, C5-C30 heteroaryl, Cs-CsoHeteroarylalkyl, C5-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, and Acyl, each of these groups being substitutable, are selected.
[0056] It is preferred that R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, Cs-Csoheteroalkenyl, C5-C30 cycloalkyl, Cs-Csocycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, C5-C30 heteroarylalkyl, C5-C30 heteroarylalkenyl, C5-C30 heteroarylheteroalkyl, hydroxy, C1-C30 hydroxyalkyl, Ce-Csoaryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups can be substituted, are selected.It is preferred that R9', R10', R1 T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, hydroxy, and C1-C30 hydroxyalkyl, each of these groups being substitutable.
[0057] It is preferred that R9', R10', R1T, R12', R13' and R14' are selected independently from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexyl methyl, cyclododecyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, sec-butyl, tert-butyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, and ethyl.
[0058] Es ist bevorzugt, dass R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected; where R5, R6, R7, R8, R9 and R10 are hydrogen.
[0059] Es ist bevorzugt, dass RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1, -NHCONHR', Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected; wherein R9', R10', R1T, R12', R13' and R14' are hydrogen.
[0060] Es ist bevorzugt, dass R1‘, R2‘, R3‘ und R4‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind;where R5', R6', R7', R8', R9', R10', R1T, R12', R13' and R14' are hydrogen.
[0061] Es ist bevorzugt, dass R1, R2, R3 und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C30 Alkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Cs-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, C5-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, C5-C30 Cycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, C6-C30 Arylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, Alkoxycarbonyl, Alkylaminocarbonyl,Sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected.
[0062] It is preferred that R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, Cs-CsoAryl, C6-C30 arylalkyl, C6-C30 arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, Cs- CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, and Acyl, each of these groups being substitutable, are selected.
[0063] It is preferred that R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkyl heteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkyl heteroalkyl, C5-C30 heteroaryl, C5-C30 heteroarylalkyl, Cs-Cso heteroarylalkenyl, C5-C30 heteroarylheteroalkyl, hydroxy, C1-C30 hydroxyalkyl, Ce-Cso aryloxy, Ce-Cso arylalkyloxy, phenoxy, benzyloxy, and C5-C30 heteroaryloxy, where each of these groups can be substituted, are selected.
[0064] It is preferred that R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, C5-C30 heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, each of these groups may be substituted.
[0065] It is preferred that R1, R2, R3 and R4 are independently selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably from the group consisting of chlorine and bromine, wherein R1, R2, R3 and R4 are particularly preferably bromine.
[0066] It is preferred that R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexyl methyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, sec-butyl, tert-butyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl.
[0067] Es ist bevorzugt, dass RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘, bevorzugt RT, R2‘, R3‘ und R4‘, unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5-C30 Heteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino,Sulfinylamino, -COOH, -COR', -COOR', -CONHR', -NHCOR', -NHCOOR', -NHCONHR', alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected.
[0068] Es ist bevorzugt, dass R1‘, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘, bevorzugt R1‘, R2‘, R3‘ und R4‘, unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5-C30 Heteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, und Acyl, wobei jeder dieser Gruppen substituiert sein kann,are selected.
[0069] It is preferred that R1', R2', R3', R4', R5', R6', R7' and R8', preferably R1', R2', R3' and R4', independently of one another, from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkyl heteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, Cs-Cso heterooarylalkyl, Cs-Cso heterooarylalkenyl, C5-C30 heteroaryl heteroalkyl Hydroxy, C1-C30 Hydroxyalkyl, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups may be substituted, are selected.
[0070] It is preferred that R1', R2', R3', R4', R5', R6', R7' and R8', preferably R1', R2', R3' and R4', are selected independently from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, each of these groups may be substituted.
[0071] It is preferred that RT, R2', R3', R4', R5', R6', R7' and R8', particularly preferably R1', R2', R3' and R4', are independently selected from the group consisting of fluorine, chlorine, bromine and iodine, particularly preferably from the group consisting of chlorine and bromine, wherein R1, R2, R3 and R4 are particularly preferably bromine.
[0072] It is preferred that R1', R2', R3', R4', R5', R6', R7' and R8', particularly preferably R1', R2', R3' and R4', independently of one another, from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexyl methyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, sec-butyl, tert-butyl, phenyl, and benzyl, particularly preferably from the group consisting of hydrogen, Methyl, ethyl, phenyl and benzyl have been selected.
[0073] It is preferred that one or more passivation layers be a compound of formula (A-1)
[0074] T
[0075] Ar Ar
[0076] '''W
[0077]
[0078] Ar Formula (A-1)
[0079] comprise, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, and I soquinolyl, each of these groups being substitutable.
[0080] It is preferred that one or more passivation layers be a compound of formula (A-2)
[0081]
[0082] Formula (A-2)
[0083] comprise, where X is selected from the group consisting of CI, Br, I, F, CN, NO2, CH3, CF3, OCH3 and SO3H.
[0084] It is preferred that one or more passivation layers be a compound of formula (A-3)
[0085]
[0086] Formula (A-3)
[0087] include.
[0088] It is preferred that one or more passivation layers be a compound of formula (B-1)
[0089]
[0090] Formula (B-1)
[0091] comprising, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl, each of these groups may be substituted.
[0092] It is preferred that one or more passivation layers be a compound of formula (B-2)
[0093] . |
[0094]
[0095] Formula (B-2)
[0096] comprise, where X is selected from the group consisting of CI, Br, I, F, CN, NO2, CH3, CF3, OCH3 and SO3H.
[0097] It is preferred that one or more passivation layers be a compound of formula (B-3)
[0098]
[0099] Formula (B-3)
[0100] include.
[0101] It is preferred that the one or more passivation layers have a layer thickness of 0.1 to 200 nm, particularly preferably of 1 to 50 nm.
[0102] It is preferred that one or more passivation layers are produced or applied from the gas phase by means of physical vapor deposition (PVD), particularly preferably by means of thermal evaporation.
[0103] It is preferred that one or more passivation layers further comprise a material selected from the group consisting of an alkali metal fluoride, an alkylammonium iodide, an arylalkylammonium iodide, a diaminoalkyl dihydroiodide and mixtures of two or more thereof, preferably selected from the group consisting of lithium fluoride, phenethylammonium iodide (PEAI), 1,3-diaminopropane dihydroiodide (PDADI), n-butylammonium iodide (BAI) and a mixture of two or more thereof.
[0104] It is preferred that the positive electrode and the negative electrode are selected independently from the group consisting of a metal of group XI of the periodic table, a metal oxide of a metal of groups XII-XIV, and mixtures thereof. It is further preferred that the positive electrode and the negative electrode are selected independently from the group consisting of Ag, Au, Cu, and mixtures thereof. Alternatively, it is preferred that the positive electrode and the negative electrode are selected independently from the group consisting of indium oxide, tin oxide, zinc oxide, titanium oxide, aluminum oxide, zirconium oxide, and mixtures thereof.
[0105] It is preferred that the electron transport layer comprises one or more inorganic and / or organic materials, particularly preferably one or more organic materials.
[0106] In the case that the solar cell comprises one or more inorganic and / or organic materials, it is preferred that the one or more organic materials are selected from the group consisting of unsubstituted or substituted fullerenes, PCBM ([6,6]-phenyl-C61 butyric acid methyl ester), CMC (carboxymethylcellulose), ICBA, NDI (naphthalene diimide), naphthalene diimide-based polymers, PDI (perylene diimide), perylene diimide-based polymers, TDI (terylene diimide), terylene diimide-based polymers, indacene dithiophene-based compounds, anthracene-based compounds, tetracene-based compounds, pentacene-based compounds, derivatives thereof and mixtures thereof, particularly preferably from the group consisting of C60, C70, PCBM (6,6-phenyl-C61 butyric acid methyl ester), PDI (perylene diimide) and mixtures thereof.
[0107] Furthermore, it is preferred that the one or more inorganic materials comprise one or more metal oxides, preferably one or more metal oxides selected from the group consisting of tin oxide, zinc oxide, titanium oxide, aluminum oxide, zirconium oxide, indium oxide, and mixtures thereof. It is further preferred that the one or more metal oxides are doped with an element E, wherein E is an element of Groups I to III of the periodic table, particularly preferably an element of Groups I to II, particularly preferably selected from the group consisting of H, Na, Li, and K, particularly preferably H.
[0108] It is preferred that the electron transport layer has a layer thickness of 0.1 nm to 750 nm, particularly preferably of 5 nm to 500 nm, particularly preferably of 10 nm to 200 nm.
[0109] It is preferred that the electron transport layer is produced by a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of sputtering, electron beam evaporation, physical vapor deposition (PVD), rotary coating, doctor blade coating, inkjet printing, chemical vapor deposition (CVD), laser beam evaporation (PLD), and combinations of two or more of these processes. It is preferred that the hole transport layer comprises one or more polymers, preferably one or more polymers selected from the group consisting of PTAA (poly[bis-(4-phenyl)-(2,4,6-trimethylphenyl)amine]), PEDOT:PSS (poly(ethylenedioxythiophene):
[0110] Poly(styrenesulfonate)), Poly-TPD (Poly[N,N'-bis(4-butylphenyl)-N,N-bis(phenyl)benzidine]), and P3HT (Poly(3-hexylthiophene)).
[0111] It is preferred that the hole transport layer comprises one or more materials based on small molecules, particularly preferably Spiro-OMeTAD (2,27,7'-tetraakis-(N,N-Di-4-methoxyphenylamino)-9,9'spirobifluorene).
[0112] It is preferred that the hole transport layer comprises one or more self-assembled layers. Publication WO 2019 / 207029 A1 is considered reference RF1 and is hereby incorporated in its entirety into this document by reference. It is preferred that the one or more self-assembled layers comprise at least one molecule of formula (I) of reference RF1, wherein L is a connecting fragment, A is an anchoring group, and HTF (hole transporting fragment) is a hole-conducting fragment selected from one of formulas (II) or (III) of reference RF1, wherein Z and D are homocyclic or at least one of Z or D comprises a heteroatom, the heteroatom being particularly preferably selected from the group consisting of N, S, O, and Si, and wherein Z is a Cs- or Cs-substituted or unsubstituted aromatic group, and D is N or a Cs- or Cs-aromatic group.wherein two carbon atoms of aromatic group D are each bonded to one of the two aromatic groups Z to form a tricycloundecane, a tricyclotridecane, or a tricyclotetradecane derivative; or R is selected independently from the group consisting of H, Ci- to Cw-alkyl; C2- to Cw-alkenyl, C3- to C2o-cycloalkyl, C3- to Cs-heterocycloalkyl, alkoxy, aryloxy, alkylthio, arylthio, amino, amido, ester, carboxylic acid, dialkoxydiphenylamine, carbamate, urea, ketone, aldehyde, cyano, nitro, halogen, cycloalkylalkyl, and heterocycloalkylalkyl.
[0113] In preferred embodiments, the connecting fragment L is selected from the group consisting of Ci to Cg alkylenes, C4 to C2o arylenes, C4 to C2o heteroarylenes, C4 to C2o alkylarylenes, and C4 to C2o heteroalkylarylenes, wherein the heteroatoms are selected from O, N, S, Se, and Si, and wherein the aforementioned alkylenes, arylenes, heteroarylenes, alkylarylenes, heteroalkylarylenes, and heteroalkylarylenes, if they comprise three or more carbon atoms, may be linear, branched, or cyclic. In preferred embodiments, the anchor group A is selected from the group consisting of phosphonic acid, phosphoric acid, sulfuric acid, sulfonic acid, carboxylic acid, and siloxanes.
[0114] In preferred embodiments, the hole-conducting fragment HTF is selected from the group consisting of formulas (IV) to (XIX) of reference RF1.
[0115] Furthermore, it is preferred that one or more self-assembled layers are selected from the group consisting of 2PACz ([2-(9H-Carbazol-9-yl)ethyl]phosphonic acid), MeO-2PACz ([2-(3,6-Dimethoxy-9H-carbazol-9-yl)ethyl]phosphonic acid) and ((4-(9H-Carbazol-9-yl)butyl)phosphonic acid).
[0116] It is preferred that the hole transport layer comprises one or more inorganic materials, particularly preferably one or more inorganic materials selected from the group consisting of copper oxide, nickel oxide, copper iodide, copper thiocyanate, and mixtures of two or more, particularly preferably from the group consisting of copper oxide, nickel oxide, and mixtures thereof. Furthermore, it is preferred that the hole transport layer comprises one or more self-assembled layers and one or more inorganic materials.
[0117] It is preferred that the hole transport layer is doped with a material selected from the group consisting of Li-TFSI (lithium bis(trifluoromethanesulfonyl)imide), TBP (4-tert-butylpyridine), FK20 (tris[2-2(1 H-pyrazol-1-yl)-4-tert-butylpyridine]-cobalt(1ll), tris[bis(trifluoromethanesulfonyl)imide]), F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinoldimethane) and mixtures of two or more of these.
[0118] It is preferred that the hole transport layer has a layer thickness of 0.1 nm to 500 nm, particularly preferably of 2 nm to 200 nm.
[0119] It is preferred that the hole transport layer is produced by a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of sputtering, electron beam evaporation, physical vapor deposition (PVD), rotary coating, doctor blade coating, dip coating and inkjet printing, and combinations of two or more of these processes. It is preferred that the absorber layer is a perovskite layer.
[0120] The term "perovskite layer" generally refers to any layer that contains or comprises perovskite. The term "perovskite" generally refers to any material. An example is 3D perovskites with a chemical ABXa structure, where X can be iodine, bromine, or chlorine (or any mixture thereof), where B can be lead or tin (or any mixture thereof), and where A can be methylammonium, formamidinium, cesium, potassium, or rubidium (or any mixture thereof). Any deviations from and impurities in the aforementioned chemical structure of 3D perovskites are also included. Another example is low-dimensional perovskites whose chemical structure differs from the ABX3 structure, forming 2D perovskites such as Ruddlesden-Popper and Dion-Jacobson perovskites.
[0121] In the case that the absorber layer is a perovskite layer, it is preferred that the perovskite layer has a thickness of 50 nm to 10 pm, particularly preferably of 500 nm to 1 pm.
[0122] It is preferred that the perovskite layer is produced by a deposition process based on a low-pressure or vacuum coating process, particularly preferably a deposition process selected from the group consisting of physical vapor deposition (PVD), rotary coating, doctor blade coating, inkjet printing, spray coating, slot die coating, roller coating, gravure printing, chemical vapor deposition (CVD), laser beam evaporation (PLD), sputtering and combinations of two or more of these processes.
[0123] It is preferred that the absorber layer comprises an organic absorber.
[0124] In the case that the absorber layer comprises an organic absorber, it is preferred that the organic absorber be selected from the group consisting of polymers, dendrimers, and macromers, preferably selected from the group consisting of PW poly(phenylvinyl), CN-PPV, MEH-PPV, phthalocyanine, polyacetylene, and mixtures thereof. Furthermore, it is preferred that the absorber layer has a thickness of 800 nm to 10 pm, particularly preferably 1 pm to 5 pm.
[0125] It is preferred that the absorber layer is produced by a deposition process based on a low-pressure or vacuum coating process, particularly preferably a deposition process selected from the group consisting of physical vapor deposition (PVD), rotary coating, doctor blade coating, inkjet printing, spray coating, slot die coating, roller coating, gravure printing, chemical vapor deposition, laser beam evaporation, cathode sputtering and combinations of two or more of these processes.
[0126] It is preferred that the solar cell also has one or more buffer layers.
[0127] In the event that the solar cell further comprises one or more buffer layers, it is preferred that the buffer layer contains a material selected from the group consisting of bathocuproin (BCP), lithium fluoride, magnesium fluoride, polyfluorene, and mixtures of two or more thereof. It is further preferred that the buffer layer comprises one or more inorganic nanoparticles, particularly preferably inorganic nanoparticles selected from the group consisting of aluminum oxide, zinc oxide, titanium oxide, nickel oxide, lead sulfide, and mixtures of two or more thereof.
[0128] It is preferred that one or more passivation layers are arranged between the absorber layer and the electron transport layer.
[0129] It is preferred that the electron transport layer is arranged between the absorber layer and the one or more passivation layers.
[0130] It is preferred that one or more passivation layers are arranged between the absorber layer and the hole transport layer.
[0131] It is preferred that the solar cell further comprises a substrate. In the case that the solar cell comprises a substrate, it is preferred that the one or more passivation layers are arranged over 60 to 100%, particularly preferably over 80 to 100%, particularly preferably over 90 to 100%, particularly preferably over 95 to 100%, particularly preferably over 99 to 100% of the substrate length.
[0132] It is preferred that the substrate is selected from the group consisting of glass, a polymer film, and silicon (Si). Furthermore, it is preferred that Si also serves as the absorber layer when used as a substrate.
[0133] It is preferred that the one or more passivation layers and the electron transport layer are applied simultaneously by co-evaporation. It is also preferred that the one or more passivation layers and the electron transport layer are integrated in a common layer, wherein the one or more passivation layers serve as a matrix enclosing the one or more inorganic and / or organic materials of the electron transport layer.
[0134] It is preferred that the solar cell is a subcell of a multi-junction solar cell, and wherein the multi-junction solar cell comprises
[0135] at least one first layer stack, wherein the first layer stack comprises at least one substrate, at least one first electrode and at least one first layer;
[0136] at least one second layer stack, wherein the second layer stack comprises at least one second electrode, at least one second absorber layer and at least one second layer;
[0137] the second layer stack is applied on top of the first layer stack;
[0138] wherein the first and second layers are selected from the group consisting of a hole transport layer, an electron transport layer, and an absorber layer.
[0139] In the case that the solar cell is a sub-cell of a multi-junction solar cell, it is preferred that the first layer is an absorber layer, particularly preferably an absorber layer from the group consisting of a perovskite layer, an organic absorber layer, a silicon-based absorber layer, a copper indium gallium diselenide (CIGS)-based absorber layer, and a CdTe-based absorber layer. Furthermore, it is preferred that the second layer is an absorber layer, particularly preferably a perovskite layer or an organic absorber layer.
[0140] The present invention further relates to a manufacturing process for a solar cell, particularly preferably the solar cell according to the present invention, wherein one or more passivation layers are produced or applied by means of physical vapor deposition (PVD), particularly preferably thermal evaporation.
[0141] The present invention is further explained by the following embodiments and combinations of embodiments resulting from the specified dependencies and cross-references. It is particularly noted that in every instance where a range of embodiments is mentioned, e.g., in connection with a term such as "The solar cell according to one of embodiments 1 to 4," each embodiment within that range is to be explicitly disclosed to the person skilled in the art; that is, the wording of this term is to be understood by the person skilled in the art as a synonym for "The solar cell according to one of embodiments 1, 2, 3, and 4." Furthermore, it is expressly noted that the following series of exemplary embodiments does not constitute the scope of claims, but rather a suitable structured part of the description directed toward general and preferred aspects of the present invention.
[0142] 1. Solar cell, wherein the solar cell is a single solar cell or a subcell of a multiple solar cell, comprising the solar cell
[0143] an absorber layer,
[0144] one or more passivation layers,
[0145] an electron transport layer conductively connected to at least one negative electrode of the solar cell,
[0146] a hole transport layer conductively connected to at least one positive electrode of the solar cell;
[0147] wherein one or more passivation layers are a compound of formula (A)
[0148] RI
[0149] R« R',
[0150] R4 -- Q : R;
[0151] R
[0152] Hu (A)
[0153]
[0154] include;
[0155] wobei R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind;
[0156] wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Sauerstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkyl koxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1, -NHCOR', -NHCOOR 1 , -NHCONHR 1 , alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected; and / or
[0157] wherein one or more passivation layers are a compound of formula (B)
[0158]
[0159] include;
[0160] wobei RT, R2‘, R3‘, und R4‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , - NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind;
[0161] wobei R9‘, R10‘, R11‘, R12‘, R13‘ und R14‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Sauerstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1, - NHCOR', -NHCOOR 1 , -NHCONHR 1 , Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected.
[0162] Die Solarzelle nach Ausführungsform 1, wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, C5-C30 Cycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1 , Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected.
[0163] Die Solarzelle nach Ausführungsform 1 oder 2, wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, Cs-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, C5-C30 Cycloalkylkoxy, C5-C30 Heterocycloalkyloxy, C6-C30 Aryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1, -NHCOOR', -NHCONHR', and Acyl, where each of these groups can be substituted, are selected.
[0164] 4. The solar cell according to one of embodiments 1 to 3, wherein R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, Cs-Csoheteroarylalkyl, Cs-Csoheteroarylalkenyl, C5-C30 heteroarylheteroalkyl, hydroxy, C1-C30 hydroxyalkyl, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups being substitutable, are selected.
[0165] 5. The solar cell according to one of embodiments 1 to 4, wherein R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, each of these groups may be substituted.
[0166] 6. The solar cell according to one of embodiments 1 to 5, wherein R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, secbutyl, tert-butyl, phenyl, and benzyl, and particularly preferably from the group consisting of hydrogen, methyl, and ethyl.
[0167] 7. Die Solarzelle nach einer der Ausführungsformen 1 bis 6, wobei R9‘, R10‘, R1T, R12‘, R13‘ und R14‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, Cs-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Cs-CaoAryloxy, Ce-CaoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino,Sulfinylamino, -COOH, -COR', -COOR', -CONHR', -NHCOR', -NHCOOR', -NHCONHR', alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected.
[0168] The solar cell according to one of embodiments 1 to 7, wherein R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, Ca-Caoalkynyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Caocycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, Cs-Caoaryl, C6-C30 arylalkyl, Cs-Caoarylalkenyl, C6-C30 arylheteroalkyl, C5-C30 heteroaryl, Cs-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 alkenyloxy, C2-C30 alkynyloxy, Cs-Csocycloalkylkoxy, C5-C30 heterocycloalkyloxy, Cs-CaoAryloxy, Ce-CsoArylalkyloxy, phenoxy, benzyloxy, C5-C30 heteroaryloxy, and acyl, where each of these groups can be substituted,are selected.
[0169] The solar cell according to one of embodiments 1 to 8, wherein R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, Cs-Cao cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, C5-C30 heteroarylalkenyl, C5-C30 heteroarylheteroalkyl, hydroxy, C1-C30 hydroxyalkyl, C6-C30 Aryloxy, Cs-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups may be substituted, are selected.
[0170] The solar cell according to one of embodiments 1 to 9, wherein R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, hydroxy, and C1-C30 hydroxyalkyl, each of these groups being substitutable. 11.The solar cell according to one of embodiments 1 to 10, wherein R9', R10', R1T, R12', R13' and R14' are independently selected from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, secbutyl, tert-butyl, phenyl, and benzyl, and particularly preferably from the group consisting of hydrogen, methyl, and ethyl.
[0171] 12. Die Solarzelle nach einer der Ausführungsform 1 bis 11, wobei R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected; where R5, R6, R7, R8, R9 and R10 are hydrogen.
[0172] 13. Die Solarzelle nach einer der Ausführungsform 1 bis 12, wobei RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected; where R9', R10', R1T, R12', R13' and R14' are hydrogen. 14. The solar cell according to one of embodiments 1 to 13, wherein RT, R2 ', R3' and R4' are independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylheteroalkyl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, aryl, arylalkyl, arylalkenyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylheteroalkyl, haloalkyl, haloalkenyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkenyloxy, alkynyloxy, cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino,Sulfonylamino, sulfinylamino, alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected; wherein R5', R6', R7', R8', R9', R10', R1T, R12', R13', and R14' are hydrogen.
[0173] 15. Die Solarzelle nach einer der Ausführungsformen 1 bis 14, wobei R1, R2, R3 und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C30 Alkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, C6-C30 Arylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, Cs-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, C5-C30 Cycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino,Alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected.
[0174] 16. The solar cell according to one of embodiments 1 to 15, wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 arylalkyl, C6-C30 arylalkenyl, C6-C30 arylheteroalkyl, C5-C30 heteroaryl, Cs-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 alkenyloxy, C2-C30 alkynyloxy, Cs-Csocycloalkylkoxy, C5-C30 heterocycloalkyloxy, C6-C30 aryloxy, C6-C30 arylalkyloxy, phenoxy, benzyloxy, C5-C30 heteroaryloxy, and acyl, where each of these groups may be substituted, are selected.
[0175] The solar cell according to one of embodiments 1 to 16, wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-C30 heteroalkenyl, C5-C30 cycloalkyl, C5-C30 cycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, Cs-Csoheteroarylalkyl, Cs-Csoheteroarylalkenyl, C5-C30 heteroarylheteroalkyl, hydroxy, C1-C30 hydroxyalkyl, Ce-Csoaryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups can be substituted, are selected.
[0176] The solar cell according to one of embodiments 1 to 17, wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, Cs-Cso cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, Cs-Cso heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, wherein each of these groups may be substituted.
[0177] The solar cell according to embodiment 1 to 18, wherein R1, R2, R3 and R4 are independently selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably from the group consisting of chlorine and bromine, wherein R1, R2, R3 and R4 are particularly preferably bromine.
[0178] The solar cell according to one of embodiments 1 to 19, wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, methyl, ethyl isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, preferably from the group consisting of hydrogen, methyl, ethyl isopropyl, secbutyl, tert-butyl, phenyl, and benzyl, and particularly preferably from the group consisting of hydrogen, methyl, ethyl, phenyl, and benzyl.
[0179] Die Solarzelle nach einer der Ausführungsform 1 bis 20, wobei RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘, bevorzugt RT, R2‘, R3‘ und R4‘, unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl,Acylamino, Arylamino, Sulphonylamino, Sulfinylamino, -COOH, -COR, 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1 , Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected.
[0180] Die Solarzelle nach einer der Ausführungsform 1 bis 21, wobei RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘, bevorzugt RT, R2‘, R3‘ und R4‘, unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, Cs-CsoCycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5-CsoHeteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, und Acyl,where each of these groups can be substituted, are selected.
[0181] The solar cell according to one of embodiments 1 to 22, wherein RT, R2', R3', R4', R5', R6', R7' and R8', preferably RT, R2', R3' and R4', independently of one another, from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 heteroalkyl, C3-Csoheteroalkenyl, C5-C30 cycloalkyl, Cs-Csocycloalkenyl, C5-C30 cycloalkylalkyl, C5-C30 cycloalkylheteroalkyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heterocycloalkylalkyl, C5-C30 heterocycloalkylheteroalkyl, C5-C30 heteroaryl, C5-Csoheteroarylalkyl, Cs-Csoheteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, Hydroxy, C1-C30 Hydroxyalkyl, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, and C5-C30 Heteroaryloxy, each of these groups being substitutable, are selected.The solar cell according to one of embodiments 1 to 23, wherein RT, R2', R3', R4', R5', R6', R7' and R8', preferably R1', R2', R3' and R4', are independently selected from the group consisting of hydrogen, halogen, C1-C30 alkyl, C2-C30 heteroalkyl, C5-C30 cycloalkyl, C5-Cso cycloalkenyl, C5-C30 heterocycloalkyl, C5-C30 heterocycloalkenyl, C5-C30 heteroaryl, C5-Cso heteroarylalkyl, hydroxy, C1-C30 hydroxyalkyl, each of these groups may be substituted.
[0182] The solar cell according to embodiment 1 to 24, wherein R1', R2', R3', R4', R5', R6', R7' and R8', preferably RT, R2', R3' and R4', are independently selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably from the group consisting of chlorine and bromine, wherein R1, R2, R3 and R4 are particularly preferably bromine.
[0183] The solar cell according to one of embodiments 1 to 25, wherein RT, R2', R3', R4', R5', R6', R7' and R8', preferably RT, R2', R3' and R4', independently of one another from the group consisting of hydrogen, methyl, ethyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 2-methyl-hexyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, and benzyl, preferably from the group consisting of hydrogen, methyl, ethyl, isopropyl, sec-butyl, tert-butyl, phenyl, and benzyl, particularly preferably from the The group consists of hydrogen, methyl, ethyl, phenyl and benzyl.
[0184] The solar cell according to one of embodiments 1 to 6, 12 or 15 to 18, wherein one or more passivation layers are a compound of formula (A-1)
[0185] Ar
[0186] AI " 1 ] .. • Ar
[0187]
[0188] Ar Formula (A-1)
[0189] comprising, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, and isoquinolyl, each of these groups being substitutable. The solar cell according to one of embodiments 1 to 6, 12, or 15 to 18, wherein one or more passivation layers comprise a compound of formula (A-2)
[0190]
[0191] include, where X is selected from the group consisting of CI, Br, I, F, CN, NCh.CHs, CF3, OCH3, and SO3H.
[0192] The solar cell according to one of embodiments 1 to 6, 12 or 15 to 18, wherein one or more passivation layers are a compound of formula (A-3)
[0193]
[0194] Formula (A-3)
[0195] include.
[0196] The solar cell according to one of embodiments 1, 7 to 11, 13 to 14 or 21 to 24, wherein one or more passivation layers are a compound of formula (B-1)
[0197]
[0198] Formula (B-1)
[0199] comprising, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl, each of these groups may be substituted.
[0200] The solar cell according to one of embodiments 1, 7 to 11, 13 to 14 or 21 to 24, wherein one or more passivation layers are a compound of formula (B-2)
[0201]
[0202] include, where X is selected from the group consisting of CI, Br, I, F, CN, NO2.CH3, CF3, OCH3, and SO3H.
[0203] The solar cell according to one of embodiments 1, 7 to 11, 13 to 14 or 21 to 24, wherein one or more passivation layers are a compound of formula (B-3)
[0204]
[0205] Formula (B-3)
[0206] include.
[0207] The solar cell according to one of embodiments 1 to 32, wherein the one or more passivation layers have a layer thickness of 0.1 to 200 nm, preferably of 1 to 50 nm.
[0208] The solar cell according to one of embodiments 1 to 33, wherein the one or more passivation layers are produced or applied by means of physical vapor deposition (PVD), preferably thermal evaporation.
[0209] The solar cell according to one of embodiments 1 to 34, wherein the one or more passivation layers further comprise a material selected from the group consisting of an alkali metal halide, an alkaline earth metal halide, an alkylammonium halide, an arylalkylammonium halide, a diamino halide, and mixtures of two or more thereof, preferably selected from the group consisting of an alkali metal fluoride, an alkaline earth metal fluoride, an alkylammonium iodide, an arylalkylammonium iodide, a diaminoalkyl dihydroiodide, and mixtures of two or more thereof, preferably selected from the group consisting of lithium fluoride, phenethylammonium iodide (PEAI), 1,3-diaminopropane dihydroiodide (PDADI), n-butylammonium iodide (BAI), and a mixture of two or more thereof. 36.The solar cell according to one of embodiments 1 to 35, wherein the electron transport layer comprises one or more inorganic and / or organic materials, preferably one or more organic materials.
[0210] 37. The solar cell according to embodiment 36, wherein the one or more organic materials are selected from the group consisting of unsubstituted or substituted fullerenes, NDI (naphthalene diimide), naphthalene diimide-based polymers, PDI (perylene diimide), perylene diimide-based polymers, TDI (terylene diimide), terylene diimide-based polymers, indacene dithiophene-based compounds, anthracene-based compounds, tetracene-based compounds, pentacene-based compounds, or mixtures thereof, particularly preferably from the group consisting of C60, C70, PCBM (6,6-phenyl-C61-butyric acid methyl ester), PDI (perylene diimide) and mixtures thereof.
[0211] 38. The solar cell according to embodiment 36 or 37, wherein the one or more inorganic materials comprise one or more metal oxides, preferably one or more metal oxides selected from the group consisting of tin oxide, zinc oxide, titanium oxide, aluminum oxide, zirconium oxide, indium oxide and mixtures thereof.
[0212] 39. The solar cell according to embodiment 38, wherein one or more metal oxides are doped with an element E, wherein E is an element of group I to III of the periodic table, preferably an element of group I to II, particularly preferably selected from the group consisting of H, Na, Li, and K, particularly preferably H.
[0213] 40. The solar cell according to one of embodiments 1 to 39, wherein the electron transport layer has a layer thickness of 0.1 nm to 500 nm, preferably of 10 nm to 200 nm.
[0214] 41. The solar cell according to one of embodiments 1 to 40, wherein the electron transport layer is produced by means of a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of sputtering, electron beam evaporation, and physical vapor deposition.
[0215] (PVD), rotary coating, doctor blade coating, and inkjet printing, chemical vapor deposition (CVD), laser beam evaporation (PLD) and combinations of two or more of these processes.
[0216] 42. The solar cell according to one of embodiments 1 to 41, wherein the hole transport layer comprises one or more polymers, preferably one or more polymers selected from the group consisting of PTAA (poly-[bis-(4-phenyl)-(2,4,6-trimethylphenyl)-amine]), PEDOT:PSS (poly(ethylenedioxythiophene):poly(styrenesulfonate)), poly-TPD (poly[N,N'-bis(4-butylphenyl)-N,N-bis(phenyl)benzidine]), and P3HT (poly(3-hexylthiophene)).
[0217] 43. The solar cell according to one of embodiments 1 to 42, wherein the hole transport layer comprises one or more materials based on small molecules, preferably Spiro-OMeTAD (2,27,7'-Tetraakis-(N,N-Di-4-methoxyphenylamino)-9,9'spirobifluorene).
[0218] 44. The solar cell according to one of embodiments 1 to 43, wherein the hole transport layer comprises one or more self-organized layers.
[0219] 45. The solar cell according to embodiment 44, wherein the one or more self-assembled layers comprise at least one molecule of formula (I) of reference RF1,
[0220] where L is a connecting fragment, A is an anchor group and HTF (“hole transporting fragment”) is a hole-conducting fragment selected from one of the formulas (II) or (III) of reference RF1,
[0221] wherein Z and D are homocyclic or at least one of Z or D comprises a heteroatom, the heteroatom preferably selected from the group N, S, O and Si, and wherein Z is a Cs- or Cs-substituted or unsubstituted aromatic group, D is N or a Cs- or Cs-aromatic group, wherein two carbon atoms of the aromatic group D are each bonded to one of the two aromatic groups Z to form a tricycloundecane, a tricyclotridecane or a tricyclotetradecane derivative; or R is independently selected from the group consisting of H, Ci to Cw alkyl; C2- to Cw-Alkenyl, C3- to C2o-Cycloalkyl, C3- to Cs-Heterocycloalkyl, Alkoxy, Aryloxy, Alkylthio, Arylthio, Amino, Amido, Ester, Carboxylic acid, Dialkoxydiphenylamine, Carbamate, Urea, Ketone, Aldehyde, Cyano, Nitro, Halogen, Cycloalkylalkyl, and Heterocycloalkylalkyl, has been selected.
[0222] 46. The solar cell according to embodiment 45, wherein the connecting fragment L is selected from the group consisting of Ci- to Cg-alkylenes, C4- to C2o-arylenes, C4- to C20-heteroarylenes, C4- to C2o-alkylarylenes, C4- to C2o-heteroalkylarylenes, wherein the heteroatoms are preferably selected from O, N, S, Se, Si, and wherein the aforementioned alkylenes, arylenes, heteroarylenes, alkylarylenes, heteroalkylarylenes, and heteroalkylarylenes, if they comprise three or more carbon atoms, may be linear, branched, or cyclic. 47. The solar cell according to embodiment 45 or 46, wherein the anchor group A is selected from the group consisting of phosphonic acid, phosphoric acid, sulfuric acid, sulfonic acid, carboxylic acid, and siloxanes.
[0223] 48. The solar cell according to one of embodiments 45 to 47, wherein the hole-conducting fragment HTF is selected from the group consisting of formulas (IV) to (XIX) of reference RF1.
[0224] 49. The solar cell according to one of embodiments 44 to 48, wherein the one or more self-assembled layers are selected from the group consisting of 2PACz ([2-(9H-carbazol-9-yl)ethyl]phosphonic acid), MeO-2PACz ([2-(3,6-dimethoxy-9H-carbazol-9-yl)ethyl]phosphonic acid) and ((4-(9H-carbazol-9-yl)butyl)phosphonic acid.
[0225] 50. The solar cell according to one of embodiments 1 to 49, wherein the hole transport layer comprises one or more inorganic materials, preferably one or more inorganic materials selected from the group consisting of copper oxide, nickel oxide, copper iodide, copper thiocyanate, and mixtures of two or more, particularly preferably from the group consisting of copper oxide, nickel oxide, and mixtures thereof.
[0226] 51. The solar cell according to one of embodiments 44 to 50, wherein the hole transport layer comprises one or more self-organized layers and one or more inorganic materials.
[0227] 52. The solar cell according to one of embodiments 1 to 51, wherein the hole transport layer is doped with a material selected from the group consisting of Li-TFSI (lithium bis(trifluoromethanesulfonyl)imide), TBP (4-tert-butylpyridine), FK20 (tris[2-2(1H-pyrazol-1-yl)-4-tert-butylpyridine]-cobalt(II I), tris[bis(trifluoromethanesulfonyl)imide]), F4-TCNQ (2, 3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinoldimethane) and mixtures of two or more thereof.
[0228] 53. The solar cell according to one of embodiments 1 to 52, wherein the hole transport layer has a layer thickness of 0.1 nm to 500 nm, preferably of 2 nm to 200 nm.
[0229] 54. The solar cell according to one of embodiments 1 to 53, wherein the hole transport layer is produced by a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of sputtering, electron beam evaporation, physical vapor deposition (PVD), rotary coating, doctor blade coating, dip coating and inkjet printing, and combinations of two or more of these processes.
[0230] 55. The solar cell according to one of embodiments 1 to 54, wherein the absorber layer is a perovskite layer.
[0231] 56. The solar cell according to embodiment 55, wherein the perovskite layer has a layer thickness of 50 nm to 10 pm, preferably of 500 nm to 1 pm.
[0232] 57. The solar cell according to one of embodiments 1 to 56, wherein the perovskite layer is produced by a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of physical vapor deposition (PVD), rotary coating, doctor blade coating, inkjet printing, spray coating, slot die coating, roller coating, gravure printing, chemical vapor deposition (CVD), power laser deposition (PLD), sputtering and combinations of two or more of these processes.
[0233] 58. The solar cell according to one of embodiments 1 to 57, wherein the absorber layer comprises an organic absorber.
[0234] 59. The solar cell according to embodiment 58, wherein the organic absorber is selected from the group consisting of polymers, dendrimers, and macromers, preferably selected from the group consisting of PW poly(phenylvinyl), CN-PPV, MEH-PPV, phthalocyanine, polyacetylene, and mixtures thereof.
[0235] 60. The solar cell according to embodiment 58 or 59, wherein the absorber layer has a layer thickness of 800 nm to 10 pm, preferably from 1 pm to 5 pm.
[0236] 61. The solar cell according to one of embodiments 1 to 60, wherein the absorber layer is produced by a deposition process based on a low-pressure or vacuum coating process, preferably a deposition process selected from the group consisting of physical vapor deposition (PVD), rotary coating, doctor blade coating, inkjet printing, spray coating, slot die coating, roller coating, gravure printing, chemical vapor deposition, laser beam evaporation, cathode sputtering and combinations of two or more of these processes.
[0237] The solar cell according to one of embodiments 1 to 61, wherein the solar cell further comprises one or more buffer layers.
[0238] The solar cell according to embodiment 62, wherein the buffer layer comprises a material selected from the group consisting of bathocuproin (BCP), lithium fluoride, magnesium fluoride, polyfluorene, and mixtures of two or more thereof.
[0239] The solar cell according to embodiment 62 or 63, wherein the buffer layer comprises one or more inorganic nanoparticles, preferably inorganic nanoparticles selected from the group consisting of aluminium oxide, zinc oxide, titanium oxide, nickel oxide, lead sulfide and mixtures of two or more.
[0240] The solar cell according to one of embodiments 1 to 64, wherein one or more passivation layers are arranged between the absorber layer and the electron transport layer.
[0241] The solar cell according to one of embodiments 1 to 65, wherein the electron transport layer is arranged between the absorber layer and the one or more passivation layers.
[0242] The solar cell according to one of embodiments 1 to 66, wherein one or more passivation layers are arranged between the absorber layer and the hole transport layer.
[0243] The solar cell according to one of embodiments 1 to 67, wherein the solar cell further comprises a substrate.
[0244] The solar cell according to embodiment 68, wherein the one or more passivation layers are arranged over 60 to 100%, preferably over 80 to 100%, particularly preferably over 90 to 100%, particularly preferably over 95 to 100%, particularly preferably over 99 to 100% of the substrate length. 70. The solar cell according to one of embodiments 1 to 69, wherein the one or more passivation layers and the electron transport layer are applied simultaneously by co-evaporation.
[0245] 71. The solar cell according to one of embodiments 1 to 70, wherein the solar cell is a subcell of a multi-junction solar cell, and wherein the multi-junction solar cell comprises at least one first layer stack, wherein the first layer stack comprises at least one substrate, at least one first electrode and at least one first layer; at least one second layer stack, wherein the second layer stack comprises at least one second electrode, at least one second absorber layer and at least one second layer;
[0246] the second layer stack is applied on top of the first layer stack;
[0247] wherein the first and second layers are selected from the group consisting of a hole transport layer, an electron transport layer, and an absorber layer.
[0248] 72. The solar cell according to embodiment 71, wherein the first layer is an absorber layer, preferably an absorber layer from the group consisting of a perovskite layer, an organic absorber layer, a Si-based absorber layer, a copper indium gallium diselenide (CIGS)-based absorber layer and a CdTe-based absorber layer.
[0249] 73. The solar cell according to embodiment 71 or 72, wherein the second layer is an absorber layer, preferably a perovskite layer or an organic absorber layer.
[0250] 74. Manufacturing method of a solar cell, preferably the solar cell according to one of embodiments 1 to 73, wherein the one or more passivation layers are produced or applied by means of physical vapor deposition (PVD), preferably thermal evaporation.
[0251] LITERATURE CITATED:
[0252] - DE 102009025977 A1
[0253] - US 2011 / 0284068 A1
[0254] - WO 2019 / 207029 A 1
[0255] - Yen-Hung Lin et al., „Bandgap-universal passivation enables stable perovskite solar cells with low photovoltage loss“, Science, 384, 767-775 (2024) - Zhengchi Yang et al., "Self-healing and efficient flexible perovskite solar cells enabled by host-guest interaction and a 2S / 3S heterostructure", Journal of Materials Chemistry A: Materials for Energy and Sustainability, 10(42), 22445 (2022)
[0256] Mohammad Mahdi Tavakoli et al., „Adamantanes Enhance the Photovoltaic Performance and Operational Stability of Perovskite Solar Cells by Effective Mitigation of Interfacial Defect States”, Advanced Energy Materials, 8(19), 1800275 (2018)
[0257] Li Tan et al., „Quantitative Surface Passivation Through Drop-on-Demand Inkjet Printing Enables Hghly Efficient Perovskite Solar Cells”, Advanced Energy Materials, 14(27), 2400549 (2024)
[0258] - Qian Zhou et al., “Revealing Steric-Hindrance-Dependent Buried Interface Defect Passivation Mechnism in Efficient and Stable Perovskite Solar Cells with Mitigated Tensile Stress”, Advanced Functional Materials, 32(36), 2205507 (2022)
[0259] - Jose M. Obrero-Perez et al., “Ultrathin Plasma Polymer Passiavation of Perovskite Solar Cells for Improved Stability and Reproducibility”, Advanced Energy Materials, 12(32), 2200812 (2022)
Claims
Patent claims 1. Solar cell, wherein the solar cell is a single solar cell or a subcell of a multiple solar cell, comprising the solar cell an absorber layer, one or more passivation layers, an electron transport layer conductively connected to at least one negative electrode of the solar cell, a perforated transport layer conductively connected to at least one positive electrode of the solar cell; wherein one or more passivation layers are a compound of formula (A) include; wobei R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind; wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Sauerstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1, -NHCOR', -NHCOOR 1 , -NHCONHR 1 , alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, and acyl, each of these groups being substitutable, are selected; and / or wherein one or more passivation layers are a compound of formula (B) RI include; wobei RT, R2‘, R3‘, und R4‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , - NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, und Acyl, wobei jeder dieser Gruppen substituiert sein kann, ausgewählt sind; wobei R9‘, R10‘, R1 T, R12‘, R13‘ und R14‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Sauerstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloal kylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR‘, -COOR‘, -CONHR 1, - NHCOR', -NHCOOR 1 , -NHCONHR 1 , Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected.
2. Die Solarzelle nach Anspruch 1, wobei R5, R6, R7, R8, R9 und R10 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, C1-C30 Alkyl, C2-C30 Alkenyl, C2-C3oAlkynyl, C2-C30 Heteroalkyl, C3-C30 Heteroalkenyl, C5-C30 Cycloalkyl, C5-C30 Cycloalkenyl, C5-C30 Cycloalkylalkyl, C5-C30 Cycloalkylheteroalkyl, C5-C30 Heterocycloalkyl, C5-C30 Heterocycloalkenyl, C5-C30 Heterocycloalkylalkyl, C5-C30 Heterocycloalkylheteroalkyl, Ce-CsoAryl, C6-C30 Arylalkyl, Ce-CsoArylalkenyl, C6-C30 Arylheteroalkyl, C5-C30 Heteroaryl, C5- C30 Heteroarylalkyl, Cs-CsoHeteroarylalkenyl, C5-C30 Heteroarylheteroalkyl, C1-C30 Haloalkyl, C2-C30 Haloalkenyl, Hydroxy, C1-C30 Hydroxyalkyl, C1-C30 Alkoxy, C1-C30 Alkoxyalkyl, C5-C30 Alkoxyaryl, C2-C30 Alkenyloxy, C2-C30 Alkynyloxy, Cs-CsoCycloalkylkoxy, C5-C30 Heterocycloalkyloxy, Ce-CsoAryloxy, Ce-CsoArylalkyloxy, Phenoxy, Benzyloxy, C5-C30 Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1 , Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected.
3. Die Solarzelle nach Ansprüchen 1 oder 2, wobei R1, R2, R3, und R4 unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, -COR 1 , -COOR 1 , -CONHR 1 , - NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl, and Acyl, each of these groups being substitutable, are selected; where R5, R6, R7, R8, R9 and R10 are hydrogen.
4. Die Solarzelle nach einem der Ansprüche 1 bis 3, wobei RT, R2‘, R3‘, R4‘, R5‘, R6‘, R7‘ und R8‘ unabhängig voneinander aus der Gruppe bestehend aus Wasserstoff, Halogen, Alkyl, Alkenyl, Alkynyl, Heteroalkyl, Heteroalkenyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkylheteroalkyl, Heterocycloalkyl, Heterocycloalkenyl, Heterocycloalkylalkyl, Heterocycloalkylheteroalkyl, Aryl, Arylalkyl, Arylalkenyl, Arylheteroalkyl, Heteroaryl, Heteroarylalkyl, Heteroarylalkenyl, Heteroarylheteroalkyl, Haloalkyl, Haloalkenyl, Hydroxy, Hydroxyalkyl, Alkoxy, Alkoxyalkyl, Alkoxyaryl, Alkenyloxy, Alkynyloxy, Cycloalkylkoxy, Heterocycloalkyloxy, Aryloxy, Arylalkyloxy, Phenoxy, Benzyloxy, Heteroaryloxy, Amino, Alkylamino, Aminoalkyl, Acylamino, Arylamino, Sulfonylamino, Sulfinylamino, -COOH, - COR 1 , -COOR 1 , -CONHR 1 , -NHCOR 1 , -NHCOOR 1 , -NHCONHR 1, Alkoxycarbonyl, Alkylaminocarbonyl, Sulfonyl, Alkylsulfonyl, Alkylsulfinyl, Arylsulfonyl, Arylsulfinyl, Aminosulfonyl and Acyl, each of these groups may be substituted, are selected; where R9', R10', R1T, R12', R13' and R14' are hydrogen.
5. The solar cell according to one of claims 1 to 3, wherein one or more passivation layers are a compound of formula (A-1) Ar As -7”' | . .. ■ -- Ai Ar Formula (A-1) comprising, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, and isoquinolyl, each of these groups being substitutable.
6. The solar cell according to one of claims 1 to 3, wherein one or more passivation layers are a compound of formula (A-2) Formula (A-2) include, where X is selected from the group consisting of CI, Br, I, F, CN, NCh.CHs, CF3, OCH3, and SO3H.
7. The solar cell according to claim 1 or 4, wherein one or more passivation layers are a compound of formula (B-1) Ar Formula (B-1) comprising, wherein Ar is selected from the group consisting of thienyl, pyridinyl, phenyl, naphthyl, furyl, pyrimidyl, pyrazinyl, thiazolyl, imidazolyl, oxazolyl, indolyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl, each of these groups may be substituted.
8. The solar cell according to claim 1 or 4, wherein one or more passivation layers are a compound of formula (B-2) Formula (B-2) include, where X is selected from the group consisting of CI, Br, I, F, CN, NCh.CHs, CF3, OCH3 and SO3H.
9. The solar cell according to any one of claims 1 to 8, wherein the hole transport layer comprises one or more self-organized layers, particularly preferably one or more self-organized layers selected from the group consisting of 2PACz ([2-(9H-carbazol-9-yl)ethyl]phosphonic acid), MeO-2PACz ([2-(3,6-dimethoxy-9H-carbazol-9-yl)ethyl]phosphonic acid) and ((4-(9H-carbazol-9-yl)butyl)phosphonic acid.
10. The solar cell according to any one of claims 1 to 9, wherein the absorber layer is a perovskite layer.
11. The solar cell according to one of claims 1 to 10, wherein one or more passivation layers are arranged between the absorber layer and the electron transport layer.
12. The solar cell according to one of claims 1 to 11, wherein the electron transport layer is arranged between the absorber layer and the one or more passivation layers.
13. The solar cell according to any one of claims 1 to 12, wherein the solar cell is a subcell of a multi-junction solar cell, and wherein the multi-junction solar cell comprises at least one first layer stack, wherein the first layer stack comprises at least one substrate, at least one first electrode and at least one first layer; at least one second layer stack, wherein the second layer stack comprises at least one second electrode, at least one second absorber layer and at least one second layer; wherein the second layer stack is applied to the first layer stack; wherein the first and the second layers are selected from the group consisting of a hole transport layer, an electron transport layer, and an absorber layer.
14. Manufacturing process of a solar cell, wherein one or more passivation layers are produced or applied by means of physical vapor deposition (PVD).
Citation Information
Patent Citations
Solar cell and manufacturing process of a solar cell
DE102009025977A1
Passivation methods and apparatus for achieving ultra-low surface recombination velocities for high-efficiency solar cells
US20110284068A1
Hole-transporting self-organised monolayer for perovskite solar cells
WO2019207029A1
Crystal defects mitigating agents for high power conversion efficiency and stability of perovskyte photovoltaic devices
US20210054288A1