Organic Heterocycles for Photoelectric Devices

Description

[0001] The present invention relates to organic heterocycles for use in electronic devices, in particular in organic photoelectric devices, and to electronic devices, in particular organic photoelectric devices, containing these heterocyclic compounds.

[0002] Heterocyclic compounds are frequently used as photosensitizers in organic optical detectors. Heterocyclic compounds that can be used in optical detectors are known from US 2020 / 19467 A1, CN 110964007 A, EP 3026722 A1, EP 3243822 A1, EP 3473622 A1, EP 3757108 A1, EP 3770163 A1, US 2019 / 131541 A1 and EP 3848374 A1. Compounds according to the present invention are not disclosed.

[0003] In general, there is still room for improvement with these heterocyclic compounds, for example for use as photosensitizers, especially with regard to lifetime, but also with regard to efficiency and the operating voltage of the device.

[0004] The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic optical detector, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device.

[0005] In particular, the object of the present invention is to provide connections that lead to a long service life, good efficiency and low operating voltage.

[0006] Furthermore, the compounds should exhibit excellent processability, and in particular, good solubility.

[0007] A further object of the present invention can be seen as providing compounds suitable for use in an organic optical detector, in particular as photosensitizers. In particular, it is an object of the present invention to provide photosensitizers suitable for infrared, red, green, or blue optical detectors, preferably for green optical detectors.

[0008] Another task can be seen as providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality.

[0009] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0010] Surprisingly, it was found that certain compounds, described in more detail below, solve this problem, are very well suited for use in electronic devices, and lead to organic optical detectors that exhibit excellent properties, particularly with regard to lifetime, efficiency, and operating voltage. These compounds, as well as electronic devices, especially organic optical detectors containing such compounds, are therefore the subject of the present invention.

[0011] The present invention relates to a compound comprising at least one structure of formula (I), preferably a compound according to formula (I), where the following applies to the symbols used: Ar a< is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more Ar or R a< residues; Ar b< is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more Ar or R b< residues; Zist, in each occurrence, is either an alkenyl group with 2 to 40 carbon atoms, wherein the alkenyl group may be substituted with one or more R d< substituents, wherein one or more non-adjacent CH 2 groups may be replaced by R d< C=CR d< , C=C, Si(R d< ) 2 , C=O, C=S, C=Se, C=NR, C(=O)O, C(=O)NR d< , NR, P(=O)(R d< ), O, S, SO or SO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms,which can each be substituted by one or more R< d< residues; the group can form a ring system with another group, for example a group R or R< c<; provided that the group Z has at least two CN groups; Y< 1< is the same or different in each occurrence O, S, Se, Te, NAr, NR, C(R)2, Ge(R)2, Si(R)2, preferably O, S, Se, Te, NAr, particularly preferably S or Se; Y 2< is, in each occurrence, the same or different bond, O, S, Se, Te, NAr, NR e< , BAr, BR e< , C(R e< ) 2 , Ge(R e< ) 2 , Si(R e< ) 2 , CR e< =CR e< , C=NR e< , S=O, SO 2 , preferably a bond, C(R e< ) 2 , O, S, NAr, particularly preferably C(R e< ) 2 ; List, in each occurrence the same or different, a compound group, preferably a bond, C(R) 2 , O, S, NR, NAr, C(=O), BAr, B(R), Si(R) 2 , C=NR, C=C(R) 2 , S=O, SO 2 , P(R), P(=O)R, CR=CR or an aromatic or heteroaromatic ring system with 5 to 40,preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more R groups, particularly preferably a bond, C(R) 2 , O, S, NAr, NR, CR=CR or an ortho-linked arylene or heteroarylene group with 5 to 14 aromatic ring atoms, most preferably a bond, C(R) 2 , O, S, NAr or NR; Ar is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted by one or more R groups; in this case, the group Ar can form a ring system with at least one group Ar, R, Ra< , Rb< , Rc< , Rd< , Re< or another group; R, R a< , R b< , R c< , R d< , Re< is the same or different in each occurrence H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar') 2 , N(R 1< ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1< ) 2 , C(Ar') 3 , C(R 1< ) 3 , Si(Ar') 3 , Si(R 1< ) 3 , B(Ar') 2 , B(R 1< ) 2 , C(=O)Ar', C(=O)R 1< , P(=O)(Ar') 2 , P(=O)(R 1< ) 2 , P(Ar') 2 ,P(R 1< ) 2 , S(=O)Ar', S(=O)R', S(=O) 2 Ar', S(=O) 2 R 1< , OSO 2 Ar', OSO 2 R 1< , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or an alkenyl or alkynyl group with 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 20 C atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may each be substituted with one or more R 1< residues, wherein one or more non-adjacent CH 2 groups are replaced by R 1< C=CR 1< , C=C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , C(=O)O, C(=O)NR 1< , NR 1< , P(=O)(R 1< ), Se, Te, NAr', BR 1< , Ge(R 1< ) 2 , O, S, SO or SO 2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 1< residues, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms,which may be substituted by one or more R1< groups, or an arylthio or heteroarylthio group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R1< groups, or a diarylamino, arylheteroarylamino, diheteroarylamino group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R1< groups, or an aralkyl or heteroarylalkyl group with 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group, which may be substituted by one or more R1< groups; two R, Ra<, Rb<, Rc<, Rd<, Re< groups may also form a ring system with each other or with another group; Ar' is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more R 1< residues; in this case, two Ar' residues bonding to the same C atom, Si atom, N atom, P atom or B atom mayalso be bridged by a single bond or a bridge selected from B(R 1< ), C(R 1< ) 2 , Si(R 1< ) 2 , C=O, C=NR 1< , C=C(R 1< ) 2 , O, S, S=O, SO 2 , N(R 1< ), P(R 1< ) and P(=O)R', together; R 1< is the same or different in each occurrence: H, D, F, Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2< ) 2 , C(=O)Ar", C(=O)R 2< , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B(R 2< ) 2 , C(Ar") 3 , C(R 2< ) 3 , Si(Ar") 3 , Si(R 2< ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 C atoms or an alkenyl group with 2 to 40 C atoms, each with one or more R substituents 2< can be substituted, wherein one or more non-adjacent CH 2 groups can be replaced by R 2< C=CR 2< , C=C, Si(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , C(=O)O, C(=O)NR 2< , NR 2< , P(=O)(R 2< ), O, S, SO or SO 2 and wherein one or more H atoms can be replaced by D, F, Cl, Br, I,CN or NO₂ may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R₂< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R₂< groups, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R₂< groups, or a combination of these systems; wherein two or more, preferably adjacent, R₁< groups may form a ring system together; wherein one or more R₁< groups may form a ring system with a further part of the compound; Ar" is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which may be substituted with one or more R 2< residues; in this case, two Ar" residues attached to the same C atom,Si atom, N atom, P atom or B atom bond, also by a single bond or a bridge, selected from B(R 2< ), C(R 2< ) 2 , Si(R 2< ) 2 , C=O, C=NR 2< , C=C(R 2< ) 2 , O, S, S=O, SO 2 , N(R 2< ), P(R 2< ) and P(=O)R 2< , be bridged to each other; R 2< is selected, in each instance, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon residue with 1 to 20 C atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I, or CN, and which may be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms. Two or more, preferably adjacent, substituents R 2< may form a ring system together.

[0012] The Z group can represent an alkenyl group with 2 to 40 carbon atoms, either identically or differently in each occurrence. This group can be straight-chain, cyclic, or branched, with branched groups containing at least 3 carbon atoms and cyclic groups at least 4. Cyclic groups may also contain one or more heteroatoms.

[0013] According to the invention, group Z comprises at least two CN groups. Structures or compounds of formula (I) are preferred in which group Z comprises two CN groups bonded to the same carbon atom.

[0014] Furthermore, structures or compounds of formula (I) are particularly preferred in which the at least two CN groups of group Z are conjugated throughout with the 5-ring comprising group Y 1<.

[0015] The term "conjugation" or "conjugated" is widely known in the scientific community, so reference is made to it here. A complete conjugation of the at least two CN groups of group Z is formed as soon as alternating double and single bonds exist between the at least two CN groups of group Z and the 5-membered ring comprising group Y<. Further linkage between the aforementioned conjugated groups, for example via an S, N, or O atom or a carbonyl group, does not impair conjugation.

[0016] Preferred embodiments of the groups Ar a< , Ar b< , R c< , R d< , Y 1< , Y 2< and L result in particular from structures or connections described in the prior art.

[0017] Structures or compounds similar to those present with reference to the groups Ar a< , Ar b< , R c< , R d< , Y 1< , Y 2< and L are disclosed, among others, in European patent application EP 3848374 A1, filed with the European Patent Office on 13 January 2021 under application number EP 21151295.9, of which this publication is incorporated by reference for disclosure purposes.

[0018] The structure of formula (I) of the compounds set out in EP 3848374 A1 differs from the present compounds, in particular by group Z, which is not disclosed in EP 3848374 A1, so that preferred structures or compounds similar to the present ones with reference to groups Ar a< , Ar b< , R c< , R d< , Y 1< , Y 2< and L result from the partial element of formula set out in formula (I) of EP 3848374 A1 to be replaced by group Z.

[0019] Under the conditions set out above, namely the replacement of the substructure comprising residues Ar 3< and R 1< set out below and further detailed in EP 3848374 A1 by group Z, the structures detailed in EP 3848374 A1 are in particular according to formula (1) (see EP 3848374 A1, page 3, paragraph

[0009] ), formula (2A) (see EP 3848374 A1, page 4, paragraph

[0011] ), formula (2A-1) (see EP 3848374 A1, page 5, paragraph

[0013] ), formula (2A-2) (see EP 3848374 A1, page 5, paragraph

[0014] ), formula (2B) (see EP 3848374 A1, page 6, paragraph

[0016] ), formula (2B-1) (see EP 3848374 A1, page 6, paragraph

[0019] , formula (2B-2) (see EP 3848374 A1, page 7, paragraph

[0020] , formula (2C) (see EP 3848374 A1, page 7, paragraph

[0022] , formula (2C-1) (see EP 3848374 A1, page 8, paragraph

[0026] , formula (2C-2) (see EP 3848374 A1, page 9, paragraph

[0027] , formula (2D) (see EP 3848374 A1, page 9, paragraph

[0029] , formula (2D-1) (see EP 3848374 A1, page 10, paragraph

[0032] , formula (2D-2) (seeEP 3848374 A1, page 10, paragraph

[0034] , formula (2E) (cf. EP 3848374 A1, page 11, paragraph

[0035] , formula (2E-1) (cf. EP 3848374 A1, page 12, paragraph

[0038] , formula (2E-2) (cf. EP 3848374 A1, page 12, paragraph

[0039] , inserted into the present application for disclosure purposes by reference thereto.

[0020] Particularly preferred structures will be explained in more detail later. These are preferred over those presented previously.

[0021] In a preferred embodiment of the invention, Z is an alkenyl group with 2 to 10 carbon atoms, preferably with 2 to 6 carbon atoms, and particularly preferably with 2 to 4 carbon atoms, which may be substituted with one or more R<d> groups, wherein at least two CN groups are bonded to the alkenyl group; the group may form a ring system with a R or R<c group. Particularly preferred is Z an alkenyl group with 2 carbon atoms, which is substituted with one R<d> group and two CN groups, wherein the two CN groups are preferably bonded to the same carbon atom.

[0022] Furthermore, it may be provided that the group Z represents or comprises a substructure of formula (Z-1) or (Z-2), preferably represents, where R d< and R 1< have the meaning mentioned above, especially for formula (I), the dashed bond represents the attachment point and the following also applies: Xist O, S or Se, preferably O or S and particularly preferably O; pist 0, 1 or 2, preferably 0 or 1 and particularly preferably 1.

[0023] Preferably, the substructure of formula (Z-1) or (Z-2) is conjugated throughout with the 5-membered ring comprising the group Y 1<. Here, R d< in formula (Z-1) preferably represents H or D.

[0024] For formula (Z-2) the following is preferred: Rd, which is bonded to the non-cyclic alkenyl group in formula (Z-2), is preferably the same or different in each occurrence H, D, or an alkyl group with 1 to 5 carbon atoms, particularly preferably H, D, or methyl, and most preferably H or D. Rd, which is bonded to the five-membered ring in formula (Z-2), is preferably H, D, CN, F, an alkyl group with 1 to 5 carbon atoms, or a phenyl group, which may also be substituted by one or more preferably non-aromatic R1 groups. This Rd is preferably H, D, methyl, or CN.

[0025] The groups R1< bonded to the five-membered ring in formula (Z-2) are, in each occurrence, either identical or different: H, D, an alkyl group with 1 to 5 carbon atoms, or a phenyl group, which may also be substituted by one or more preferably non-aromatic R1< groups. The two R1< groups may also form a ring system together. Preferably, these groups R1< are, in each occurrence, identical or different: an alkyl group with 1 to 4 carbon atoms, in particular methyl groups.

[0026] Preferred embodiments of formula (Z-2) are the structures of the following formulas (Z-2') and (Z-2"), wherein these groups may also be partially or completely deuterated, where the dashed bond represents the binding site, R<d> stands for H, D, Methyl or CN, and R<< stands for H, D or Methyl, in particular Methyl, whether the same or different at each occurrence.

[0027] Preferred embodiments of formula (Z-2) are the structures of the following formulas (Z-2a) to (Z-2d), wherein these groups may also be partially or completely deuterated, where the dashed line represents the point of attachment.

[0028] The structures or connections of formula (I) can comprise one, two, three, four or more substructures of formula (Z-1).

[0029] In a preferred embodiment, it may be provided that the compounds according to the invention comprise a structure of formula (II) or (IIa), wherein the compounds according to the invention may particularly preferably be selected from the compounds of formulas (II) or (IIIa), wherein the symbols and indices Ar a< , Ar b< , R c< , R d< , Y 1< , Y 2< , L, R 1< , X and p have the meanings given above, particularly for formula (I), and R d< in formula (II) and in formula (IIa) preferably represents H or D at the non-cyclic alkenyl group, and in formula (IIa) R d< in the five-membered ring preferably represents methyl or CN. Furthermore, X in formula (IIa) preferably represents O or S, particularly preferably O, the explicitly drawn R 1< in formula (IIa) preferably represents optionally deuterated methyl, and the index p in formula (IIa) preferably represents 1.

[0030] An aryl group according to this invention contains 6 to 40 carbon atoms; a heteroaryl group according to this invention contains 2 to 40 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic compounds linked together by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.

[0031] An electron-deficient heteroaryl group according to the present invention is a heteroaryl group comprising at least one heteroaromatic six-membered ring with at least one nitrogen atom. Further aromatic or heteroaromatic five-membered or six-membered rings may be fused to this six-membered ring. Examples of electron-deficient heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, or quinoxaline.

[0032] An aromatic ring system according to this invention contains 6 to 60 carbon atoms in the ring system, preferably 6 to 40 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 2 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N,O and / or S. For the purposes of this invention, an aromatic or heteroaromatic ring system is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be linked by a non-aromatic unit, such as a carbon, nitrogen, or oxygen atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc., are also to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a short alkyl group. Preferably, the aromatic ring system is selected from fluorene, 9,9'-spirobifluorene, 9,9-diaryllamine, or groups in which two or more aryl and / or heteroaryl groups are linked to one another by single bonds.

[0033] Within the scope of the present invention, the following are preferably used as the groupings of an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group, which may contain 1 to 20 carbon atoms and in which individual hydrogen atoms or CH₂ groups may also be substituted by the groups mentioned above: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl or octynyl.Unter einer Alkoxygruppe mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe mit 1 bis 40 C-Atomen werden insbesondere Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n-Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluormethylthio, Pentafluorethylthio, 2,2,2-Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio verstanden.In general, alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, wherein one or more non-adjacent CH2 groups can be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO2, preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.

[0034] An aromatic or heteroaromatic ring system with 5 to 60 or 5 to 40 aromatic ring atoms, respectively, which may be further substituted with the aforementioned substituents and which may be linked via any positions on the aromatic or heteroaromatic compound, is understood to include, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, thiophene, Benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinazolin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Gruppen,which are derived from combinations of these systems.

[0035] In the context of this description, the phrase "two or more residues can form a ring" means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0036] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following diagram:

[0037] In a preferred embodiment of the invention, Ar a< and Ar b<, whether identical or different, represent an aromatic or heteroaromatic ring system with 6 to 14 aromatic ring atoms, which may be substituted with one or more Ar or Ra< groups, preferably an aryl or heteroaryl group. In a particularly preferred embodiment of the invention, Ar a< and Ar b<, whether identical or different, represent benzene, naphthalene, phenanthrene, dibenzofuran, dibenzothiophene, or carbazole, each of which may be substituted with one or more Ar or Ra< groups. Preferably, at least one of the groups Ar a< and / or Ar b< represents benzene.

[0038] In a preferred embodiment, it may be provided that the compounds according to the invention comprise a structure of formula (III) or (IIIa), wherein the compounds according to the invention may particularly preferably be selected from the compounds of formula (III) or (IIIa), where the symbols R c< , R d< , Y 1< , Y 2< , L, X, R 1< and p have the meanings mentioned above, especially for formula (I) and the other symbols have the following meaning: X a< represents N or CR a< in each occurrence, whether the same or different, preferably CR a<, provided that no more than two of the groups X a< represent N in a cycle, where R a< has the meaning set forth above, in particular for formula (I); or two adjacent X a< together represent a group of the following formula, where the dashed bonds represent the linkage of the group within the structure; X, in each occurrence, stands for N or CR<b, preferably for CR<b, with the proviso that no more than two of the groups X<b< in a cycle stand for N, R<b< having the meaning set forth above, in particular for formula (I); or two adjacent X<b< together stand for a group of the following formula, where the dashed lines represent the linkage of the group within the structure.

[0039] Furthermore, R<d> in formula (III) and in formula (IIIa) at the non-cyclic alkenyl group preferably represents H or D, and R<d> in formula (IIIa) in the five-membered ring preferably represents methyl or CN. Furthermore, X in formula (IIIa) preferably represents O or S, particularly preferably O, the explicitly drawn R<1 in formula (IIIa) preferably represents optionally deuterated methyl, and the index p in formula (IIIa) preferably represents 1.

[0040] Preferably, it can be provided that in formulas (III) (or (IIIa) there are no more than three, preferably no more than two, groups X< a< and X< b< representing N. Particularly preferably, all groups X< a< and X< b< represent CR< a< and CR< b< respectively, or the condensed benzo groups described above.

[0041] In a particularly preferred embodiment, it can be provided that the compounds according to the invention comprise a structure of formula (IV) or (IVa) to (IVf), wherein the compounds according to the invention can particularly preferably be selected from the compounds of formula (IV) or (IVa) to (IVf). where the compounds may also be partially or completely deuterated, Z stands for a group of formula (Z-1) or (Z-2), the symbols R a< , R b< , R c< , R d< , Y 1< , Y 2< and L have the meanings mentioned above, especially for formula (I), and the other symbols have the following meaning: mist 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1; nist 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1.

[0042] The following embodiments are therefore suitable: formula Group Z (IV) (Z-1) (IV) (Z-2) (IVa) (Z-1) (IVa) (Z-2) (IVb) (Z-1) (IVb) (Z-2) (IVc) (Z-1) (IVc) (Z-2) (IVd) (Z-1) (IVd) (Z-2) (IVe) (Z-1) (IVe) (Z-2) (IVf) (Z-1) (IVf) (Z-2)

[0043] Preferably, the groups of Z are selected from the groups of formulas (Z-1), (Z-2') and (Z-2") and in particular from the groups of formulas (Z-1) and (Z-2a) to (Z-2d).

[0044] If Z represents a group of formula (Z-2), then the following embodiments are preferred: formula Group Z (IV) (Z-2') (IV) (Z-2") (IVa) (Z-2') (IVa) (Z-2") (IVb) (Z-2') (IVb) (Z-2") (IVc) (Z-2') (IVc) (Z-2") (IVd) (Z-2') (IVd) (Z-2") (IVe) (Z-2') (IVe) (Z-2") (IVf) (Z-2') (IVf) (Z-2")

[0045] Furthermore, it is preferably provided, inter alia, in formulas (I), (II), (IIa), (III), (IIIa), (IV) and (IVa) to (IVf) that the group L represents a bond, C(R)₂, O, S, NAr or NR, and simultaneously the group Y₂< represents C(R e< )₂ and simultaneously the group Y₁< represents O, S, Se, Te, NR, NAr, preferably S or Se. In a particularly preferred embodiment of the invention, L represents a bond or C(R)₂, in particular a bond, and Y₂< represents C(R e< )₂ and Y₁< represents S or Se. In the compounds of formulas (IVa) to (IVf), the group Y₂< preferably represents C(R e< )₂ and the group Y₁< represents O, S, Se, Te, NR, NAr, preferably S or Se.

[0046] Furthermore, preferably, inter alia in formulas (I), (II), (IIa), (III), (IIIa) and / or (IV) or (IVa) to (IVf), the group Y 2< can be provided for NR e< , BR e< , C(R e< ) 2 , Ge(R e< ) 2 , Si(R e< ) 2 , -CR e< =CR e< -, C=NR e< , preferably for C(R e< ) 2 and the residue R e< of the group Y 2< can be a straight-chain alkyl group with 1 to 10 C atoms or for a branched or cyclic alkyl group with 3 to 12 C atoms, wherein the alkyl group can be partially or completely deuterated and substituted with one or more residues R 1<, or for an aryl or heteroaryl group with 5 to 12 aromatic ring atoms, preferably a phenyl group, which may be partially or completely deuterated and may be substituted by one or more R 1< residues, wherein the two R e< residues of the group Y 2< together can form a ring with 5 to 10 ring atoms, which may be substituted by one or more R 1< residues.In a particularly preferred embodiment, the group Y 2< represents C(R e< ) 2, and the two R e< residues of the group Y 2< together form a ring with 5 to 10 ring atoms, which may be substituted by one or more R 1< residues. This preferably results in a spiro system, wherein the ring formed by the two R e< residues preferably represents a 5-membered, a 6-membered, a 7-membered, or an 8-membered ring, which may be bridged. It is particularly preferred that the ring formed by the two R e< residues is a monocyclic cyclopentyl, cyclohexyl, or cycloheptyl ring, preferably a monocyclic cyclopentyl or cyclohexyl ring, or represents a tricyclic adamantyl ring.If Y 2< represents C(R e< ) 2, R e< preferably represents F, methyl, ethyl, neo-pentyl, or phenyl, wherein these groups may also be partially or completely deuterated, and wherein the two groups R e< may also form a ring with each other, or the two groups R e< together with the carbon atom to which they bond form a cyclopentyl, cyclohexyl, or adamantanyl group, which may also be partially or completely deuterated. R e< particularly preferably represents methyl, which may also be partially or completely deuterated.

[0047] Furthermore, the residue R<c> can be configured to represent H, D, a straight-chain alkyl group with 1 to 10 carbon atoms, a branched or cyclic alkyl group with 3 to 12 carbon atoms, wherein the alkyl group can be substituted by one or more residues R<1, or an aryl or heteroaryl group with 5 to 12 aromatic ring atoms, preferably a phenyl group, which can be substituted by one or more residues R<1, wherein the residue R<c and R<d together can form a ring with 5 to 10 ring atoms, which can be substituted by one or more residues R<1. In a particularly preferred embodiment of the invention, the residue R<c> represents H, D, methyl, or phenyl, most preferably H or D.

[0048] Furthermore, the residue R<d> can be configured to represent H, D, a straight-chain alkyl group with 1 to 10 carbon atoms, a branched or cyclic alkyl group with 3 to 12 carbon atoms, wherein the alkyl group can be substituted by one or more residues R<1, or an aryl or heteroaryl group with 5 to 12 aromatic ring atoms, preferably a phenyl group, which can be substituted by one or more residues R<1, wherein the residue R<d> can form a ring with 5 to 10 ring atoms together with the residue R<c, which can be substituted by one or more residues R<1. In a particularly preferred embodiment of the invention, the residue R<d> represents H or D.

[0049] Furthermore, it can be stipulated that the residues R< c< and R< d< are the same. It can also be stipulated that the residues R< c< and R< d< are different.

[0050] In a particularly preferred embodiment, R<c>< and R<d>< may be identical and each represent H or D, respectively. In a further particularly preferred embodiment, R<c>< and R<d>< may together form a ring with 5 to 10 ring atoms. Furthermore, R<c>< may represent H or D, and R<d>< may represent a straight-chain alkyl group with 1 to 10 carbon atoms, a branched or cyclic alkyl group with 3 to 12 carbon atoms (where the alkyl group may be substituted by one or more R1<), or an aryl or heteroaryl group with 5 to 12 aromatic ring atoms, preferably a phenyl group, which may be substituted by one or more R1<.

[0051] In a preferred embodiment, the compounds according to the invention can comprise a structure of formulas (V-1) to (V-80), particularly preferably the compounds according to the invention can be selected from the compounds of formulas (V-1) to (V-80), where the symbols R a< , R b< , R c< , R d< , R e< , Y 2< and L have the meanings mentioned above, especially for formula (I), Z stands for a group of formula (Z-1) or (Z-2) and the other symbols have the following meaning: Gist, in each occurrence the same or different O, S, Se, Te, NAr', NR 1< , BR 1< , C(R 1< ) 2 , Ge(R 1< ) 2 , Si(R 1< ) 2 , -C(R 1< ) 2 -(CR 1< ) 2 -, -CR 1< =CR 1< -, C=NR 1< , S=O, SO 2 or an ortho-linked arylene or heteroarylene group with 5 to 14 aromatic ring atoms, which may be substituted by one or more R 1< residues, wherein the R 1< residue has the meaning previously mentioned, in particular for formula (I), preferably C(R 1< ) 2 , -C(R 1< ) 2 -(CR 1< ) 2 -, -CR 1< =CR 1< -, O, S;Y 3< is, in each occurrence, the same or different, a bond, O, S, Se, Te, NAr', NR 1< , BR 1< , C(R 1< ) 2 , Ge(R 1< ) 2 , Si(R 1< ) 2 , -CR 1< =CR 1< -, C=NR 1< , S=O, SO 2 or an ortho-linked arylene or heteroarylene group with 5 to 14 aromatic ring atoms, which may be substituted by one or more R 1< residues, wherein the R 1< residue has the meaning previously mentioned, in particular for formula (I), preferably a bond, C(R 1< ) 2 , O, S, NAr; tist 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; sist 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; mist 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1; nist 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1. ;

[0052] Other preferred embodiments are the structures of formulas (V-17) to (V-80), which contain S instead of Se.

[0053] The following embodiments are therefore suitable for formulas (V-1) to (V-8a): formula Group Z (V-1) (Z-1) (V-1) (Z-2) (V-1a) (Z-1) (V-1a) (Z-2) (V-2) (Z-1) (V-2) (Z-2) (V-2a) (Z-1) (V-2a) (Z-2) (V-3) (Z-1) (V-3) (Z-2) (V-3a) (Z-1) (V-3a) (Z-2) (V-4) (Z-1) (V-4) (Z-2) (V-4a) (Z-1) (V-4a) (Z-2) (V-5) (Z-1) (V-5) (Z-2) (V-5a) (Z-1) (V-5a) (Z-2) (V-6) (Z-1) (V-6) (Z-2) (V-6a) (Z-1) (V-6a) (Z-2) (V-7) (Z-1) (V-7) (Z-2) (V-7a) (Z-1) (V-7a) (Z-2) (V-8) (Z-1) (V-8) (Z-2) (V-8a) (Z-1) (V-8a) (Z-2)

[0054] Preferably, the groups of Z are selected from the groups of formulas (Z-1), (Z-2') and (Z-2") and in particular from the groups of formulas (Z-1) and (Z-2a) to (Z-2d).

[0055] Structures or compounds of formulas (V-1), (V-1a), (V-2), (V-2a), (V-3), (V-3a), (V-5), (V-5a), (V-6), (V-6a), (V-7), (V-7a), (V-17), (V-18), (V-21), (V-22), (V-33), (V-34), (V-37), (V-38), (V-41), (V-42), (V-45), (V-46), (V-61) and / or (V-62) are preferred, structures or compounds of formulas (V-2), (V-2a), (V-6), (V-6a), (V-18), (V-22), (V-34), (V-38), (V-42), (V-46) and / or (V-62) are particularly preferred, and structures or compounds the formulas (V-6), (V-6a), (V-22), (V-38), (V-46) and / or (V-62) are particularly preferred.

[0056] The preferences previously set out for the remainder R e< of the group Y 2< with regard to formulas (I), (II), (IIa), (III), (IIIa), (IV) and / or (IVa) to (IVf) also apply to formulas (V-1) to (V-80) accordingly.

[0057] Furthermore, for formulas (IV), (IVa) to (IVf) and / or formulas (V-1) to (V-80), it may be provided that the sum of the indices m and n is at most 10, preferably at most 8, particularly preferably at most 6 and especially preferably at most 4 and most preferably at most 2.

[0058] In a preferred embodiment of the present invention, it can be provided that at least two residues R, Ra< , Rb< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< bind, wherein the two residues R, Ra< , Rb< form at least one structure of formulas (RA-1) to (RA-12). where R 1< has the meaning explained above, the dashed bonds represent the bonding points to the atoms of the groups to which the two residues R, R a< , R b< bind, and the other symbols have the following meaning: Y 4< is the same or different for each occurrence C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), NR 1< , NAr', O or S, preferably C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), O or S;R< f< is the same or different H, D, F, in each occurrence, a straight-chain alkyl, alkoxy, or thioalkoxy group with 1 to 40 C atoms, or an alkenyl or alkynyl group with 2 to 40 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group with 3 to 20 C atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl group may each be substituted with one or more R< 2< substituents, wherein one or more non-adjacent CH2 groups are replaced by R< 2< C=CR2, C≡C, Si(R2)2, C=O, C=S, C=Se, C=NR2, C(=O)O, C(=O)NR2, NR2, P(=O)(R 1< ), O, S, SO or SO 2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< residues, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< residues;Two residues R<f< can also form a ring system with each other, or one residue R<f< can form a ring system with a residue R<1< or with a further group, wherein the residue R<2<< has the meaning previously mentioned, particularly for formula (I); sist 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; tist 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; vist 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2.

[0059] Structures of formulas RA-1, RA-3, RA-4 and RA-5 are preferred, and structures of formulas RA-4 and RA-5 are particularly preferred.

[0060] In a preferred embodiment of the present invention, it can be provided that at least two residues R, Ra< , Rb< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< bind, wherein the two residues R, Ra< , Rb< form structures of formulas (RA-1a) to (RA-4f). wherein the dashed bonds represent the attachment points to the atoms of the groups to which the two substituents R, R a< , R b< bond, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the symbols R 1< , R 2< , R f< and the indices s, and t have the meaning set forth above, in particular for formula (I) and / or formulas (RA-1) to (RA-12).

[0061] Structures of formulas RA-4f are preferred.

[0062] Furthermore, it can be provided that the at least two residues R, R a< , R b< form the structures of formulas (RA-1) to (RA-12) and form a condensed ring, represent residues R, R a< , R b< from adjacent groups X a< , X b< or represent residues R, R a< , R b< which each bond to adjacent C atoms, wherein these C atoms are preferably connected via a bond.

[0063] In a further preferred embodiment, it can be provided that at least two residues R, Ra< , Rb< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< bind, wherein the two residues R, Ra< , Rb< form the structures of formula (RB), wherein R 1< has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points to the atoms of the groups to which the two substituents R, R a< , R b< bond, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 5< is C(R 1< ) 2 , NR 1< , NAr', BR 1< , BAr', O or S, preferably C(R 1< ) 2 , NAr' or O, particularly preferably C(R 1< ) 2 or O, wherein Ar' has the meaning given above, in particular for formula (I).

[0064] It can be provided that the at least two residues R, R a< , R b< , which form the structures of formula (RB) and form a condensed ring, represent residues R, R a< , R b< from neighboring groups X a< , X b< , or represent residues R, R a< , R b< which each bind to neighboring C atoms, wherein these C atoms are preferably connected to each other via a bond.

[0065] In particular, it may be provided that in preferred structures or connections the sum of the indices r, s, t, v, m and n is preferably 0, 1, 2 or 3, and particularly preferably 1 or 2.

[0066] Particularly preferably, the compounds comprise at least one structure of the structure of formulas (VI-1) to (VI-5), particularly preferably the compounds are selected from compounds of formulas (VI-1) to (VI-5), wherein the compounds have at least one condensed ring, where the symbols R a< , R b< , R c< , R d< , Y 1< , Y 2< and L have the meanings mentioned above, especially for formula (I), the symbol o stands for the condensation points of the at least one condensed ring and the further indices have the following meaning: mist 0, 1, 2, 3 or 4, preferably 0, 1 or 2; nist 0, 1, 2 or 3, preferably 0, 1 or 2; jist 0, 1 or 2, preferably 0 or 1; kist 0 or 1.

[0067] Similarly suitable are the structures of formulas (VI-1) to (VI-5), which contain a group of formula (Z-2) instead of the group of formula (Z-1) as group Z.

[0068] Furthermore, it can be provided that the condensed ring is formed by at least two residues R a< , R b< and the further groups to which the two residues R a< , R b< bind, wherein the at least two residues R a< , R b< form structures of formulas (RA-1) to (RA-12) and / or formula (RB), preferably structures of formulas (RA-1) to (RA-12).

[0069] Furthermore, in particular in formulas (VI-1) to (VI-5) it may be provided that the sum of the indices k, j, n and m is 0, 1, 2 or 3, preferably 0, 1 or 2.

[0070] Preferably, the compounds may have at least two condensed rings, wherein at least one condensed ring is formed by structures of formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and another ring is formed by structures of formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB).

[0071] Furthermore, it may be provided that the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, and R1< according to the formulas above do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system to which the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, and R1< bind. This includes the formation of a condensed aromatic or heteroaromatic ring system with possible substituents R1< and R2<, which may be bonded to the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, and R1<.

[0072] When two substituents, which may be selected from R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, R1< and / or R2<, form a ring system, this system can be monocyclic or polycyclic, aliphatic, heteroaliphatic, aromatic, or heteroaromatic. The substituents forming the ring system can be adjacent, i.e., bonded to the same carbon atom or to carbon atoms directly bonded to one another, or they can be further apart. Furthermore, the ring systems containing the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, R1< and / or R2< can also be linked by a bond, thus resulting in ring closure. In this case, each of the corresponding bonding sites is preferably provided with a substituent R, R a< , R b< , R c< , R d< , R e< , R f< , R 1< and / or R 2<.

[0073] According to a preferred embodiment, a compound according to the invention can be represented by at least one of the structures according to formulas (I), (II), (IIa), (III), (IIIa), (IV), (IVa) to (IVf) and / or (V-1) to (V-80). Preferably, compounds according to the invention, preferably comprising structures or represented by structures according to formulas (I), (II), (IIa), (III), (IIIa), (IV), (IVa) to (IVf) and / or (V-1) to (V-80), have a molecular weight of less than or equal to 5000 g / mol, more preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol, and most preferably less than or equal to 1200 g / mol.

[0074] Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1200 g / mol.

[0075] Preferred aromatic or heteroaromatic ring systems Ar, R, Ra<, Rb<, Rc<, Rd<, Re<, Rf< and / or Ar' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3-, 4- or 9-position, dibenzofuran, which may be linked via the 1-, 2-, which may be linked at the 3rd or 4th position, dibenzothiophene, which may be linked at the 1st, 2nd, 3rd or 4th position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene,which can each be substituted with one or more residues R, R 1< or R 2< respectively.

[0076] Preferably, at least one residue R, R a< , R b< , R c< , R d< , R e< may be selected, either the same or different at each occurrence, from the group consisting of H, D, a straight-chain alkyl group with 1 to 4 carbon atoms, a branched or cyclic alkyl group with 3 to 10 carbon atoms, or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-78. Preferably, the residues R, R a< , R b< , R c< , R d< , R e< either form a fused ring, preferably according to the structures of formulas (RA-1) to (RA-12) or (RB), or the residue R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, methyl, or an aromatic or heteroaromatic ring system. selected from the groups of the following formulas Ar-1 to Ar-78,and / or the group Ar' is selected the same or different at each occurrence from the groups of the following formulas Ar-1 to Ar-78, , where R 1< has the meanings mentioned above, the dashed line represents the connection point to the corresponding group and the following also applies: Ar 1< is, in each occurrence, either the same or different, a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each of which may be substituted with one or more R 1< residues; A is, in each occurrence, either the same or different, C(R 1< ) 2 , NR 1< , O or S; p is 0 or 1, where p = 0 means that the group Ar 1< is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding residue; q is 0 or 1, where q = 0 means that no group A is bonded at this position and instead, residues R 1< are bonded to the corresponding carbon atoms.

[0077] The structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-44), (Ar-45), (Ar-46), (Ar-69), (Ar-70), (Ar-75) are preferred, and structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.

[0078] If the above-mentioned groups have multiple groups A, then all combinations from the definition of A are possible. Preferred embodiments are those in which one group A stands for NR 1< and the other group A for C(R 1< ) 2, or in which both groups A stand for NR 1<, or in which both groups A stand for O.

[0079] When A stands for NR 1<, the substituent R 1< bonded to the nitrogen atom preferably represents an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be substituted by one or more R 2< groups. In a particularly preferred embodiment, this substituent R 1< represents, in each instance, an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 18 aromatic ring atoms, which has no fused aryl groups and no fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which may also be substituted by one or more R 2< groups.Phenyl, biphenyl, terphenyl, and quaterphenyl with linkage patterns as listed above for Ar-1 to Ar-11 are preferred, wherein these structures may be substituted by one or more R2< groups instead of R1<, but are preferably unsubstituted. Triazine, pyrimidine, and quinazoline as listed above for Ar-47 to Ar-50, Ar-57, and Ar-58 are also preferred, wherein these structures may be substituted by one or more R2< groups instead of R1<.

[0080] Preferred substituents R, R a< , R b< , R c< , R d< , R e< and R f< are described below.

[0081] In a preferred embodiment of the invention, R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, F, CN, Si(R 1< ) 3 , B(OR 1< ) 2 , a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R 1< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R 1< groups.

[0082] In a further particularly preferred embodiment of the invention, substituent R, R a< , R b< , R c< , R d< , R e< is selected, whether the same or different at each occurrence, from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R 1< groups, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, preferably with 6 to 24 aromatic ring atoms, particularly preferably with 6 to 18 aromatic ring atoms, and most preferably with 6 to 13 aromatic ring atoms, which may each be substituted by one or more R 1< groups.

[0083] Furthermore, it can be provided that at least one substituent R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, preferably with 6 to 24 aromatic ring atoms, particularly preferably with 6 to 18 aromatic ring atoms, most preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more R 1< groups, or a group N(Ar') 2 . Preferred embodiments of the aromatic or heteroaromatic ring system are the structures (Ar-1) to (Ar-78) shown above.

[0084] In a further preferred embodiment of the invention, the substituents R, R a< , R b< , R c< , R d< , Re< either form a ring according to the structures of formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB) or the substituent R, R a< , R b< , R c< , R d< , Re< is the same or different at each occurrence selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more R 1< substituents, or a group N(Ar') 2 . Particularly preferred is substituent R, R a< , R b< the same or different in each occurrence selected from the group consisting of H, D or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more substituents R 1<.

[0085] Preferably, at least one substituent R, R a< , R b< , R c< , R d< , R e< is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or triphenylene, each of which may be substituted with one or more R 1< groups. Here, the term substituent specifically means that R, R a< , R b< , R c< , R d< , R e< are not equal to H. Furthermore, the substituents R, R a< , R b< , R c< , R d< , R e< can be the same or different if two or more substituents are present that are selected from the aforementioned aromatic or heteroaromatic group.

[0086] In a further embodiment, at least one substituent R, R a< , R b< , R c< , R d< , R e< is selected from o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenylpyrimidin-2-yl, 4,6-diphenyltriazin-2-yl, naphthalene, phenanthrene, chrysene, spirobifluorene, triphenylene, anthracene, benzanthracene, fluorene and / or pyrene, each of which may be substituted with one or more R 1< groups. Spirobifluorene, o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenylpyrimidin-2-yl, and 4,6-diphenyltriazin-2-yl groups are preferred. The substituents R, R a< , R b< , R c< , R d< , R e< can be the same or different if two or more substituents are selected from the aforementioned aromatic group.

[0087] In a preferred embodiment of the invention, R< f< is selected, whether the same or different, from the group consisting of a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R< 1< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R< 2< groups.

[0088] In a further preferred embodiment of the invention, R f< is selected, whether the same or different, from the group consisting of H, D, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more R 2< groups.

[0089] In a preferred embodiment of the invention, R f< is selected, in each occurrence, as the same or different from the group consisting of a straight-chain alkyl group with 1 to 6 C atoms or a cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may be substituted with one or more R 2< residues, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which may each be substituted by one or more R 2< residues; two R f< residues may also form a ring system together.Particularly preferred is R f< selected, in each occurrence, as the same or different from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 C atoms or a branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, in particular with 6 aromatic ring atoms, which may be substituted by one or more, preferably non-aromatic, R 2< groups, but is preferably unsubstituted; two R f< groups may form a ring system together. Particularly preferred is R f< selected from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 C atoms, or a branched alkyl group with 3 to 6 C atoms, whether the same or different in each occurrence.R f< is particularly preferably a methyl group or a phenyl group, wherein two phenyl groups can form a ring system together, with a methyl group being preferred over a phenyl group.

[0090] Preferred aromatic or heteroaromatic ring systems, for which substituents R, R a< , R b< , R c< , R d< , R e< , R f< or Ar or Ar' respectively stand, are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, which can be linked at the 2nd, 3rd or 4th position, dibenzothiophene, which can be linked at the 1st, 2nd, 3rd or 4th position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline,Quinoxaline, phenanthrene, or triphenylene, each of which may be substituted with one or more R, R1<, or R2< substituents, respectively. The structures Ar-1 to Ar-78 listed above are particularly preferred, with structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) being preferred and structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) being particularly preferred. It should be noted that structures Ar-1 to Ar-78 are represented with a substituent R1<. In the case of the ring systems Ar, these substituents R 1< are to be replaced by R and in the case R f<, these substituents R 1< are to be replaced by R 2<.

[0091] Further suitable groups R, R a< , R b< , R c< , R d< are groups of the formula -Ar 4< -N(Ar 2< )(Ar 3< ), where Ar 2< , Ar 3< and Ar 4< represent, whether identical or different, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may be substituted with one or more R 1< groups. The total number of aromatic ring atoms of Ar 2< , Ar 3< and Ar 4< is at most 60 and preferably at most 40.

[0092] Ar4< and Ar2< can be linked to each other and / or Ar2< and Ar3< can also be linked to each other by a group selected from C(R1<)2, NR1<, O, or S. Preferably, the linkage of Ar4< and Ar2< to each other or of Ar2< and Ar3< to each other is ortho to the position of the linkage with the nitrogen atom. In a further embodiment of the invention, none of the groups Ar2<, Ar3<, or Ar4< are linked to each other.

[0093] Preferably, Ar 4< is an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, each of which may be substituted with one or more R 1< groups. Particularly preferably, Ar 4< is selected from the group consisting of ortho-, meta-, or para-phenylenes or ortho-, meta-, or para-biphenyls, each of which may be substituted by one or more R 1< groups, but preferably are unsubstituted. Most preferably, Ar 4< is an unsubstituted phenylene group.

[0094] Preferably, Ar 2< and Ar 3< are the same or different at each occurrence an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which may be substituted with one or more R 1< residues. Particularly preferred groups Ar 2< and Ar 3< are selected, either identically or differently at each occurrence, from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-, 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-dibenzothiophene, indenocarbazole, indolocarbazole, 2-, 3- or 4-pyridine, 2-, 4- or 5-pyrimidine, pyrazine, Pyridazine, triazine, phenanthrene or triphenylene, each of which may be substituted with one or more R 1< residues.Particularly preferred are Ar 2< and Ar 3<, whether identical or different in each occurrence, selected from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, in particular 1-, 2-, 3- or 4-fluorene, or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobibfluorene.

[0095] In a further preferred embodiment of the invention, R 1< is selected, whether the same or different at each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which may be substituted by one or more R 2< groups.In a particularly preferred embodiment of the invention, R 1< is selected, whether the same or different, from the group consisting of H, a straight-chain alkyl group with 1 to 6 C atoms, in particular with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, which may be substituted by one or more R 2< groups, but is preferably unsubstituted.

[0096] In a further preferred embodiment of the invention, R 2< is the same or different at each occurrence H, D, an alkyl group with 1 to 4 C atoms or an aryl group with 6 to 10 C atoms, which may be substituted with an alkyl group with 1 to 4 C atoms, but preferably is unsubstituted.

[0097] In compounds according to the invention, which are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds processed from solution, compounds substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms, or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.

[0098] Furthermore, it may be provided that the compound comprises exactly two or exactly three structures according to formula (I), (II), (IIa), (III), (IIIa), (IV), (IVa) to (IVf), (V-1) to (V-80) and / or (VI-1) to (VI-5).

[0099] In a preferred embodiment, the compounds are selected from compounds according to formula (D-1), wherein the group L' represents a compound group, preferably a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more R1< groups, and the other symbols used have the meanings given above, in particular for formula (I). L1< may bind to Ara<, Arb<, L, Y1< or Y2< or may bind to the position of Rc<, in which case Rc< is not present.

[0100] In a further preferred embodiment of the invention, L 1< represents a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms or a heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more substituents R 1<, but preferably is unsubstituted, wherein R 1< can have the meaning mentioned above, particularly for formula (I). Particularly preferably, L 1< represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more substituents R 1<, but preferably is unsubstituted, wherein R 1< can have the meaning mentioned above, particularly for formula (I).

[0101] Furthermore preferably, the symbol L' shown, among other things, in formula (D1) represents, in the same or different ways, a bond or an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e. via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0102] Furthermore, it may be provided that the group L 1< shown in formula (D1) comprises an aromatic ring system with at most two fused aromatic and / or heteroaromatic 6-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures.

[0103] Structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.

[0104] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, fluorenylene, spirobifluorenylene, dibenzofuranyles, dibenzothienylene and carbazolylene, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0105] The preferred embodiments mentioned above can be combined arbitrarily within the limitations defined in claim 1. In In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0106] Examples of preferred connections according to the embodiments listed above are the connections listed in the following table: 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 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 - 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282

[0107] Preferred embodiments of the compounds according to the invention are described in more detail in the examples, wherein these compounds can be used alone or in combination with others for all uses according to the invention.

[0108] Provided that the conditions specified in claim 1 are met, the preferred embodiments mentioned above can be combined with one another as desired. In a particularly preferred embodiment of the invention, the preferred embodiments mentioned above apply simultaneously.

[0109] The compounds according to the invention can in principle be produced by various methods. However, the methods described below have proven to be particularly suitable.

[0110] Therefore, a further object of the present invention is a method for producing the compounds according to the invention, in which a basic framework with an aromatic amino group is synthesized and at least one heterocyclic residue is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0111] Suitable compounds comprising a basic framework with an aromatic amino group can often be obtained commercially, with the starting compounds presented in the examples being obtainable by known methods, which are therefore referenced here.

[0112] These connections can be implemented with other connections through known coupling reactions, the necessary conditions for which are known to the person skilled in the art, and detailed information in the examples assists the person skilled in the art in carrying out these conversions.

[0113] Particularly suitable and preferred coupling reactions, all leading to CC and / or CN couplings, are those according to BUCHWALD, SUZUKI, ULLMANN, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, and HIYAMA. These reactions are widely known, and the examples provided offer further guidance to those skilled in the art.

[0114] The synthesis of the compounds according to the invention can be carried out, among other things, according to the following scheme 1.

[0115] In a first step, a compound with an aromatic amino group (1) can be reacted with a heterocycle (2). Preferred heterocycles are, for example, pyrrole, furan, thiophene, selenophene, or tellurophene derivatives. The resulting compound (3) can be reacted with a carbonyl compound (4) in a hydroxyalkylation reaction to give a nitrogen-containing hydroxy compound (5), which is represented as step 2 in the present scheme. In step 3, this hydroxy compound (5) is cyclized and subsequently derivatized to a carbonyl compound (8) by formylation or acylation. In step 5, the carbonyl compound (8) can be reacted with malononitrile (9) in a Knoevenagel condensation to give a compound (10) according to the invention.

[0116] The Knoevenagel condensation is described, among other places, in S. Haig et al., Chem. Mat., 2011, 23(20), 4435. Scheme 1: Step 1: Ullmann coupling

[0117] Step 2: Hydroxyalkylation

[0118] Step 3: Cyclization

[0119] Step 4: Formylation or acylation

[0120] Step 5: Knoevenagel condensation

[0121]

[0122] The synthesis of the compounds according to the invention can further be carried out according to the following scheme 2, by which in particular compounds with further groups Y 2< can be obtained, such as O, S, Se, Te, NAr, NR e< , BAr, BR e< , Ge(R e< ) 2 , Si(R e< ) 2 , -CR e< =CR e< -, C=NR e< , S=O, SO 2 .

[0123] In a first step, a compound with an aromatic amino group (11) can be reacted with a heterocycle (12) by double Ullmann coupling. Preferred heterocycles are, for example, pyrrole, furan, thiophene, selenophene, or tellurophene derivatives. The resulting compound (13) can be derivatized to a carbonyl compound (15) by formylation or acylation. In step 3, the carbonyl compound (15) can be reacted with malononitrile (16) in a Knoevenagel condensation to give a compound (17) according to the invention.

[0124] Preferably, secondary amines known from the literature can be used as the aromatic amino group (11) and 1,2-bis-halogenated 5-ring heterocycles as the heterocycles (12). Scheme 2: Step 1: Ullmann coupling

[0125] Y 2< : NHR, OH, SH, SeH Step 2: Formylation or acylation

[0126] Step 3: Knoevenagel condensation

[0127]

[0128] Variations of the previously presented scheme for the preparation of compounds / structures, in which the group Y 2< stands for, for example, Te, BR e< , Ge(R e< ) 2 , Si(R e< ) 2 , -CR e< =CR e< -, C=NR e< , S=O, SO 2, are known to the person skilled in the art.

[0129] Furthermore, the synthesis of the compounds according to the invention can be carried out according to the following scheme 3, by which compounds with further groups Y 2< can in particular be obtained, such as a bond.

[0130] Starting from (18) and (19), the intermediates (20) can be obtained according to D. Bader et al., J. Org. Chem., 2020, 85(5), 3865. The intermediates (20) can then be reacted to give the corresponding compounds (22) according to the invention by means of steps 2 and 3. Scheme 3: Step 1: Ullmann coupling

[0131] Y 2< : NHR, OH, SH, SeH Analogous to step 2: Formylation or acylation

[0132] Analogous to step 3: Knoevenagel condensation

[0133]

[0134] To introduce the groups of formula (Z-2) with p = 1, the Knoevenagel condensation can be carried out instead of maleonitrile (H 2 C(CN) 2 ) with 2-(4,5,5-trimethyl-2(5H)-furanylidene)-propanedinitrile or 2-(4,5,5-trimethyl-2(5H)-thiophenylidene)-propanedinitrile and their derivatives.

[0135] The meaning of the symbols used in Schemes 1, 2, and 3 essentially corresponds to that defined for formula (I) and preferred embodiments of these structures, respectively, although for the sake of clarity, numbering and a complete representation of all symbols have been omitted. Furthermore, for the sake of clarity, the use of symbols to represent possible nitrogen atoms in the heteroaromatic rings, as represented in particular by the symbols X< a< and X< b< in formula (III), has often been omitted.These details are therefore to be understood as examples, whereby the person skilled in the art is able to transfer the syntheses set out before and below, in particular in the examples, to compounds in which one or more of the symbols X a< and X b< stand for nitrogen or which contain other aromatic groups, such as naphthalene or phenanthrene, instead of the benzene groups in the basic structure.

[0136] The principles of the manufacturing processes described above are known from the literature for similar compounds and can be easily adapted by a person skilled in the art to produce the compounds according to the invention. Further information can be found in the examples.

[0137] By these methods, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1< H-NMR and / or HPLC).

[0138] The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably proceeds via the halogen functionality or the boronic acid functionality, or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as crosslinked or uncrosslinked layers.

[0139] A further aspect of the invention is therefore oligomers, polymers, or dendrimers containing one or more of the structures of formula (I) and preferred embodiments of this formula listed above, or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of formula (I) and preferred embodiments of this formula are present with the polymer, oligomer, or dendrimer. Depending on the linkage of the structures of formula (I) and preferred embodiments of this formula or of the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers, or dendrimers can be conjugated, partially conjugated, or non-conjugated. The oligomers or polymers can be linear, branched, or dendritic.The same preferences apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers as described above.

[0140] To produce the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with further monomers. Copolymers are preferred, wherein the units according to formula (I) or the preferred embodiments described above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, and particularly preferably 20 to 80 mol%. Suitable and preferred comonomers forming the polymer backbone are selected from fluorenes (e.g., according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g., according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g., according to WO 92 / 18552), carbazoles (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g., according to EP 1028136), dihydrophenanthrenes (e.g., according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g., according to WO 2004 / 041901 or WO 2004 / 113412). Ketones (e.g. according to WO 2005 / 040302), phenanthrenes (e.g.(according to WO 2005 / 104264 or WO 2007 / 017066) or several of these units. The polymers, oligomers and dendrimers may contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.

[0141] Of particular interest are compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to the invention are particularly preferred, comprising structures according to formula (I) or the preferred embodiments described above and below, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, most preferably at least 125 °C and most preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08).

[0142] For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin. Dodecyl benzene, ethyl benzoate, indane, NMP, p-cymene, phenetol,1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacic acid ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0143] A further object of the present invention is therefore a formulation or composition comprising at least one compound according to the invention and at least one further compound. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as the formulation. The further compound may also be at least one further organic or inorganic compound that is also used in the electronic device, for example, a comaterial, wherein these compounds differ from the compounds according to the invention. Suitable comaterials are listed later in connection with the organic electronic device. The further compound may also be a polymer.

[0144] Another object of the present invention is therefore a composition comprising a compound according to the invention and at least one further organically functional material. Functional materials are generally the organic or inorganic materials which are introduced between the anode and the cathode. Preferably, the organically functional material is selected from the group consisting of photosensitizers, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, and hole blocking materials, preferably photosensitizers, electron transport materials, electron injection materials, and hole blocking materials.

[0145] Another object of the present invention is the use of a compound according to the invention in an electronic device, preferably an organic photoelectric device, in particular in an organic optical detector, preferably as a photosensitizer, especially preferably as a green, red, infrared or blue photosensitizer, and particularly preferably as a green photosensitizer.

[0146] A further object of the present invention is an electronic device comprising at least one compound according to the invention. An electronic device within the meaning of the present invention is a device comprising at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0147] The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), small molecule-based organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), "organic plasmon emitting devices" (DM Koller et al.)., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic optical detectors, organic photoreceptors, organic electrical sensors, organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic optical detectors.

[0148] The organic optical detector contains a cathode, an anode, and at least one light-absorbing layer. In addition to these layers, it may contain further layers, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge-generation layers. Interlayers, such as those with exciton blocking properties, may also be placed between two light-absorbing layers. It should be noted, however, that not every one of these layers is necessarily present. The organic optical detector may contain a single light-absorbing layer, or it may contain multiple light-absorbing layers.

[0149] The compound according to the invention can be used in different layers, depending on the precise structure. A preferred organic optical detector is one containing a compound according to formula (I) or the preferred embodiments described above in a light-absorbing layer as a photosensitizer, preferably an infrared, red, green, or blue photosensitizer, particularly preferably a green photosensitizer, wherein the color indicates the color of the light absorbed by the photosensitizer.

[0150] When the compound according to the invention is used as a photosensitizer in a light-absorbing layer, a suitable co-material, which is known as such, is preferably used. The co-material is used either as a mixture with the photosensitizer or in a layer adjacent to the layer containing the photosensitizer.

[0151] Suitable co-materials, which can be used in combination, i.e. as a mixture with the compounds according to the invention or in a layer adjacent to the layer containing the compounds according to the invention, are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, etc. B. CBP (N,N-Bis-carbazolylbiphenyl) or those in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar comaterials, e.g. B. according to WO 2007 / 137725, silanes, e.g. B. according to WO 2005 / 111172, azaboroles or boron esters, e.g. b.according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphol derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. according to JP 3139321 B2.

[0152] In a particularly preferred embodiment, one or more compounds according to the invention, as described in formula (I) or in the preferred embodiments, may be used in combination with electron transport materials, electron injection materials, or hole-blocking materials. Subphthalocyanines, subphthalocyanine derivatives, fullerenes, or fullerene derivatives are particularly preferred. Such compounds are known to those skilled in the art for use in organic optical detectors.

[0153] This embodiment is particularly preferred in the case that the compound according to the invention can be used as hole conductor materials, hole injection materials and / or electron blocking materials.

[0154] Preferred subphthalocyanines, subphthalocyanine derivatives, fullerenes, or fullerene derivatives are described, inter alia, in European patent application EP 3848374 A1, filed with the European Patent Office on 13 January 2021 under application number EP 21151295.9, to which this publication is incorporated by reference for disclosure purposes. These materials are set out in particular on pages 84 to 86 (see paragraphs

[322] to

[332] ).

[0155] Furthermore, a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579, can be used as a comaterial. In particular, compounds with a large band gap that do not participate, or at least not to a significant extent, in charge transport of the light-absorbing layer are suitable as comaterials in combination with the compound according to the invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or in WO 2010 / 006680.

[0156] In a further embodiment of the invention, the organic optical detector according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, i.e. the light-absorbing layer is directly adjacent to the hole injection layer or the anode, and / or the light-absorbing layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0157] In the further layers of the organic optical detector according to the invention, all materials commonly used in the prior art can be employed. Therefore, without any inventive effort, a person skilled in the art can use all materials known for organic optical detectors in combination with the compounds according to formula (I) or the preferred embodiments described above.

[0158] A further preferred organic optical detector is characterized in that one or more layers are coated using a sublimation process. The materials are deposited in vacuum sublimation systems at an initial pressure of less than 10⁻⁵ mbar, preferably less than 10⁻⁶ mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10⁻⁷ mbar.

[0159] A preferred organic optical detector is characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10⁻⁵ mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured.

[0160] A further preferred organic optical detector is characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing process, e.g., screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this purpose, which can be obtained, for example, by suitable substitution.

[0161] Formulations for applying a compound according to formula (I) or its previously described preferred embodiments are novel. A further object of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or its previously described preferred embodiments.

[0162] Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.

[0163] These methods are generally known to those skilled in the art and can be applied by them without inventive effort to organic optical detectors containing the compounds according to the invention.

[0164] Further details of preferred electronic devices, in particular organic optical detectors, and their manufacture are known from the prior art. These are described, inter alia, in European patent application EP 3848374 A1, filed with the European Patent Office on 13 January 2021 under application number EP 21151295.9, and this publication is incorporated herein by reference for disclosure purposes. In particular, reference is made to Figures 1 to 10 described in EP 3848374 A1, which are set forth, inter alia, on pages 83 to 90 of EP 3848374 A1.

[0165] The electronic devices according to the invention, in particular organic optical detectors, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic optical detectors containing compounds according to formula (I) or the preferred embodiments described above and below, especially as photosensitizers, exhibit a very long lifetime. 2. Electronic devices, in particular organic optical detectors containing compounds according to formula (I) or the preferred embodiments described above and below as photosensitizers, exhibit excellent efficiency. Here, compounds according to the invention according to formula (I) or the preferred embodiments described above and below result in a low operating voltage when used in electronic devices. 3. The compounds according to the invention according to formula (I) or the preferred embodiments described above and below exhibit very high stability, in particular thermal stability and lower deposition temperatures. 4.With compounds according to formula (I) or the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, especially organic optical detectors. This results in these devices exhibiting high photocurrent efficiency of the photosensitizer and / or excellent energy transfer. 5. Compounds according to formula (I) or the preferred embodiments described above and below exhibit excellent glass film formation. 6. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions and show excellent solubility.

[0166] These aforementioned advantages do not come at the cost of an excessively high deterioration of other electronic properties.

[0167] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[0168] All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[0169] It should further be noted that many of the features, and in particular those of the preferred embodiments, of the present invention are themselves inventive and not merely part of the embodiments of the present invention. Independent protection for these features may be sought in addition to or as an alternative to any currently claimed invention.

[0170] The teaching on technical action disclosed in the present invention can be abstracted and combined with other examples.

[0171] The invention is further explained by the following examples, without being intended to limit it. A person skilled in the art can implement the invention in its entire disclosed scope from the descriptions and, without inventive effort, create further connections according to the invention and use them in electronic devices or apply the method according to the invention. Examples:

[0172] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The information in square brackets and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have several enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. Synthone known from literature LS:

[0173] Synthesis of synthons: Example S1:

[0174]

[0175] Procedure analogous to K. Mazzio et al., Appl. Mat. & Interfaces, 2011, 3, 2, 271. A solution of 3.36 g (10 mmol) of 8,8-dimethyl-8H-seleno-[3',2':5,6]pyrido[3,2,1-jk]carbazole [2661611-42-1] and 1.59 g (10 mmol) of 4-methyl-3-cyclohexene-1-carbonyl chloride [16695-95-7] ​​in 150 ml DCM, cooled to 0 °C, is added dropwise over 10 min to a solution of 1.73 g (13 mmol) of anhydrous aluminum chloride and stirred for 1 h. The mixture is quenched by the careful addition of 50 g of ice, and the organic compounds are separated. Phase off, wash these twice with 50 ml of water each, once with 50 ml of saturated

[0176] Sodium bicarbonate (1:1) is prepared by filtering over a saline solution and drying over magnesium sulfate. The filtrate is concentrated under vacuum, the orange oil is mixed with 30 g of 85% polyphosphoric acid, the mixture is homogenized at 50 °C, and then the temperature is increased to 100 °C. After 30 minutes, the mixture is allowed to cool to 50 °C, and then 200 ml of water is added dropwise while cooling (caution: exothermic, induction period, maximum temperature 80 °C). The precipitated solid is filtered off, reconstituted in 150 ml of DCM, washed once with 50 ml of saturated sodium bicarbonate solution, twice with 50 ml of water each time, once with 50 ml of saturated saline solution, and dried over magnesium sulfate. The desiccant is filtered off, and the filtrate is concentrated under vacuum to dryness. Further purification of the crude product is carried out by chromatography (Torrent column chromatograph from A. Semrau). Yield: 1.03 g (2.3 mmol) 23%; Purity: approx. 97% n.l. < H-NMR.

[0177] The following connections can be represented analogously: Example. Educt product yield S2 B12 - Step 3 25 % 932-67-2 S3 B14 - Step 3 27 % 932-67-2 S4 25% 2661611-42-1 3350-78-5 S5 21 % 2661611-42-1 80385-46-2 S6 23 % 2661611-42-1 41199-96-6 S100 47 % 2661611-42-1 65680-40-2 Synthesis of the compounds according to the invention:

[0178] The aldehydes (8) can be prepared analogously to US 2021 / 0234103, page 70, by using the corresponding starting materials listed below: an o-bromoamine (1), a 5-ring heterocycle (2) (pyrrole, furan, thiophene, selenophene, tellurophene), a ketone (4), and subsequent formylation of the compounds (6) with a formamide (7) or acylation, see Scheme 1, steps 1 to 4. In the last step 5, the carbonyl compounds (8) are reacted with malononitrile (9) in a Knoevenagel condensation (e.g., S. Haig et al., Chem. Mat., 2011, 23(20), 4435) to give the compounds (10) according to the invention. Scheme 1: Step 1: Ullmann coupling

[0179] X: Single binding, CR 2 , NR, O, S, Se, Te Step 2: Hydroxyalkylation

[0180] Step 3: Cyclization

[0181] Step 4: Formylation or acylation

[0182] Step 5: Knoevenagel condensation

[0183] Alternative procedure for step 2: Suzuki clutch

[0184]

[0185] A well-stirred mixture of 100 mmol (3), 120 mmol of the alkenyl BF3 K salt, 250 mmol cesium carbonate, 3 mmol palladium(II) acetate, 9 mmol triphenylphosphine, 1000 ml THF, and 200 ml water is heated under reflux for 16 h. After cooling, 500 ml of ethyl acetate (EE) is added, the aqueous phase is separated, the organic phase is washed three times with 300 ml of water and once with 200 ml saturated saline, and dried over magnesium sulfate. The mixture is filtered from the drying agent over a silica gel bed pre-flourished with EE, and the solvent is removed under vacuum. The residue is reacted further without further purification. Alternative procedure for step 3: Cyclization

[0186]

[0187] A well-stirred mixture of 100 mmol (11) and 400 g of polyphosphoric acid is heated to 90 °C for 1 h. Allowed to cool to 60 °C, the reaction mixture is poured, stirring well, into 5 l of ice water, stirred for 30 min, and the precipitated solid is filtered off by filtration or extracted with EE or dichloromethane (DCM). The crude product is recrystallized from DCM / acetonitrile or chromatographed. Alternative procedure for the introduction of BR-, SiR 2-, GeR 2-, NR-, S-bridges:

[0188] Example B1:

[0189]

[0190] Procedure analogous to S. Haig et al., Chem. Mat., 2011, 23(20), 4435. A mixture of 36.4 g (100 mmol) LS1, 14.6 g (220 mmol) malononitrile [109-77-3], 446 mg (5 mmol) β-alanine [107-95-9], 300 ml ethanol, and 200 ml dichloromethane (DCM) is stirred in a stirred autoclave for 3 h at 80 °C. The mixture is allowed to cool while stirring, the precipitated product is filtered off, the mixture is washed three times with 30 ml of cold ethanol each time, and dried under vacuum. Further purification is carried out by chromatography (Torrent column chromatography from A. Semrau) or hot extraction crystallization (common organic solvents, preferably acetonitrile or acetonitrile-DCM mixtures (4:1 - 1:2 vv)) and by fractional sublimation under high vacuum (p. ca. 10⁻⁵ < mbar). Yield: 31.9 g (77 mmol) 77%; Purity: ca. 99.9% n. HPLC.

[0191] Similarly, the following compounds can be prepared in the given yields over the 5 steps: Example. Starting materials product yield B2 16 % 34671-29-9 16807-11-7 666-52-4 B3 19 % 1008533-34-3 1686099-80-8 108-94-1 B4 22 % 54829-48-0 1686099-79-5 78-93-3 B5 20 % 3437-95-4 1628067-03-7 119-61-9 B6 21 % 37686-36-5 1357359-52-4 120-92-3 B7 7% 37686-36-5 2304744-36-1 1195-93-3 B8 19 % 37686-36-5 1438427-35-0 4477-17-2 B9 15 % 37686-36-5 2311845-06-2 119-60-8 B10 23 % 37686-36-5 2444315-80-2 700-58-3 B11 25 % 37686-36-5 2250435-63-1 700-58-3 B12 23 % 37686-36-5 2222130-32-5 486-25-9 B13 24 % 37686-36-5 2244888-30-8 2128-93-0 B14 18 % 37686-36-5 1838714-71-8 90-47-1 B15 16 % 37686-36-5 31609-96-8 1210-35-1 B16 11 % 37686-36-5 118044-75-0 82-05-3 B17 21 % 37686-36-5 2493276-29-0 700-58-3 B18 24 % 37686-36-5 16807-11-7 700-58-3 B19 23 % 37686-36-5 16807-11-7 120-92-3 B20 26 % 37686-36-5 1686099-80-8 108-94-1 B21 19 % 59163-68-7 2118984-35-1 96-22-0 B22 13 % 59163-68-7 16807-11-7 700-58-3 B23 11 % 59163-68-7 16807-11-7 120-92-3 B24 12 % 59163-68-7 1686099-80-8 108-94-1 B25 27 % 3437-95-4 1628067-03-7 666-52-4 B26 3437-95-4 27 % 1357359-52-4 67-64-1 B27 3437-95-4 30 % 1686099-80-8 67-64-1 B28 3437-95-4 32 % 1686100-42-4 67-64-1 B29 3437-95-4 32 % 1686099-79-5 67-64-1 B30 3437-95-4 26 % 1686100-43-5 67-64-1 B31 3437-95-4 31 % 1686100-44-6 67-64-1 B32 3437-95-4 27 % 1686100-44-6 108-94-1 B33 3437-95-4 30 % 1686100-44-6 700-58-3 B34 3437-95-4 30 % 1686100-44-6 119-61-9 B35 3437-95-4 32 % 2351179-71-8 67-64-1 B36 3437-95-4 33 % 1438427-35-0 67-64-1 B37 3437-95-4 25 % 1639452-47-3 67-64-1 B38 3437-95-4 30 % 2304744-36-1 67-64-1 B39 3437-95-4 14 % 845619-92-3 67-64-1 B40 3437-95-4 29 % 2393016-93-6 67-64-1 B41 3437-95-4 31 % 1628066-90-9 67-64-1 B42 3437-95-4 34 % 2619631-74-0 67-64-1 B43 3437-95-4 28 % 1628066-98-7 67-64-1 B44 3437-95-4 29 % 1628067-07-1 67-64-1 B45 3437-95-4 29 % 1628066-87-4 67-64-1 B46 3437-95-4 30 % 2088187-43-1 67-64-1 B47 3437-95-4 26 % 2311845-06-2 67-64-1 B48 3437-95-4 21 % 2118984-35-1 67-64-1 B49 3437-95-4 27 % 2209068-29-9 67-64-1 B50 3437-95-4 30 % 2209068-40-4 67-64-1 B51 3437-95-4 28 % 1628066-94-3 67-64-1 B52 3437-95-4 31 % 2097681-89-3 67-64-1 B53 3437-95-4 22 % 2097681-89-3 108-94-1 B54 3437-95-4 24 % 2097681-89-3 700-58-3 B55 3437-95-4 27 % 2097681-89-3 119-61-9 B56 3437-95-4 25 % 2097681-89-3 486-25-9 B57 3437-95-4 27 % 2364364-94-1 67-64-1 B59 3437-95-4 33 % 1807910-69-5 67-64-1 B60 3437-95-4 17 % 2796247-53-3 67-64-1 B61 3437-95-4 26 % 2624319-17-9 67-64-1 B62 3437-95-4 22 % 2444315-86-8 67-64-1 B63 3437-95-4 20 % 2444315-84-6 67-64-1 B64 3437-95-4 25 % 1370555-67-1 67-64-1 B65 3437-95-4 27 % 2660185-57-7 67-64-1 B66 3437-95-4 21 % 2450439-85-5 67-64-1 B67 3437-95-4 20 % 2636078-73-2 67-64-1 B68 3437-95-4 22 % 2636078-73-2 700-58-3 B69 3437-95-4 35 % 16807-11-7 67-64-1 B70 37686-36-5 30 % 1686099-80-8 67-64-1 B71 37686-36-5 32 % 1686100-42-4 67-64-1 B72 37686-36-5 26 % 1686100-43-5 67-64-1 B73 37686-36-5 30 % 1686100-44-6 119-61-9 B74 37686-36-5 35 % 1639452-47-3 67-64-1 B75 37686-36-5 28 % 1628066-90-9 67-64-1 B76 37686-36-5 29 % 1628066-98-7 67-64-1 B77 37686-36-5 27 % 2685783-06-4 67-64-1 B78 37686-36-5 27 % 1370555-67-1 67-64-1 B79 3437-95-4 25 % 2222130-32-5 67-64-1 B80 3437-95-4 23 % 2244888-30-8 67-64-1 B81 3437-95-4 19 % 1838714-71-8 67-64-1 B82 3437-95-4 22 % 31609-96-8 67-64-1 B83 3437-95-4 15 % 118044-75-0 67-64-1 B84 3437-95-4 24 $ 2493276-29-0 700-58-3 B85 37686-36-5 28 % 1686099-80-8 873-51-8 B86 3437-95-4 18 % 2493276-29-0 75-78-5 B87 3437-95-4 17 % 31609-96-8 1613-66-7 B88 37686-36-5 11 % 1639452-47-3 70278-00-1 B89 3437-95-4 14 % 1639452-47-3 10545-99-0 B90 3437-95-4 16 % 31609-96-8 10545-99-0 B100 17 % 37686-36-5 16807-11-7 666-52-4 20255-66-7 B101 15 % 37686-36-5 16807-11-7 666-52-4 26153-90-2 B102 19 % 37686-36-5 16807-11-7 666-52-4 611-74-5 B200 S1 45 % only step 5 100 °C / 5 h B201 S2 57 % only step 5 100 °C / 5 h B202 S3 53 % only step 5 100 °C / 5 h B203 S4 44 % only step 5 100 °C / 5 h B204 S5 41 % Step 5 only: 100 °C / 5 h B205 S6 53 % Step 5 only: 100 °C / 5 h B300 S100 49 % Step 5 only: 100 °C / 5 h B400 2201847-06-3 75 % only step 5 B401 2306103-34-2 77 % only step 5 B402 2306102-85-0 70 % only step 5 B403 2306102-60-9 70 % only step 5 Example B500:

[0192]

[0193] Instead of maleonitrile (H₂C(CN)₂), Example B1 can be carried out with 2-(4,5,5-trimethyl-2(5H)-furanylidene)-propanedinitrile or 2-(4,5,5-trimethyl-2(5H)-thiophenylidene)-propanedinitrile and their derivatives. Preparation: 36.4 g (100 mmol) of LS1 and 25.9 g (130 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene)-propanedinitrile [171082-32-9]. Yield: 34.5 g (63 mmol) 63%; Purity: approx. 99.9% by HPLC.

[0194] Similarly, the following compounds can be obtained in the specified yields. The 5 levels are shown: Example. Starting materials product yield B501 13 % 37686-36-5 2444315-80-2 700-58-3 171082-32-9 B502 17 % 37686-36-5 2222130-32-5 486-25-9 171082-32-9 B503 37686-36-5 33 % 1686099-80-8 67-64-1 171082-32-9 B504 37686-36-5 30 % 1639452-47-3 67-64-1 1274821-70-3 B505 16 % 37686-36-5 16807-11-7 666-52-4 20255-66-7 2244199-35-5 B506 S5 37 % only step 5 100 °C / 5 h 400760-72-7 B507 3437-95-4 19 % 16807-11-7 67-64-1 171082-32-9 B508 3437-95-4 17 % 1686099-80-8 67-64-1 1274821-70-3 B509 3437-95-4 1686099-79-5 67-64-1 383124-81-0 B510 3437-95-4 15 % 1686100-44-6 700-58-3 1290106-98-7 B511 3437-95-4 16 % 1438427-35-0 67-64-1 2790414-09-2 B512 3437-95-4 19 % 1639452-47-3 67-64-1 1274821-70-3 B513 3437-95-4 18 % 2619631-74-0 67-64-1 400760-72-7 B514 3437-95-4 17 % 2311845-06-2 67-64-1 1274821-70-3 B515 3437-95-4 20 % 2209068-40-4 67-64-1 1274821-70-3 B516 3437-95-4 16 % 2097681-89-3 108-94-1 1274821-70-3 B517 3437-95-4 15 % 2685783-06-4 67-64-1 400760-72-7 B518 3437-95-4 18 % 1370555-67-1 67-64-1 383124-81-0 B519 3437-95-4 16 % 2493276-29-0 700-58-3 1274821-70-3 B520 44 % 2201847-06-3 only step 5 1274821-70-3

[0195] Thermal stability of the compounds according to the invention: Table 1 summarizes the results of the thermal aging tests. For this test, 500 mg of compound B were sealed in a 20 ml Duran glass ampoule under vacuum (p ~ 10⁻⁴ < mbar) and then stored for 10 days at the specified temperature T (T = T - vacuum - TGA (5% weight loss + 40 °C)) in the absence of light. The ampoule was then opened, smelled, and its olfactory properties evaluated, as even minute quantities of volatile organo-sulfur, -selenium, and -tellurium compounds formed by thermal decomposition are easily recognizable by their characteristic rotten egg or radish odor. Furthermore, the purity was determined by HPLC and compared to that of the starting material, which had a purity > 99.9%. Table 1: Example. Connection B Temperature T Olfactory evaluation Purity HPLC TS1 B1 236 °C No unpleasant odor > 99.9 % TS2 B6 241 °C No unpleasant odor > 99.9 % TS3 B22 251 °C No unpleasant odor > 99.9 % TS4 B26 244 °C No unpleasant odor > 99.9 % TS5 B25 255 °C No unpleasant odor > 99.9 % TS6 B58 267 °C No unpleasant odor > 99.9 % TS7 B500 266 °C No unpleasant odor > 99.9 % TS8 B508 289 °C No unpleasant odor > 99.9 % Examples of photodiodes: 1) Production of mono-layer photodiodes (MLPDs) Device type 1:

[0196] Purified quartz substrates (15 min ultrasound in an acetone / isopropanol / water bath (1:1:1 v:v:v), then UV-ozone) are sputtered with a 150 nm thick indium tin oxide (ITO) anode. A 150 nm thick layer of the inventive compounds B and C 60 in a 1:1 volume ratio is then deposited under high vacuum by co-evaporation. Finally, a 10 nm thick ITO cathode is applied by sputtering. Subsequently, the IPCE (Incident Photon to Charge Carrier Efficiency) of the initial devices is determined at the absorption maximum in the wavelength range of 400–700 nm at a voltage of 10 V using a PTS-2-QE from Photonic Solutions (UK) (Table 2). The devices are then thermally exposed to temperatures of 180 °C for 10 minutes, after which IPCE is determined again. Table 2: Example. Connection IPCE (initial, %) IPCE (thermally aged 10 min. / 180 °C, %) D1 B1 70 68 D2 B100 75 72 Device type 2:

[0197] Purified quartz substrates (15 min ultrasonic treatment in an acetone / isopropanol / water bath (1:1:1 v:v:v), then UV-ozone) are sputtered with a 150 nm thick indium tin oxide (ITO) anode. A 30 nm thick layer of HTM2 (see Table 5) is then deposited under high vacuum, followed by an 80 nm thick layer of the inventive compounds B and C 60 in a 1:1 volume ratio, deposited by co-evaporation. A 1.5 nm thick ytterbium layer is then deposited. Finally, a 10 nm thick ITO cathode is applied by sputtering. Subsequently, the IPCE (Incident Photon to Charge Carrier Efficiency) of the initial devices is determined using a PTS-2-QE, Photonic Solutions (UK) at the maximum absorption in the wavelength range 400 - 700 nm at a voltage of 3 V (Table 3). Table 3: Example. Connection IPCE D10 B3 21 D11 B4 17 D12 B8 61 D13 B11 51 D14 B14 48 D15 B26 37 D16 B35 40 2) Production of bi-layer photodiodes (BLPDs)

[0198] Purified quartz substrates (15 min ultrasonic treatment in an acetone / isopropanol / water bath (1:1:1 v:v:v), then UV-ozone) are coated with a 150 nm thick indium tin oxide (ITO) anode via sputtering. All other materials are thermally evaporated in a vacuum chamber. The materials used to fabricate the BLPDs are shown in Table 5. Electron transport layer 2 (ETL2) can be produced by co-evaporating two materials. A specification such as ETM1:EIL (50:50) means that the co-evaporated layer contains 50 volume% of each of the individual materials. Structure of the BLPD:

[0199] ITO substrate BLPD hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 10 nm hole transport layer 1 (HTL1), see Table 4 hole transport layer 2 (HTL2), see Table 4 electron donor layer (EDL), see Table 4 electron acceptor layer (EAL), see Table 4 electron transport layer 1 (ETL1), see Table 4 electron transport layer 2 (ETL2), see Table 4 electron injection layer 1 (EIL1), 3 nm EIM cathode made of magnesium:silver (10:90), 100 nm

[0200] Subsequently, the IPCE (Incident Photon to Charge Carrier Efficiency) of the initial devices is determined using a PTS-2-QE, Photonic Solutions (UK) at the maximum absorption in the wavelength range 400-700 nm at a voltage of 3 V (Table 4). Table 4: Structure of Bi-Layer Photodiodes (BLPD) Example. HTL1 thickness HTL2 thickness EDL thickness EAL thickness ETL1 thickness ETL2 thickness IPCE % D30 HTM1 70 nm --- B1 15 nm EAM1 35 nm --- ETM2 30 nm 25 D31 HTM1 70 nm --- B5 15 nm EAM1 35 nm ETM1 5 nm ETM2 30 nm 19 D32 HTM1 50 nm HTM2 20 nm B12 15 nm EAM1 35 nm ETM1 5 nm ETM2 30 nm 24 D33 HTM1 50 nm HTM2 20 nm B18 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 29 D34 HTM1 50 nm HTM2 20 nm B19 10 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 36 D35 HTM1 50 nm HTM2 20 nm B23 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 39 D36 HTM1 50 nm HTM2 20 nm B27 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 28 D37 HTM1 50 nm HTM2 20 nm B31 10 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 27 D38 HTM1 50 nm HTM2 20 nm B37 10 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 32 D39 HTM1 50 nm HTM2 20 nm B45 10 nm EAM1 40 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 30 D40 HTM1 50 nm HTM2 20 nm B52 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 28 D41 HTM1 50 nm HTM2 20 nm B54 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 24 D42 HTM1 50 nm HTM2 20 nm B58 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 33 D43 HTM1 50 nm HTM2 20 nm B62 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 35 D44 HTM1 50 nm HTM2 20 nm B64 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 28 D45 HTM1 50 nm HTM2 20 nm B67 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 22 D46 HTM1 50 nm HTM2 20 nm B74 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 29 D47 HTM1 50 nm HTM2 20 nm B77 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIL (50:50) 30 nm 35 D48 HTM1 50 nm HTM2 20 nm B82 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 29 D49 HTM1 50 nm HTM2 20 nm B86 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 27 D50 HTM1 50 nm HTM2 20 nm B89 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 38 D51 HTM1 50 nm HTM2 20 nm B102 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 33 D52 HTM1 50 nm HTM2 20 nm B201 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 17 D53 HTM1 50 nm HTM2 20 nm B300 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 28 D54 HTM1 50 nm HTM2 20 nm B401 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 33 D55 HTM1 50 nm HTM2 20 nm B402 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 35 D56 HTM1 50 nm HTM2 20 nm B500 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 46 D57 HTM1 50 nm HTM2 20 nm B502 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 45 D58 HTM1 50 nm HTM2 20 nm B504 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 49 D59 HTM1 50 nm HTM2 20 nm B506 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 47 D60 HTM1 50 nm HTM2 20 nm B507 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 39 D61 HTM1 50 nm HTM2 20 nm B508 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 42 D62 HTM1 50 nm HTM2 20 nm B510 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 40 D63 HTM1 50 nm HTM2 20 nm B512 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 41 D64 HTM1 50 nm HTM2 20 nm B516 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 43 D65 HTM1 50 nm HTM2 20 nm B518 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 40 D66 HTM1 50 nm HTM2 20 nm B519 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 41 D67 HTM1 50 nm HTM2 20 nm B520 15 nm EAM1 35 nm ETM1 5 nm ETM1:EIM (50:50) 30 nm 44 Tabelle 5: Verwendete Materialien 2306796-00-7 1092356-32-5 HTM1 HTM2 64005-91-0 ETM1 EAM1 25387-93-3 1662-01-7 EIM ETM2

Claims

1. Compound comprising at least one structure of the formula (I): where the symbols used are as follows: Ara is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Ra radicals; Arb is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Rd radicals; Z is the same or different at each instance and is an alkenyl group having 2 to 40 carbon atoms, where the alkenyl group may be substituted by one or more Rd radicals, where one or more nonadjacent CH2 groups may be replaced by RdC=CRd, C=C, Si(Rd)2, C=O, C=S, C=Se, C=NR, C(=O)O, C(=O)NRd, NR, P(=O)(Rd), O, S, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more Rd radicals; at the same time, the group may form a ring system with a further group, for example an R or Rc group; with the proviso that the Z group has at least two CN groups; Y1 is the same or different at each instance and is O, S, Se, Te, NAr, NR, C(R)2, Ge(R)2, Si(R)2; Y2 is the same or different at each instance and is a bond, O, S, Se, Te, NAr, NRe, BAr, BRe, C(Re)2, Ge(Re)2, Si(Re)2, CRe=CRe, C=NRe, S=O, SO2; L is the same or different at each instance and is a connecting group, preferably a bond, C(R)2, O, S, NR, NAr, C(=O), BAr, B(R), Si(R)2, C=NR, C=C(R)2, S=O, SO2, P(R) and P(=O)R, -CR=CR- or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, R, Ra, Rb, Rc, Rd, Re group or a further group; R, Ra, Rb, Rc, Rd, Re is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R1)2, C(=O)N(Ar')2, C(=O)N(R1)2, C(Ar')3, C(R1)3 Si(Ar')3, Si(R1)3, B(Ar')2, B(R1)2, C(=O)Ar', C(=O)R1, P(=O)(Ar')2, P (=O)(R1)2, P(Ar')2, P(R1)2, S(=O)Ar', S(=O)R1, S(=O)2Ar' , S(=O)2R1, OSO2Ar' , OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C=CR1, C=C, Si(R1)2, C=O, C=S, C=Se, C=NR1, -C(=O)O-, -C(=O)NR1-, NR1, P(=O)(R1), -Se-, -Te-, Nar', BR1, Ge(R1)2, -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals; an arylthio or heteroarylthio group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or a diarylamino, arylheteroarylamino, diheteroarylamino group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl radical and may be substituted by one or more R1 radicals; at the same time, two R, Ra, Rb, Rc, Rd, Re radicals together or with a further group may also form a ring system; Ar' is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, at the same time, it is possible for two Ar' radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C=O, C=NR1, C=C(R1)2, O, S, S=O, SO2, N(R1), P(R1) and P(=O)R1; R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R2)2, C(=O)Ar", C(=O)R2, P(=O)(Ar")2, P(Ar")2, B(Ar")2, B(R2)2, C(Ar")3, C(R2)3, Si(Ar")3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, C=O, C=S, C=Se, C=NR2, C(=O)O, C(=O)NR2, NR2, P(=O)(R2), O, S, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems; at the same time, two or more R1 radicals together may form a ring system; at the same time, one or more R1 radicals may form a ring system with another part of the compound; Ar" is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R2 radicals, at the same time, it is possible for two Ar" radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C=O, C=NR2, C=C(R2)2, O, S, S=O, SO2, N(R2), P(R2) and P(=O)R2; R2 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R2 together may form a ring system.

2. Compound according to Claim 1, characterized in that the Z group is or comprises a substructure of the formula (Z-1) or (Z-2): where Rd and R1 have the definition given in Claim 1, the dashed bond represents the site of attachment, and in addition: X is O, S or Se; p is 0, 1 or 2.

3. Compound according to Claim 1 or 2, comprising at least one structure of the formula (II) or (IIa): where the symbols Ara, Arb, Rc, Rd, Y1, Y2, R1 and L have the definitions given in Claim 1, and X and p the definitions given in Claim 2.

4. Compound according to one or more of Claims 1 to 3, comprising at least one structure of the formula (III) or (IIIa) : where the symbols Rc, Rd, Y1, Y2, R1 and L have the definitions given in Claim 1, and X and p the definitions given in Claim 2, and the other symbols are defined as follows: Xa is the same or different at each instance and is N or CRa, with the proviso that not more than two of the Xa groups in one cycle are N, where R2 has the definition detailed in Claim 1; or two adjacent Xa together are a group of the following formula: where the dashed bonds represent the linkage of the group within the structure; Xb is the same or different at each instance and is N or CRb, with the proviso that not more than two of the Xb groups in one cycle are N, where Rd has the definition detailed in Claim 1; or two adjacent Xb together are a group of the following formula: where the dashed bonds represent the linkage of the group within the structure.

5. Compound according to one or more of Claims 1 to 4, comprising at least one structure of the formula (IV) or (IVa) to (IVf): where the compounds may also be partly or fully deuterated, the symbols Ra, Rb, Rc, Rd, Y1, Y2 and L have the definitions given in Claim 1, Z has the definitions given in Claim 2, and the other symbols are defined as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3.

6. Compound according to one or more of Claims 1 to 5, characterized in that the L group is a bond, C(R)2, O, S, NAr or NR, the Y2 group is C(Re)2 and the Y1 group is O, S, Se, Te, NR, NAr, preferably S or Se.

7. Compound according to one or more of Claims 1 to 6, characterized in that the Re radical of the Y2 group is a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 12 carbon atoms, where the alkyl group may be substituted in each case by one or more R1 radicals, or an aryl or heteroaryl group which has 5 to 12 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, where the two Re radicals of the Y2 group may together form a ring which has 5 to 10 ring atoms and may be substituted by one or more R1 radicals.

8. Compound according to one or more of Claims 1 to 7, characterized in that the Rc radical is H, D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 12 carbon atoms, where the alkyl group may be substituted in each case by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C=CR1, C=C, Si(R1)2, C=O, C=S, C=Se, C=NR1, C(=O)O, C(=O)NR1, NR1, P(=O)(R1), O, S, SO or SO2, or an aryl or heteroaryl group which has 5 to 12 aromatic ring atoms and may be substituted by one or more R1 radicals, where the Rc radical together with the Rd radical may form a ring which has 5 to 10 ring atoms and may be substituted by one or more R1 radicals.

9. Compound according to one or more of Claims 1 to 8, comprising at least one structure of the formulae (V-1) to (V-80) : where the symbols R2, Rb, Rc, Rd, Re, Y2 and L have the definitions given in Claim 1, Z has the definitions given in Claim 2, and the other symbols are defined as follows: G is the same or different at each instance and is O, S, Se, Te, Nar', NR1, BR1, C(R1)2, Ge(R1)2, Si(R1)2, -C(R1)2-(CR1)2-, -CR1=CR1-, C=NR1, S=O, SO2 or an ortho-linked arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R1 radicals, where the R1 radical has the definition given in Claim 1; Y3 is the same or different at each instance and is a bond, O, S, Se, Te, Nar', NR1, BR1, C(R1)2, Ge(R1)2, Si(R1)2, CR1=CR1, C=NR1, S=O, SO2 or an ortho-linked arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R1 radicals, where the R1 radical has the definition given in Claim 1; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; s is 0, 1, 2, 3, 4, 5 or 6; m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3.

10. Oligomer, polymer or dendrimer containing one or more compounds according to any of Claims 1 to 9, wherein, in place of a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

11. Formulation containing at least one compound according to one or more of Claims 1 to 9 or an oligomer, polymer or dendrimer according to Claim 10 and at least one further compound, where the further compound is preferably selected from one or more solvents and / or from at least one further compound selected from the group consisting of electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials, preferably electron transport materials, electron injection materials, hole blocker materials, more preferably subphthalocyanines, subphthalocyanine derivatives, fullerenes or fullerene derivatives.

12. Process for preparing a compound according to one or more of Claims 1 to 9, characterized in that a base skeleton having an aromatic amino group is synthesized and at least one heterocyclic radical is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

13. Use of a compound according to one or more of Claims 1 to 9 or of an oligomer, polymer or dendrimer according to Claim 10 in an electronic device, preferably as photosensitizer.

14. Electronic device comprising at least one compound according to one or more of Claims 1 to 9 or an oligomer, polymer or dendrimer according to Claim 10.

15. Electronic device according to Claim 14, characterized in that the compound according to one or more of Claims 1 to 9 or the oligomer, polymer or dendrimer according to Claim 10 is used as photosensitizer in a light-absorbing layer.