Materials for organic light-emitting devices

Abstract

The present application relates to compounds represented by Formula (1), to processes for preparing such compounds, OLED materials containing such compounds, and to electronic devices comprising one or more such compounds, and to the use of such compounds in electronic devices, in particular organic light-emitting devices.

Description

[0001] Foreignfiling text P24-238-SEC-WO01 20251111

[0002] - 1 -

[0003] Materials for organic light-emitting devices

[0004] Field of the Invention

[0005] The present invention relates to compounds represented by Formula (1), to processes for

[0006] 5 preparing such compounds, to electronic devices comprising one or more such compounds, and to the use of such compounds in electronic devices, in particular organic light-emitting devices.

[0007] Background of the Invention

[0008] Electronic devices in the context of this application are understood to mean what are called organic electronic devices, which comprise organic semiconductor materials as functional materials. More particularly, these are understood to mean OLEDs (organic electroluminescent devices). The term OLEDs is understood to mean electronic devices which have one or more layers comprising organic compounds and emit light on

[0009] 15 application of electrical voltage. The construction and general principle of function of OLEDs are known to those skilled in the art.

[0010] In electronic devices, especially OLEDs, there is great interest in an improvement in the performance data. In these aspects, it has not yet been possible to find any entirely

[0011] 20 satisfactory solution.

[0012] A great influence on the performance data of electronic devices is possessed by emission layers and layers having a hole-transporting function. Novel compounds are also being sought for use in these layers, especially hole-transporting compounds and compounds

[0013] 25 that can serve as hole-transporting matrix material, especially for phosphorescent emitters, in an emitting layer. For this purpose, there is a search especially for compounds that have a high glass transition temperature, high stability, and high conductivity for holes. A high stability of the compound is a prerequisite for achieving a long lifetime of the electronic device. There is moreover a need to find compounds whose use in electronic devices results in improvement of the performance data of the devices, especially in a high efficiency, a long lifetime and a low operating voltage, a low lateral leakage current, e.g. leakage current to neighboring pixels that are switched off, as described for example in more detail in WO 2024 / 133366. Additionally, an improved capacitance / voltage signal is often desired, in particular being of great importance for the general charging behaviour of

[0014] 35 an OLED. Foreignfiling text P24-238-SEC-WO01 20251111

[0015] - 2 -

[0016] In the prior art, spiroalkyl derivative is known as hole-transporting materials and holetransporting matrix materials for electronic devices. However, there remains room for improvement in respect of the abovementioned properties.

[0017] 5 CN 107892650 B describe the indenofluorenamines with 9.9- spirobifluorene as a hole transport material.

[0018] CN 117186104 A describes the indenofluorenamines as as a hole transport material.

[0019] It has now been found that the indenofluorenamines of the formula below, which are characterized by a particular structure, are of excellent suitability for use in electronic devices. They are especially suitable for use in OLEDs, and even more particularly therein for use as hole transport materials and for use as hole-transporting matrix materials, especially for phosphorescent emitters. The compounds lead to high lifetime, high

[0020] 15 efficiency and low operating voltage of the devices, while having improved capacitance and charging behavior. Further preferably, the compounds found have a high glass transition temperature, high thermal stability, low sublimation temperature, good solubility, good synthetic accessibility and high conductivity for holes.

[0021] 20 The particular combination of the spiroalkly moiety and the indenofluorene moiety, bonded to the amine nitrogen, has been found to lead to a low HOMO energy, and overall favorable properties as OLED material. This makes them particularly suitable for use in an electron blocking layer of an OLED, preferably in one of two electron blocking layers layers which are in contact with each other, more preferably in the one of the two electron

[0022] 25 blocking layers, which is in contact with the emitting layer.

[0023] In particular, the compounds are characterized by their property to cause an improved capacitance of the OLED, particularly when used in an electron blocking layer, more particularly when used in an OLED stack which has two electron blocking layers which are adjacent to each other, where one of the two electron blocking layers, preferably the one which is in contact with the emitting layer, comprises a compound according to the invention, and the other comprises a compound with a chemical structure which is not according to the invention. Further, OLEDs comprising the compounds show only a small voltage increase over their lifetime, particularly when the compounds are used in an

[0024] 35 electron blocking layer, more particularly when used in an OLED stack which has two electron blocking layers which are adjacent to each other, where one of the two electron blocking layers, preferably the one which is in contact with the emitting layer, comprises a Foreignfiling text P24-238-SEC-WO01 20251111

[0025] - 3 - compound according to the invention, and the other comprises a compound with a chemical structure which is not according to the invention. Further, OLEDs comprising the compounds show only a small leakage current, particularly when the compounds are used in an electron blocking layer, more particularly when used in an OLED stack which has

[0026] 5 two electron blocking layers which are adjacent to each other, where one of the two electron blocking layers, preferably the one which is in contact with the emitting layer, comprises a compound according to the invention, and the other comprises a compound with a chemical structure which is not according to the invention.

[0027] Summary of the Invention

[0028] The present invention therefore first provides a compound represented by Formula (1):

[0029] 25 Formula (1) where the groups and indices that occur are as follows:

[0030] X is O, S or a single bond;

[0031] Y is O, S or a single bond; wherein X and Y are not both single bonds;

[0032] 35 R1stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(R4)2, C(=O)R4, P(=O)(R4)2, S(=O)R4, S(=O)2R4, NO2, Si(R4)3, B(OR4)2, OSO2R4, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic Foreignfiling text P24-238-SEC-WO01 20251111

[0033] - 4 - alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2 groups may be replaced by R4C=CR4, C=C, Si(R4)2, Ge(R4)2, Sn(R4)2, C=O, C=S, C=Se, P(=O)(R4), SO, SO2, O, S or CONR4and where one or more H atoms may be replaced by

[0034] 5 D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy group having 5 to 60 ring atoms, which may be substituted by one or more radicals R4, wherein two of radicals R1may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R4;

[0035] R2and R3stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(R5)2, C(=O)R5, P(=O)(R5)2, S(=O)R5, S(=O)2R5, NO2, Si(R5)3, B(OR5)2, OSO2R5, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted

[0036] 15 by one or more radicals R5, where in each case one or more non-adjacent CH2groups may be replaced by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, P(=O)(R5), SO, SO2, O, S or CONR5and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R5, or an aryloxy

[0037] 20 group having 5 to 60 ring atoms, which may be substituted by one or more radicals R5, wherein two of radicals R2or R3may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R5;

[0038] Ar1stands for an aromatic or heteroaromatic ring system having 5 to 60 ring atoms,

[0039] 25 which may in each case also be substituted by one or more radicals R6;

[0040] L1and L2stand on each occurrence, identically or differently, for a single bond, an aromatic having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R7; n1 and n2 stand on each occurrence, identically or differently, for an integer selected from O to 3;

[0041] R4, R5, R6and R7stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2,

[0042] 35 OSO2R , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R', where in each case one or more non- Foreignfiling text P24-238-SEC-WO01 20251111

[0043] - 5 - adjacent CH2 groups may be replaced by R'C=CR', C=C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S or CONR' and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R', or an

[0044] 5 aryloxy group having 5 to 60 ring atoms, which may be substituted by one or more radicals R', where two of radicals R4, R5, R6and R7may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R';

[0045] Ar stands on each occurrence, identically or differently, for an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may in each case also be substituted by one or more radicals R';R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C

[0046] 15 atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

[0047] The invention further provides a process for preparing a compound represented by

[0048] 20 Formula (1) as described above or described in following preferece.

[0049] The invention further provides a formulation containing at least one compound represented by Formula (1) as described above or described in following preference and at least one solvent.

[0050] 25

[0051] The invention further provides an electronic device containing at least one compound represented by Formula (1) as described above or described in following preferece.

[0052] The invention further provides the use of a compound represented by Formula (1) as described above or described in following preferece in an electronic device.

[0053] Detailed Description of the Invention

[0054] "D" or "D-atom" in the context of this invention means deuterium.

[0055] 35

[0056] The following definitions apply to the chemical groups used as general definitions. They apply insofar as no more specific definitions are given. Foreignfiling text P24-238-SEC-WO01 20251111

[0057] - 6 -

[0058] An aryl group in the context of this invention contains 6 to 60 ring atoms, preferably carbon atoms. A heteroaryl group in the context of this invention contains 5 to 60 ring atoms, where the ring atoms include carbon atoms and at least one heteroatom, with the

[0059] 5 proviso that the sum total of carbon atoms and heteroatoms adds up to at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood here to mean either a simple aromatic cycle, i.e. phenyl, derived from benzene, or a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a fused aryl or heteroaryl group, for example derived from naphthalene, anthracene, phenanthrene, quinoline or isoquinoline. An aryl group having 6 to 18 carbon atoms is therefore preferably phenyl, naphthyl, phenanthryl or triphenylenyl, with no restriction in the attachment of the aryl group as substituent. The aryl or heteroaryl group in the context of this invention may bear one or more R radicals, where the substituent R is described below.

[0060] 15

[0061] An aromatic ring system in the context of this invention contains 6 to 60 ring atoms in the ring system. The aromatic ring system also includes aryl groups as described above. An aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and triphenylenyl.

[0062] 20

[0063] A heteroaromatic ring system in the context of this invention contains 5 to 60 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 10 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system also includes heteroaryl groups as described above. The heteroatoms in the heteroaromatic ring system

[0064] 25 are preferably selected from N, O and / or S.

[0065] An aromatic or heteroaromatic ring system in the context of this invention is understood to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which it is also possible for a plurality of aryl or heteroaryl groups to be interrupted by a nonaromatic unit (preferably less than 10% of the atoms other than H), for example a carbon, nitrogen or oxygen atom or a carbonyl group. For example, systems such as 9,9'- spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. shall thus also be regarded as aromatic or heteroaromatic ring systems in the context of this invention, and likewise systems in which two or more aryl groups are interrupted, for example, by a

[0066] 35 linear or cyclic alkyl group or by a silyl group. In addition, systems in which two or more aryl or heteroaryl groups are bonded directly to one another, for example biphenyl, Foreignfiling text P24-238-SEC-WO01 20251111

[0067] - 7 - terphenyl, quaterphenyl or bipyridine, are likewise encompassed by the definition of the aromatic or heteroaromatic ring system.

[0068] An aromatic or heteroaromatic ring system which has 5 to 60 ring atoms and may be

[0069] 5 joined to the aromatic or heteroaromatic system via any desired positions is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans- monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine,

[0070] 15 phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1 ,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine,

[0071] 20 benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7- diazapyrene, 2,3-diazapyrene, 1 ,6-diazapyrene, 1 ,8-diazapyrene, 4,5-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1 ,2,3-triazole, 1 ,2,4- triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1 ,2,5-oxadiazole, 1,3,4-

[0072] 25 oxadiazole, 1 ,2,3-thiadiazole, 1 ,2,4-thiadiazole, 1 ,2,5-thiadiazole, 1,3,4-thiadiazole, 1 ,3,5- triazine, 1 ,2,4-triazine, 1 ,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1 , 2,3,5- tetrazine, purine, pteridine, indolizine and benzothiadiazole.

[0073] The abbreviation Ar at each instance is in each case independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms and may be substituted by one or more R' radicals or heteroaromatic ring system having 5 to 24 ring atoms and may be substituted by one or more R' radicals, where the details for the aromatic ring system or heteroaromatic ring system apply here correspondingly. The R’ radical or the R’ radicals has / have a definition as described above or described hereinafter. The abbreviation Ar at

[0074] 35 each instance is preferably in each case independently an aryl group which has 6 to 40 ring atoms and may be substituted by one or more R’ radicals, or a heteroaryl group having 5 to 40 ring atoms and containing O or S as heteroatom, which may be substituted Foreignfiling text P24-238-SEC-WO01 20251111

[0075] - 8 - by one or more R’ radicals, where the details for the aryl group or heteroaryl group and R’ as described above or hereinafter are applicable correspondingly.

[0076] The abbreviation Ar1and Ar2are the same or different at each instance and are an

[0077] 5 aromatic or heteroaromatic ring system which has 5 to 60 ring atoms and may be substituted by one or more R5radicals, where the R5radical or the substituents R5has / have a definition as described above or hereinafter. Preferably, Ar1and Ar2are the same or different at each instance and are an aryl group having 6 to 40 ring atoms as described above.

[0078] A cyclic alkyl, alkoxy or thioalkyl group in the context of this invention is understood to mean a monocyclic, bicyclic or polycyclic group.

[0079] In the context of the present invention, a straight-chain alkyl group having 1 to 40 C

[0080] 15 atoms, branched or cyclic alkyl group having 3 to 40 C atoms is understood to mean, for example, the methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n- hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2- methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-

[0081] 20 octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6- dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2- trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1 , 1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1 ,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1- dimethyl-n-hexadec-1-yl, 1 ,1-dimethyl-n-octadec-1-yl, 1 , 1-diethyl-n-hex-1-yl, 1 , 1-diethyl-n-

[0082] 25 hept-1-yl, 1 , 1-diethyl-n-oct-1-yl, 1 , 1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl, 1,1- diethyl-n-tetradec-1-yl, 1 ,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n- propyl)cyclohex-1-yl, 1-(n-butyl)cyclohex-1-yl, 1-(n-hexyl)cyclohex-1-yl, 1-(n- octyl)cyclohex-1-yl and 1-(n-decyl)cyclohex-1-yl radicals.

[0083] A straight-chain alkoxy group having 1 to 40 C atoms or branched alkoxy group having 3 to 40 C atoms is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n- propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

[0084] A straight-chain thioalkyl group having 1 to 40 C atoms is understood to mean, for

[0085] 35 example, S-alkyl groups, for example thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n- propyl, 1-thio-i-butyl, 1-thio-n-butyl or 1 -thio-t-butyl. Foreignfiling text P24-238-SEC-WO01 20251111

[0086] - 9 -

[0087] An aryloxy or heteroaryloxy group having 5 to 60 ring atoms means O-aryl or O-heteroaryl and means that the aryl or heteroaryl group is bonded via an oxygen atom, where the aryl or heteroaryl group is defined as described above.

[0088] 5 An aralkyl or heteroaralkyl group having 5 to 40 ring atoms means that an alkyl group as described above is substituted by an aryl group or heteroaryl group, where the aryl or heteroaryl group is defined as described above.

[0089] The wording that two or more radicals together may form a ring, in the context of the present description, shall be understood to mean, inter alia, that the two radicals are joined to one another by a chemical bond. This is illustrated by the following scheme:

[0090] In addition, however, the abovementioned wording shall also be understood to mean that, if one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring. This shall be illustrated by the following

[0091] 20 scheme:

[0092] 25

[0093] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein the compound satisfies one of conditions A to C <Condition A>

[0094] X is O or S; and Y is a single bond

[0095] <Condition B>

[0096] X is a single bond; and Y is O or S

[0097] <Condition C>

[0098] X is O or S; and Y is O or S.

[0099] 35

[0100] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0101] - 10 - represented by Formula (1), wherein wherein the compound represented by at least one of Formulae 1-1 to 1-4:

[0102] 5

[0103] 15

[0104] 20

[0105] 25 wherein X is O or S, Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given above or given hereinafter.

[0106] 35 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0107] - 11 - represented by Formula (1), wherein the compound represented by at least one of

[0108] Formulae 1-A-1 to 1-A-4:

[0109] 5

[0110] 15

[0111] 20

[0112] 25 wherein X is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given above or given hereinafter.

[0113] 35 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0114] - 12 - represented by Formula (1), wherein the compound represented by at least one of

[0115] Formulae 1-B-1 to 1-B-4:

[0116] 5

[0117] 15

[0118] 20

[0119] 25 wherein Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given above or given hereinafter.

[0120] 35 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0121] - 13 - represented by Formula (1), wherein the compound represented by at least one of

[0122] Formulae 1-C-1 to 1-C-4:

[0123] 5

[0124] 15

[0125] 20

[0126] 25 wherein X is O or S, Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given above or given hereinafter.

[0127] 35 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0128] - 14 - represented by Formula (1), wherein R1stands on each occurrence, identically or differently, for a straight-chain alkyl group having 1 to 40 C atoms or branched alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each

[0129] 5 case be substituted by one or more radicals R4, wherein two of radicals R1may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R4; wherein R4has the definition given above or given hereinafter. Preferably, R1stands on each occurrence, identically or differently, for methyl or phenyl group, which may be substituted by one or more radicals R4; wherein R4has the definition given above or given hereinafter.

[0130] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein R2and R3stand on each occurrence, identically or

[0131] 15 differently, for H, D, a straight-chain alkyl group having 1 to 40 C atoms or branched alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R5, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R5, wherein two of radicals R2or R3may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be

[0132] 20 substituted by one or more radicals R5; wherein R5has the definition given above or given hereinafter. Preferably, R2and R3stand on each occurrence, identically or differently, for H, D, methyl, t-butyl, phenyl, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene or 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran,

[0133] 25 dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, or triazine group, which may be substituted by one or more radicals R5; wherein R5has the definition given above or given hereinafter. More preferably, R2and R3stand on each occurrence, identically or differently, for H, D, methyl or t-butyl group, which may be substituted by one or more radicals R5; wherein R5has the definition given above or given hereinafter. Particularly preferably, R2and R3stand on each occurrence, identically or differently, for H or D.

[0134] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound

[0135] 35 represented by Formula (1), wherein L1and L2are selected, identically or differently at each occurrence, from a single bond; and a divalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'- Foreignfiling text P24-238-SEC-WO01 20251111

[0136] - 15 - dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, where each of which may be substituted by one or more R7

[0137] 5 radicals; R7has the definition given above or given hereinafter. Preferably, L1and L2are selected, identically or differently at each occurrence, from a single bond; and a divalent groups derived from benzene and biphenyl, where each of which may be substituted by one or more R7radicals; R7has the definition given above or given hereinafter.

[0138] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), L1and L2at each instance are each independently a single bond; or represented by one of Formulae ArL-1 to ArL-96; preferrably, a single bond; or

[0139] 15 represented by one of Formulae ArL-1 to ArL-3 and ArL-79:

[0140] 20

[0141] 25

[0142] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0143] 5

[0144] 15

[0145] 20

[0146] 25

[0147] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0148] - 17 -

[0149] 5

[0150] 15

[0151] 20

[0152] 25

[0153] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0154] 5

[0155] 15

[0156] 20

[0157] 25

[0158] 35 Foreignfiling text P24-238-SEC-WO01 20251111 Foreignfiling text P24-238-SEC-WO01 20251111

[0159] - 20 -

[0160] 5

[0161] 15

[0162] 20

[0163] 25 in Formulae ArL-1 to ArL-96, the dashed lines are attachments to the corresponding residue of Formula (1); each of Formulae ArL-1 to ArL-96 may be substituted by R7, and preferably have only H in

[0164] 35 the positions shown as unsubstituted, or partly or fully D instead of H in the positions shown as unsubstituted;

[0165] R7has the definition given above or given hereinafter; Foreignfiling text P24-238-SEC-WO01 20251111

[0166] - 21 - wherein two of radicals R7may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R’; and R’ has the definition given above or given hereinafter.

[0167] 5 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein L1and L2stand on each occurrence, identically or differently, for a single bond or divalent groups derived from benzene, which may be substituted by one or more radicals R7; wherein R7has the definition given above or given hereinafter.

[0168] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein R4, R5, R6and R7stand on each occurrence,

[0169] 15 identically or differently, for H, D, a straight-chain alkyl group having 1 to 40 C atoms or branched alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R', or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R', where two of radicals R4, R5, R6and R7may form a mono- or polycyclic, aliphatic ring system or aromatic ring

[0170] 20 system, which may be substituted by one or more radicals R'; wherein R‘ has the definition given above or given hereinafter. Preferably, R4, R5, R6and R7stand on each occurrence, identically or differently, for H, D, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, phenyl, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene or 9,9'-diphenylfluorene,

[0171] 25 benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, or triazine group, which may be substituted by one or more radicals R'; wherein R' has the definition given above or given hereinafter.

[0172] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein that Ar1stands on each occurrence, identically or differently, for benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene,

[0173] 35 fluorene, in particular 9,9'-dimethylfluorene or 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, spiroxanthene, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzonaphthofuran, Foreignfiling text P24-238-SEC-WO01 20251111

[0174] - 22 - benzothiophene or indole, which may in each case also be substituted by one or more radicals R6; R6has the definition given above or given hereinafter.

[0175] In one embodiment of the compound represented by Formula (1) or preferred

[0176] 5 embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), Ar1is selected, identically or differently at each occurrence, from groups of the following Formulae Ar1-1 to Ar1-282:

[0177] 15

[0178] 20

[0179] 25

[0180] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0181] -23-

[0182] 5

[0183] 15

[0184] 20

[0185] 25

[0186] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0187] -24-

[0188] 5

[0189] 15

[0190] 20

[0191] 25

[0192] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0193] -25-

[0194] 5

[0195] 15

[0196] 20

[0197] 25

[0198] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0199] -26-

[0200] 5

[0201] 15

[0202] 20

[0203] 25

[0204] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0205] -27-

[0206] 5

[0207] 15

[0208] 20

[0209] 25

[0210] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0211] -28-

[0212] 5

[0213] 15

[0214] 20

[0215] 25

[0216] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0217] -29-

[0218] 5

[0219] 15

[0220] 20

[0221] 25

[0222] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0223] 5

[0224] 15

[0225] 20

[0226] 25

[0227] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0228] - 31 -

[0229] 5

[0230] 15

[0231] 20

[0232] 25

[0233] 35

[0234] Foreignfiling text P24-238-SEC-WO01 20251111

[0235] - 33 -

[0236] 5

[0237] 15

[0238] 20

[0239] 25

[0240] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0241] - 34 -

[0242] 5

[0243] 15

[0244] 20

[0245] 25

[0246] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0247] - 35-

[0248] 5

[0249] 15

[0250] 20

[0251] 25

[0252] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0253] 5

[0254] 15

[0255] 20

[0256] 25 Foreignfiling text P24-238-SEC-WO01 20251111

[0257] - 37 -

[0258] 5

[0259] 15 where the dotted line represents the bond to the nitrogen atom and where the groups at

[0260] 20 the positions shown as unsubstituted may be substituted by R6radicals, and preferably have only H in the positions shown as unsubstituted, or partly or fully D instead of H in the positions shown as unsubstituted.

[0261] In one embodiment of the compound represented by Formula (1) or preferred

[0262] 25 embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein the compound represented by Formula (1) comprises at least one deuterium.

[0263] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein the compound may be partly or fully substituted by deuterium.

[0264] In one embodiment of the compound represented by Formula (1) or preferred

[0265] 35 embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0266] - 38 - represented by Formula (1), wherein the compound satisfies at least one of Conditions 1- 1 to 1-6:

[0267] <Condition 1-1 >

[0268] At least one of R1comprises at least one of deuterium

[0269] 5 <Condition 1-2>

[0270] At least one of R2comprises at least one of deuterium

[0271] <Condition 1-3>

[0272] At least one of R3comprises at least one of deuterium

[0273] <Condition 1-4>

[0274] Ar1comprises at least one of deuterium

[0275] <Condition 1-5>

[0276] L1comprises at least one of deuterium

[0277] <Condition 1-6>

[0278] L2comprises at least one of deuterium.

[0279] 15

[0280] In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound represented by Formula (1), wherein the compound satisfies at least one of Conditions 2- 1 to 2-7:

[0281] 20 <Condition 2-1 > at least one of R1is deuterium

[0282] <Condition 2-2> at least one of R2is deuterium

[0283] <Condition 2-3>

[0284] 25 at least one of R3is deuterium

[0285] <Condition 2-4> at least one of R4is deuterium

[0286] <Condition 2-5> at least one of R5is deuterium.

[0287] <Condition 2-6> at least one of R6is deuterium.

[0288] <Condition 2-7> at least one of R7is deuterium.

[0289] 35 In one embodiment of the compound represented by Formula (1) or preferred embodiments of the hole-transfering material comprising at least one compound Foreignfiling text P24-238-SEC-WO01 20251111

[0290] - 39 - represented by Formula (1), wherein the compound satisfies at least one of Conditions 3- 1 to 3-7:

[0291] <Condition 3-1 > all R1is deuterium

[0292] 5 <Condition 3-2> all R2is deuterium

[0293] <Condition 3-3> all R3is deuterium

[0294] <Condition 3-4> all R4is deuterium

[0295] <Condition 3-5> all R5is deuterium

[0296] <Condition 3-6> all R6is deuterium

[0297] 15 <Condition 3-5> all R7is deuterium.

[0298] The following compounds are examples of compounds represented by Formula (1):

[0299] 20

[0300] 25

[0301] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0302] -40-

[0303] 5

[0304] 15

[0305] 20

[0306] 25

[0307] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0308] - 41 -

[0309] 5

[0310] 10

[0311] 15

[0312] 20

[0313] 25

[0314] 30

[0315] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0316] - 42 -

[0317] 5

[0318] 15

[0319] 20

[0320] The compounds according to formula (1) may be prepared by synthesis methods such as oxidation, nucleophilic addition / substitution reaction, Buchwald coupling and Suzuki

[0321] 25 coupling. The skilled person is aware of several possible synthetic routes, based on his general knowledge of organic synthetic chemistry.

[0322] The present application thus provides a process for preparing a compound according to the present application, characterized in that 1) in the case of an aryl linker, introduction of the amine with the linker by Suzuki reaction 2) introduction of substituted or unsubstituted aromatic group, by Buchwald reaction 3) introduction of a secondary amine by Buchwald reaction.

[0323] In one embodiment, a process for preparing a compound represented by Formula (1),

[0324] 35 characterized in that a fluorenyl compound which carries at least one reactive group is either a) reacted in a Buchwald reaction with a secondary amine , or b) is reacted in a Foreignfiling text P24-238-SEC-WO01 20251111

[0325] - 43 -

[0326] Suzuki reaction with a boronic acid-substituted tertiary amine, or c) in a sequence of first i) Suzuki reaction with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound, and then ii) Buchwald reaction of the resulting intermediate with a secondary amine.

[0327] 5

[0328] By following these procedures, if necessary, by purification, such as re-crystallization or sublimation, the compounds represented by Formula (1) can be obtained in high purity, preferably more than 99.9% (determined by1H NMR and / or HPLC).

[0329] For the processing of the compounds of the invention from a liquid phase, for example by spin-coating or by printing methods, formulations of the compounds of the invention are required. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferable to use mixtures of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl

[0330] 15 benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene,

[0331] 1.2.4.5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2- phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole,

[0332] 3.5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate,

[0333] 20 cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetole, 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

[0334] 25 dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1 ,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0335] The present invention likewise further provides a formulation, especially a solution, dispersion or emulsion, comprising at least one compound of the invention, as described above, or a mixture of the invention, as described above, and at least one solvent, preferably an organic solvent. The way in which such solutions can be prepared is known to those skilled in the art.

[0336] The compound represented by Formula (1) is suitable for use in an electronic device,

[0337] 35 especially an organic electroluminescent device (OLED). Depending on the substitution, the compound represented by Formula (1) can be used in different functions and layers. Preference is given to use as a hole-transporting material in a hole-transporting layer Foreignfiling text P24-238-SEC-WO01 20251111

[0338] - 44 - and / or as matrix material in an emitting layer, more preferably in combination with a phosphorescent emitter.

[0339] The invention therefore further provides for the use of a compound represented by

[0340] 5 Formula (1) in an electronic device. This electronic device is preferably selected from the group consisting of organic integrated circuits (OlCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and more preferably organic electroluminescent devices (OLEDs).

[0341] The invention further provides an electronic device comprising at least one compound represented by Formula (1). This electronic device is preferably selected from the

[0342] 15 abovementioned devices.

[0343] Particular preference is given to an organic electroluminescent device comprising anode, cathode and at least one emitting layer, characterized in that at least one organic layer comprising at least one compound represented by Formula (1) is present in the device.

[0344] 20 Preference is given to an organic electroluminescent device comprising anode, cathode and at least one emitting layer, characterized in that at least one organic layer in the device, selected from hole-transporting and emitting layers, comprises at least one compound represented by Formula (1).

[0345] 25 A hole-transporting layer is understood here to mean all layers disposed between anode and emitting layer, preferably hole injection layer, hole transport layer and electron blocker layer. A hole injection layer is understood here to mean a layer that directly adjoins the anode. A hole transport layer is understood here to mean a layer which is between the anode and emitting layer but does not directly adjoin the anode, and preferably does not directly adjoin the emitting layer either. An electron blocker layer is understood here to mean a layer which is between the anode and emitting layer and directly adjoins the emitting layer. An electron blocker layer preferably has a high-energy LIIMO and hence prevents electrons from exiting from the emitting layer.

[0346] 35 Apart from the cathode, anode and emitting layer, the electronic device may comprise further layers. These are selected, for example, from in each case one or more hole injection layers, hole transport layers, hole blocker layers, electron transport layers, Foreignfiling text P24-238-SEC-WO01 20251111

[0347] - 45 - electron injection layers, electron blocker layers, exciton blocker layers, interlayers, charge generation layers and / or organic or inorganic p / n junctions. However, it should be pointed out that not every one of these layers need necessarily be present and the choice of layers always depends on the compounds used and especially also on whether the

[0348] 5 device is a fluorescent or phosphorescent electroluminescent device.

[0349] The sequence of layers in the electronic device is preferably as follows: -anode- -hole injection layer- -hole transport layer- -optionally further hole transport layers- -emitting layer- -optionally hole blocker layer- -electron transport layer-

[0350] 15 -electron injection layer- -cathode-.

[0351] At the same time, it should be pointed out again that not all the layers mentioned need be present and / or that further layers may additionally be present.

[0352] 20 The organic electroluminescent device of the invention may contain two or more emitting layers. More preferably, these emission layers have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce and which emit blue, green, yellow, orange or red light are used in the emitting layers. Especially preferred are

[0353] 25 three-layer systems, i.e. systems having three emitting layers, wherein one of the three layers in each case shows blue emission, one of the three layers in each case shows green emission, and one of the three layers in each case shows orange or red emission. The compounds of the invention here are preferably present in a hole-transporting layer or in the emitting layer. It should be noted that, for the production of white light, rather than a plurality of colour-emitting emitter compounds, an emitter compound used individually which emits over a broad wavelength range may also be suitable.

[0354] It is preferable that the compound represented by Formula (1) is used as hole transport material. The emitting layer here may be a fluorescent emitting layer, or it may be a

[0355] 35 phosphorescent emitting layer. The emitting layer is preferably a blue-fluorescing layer or a green-phosphorescing layer. Foreignfiling text P24-238-SEC-WO01 20251111

[0356] - 46 -

[0357] When the device containing the compound represented by Formula (1) contains a phosphorescent emitting layer, it is preferable that this layer contains two or more, preferably exactly two, different matrix materials (mixed matrix system). Preferred embodiments of mixed matrix systems are described in detail further down.

[0358] 5

[0359] If the compound represented by Formula (1) is used as hole transport material in a hole transport layer, a hole injection layer or an electron blocker layer, the compound can be used as pure material, i.e. in a proportion of 100%, in the hole transport layer, or it can be used in combination with one or more further compounds.

[0360] In a preferred embodiment, a hole-transporting layer comprising the compound represented by Formula (1) additionally comprises one or more further hole-transporting compounds. These further hole-transporting compounds are preferably selected from triarylamine compounds, more preferably from monotriarylamine compounds. They are

[0361] 15 most preferably selected from the preferred embodiments of hole transport materials that are specified further down. In the preferred embodiment described, the compound represented by Formula (1) and the one or more further hole-transporting compounds are preferably each present in a proportion of at least 10%, more preferably each in a proportion of at least 20%.

[0362] 20

[0363] In a preferred embodiment, a hole-transporting layer comprising the compound represented by Formula (1) additionally contains one or more p-dopants. P-dopants used according to the present invention are preferably those organic electron acceptor compounds capable of oxidizing one or more of the other compounds in the mixture.

[0364] 25

[0365] Particularly preferred as p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides comprising at least one transition metal or a metal from main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as binding site. Preference is further given to transition metal oxides as dopants, preferably oxides of rhenium, molybdenum and tungsten, more preferably Re2O?, MoOa, WO3 and ReCh. Still further preference is given to complexes of bismuth in the (III) oxidation state, more particularly bismuth(lll) complexes with electron-deficient ligands, more particularly

[0366] 35 carboxylate ligands. Foreignfiling text P24-238-SEC-WO01 20251111

[0367] - 47 -

[0368] The p-dopants are preferably in substantially homogeneous distribution in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix. The p-dopant is preferably present in a proportion of 1% to 10% in the p-doped layer.

[0369] 5

[0370] Preferred p-dopants are furthermore the compounds which are explicitly disclosed in the table on p. 86-87 of WO2021 / 156323A1.

[0371] In a preferred embodiment, a hole injection layer that conforms to one of the following embodiments is present in the device: a) it contains a triarylamine and a p-dopant; or b) it contains a single electron-deficient material (electron acceptor). In a preferred embodiment of embodiment a), the triarylamine is a monotriarylamine, especially one of the preferred triarylamine derivatives mentioned further down. In a preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylene derivative as

[0372] 15 described in US 2007 / 0092755.

[0373] The compound represented by Formula (1) may be present in a hole injection layer, in a hole transport layer and / or in an electron blocker layer of the device. When the compound is present in a hole injection layer or in a hole transport layer, it has preferably been p-

[0374] 20 doped, meaning that it is in mixed form with a p-dopant, as described above, in the layer.

[0375] The compound represented by Formula (1) is preferably present in an electron blocker layer. In this case, it is preferably not p-doped. Further preferably, in this case, it is preferably in the form of a single compound in the layer without addition of a further

[0376] 25 compound.

[0377] In an alternative preferred embodiment, the compound represented by Formula (1) is used in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent emitting compounds. The phosphorescent emitting compounds here are preferably selected from red-phosphorescing and greenphosphorescing compounds.

[0378] The proportion of the matrix material in the emitting layer in this case is between 50.0% and 99.9% by volume, preferably between 80.0% and 99.5% by volume, and more

[0379] 35 preferably between 85.0% and 97.0% by volume. Foreignfiling text P24-238-SEC-WO01 20251111

[0380] - 48 -

[0381] Correspondingly, the proportion of the emitting compound is between 0.1% and 50.0% by volume, preferably between 0.5% and 20.0% by volume, and more preferably between 3.0% and 15.0% by volume.

[0382] 5 An emitting layer of an organic electroluminescent device may also contain systems comprising a plurality of matrix materials (mixed matrix systems) and / or a plurality of emitting compounds. In this case too, the emitting compounds are generally those compounds having the smaller proportion in the system and the matrix materials are those compounds having the greater proportion in the system. In individual cases, however, the proportion of a single matrix material in the system may be less than the proportion of a single emitting compound.

[0383] It is preferable that the compounds represented by Formula (1) are used as a component of mixed matrix systems, preferably for phosphorescent emitters. The mixed matrix

[0384] 15 systems preferably comprise two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material having hole-transporting properties and the other material is a material having electrontransporting properties. It is further preferable when one of the materials is selected from compounds having a large energy differential between HOMO and LIIMO (wide-bandgap

[0385] 20 materials). The compound represented by Formula (1) in a mixed matrix system is preferably the matrix material having hole-transporting properties. Correspondingly, when the compound represented by Formula (1) is used as matrix material for a phosphorescent emitter in the emitting layer of an OLED, a second matrix compound having electron-transporting properties is present in the emitting layer. The two different

[0386] 25 matrix materials may be present here in a ratio of 1 :50 to 1:1 , preferably 1:20 to 1:1, more preferably 1 : 10 to 1 : 1 and most preferably 1 :4 to 1 : 1.

[0387] The desired electron-transporting and hole-transporting properties of the mixed matrix components may, however, also be combined mainly or entirely in a single mixed matrix component, in which case the further mixed matrix component(s) fulfil(s) other functions.

[0388] Preference is given to using the following material classes in the abovementioned layers of the device:

[0389] 35 Phosphorescent emitters: Foreignfiling text P24-238-SEC-WO01 20251111

[0390] - 49 -

[0391] The term "phosphorescent emitters" typically encompasses compounds where the emission of light is effected through a spin-forbidden transition, for example a transition from an excited triplet state or a state having a higher spin quantum number, for example a quintet state.

[0392] 5

[0393] Suitable phosphorescent emitters are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38, and less than 84, more preferably greater than 56 and less than 80. Preference is given to using, as phosphorescent emitters, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

[0394] In the context of the present invention, all luminescent iridium, platinum or copper

[0395] 15 complexes are considered to be phosphorescent compounds.

[0396] In general, all phosphorescent complexes as used for phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices of the invention. Further

[0397] 20 examples of suitable phosphorescent emitters are those shown in the table on p.100-104 of WO2023 / 025971A2.

[0398] Fluorescent emitters:

[0399] 25 Preferred fluorescent emitting compounds are selected from the class of the arylamines. An arylamine or an aromatic amine in the context of this invention is understood to mean a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines or aromatic chrysenediamines. An aromatic anthraceneamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9 position. An aromatic anthracenediamine is

[0400] 35 understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10 position. Aromatic pyreneamines, pyrenediamines, chryseneamines and chrysenediamines are defined analogously, where Foreignfiling text P24-238-SEC-WO01 20251111

[0401] - 50 - the diarylamino groups are bonded to the pyrene preferably in the 1 position or 1,6 position. Further preferred emitting compounds are indenofluoreneamines or -diamines, benzoindenofluoreneamines or -diamines, and dibenzoindenofluoreneamines or - diamines, and indenofluorene derivatives having fused aryl groups. Likewise preferred are

[0402] 5 pyrenearylamines. Likewise preferred are benzoindenofluoreneamines, benzofluoreneamines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives joined to furan units or to thiophene units.

[0403] Matrix materials for fluorescent emitters:

[0404] Preferred matrix materials for fluorescent emitters are selected from the classes of the oligoarylenes (e.g. 2,2’,7,7’-tetraphenylspirobifluorene), especially the oligoarylenes containing fused aromatic groups, the oligoarylenevinylenes, the polypodal metal complexes, the hole-conducting compounds, the electron-conducting compounds,

[0405] 15 especially ketones, phosphine oxides and sulfoxides; the atropisomers, the boronic acid derivatives or the benzanthracenes. Particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Very

[0406] 20 particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising anthracene, benzanthracene, benzophenanthrene and / or pyrene or atropisomers of these compounds. An oligoarylene in the context of this invention shall be understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.

[0407] 25

[0408] Matrix materials for phosphorescent emitters:

[0409] Preferred matrix materials for phosphorescent emitters are, as well as the compounds represented by Formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, e.g. CBP (N,N- biscarbazolylbiphenyl) or carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives,

[0410] 35 triphenylene derivatives, or lactams.

[0411] Electron-transporting materials: Foreignfiling text P24-238-SEC-WO01 20251111

[0412] - 51 -

[0413] Suitable electron-transporting materials are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials used in these layers according to the prior art.

[0414] 5

[0415] Materials used for the electron transport layer may be any materials that are used as electron transport materials in the electron transport layer according to the prior art. Especially suitable are aluminium complexes, for example Alqs, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.

[0416] Preferred electron transport and electron injection materials are those shown in the table

[0417] 15 on p. 73-75 of W02020 / 109434A1.

[0418] Hole-transporting materials:

[0419] Further compounds which, in addition to the compounds of the formula (1), are preferably

[0420] 20 used in hole-transporting layers of the OLEDs of the invention are indenofluoreneamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with fused aromatic systems, monobenzoindenofluoreneamines, dibenzoindenofluoreneamines, spirobifluoreneamines, fluoreneamines, spirodibenzopyranamines, dihydroacridine derivatives, spirodibenzofurans and

[0421] 25 spirodibenzothiophenes, phenanthrenediarylamines, spirotribenzotropolones, spirobifluorenes having meta-phenyldiamine groups, spirobisacridines, xanthenediarylamines, and 9,10-dihydroanthracene spiro compounds having diarylamino groups. Preferred hole-transporting compounds are those shown the table on p. 76-80 of W02020 / 109434A1.

[0422] Preferred cathodes of the electronic device are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth

[0423] 35 metal and silver, for example an alloy composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, it is also possible to use further metals having a relatively high work function, for example Ag or Al, in which case Foreignfiling text P24-238-SEC-WO01 20251111

[0424] - 52 - combinations of the metals such as Ca / Ag, Mg / Ag or Ba / Ag, for example, are generally used. It may also be preferable to introduce a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but

[0425] 5 also the corresponding oxides or carbonates (e.g. LiF, U2O, BaF2, MgO, NaF, CsF, CS2CO3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm.

[0426] Preferred anodes are materials having a high work function. Preferably, the anode has a work function of greater than 4.5 eV versus vacuum. Firstly, metals having a high redox potential are suitable for this purpose, for example Ag, Pt or Au. Secondly, metal / metal oxide electrodes (e.g. Al / N i / N iOx, AI / PtOx) may also be preferred. For some applications, at least one of the electrodes has to be transparent or partly transparent in order to enable either the irradiation of the organic material (organic solar cell) or the emission of light

[0427] 15 (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is further given to conductive doped organic materials, especially conductive doped polymers. In addition, the anode may also consist of two or more layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten

[0428] 20 oxide, molybdenum oxide or vanadium oxide.

[0429] In a preferred embodiment, the electronic device is characterized in that one or more layers are coated by a sublimation process. In this case, the materials are applied by vapour deposition in vacuum sublimation systems at an initial pressure of less than

[0430] 25 10'5mbar, preferably less than 10'6mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10'7mbar.

[0431] Preference is likewise given to an electronic device, characterized in that one or more layers are coated by the OVPD (organic vapour phase deposition) method or with the aid of a carrier gas sublimation. In this case, the materials are applied at a pressure between 10'5mbar and 1 bar. A special case of this method is the OVJP (organic vapour jet printing) method, in which the materials are applied directly by a nozzle and thus structured (for example M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0432] 35 Preference is additionally given to an electronic device, characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but Foreignfiling text P24-238-SEC-WO01 20251111

[0433] - 53 - more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds of formula (1) are needed. High solubility can be achieved by suitable substitution of the compounds.

[0434] 5 It is further preferable that an electronic device of the invention is produced by applying one or more layers from solution and one or more layers by a sublimation method.

[0435] After application of the layers, according to the use, the device is structured, contact- connected and finally sealed, in order to rule out damaging effects of water and air.

[0436] According to the invention, the electronic devices comprising one or more compounds of formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications.

[0437] 15 Examples

[0438] A) Synthesis examples a) Synthesis example of intermediate Int-L-a

[0439] 25 CAS 2299231-59-5 CAS1969331 -20-1

[0440] 16.1 g (34.8 mmol) of the pinacolboronic ester derivative (CAS No.: 1969331-20-1) and 12.05 g (45 mmol) of CAS 2299231-59-5 are suspended in 450 ml of dioxane and 10.6 g of caesium fluoride (69.9 mmol). 1.02 g (1.39 mmol) of bis(tricyclohexylphosphine)palladium dichloride are added to this suspension, and the reaction mixture is heated under reflux for 18 h. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 80 ml of water and then concentrated to dryness. After the crude product has been filtered through silica gel with toluene, the remaining residue is recrystallized from heptane / toluene. Yield is 13.6 g (24.0 mmol, 69%).

[0441] 35 Following compounds can be obtained in analogous manner and similar yields:

[0442] | Intermediate | Boronic ester | Chloride product Foreignfiling text P24-238-SEC-WO01 20251111

[0443] 5

[0444] 15

[0445] 20

[0446] 25 b) Synthesis of Amine Intermediate N-lnt-1

[0447] 1459147-21-7 (17.3 g, 40.50 mmol) is added in a round bottom flask and dissolved in toluene (300 mL), and [1 ,1'-biphenyl]-2-amine (6.85 g, 40.5 mmol), Pd2(dba)s (1.85 g;1.02 mmol), P(tBu)a (50 wt % Sol.) (1.64 mL, 4.05 mmol), sodium-tert-butoxide (11.67 g, 121

[0448] 35 mmol) are added and stirred at 80°C. After full conversion, the reaction mixture is extracted with DCM and water. The combined organic layers are dried over MgSC>4 and concentrated. The resulting compound is purified by column chromatography (SiC>2) and recrystallization. Foreignfiling text P24-238-SEC-WO01 20251111

[0449] - 55 -

[0450] Yield: 16.8 g (32.6 mmol; 81%)

[0451] Following compound can be synthesized in analogous manner:

[0452] 5

[0453] 15

[0454] 20

[0455] 25 Foreignfiling text P24-238-SEC-WO01 20251111

[0456] - 56 -

[0457] 19.2 g (55.6 mmol) SM1 and 30.0 g (55.6 mmol) SM2 and 8.0 g (83.4 mmol) sodium tert- butoxylate are dissolved in 900 ml toluene. 1.41 g (1.7 mmol) XPhos Pd G3 are added and the reaction mixture is stirred for 3 hours under reflux until complete conversion. The reaction mixture is allowed to cool to room temperature and 500 ml water are added. The

[0458] 5 combined phases are extracted with toluene, dried over sodium thiosulfate, and concentrated under reduced pressure.

[0459] The residue is purified by filtration over AI2O3 (toluene) and crystallization out of toluene / heptane until a HPLC purity of >99.9% and finally by sublimation at 310 °C at 10'6bar. Yield: 25.7 g (30.3 mmol, 55%)

[0460] Following compounds can be obtained in analogous manner and similar yields:

[0461] 15

[0462] 20

[0463] 25

[0464] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0465] - 57 -

[0466] 5

[0467] 15

[0468] 20

[0469] 25

[0470] 35 Foreignfiling_text_P24-238-SEC-WO01_20251111

[0471] - 58 - Foreignfiling text P24-238-SEC-WO01 20251111

[0472] 5

[0473] 15

[0474] 20

[0475] 25

[0476] Synthesis of compound 1-D 35

[0477] Compound 1 Compound-1 -D Foreignfiling text P24-238-SEC-WO01 20251111

[0478] - 60 -

[0479] 18.8 g of compound 1 (22.2 nmmol; 1,00 eq) is suspended in 190 mL (80 eq) toluene-d8 and cooled down to 0°C. 20 mL (10.00 eq.) trifluoromethanesulfonic acid are added and the mixture is stirred at room temperature. After 6 hours 40 mL (130 eq) of D2O are added slowly at 0°C. after one hour the mixture is neutralized with and aqueous solution of

[0480] 5 NaOH (38 mL; 20%) and 150 ml heptane are added to the mixture, and the precipitated solid is filtered off and washed with ethanol. To remove the remaining solvents the compound-1 D and the mixture of H / D-isotopomers and H / D-isotopologues are sublimed (p = 5 x IO’7mbar). Yield (12.0 g, 13.6 mmol, 61 %), Purity 99,9%.

[0481] B) Device examples

[0482] 1) General production process for the OLEDs and characterization of the OLEDs

[0483] Glass plaques which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm are the substrates to which the OLEDs are applied.

[0484] 15

[0485] The OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocker layer (EBL) / emission layer (EML) / electron transport layer, optionally with second layer (ETL) / electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm.

[0486] 20 The exact structure of the OLEDs can be found in the tables which follow. The materials used for production of the OLEDs are shown in a table below.

[0487] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer consists of at least one matrix material (host material) and an emitting

[0488] 25 dopant which is added to the matrix material(s) in a particular proportion by volume by coevaporation. Details given in such a form as TMM-1 (32%):TMM-2 (60%):TEG(8%) mean here that the material TMM-1 is present in the layer in a proportion by volume of 32%, TMM-2 is present in the layer in a proportion by volume of 60% and TEG in a proportion of 8%.

[0489] In an analogous manner, the electron transport layer and the hole injection layer also consist of a mixture of two materials. The structures of the materials that are used in the OLEDs are shown in Table 2.

[0490] The OLEDs are characterized in a standard manner. For this purpose, the

[0491] 35 electroluminescence spectra, the external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation characteristics, and the lifetime are determined. The Foreignfiling text P24-238-SEC-WO01 20251111

[0492] - 61 - parameter EQE @ 10 mA / cm2refers to the external quantum efficiency which is attained at 10 mA / cm2. The parameter II @ 10 mA / cm2refers to the operating voltage at 10 mA / cm2. The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion in the course of operation with constant

[0493] 5 current density. An LT90 figure means here that the lifetime reported corresponds to the time after which the luminance has dropped to 90% of its starting value. The figure @80 mA / cm2means here that the lifetime in question is measured at 80 mA / cm2.

[0494] 15

[0495] 20

[0496] 25

[0497] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0498] -62-

[0499] 5

[0500] 15

[0501] 20

[0502] 25

[0503] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0504] - 63 -

[0505] 5

[0506] 15

[0507] 20

[0508] 25

[0509] 2) Inventive OLEDs containing a compound of the formula (1) in the EBL of greenphosphorescing OLEDs

[0510] Devices as shown in the following table are produced:

[0511] Table 2: Structure of the OLEDs

[0512] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0513] - 64 -

[0514] 5

[0515] 15

[0516] 20

[0517] 25

[0518] In the device setup shown above, the examples E1-E11 show good voltage for the OLED and better efficiency compared to the comparison example CE1, while lifetime is overall improved.

[0519] 35 Foreignfiling text P24-238-SEC-WO01 20251111

[0520] -65-

[0521] 5

[0522] 15

[0523] 20

[0524] 25

[0525] 35

Claims

Foreignfiling text P24-238-SEC-WO01 20251111- 66 -Patent Claims1. Compound represented by a formula (1):Formula (1) where the groups and indices that occur are as follows:20X is O, S or a single bond;Y is O, S or a single bond; wherein X and Y are not both single bonds;25R1stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(R4)2, C(=O)R4, P(=O)(R4)2, S(=O)R4, S(=O)2R4, NO2, Si(R4)3, B(OR4)2, OSO2R4, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2groups may be replaced by R4C=CR4, C=C, Si(R4)2, Ge(R4)2, Sn(R4)2, C=O, C=S, C=Se, P(=O)(R4), SO, SO2, O, S or CONR4and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more35 radicals R4, or an aryloxy group having 5 to 60 ring atoms, which may be substituted by one or more radicals R4, wherein two of radicals R1may form a mono- or polycyclic,Foreignfiling text P24-238-SEC-WO01 20251111- 67 - aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R4;R2and R3stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I,5 CHO, CN, N(R5)2, C(=O)R5, P(=O)(R5)2, S(=O)R5, S(=O)2R5, NO2, Si(R5)3, B(OR5)2, OSO2R5, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R5, where in each case one or more non- adjacent CH2groups may be replaced by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, P(=O)(R5), SO, SO2, O, S or CONR5and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R5, or an aryloxy group having 5 to 60 ring atoms, which may be substituted by one or more radicals R5, wherein two of radicals R2or R3may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be15 substituted by one or more radicals R5;Ar1stands for an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case also be substituted by one or more radicals R6;20 L1and L2stand on each occurrence, identically or differently, for a single bond, an aromatic having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R7; n1 and n2 stand on each occurrence, identically or differently, for an integer selected25 from 0 to 3;R4, R5, R6and R7stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R', where in each case one or more non- adjacent CH2groups may be replaced by R'C=CR', C=C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S or CONR' and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or35 more radicals R', or an aryloxy group having 5 to 60 ring atoms, which may be substituted by one or more radicals R', where two of radicals R4, R5, R6and R7mayForeignfiling text P24-238-SEC-WO01 20251111- 68 - form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R';Ar stands on each occurrence, identically or differently, for an aromatic or heteroaromatic5 ring system having 5 to 40 ring atoms, which may in each case also be substituted by one or more radicals R';R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

2. Compound according to Claim 1 , wherein the compound satisfies one of conditions A to C15 <Condition A>X is O or S; and Y is a single bond<Condition B>X is a single bond; and Y is O or S<Condition C>20 X is O or S; and Y is O or S.

3. Compound according to Claim 1 or 2, wherein the compound represented by at least one of Formulae 1-1 to 1-4:25Foreignfiling text P24-238-SEC-WO01 20251111- 69 -5wherein X is O or S, Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given in Claim 1.

154. Compound according to one or more of claims 1 to 3, wherein the compound represented by at least one of Formulae 1-A-1 to 1-A-4:2025Foreignfiling text P24-238-SEC-WO01 202511115wherein X is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given inClaim 1.

155. Compound according to one or more of claims 1 to 3, wherein the compound represented by at least one of Formulae 1-B-1 to 1-B-4:2025Foreignfiling text P24-238-SEC-WO01 20251111- 71 -5wherein Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given inClaim 1.

156. Compound according to one or more of claims 1 to 3, wherein the compound represented by at least one of Formulae 1-C-1 to 1-C-4:2025Foreignfiling text P24-238-SEC-WO01 20251111- 72 -5wherein X is O or S, Y is O or S and R1, R2, R3, Ar1, L1, L2, n1 and n2 have the definition given in Claim 1.

157. Compound according to one or more of claims 1 to 6, wherein R1stands on each occurrence, identically or differently, for a straight-chain alkyl group having 1 to 40 C atoms or branched alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, or an aromatic or heteroaromatic ring20 system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R4, wherein two of radicals R1may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R4; wherein R4has the definition given in Claim 1.25 8. Compound according to one or more of claims 1 to 7, wherein R2and R3stand on each occurrence, identically or differently, for H, D, a straight-chain alkyl group having 1 to 40 C atoms or branched alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R5, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R5, wherein two of radicals R2or R3may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R5; wherein R5has the definition given in Claim 1.35 9. Compound according to one or more of claims 1 to 8, wherein L1and L2stand on each occurrence, identically or differently, for a single bond or divalent groups derived from benzene, which may be substituted by one or more radicals R7;Foreignfiling text P24-238-SEC-WO01 20251111- 73 - wherein R7has the definition given in Claim 1.

10. Compound according to one or more of claims 1 to 9, wherein that compound comprises at least one of deuterium.

511. A process for producing a compound according to formula (1) according to one or more of claims 1 to 10, wherein that a fluorenyl compound which carries at least one reactive group is either a) reacted in a Buchwald reaction with a secondary amine , or b) is reacted in a Suzuki reaction with a boronic acid-substituted tertiary amine, or c) in a sequence of first i) Suzuki reaction with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound, and then ii) Buchwald reaction of the resulting intermediate with a secondary amine is reacted to give a compound according to formula (1) according to one or more of claims 1 to 10.15 12. Formulation containing at least one compound according to one or more of claims 1 to 10, and at least one solvent.

13. Electronic device containing at least one compound according to one or more of claims 1 to 10.2014. Electronic device according to claim 13, characterized in that it is an organic electroluminescent device and contains anode, cathode and at least one emitting layer, and that the compound is contained in a hole-transporting layer or in an emitting layer of the device.2515. Use of a compound according to one or more of claims 1 to 10 in an electronic device.35

Images