Materials for electronic devices

Abstract

The present application concerns OLED materials, synthesis processes for making these materials, and the use of these materials in OLEDs.

Description

[0001] Foreignfiling text P24-253-SEC-WO01 20251217

[0002] - 1 -

[0003] Materials for electronic devices

[0004] The present application relates to certain heteroaromatic amine compounds, which contain a xanthene or thioxanthene moiety. The compounds are suitable for use in

[0005] 5 electronic devices.

[0006] 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 application of electrical voltage. The construction and general principle of function of OLEDs are known to those skilled in the art.

[0007] In electronic devices, especially OLEDs, there is great interest in an improvement

[0008] 15 in the performance data. In these aspects, it has not yet been possible to find any entirely satisfactory solution.

[0009] 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

[0010] 20 compounds and compounds that can serve as hole-transporting matrix material, especially for phosphorescent emitters, in an emitting layer. For this purpose, especially compounds that have a high glass transition temperature, high stability, and high conductivity for holes are being sought for. 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, a low capacitance / voltage signal is often desired, in particular being of great importance

[0011] 30 for the general charging behaviour of an OLED. Foreignfiling text P24-253-SEC-WO01 20251217

[0012] - 2 -

[0013] In the prior art, triarylamine compounds in particular, for example spirobifluoreneamines and fluoreneamines, are known as hole transport materials and hole-transporting matrix materials for electronic devices. Still, there remains room for improvement in respect of the above-mentioned properties. In addition, there is a need for new compounds, which are useful for the above field of

[0014] 5 application.

[0015] It has now been found that heteroaromatic amines of the formula below which are characterized in that they comprise a xanthene or thioxanthene moiety, and a 4- fluorenyl, 1 -dibenzofuranyl or 1 -dibenzothiophenyl moiety, 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 efficiency and low operating voltage of the devices, while having improved capacitance and charging

[0016] 15 behaviour. Further preferably, the compounds found have a high glass transition temperature, high stability, low sublimation temperature, good solubility, good synthetic accessibility and high conductivity for holes.

[0017] The particular combination of the xanthene or thioxanthene moiety, and the 4- fluorenyl, 1 -dibenzofuranyl or 1 -dibenzothiophenyl moiety, bonded to the amine

[0018] 20 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 blocking layers, which is in contact with the emitting layer.

[0019] In particular, OLEDs comprising the compounds show an improved capacitance, particularly when the compounds are used in an electron blocking layer, more particularly when they are 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

[0020] 30 compound according to the invention, and the other comprises a compound with a chemical structure which is not according to the invention. Further, OLEDs Foreignfiling text P24-253-SEC-WO01 20251217

[0021] - 3 - comprising the compounds show only a small voltage increase over their lifetime, particularly when the compounds are 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

[0022] 5 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 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. bject of the present application is therefore a compound according to the formula formula (I), where the following applies to the variable groups:

[0023] 30

[0024] X1is selected, identically or differently, from O and S;

[0025] X2is selected from O, S, C(R°)2 and Si(R°)2; Foreignfiling text I k253-SEC-WO01 20251217

[0026] - 4 -

[0027] L1is selected from single bond, aromatic ring systems having 6 to 40 aromatic ring atoms which are substituted with radicals R7, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted with radicals R7;

[0028] Ar1is selected from aromatic ring systems having 6 to 40 aromatic ring atoms

[0029] 5 which are substituted with radicals R8, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted with radicals R8;

[0030] R° is selected, identically or differently, from H, D, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two radicals R° may be connected to each other to form a ring; and where the said straight-chain alkyl groups, the said branched or cyclic alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9;

[0031] 15 R1is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R1may

[0032] 20 be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0033] R2is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R2may

[0034] 30 be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring Foreignfiling text I k253-SEC-WO01 20251217

[0035] - 5 - systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0036] R3is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C

[0037] 5 atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R3may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0038] R4is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)a, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R4may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0039] R5is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)s, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R5may be connected to each other to form a ring; where the said alkyl, alkoxy,

[0040] 30 alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 Foreignfiling text I k253-SEC-WO01 20251217

[0041] - 6 - groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0042] R6is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms,

[0043] 5 alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R6may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0044] R7is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)a, straight-chain alkyl or alkoxy groups having 1 to 20 C

[0045] 15 atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R7may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring

[0046] 20 systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0047] R8is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)s, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R8may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring

[0048] 30 systems are substituted by radicals R9, and where one or more CH2 Foreignfiling text I k253-SEC-WO01 20251217

[0049] - 7 - groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;

[0050] R9is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R10)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms,

[0051] 5 alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R9may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R10, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R10C=CR10-, -C=C-, Si(R10)2, NR10, -O-, or -S-;

[0052] R10is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms,

[0053] 15 branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where the above-mentioned straight-chain alkyl or alkoxy groups, the above-mentioned branched or cyclic alkyl or alkoxy groups, the above-mentioned alkenyl or alkynyl groups, the above-

[0054] 20 mentioned aromatic ring systems having 6 to 40 aromatic ring atoms, and the above-mentioned heteroaromatic ring systems having 5 to 40 aromatic ring atoms may each be substituted by one or more selected from D, F, Cl, Br, I, and CN, and alkyl groups having 1 to 20 C atoms which are substituted by one or more selected from D, F, Cl, Br, I, and CN; where the group L1is bonded in one of the positions marked with 1, 2, 3, 4.

[0055] The following definitions apply to the chemical groups used as general definitions. They apply insofar as no more specific definitions are given.

[0056] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0057] - 8 -

[0058] An aryl group here is taken to mean either a single aromatic ring, for example benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene, or anthracene. A condensed aromatic polycycle in the sense of the present application consists of two or more single aromatic rings which are condensed with one another, where “condensed with one another” means that each

[0059] 5 aromatic ring of the aromatic polycycle is condensed with at least one other aromatic ring of the aromatic polycycle. An aryl group in the sense of this invention contains 6 to 40 aromatic ring atoms. An aryl group does not contain any heteroatoms as aromatic ring atoms, but only carbon atoms.

[0060] A heteroaryl group here is taken to mean either a single heteroaromatic ring, such as pyridine, pyrimidine or thiophene, or a condensed heteroaromatic polycycle, such as quinoline or carbazole. A condensed heteroaromatic polycycle in the sense of the present application consists of two or more single aromatic or heteroaromatic rings, which are condensed with one another, where at least one of the two or more

[0061] 15 single aromatic or heteroaromatic rings is a heteroaromatic ring. “Condensed with one another” here has the analogous meaning as mentioned above for the case of condensed aromatic polycycles. A heteroaryl group in the sense of this invention contains 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and S.

[0062] 20 An aryl or heteroaryl group, which may in each case be substituted by the above- mentioned radicals, is taken to mean, in particular, a group derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, 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, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, benzimidazolo[1,2-a]benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalini- midazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole,

[0063] 30 isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, aza- Foreignfiling text P24-253-SEC-WO01 20251217

[0064] - 9 - carbazole, 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-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.

[0065] 5

[0066] An aromatic ring system in the sense of this invention is a system which does not necessarily contain only aryl groups, but which may additionally contain one or more non-aromatic rings, which are condensed with at least one aryl group. Such non-aromatic rings contain exclusively carbon atoms as ring atoms. Examples of groups embraced by such definition are tetrahydronaphthalene, fluorene, and spirobifluorene. Furthermore, the term aromatic ring system is understood to embrace systems consisting of two or more aromatic ring systems which are connected to each other via single bonds, such as biphenyl, terphenyl, 7-phenyl-2- fluorenyl and quaterphenyl. An aromatic ring system in the sense of this invention

[0067] 15 contains 6 to 40 C atoms as the aromatic ring atoms and no heteroatoms as ring atoms of the ring system. The atoms of any non-aromatic rings which are condensed to the aromatic rings, do not count into the number of aromatic ring atoms according to the definition of the present application. An aromatic ring system in the sense of this application does not comprise any heteroaryl groups, as defined above.

[0068] 20

[0069] A heteroaromatic ring system is defined in analogy to the aromatic ring system above, but with the difference that it must contain at least one heteroatom as one of the ring atoms. As it is the case for the aromatic ring system, it does not necessarily contain only aryl and heteroaryl groups, but it may additionally contain one or more non-aromatic rings, which are condensed with at least one aryl or heteroaryl group. The non-aromatic rings may contain only carbon atoms as ring atoms, or they may contain additionally one or more heteroatoms, where the heteroatoms are preferably selected from N, O and S. An example for such a heteroaromatic ring system is benzpyranyl. Furthermore, the term heteroaromatic ring system is understood to embrace systems consisting of two or more aromatic or

[0070] 30 heteroaromatic ring systems, which are connected to each other via single bonds, such as 4,6-diphenyl-2-triazi nyl. A heteroaromatic ring system in the sense of this Foreignfiling text P24-253-SEC-WO01 20251217

[0071] - 10 - invention contains 5 to 40 aromatic ring atoms, which are selected from carbon and heteroatoms, where at least one of the aromatic ring atoms is a heteroatom. The heteroatoms are preferably selected from N, O or S. The atoms of any non-aromatic rings which may be condensed to the aromatic or heteroaromatic rings according to a possible embodiment as defined above, do not count into the number of aromatic

[0072] 5 ring atoms according to the definition of the present application.

[0073] The terms “heteroaromatic ring system” and “aromatic ring system” according to the definition of the present application differ from each other by the fact that the aromatic ring system cannot comprise any heteroatom as ring atom, whereas the heteroaromatic ring system must comprise at least one heteroatom as ring atom. Such heteroatom may be present as a ring atom of a non-aromatic heterocyclic ring of the system, or as a ring atom of an aromatic heterocyclic ring of the system.

[0074] According to the above, any aryl group, as defined above, is embraced by the term

[0075] 15 “aromatic ring system”, as defined above, and any heteroaryl group, as defined above, is embraced by the term “heteroaromatic ring system”, as defined above.

[0076] An aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms is in particular a group which is derived from the above-mentioned aryl or heteroaryl groups, or from biphenyl, terphenyl,

[0077] 20 quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, and indenocarbazole, or from any combinations of these groups.

[0078] For the purposes of the present invention, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, in which, in addition, individual H atoms or CH2 groups may be substituted by the groups mentioned above under the definition of the radicals, is preferably taken to mean the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl,

[0079] 30 cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, hep- Foreignfiling text P24-253-SEC-WO01 20251217

[0080] - 11 - tenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl.

[0081] An alkoxy or thioalkyl group having 1 to 20 C atoms is preferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy,

[0082] 5 s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butyl- thio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexyl- thio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.

[0083] 15

[0084] The phrase “two or more radicals may be connected to each other to form a ring” shall be understood to include the case that the two radicals are connected by a chemical bond. Additionally, the phrase shall be understood to include the case that one of the two radicals is H, this radical H is removed, and the other of the two radicals forms a ring by being connected to the position, to which this radical H was

[0085] 20 initially bonded.

[0086] According to a preferred embodiment, both groups X1are O.

[0087] According to a preferred embodiment, X2is O or C(R°)2. According to a more preferred embodiment, X2is O.

[0088] According to a preferred embodiment, L1is selected from single bond and aromatic ring systems having 6 to 30 aromatic ring atoms, which are substituted with radicals R7, more preferably from single bond and aromatic ring systems having 6 to 12 aromatic ring atoms, which are substituted with radicals R7. Most preferably L1is a

[0089] 30 single bond. Foreignfiling text P24-253-SEC-WO01 20251217

[0090] - 12 -

[0091] Preferred embodiments of L1, other than single bond, are the groups shown in the following table:

[0092] 5

[0093] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0094] - 13 -

[0095] 5

[0096] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0097] 5

[0098] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0099] - 15 -

[0100] 5

[0101] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0102] - 16- 5

[0103] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0104] - 17 -

[0105] The groups in the above list may be substituted with radicals R7other than H or D in the positions depicted as free positions. Preferably, they have no substituents other than H or D in these positions, most preferably, they have only H in these positions.

[0106] Among the above groups L1, particularly preferred are groups L1-23 to L1-81 , L1-98,

[0107] 5 L1-99, L1-101 and L1-103. Most preferred is L1-23.

[0108] Ar1is preferably selected from aromatic ring systems having 6 to 24 aromatic ring atoms which are substituted with radicals R8, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms, which are substituted with radicals R8; more preferably from aryl groups having 6 to 12 aromatic ring atoms, which are substituted with radicals R8, and heteroaryl groups having 5 to 18 aromatic ring atoms, which are substituted with radicals R8.

[0109] In a particularly preferred embodiment, Ar1is selected from phenyl, ortho-biphenyl,

[0110] 15 meta-biphenyl, para-biphenyl, 1-naphthyl, 2-naphthyl, 1-phenanthrenyl, 2- phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 1-fluorenyl, 2-fluorenyl, 3- fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1-position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4- position, 1 -dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzofuranyl, 2- dibenzothiophenyl, 3-dibenzofuranyl, 3-dibenzothiophenyl, 4-dibenzofuranyl, 4-

[0111] 20 dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1-position, benzo- dibenzothiophenyl bonded in 1-position, benzo-dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3- position, benzo-dibenzothiophenyl bonded in 3-position, benzo-dibenzofuranyl bonded in 4-position, benzo-dibenzothiophenyl bonded in 4-position, spiroxanthene, spirobixanthene, and phenyl, which is substituted in para, meta or ortho position, preferably in para-position, with a group selected from 1-naphthyl, 2-naphthyl, 1- fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1-position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1 -dibenzofuranyl, 1-dibenzothiophenyl, 2- dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3-dibenzothiophenyl, 4-

[0112] 30 dibenzofuranyl, 4-dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1-position, benzo-dibenzothiophenyl bonded in 1-position, benzo-dibenzofuranyl bonded in 2- Foreignfiling text_P24-253-SEC-W001_20251217

[0113] - 18 - position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo-dibenzothiophenyl bonded in 3-position, benzo- dibenzofuranyl bonded in 4-position, and benzo-dibenzothiophenyl bonded in 4- position, where “fluorenyl” and “benzofluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.

[0114] For clarity, “benzofluorenyl” bonded in one of positions 1 , 2, 3 and 4 is understood understood to be a group conforming to one of the following formulae:

[0115] For clarity, “benzo-dibenzothiophenyl” bonded in one of positions 1 , 2, 3 and 4 is understood to be a group conforming to one of the following formulae: Foreignfiling text P24-253-SEC-WO01 20251217

[0116] - 19 -

[0117] 5

[0118] Among these, formula B-DBF-2 is preferred.

[0119] Ortho-biphenyl, substituted with radicals R8, is less preferred as Ar1, so particularly preferred is the above list without ortho-biphenyl, substituted with radicals R8.

[0120] In a more preferred embodiment, Ar1is selected from 1-naphthyl, 2-naphthyl, 1- phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 1-fluorenyl, 2- fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1-position,

[0121] 15 benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1 -dibenzofuranyl, 1 -dibenzothiophenyl, 2- dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3-dibenzothiophenyl, 4- dibenzofuranyl, 4-dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1-position, benzo-dibenzothiophenyl bonded in 1-position, benzo-dibenzofuranyl bonded in 2-

[0122] 20 position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo-dibenzothiophenyl bonded in 3-position, benzo- dibenzofuranyl bonded in 4-position, benzo-dibenzothiophenyl bonded in 4-position, where “fluorenyl” and “benzofluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.

[0123] In an even more preferred embodiment, Ar1is selected from 1-naphthyl, 2-naphthyl,

[0124] 30 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 1-fluorenyl,

[0125] 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 1 -dibenzofuranyl, 1-dibenzothiophenyl, 2- dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3-dibenzothiophenyl, 4- Foreignfiling text P24-253-SEC-WO01 20251217

[0126] - 20 - dibenzofuranyl, 4-dibenzothiophenyl, where “fluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from

[0127] 5 methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.

[0128] Most preferably, Ar1is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 1 -dibenzofuranyl, 1 -dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3- dibenzofuranyl, 3-dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, where “fluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl,

[0129] 15 naphthyl and biphenyl. Highest preference is for Ar1to be selected from 2- dibenzofuranyl and 2-fluorenyl, where the latter is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl.

[0130] Highly preferred embodiments of group Ar1are listed in the following, where each of

[0131] 20 the groups is substituted with radicals R8in the positions depicted as unsubstituted:

[0132] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0133] 5

[0134] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0135] 5

[0136] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0137] 5

[0138] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0139] -24-

[0140] 5

[0141] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0142] 5

[0143] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0144] 5

[0145] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0146] - 27 -

[0147] 5

[0148] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0149] 5

[0150] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0151] 5

[0152] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0153] 5

[0154] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0155] -31 -

[0156] 5

[0157] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0158] 5

[0159] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0160] 5

[0161] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0162] 5

[0163] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0164] 5

[0165] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0166] 5

[0167] 30

[0168] Preferably, in the groups of the above table, R8is, identically or differently, H or D, most preferably it is H. Foreignfiling text P24-253-SEC-WO01 20251217

[0169] - 37 -

[0170] Within the above list, Ar1-4 is less preferred. So, particularly preferred is the above list of embodiments of Ar1, without Ar1-4.

[0171] From the above list, groups Ar1-1 to Ar1-19, Ar1-48 to Ar1-102, Ar1-139 to Ar1-210,

[0172] 5 Ar1-255 to Ar1-265, Ar1-272 to Ar1-279 and Ar1-283 to Ar1-292 are particularly preferred. Within the above list, Ar1-4 is less preferred. So, particularly preferred is the above list of embodiments of Ar1, without Ar1-4.

[0173] According to an alternative embodiment, from the above list, groups Ar1-48, Ar1-49, Ar1-53 to Ar1-56, Ar1-60 to Ar1-70, Ar1-81 , Ar1-84, Ar1-92, Ar1-100, Ar1-139 to Ar1- 143, Ar1-145, Ar1-146, Ar1-150, Ar1-152, Ar1-156, Ar1-160, Ar1-161 , Ar1-163 to Ar1- 175, Ar1-177, Ar1-180, Ar1-181 , Ar1-183, Ar1-195, Ar1-196, Ar1-199 to Ar1-210, Ar1- 257, Ar1-258, Ar1-261 , Ar1-265 to Ar1-270, and Ar1-283 to Ar1-292 are preferred.

[0174] 15 R° is preferably selected, identically or differently, from straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 6 to 24 aromatic ring atoms, where two radicals R° may be connected to each other to form a ring; and where the said straight-chain alkyl groups, the said branched or cyclic alkyl groups and the said aromatic ring systems

[0175] 20 and heteroaromatic ring systems are substituted by radicals R9. R9in such cases are preferably selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F. Most preferably, R° is selected, identically or differently, from methyl, deuterated methyl, fluorine-substituted methyl, phenyl, and biphenyl, where each of phenyl and biphenyl are optionally substituted by one or more selected from methyl, deuterated methyl, and fluorine-substituted methyl.

[0176] R1to R6are preferably selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl

[0177] 30 groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where Foreignfiling text P24-253-SEC-WO01 20251217

[0178] - 38 - the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9. Radicals R9are preferably selected in such cases, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, alkyl groups having 1 to 20 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F. Most preferably, R1to

[0179] 5 R6are selected, identically or differently, from H, D, and aromatic ring systems having 6 to 24 aromatic ring atoms, which are substituted by radicals R9. Radicals R9are preferably selected in the cases of this paragraph, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, alkyl groups having 1 to 20 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F. With highest preference, radicals R1to R6are selected, identically or differently, from H and D.

[0180] Preferably, in the compounds according to formula (I), none, one, two or three groups selected from groups R1to R4are not H or D. More preferably, none, one or

[0181] 15 two groups selected from groups R1to R4are not H or D. Even more preferably, none or one group selected from groups R1to R4are not H or D. Most preferably, all of the groups selected from groups R1to R4are H or D.

[0182] R7is preferably selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups

[0183] 20 having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9. More preferably, R7is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9. Radicals R9are preferably selected the cases of this paragraph, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, alkyl groups having 1 to 20 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or

[0184] 30 more groups selected, identically or differently, from D and F. Most preferably, R7is selected, identically or differently, from H and D. Foreignfiling text P24-253-SEC-WO01 20251217

[0185] - 39 -

[0186] R8is preferably selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said

[0187] 5 alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9. More preferably, R8is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9. Radicals R9are preferably selected in such cases, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F. Most preferably, R8is selected,

[0188] 15 identically or differently, from H and D.

[0189] Radicals R9are preferably selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)s, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F.

[0190] 20

[0191] Preferably, the above preferred embodiments of R° to R9apply in combination.

[0192] According to a preferred embodiment, formula (I) conforms to one of formulae (1-1) to (I-8) shown below

[0193] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0194] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0195] 5

[0196] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0197] - 42 -

[0198] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0199] 5

[0200] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0201] - 44 - where the variable groups conform to their definitions as laid out above, and preferably conform to the preferable embodiments as laid out above. Particularly preferably, X1is O at each occasion in the above formulae. Among the above formulae, formulae (1-1) to (I-4) are preferred, in particular formula (I-2). According to another preferred embodiment, formulae (I-2) and (I-6) are preferred, in particular

[0202] 5 formula (I-2).

[0203] According to a preferred embodiment, the compound according to the present application conforms to formula (I-2) or formula (I-6), preferably formula (I-2), and the variable groups are defined as follows:

[0204] - X1is O; and

[0205] - X2is O; and

[0206] - L1is phenylene;

[0207] - Ar1is selected from phenyl, ortho-biphenyl, meta-biphenyl, para-biphenyl, 1- naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl

[0208] 15 bonded in 1 -position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1 -dibenzofuranyl, 1- dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3- dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1 -position, benzo-dibenzothiophenyl bonded in 1 -position, benzo- dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl bonded in 2-position,

[0209] 20 benzo-dibenzofuranyl bonded in 3-position, benzo-dibenzothiophenyl bonded in 3- position, benzo-dibenzofuranyl bonded in 4-position, benzo-dibenzothiophenyl bonded in 4-position, and phenyl, which is substituted in para, meta or ortho position, preferably in para-position, with a group selected from 1-naphthyl, 2- naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in

[0210] 1 -position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3- position, benzofluorenyl bonded in 4-position, 1 -dibenzofuranyl, 1- dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3- dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1 -position, benzo-dibenzothiophenyl bonded in 1 -position, benzo- dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl bonded in 2-position,

[0211] 30 benzo-dibenzofuranyl bonded in 3-position, benzo-dibenzothiophenyl bonded in 3- position, benzo-dibenzofuranyl bonded in 4-position, and benzo-dibenzothiophenyl Foreignfiling text P24-253-SEC-WO01 20251217

[0212] - 45 - bonded in 4-position, where “fluorenyl” and “benzofluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems,

[0213] 5 more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl; and

[0214] - R° is selected, identically or differently, from methyl, deuterated methyl, fluorinesubstituted methyl, phenyl, and biphenyl, where each of phenyl and biphenyl are optionally substituted by one or more selected from methyl, deuterated methyl, and fluorine-substituted methyl; and

[0215] - R1to R6are selected, identically or differently, from H, D, and aromatic ring systems having 6 to 24 aromatic ring atoms, which are substituted by radicals R9; and

[0216] - R7is selected, identically or differently, from straight-chain alkyl groups having 1 to

[0217] 15 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9; and

[0218] - R8is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring

[0219] 20 systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9; and

[0220] - R9is selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F.

[0221] According to a preferred embodiment of the invention, the compounds are partially or completely deuterated. Partial deuteration is understood to mean that some, but not all hydrogen (=protium) atoms are replaced by deuterium atoms. Complete

[0222] 30 deuteration is understood to mean that all hydrogen (=protium) atoms are replaced by deuterium atoms. Partially deuterated compounds can be pure compounds Foreignfiling text P24-253-SEC-WO01 20251217

[0223] - 46 - regarding their isotopic composition, for example if a fully deuterated phenyl group is bonded to a non-deuterated residual compound structure. In the alternative, partially deuterated compounds can be so-called statistically deuterated compounds, meaning that they consist of a multitude of different H / D-isotopic isomers. H / D-isotopic isomers are understood to be isotopologues, i.e. compounds

[0224] 5 which only differ in the isomers H and D present, and otherwise have the identical chemical structure.

[0225] Preferably, the compounds have a deuteration degree of at least 25%, more preferably of at least 50%, even more preferably of at least 80%, and most preferably of 100%. “Deuteration degree” here means the ratio of deuterium atoms over the sum of deuterium atoms and protium atoms. The deuteration degree can be calculated for a single molecule, or for a compound which is composed of a multitude of H / D-isotopic isomers. In technical practice, deuterated compounds according to the present invention are often composed of a multitude of H / D-

[0226] 15 isotopic isomers, as mentioned above. If the synthesis process yields such H / D- isotopic isomers, they are, for convenience, typically not isolated, but only the mixture resulting from the synthesis process is used. For such mixtures, the deuteration degree can also be measured and calculated, by dividing the total number of deuterium atoms present in the mixture of H / D-isotopic isomers, by the sum of the total number of deuterium atoms and the total number of protium atoms.

[0227] 20 Measurement can be done by NMR or by mass spectroscopy. “Deuteration degree” for these mixtures of H / D-isotopic isomers therefore means the result of the above measurement and calculation.

[0228] According to an alternative preferred embodiment of the invention, the compounds are non-deuterated. This is understood to mean that their chemical structure does not comprise any D atoms.

[0229] Preferred compounds according to formula (I) are the following:

[0230] 30 Foreignfiling text_P24-253-SEC-WO01_20251217

[0231] - 47 -

[0232] 5

[0233] 15

[0234] 20

[0235] 25 Foreignfiling text_P24-253-SEC-WO01_20251217

[0236] -48-

[0237] 20

[0238] 25 Foreignfiling text P24-253-SEC-WO01 20251217

[0239] 5

[0240] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0241] -50-

[0242] 5

[0243] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0244] - 51 -

[0245] 5

[0246] 30 Foreignfiling text_P24-253-SEC-WO01_20251217

[0247] - 52 -

[0248] 5

[0249] 20

[0250] 25 Foreignfiling text P24-253-SEC-WO01 20251217

[0251] 5

[0252] 30 Foreignfiling text_P24-253-SEC-WO01_20251217

[0253] -54-

[0254] 10

[0255] 20

[0256] 25 Foreignfiling text_P24-253-SEC-WO01_20251217

[0257] -55-

[0258] 10

[0259] 20

[0260] 25 Foreignfiling text_P24-253-SEC-WO01_20251217

[0261] -56-

[0262] 10

[0263] 20

[0264] 25 Foreignfiling text_P24-253-SEC-WO01_20251217

[0265] - 57 -

[0266] 5

[0267] 10

[0268] 15

[0269] 20

[0270] 25

[0271] 30 Foreignfiling text_P24-253-SEC-WO01_20251217

[0272] -58- Foreignfiling text_P24-253-SEC-WO01_20251217

[0273] -59-

[0274] 10

[0275] 20

[0276] 25 Foreignfiling text P24-253-SEC-WO01 20251217

[0277] 5

[0278] The compounds according to formula (I) can be prepared, using established procedures of organic synthetic chemistry. In particular, for the synthesis of the

[0279] 15 compounds of formula (I), the reaction types of Buchwald coupling, and Suzuki coupling, are used, as well as Grignard reaction and cyclization reaction.

[0280] A particularly preferred method for synthesis of the compounds of formula (I) is shown in the following. This method comprises a first step (Scheme 1), in which by a Grignard reaction and cyclization reaction based on an aromatic electrophilic

[0281] 20 substitution reaction, the basic heteroaromatic structure of the spiro-xanthene or spiro-thioxanthene is formed. The intermediate product of the synthesis is a halogen-substituted spiro-xanthene or spiro-thioxanthene derivative.

[0282] Scheme 1 Foreignfiling text P24-253-SEC-WO01 20251217

[0283] - 61 -

[0284] In the second step, either of a) the Suzuki reaction of Scheme 2A is performed, or the Buchwald reaction of Scheme 2B is performed.

[0285] In the Suzuki reaction of Scheme 2A, the intermediate product of Scheme 1 , the halogen-substituted spiro-xanthene or spiro-thioxanthene derivative, is reacted with a triarylamino derivative, which has a boronic acid reactive group. Thereby, a

[0286] 5 compound according to formula (I) is formed which has an aromatic ring system or heteroaromatic ring system as a linker between the spiro-xanthene or spiro- thioxanthene moiety and the amino group.

[0287] Scheme 2A

[0288] Ar-

[0289] X1is 0 or S

[0290] 15 X2is 0 or S

[0291] X = Cl or Br

[0292] L = aromatic or heteroaromatic ring system

[0293] R = organic substitution group, preferably alkyl; the groups R can also be connected to each other to form a ring

[0294] An = aromatic or heteroaromatic ring system

[0295] 20

[0296] In the Buchwald reaction according to Scheme 2B, the intermediate product of Scheme 1 , the halogen-substituted spiro-xanthene or spiro-thioxanthene derivative, is reacted with a diarylamino compound. Thereby, a compound according to formula (I) is formed, which has the spiro-xanthene or spiro-thioxanthene moiety and the amino group directly connected to each other.

[0297] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0298] Scheme 2B

[0299] 5

[0300] X-i is 0 or S

[0301] X2is 0 or S

[0302] X = Cl or Br

[0303] An = aromatic or heteroaromatic ring system

[0304] The present application therefore is also directed at a process for preparation of a compound according to above-defined formula (I), characterized in that in a first step, a xanthene-one or thioxanthene-one derivative having a halogen substituent on one of its aromatic rings is reacted with a diphenyl ether or diphenyl thioether halogenide, where the diphenyl ether or diphenyl thioether halogenide reacts in a

[0305] 15 Grignard reaction and the resulting metal organic compound reacts in a nucleophilic addition to the carbonyl group of the xanthene-one or thioxanthene-one derivative. The resulting product of the nucleophilic addition which is a tertiary alcohol is then cyclized under acidic conditions, in an electrophilic substitution reaction which is an alkylation of one of the benzene rings of the diphenylether or diphenylthioether

[0306] 20 educt, by which the spiro basic structure is formed. The process is further characterized in that in a second step, the intermediate product of the first step, the halogen substituted spiro-xanthene or spiro-thioxanthene derivative, is either reacted in a Suzuki coupling reaction with an aromatic or heteroaromatic boronic acid derivative, or else it is reacted in a Buchwald coupling reaction with a diarylamine derivative.

[0307] The above-described compounds of the invention, especially compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic ester, may find use as monomers for production of corresponding oligomers, dendrimers or polymers. Suitable reactive leaving groups are, for

[0308] 30 example, bromine, iodine, chlorine, boronic acids, boronic esters, amines, alkenyl or alkynyl groups having a terminal C-C double bond or C-C triple bond, oxiranes, oxetanes, groups which enter into a cycloaddition, for example a 1 ,3-dipolar Foreignfiling text P24-253-SEC-WO01 20251217

[0309] - 63 - cycloaddition, for example dienes or azides, carboxylic acid derivatives, alcohols and silanes.

[0310] The invention therefore further provides oligomers, polymers or dendrimers containing one or more compounds of formula (I), wherein the bond(s) to the

[0311] 5 polymer, oligomer or dendrimer may be localized at any desired positions substituted by any of R1to R8in formula (I). According to the linkage of the compound of formula (I), the compound is part of a side chain of the oligomer or polymer or part of the main chain.

[0312] Further technical details of such oligomers, polymers and dendrimers containing one or more compounds of formula (I) are as disclosed on p. 49, 1. 26 - p. 51 , 1. 17 of W02020 / 109434A1. The cited disclosure is herewith incorporated into the present application in its entirety.

[0313] 15 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 benzoate, mesitylene, tetralin, veratrole, THF,

[0314] 20 methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 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, alpha-terpineol, benzothiazole, butyl benzoate, 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 dimethyl ether, 2-isopropylnaphthalene,

[0315] 30 pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1 ,1-bis(3,4- dimethylphenyl)ethane, or mixtures of these solvents. Foreignfiling text P24-253-SEC-WO01 20251217

[0316] - 64 -

[0317] The invention therefore further provides a formulation, especially a solution, dispersion or emulsion, comprising at least one compound of formula (I) or at least one polymer, oligomer or dendrimer containing at least one unit of formula (I) and at least one solvent, preferably an organic solvent. The way in which such solutions

[0318] 5 can be prepared is known to those skilled in the art.

[0319] The compound of formula (I) is suitable for use in an electronic device, especially an organic electroluminescent device (OLED). Depending on the substitution, the compound of the formula (I) can be used in different functions and layers. Preference is given to use as a hole-transporting material in a hole-transporting layer and / or as matrix material in an emitting layer, more preferably in combination with a phosphorescent emitter.

[0320] The invention therefore further provides for the use of a compound of formula (I) in

[0321] 15 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

[0322] 20 organic electroluminescent devices (OLEDs).

[0323] The invention further provides an electronic device comprising at least one compound of formula (I). This electronic device is preferably selected from the above-mentioned devices.

[0324] 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 of formula (I) is present in the device. Preference is given to an organic electroluminescent device comprising anode, cathode and at least one emitting layer, characterized in that at least one

[0325] 30 organic layer in the device, selected from hole-injection layers, hole-transporting layers, electron-blocking layers and emitting layers, preferably selected from hole- Foreignfiling text P24-253-SEC-WO01 20251217

[0326] - 65 - injection layers, hole-transporting layers, and electron-blocking layers, comprises at least one compound of formula (I).

[0327] A hole-transporting layer is understood here to mean all layers disposed between anode and emitting layer, preferably hole injection layers, hole transport layers and

[0328] 5 electron blocking layers. 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, but directly adjoins a hole injection layer, and which does not directly adjoin the emitting layer on its anode side, but has at least one layer between it and the emitting layer. An electron blocking layer is understood here to mean a layer which is between the anode and emitting layer and directly adjoins the emitting layer. An electron blocking layer preferably has a high-energy LIIMO and hence prevents electrons from exiting from the emitting layer. According to another possible embodiment, there are only two layer between anode and emitting layer, the first of

[0329] 15 which is directly adjoining the anode and is termed hole injection layer, and the second of which is positioned between the hole injection layer and the emitting layer and is directly adjoining both of them. In such case, the second layer is also termed a hole transport layer, and typically not termed an electron blocking layer, although it directly adjoins the emitting layer on its anode side.

[0330] 20 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 blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking 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 device is a fluorescent or phosphorescent electroluminescent device.

[0331] The sequence of layers in the electronic device is preferably as follows:

[0332] 30 -anode-

[0333] -hole injection layer- Foreignfiling text P24-253-SEC-WO01 20251217

[0334] - 66 -

[0335] -hole transport layer-

[0336] -optionally further hole transport layers-

[0337] -electron blocking layer-

[0338] - optionally further electron blocking layers-

[0339] -emitting layer-

[0340] 5

[0341] -optionally hole blocking layer-

[0342] -electron transport layer-

[0343] -electron injection layer- -cathode-.

[0344] Most preferable is the following layer sequence:

[0345] -anode-

[0346] -hole injection layer-

[0347] -hole transport layer-

[0348] -electron blocking layer-

[0349] 15 -emitting layer-

[0350] -hole blocking layer-

[0351] -electron transport layer-

[0352] -electron injection layer- -cathode-.

[0353] 20 An alternative, highly preferably layer sequence is the following one: -anode-

[0354] -optional one or more hole injection layers-

[0355] -optional one of more hole transport layers-

[0356] -first electron blocking layer-

[0357] -second electron blocking layer-

[0358] -emitting layer-

[0359] -optional hole blocking layer-

[0360] -electron transport layer-

[0361] -electron injection layer-

[0362] -cathode-. In this case, the emitting layer is preferably a green or red

[0363] 30 phosphorescent emitting layer. Foreignfiling text P24-253-SEC-WO01 20251217

[0364] - 67 -

[0365] In the embodiments of layer stacks mentioned above, not all the layers mentioned need to be present and / or further layers may additionally be present.

[0366] The organic electroluminescent device of the invention may contain two or more emitting layers. More preferably, these emission layers have several emission

[0367] 5 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 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

[0368] 15 individually which emits over a broad wavelength range may also be suitable.

[0369] The emitting layer of the OLED is preferably a green emitting layer, a blue emitting layer or a red emitting layer, most preferably it is a green emitting layer or a blue emitting layer. The green emitting layer is preferably a phosphorescent emitting layer. The red emitting layer is preferably a phosphorescent emitting layer. The blue

[0370] 20 emitting layer is preferably a fluorescent emitting layer.

[0371] It is preferable that the compound of the formula (I) is used as hole transport material. The emitting layer here may be a fluorescent emitting layer, or it may be a phosphorescent emitting layer. The emitting layer is preferably a blue-fluorescing layer or a green-phosphorescing layer. This is especially preferred if the compound according to formula (I) is used in an electron-blocking layer, i.e. adjacent to the emitting layer on its anode side.

[0372] When the device containing the compound of the formula (I) contains a phosphorescent emitting layer, it is preferable that this layer contains two or more,

[0373] 30 preferably exactly two, different matrix materials (mixed matrix system). Preferred embodiments of mixed matrix systems are described in detail further down. Foreignfiling text P24-253-SEC-WO01 20251217

[0374] - 68 -

[0375] If the compound of formula (I) is used as hole transport material in a hole transport layer, a hole injection layer or an electron blocking 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.

[0376] 5

[0377] In a preferred embodiment, a hole-transporting layer comprising the compound of the formula (I) 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 most preferably selected from the preferred embodiments of hole transport materials that are specified further down. In the preferred embodiment described, the compound of the formula (I) 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%. Preferred are embodiments such as

[0378] 15 the ones disclosed in WO2014 / 044344A1, WO 2020 / 225069A1 and W02020 / 225071A1.

[0379] In an alternative preferred embodiment, a hole injection layer or a hole transporting layer, preferably a hole injection layer, comprising the compound of the formula (I) additionally comprises one or more further compounds selected from electron¬

[0380] 20 transporting compounds and compounds having a wide band gap. A wide band gap is understood to mean a large energy difference between HOMO and LIIMO. These further compounds are preferably selected from the compounds listed in the table of specific compounds on p. 85-106 of WO2024 / 133366A1, where the electrontransporting compounds are listed on p. 85-99 of this table, and the compounds having a wide band gap are listed on p. 100-106 of this table. Most preferably, the compound selected from electron-transporting compounds is the one depicted on p. 85, bottom row of the table, on the left of the above-mentioned list of WO2024 / 133366A1.

[0381] Most preferably, the compound selected from compounds having a wide band gap

[0382] 30 is the one depicted on p. 100, third row, in the middle of the above-mentioned list of WO2024 / 133366A1. Foreignfiling text P24-253-SEC-WO01 20251217

[0383] - 69 - ln the preferred embodiment described, the compound of the formula (I) and the one or more further compound selected from electron-transporting compounds and compounds having a wide band gap are preferably each present in a proportion of at least 10%, more preferably each in a proportion of at least 20%. Preferably, in

[0384] 5 addition, a p-dopant is present in the hole injection layer. Preferred, regarding the embodiments of this paragraph, are embodiments such as the ones disclosed in WO2024 / 133366A1.

[0385] In a preferred embodiment, a hole-transporting layer comprising the compound of the formula (I) 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.

[0386] 15 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

[0387] 20 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 carboxylate ligands.

[0388] 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.

[0389] Preferred p-dopants are furthermore the compounds which are explicitly disclosed

[0390] 30 in the table on p. 86-87 of WO2021 / 156323A1. Foreignfiling text P24-253-SEC-WO01 20251217

[0391] - 70 -

[0392] 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

[0393] 5 preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylene derivative as described in US 2007 / 0092755.

[0394] The compound of the formula (I) may be present in a hole injection layer, in a hole transport layer and / or in an electron blocking 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-doped, meaning that it is in mixed form with a p-dopant, as described above, in the layer.

[0395] The compound of the formula (I) is preferably present in an electron blocking layer.

[0396] 15 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 compound. According to another embodiment, which is preferred under certain circumstances, the compound of the formula (I) is present in mixture with another compound, which conforms to the formula (I), or which does not conform to the formula (I), in an electron-blocking layer.

[0397] 20

[0398] According to a preferred embodiment, the OLED comprising a compound of formula (I) comprises two electron blocking layers, which are arranged sequentially, and in contact with each other, between anode and the emitting layer of the OLED, where one of the two electron blocking layers contacts the emitting layer on the anode side of the emitting layer. In such case, it is preferred that one of the two electron blocking layers, preferably the one of the two electron blocking layers which is contacts the emitting layer, comprises a compound of formula (I). Preferably, in the setups described in this paragraph, the OLED is a phosphorescent green or red, particularly preferably phosphorescent green light emitting OLED, and the emitting layer which contacts the electron blocking layer is a green or red phosphorescent

[0399] 30 emitting layer, particularly preferably a green phosphorescent emitting layer. Further, preferably, the one electron blocking layer of the two electron blocking Foreignfiling text P24-253-SEC-WO01 20251217

[0400] - 71 - layers which is adjacent to the emitting layer, is thinner than the other one of the two electron blocking layers. In particular, the former electron blocking layer preferably has a thickness of 5 nm -10 nm, and the latter electron blocking layer preferably has a thickness of 20 nm - 60 nm, more preferably 20 nm - 40 nm, most preferably 20 nm - 30 nm. Further, preferably, the HOMO of the material of the one electron

[0401] 5 blocking layer of the two electron blocking layers which is adjacent to the emitting layer is lower than the HOMO of the material of the other electron blocking layer. Lower in this case means more negative value of the HOMO. Such OLED stack comprising the compound of formula (I) as described in this paragraph has the advantage of improved capacitance and low leak current.

[0402] In an alternative preferred embodiment, the compound of the formula (I) 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

[0403] 15 green-phosphorescing compounds.

[0404] 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 preferably between 85.0% and 97.0% by volume.

[0405] 20 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.

[0406] 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.

[0407] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0408] - 72 -

[0409] It is preferable that the compounds of formula (I) are used as a component of mixed matrix systems, preferably for phosphorescent emitters. The mixed matrix 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

[0410] 5 having electron-transporting 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 materials). The compound of the formula (I) in a mixed matrix system is preferably the matrix material having hole-transporting properties. Correspondingly, when the compound of the formula (I) 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 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.

[0411] 15

[0412] 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.

[0413] 20 Preference is given to using the following material classes in the above-mentioned layers of the device:

[0414] Phosphorescent emitters, for use in an emitting layer:

[0415] 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.

[0416] Suitable phosphorescent emitters are especially compounds which, when suitably

[0417] 30 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 Foreignfiling text P24-253-SEC-WO01 20251217

[0418] - 73 -

[0419] 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.

[0420] 5

[0421] In the context of the present invention, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds.

[0422] 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 examples of suitable phosphorescent emitters are those shown in the table on p.100-104 of WO2023 / 025971A2.

[0423] Fluorescent emitters, for use in an emitting layer:

[0424] 15

[0425] 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

[0426] 20 system, more preferably having at least 14 aromatic 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 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 the diarylamino groups are bonded to the pyrene preferably in the 1 position or 1 ,6 position. Further preferred emitting compounds are indenofluoreneamines or -

[0427] 30 diamines, benzoindenofluoreneamines or -diamines, and dibenzoindenofluoreneamines or -diamines, and indenofluorene derivatives having Foreignfiling text P24-253-SEC-WO01 20251217

[0428] - 74 - fused aryl groups. Likewise preferred are pyrenearylamines. Likewise preferred are benzoindenofluoreneamines, benzofluoreneamines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives joined to furan units or to thiophene units.

[0429] 5

[0430] Matrix materials for fluorescent emitters, for use in an emitting layer:

[0431] 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 electronconducting compounds, 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

[0432] 15 atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Very 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

[0433] 20 another.

[0434] Matrix materials for phosphorescent emitters, for use in an emitting layer:

[0435] Preferred matrix materials for phosphorescent emitters are, as well as the compounds of the formula (I), 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

[0436] 30 carbazole derivatives, triphenylene derivatives, or lactams. Foreignfiling text P24-253-SEC-WO01 20251217

[0437] - 75 -

[0438] Electron-transporting materials, for use in an electron transporting layer or holeblocking layer:

[0439] 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

[0440] 5 these layers according to the prior art.

[0441] 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 Alqa, 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.

[0442] 15

[0443] Preferred electron transport and electron injection materials are those shown in the table on p. 73-75 of W02020 / 109434A1.

[0444] Hole-transporting materials, for use in a hole injection layer, hole transport layer or electron blocking layer:

[0445] 20

[0446] Further compounds which, in addition to the compounds of the formula (I), are preferably 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 spirodibenzothiophenes, phenanthrenediarylamines, spirotribenzotropolones, spirobifluorenes having metaphenyldiamine groups, spirobisacridines, xanthenediarylamines, and 9,10- dihydroanthracene spiro compounds having diarylamino groups. Preferred hole¬

[0447] 30 transporting compounds are those shown the table on p. 76-80 of W02020 / 109434A1. Foreignfiling text P24-253-SEC-WO01 20251217

[0448] - 76 -

[0449] 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

[0450] 5 metal or alkaline earth 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 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 also the corresponding oxides or carbonates (e.g. Li F, U2O, BaF2, MgO, NaF, CsF, CS2CO3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose. The layer

[0451] 15 thickness of this layer is preferably between 0.5 and 5 nm.

[0452] 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. AI / Ni / NiOx, AI / PtOx) may also be

[0453] 20 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 (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 oxide, molybdenum oxide or vanadium oxide.

[0454] In a preferred embodiment, the electronic device is characterized in that one or

[0455] 30 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 Foreignfiling text P24-253-SEC-WO01 20251217

[0456] - 77 - less than 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.

[0457] 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

[0458] 5 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).

[0459] 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 more preferably LITI (light-induced thermal imaging, thermal

[0460] 15 transfer printing) or inkjet printing. For this purpose, soluble compounds of formula (I) are needed. High solubility can be achieved by suitable substitution of the compounds.

[0461] 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

[0462] 20 method.

[0463] 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.

[0464] According to the invention, the electronic devices comprising one or more compounds of formula (I) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications.

[0465] In the text, if there is reference made to formula (I), in each case this equally applies

[0466] 30 to the preferred embodiments of formula (I), such as formula (1-1) etc. Foreignfiling text P24-253-SEC-WO01 20251217

[0467] - 78 -

[0468] Patent examples

[0469] A) Synthesis examples

[0470] The compounds can be prepared by standard reactions of synthetic organic

[0471] 5 chemistry, such as transition metal catalyzed coupling reactions, preferably Buchwald couplings.

[0472] A preferred procedure for synthesis of compounds, in which diamine is attached to bromo-9,9’-spirobi-9H-xanthene, is shown in Scheme 2B above.

[0473] According to an alternative procedure, derivatives of formula (I) which have an aryl group as a spacer group L1between the spirobixanthene and the amine nitrogen can be prepared. A suitable reaction scheme for this is shown in Scheme 2A above. In some cases, the aryl-substituted spirobixanthene which has a reactive group on the aryl, may also be available commercially.

[0474] Starting materials as aromatic halides and diarylamines are commercially available.

[0475] In the following reactions, 9,9’-spirobi-9H-xanthene derivatives are coupled to diaryl amine in a Buchwald reaction. The following syntheses are, unless indicated otherwise, carried out under a protective-gas atmosphere in dried solvents.

[0476] 30 Compound 1

[0477] Preparation of compound 1 Foreignfiling text P24-253-SEC-WO01 20251217

[0478] - 79 -

[0479] 30 g (70.21 mmol) of 2-Bromo-9,9’-spirobi-9H-xanthene and 26.4 g (70.21 mmol) of 2225845-23-6 are suspended in 500 mL of toluene under Ar atmosphere. 0.3 g (1 .4 mmol) of Pd(OAc)2 are added to the flask and stirred under Ar atmosphere, then 0.7 g (3.5 mmol) of tri-tert-butylphosphine and 16.8 g (175.0 mmol) of sodium t-butoxide are added to the flask. The reaction mixture is stirred under reflux for 24 h. After

[0480] 5 cooling, the organic phase is separated off, washed three times with 200 mL of water, dried over magnesium sulfate, filtered and subsequently evaporated to dryness. The residue is purified by column chromatography on silica gel using a mixture of dichloromethan / heptane (1 :3). The yield is 21.7 g (30.1 mmol), corresponding to 43% of theory.

[0481] The following syntheses of compounds 2-14 are carried out under same reaction conditions.

[0482] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0483] 5

[0484] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0485] - 81 -

[0486] 5

[0487] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0488] 5

[0489] 30 Foreignfiling text_P24-253-SEC-WO01_20251217

[0490] - 83 -

[0491] 5

[0492] 10

[0493] 15

[0494] B) Device examples

[0495] 1 ) General production process for the OLEDs and characterization of the OLEDs

[0496] 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.

[0497] The OLEDs basically have the following layer structure: substrate I hole injection layer (HIL) I hole transport layer (HTL) I electron blocker layer (EBL) I emission layer (EML) I electron transport layer, optionally with second layer (ETL) I electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. 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. Foreignfiling text P24-253-SEC-WO01 20251217

[0498] - 84 -

[0499] 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 dopant which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details

[0500] 5 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%.

[0501] In an analogous manner, the electron transport layer and the hole injection layer also consist of a mixture of two materials. The chemical structures of the materials that are used in the OLEDs are shown in Table 1 .

[0502] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the external quantum efficiency (EQE,

[0503] 15 measured in %) as a function of the luminance, calculated from current- voltage-luminance characteristics assuming Lambertian radiation characteristics, and the lifetime are determined. The parameter EQE @ 10 mA / cm2refers to the external quantum efficiency which is attained at 10 mA / cm2. The parameter U @ 10 mA / cm2refers to the

[0504] 20 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 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.

[0505] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0506] 5

[0507] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0508] 5

[0509] 30 Foreignfiling text P24-253-SEC-WO01 20251217

[0510] 2) Inventive OLEDs containing a compound of the formula (I) in the EBL of green-phosphorescing OLEDs

[0511] Devices as shown in the following table are produced:

[0512] 5

[0513] Table 2: Structure of the OLEDs

[0514] In the device setup shown above, the inventive compounds give good voltages, efficiencies and lifetimes for the OLEDs. The performance that has been found for the inventive compounds is above the level of the current standard in the prior art, taking operating voltage, efficiency and

[0515] 30 lifetime into account. Foreignfiling text P24-253-SEC-WO01 20251217

[0516] - 88 -

[0517] Important to note, the compounds according to the present application, which have a 1 -dibenzofuranyl group bonded to the amine nitrogen, show a great improvement in efficiency (e.g. HT-F) compared to otherwise identical compounds (C1 ), which have a 3-dibenzofuranyl group bonded to the

[0518] 5 amine nitrogen.

[0519] 15

[0520] 20

[0521] 30

Claims

Foreignfiling text P24-253-SEC-WO01 20251217Patent Claimsformula (I), where the following applies to the variable groups:X1is selected, identically or differently, from O and S;X2is selected from O, S, C(R°)2 and Si(R°)2;L1is selected from single bond, aromatic ring systems having 6 to 4020 aromatic ring atoms which are substituted with radicals R7, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted with radicals R7;Ar1is selected from aromatic ring systems having 6 to 40 aromatic ring atoms which are substituted with radicals R8, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted with radicals R8;R° is selected, identically or differently, from H, D, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two radicals R° may be connected to each other to form a ring; and where30 the said straight-chain alkyl groups, the said branched or cyclic alkylForeignfiling text P24-253-SEC-WO01 20251217- 90 - groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9;R1is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms,5 alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R1may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R2is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C15 atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R2may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring20 systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R3is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)s, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R3may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring30 systems are substituted by radicals R9, and where one or more CH2Foreignfiling text P24-253-SEC-WO01 20251217- 91 - groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R4is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms,5 alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R4may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R5is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)a, straight-chain alkyl or alkoxy groups having 1 to 20 C15 atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R5may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring20 systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R6is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)s, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R6may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring30 systems are substituted by radicals R9, and where one or more CH2Foreignfiling text P24-253-SEC-WO01 20251217- 92 - groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R7is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms,5 alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R7may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R8is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R9)a, straight-chain alkyl or alkoxy groups having 1 to 20 C15 atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R8may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring20 systems are substituted by radicals R9, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R9C=CR9-, -C=C-, Si(R9)2, NR9, -O-, or -S-;R9is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R10)3, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R9may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring30 systems are substituted by radicals R10, and where one or more CH2Foreignfiling text P24-253-SEC-WO01 20251217- 93 - groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by -R10C=CR10-, -C=C-, Si(R10)2, NR10, -O-, or -S-;R10is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl5 or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where the above-mentioned straight-chain alkyl or alkoxy groups, the above-mentioned branched or cyclic alkyl or alkoxy groups, the above-mentioned alkenyl or alkynyl groups, the above- mentioned aromatic ring systems having 6 to 40 aromatic ring atoms, and the above-mentioned heteroaromatic ring systems having 5 to 40 aromatic ring atoms may each be substituted by one or more selected from D, F, Cl, Br, I, and CN, and alkyl groups having 1 to 20 C atoms which are substituted by one or more selected from D, F, Cl, Br, I, and15 CN; where the group L1is bonded in one of the positions marked with 1 , 2, 3, 4.

2. Compound according to claim 1 , characterized in that both groups X1are O.20 3. Compound according to claim 1 or 2, characterized in that X2is O or C(R°)2.

4. Compound according to one or more of claims 1 to 3, characterized in that L1is selected from single bond and aromatic ring systems having 6 to 12 aromatic ring atoms, which are substituted with radicals R7, preferably characterized in that L1is a single bond.

5. Compound according to one or more of claims 1 to 4, characterized in that Ar1is selected from phenyl, ortho-biphenyl, meta-biphenyl, para-biphenyl, 1-naphthyl, 2- naphthyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 1- fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1-position,30 benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1 -dibenzofuranyl, 1 -dibenzothiophenyl, 2-Foreignfiling text P24-253-SEC-WO01 20251217- 94 - dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3-dibenzothiophenyl, 4- dibenzofuranyl, 4-dibenzothiophenyl, benzo-di benzofuranyl bonded in 1-position, benzo-dibenzothiophenyl bonded in 1-position, benzo-di benzofuranyl bonded in 2- position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo-dibenzothiophenyl bonded in 3-position, benzo-5 dibenzofuranyl bonded in 4-position, benzo-dibenzothiophenyl bonded in 4- position, spiroxanthene, spirobixanthene, and phenyl, which is substituted in para, meta or ortho position, preferably in para-position, with a group selected from 1- naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1-position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1- dibenzofuranyl, 1 -dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3- dibenzofuranyl, 3-dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, benzo-dibenzofuranyl bonded in 1-position, benzo-dibenzothiophenyl bonded in 1- position, benzo-dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl15 bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo- dibenzothiophenyl bonded in 3-position, benzo-dibenzofuranyl bonded in 4- position, and benzo-dibenzothiophenyl bonded in 4-position, where “fluorenyl” and “benzofluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with20 groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.

6. Compound according to one or more of claims 1 to 5, characterized in that Ar1is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 1 -dibenzofuranyl, 1- dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3-dibenzofuranyl, 3- dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, where “fluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any30 positions, where R8is preferably selected, identically or differently, from alkyl andForeignfiling text P24-253-SEC-WO01 20251217- 95 - aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.

7. Compound according to one or more of claims 1 to 6, characterized in that- R° is selected, identically or differently, from methyl, deuterated methyl, fluorine¬5 substituted methyl, phenyl, and biphenyl, where each of phenyl and biphenyl are optionally substituted by one or more selected from methyl, deuterated methyl, and fluorine-substituted methyl; and- R1to R6are selected, identically or differently, from H, D, and aromatic ring systems having 6 to 24 aromatic ring atoms, which are substituted by radicals R9; and- R7is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said15 aromatic and heteroaromatic ring systems are substituted by radicals R9; and- R8is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9; and20 - R9are selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F.

8. Compound according to one or more of claims 1 to 7, characterized in that it conforms to formula (I-2)30Foreignfiling text P24-253-SEC-WO01 20251217- 96 -Formula (I-2), where the variable groups are as defined in one of more of claims 1 to 7.

9. Compound according to claim 8, characterized in that the variable groups are defined as follows:15 - X1is O; and- X2is O; and- Ar1is selected from phenyl, ortho-biphenyl, meta-biphenyl, para-biphenyl, 1- naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzofluorenyl bonded in 1 -position, benzofluorenyl bonded in 2-position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position, 1-20 dibenzofuranyl, 1 -dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3- dibenzofuranyl, 3-dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl, benzo-di benzofuranyl bonded in 1 -position, benzo-dibenzothiophenyl bonded in 1- position, benzo-dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo- dibenzothiophenyl bonded in 3-position, benzo-dibenzofuranyl bonded in 4- position, benzo-dibenzothiophenyl bonded in 4-position, and phenyl, which is substituted in para, meta or ortho position, preferably in para-position, with a group selected from 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4- fluorenyl, benzofluorenyl bonded in 1 -position, benzofluorenyl bonded in 2- position, benzofluorenyl bonded in 3-position, benzofluorenyl bonded in 4-position,30 1 -dibenzofuranyl, 1 -dibenzothiophenyl, 2-dibenzofuranyl, 2-dibenzothiophenyl, 3- dibenzofuranyl, 3-dibenzothiophenyl, 4-dibenzofuranyl, 4-dibenzothiophenyl,Foreignfiling text P24-253-SEC-WO01 20251217- 97 - benzo-di benzofuranyl bonded in 1 -position, benzo-dibenzothiophenyl bonded in 1- position, benzo-dibenzofuranyl bonded in 2-position, benzo-dibenzothiophenyl bonded in 2-position, benzo-dibenzofuranyl bonded in 3-position, benzo- dibenzothiophenyl bonded in 3-position, benzo-dibenzofuranyl bonded in 4- position, and benzo-dibenzothiophenyl bonded in 4-position, where “fluorenyl” and5 “benzofluorenyl” is substituted with R8in the bridgehead positions, where R8is preferably selected from alkyl group and aromatic ring systems, more preferably from methyl and phenyl, and where the above groups can be substituted with groups R8in any positions, where R8is preferably selected, identically or differently, from alkyl and aromatic ring systems, more preferably from methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl; and- R° is selected, identically or differently, from methyl, deuterated methyl, fluorinesubstituted methyl, phenyl, and biphenyl, where each of phenyl and biphenyl are optionally substituted by one or more selected from methyl, deuterated methyl, and fluorine-substituted methyl; and15 - R1to R6are selected, identically or differently, from H, D, and aromatic ring systems having 6 to 24 aromatic ring atoms, which are substituted by radicals R9; and- R7is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems20 having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9; and- R8is selected, identically or differently, from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R9; and- R9is selected, identically or differently, from H, D, F, Si(Ph)3, Si(Me)3, alkyl groups having 1 to 10 C atoms, and alkyl groups having 1 to 10 C atoms, which are substituted with one or more groups selected, identically or differently, from D and F.30Foreignfiling text P24-253-SEC-WO01 20251217- 98 -10. Compound according to one or more of claims 1 to 9, characterized in that it has a deuteration degree of at least 25%.

11. Process of preparation of a compound according to one or more of claims 1 to 10, characterized in that in a first step, a xanthene-one or thioxanthene-one5 derivative having a halogen substituent on one of its aromatic rings is reacted with a diphenyl ether or diphenyl thioether halogenide, where the diphenyl ether or diphenyl thioether halogenide reacts in a Grignard reaction and the resulting metal organic compound reacts in a nucleophilic addition to the carbonyl group of the xanthene-one or thioxanthene-one derivative; and the resulting product of the nucleophilic addition which is a tertiary alcohol is then cyclized under acidic conditions, in an electrophilic substitution reaction which is an alkylation of one of the benzene rings of the diphenylether or diphenylthioether educt, by which the spiro basic structure is formed; further characterized in that in a second step, the intermediate product of the first step, the halogen substituted spiro-xanthene or15 spiro-thioxanthene derivative, is either reacted in a Suzuki coupling reaction with an aromatic or heteroaromatic boronic acid derivative, or it is reacted in a Buchwald coupling reaction with a diarylamine derivative.

12. Formulation comprising at least one compound according to one or more of Claims 1 to 10 and at least one solvent.2013. Organic electroluminescent device, comprising at least one compound according to one or more of Claims 1 to 10.

14. Organic electroluminescent device according to Claim 13, characterized in that it comprises an anode, cathode and at least one emitting layer, and in that the compound is present in at least one layer of the device, selected from holeinjection layer, hole-transporting layer, electron-blocking layer, and emitting layer, preferably selected from electron-blocking layer.

15. Organic electroluminescent device according to Claim 14, characterized in that30 the compound is present in a hole-transporting layer, which in addition to the compound comprises at least one further hole transporting compound.Foreignfiling text P24-253-SEC-WO01 20251217- 99 -16. Organic electroluminescent device according to Claim 14, characterized in that the compound is present in a layer selected from hole-injection layer and holetransporting layer, which layer comprises in addition to the compound, one or more further compounds which are selected from electron-transporting5 compounds and compounds having a wide band gap.

17. Organic electroluminescent device according to Claim 14, characterized in that it comprises two electron-blocking layers, and the compound is present in one of the two electron-blocking layers, which electron-blocking layer is adjacent to the emitting layer, which emitting layer is preferably a green phosphorescent emitting layer.

18. Use of a compound according to one or more of Claims 1 to 10 in an organic electroluminescent device.30

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