Materials for electronic devices

Abstract

The present invention relates to materials that are suitable for use in electronic devices, and to electronic devices, particularly organic electroluminescent devices (OLEDs), containing these materials. The materials are OLED materials.

Description

[0001] Materials for electronic devices

[0002] The present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these materials.

[0003] Electronic devices containing organic, organometallic, and / or polymeric semiconductors are becoming increasingly important. Due to their cost and performance, these semiconductors are used in many commercial products. Examples include organic charge transport materials (e.g., triarylamine-based hole transporters) in copiers, organic light-emitting diodes (OLEDs) in display devices, and organic photoreceptors in copiers. Organic solar cells (O-SC), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic switching elements (O-ICs), organic optical amplifiers, and organic laser diodes (O-lasers) are at an advanced stage of development and have the potential to become highly important in the future.

[0004] Electronic devices within the meaning of this invention are understood to be organic electronic devices that contain organic semiconductor materials as functional materials. In particular, these electronic devices are electroluminescent devices such as OLEDs.

[0005] The structure of OLEDs, which use organic compounds as functional materials, is known to those skilled in the art. Generally, OLEDs are electronic devices that have one or more layers comprising organic compounds and emit light when a voltage is applied.

[0006] In electronic devices, especially OLEDs, there is a great need to improve performance, particularly lifetime, efficiency, and operating voltage. No satisfactory solution has yet been found for these aspects.

[0007] Electronic devices typically comprise a cathode, an anode, and at least one functional, preferably emissive, layer. In addition to these layers, they may contain further layers, for example, one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers, and / or charge-generation layers.

[0008] The object of the present invention is to provide compounds which are suitable for use in an electronic device, in particular an OLED, in particular as material for electron-transport layers and / or as host materials, and which lead to good properties there. A further object of the present invention is to provide materials for hole-blocking layers. A hole-blocking layer is understood to be a layer arranged between the emitting layer and the electron-transport layer and which reduces the passage of holes. In particular, due to their sufficiently high T1 value and matching HOMO / LUMO levels, compounds according to the present application are outstandingly suitable for use in a hole-blocking layer.

[0009] A further object of the present invention is to provide compounds that effectively form exciplexes in combination with suitable hole-transporting materials. At the same time, the HOMO / LUMO levels of the compounds serving as electron-transporting host materials should be tunable with those of a hole-transporting host material and potential emitter or sensitizer compounds, whereby the compounds should have a suitable T1 level for this purpose.

[0010] Compounds of the present application are particularly suitable as electron-transporting host materials in both phosphorescent and hyperphosphorescent components, as well as in hyperfluorescent components and components containing a TADF emitter (TADF = thermally activated delayed fluorescence). Due to the above-mentioned properties, they exhibit advantages in these components. Use as one of three or four different components in the emitting layer is preferred, especially in components with hyperphosphorescent, hyperfluorescent, or TADF-based emitting layers.

[0011] Furthermore, the compounds according to the invention should not form undesirable exciplexes with emitter or sensitizer compounds in the emission layer.

[0012] Surprisingly, it has been found that certain nitrogen-containing compounds, described in more detail below, solve this problem and are well suited for use in electronic devices, particularly OLEDs. These OLEDs exhibit, in particular, a long lifetime, high efficiency, and low operating voltage. These compounds and electronic devices, particularly organic electroluminescent devices, containing these compounds are therefore the subject of the present invention.

[0013] The present invention relates to a compound according to formula (1),

[0014] Formula (1) where Z represents a group selected from structures of formulas (Z-1) to (Z-4)

[0015] Formula (Z-3) Formula (Z-4) where the dashed bond represents the bond to the nitrogen-containing heteroaryl group and the symbols continue to apply:

[0016] W is C, Si or Ge, preferably C or Si and particularly preferably C;

[0017] Y is chosen from C(R C )2, Si(R c )2, Ge(R c )2, 0 or S, preferably C(R C )2, Si(R c )2 or 0, particularly preferably C(R C )2;

[0018] L is a bond or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each substituted by one or more radicals R d can be substituted differently from H;

[0019] X a is the same or different at each occurrence N or CR a , where at least one group X a represents N, preferably at least two of the groups X a represent N and particularly preferably all groups X a stand for N; X b is the same or different at each occurrence N or CR b , where at most two of the groups Xb per ring represent N, preferably at most one of the groups X b per ring represents N and particularly preferably all groups X b for CR b stand;

[0020] X c is the same or different at each occurrence N or CR C , where at most two of the groups X c per ring represent N, preferably at most one of the groups X c per ring represents N and particularly preferably all groups X c for CR C stand;

[0021] R, R a , R b , R c , R d is the same or different at each occurrence H, D, F, CI, Br, I, OAr', SAr', N(R 1 )2, N(Ar')2, B(OR 1 )2, B(R 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , C(R 1 )3, Si(R 1 )3, Ge(R 1 )3, NO2, P(=O)(R 1 )2, P(Ar')2, P(R 1 )2, OSO2R1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 1 may be substituted differently from H, where one or more non-adjacent CH2 groups are substituted by - R 1 C=CR 1 -, -C C-, Si(R 1 )2, CONR 1 , NR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted differently from H, two residues can be selected from residues R a , R b , R cand R d also form a ring with each other;

[0022] Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is substituted by one or more radicals R 1 may be substituted differently from H, where two or more Ar' may form a ring with each other; R 1 is the same or different at each occurrence H, D, F, CI, Br, I, N(R 2 )2, B(OR 2 )2, B(R 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2 )2, CN, C(=O)OR 2 , C(R 2 )3, Si(R 2 )3, Ge(R 2 )3, NO2, P(=O)(R 2 )2, P(R 2 )2, OSO2R 2 , SR 2 , S(=O)R 2 , S(=O)2R 2, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 2 may be substituted differently from H and wherein one or more CH2 groups in the above-mentioned groups are substituted by -R 2 C=CR 2 -, -C=C-, Si(R 2 )2, NR 2 , C=O, C=S, -C(=O)O-, CONR 2 , P(=O)(R 2 ), -S-, SO or SO2 and where one or more H atoms in the above-mentioned groups can be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted differently from H, where two or more radicals R 1 can form a ring with each other;

[0023] R 2 is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more substituents R 2 be linked together to form a ring; whereby the radical R does not form a ring with the group L.

[0024] An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 5 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.

[0025] An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms, preferably 6 to 40 C atoms in the ring system. An aromatic ring system within the meaning of this invention does not contain a heteroaryl group. A heteroaromatic ring system within the meaning of this invention contains 1 to 60 C atoms, preferably 1 to 40 C atoms and at least one heteroaryl group, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is to be understood as a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be linked by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C, N or O atom or carbonyl group.Likewise, this includes systems in which two or more aryl or heteroaryl groups are directly linked to one another, such as, for example, biphenyl, terphenyl, bipyridine, or phenylpyridine. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are also to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a linear or cyclic alkyl group or by a silyl group. Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups, as well as groups in which two or more aryl or heteroaryl groups are directly linked to one another, for example, biphenyl, terphenyl, quaterphenyl, or bipyridine, as well as fluorene or spirobifluorene.

[0026] In the context of the present invention, the term "alkyl group" is used as a generic term for both linear or branched alkyl groups and cyclic alkyl groups. Analogously, the terms "alkenyl group" and "alkynyl group" are used as generic terms for both linear or branched alkenyl or alkynyl groups, as well as for cyclic alkenyl or alkynyl groups.

[0027] A cyclic alkyl, alkoxy or thioalkoxy group within the meaning of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.

[0028] In the context of the present invention, an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 40 C atoms and in which individual H atoms or CH2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclo-hexyl, n-octyl, cyclooctyl, 2-ethylhexyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-Dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1 , 1 -dimethyl-n-hex-1 -yl, 1 , 1 -dimethyl-n-hept-1 -yl, 1 , 1 -dimethyl-n-oct-1 -yl, 1 , 1 -dimethyl-n-dec-1 -yl, 1 , 1-Dimethyl-n-dodec-1-yl,1 , 1 -Dimethyl-n-tetradec-1 -yl, 1 , 1 -Dimethyl-n- hexadec-1 -yl, 1 ,1 -Dimethyl-n-octadec-1 -yl, 1 , 1 -Diethyl-n-hex-1 -yl, 1 ,1 - Diethyl-n-hept-1 -yl, 1 , 1 -Diethyl-n-oct-1 -yl, 1 , 1 -Diethyl-n-dec-1 -yl, 1 ,1 - Diethyl-n-dodec-1 -yl, 1 , 1 -Diethyl-n-tetradec-1 -yl, 1 , 1 -Diethyl-n-hexadec-1 - yl, 1 ,1 -Diethyl-n-octadec-1 -yl, 1 -(n-Propyl)-cyclohex-1 -yl, l -(n-Butyl)- cyclohex-1 -yl, 1 -(n-Hexyl)-cyclohex-1 -yl, 1 -(n-Octyl)-cyclohex-l -yl und 1 - (n-Decyl)-cyclohex-l -yl, Ethenyl, Propenyl, Butenyl, Pentenyl, Cyclo- pentenyl, Hexenyl, Cyclohexenyl, Heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Cyclooctadienyl, Ethinyl, Propinyl, Butinyl, Pentinyl, Hexinyl, Heptinyl oder Octinyl verstanden. Unter einer Alkoxygruppe OR, 1mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cyclo- heptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2, 2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe SR 1mit 1 bis 40 C-Atomen werden insbesondere Methylthio, Ethylthio, n-Propyl- thio, i-Propylthio, n-Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n-Pentyl- thio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptyl- thio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluormethylthio, Pentafluorethylthio, 2,2,2-Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenyl- thio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio verstanden.In general, alkyl, alkoxy, or thioalkyl groups according to the present invention may be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH2 groups may be replaced by the above-mentioned groups; furthermore, one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, preferably D, F, Cl, or CN, particularly preferably D, F, or CN.

[0029] An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, preferably 5 - 40 aromatic ring atoms, which may also be substituted by the above-mentioned radicals or a hydrocarbon radical and which may be linked to the aromatic or heteroaromatic ring via any desired positions, is understood to mean, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, Truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole,Indol, Isoindol, Carba- zol, Pyridin, Chinolin, Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chino- lin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Benzimidazolobenzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1 ,2-Thiazol, 1 ,3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1 ,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1 ,6-Diazapyren, 1 ,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetra- azaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1 ,2,3-Triazol, 1 ,2,4-Triazol, Benzotriazol, 1 ,2,3-Oxadiazol, 1 ,2,4-Oxadiazol, 1 ,2,5-Oxa- diazol, 1 ,3,4-Oxadiazol, 1 ,2,3-Thiadiazol, 1 ,2,4-Thiadiazol, 1 ,2,5-Thiadi- azol, 1 ,3,4-Thiadiazol, 1 ,3,5-Triazin, 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, or groups derived from combinations of these systems. These groups can also be deuterated. The phrase "two or more residues can form a ring" is understood, for the purposes of this description, to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme:

[0030] In education

[0031] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme: Preferably, it can be provided that Z represents a group selected from structures of the formulas (Z-5) to (Z-8),

[0032] Formula (Z-7) Formula (Z-8) where the dashed bond represents the bond to the nitrogen-containing heteroaryl group and R c has the meaning given above, in particular for formula (1).

[0033] In a preferred embodiment, the compound according to the invention corresponds to the following formula (2):

[0034] Formula (2) where the symbols Z, R, R a , W, X a and X b , which have the meanings set out above, in particular for formula (1) and formulas (Z-5) to (Z-8), and the following applies to the other symbols: g is an integer in the range from 0 to 5, where g = 0 means that the group L ais not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the associated atom, for example a carbon atom, preferably g is 0, 1, 2 or 3, particularly preferably 0, 1 or 2 and most particularly preferably 1; and

[0035] L a is a group chosen from structures of the formulas (L a -1 ) to (L a -5)

[0036] Formula (L a -4) Formula (L a -5) where the dashed bonds represent the attachment points and the other symbols are:

[0037] X d is the same or different at each occurrence N, CR d or, in the event that at this point the group L a binds to another group, C, preferably CR d or C, preferably with a maximum of 3 groups X dper ring represent N, particularly preferably at most 2 and very particularly preferably all groups X d for CR d or C;

[0038] Y a is chosen from C(R d )2, 0 or S, preferably C(R d )2 or 0, particularly preferably 0; where R d has the meaning given in claim 1, wherein R d has the meaning given above, in particular for formula (1). Preferably, for example, for structures of formula (2), the group L a is chosen from structures of the formulas (L a -6) to (L a -15)

[0039] Formula (L a -13) Formula (L a -14) Formula (L a -15) where the dashed bonds represent the attachment points, R d has the meaning given above, in particular for formula (1 ) and the following applies to the other symbols:

[0040] X dis the same or different at each occurrence N, CR d or, in the event that at this point the group L a binds to another group, C, preferably CR d or C; i is 1 or 2; and j is 0, 1 or 2.

[0041] Particularly preferably, for example, for structures of formula (2) it can be provided that the group L a is selected from structures of

[0042] Formulas (L a -16) to (L a -21 ) where the dashed bonds represent the attachment points and R d has the meaning given above, in particular for formula (1 ). Structures of the formula (L a -16) is particularly preferred over other structures.

[0043] In a particularly preferred embodiment, the compound according to the invention corresponds to one of the following formulas (3-1), (3-2) or (3-3):

[0044] Formula (3-3) where the symbols Z, R, R a , R b , W and X a which have the meanings set out above, in particular for formula (1) and formulas (Z-5) to (Z-8), the symbol L a which were previously used, especially for formula (2) and formulas (L a -6) to (L a -21 ), preferably those defined above, in particular for formulas (L a -6) to (L a -21 ) and particularly preferably those described above, especially for formulas (L a -16) to (L a -21 ) and the index g has the meaning set out above, in particular for formula (2). Compounds according to formula (3-1 ) or (3-2) are preferred, and compounds according to formula (3-1 ) are particularly preferred. In the case that X a = N, the formulas (3-1 ), (3-2) and (3-3) are identical. Compounds according to formula (3-1 ), (3-2) and (3-3) respectively, where X a = N are particularly preferred.

[0045] In a further particularly preferred embodiment, the compound according to the invention corresponds to the following formula (4):

[0046] Formula (4) where the symbols R 1 , R, R b , and R c have the meanings set out above, in particular for formula (1 ), the symbol L a which were previously used, especially for formula (2) and formulas (L a -6) to (L a -21 ), preferably those defined above, in particular for formulas (L a -6) to (L a -21 ) and particularly preferably those described above, especially for formulas (L a -16) to (L a -21 ) and the index g has the meaning explained above, in particular for formula (2).

[0047] In a preferred embodiment, R is selected from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1may be substituted, but is preferably unsubstituted. Furthermore, R is preferably selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthalene, dibenzofuran, dibenzothiophene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, phenanthrene or triphenylene, where these groups are each substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted or substituted by D. Particularly preferably, R is selected from phenyl, biphenyl or terphenyl, quaterphenyl, where these groups are each substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted. Most preferably, R is a phenyl radical which is substituted by one or more radicals R 1 may be substituted, but is preferably unsubstituted or substituted by D.

[0048] In a preferred embodiment, at least one radical R aselected from an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted, but is preferably unsubstituted. Furthermore, at least one radical R a selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, benzimidazolobenzimidazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, wherein these groups are each substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted. Particularly preferably, at least one radical R aselected from phenyl, biphenyl, terphenyl, quaterphenyl, carbazole, benzimidazolobenzimidazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, phenanthrene or triphenylene, wherein these groups are each substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted or substituted by D. Most preferably, R is selected from phenyl, biphenyl, carbazole or benzimidazolo-benzimidazole, where these groups are each substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted or substituted by D. It can be provided that the at least one radical R a which is selected from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably adjacent to a nitrogen atom of the pyridine, pyrimidine or triazine residue.

[0049] Furthermore, it can be provided that R and at least one radical Ra is selected, identically or differently at each occurrence, from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted, wherein the at least one radical R a is preferably adjacent to a nitrogen atom of the pyridine, pyrimidine or triazine residue.

[0050] In the context of the present invention, the term

[0051] Substituent in particular that the radicals R, R a , R b , R c , R d , R 1 are not equal to H. Furthermore, the substituents R, R a , R b , R c , R d , R 1 etc. may be the same or different if two or more substituents are present.

[0052] In a preferred embodiment of the invention, the groups R, R a , R b , R c , R dno substituted or unsubstituted amino groups. Preferably, the group R, R a , R b , R c , R d therefore no triarylamino groups, but can contain, for example, carbazole groups, i.e. heteroaryl groups that contain nitrogen.

[0053] When the compound according to the invention is substituted with aromatic or heteroaromatic groups R, R a , R b , R c , R d , R 1 or R 2is substituted, it is preferred in one embodiment if these do not contain any aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferably, the substituents do not contain any aryl or heteroaryl groups with directly fused aromatic six-membered rings. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless also suitable according to the invention are phenanthrene and triphenylene, since these also have a high triplet level.

[0054] In a preferred embodiment, R, R a , R b , R c , R d and the associated groups are not an aromatic or heteroaromatic ring system which has three linearly condensed aromatic 6 rings, wherein preferably none of the radicals R, R a , Rb , R c , R d an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-membered rings. Particularly preferably, R, R a , R b , R c , R d and the corresponding groups do not contain condensed aryl groups.

[0055] If two residues, which can be selected in particular from R a , R b , R c , R d , R 1 and / or R 2 , form a ring with each other, this ring can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic, or heteroaromatic. The radicals forming a ring can be adjacent, meaning that these radicals are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or they can be further apart.

[0056] Furthermore, the residues R a , R b , Rc , R d , R 1 and / or R 2 the respective groups to which these residues are bonded may optionally represent a bond, so that the associated groups, preferably rings or ring systems, can be directly connected to one another, so that a ring closure can be effected.

[0057] The residue R does not form a ring with the group L, although this also includes the formation of a ring via the respective groups R 1 or R d excludes.

[0058] In a preferred embodiment, the substituents R a with the radical R or the respective associated groups does not form a ring. Furthermore, it can be provided that the substituents R a with the residues R b , R c , R d or the respective associated groups do not form a ring. Furthermore, it can be provided that the radical R with the radicals R b , R c , R dor the respective associated groups does not form a ring. Furthermore, it can be provided that the group L or its substituents R d with the residues R a , R b , R c or the respective associated groups do not form a ring.

[0059] Furthermore, it can be provided that the residues or substituents R a , R b , R c , R d and R 1 according to the above formulas, with the ring atoms of the respective ring or ring system to which the radicals are bonded, do not form a fused aromatic or heteroaromatic ring system, preferably not a fused ring system. This embodiment, in which the radicals are substituents R a , R b , R c , R d and R 1 do not form a ring, the formation of a condensed ring system with possible substituents R 1 and R 2 also, which are attached to the residues R a , R b , R c, R d , R 1 may be bound.

[0060] In a further preferred embodiment of the invention, it can be provided that at most four of the groups R b , R c , R d are not equal to H or D, preferably at most two of the groups R b , R c , R d are not equal to H or D. In a particularly preferred

[0061] Embodiment is none of the groups R b , R c , R d not equal to H or D.

[0062] Preferred substituents R b , R c and R d , Ar', R 1 and R 2 In a particularly preferred embodiment of the invention, the following preferences for R b , R c , R d , Ar', R 1 and R 2simultaneously and apply to the structures of formula (1 ) as well as to all preferred embodiments listed above.

[0063] In a preferred embodiment of the invention, R b , R c and R d at each occurrence, the same or different, selected from the group consisting of H, D, F, CN, OR 1 , a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein the alkyl group is in each case substituted with one or more radicals R 1 may be substituted, but is preferably unsubstituted, and wherein one or more non-adjacent CH2 groups may be replaced by O, and an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which is substituted by one or more radicals R 1may be substituted. Particularly preferably, R is selected at each occurrence, identically or differently, from the group consisting of H, F, CN, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is substituted in each case with one or more radicals R 1 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 , preferably non-aromatic residues R 1 , may be substituted. Very particularly preferably, R is selected at each occurrence, identically or differently, from the group consisting of H, D, CN or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 , preferably non-aromatic residues R1 , may be substituted. Particularly preferably, all radicals R are the same or different on each occurrence and are selected from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R 1 , preferably non-aromatic residues R 1 can be substituted.

[0064] Suitable aromatic or heteroaromatic ring systems R, R a , R b , R c and R dare selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, which may be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, Pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups, each of which is substituted by one or more radicals R 1can be substituted. If R, R a R b , R c or R d represents a heteroaryl group, in particular triazine, pyrimidine or quinazoline, aromatic or heteroaromatic radicals R 1 at this heteroaryl group may be preferred.

[0065] The groups R, R a , R b , R c and / or R d if they represent an aromatic or heteroaromatic ring system, preferably selected from the groups of the following formulas R-1 to R-185,

[0066]

[0067] R-16 R-17 R-18

[0068] R-114 R-115 R-116 R-117 -

[0069]

[0070] 35 where R 1has the meanings given above, the dashed bond represents the bond to the corresponding group and furthermore:

[0071] Ar 3 is at each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which is substituted by one or more radicals R 1 can be substituted;

[0072] A 1 is the same or different each time it occurs BR 1 , C(R 1 )2, Si(R 1 )2, C=O, NR 1 , 0 or S, where A 1 in the formulas R-150 and R-151 for BR 1 , C=O, NR 1 , 0 or S;

[0073] A 2 is the same or different at each occurrence C(R 1 )2, NR 1 , 0 or S; p is 0 or 1 , where p = 0 means that the group Ar 3is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the associated atom, for example a carbon atom or to a heteroatom such as a nitrogen, where, in the case of bonding to a heteroatom, for the formulas R-44, R-49, R-53, R-57, R-58, R-62, R-66, R-70, R-71, R-112, R-152 to R-160, R-167, R-172, R-177, R-182 p is 1; r is 0 or 1, where r = 0 means that no group A is present at this position. 1 and the corresponding carbon atoms are instead bound to residues R 1 are bound.

[0074] In a preferred embodiment, Ar comprises 3 bivalent aromatic or heteroaromatic ring systems based on the groups R-1 to R-185, where p is 0 and the dashed bond and an R 1 represents the bond to the aromatic or heteroaromatic group according to R-1 to R-185.

[0075] If the above mentioned groups R-1 to R-185 for R several groups A 1 all combinations from the definition of A 1 Preferred embodiments are then those in which a group A 1 for C(R 1 )2, NR 1 , 0 or S and the other group A 1 for C(R 1 )2, NR 1 , 0 or S.

[0076] If A 1 for NR 1 the substituent R 1 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 In a particularly preferred embodiment, this substituent R 1identically or differently on each occurrence represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, and which in each case can also be substituted by one or more radicals R 2 Particularly preferred are phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35, where these structures are substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted.

[0077] If A 1 for C(R 1 )2, the substituents R 1which are bonded to this carbon atom, preferably identically or differently on each occurrence, represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 R is particularly preferably 1 represents a methyl group or a phenyl group. The radicals R 1 also form a ring system with each other, which leads to a spiro system.

[0078] In a further preferred embodiment of the invention, Ar' is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, particularly preferably having 6 to 24 aromatic ring atoms and very particularly preferably having 6 to 13 aromatic ring atoms, which is in each case substituted by one or more radicals R 1 can be substituted.

[0079] In a further preferred embodiment of the invention, R 1 identically or differently on each occurrence selected from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2 may be substituted, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each substituted by one or more radicals R 2may be substituted; two or more radicals R 1 together form an aliphatic ring system. In a particularly preferred embodiment of the invention, R 1 identically or differently on each occurrence selected from the group consisting of H, D, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is substituted with one or more radicals R 2 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 2 can be substituted.

[0080] In a further preferred embodiment of the invention, R 2identically or differently on each occurrence, H, D, CN, F, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted. In a further preferred embodiment of the invention, all radicals R 1 , insofar as they represent an aromatic or heteroaromatic ring system, or R 2 as long as they represent aromatic or heteroaromatic groups selected from the groups R-1 to R-185, which, however, are then each substituted with R 2 , or the one at R 2 mentioned groups are substituted.

[0081] In a preferred embodiment of the invention, all aromatic or heteroaromatic groups of the radicals R, R a , R b , R c , R d , R 1 or R 2 selected from the corresponding groups R-1 to R-185.

[0082] In a further preferred embodiment, it can be provided that at least one of the radicals R, R a , preferably the radical R and at least one radical R a represents an aromatic or heteroaromatic ring system selected from groups R-1 to R-185.

[0083] In a further preferred embodiment of the invention, the radical R is selected from the groups R-1 or R-45 to R-48, preferably the group R-1, where the radical A 1 in formulas R-45 to R-48 is preferably selected from 0 or S.

[0084] In a further preferred embodiment of the invention, at least one of the radicals R a selected from the groups R-1, R-44 to R-48 or R-158, preferably R-44 or R-158, particularly preferably R-44, wherein the radical A 1 in formulas R-45 to R-48 is preferably selected from 0 or NR 1 and in formulas R-44 or R-158 the index p is preferably 0.

[0085] In a preferred embodiment, the compounds are at least 50%, especially at least 80%, and most preferably completely (100%) deuterated. This means that in such a compound, the corresponding proportion of the hydrogen atoms contained in the undeuterated compound have been exchanged for D. The undeuterated compound is the corresponding compound in which the deuterium atoms have been exchanged for hydrogen and therefore contains no D. In a fully deuterated compound, all H atoms are exchanged for D.

[0086] According to a preferred embodiment, part of the compound is completely undeuterated, and another part is largely or completely deuterated. According to a preferred embodiment, the group Z or the group Z and the group R abe largely or completely deuterated, and the other parts of the compound of formula (1) are completely undeuterated. According to an alternative preferred embodiment of the invention, the group Z or the group Z and the group R a completely undeuterated, and the rest of the compound of formula (1 ) is largely or completely deuterated.

[0087] The alkyl groups in compounds according to the invention that are processed by vacuum evaporation preferably have no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds that are processed from solution, compounds substituted by alkyl groups, especially branched alkyl groups, with up to 10 carbon atoms, or substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups, are also suitable.

[0088] In a preferred embodiment, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L stands for phenylene, preferably ortho-linked phenylene, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole.

[0089] In a further embodiment, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L stands for biphenylene or dibenzofuran, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole. Preferably, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L represents a bond, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R ais selected from carbazole or phenyl, preferably carbazole.

[0090] In a preferred embodiment, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L stands for phenylene, preferably ortho-linked phenylene, the group Z corresponds to the formula (Z-4) or (Z-8), preferably (Z-8) and the radical R a is selected from carbazole or naphthocarbazole, preferably naphtho[1,2,3,4-def]carbazole.

[0091] In a preferred embodiment, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L stands for phenylene, preferably ortho-linked phenylene, the group Z corresponds to the formula (Z-3) or (Z-7), preferably (Z-7), where the group Y in formula (Z-3) is preferably selected from C(R C )2, Si(R c )2, and the remainder R a is selected from carbazole or phenyl, preferably carbazole.

[0092] Preferably, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the groups L represents a bond, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from fluorene or dibenzofuran, preferably dibenzofuran.

[0093] Furthermore, it can be provided that in formula (1) the radical W stands for C, the group R stands for phenyl, the group L stands for phenylene, preferably ortho-linked phenylene, the group Z corresponds to the formula (Z-2) or (Z-6), preferably (Z-6) and the radical R a is selected from carbazole or benzimidazolo-benzimidazole, preferably benzimidazolo-benzimidazole.

[0094] In a further preferred embodiment, it can be provided that in formula (1) the radical W stands for C, the group R stands for dibenzofuran, the groups L stands for fluorene, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole.

[0095] In these embodiments, preferably at least two, particularly preferably all, groups X a equal to N, where at most two of the groups X b , X c for N and preferably all groups X b , X c for CR b or CR C where a maximum of four of the groups R b , R c , R d not equal to H or D, preferably at most two of the groups R b , R c , R d not equal to H or D and most preferably none of the groups R b , R c , R d not equal to H or D.

[0096] In a particularly preferred embodiment, it can be provided that in formula (3-1), (3-2) or (3-3), the radical W stands for C, the group R stands for phenyl, the index g = 1, the groups L a the formula (L a -1 ), (L a -6) or (L a -16), preferably (L a -6) or (L a -16), particularly preferred (L a -16), the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole.

[0097] In a further embodiment, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for phenyl, the index g = 1, the groups L a the formula (L a -2), (LM), (L a -5), (L a -9), (L a -10), (L a -12), (L a -15), or (L a -21 ), preferably (L a-9), (L a -12), (L a -15), or (L a -21 ), the group Z corresponds to the formula (Z-1 ) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole.

[0098] Preferably, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for phenyl, the index g = 0, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole.

[0099] In a preferred embodiment, it can be provided that in

[0100] Formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for phenyl, the index g = 1, the groups L a the formula (L a -1 ), (L a -6) or (L a -16), preferably (L a -6) or (L a -16), particularly preferred (L a- 16), the group Z corresponds to the formula (Z-4) or (Z-8), preferably (Z-8) and the radical R a is selected from carbazole or naphthocarbazole, preferably naphtho[1,2,3,4-def]carbazole.

[0101] In a preferred embodiment, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the index g = 1, the groups L a the formula (L a -1 ), (L a -6) or (L a -16), preferably (L a -6) or (L a -16), particularly preferred (L a -16), the group Z corresponds to the formula (Z-3) or (Z-7), preferably (Z-7), wherein the group Y in formula (Z-3) is preferably selected from C(R C )2, Si(R c )2, and the remainder R a is selected from carbazole or phenyl, preferably carbazole.

[0102] Preferably, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for phenyl, the index g = 0, the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from fluorene or dibenzofuran, preferably dibenzofuran.

[0103] Furthermore, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for phenyl, the index g = 1, the groups L a the formula (L a -1 ), (L a -6) or (L a -16), preferably (L a -6) or (L a -16), particularly preferred (L a -16), the group Z corresponds to the formula (Z-2) or (Z-6), preferably (Z-6) and the radical R a is selected from carbazole or benzimidazolo-benzimidazole, preferably benzimidazolo-benzimidazole.

[0104] In a further preferred embodiment, it can be provided that in formula (3-1), (3-2) or (3-3) the radical W stands for C, the group R stands for dibenzofuran, the index g = 1, the groups L a the formula (L a - 4), (L a -5), (L a -14) or (L a -15), preferably (L a -14) or (L a -15), particularly preferred

[0105] (L a -15), the group Z corresponds to the formula (Z-1) or (Z-5), preferably (Z-5) and the radical R a is selected from carbazole or phenyl, preferably carbazole. In these embodiments, the group X a preferably equal to N, where at most two of the groups X d for N and preferably all groups X d for CR d where a maximum of four of the groups R b , R c , R d not equal to H or D, preferably at most two of the groups R b , R c , R dnot equal to H or D and most preferably none of the groups R b , R c , R d not equal to H or D.

[0106] The above-mentioned preferred embodiments can be combined with each other as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0107] Examples of preferred compounds according to the embodiments listed above are the compounds listed in the following table.

[0108] The compounds according to the invention can be prepared by synthesis steps known to the person skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Heck reaction, Hartwig-Buchwald coupling, etc.

[0109] The pyridine, pyrimidine, or triazine compounds suitable as starting materials for this purpose are often commercially available or can be prepared by methods known from the literature. The same applies to the starting materials to be reacted with the pyridine, pyrimidine, or triazine compounds. Further information on the synthesis of the compounds according to the invention can be found in the synthesis examples.

[0110] Preferably, the compounds of the present invention can be obtained according to the following Scheme 1.

[0111] Scheme 1

[0112] The definitions of the symbols L, Z, R, R a , W, X a and X bcorrespond to those shown for formula (1). The groups RG1 and RG2 are each reactive groups, the selection of these groups depending on the coupling reaction. In a preferred variant, the reactive groups RG1 and RG2 are selected from Cl, Br, I, and boronic acid derivatives. Particularly preferably, RG1 = Cl, and RG2 is selected from Br and I in the case of Grignard, and RG2 is a boronic acid derivative in the case of Suzuki.

[0113] In Scheme 1 above, the group L can represent a bond, in which case the reactive group RG2 binds to the group W. In this case, the statements made previously regarding the groups RG1 and RG2 apply accordingly, with the same preferences applying here as well.

[0114] The above statements preferably refer to coupling reactions carried out according to the Suzuki and Grignard processes. In variations of this scheme, the compounds of the invention can also be synthesized via other cross-coupling reactions, for example, via Stille coupling, which reactions are known to those skilled in the art.

[0115] A further object of the present invention is therefore a process for preparing the compounds according to the invention, characterized by the following steps:

[0116] (A) Synthesis of a first subunit comprising a pyridine, pyrimidine, or triazine residue containing a reactive leaving group; (B) Introduction of a second subunit comprising an aromatic or heteroaromatic residue by a coupling reaction.

[0117] The group L shown in formula (1) can be part of the first or the second subunit, wherein in a preferred embodiment the group L is part of the second subunit in the event that L does not represent a bond.

[0118] Suitable coupling reactions have been outlined above. Grignard reactions and transition metal-catalyzed cross-coupling reactions, preferably (Pd)-catalyzed cross-coupling reactions, are particularly suitable. The leaving group of the first subunit, which comprises a pyridine, pyrimidine, or triazine residue, is preferably selected from Br, Cl, and I.

[0119] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, Decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene,Phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butylmethyl ether, triethylene glycol butylmethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyloctanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0120] The present invention therefore further provides a formulation, in particular a solution, dispersion or emulsion, comprising at least one compound according to the invention and at least one further compound. The further compound can, for example, be a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. The preparation of such solutions is known to the person skilled in the art and is described, for example, in WO 2002 / 072714, WO 2003 / 019694 and the literature cited therein. However, the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and / or a matrix material. This further compound can also be polymeric.

[0121] The compounds of the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device (OLED). Depending on the substitution, the compounds can be used in different functions and layers.

[0122] A further object of the present invention is therefore the use of a compound according to the invention in an electronic device.

[0123] A further subject of the present invention is an electronic device comprising at least one compound according to the invention.

[0124] The compounds according to the invention can be present, particularly when used, as a racemate or as a pure enantiomer. An electronic device within the meaning of the present invention is a device that contains at least one layer containing at least one organic compound. The component can also contain inorganic materials or layers composed entirely of inorganic materials.

[0125] The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic photodiodes (OPDs), organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic plasmon-emitting devices, but preferably organic electroluminescent devices (OLEDs).

[0126] The device is particularly preferably an organic electroluminescent device comprising a cathode, an anode, and at least one emitting layer, wherein at least one organic layer, which may be an emitting layer, electron-transport layer, hole-blocking layer, or another functional layer, comprises at least one compound according to the invention. The layer depends on the substitution of the compound.

[0127] In addition to these layers, the organic electroluminescent device may contain further layers, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers, and / or organic or inorganic p / n junctions. Interlayers, which, for example, have an exciton blocking function, may also be introduced between two emitting layers. It should be noted, however, that not all of these layers are necessarily present.

[0128] The organic electroluminescent device can contain one emitting layer or it can contain multiple emitting layers. If multiple emitting layers are present, these preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Particular preference is given to systems with three emitting layers, with the three layers exhibiting blue, green, and orange or red emission (the basic structure is described, for example, in WO 2005 / 011013). The organic electroluminescent device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.

[0129] The compound of formula (1) is preferably used in an organic electroluminescent device comprising one or more phosphorescent emitters. The compound of the invention according to the embodiments listed above can be used in different layers, depending on the precise structure.

[0130] The organic electroluminescent device may contain one emitting layer or it may contain multiple emitting layers, with at least one organic layer of the device containing at least one compound according to the invention. The compound according to the invention is preferably contained in an emitting layer of the device. Furthermore, the compound according to the invention may also be contained in an electron-transport layer and / or in a hole-blocking layer and / or in an exciton-blocking layer.

[0131] The term "phosphorescent compound" typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., a quintet state. Suitable phosphorescent compounds (= triplet emitters) are, in particular, compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80.Preferably, phosphorescent compounds are considered to be all luminescent complexes with transition metals or lanthanides, especially if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold, or europium, especially compounds containing indium, platinum, or copper. For the purposes of the present invention, all luminescent indium, platinum, or copper complexes are considered to be phosphorescent emitting compounds.

[0132] Examples of the emitters described above can be found in the applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001 , WO 2019 / 115423, WO 2019 / 158453, WO2015 / 171627 and US2019119312.In general, all phosphorescent complexes as used according to the prior art for phosphorescent OLEDs and as known to the person skilled in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step. It is also possible for the person skilled in the art to use further phosphorescent complexes in combination with the compounds of formula (1) in organic electroluminescent devices without inventive step. Since the compounds according to the invention can also have a high triplet energy, depending on the substitution, it is also possible, in particular, to use them as matrix material for blue-phosphorescent emitters. Further examples are listed in the table below.

[0133] According to the invention, it is also possible to use the compound of formula (1) in an electronic device containing one or more fluorescent emitting compounds.

[0134] In a preferred embodiment of the invention, the compounds of formula (1) are used as electron-transporting materials. In this case, the compounds are preferably contained in an electron-transport layer or a hole-blocking layer, or as electron-conducting or bipolar host material in an emitting layer. Use as electron-conducting or bipolar host material in an emitting layer is particularly preferred.

[0135] An electron transport layer within the meaning of the present application is a layer with an electron-transporting function between the cathode and the emitting layer.

[0136] In the context of the present application, electron injection layers and hole blocking layers are understood to mean specific embodiments of electron transport layers. In the case of a plurality of electron transport layers between the cathode and the emitting layer, an electron injection layer is an electron transport layer that is directly adjacent to the cathode or is separated from it only by a single coating of the cathode. In the case of several electron transport layers between the cathode and the emitting layer, a hole blocking layer is the electron transport layer that is directly adjacent to the emitting layer on the cathode side. The OLED according to the invention preferably comprises two, three or four electron-transporting layers between the cathode and the emitting layer, of which preferably at least one, particularly preferably exactly one or two, contains a compound of the formula (1).If the compound of formula (1) is used as an electron transport material in an electron transport layer, an electron injection layer or a hole blocking layer, the compound can be used as a pure material, ie in a proportion of 100% in the electron transport layer, or it can be used in combination with one or more other compounds.

[0137] In a further embodiment of the present invention, the compound of formula (1) is used in an emitting layer as a matrix material in combination with one or more emitting compounds, wherein the emitting compounds may be fluorescent or phosphorescent, preferably phosphorescent.

[0138] In this case, the proportion of matrix material in the emitting layer is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.

[0139] Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, particularly preferably between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers.

[0140] An emitting layer of an organic electroluminescent device can also comprise systems that contain 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 that have the smaller proportion in the system and the matrix materials those that have the larger proportion in the system. In individual cases, however, the proportion of an individual matrix material in the system can be lower than the proportion of an individual emitting compound. Preferably, the compounds of formula (1) are used as a component of mixed matrix systems. The mixed matrix systems preferably consist of two or three different matrix materials, particularly preferably of two different matrix materials.In this case, one of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties. The compound of formula (1) is preferably the matrix material with electron-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely combined in a single mixed matrix component, with the further mixed matrix component(s) fulfilling other functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices.A source for more detailed information on mixed matrix systems is the application WO 2010 / 108579.

[0141] The mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds. Mixed matrix systems are generally preferred for use in phosphorescent organic electroluminescent devices.

[0142] Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent compounds or the preferred matrix materials for fluorescent compounds mentioned below, depending on the type of emitting compound used in the mixed matrix system.

[0143] Preferred phosphorescent compounds for use in mixed matrix systems are the same as those described above as generally preferred phosphorescent emitter materials.

[0144] Examples of preferred phosphorescent emitters are the compounds listed in the table of WO 2023 / 025971 , pp. 100-104.

[0145] Preferred fluorescent emitting compounds are selected from DABNA derivatives and other boron derivatives, in particular according to WO 2020 / 208051, WO 2015102118, WO 2016 / 152418, WO 2018 / 095397, WO 2019 / 004248, WO 2019 / 132040, US 2020 / 0161552, and WO 2021 / 089450. Particularly preferred fluorescent emitters are the compounds shown in the following table:

[0146] Useful matrix materials for fluorescent compounds in the emitting layer, particularly in the case where the compounds according to the present application are not used in the emitting layer, include materials from various substance classes. Preferred matrix materials are then selected from the classes of oligoaryls (e.g., 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoaryls with fused aromatic groups, oligoarylenevinylenes (e.g., DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g., according to WO 2004 / 081017), hole-conducting compounds (e.g., according to WO 2004 / 058911), electron-conducting compounds, especially ketones, phosphine oxides, sulfoxides, etc.(for example, according to WO 2005 / 084081 and WO 2005 / 084082), the atropisomers (for example, according to WO 2006 / 048268), the boronic acid derivatives (for example, according to WO 2006 / 117052), or the benzanthracenes (for example, according to WO 2008 / 145239). Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene, or 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 oligoarylenes containing anthracene, benzanthracene, benzophenanthrene, and / or pyrene, or atropisomers of these compounds. For the purposes of the present invention, an oligoarylene is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.Further preferred are the anthracene derivatives disclosed in WO 2006 / 097208, WO 2006 / 131192, WO 2007 / 065550, WO 2007 / 110129, WO 2007 / 065678, WO 2008 / 145239, WO 2009 / 100925, WO 2011 / 054442 and EP 1553154, the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012 / 0187826, the benzanthracenylanthracene compounds disclosed in WO 2015 / 158409, the indenobenzofurans disclosed in WO 2017 / 025165 and the pyrene compounds disclosed in WO 2017 / 036573 disclosed phenanthrylanthracenes.

[0147] Preferred matrix materials for phosphorescent compounds are, as well as compounds according to formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-biscarbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. B. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. B.according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781 , lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951 , or dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579.

[0148] Another possibility for improving the performance of electronic devices, particularly organic electroluminescent devices, is to use combinations of two or more host materials in the emission layer. For example, US Pat. No. 6,392,250 B1 discloses the use of a mixture consisting of an electron-transport material, a hole-transport material, and a fluorescent emitter in the emission layer of an OLED. US Pat. No. 6,803,720 B1 discloses the use of a mixture containing a phosphorescent emitter and a hole-transport and electron-transport material in the emission layer of an OLED.

[0149] Also preferred are material mixtures in the emitting layer which, in addition to the compound of formula (1) as host material, contain one, two, or three further compounds selected from host materials and emitter materials. The following compositions are particularly preferred in the emitting layer:

[0150] -compound of formula (1 ) as host, as well as another compound which is a triplet emitter;

[0151] -compound of formula (1 ) as host, further host compound, and further compound which is a triplet emitter;

[0152] Compound of formula (1 ) as host, further host compound, further compound which is a triplet emitter, and further compound which is a fluorescent emitter.

[0153] It is further preferred that the composition of the present invention, preferably present in an emitting layer of the electronic device, in addition to the electron-transporting material, which is preferably a compound according to formula (1), further contains at least one hole-transporting host material.

[0154] Preferably, the at least one hole-transporting host material is selected from the group of carbazole and triarylamine derivatives, more specifically biscarbazoles, bridged carbazoles, triarylamines, dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, carbazolamines, and compounds containing a silicon- and nitrogen-containing ring.

[0155] More preferably, the at least one hole-transporting host material is selected from compounds of formula (h-1) or (h-2):

[0156] Formula (h-1) Formula (h-2) where:

[0157] K Ar 4 or -L 5 -N(Ar)2;

[0158] Z A CR z or CR A or two adjacent groups Z together form a condensed ring;

[0159] R A -L 3 -Ar 5 or -L 4 -N(Ar)2;

[0160] R zis selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, N(Ar)2, N(R')2, OAr, SAr, CN, NO2, OR', SR', COOR', C(=O)N(R')2, Si(R')3, B(OR')2, C(=O)R', P(=O)(R')2, S(=O)R', S(=O)2R', OSO2R', a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R, where one or more non-adjacent CH2 groups are substituted by Si(R')2, C=O, NR', O, S or CONR', or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R';

[0161] L 4 , L 5at each occurrence, identically or differently, are a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R';

[0162] L 3 a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R', where a radical R' is attached to L 3 with a remainder R z at which carbazole can form a ring;

[0163] Ar 4 an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R';

[0164] Ar 5at each occurrence, identically or differently, is an unsubstituted or substituted heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more R';

[0165] R zat each occurrence, identically or differently, H, D, F, CI, Br, I, N(Ar)2, N(R')2, OAr, SAr, CN, NO2, OR', SR', COOR', C(=O)N(R')2, Si(R')3, B(OR')2, C(=O)R', P(=O)(R')2, S(=O)R', S(=O)2R', OSO2R', a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R', where one or more non-adjacent CH2 groups are substituted by Si(R')2, C=O, NR', O, S or CONR', or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R', where two radicals R z can together form a ring system;

[0166] E is at each occurrence independently a single bond or a group C(R°)2;

[0167] R° is independently selected at each occurrence from a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R' radicals; x, y are independently selected from 0 or 1, wherein when x or y is 0, the corresponding group E is not present; and x + y = 1 or 2;

[0168] Ar is, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms which may be substituted by one or more radicals R", where two or more R" may together form an aromatic or heteroaromatic ring system;

[0169] R' is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(Ar)2, N(R")2, OAr, SAr, CN, NO2, OR", SR", COOR", C(=O)N(R")2, Si(R")3, B(OR")2, C(=O)R", P(=O)(R")2, S(=O)R", S(=O)2R", OSO2R", a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R", where one or more non-adjacent CH2 groups may be replaced by Si(R")2, C=O, NR", O, S or CONR", or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R", where two radicals R' together may also form a ring system;

[0170] R" is, on each occurrence, identical or different, H, D, F, CI, Br, I, N(R"')2, CN, NO2, OR"', SR, COOR"', C(=O)N(R'")2, Si(R'")3, B(OR'")2, C(=O)R"', P(=O)(R"')2, S(=O)R"', S(=O)2R"', OSO2R'", a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R"', where one or more non-adjacent CH2 groups are substituted by Si(R"')2, C=O, NR"', O, S or CONR"', or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R"', where two radicals R" together may also form a ring system;

[0171] R"' is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more radicals R"' together may form a ring system. with the proviso that the compounds of the formulas (h-1) and (h-2) contain at least one group Z A include those for R A stands.

[0172] Preferably, L 4 , L 5 at each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system having 5 to 25, more preferably 5 to 20 and even more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R'.

[0173] Preferably, L 3a single bond or an aromatic or heteroaromatic ring system having 5 to 25 aromatic ring atoms, more preferably 5 to 20 and even more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R', where a radical R' is attached to L 3 with a remainder R z at which carbazole can form a ring.

[0174] Preferably, the group Ar 5 an unsubstituted or substituted heteroaromatic ring system selected from the groups of formulas (Ar5-1) to (Ar5-6), where the dashed bond represents the bond to L 3 or Z A indicates;

[0175] V CR v is, with the proviso that V is C when bonded to the group of formula (h-1 ) or (h-2); or two adjacent groups

[0176] V together form a condensed ring; T CR Tis, with the proviso that T represents C when bonded to the group of formula (h-1) or (h-2), or two adjacent groups T together form a condensed ring;

[0177] M is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R;

[0178] E 1 is independently at each occurrence a single bond or a group C(R°)2; where R° has the same meaning as above;

[0179] R T ' R vis selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, N(Ar)2, N(R')2, OAr, SAr, CN, NO2, OR', SR', COOR', C(=O)N(R')2, Si(R')3, B(OR')2, C(=O)R', P(=O)(R')2, S(=O)R', S(=O)2R', OSO2R', a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R', where one or more non-adjacent CH2 groups are substituted by Si(R')2, C=O, NR', O, S or CONR', or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R', where two radicals R T together can form a ring system and two residues R vtogether can form a ring system; x 1 , y 1 are independently selected from 0 or 1, where if x 1 or y 1 0, the corresponding group E 1 is not present; provided that x 1 + y 1 = 1 or 2; and wherein R' and Ar have the same meaning as above. According to a preferred embodiment, the at least one hole-transporting host material is selected from compounds of the formula (h-1-1) to (h-2-2):

[0180] Formula (h-1 -3)

[0181] Formula (h-2-2) where the symbols have the same meaning as above and where the indices have the following meaning: x, y, x 1 ,y 1 have the same meaning as above; c, f independently represent 0, 1, 2, 3 or 4; d, e independently represent 0, 1, 2 or 3; g represents 0, 1, 2 or 3 when x 1 =0; or for 0, 1 or 2 if x 1=1 ; h stands for 0, 1 , 2, 3 or 4 if y 1 =0; or for 0, 1 , 2 or 3, if y 1 =1 ; k stands for 0, 1 , 2, 3 or 4 if x=0; or for 0, 1 , 2 or 3 if x=1 ; and

[0182] I stands for 0, 1, 2, or 3 if y=0; or for 0, 1, or 2 if y=1.

[0183] Particularly preferably, the at least one hole-transporting host material is further selected from the compounds according to formula (H-1) and the preferred embodiments of this formula, according to the not yet published application PCT / EP2023 / 085990, see also below, from compounds of the above-mentioned formula (h-1 -3) and from compounds of the above-mentioned formula (h-1 -4).

[0184] Examples of preferred hole-transporting host materials suitable as the second host material in the composition are shown in the following table:

[0185]

[0186] 

[0187]

[0188]  In the table above, n represents the number of D atoms in the respective compound. If n = 0, this means that the compound is non-deuterated; n = 1 means that in the respective compound, one H atom is replaced by a D atom. nmax represents the maximum number of D atoms possible in the respective compound. The maximum number nmax can vary from compound to compound; depending on the compound, nmax can take on the following values: 20, 24, 26, 28, 30, 31, 32, 34, 35, 36, 37, 38, and 40.

[0189] According to an alternative preferred embodiment, the at least one hole-transporting host material is selected from compounds of formula (h-3): where the following applies to the groups and indices that occur:

[0190] M His selected from Si, Ge and Sn, where M H preferably Si;

[0191] A is a ring selected from mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems, each of which is substituted by one or more radicals R H can be substituted;

[0192] Y H stands, identically or differently on each occurrence, for a group selected from NR H-N2 , 0 and S, where Y H preferably NR H-N2 is;

[0193] RH-MI , RH-M2 Sin d is selected at each occurrence, the same or different, from H, D, F, CI, Br, I, C(=O)R H , OSO2R H , COOR H , CON(R H )2, N(R H )2, straight-chain alkyl groups having 1 to 40 C atoms, branched or cyclic alkyl groups having 3 to 40 C atoms, alkenyl or alkynyl groups having 2 to 40 C atoms, where the groups are each substituted by one or more radicals R Hmay be substituted, and wherein one or more CH2 units in the above-mentioned groups are substituted by Si(R H )2, Ge(R H )2, Sn(R H )2, C=O, C=S, C=Se, C=NR H , P(=O)(R H ), SO, SO2, NR H , -O-, -S-, -COO- or -CONR H - may be replaced, and wherein one or more H atoms in the above-mentioned groups may be replaced by D, F, CI, Br, I, CN or NO2, and aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is replaced by one or more radicals R H and aralkyl or heteroaralkyl groups having 5 to 60 aromatic ring atoms, each substituted by one or more radicals R H may be substituted, where R H ' M1 and R H - M2may be linked together and form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R H can be substituted;

[0194] RH-NI , RH-N2 Sin d at each occurrence, identically or differently, is selected from H, D, F, straight-chain alkyl groups having 1 to 40 C atoms, branched or cyclic alkyl groups having 3 to 40 C atoms, each of which is substituted by one or more radicals R H may be substituted, and in which one or more H atoms may be replaced by D, F or CN, and aromatic or heteroaromatic ring systems with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R H may be substituted; and where: when n=m=1 , the radicals R H ' N1 and R H ' M1 and / or R H - N2 and R H - M2linked together and form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, each of which is linked to one or more radicals R H may be substituted; or if n = 2, two radicals R H ' N1 and / or two residues R H - N2 if present, be linked to one another and form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, each of which is linked to one or more radicals R H can be substituted;

[0195] R H represents at each occurrence, identically or differently, H, D, F, CI, Br, I, CHO, CN, C(=O)Ar H , P(=O)(Ar H )2, S(=O)Ar H , S(=O)2Ar H , N(R H ')2, N(Ar H )2, NO2, Si(R H ')3, B(OR H ')2, OSO2R H', a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which is substituted by one or more radicals R H ' may be substituted, where one or more non-adjacent CH2 groups are substituted by R H 'C=CR H , C=C, Si(R H ')2, Ge(R H ')2, Sn(R H ')2, C=O, C=S, C=Se, P(=O)(R H ), SO, SO2, 0, S or CONR H and wherein one or more H atoms may be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R H ' may be substituted, or an aryloxy group having 5 to 60 aromatic ring atoms, each substituted by one or more radicals R H ' may be substituted; where two radicals R Hmay be linked together and form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R H ' can be substituted;

[0196] Ar H is selected at each occurrence, identically or differently, from aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R H ' may be substituted;

[0197] R H' is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more CH2 groups may be replaced by SO, SO2, O, or S, and where in each case one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms; n is 1 or 2; m is (2-n).

[0198] Furthermore, the disclosure of the as yet unpublished application PCT / EP2023 / 085990 regarding preferred embodiments of the compounds of the above-mentioned formula (h-3), in particular pages 10-21 of PCT / EP2023 / 085990, is hereby fully incorporated into the disclosure of the present application. Also preferred as hole-transporting host material, for use in combination with the compound according to the application, preferably in an emitting layer of the electronic device, are the compounds shown in the table on pages 22-28 of the as yet unpublished application PCT / EP2023 / 085990.

[0199] Preferably, the compound of formula (1) is used as host material in combination with a blue or green phosphorescent emitter, in particular with a blue phosphorescent emitter.

[0200] Furthermore, it is preferred that the at least one blue phosphorescent emitter is selected from platinum complexes.

[0201] Preferably, the at least one blue phosphorescent emitter has a LUMO of -1.8 eV to -2.2 eV, and the at least one blue phosphorescent emitter preferably has a HOMO of -5.0 eV to -5.6 eV, as defined by quantum mechanical calculations.

[0202] Preferably, the energy of the lowest triplet state Ti of the at least one blue phosphorescent emitter is higher than 2.55 eV, more preferably >2.65 eV, even more preferably >2.75 eV, as defined by quantum mechanical calculations.

[0203] Furthermore, it is preferred that the compound of formula (1) is used as the host material in a blue- or green-emitting layer. The layer is preferably a blue-phosphorescent or blue-hyperphosphorescent layer. Alternatively, it can also be a blue- or green-hyperfluorescent layer or a green-phosphorescent layer.

[0204] The compounds of formula (Pt-1 ) are very suitable as blue phosphorescent metal complexes according to the following definition:

[0205] Formula (Pt-1 ) where:

[0206] Y 1 Y 2 , Y 3 , Y 4 , Y 5 same or different at each occurrence for a group CR Y or N; or Y 1 -Y 2 and / or Y 3 -Y 4 or Y 4 -Y 5can form a condensed aryl or heteroaryl ring having 5 to 18 aromatic ring atoms, each of which can also be substituted by one or more radicals R';

[0207] E 50 at each occurrence, the same or different for C(R co )2, NR N0 , 0 or S;

[0208] Ar 50 at each occurrence, identically or differently, is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may also be substituted by one or more radicals R';

[0209] Ar 51 , Ar 52 , Ar 53 identical or different represent a condensed aryl or heteroaryl ring having 5 to 18 aromatic ring atoms, each of which may also be substituted by one or more radicals R';

[0210] R Yat each occurrence, identically or differently, represents a radical selected from H, D, F, CI, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R')2, N(Ar)2, NO2, Si(R')s, B(OR')2, OSO2R', a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R', where in each case one or more non-adjacent CH2 groups are substituted by R'C=CR', C^C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S or CONR' and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R', and an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R',where two radicals R, Y together may form an aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R';

[0211] R co at each occurrence, identically or differently, represents a radical selected from H, D, a straight-chain alkyl group having 1 to 40 C atoms, which may be substituted by one or more radicals R', an aryl or heteroaryl group having 6 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R, where two radicals R c together may form an aliphatic, aromatic or heteroaromatic ring system substituted by one or more radicals R';

[0212] R N0at each occurrence, identically or differently, represents a radical selected from H, D, F, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of which is substituted by one or more radicals R' and where one or more H atoms may be replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R';

[0213] R' and Ar have the same meaning as above.

[0214] Preferably, Ar 50 at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40, more preferably 5 to 30 and even more preferably 6 to 18 aromatic ring atoms, which may in each case also be substituted by one or more radicals R'.

[0215] Preferably, Ar 51 , Ar 52 , Ar53 identical or different for a condensed aryl or heteroaryl ring with 6 aromatic ring atoms, which may also be substituted by one or more radicals R'.

[0216] Preferably, R Yat each occurrence, identically or differently, represents H, D, F, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20 and more preferably 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20 and more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R', where one or more non-adjacent CH2 groups may be replaced by R'C=CR', C=C, O or S and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30 and particularly preferably 5 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R' can.

[0217] Preferably, R coat each occurrence, identically or differently, represents a radical selected from H, D, a straight-chain alkyl group having 1 to 10, preferably 1 to 6 and more preferably 1 to 3 C atoms, which may be substituted by one or more radicals R', an aryl or heteroaryl group having 6 to 18 and preferably 6 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R', where two radicals R co together may form an aliphatic, aromatic or heteroaromatic ring system substituted by one or more radicals R'.

[0218] Preferably, R N0at each occurrence, identically or differently, represents a radical selected from an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, and even more preferably 5 to 18 aromatic ring atoms, each of which may be substituted by one or more R' radicals. Examples of particularly suitable blue-phosphorescent metal complexes are shown below:

[0219]

[0220] 35

[0221] Suitable charge transport materials which can be used in the hole injection or hole transport layer or in the electron barrier layer or in the electron transport layer of the electronic component according to the invention are, in addition to the compounds of formula (1), for example those described in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials which are used in these layers according to the prior art.

[0222] Any materials that are currently used as hole-transport materials in the hole-transport layer can be used as materials for the hole-transport layer. Aromatic amine compounds can be used. Further compounds which are preferably used in hole-transporting layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (e.g. according to WO 2006 / 122630 or WO 2006 / 100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (e.g. according to WO 01 / 049806), amine derivatives with fused aromatics (for example according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorenamines (for example according to WO 08 / 006449), dibenzoindenofluorenamines (for example according to WO 07 / 140847), spirobifluorenamines (for example according to WO 2012 / 034627 or WO 2013 / 120577), fluorenamines (for example according to WO 2014 / 015937, WO 2014 / 015938, WO 2014 / 015935 and WO 2015 / 082056),Spirodibenzopyranamines (for example according to WO 2013 / 083216), dihydroacridine derivatives (for example according to WO 2012 / 150001), spirodibenzofurans and spirodibenzothiophenes (for example according to WO 2015 / 022051, WO 2016 / 102048 and WO 2016 / 131521), phenanthrenediarylamines (for example according to WO 2015 / 131976), spirotribenzotropolones (for example according to WO 2016 / 087017), spirobifluorenes with meta-phenyldiamine groups (for example according to WO 2016 / 078738), spirobisacridines (for example according to WO 2015 / 158411), xanthenediarylamines (for example according to WO 2014 / 072017), and 9,10-dihydroanthracene spiro compounds with diarylamino groups according to WO 2015 / 086108.,

[0223] Very particular preference is given to the use of spirobifluorenes substituted by diarylamino groups in the 4-position as hole-transporting compounds, in particular the use of those compounds claimed and disclosed in WO 2013 / 120577, and the use of spirobifluorenes substituted by diarylamino groups in the 2-position as hole-transporting compounds, in particular the use of those compounds claimed and disclosed in WO 2012 / 034627.

[0224] The OLED according to the invention preferably comprises two or more different electron-transporting layers. The compound of formula (1) can be used in none, in one or more, or in all electron-transporting layers. In a preferred embodiment, the compound of formula (1) is used in exactly one or exactly two electron-transporting layers, and other compounds are used in the other electron-transporting layers present. Further compounds that can be used in addition to the compounds of formula (1) are all materials that are used according to the prior art as electron-transport materials in the electron-transport layer. Particularly suitable are aluminum complexes, e.g. Alq5, zirconium complexes, e.g. Zrq4, lithium complexes, e.g.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. Other suitable materials are derivatives of the aforementioned compounds, as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0225] The device is structured, contacted and finally sealed accordingly (depending on the application) to exclude harmful influences from water and air.

[0226] In the further layers of the organic electroluminescent device according to the invention, all materials can be used as they are commonly used according to the prior art. The person skilled in the art can therefore, without inventive step, use all materials known for organic electroluminescent devices in combination with the compounds according to the invention according to formula (1) or the preferred embodiments described above. Furthermore, an organic electroluminescent device is preferred, characterized in that one or more layers are coated using a sublimation process. In this process, the materials are coated in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10' 7 mbar.

[0227] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are sublimated at a pressure between 10' 5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured.

[0228] Also preferred is an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0229] Furthermore, hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.

[0230] These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices containing the compounds of the invention. According to the invention, the electronic devices containing one or more compounds of formula (1) can be used in displays, as light sources in lighting applications, and as light sources in medical and / or cosmetic applications (e.g., light therapy).

[0231] The compounds according to the invention and the organic electroluminescent devices according to the invention are characterized by one or more of the following properties:

[0232] 1 . The compounds according to the invention lead to long lifetimes.

[0233] 2. The compounds according to the invention lead to high efficiencies, in particular to a high EQE.

[0234] 3. The compounds according to the invention result in low operating voltages.

[0235] 4. Electronic devices, in particular organic electroluminescent devices containing compounds according to the invention, in particular as matrix material, have a very high color purity.

[0236] The invention is further illustrated by the following examples, without intending to limit it. From these descriptions, one skilled in the art can practice the invention within the entire disclosed scope and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the method according to the invention.

[0237] Examples:

[0238] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased from Sigma-Aldrich or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds.

[0239] Synthesis examples

[0240] Comparative example 1 (CAS: 2728723-21-3): : 57 5 -75-4 CAS: 877615-05-9

[0241] 9-(3-bromophenyl)-9-phenyl-9H-fluorene (1257251-75-4) is commercially available. The synthesis of 9-[4-(9H-carbazol-9-yl)-6-chloro-1,3,5-triazin-2-yl]-9H-carbazole (877615-05-9) is described in Chem. Mater. 2013, 25(18), 3758-3765.

[0242] Dry magnesium turnings (2.94 g, 121 mmol) are placed in the flask and covered with tetrahydrofuran (THF). 1257251-75-4 (40.0 g, 101 mmol) is dissolved in THF (300 mL), and a small amount of the solution is slowly added dropwise to the magnesium turnings until the exothermic reaction begins. The remaining solution is then added dropwise while stirring until the magnesium turnings are almost completely dissolved. The Grignard solution is refluxed for 1 hour and then cooled to room temperature, then to 0 °C.

[0243] In a second flask, 877615-05-9 (47.6 g, 101 mmol) is placed and suspended in THF (200 ml). The suspension is cooled to -5 °C. At this temperature, the cooled Grignard solution is added dropwise via a transfer cannula. The reaction mixture is slowly warmed to room temperature and stirred for 2 hours. 1 molar hydrochloric acid (0.10 mol, 101 ml) is then slowly added dropwise. Toluene (300 ml) and saturated brine (100 ml) are added to the mixture. After phase separation, the organic phase is dried over sodium sulfate, and the solvent is removed using a rotary evaporator. The crude product (68 g) is recrystallized from toluene / heptane. The product is obtained as a white solid (45.4 g, 62.4 mmol, 62%).

[0244] Examples 2-8

[0245] The following products P2-P6 can be prepared using the indicated starting materials via the same synthesis route as Example 1 (Grignard reaction). Products P7-P8 can be prepared using the indicated starting materials analogously to the synthesis route of Comparative Example 1 (Suzuki reaction).

[0246] Synthesis of E A2:

[0247] 5H-Benzimidazo[1,2-a]benzimidazole (28890-99-5) and 2,4,6-trichloropyrimidine (3764-01-0) are commercially available.

[0248] 28890-99-5 (5.0 g, 24.1 mmol) is placed in a flask and suspended in THF (100 ml). The suspension is cooled to -78 °C. n-Butyllithium in hexane (2.5 M, 10.1 ml, 25.3 mmol) is slowly added dropwise, and the solution is stirred at this temperature for 15 min. The mixture is then warmed to -25 °C, and the cold bath is replaced with an ice bath to bring the temperature to 0 °C.

[0249] 3764-01-0 (1.4 ml, 12.1 mmol) is dissolved in THF (50 ml) and added dropwise to the reaction mixture. The mixture is stirred at 0 °C for 15 min and then heated to 60 °C for 12 hours. After cooling to room temperature, the mixture is poured into water, and the resulting solid is filtered off with suction and dried. The product is obtained as a white solid (4.9 g, 9.3 mmol, 39%).

[0250] Synthesis of E B7:

[0251] The boronic acid ester E B7 is prepared from the corresponding chloride (2668276-19-3) analogously to the procedure in WO20174838 A1.

[0252] Example: Production of OLEDs

[0253] The production of OLEDs has been described several times in the literature, e.g., in WO 2004 / 058911. The process is adapted to the conditions described below, i.e., layer thickness variations, layer sequences, and materials. Examples of OLED components according to preferred embodiments of the invention are described below.

[0254] All exemplary OLED components are characterized by the following layer structure:

[0255] - glass plate (hereinafter also glass substrate or substrate),

[0256] - Indium tin oxide (hereinafter ITO) as anode,

[0257] - Hole injection layer (hereinafter HIL)

[0258] - hole transport layer (hereinafter HTL),

[0259] - Electron blocking layer (hereinafter EBL),

[0260] - Emission layer (hereinafter EML),

[0261] - Hole blocking layer (hereinafter HBL),

[0262] - Electron transport layer (ETL),

[0263] - Electron injection layer (hereinafter EIL), - Aluminium (hereinafter cathode).

[0264] The glass substrates with the patterned 50 nm thick ITO are pretreated with an oxygen plasma followed by an argon plasma. The materials for the HIL, HTL, EBL, EML, HBL, ETL, and EIL are then applied to the pretreated glass substrate by thermal evaporation in a vacuum chamber. Detailed information on the HIL, HTL, EBL, EML, HBL, ETL, and EIL of the OLED devices is provided in Table 1. The materials used in these examples are listed in Table 3. The cathode consists of a 100 nm thick aluminum layer.

[0265] According to one embodiment of the invention, the EML comprises a hole-transporting host material, an electron-transporting host material, and a phosphorescent metal complex. All materials of the EML are deposited in parallel at a specific deposition rate, i.e., by co-evaporation, to form a homogeneous, amorphous mixture. The deposition rate of the individual materials can be selected so that each material is present in the mixture at a specific volume fraction (vol%). For example, the composition of an EML comprising a hole-transporting host material (HH) at 45 vol%, an electron-transporting host material (EH) at 45 vol%, and a phosphorescent metal complex (D) at 10 vol% is referred to in Table 1 as HH:EH:D (45%:45%:10%).This notation is analogous to describing the composition of an EML, which comprises two or four different materials, and also for HIL, HTL, EBL, HBL, ETL and EIL of the OLED device, if these layers each comprise more than one material.

[0266] The performance of OLED devices can be measured using standard methods. For this purpose, the electroluminescence (EL) spectra and the external quantum efficiency (EQE) can be determined from current / voltage / luminance (IUL) characteristics, assuming a Lambertian emission profile. The EL spectra can be measured at a luminance of 1000 cd / m 2 and the CIE 1931 x- and y-coordinates are calculated from the EL spectrum. The operating voltage U is defined as the voltage required for a current density of 10 mA / cm 2is required. In Table 2, the voltage U is shown as a relative voltage (rel. U), where the voltage of the reference component in the comparison example (SdT1 ) was set to 100% rel. U. The power efficiency EffP is the ratio of the radiated luminous flux (luminous power) in lumens (lm) to the supplied electrical power in watts (W) at a luminance of 1000 cd / m 2 . In Table 2, the power efficiency EffP is shown as relative power efficiency (rel. EffP), where the power efficiency of the reference component in the comparison example (SdT1 ) was set to 100% rel. EffP. The lifetime LT90 is defined as the time after which the luminance decreases during operation at a constant current density of 5 mA / cm 2 to 90% of the initial luminance. In Table 2, the lifetime LT90 is shown as a relative lifetime (rel. LT90), whereby the lifetime of the reference component in the comparison example (SdT1) was set to 100% rel. LT.

[0267] The following embodiment 1 corresponds to a preferred embodiment of the invention. SdT1 is an example of an OLED device using a prior art material. The details of the respective HIL, HTL, EBL, EML, HBL, ETL, and EIL are given in Table 1. The molecular structures used are given in Table 3.

[0268] Example 1: The EML comprises a hole-transporting host material H-1, an electron-transporting host material E-1, and a phosphorescent metal complex D-1. This OLED can be compared to an OLED according to Example SdT1 (Table 1). The two devices differ with respect to the electron-transporting host material used in the respective EML, i.e., E-1 according to the state of the art in the case of SdT1 and E-2 in the case of Ex. 1. The OLED according to Ex. 1 exhibits a better lifetime (LT90), a better power efficiency (EffP), and a better operating voltage (U) than the OLED according to SdT1.

[0269] Table 1 : Structure of the OLEDs Table 2: OLED results

[0270] Table 3: Structural formulas of OLED materials

Claims

Patent claims 1 . Compound according to formula (1 ), Formula (1) where Z represents a group selected from structures of formulas (Z-1) to (Z-4) Formula (Z-3) Formula (Z-4) where the dashed bond represents the bond to the nitrogen-containing heteroaryl group and the symbols continue to apply: W is C, Si or Ge; Y is chosen from C(R C )2, Si(R c )2, Ge(R c )2, 0 or S; L is a bond or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R d can be substituted differently from H; X a is the same or different at each occurrence N or CR a , where at least one group X a stands for N; X b is the same or different at each occurrence N or CR b, where at most two of the groups X b per ring stands for N; X c is the same or different at each occurrence N or CR C , where at most two of the groups X c per ring stands for N; R, R a , R b , R c , R d is the same or different at each occurrence H, D, F, CI, Br, I, OAr', SAr', N(R 1 )2, N(Ar')2, B(OR 1 )2, B(R 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , C(R 1 )3, Si(R 1 )3, Ge(R 1 )3, NO2, P(=O)(R 1 )2, P(Ar')2, P(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 1 may be substituted differently from H, where one or more non-adjacent CH2 groups are substituted by - R 1 C=CR 1 -, -C C-, Si(R 1 )2, CONR 1 , NR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 1 can be substituted differently from H, two residues can be selected from residues R a , R b , R c and R d also form a ring with each other; Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is substituted by one or more radicals R 1 different may be substituted by H, where two or more Ar' may form a ring with each other; R 1 is the same or different at each occurrence: H, D, F, CI, Br, I, N(R 2 )2, B(OR 2 )2, B(R 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2 )2, CN, C(=O)OR 2 , C(R 2 )3, Si(R 2 )3, Ge(R 2 )3, NO2, P(=O)(R 2 )2, P(R 2 )2, OSO2R 2 , SR 2 , S(=O)R 2 , S(=O)2R 2, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 2 may be substituted differently from H and wherein one or more CH2 groups in the above-mentioned groups are substituted by -R 2 C=CR 2 -, -C=C-, Si(R 2 )2, NR 2 , C=O, C=S, -C(=O)O-, CONR 2 , P(=O)(R 2 ), -S-, SO or SO2 and where one or more H atoms in the above-mentioned groups can be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted differently from H, where two or more radicals R 1 can form a ring with each other; R2 is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more substituents R 2 be linked together to form a ring; characterized in that the radical R does not form a ring with the group L.

2. A compound according to claim 1, characterized in that Z represents a group selected from structures of formulas (Z-5) to (Z-8), Formula (Z-7) Formula (Z-8) where the dashed bond represents the bond to the nitrogen-containing heteroaryl group and R c has the meaning given in claim 1.

3. A compound according to claim 1 or 2, characterized in that the compound corresponds to the following formula (2): Formula (2) where the symbols Z, R, R a , W, X a and X b , which have the meanings previously set out in claims 1 and 2 and the following applies to the further symbols: g is an integer in the range from 0 to 5, where g = 0 means that the group L a is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding atom, for example a carbon atom; and L a is a group chosen from structures of the formulas (L a -1 ) to (L a -5) Formula (L a -4) Formula (L a -5) where the dashed bonds represent the attachment points and the other symbols are: X d is the same or different at each occurrence N, CR d or, in the event that at this point the group L a binds to another group, C; Y ais chosen from C(R d )2, 0 or S, where R d has the meaning set out above in claim 1.

4. Connection according to claim 3, characterized in that the Group L a is chosen from structures of the formulas (L a -6) to (L a -15) Formula (L a -13) Formula (L a -14) Formula (L a -15) where the dashed bonds represent the attachment points, R d has the meaning given in claim 1 and the following applies to the other symbols: X d is the same or different at each occurrence N, CR d or, in the event that at this point the group L a binds to another group, C; i is 1 or 2; and j is 0, 1 or 2.

5. A compound according to claim 3 or 4, characterized in that the group L a is chosen from structures of the formulas (L a-16) to (L a -21 ) where the dashed bonds represent the attachment points and R d has the meaning given in claim 1.

6. A compound according to one or more of claims 3 to 5, characterized in that the Compound of one of the following formulas (3-1), (3-2) or (3-3) Formula (3-1) Formula (3-2) Formula (3-3) where the symbols Z, R, R a , R b , W and X a have the meanings previously set out in claims 1 and 2, the symbol L a has the meanings previously set out in claims 3, 4 and 5 and the index g has the meaning set out in claim 3.

7. A compound according to one or more of claims 3 to 6, characterized in that the compound corresponds to the following formula (4): Formula (4) where the symbols R 1 , R, R b , and R c have the meanings previously set out in claim 1, the symbol L a has the meanings previously set out in claims 3, 4 and 5 and the index g has the meaning set out in claim 3.

8. Compound according to one or more of claims 1 to 7, characterized in that R b , R c and R d at every occurrence is selected identically or differently from the group consisting of H, D, F, CN, OR 1 , a straight-chain alkyl group having 1 to 10 C atoms with 2 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein the alkyl group is in each case substituted with one or more radicals R 1may be substituted and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted.

9. A compound according to one or more of claims 1 to 8, characterized in that R and at least one radical R a is selected, identically or differently at each occurrence, from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted.

10. A compound according to one or more of claims 1 to 9, characterized in that the compound is at least 50% deuterated.

11. A process for preparing a compound according to one or more of claims 1 to 10, characterized by the following steps: (A) synthesizing a first subunit comprising a pyridine, pyrimidine or triazine residue containing a reactive leaving group; (B) introducing a second subunit comprising an aromatic or heteroaromatic residue by a coupling reaction.

12. Formulation comprising at least one compound according to one or more of claims 1 to 10 and at least one further compound and / or at least one solvent.

13. Use of a compound according to one or more of claims 1 to 10 and / or a formulation according to claim 16 in an electronic device.

14. An electronic device comprising at least one compound according to one or more of claims 1 to 10.

15. The electronic device according to claim 14, which is an organic electroluminescent device, characterized in that the device comprises an anode, a cathode and at least one emitting layer, wherein at least one organic layer, which may be an emitting layer, electron transport layer, hole blocking layer or another functional layer, comprises at least one compound according to one or more of claims 1 to 10.

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