Heterocyclic Compounds

Abstract

To provide heterocyclic compounds for use in electronic devices.SOLUTION: There is provided a compound comprising a structure of a formula (I). (Where X is N or CR (R is H, D, OH, F, Cl, Br, I, or the like); Ra is H, D, F, Cl, Br, I, CN, NO2 or the like.).SELECTED DRAWING: None

Description

Detailed Description of the Invention

[0001] The present invention relates to heterocyclic compounds, in particular for use in electronic devices. The present invention further relates to processes for the preparation of the compounds of the invention and to electronic devices comprising these compounds.

[0002] The structure of organic electroluminescent devices (OLEDs), in which organic semiconductors are used as functional materials, is known to those skilled in the art. The emitting materials used are often phosphorescent organometallic complexes. For quantum mechanical reasons, the use of organometallic compounds as phosphorescent emitters allows for up to four times higher energy and power efficiency. There is still a need for improvements in OLEDs in general, and in phosphorescent OLEDs in particular, for example with regard to efficiency, operating voltage and lifetime.

[0003] The properties of organic electroluminescent devices are not only determined by the emitters used. Of particular importance here are the other materials used, such as host and matrix materials, hole blocking materials, electron transport materials, hole transport materials, and electron or exciton blocking materials. Improvements in these materials can lead to significant improvements in electroluminescent devices.

[0004] In the prior art, aromatic or heteroaromatic compounds (such as triarylamine derivatives or carbazole derivatives) are often used as phosphorescent compounds and electron transport materials. In addition, triazine or pyrimidine derivatives are also used as matrix materials.

[0005] In general, in the case of these materials, which are used, for example, as matrix materials, there is still a need for improvements in the devices, especially with regard to their lifetime, but also with regard to their efficiency and operating voltage.

[0006] The problem addressed by the present invention is therefore to provide compounds which are suitable for use in organic electronic devices, in particular organic electroluminescent devices, and which exhibit good device properties when used in said devices, and to provide corresponding electronic devices.

[0007] More particularly, the problem addressed by the present invention is to provide compounds which lead to high lifetime, good efficiency and low operating voltage. In particular, the properties of the matrix material also have a significant influence on the lifetime and efficiency of organic electroluminescent devices.

[0008] A further problem addressed by the present invention is to provide compounds that are particularly suitable as matrix materials in phosphorescent or fluorescent OLEDs. A particular problem addressed by the present invention is to provide matrix materials that are suitable for red, yellow and green phosphorescent OLEDs, and possibly also for blue phosphorescent OLEDs.

[0009] Moreover, especially when the compound is used as a matrix material, a hole conducting material, or an electron transporting material in organic electroluminescence, the compound will lead to the device with excellent color purity.

[0010] Furthermore, the compounds must be processable in a very simple manner and must in particular exhibit good solubility and film-forming properties, for example they must exhibit oxidative stability on heating and improved glass transition temperatures.

[0011] A further object is to provide electronic components with excellent performance at very low cost and with consistent quality.

[0012] Also, the electronic device must be capable of being used or adapted for many purposes, and more particularly, the performance of the electronic device must be maintained over a wide temperature range.

[0013] Surprisingly, it has been found that these problems are solved by a specific compound, which will be described in detail below. The use of this compound leads to very good properties of organic electronic devices, particularly organic electroluminescent devices, in terms of lifetime, color purity, efficiency and operating voltage. Therefore, the present invention provides an electronic device, particularly an organic electroluminescent device, comprising such a compound and corresponding preferred forms.

[0014] Thus, the present invention provides compounds comprising at least one structure of formula (I): [ka] Here, the symbols used are as follows: X is identical or different at each occurrence and is N or CR, preferably CR; R a are the same or different for each occurrence and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar a )2, N(R)2, C(=O)Ar a , C(=O)R 2 , P(=O)(Ar a )2, P(Ar a )2, B(Ar a )2, B(OR)2, Si(Ar a)3, Si(R)3, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R radicals, wherein one or more non-adjacent CH2 groups are replaced by -RC=CR-, -C≡C-, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, -O-, -Se-, -S-, C=Se, -C(=O)O-, -C(=O)NR-, C=NR, NR, P(=O)(R), SO, or SO2. and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and optionally substituted by one or more R radicals, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and optionally substituted by one or more R radicals, or a combination of these systems; a The radicals, together with each other or with the R radical, may form a ring system; Ar a are identical or different at each occurrence and are aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms and optionally substituted by one or more non-aromatic R radicals; and at the same time, two Ar a It is also possible that the radicals are linked together via a bridge by a single bond or a bridge selected from B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, O, S, Se, S=O, SO2, N(R), P(R) and P(=O)R; R is the same or different at each occurrence and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R1 )2, C(=O)Ar, C(=O)R 1 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, B(OR 1 )2, Si(Ar)3, Si(R 1 ) 3. A linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms (each of which may be selected from the group consisting of one or more R 2 radical, where one or more non-adjacent CH groups are replaced by -R 1 C=CR 1 -, -C≡C-, Si(R 1 )2, Ge(R 1 )2, Sn(R 1 )2, C=O, C=S, C=Se, -C(=O)O-, -C(=O)NR 1 -, C=NR 1 , N.R. 1 , P(=O)(R 1 ), -O-, -S-, -Se-, SO or SO2, and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms (each of which may be replaced by one or more R 1 or having 5 to 60 aromatic ring atoms and one or more R 1 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 60 aromatic ring atoms and one or more R 1 aralkyl or heteroaralkyl groups, or combinations of these systems, optionally substituted by radicals; at the same time, two or more, preferably adjacent R 1 the radicals may together form a ring system; Ar is the same or different at each occurrence and has 5 to 30 aromatic ring atoms and one or more non-aromatic R 1at the same time, two Ar radicals bonded to the same silicon, nitrogen, phosphorus or boron atom are bridged by a single bond or by B(R 1 ), C(R 1 )2, Si(R 1 )2, C=O, C=NR 1 , C=C(R 1 )2, O, S, Se, S=O, SO2, N(R 1 ), P(R 1 ) and P(=O)R 1 may also be coupled together via a bridge selected from: R 1 are the same or different for each occurrence and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar 1 )2, N(R 2 )2, C(=O)Ar 1 , C(=O)R 2 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1 )2, B(OR 2 )2, Si(Ar 1 )3, Si(R 2 ) 3. A linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms (each of which may be selected from the group consisting of one or more R 2 radical, where one or more non-adjacent CH groups are replaced by -R 2 C=CR 2 -, -C≡C-, Si(R 2 )2, Ge(R 2 )2, Sn(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2), -O-, -S-, -Se-, SO or SO2, and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), or having 5 to 40 aromatic ring atoms and in each case one or more R 2 an aromatic or heteroaromatic ring system, or a ring system having 5 to 40 aromatic ring atoms, optionally substituted by a radical, and one or more R 2 an aryloxy or heteroaryloxy group, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 2 aryl or heteroaryl groups, or combinations of these systems, optionally substituted by radicals; 1 the radicals may together form a ring system; Ar 1 are the same or different at each occurrence and have 5 to 30 aromatic ring atoms and one or more non-aromatic R 2 at the same time, two Ar 1 -(Ar 2 -(Ar 3 -(Ar 4 -(Ar 5 -(Ar 6 -(Ar 7 -(Ar 8 -(Ar 9 -(Ar 10 -(Ar 11 -(Ar 12 -(Ar 13 -(Ar 14 -(Ar 15 -(Ar 16 -(Ar 17 -(Ar 18 -(Ar 19 ...1 1 The radical is bridged by a single bond or B(R 2 ), C(R 2 )2, Si(R 2 )2, C=O, C=NR 2 , C=C(R 2 )2, O, S, Se, S=O, SO2, N(R 2 ), P(R 2 ) and P(=O)R 2 may also be coupled together via a bridge selected from: R 2 are the same or different for each occurrence, H, D, F, Cl, Br, I, CN, B (OR 3 )2, NO2, C(=O)R 3 , C.R. 3 =C(R 3 )2, C(=O)OR 3 , C(=O)N(R 3 )2, Si(R3 )3, P(R 3 )2, B(R 3 )2, N(R 3 )2, NO2, P(=O)(R 3 )2, OSO2R 3 , OR 3 , S(=O)R 3 , S(=O)2R 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be selected from the group consisting of one or more R 3 radical, where one or more non-adjacent CH groups are replaced by -R 3 C=CR 3 -, -C≡C-, Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=NR 3 , -C(=O)O-, -C(=O)NR 3 -, NR 3 , P(=O)(R 3 ), -O-, -S-, -Se-, SO or SO2, and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), or having 5 to 40 aromatic ring atoms and in each case one or more R 3 an aromatic or heteroaromatic ring system, or a ring system having 5 to 40 aromatic ring atoms, optionally substituted by a radical, and one or more R 3 aryloxy or heteroaryloxy groups, or combinations of these systems, optionally substituted by radicals; at the same time, two or more, preferably adjacent R 2 the substituents may together form a ring system; R 3are identical or different at each occurrence and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and may be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; 3 It is possible for the substituents to take together to form a ring system.

[0015] Preferably, R is 1 or less. a The group is OH and one R a If the group is OH, the second R a This may be the case when the group is not F, Cl, Br, I or CN.

[0016] In the context of the present invention, adjacent carbon atoms are carbon atoms that are directly bonded to each other. Furthermore, in the definition of radicals, "adjacent radicals" means that these radicals are bonded to the same carbon atom or adjacent carbon atoms. These definitions apply in particular to the terms "adjacent groups" and "adjacent substituents".

[0017] The expression that two or more radicals may form a ring with each other is understood in the context of the present invention to mean, in particular, that the two radicals are linked to each other by a chemical bond under the formal removal of two hydrogen atoms. This is illustrated by the following scheme: [ka]

[0018] Furthermore, however, the above expression is also understood to mean that if one of the two radicals is hydrogen, the second radical is bonded to the bonded position of the hydrogen atom to form a ring, which is illustrated by the following scheme: [ka]

[0019] In the context of the present invention, fused aryl group, fused aromatic ring system or fused heteroaromatic ring system is a group in which two or more aromatic groups are fused to each other through one common side, i.e. fused rings, for example, two carbon atoms belong to at least two aromatic or heteroaromatic rings, such as in naphthalene.In contrast, for example, fluorene is not a fused aryl group in the context of the present invention, since the two aromatic groups in fluorene do not have a common side.The corresponding definition applies to heteroaryl groups and fused ring systems that may but do not have to contain heteroatoms.

[0020] In the context of the present invention, an aryl group contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms; in the context of the present invention, a heteroaryl group contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl or heteroaryl group is understood here to mean a single aromatic ring, i.e. benzene, or a single heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or fused, aryl or heteroaryl groups, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.

[0021] In the context of the present invention, an aromatic ring system has 6 to 60 carbon atoms in the ring system, preferably 6 to 40 carbon atoms. In the context of the present invention, a heteroaromatic ring system contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatom is preferably selected from N, O and / or S. In the context of the present invention, an aromatic or heteroaromatic ring system should be understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be interrupted by non-aromatic units (preferably less than 10% of atoms other than H), such as carbon, nitrogen or oxygen atoms or carbonyl groups. For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, stilbenes, etc., are also considered as aromatic ring systems in the context of the present invention, as are systems in which two or more aryl groups are interrupted, for example, by linear or cyclic alkyl groups or by silyl groups. Additionally, systems in which two or more aryl or heteroaryl groups are directly bonded to each other, such as biphenyl, terphenyl, quaterphenyl, or bipyridine, are also considered aromatic or heteroaromatic ring systems.

[0022] In the context of this invention a cyclic alkyl, alkoxy or thioalkoxy group is taken to mean a monocyclic, bicyclic or polycyclic group.

[0023] In the context of the present invention, C1-C alkoxy groups, in which individual hydrogen atoms or CH2 groups may be replaced by the above-mentioned groups, are 20The alkyl group in the formula (I) is, for example, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl. 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hepta- 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-hexadece-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, It is understood to mean 1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadece-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)cyclohex-1-yl, 1-(n-butyl)cyclohex-1-yl, 1-(n-hexyl)cyclohex-1-yl, 1-(n-octyl)cyclohex-1-yl and 1-(n-decyl)cyclohex-1-yl radicals. Alkenyl groups are understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. C1-C. 40 An alkoxy group is taken to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

[0024] Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, which may in each case be substituted by the abovementioned radicals and which may be bonded to the aromatic or heteroaromatic system in any desired position, are understood to mean, for example, radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyls, phenylsulfone ... phenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole , indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazo , phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole.

[0025] In a preferred embodiment, preferably at least one R a This may be the case where the radicals, preferably both, are aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms and which in each case may be substituted by one or more R radicals.

[0026] In a further variation, at least one R a This may also be the case where the radicals, preferably both, are linear alkyl, alkoxy or thioalkoxy groups having 1 to 40 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy groups having 3 to 40 carbon atoms or alkenyl or alkynyl groups having 2 to 40 carbon atoms, each of which may be substituted by one or more R radicals.

[0027] In a preferred form, the compounds of the invention may comprise at least one structure of formula (IIa), (IIb), (IIc) or (IId). [ka] where p is 0 or 1, Y is B(R), C(R), Si(R), C=O, C=NR, C=C(R), O, S, Se, S=O, SO, N(R), P(R) and P(=O)R, preferably B(R), C(R), Si(R), O, S, Se, S=O, SO, N(R), P(R) and P(=O)R, and the symbols R and X used have the meanings given above, in particular in formula (I). When p=0, there is a bond between the indicated aromatic or heteroaromatic rings.

[0028] Preferably, in formula (I), (IIa), (IIb), (IIc) or (IId), not more than two X groups per ring are N; preferably at least one, more preferably at least two X groups per ring are selected from CH and CD.

[0029] Preferably, in formula (I), (IIa), (IIb), (IIc) or (IId), not more than 4, preferably not more than 2, X groups are N; more preferably, all X groups are CR 1 where X denotes the CR 1 At most 4, more preferably at most 3, particularly preferably at most 2 of the groups are not CH groups.

[0030] Preferably, the compounds of the present invention may comprise the structure of formula (IIIa), (IIIb), (IIIc) and / or (IIId). [ka] wherein l is 1, 2, 3, 4 or 5, preferably 0, 1 or 2, and m is 0, 1, 2, 3, or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and the symbols R, Y and p used have the meanings given above, in particular in formulae (I) and / or (II), where the sum of the indices l and m is preferably up to 6, particularly preferably up to 4 and especially preferably up to 2. If p=0, then there is a bond between the indicated aromatic rings.

[0031] Furthermore, in the structures of formulae (I), (IIc), (IId), (IIIc), and (IIId), at least one R a or R radicals, preferably one R a or the R radical is a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, preferably having 1 to 10 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, preferably having 1 to 10 carbon atoms (which may be one or more R or R 1 This may be the case when the radical is substituted or preferably unsubstituted, where preference is given to alkyl groups rather than alkoxy or thioalkoxy groups.

[0032] Further, preferably, at least one R a and / or the R radical is, independently in each case, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, preferably having 1 to 10 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, preferably having 1 to 10 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, preferably having 5 to 24 aromatic ring atoms, particularly preferably having 5 to 18 aromatic ring atoms (which is represented by one or more R or R 1 a heteroaromatic ring system (which may be substituted by one or more R or R radicals), preferably having 5 to 40 aromatic ring atoms, preferably having 5 to 24 aromatic ring atoms, particularly preferably having 5 to 18 aromatic ring atoms; 1 a aryl or heteroaryl group (which may be substituted by one or more R or R radicals), more preferably having 5 to 40 aromatic ring atoms, preferably having 5 to 24 aromatic ring atoms, particularly preferably having 5 to 18 aromatic ring atoms; 1and wherein the aryl group is an aryl group having from 6 to 40 aromatic ring atoms, preferably from 5 to 24 aromatic ring atoms, and particularly preferably from 5 to 18 aromatic ring atoms, and the aryl group is an aryl group having from 6 to 40 aromatic ring atoms, preferably from 5 to 24 aromatic ring atoms, and particularly preferably from 5 to 18 aromatic ring atoms.

[0033] Furthermore, it may be the case that the substituent R of the heteroaromatic ring system of formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) and / or (IIId) does not form a fused aromatic or heteroaromatic ring system together with the ring atoms of the heteroaromatic ring system, preferably does not form any fused ring system. 1 , R 2 , R 3 It includes forming a fused ring system together with the substituents, which may be attached to the R radical. Preferably, this may be the case where the substituents R in formulae (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) and / or (IIId) do not form any ring system together with the ring atoms of the heteroaromatic ring system. This is in accordance with the possible R 1 , R 2 , R 3 It includes forming a fused ring system together with the substituents (which may be attached to the R radical).

[0034] Especially R a , R, R 1 , R 2 , R and / or R 3 When two radicals, which may be selected from, together form a ring system, this ring system may be monocyclic or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic. In this case, the radicals which together form a ring system may be adjacent, that is, they may be bonded to the same carbon atom or to carbon atoms which are directly bonded to each other, or they may be further removed from each other.

[0035] In a preferred embodiment, the compounds of the present invention can be represented by the structure of formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) and / or (IIId). Thus, preferred are compounds of the structure of formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) and / or (IIId). Preferably, the compounds comprising the structure of formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) and / or (IIId) have a molecular weight of 5000 g / mol or less, preferably 4000 g / mol or less, particularly preferably 3000 g / mol or less, especially preferably 2000 g / mol or less, and most preferably 1200 g / mol or less.

[0036] A further feature of the preferred compounds of the invention is that they are sublimable. These compounds generally have a molar mass of less than about 1200 g / mol.

[0037] In a further preferred embodiment, R a and / or the R group is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each of which may be selected from the group consisting of one or more R or R 1Radicals (except fluorenyl and carbazolyl) which may be substituted, but are preferably unsubstituted), particularly preferably those selected from the group consisting of spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylene groups.

[0038] When X is CR or when the aromatic and / or heteroaromatic groups are substituted by substituents R, these substituents R are preferably H, D, F, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, linear alkyl or alkoxy groups having 1 to 10 carbon atoms or branched or cyclic alkyl or alkoxy groups having 3 to 10 carbon atoms or alkenyl groups having 2 to 10 carbon atoms, each of which may be selected from the group consisting of one or more R 1 radicals, in which one or more non-adjacent CH groups are optionally replaced by O and in which one or more hydrogen atoms are optionally replaced by D or F), having 5 to 24 aromatic ring atoms and in each case having one or more R 1 Aromatic or heteroaromatic ring system or a ring system having 5 to 25 aromatic ring atoms, which may be substituted by a radical, but is preferably unsubstituted, and one or more R 1 at the same time, optionally, two substituents R attached to the same carbon atom or adjacent carbon atoms are a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system (which is one or more R 1 Ar may be the same or different in each occurrence, have 5 to 40 aromatic ring atoms, and in each case may be one or more R 1 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 1 an aryloxy group, optionally substituted by a radical, or an aryloxy group having 5 to 40 aromatic ring atoms, in each case one or more R1 An aralkyl group optionally substituted by a radical (wherein two or more, preferably adjacent, R 1 The substituents are optionally monocyclic or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring systems, preferably monocyclic or polycyclic aliphatic ring systems (which may be one or more R 2 may be substituted with a radical, where the symbol R 2 may have the meanings given above, in particular in formula (I). Preferably, Ar is identical or different at each occurrence and is an aryl or heteroaryl group having 5 to 24, preferably 5 to 12, aromatic ring atoms, which in each case is joined to one or more R 2 It may be substituted by, but is preferably unsubstituted.

[0039] Examples of suitable Ar groups are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl (each of which may be selected from the group consisting of one or more R 1 The radicals may be substituted, but are preferably unsubstituted.

[0040] More preferably, these substituents R are H, D, F, CN, N(Ar), a linear alkyl group having 1 to 8 carbon atoms, preferably 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably 3 or 4 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably 2, 3 or 4 carbon atoms (each of which may be represented by one or more R 1radicals, but preferably unsubstituted), or having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms, and in each case one or more non-aromatic R 1 at the same time, optionally, two substituents R attached to the same carbon atom or adjacent carbon atoms are selected from the group consisting of a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system (which is one or more R 1 It is possible to form the formula (III) (optionally substituted by radicals), in which Ar may have the meaning given above.

[0041] Most preferably, the R substituents are selected from H and aromatic or heteroaromatic ring systems having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, each of which may be joined by one or more non-aromatic R 1 The radicals may be substituted, but are preferably unsubstituted.

[0042] Preferably, this may be the case where the compound comprises a hole transport group, where preferably R a One of the groups, or one of the R groups, comprises, and preferably is, a hole transporting group.

[0043] In a further embodiment, R a and / or one of the R radicals is selected from an arylamino group, preferably a di- or triarylamino group, a heteroarylamino group, preferably a di- or triheteroarylamino group, a carbazole group, preferably a carbazole group, which may also be considered as a hole transporting group.

[0044] Preferably, the hole transport group comprises a group selected from formulae (H-1) to (H-3), and is preferably a group selected from formulae (H-1) to (H-3). [ka] where the dotted bond indicates the position of attachment, and Ar 2 , Ar 3 , Ar 4 each independently represents an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, each of which may be represented by one or more R 1 and optionally substituted by radicals; p is 0 or 1, and W 1 is a bond, C(R 1 )2, Si(R 1 )2, C=O, N-Ar 1 , B.R. 1 , P.R. 1 , POR 1 , SO, SO2, Se, O or S, preferably C(R 1 )2, N-Ar 1 , O or S, where the symbol Ar 1 and R 1 has the meaning given above, preferably in formula (I) and / or (II), where the presence of an NN bond is preferably excluded and, for example, W 1 In the case where is NR or NAr, the index p is 1.

[0045] Furthermore, the hole transport group may comprise a group selected from formulae (H-4) to (H-36), and is preferably a group selected from formulae (H-4) to (H-26). [ka] [ka] Here, Y 1 is O, S, C(R 1 )2 or NAr 1where the dotted line indicates the bond position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is 0, 1, 2, 3 or 4, p is 0 or 1, and Ar 2 has the meaning given above, in particular in formula (H-1) or (H-2), and Ar 1 and R 1 has the meaning given above, especially in formula (I) and / or (II).

[0046] Preferably, the presence of N-N bonds is excluded, e.g., in the cases where Y=NAr in formulae (H-5), (H-6), (H-9), (H-12), (H-15), (H-18), (H-21), (H-24), (H-25) and (H-26), the index p is preferably 1.

[0047] Of the groups (H-1) to (H-26), a carbazole group, particularly groups (H-4) to (H-26), is preferred.

[0048] Preferably, Ar 2 The group is an aromatic or heteroaromatic radical or a nitrogen atom (combined with the Ar 2 A through-conjugation may be formed with the aryl group (to which the aryl group may be bonded).

[0049] In a further preferred embodiment of the present invention, Ar 2 is an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be one or more R 1 radical, which may be substituted but is preferably unsubstituted, where R 1 may have the meanings given above, especially in formula (I). More preferably, Ar 2 is an aromatic ring system having 6 to 10 aromatic ring atoms, or a heteroaromatic ring system having 6 to 13 aromatic ring atoms, each of which is represented by one or more R 1 may be substituted, but is preferably unsubstituted, by a radical, where R1 may have the meaning given above, especially in formula (I).

[0050] More preferably, the symbol Ar 2 is especially an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, more preferably 6 to 10 ring atoms, in which the aromatic or heteroaromatic group of the aromatic or heteroaromatic ring system is bonded directly to the respective atom of a further group, i.e. via an atom of the aromatic or heteroaromatic group.

[0051] Furthermore, in the compound used as a hole transport material or a host material, Ar 2 It may be the case that the group comprises an aromatic ring system having up to two fused aromatic and / or heteroaromatic rings, preferably does not contain any fused aromatic or heteroaromatic ring system. Thus, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or benzothienyl structures are preferred over naphthyl structures. Particularly preferred are structures that do not have fusion, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0052] Suitable aromatic or heteroaromatic ring systems Ar 2 are ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, especially branched terphenylene, quaterphenylene, especially branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, each of which may be selected from the group consisting of one or more R 2 The radicals may be substituted, but are preferably unsubstituted.

[0053] Ar represented by formulas (H-1) to (H-26) 2The group may especially be the case having up to one nitrogen atom, preferably up to two heteroatoms, particularly preferably up to one heteroatom, and more preferably no heteroatoms.

[0054] In a further preferred embodiment of the present invention, Ar 3 and / or Ar 4 are identical or different at each occurrence and are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably an aromatic ring system having 6 to 12 aromatic ring atoms or a heteroaromatic ring system having 5 to 13 aromatic ring atoms, each of which may be selected from one or more R 1 may be substituted, but is preferably unsubstituted, by a radical, where R 1 may have the meanings given above, in particular in formula (I) and / or (II). 3 and / or Ar 4 Exemplary groups are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which may be selected from the group consisting of one or more R 1 The radicals may be substituted, but are preferably unsubstituted.

[0055] Preferably, R 1 The radical is an aryl or heteroaryl group Ar 1 , Ar 2 , Ar 3 and / or Ar 4 (In this, R in formulas (H-1) to (H-26) 1 The ring atoms of the R 2 , R 3 The substituent (which is R 1or R 2 The term "aryl" includes forming a fused ring system with the ring (which may be attached to the radical).

[0056] Preferably, this may be the case where the compound comprises an electron transport group, where preferably R a One of the groups, or one of the R groups, comprises, and preferably is, an electron transport group, which are well known in the art and facilitate the ability to transport and / or conduct electrons.

[0057] In addition, R a Surprising advantages are exhibited by compounds comprising at least one structure of formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc), (IIId) or preferred forms thereof, wherein and / or the R group comprises at least one structure selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole, particularly preferably pyrimidine, triazine and quinazoline.

[0058] In a preferred embodiment of the invention, R a This may be the case where one of the groups or one of the R groups comprises an electron transport group that can be represented by formula (QL), preferably is an electron transport group that can be represented by formula (QL). [ka] Here, L 1 has a bond or 5 to 40, preferably 5 to 30, aromatic ring atoms, and one or more R 1 represents an aromatic or heteroaromatic ring system, optionally substituted by radicals, and Q represents an electron transport group, where R 1 has the meaning given above, especially in formula (I).

[0059] Preferably, the Q group, or electron transport group, especially as shown in formula (QL), may be selected from structures of formula (Q-1), (Q-2), (Q-4), (Q-3), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and / or (Q-10). [ka] where the dotted lines indicate the bond positions, Q' may be the same or different for each occurrence, and CR 1 or N, and Q'' is NR 1 , O or S; where at least one Q' is N, and R 1 is as described above, particularly in formula (I).

[0060] Furthermore, the Q group, or electron transport group, especially shown in formula (QL), may preferably be selected from structures of formula (Q-11), (Q-12), (Q-13), (Q-14) and / or (Q-15). [ka] Here, the symbol R 1 has the meaning given above, especially in formula (I), and X 1 is N or CR 1 and the dotted bond indicates the bond position, where X 1 is preferably a nitrogen atom.

[0061] In a further aspect, the Q group, or electron transport group, particularly as shown in formula (QL), may be selected from structures of formula (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22). [ka] Here, the symbol R 1has the meaning described above, especially in formula (I), the dotted bond indicates the position of the bond, and m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n is 0, 1, 2 or 3, preferably 0, 1 or 2, and o is 0, 1 or 2, preferably 1 or 2. Here, preferred are structures of formulae (Q-16), (Q-17), (Q-18) and (Q-19).

[0062] In a further aspect, the Q group, or electron transport group, particularly as shown in formula (QL), may be selected from structures of formula (Q-23), (Q-24) and / or (Q-25). [ka] Here, the symbol R 1 has the meaning given above, especially in formula (I), and the dotted bond indicates the position of attachment.

[0063] In a further aspect, the Q group, or electron transport group, particularly as shown in formula (QL), may be selected from structures of formula (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30). [ka] Here, the symbol Ar 1 and R 1 has the meaning given above, especially in formula (I), and X 1 is N or CR 1 and the dotted bond indicates the bond position. Preferably, in the structures of formulae (Q-26), (Q-27) and (Q-28), exactly one X 1 is a nitrogen atom.

[0064] Preferably, the Q group, or electron transport group, especially as shown in formula (QL), may be selected from structures of formula (Q-31), (Q-32), (Q-33), (Q-34), (Q-35), (Q-36), (Q-37), (Q-38), (Q-39), (Q-40), (Q-41), (Q-42), (Q-43) and / or (Q-44). [ka] [ka] Here, the symbol Ar 1 and R 1 has the meaning given above, especially in formula (I), the dotted bond indicates the position of attachment and m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n is 0, 1, 2 or 3, preferably 0 or 1, n is 0, 1, 2 or 3, preferably 0, 1 or 2 and l is 1, 2, 3, 4 or 5, preferably 0, 1 or 2.

[0065] Preferably, the symbol Ar 1 is an aryl or heteroaryl radical, in which the aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly, i.e. via an aromatic or heteroaromatic atom, bonded to the respective atom of a further group, for example a carbon or nitrogen atom of (H-1) to (H-26) or (Q-16) to (Q-34) as shown above.

[0066] In a further preferred embodiment of the present invention, Ar 1 are identical or different at each occurrence and are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably an aromatic ring system having 6 to 12 aromatic ring atoms, or 6 to 13 aromatic ring atoms, and in each case one or more R 2 A heteroaromatic ring system, optionally substituted but preferably unsubstituted by radicals, where R 2 may have the meanings given above, especially in formula (I). 1The groups are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which may be selected from the group consisting of one or more R 2 The alkyl group may be substituted by a radical, but is preferably unsubstituted.

[0067] Ar in formulas (H-1) to (H-26) or (Q-16) to (Q-34) 1 has 6 to 12 aromatic ring atoms and at least one R 2 Advantageously, it is an aromatic ring system, which may be substituted by radicals, but is preferably unsubstituted, where R 2 may have the meaning given above, especially in formula (I).

[0068] Preferably, R in formulas (H-1) to (H-26) or (Q-1) to (Q-34) 1 The radical is a heteroaryl group, or R 1 Ar with radical attached 1 and / or Ar 2 Together with the ring atoms of the group, they do not form a fused ring system. This is because the possible substituents R 2 , R 3 (This is R 1 or R 2 The term "aryl" includes forming a fused ring system with the ring (which may be attached to the radical).

[0069] In a preferred embodiment, at least one R in formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) or (IIId) a or the R group is of the formula L 1 In some cases, L may be a group that can be represented by -Z. 1has a bond or 5 to 40, preferably 5 to 30, aromatic ring atoms and one or more R 1 represents an aromatic or heteroaromatic ring system, optionally substituted by radicals; Z is R 1 , Ar, or formula Z a or Z b where the symbols Ar and R 1 has the meaning given above, especially in formula (I), and Z a or Z b is as follows: [ka] wherein W is the same or different at each occurrence, has 5 to 30 aromatic ring atoms, and is one or more R 1 an aromatic or heteroaromatic ring system, a nitrogen atom, a boron atom, a phosphorus atom, or a phosphine oxide group, optionally substituted by a radical, the dotted bond indicating the point of attachment, and the symbols Ar and R 1 has the meaning given above, especially in formula (I).

[0070] Furthermore, at least one R in formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) or (IIId) a Or R groups are preferably all R a or the R group is of the formula R 1 This may be the case where the group can be represented by the radical:

[0071] Preferably, the compound of the present invention may comprise a structure of formula (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), (IVh), (IVi), (IVj), (IVk), (IVl), (IVm), (IVn), (IVo), (IVp), (IVq), (IVr), (IVs), (IVt), (IVu), (IVv), (IVw), (IVx) or (IVy). [ka] [ka] [ka] [ka] [ka] [ka] [ka] where l is 1, 2, 3, 4 or 5, preferably 0, 1 or 2, m is 0, 1, 2, 3, or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and n is 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 or 1, and the symbol R 1 , L 1 and Z are as defined above, in particular of the formula (I) and / or (L 1 -Z), in which the sum of the indices l, m and n is preferably at most 6, particularly preferably at most 4 and especially preferably at most 2.

[0072] Furthermore, in the structures of formulae (IVt) to (IVy), R 1 At least one of the radicals, preferably one, is a linear alkyl, alkoxy or thioalkoxy group having 1 to 40, preferably 1 to 10, carbon atoms, preferably a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40, preferably 1 to 10, carbon atoms, which is represented by one or more R 2 The radicals may be substituted but are preferably unsubstituted, where this is preferably the case being an alkyl group rather than an alkoxy or thioalkoxy group.

[0073] Preferably, the compound of the present invention may comprise a structure of formula (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg) or (Vh). [ka] [ka] [ka] where m is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and n is 0, 1, 2, or 3, preferably 0, 1, or 2, more preferably 0, 1, or 2, and the symbol R 1 , L 1 and Z are as defined above, in particular of the formula (I) and / or (L 1 -Z), in which the sum of the indices m and n is preferably at most 5, particularly preferably at most 3 and especially preferably at most 1.

[0074] Furthermore, in the structure of formula (Vf), (Vg) or (Vh), R 1 At least one of the radicals, preferably one, is a linear alkyl, alkoxy or thioalkoxy group having 1 to 40, preferably 1 to 10, carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40, preferably 1 to 10, carbon atoms, which is represented by one or more R 2 The radicals may be substituted but are preferably unsubstituted, whereby alkyl groups are preferred over alkoxy or thioalkoxy groups.

[0075] Preferably, the compounds of the present invention may include the structure of formula (VIa), (VIb), (VIc), (VId), (VIe), (VIf), VIg), (VIh), (VIi), (VIj), (VIk), (VIl), VIm), (VIn), (VIo), (VIp), (VIq), (VIr), (VIs) and (VIt). [ka] [ka] [ka] [ka] [ka] where l is 1, 2, 3, 4 or 5, preferably 0, 1 or 2, m is 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and n is 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 or 1, and the symbol R 1 , L 1 and Z are as defined above, in particular of the formula (I) and / or (L 1 -Z), wherein the sum of the indices l, m and n is preferably at most 5, particularly preferably at most 3 and especially preferably at most 1.

[0076] Furthermore, L in formula (IVa) to (IVy), (Va) to (Vh) or (VIa) to (VIt) 1 The -Z group may be the case to be a hole transporting group of formula (H-1) to (H-26) and / or an electron transporting group of formula (QL), preferably of formula (Q-1) to (Q-44).

[0077] Furthermore, formula L 1 In the structures of the formulae (IVa) to (IVy), (Va) to (Vh) and / or (VIa) to (VIt), the symbol Z is a group represented by the formulae (Z-1) to (Z1 -90). [ka] [ka] [ka] [ka] [ka] where the symbols used are: k is, independently for each occurrence, 0 or 1; i, independently at each occurrence, is 0, 1, or 2; j is independently at each occurrence 0, 1, 2 or 3; h is, independently at each occurrence, 0, 1, 2, 3, or 4; g, independently at each occurrence, is 0, 1, 2, 3, 4, or 5; The dotted bonds indicate the positions of bonds; and Ar 1 , R 1 has the meaning given above, especially in formula (I).

[0078] Preferably, L 1 The group Q or Z, and the group QL or L 1 -Z) 1 The group may form a direct conjugation with the atom to which it is bonded.As soon as a direct bond is formed between adjacent aromatic or heteroaromatic rings, the direct conjugation of the aromatic or heteroaromatic system is formed.An additional bond between the above-mentioned conjugated groups, for example via a sulfur, nitrogen or oxygen atom or a carbonyl group, does not impair the conjugation.In the case of the fluorene system, two aromatic rings are directly bonded, where the SP at the 9th position is 3 Although the -hybridized carbon atom prevents fusion of these rings, conjugation is possible, but this is due to the fact that the 9-SP 3This is because the -hybridized carbon atom is not necessarily located between the electron-transporting Q group and the nitrogen atom. In contrast, in the case of spirobifluorene structures, the Q group and the L 1 Direct conjugation can be formed when the bond between the aromatic or heteroaromatic radicals to which the groups are attached is through the same phenyl group in the spirobifluorene structure or through phenyl groups in the spirobifluorene structure that are directly bonded to each other and are in the same plane. 1 The bond between the aromatic or heteroaromatic radical to which the group is attached is the SP 9-position of the second spirobifluorene structure. 3 When the phenyl groups are bonded via different -hybridized carbon atoms, conjugation is prevented.

[0079] L 1 is an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which is 1 It may be substituted by a radical, but is preferably unsubstituted, where R 1 may have the meanings given above, especially in formula (I). More preferably, L 1 is an aromatic ring system having 6 to 10 aromatic ring atoms, or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be one or more R 2 It may be substituted by a radical, but is preferably unsubstituted, where R 2 may have the meaning given above, especially in formula (I).

[0080] More preferably, the formula (QL) or the formula (L 1 -Z) in the symbol L 1is identical or different on each occurrence and is a single bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms and more preferably 6 to 10 ring atoms, the aromatic or heteroaromatic ring system of which is directly, i.e. via an atom of the aromatic or heteroaromatic group, bonded to the respective atom of the further group.

[0081] It may also be the case that the aromatic ring system comprises up to two fused aromatic and / or heteroaromatic 6-membered rings, preferably without fused aromatic or heteroaromatic ring systems. Thus, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures.

[0082] Particularly preferred are non-fused structures, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0083] Suitable aromatic or heteroaromatic ring systems L 1 Examples of are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, particularly branched terphenylene, quaterphenylene, particularly branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene, and carbazolylene, each of which may be selected from the group consisting of one or more R 1 The radicals may be substituted, but are preferably unsubstituted.

[0084] Furthermore, in particular the formula (QL) or the formula (L 1 -Z) 1 The group may contain up to one nitrogen atom, preferably up to two heteroatoms, particularly preferably up to one heteroatom, and even more preferably no heteroatoms.

[0085] Preferably, the compound comprises at least one structure of formula (H-1) to (H-26) (wherein Ar 2 The group is a bond or a group of the formula (L 1 -1)~(L 1 -162)) and / or compounds comprising structures of formulae (IVa) to (IVy), (Va) to (Vh) and / or (VIa) to (VIp) (wherein the structural unit L 1 -L in Z 1 The group is a bond or a group of the formula (L 1 -1)~(L 1 -162)) and / or a compound (L) comprising the structure of the formula (QL) 1 The group is a bond or a group of the formula (L 1 -1)~(L 1 -162). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] where the dotted bonds indicate in each case the bond position, the subscript k is 0 or 1, the subscript l is 0, 1 or 2, the subscript j is, independently at each occurrence, 0, 1, 2 or 3, the subscript h is, independently at each occurrence, 0, 1, 2, 3 or 4, the subscript g is, independently at each occurrence, 0, 1, 2, 3, 4 or 5, and the symbol Y 1 is O, S or NR 1 , preferably O or S, and the symbol R 1 has the meaning given above, especially in formula (I).

[0086] Preferably, the formula (L 1 -1)~(L 1 -163), the sum of the subscripts k, l, g, h and j may in each case be at most 3, preferably at most 2, and more preferably at most 1.

[0087] The formula (QL) or (L 1 Preferred compounds of the invention having a group of —Z) represent a bond or have the formula (L 1 -163), (L 1 -1)~(L 1 -78) and / or (L 1 -92)~(L 1 -162), preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -54) and / or (L 1 -92)~(L 1 -162), particularly preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -29) and / or (L 1 -92)~(L 1 -162), L 1 Advantageously, the compound of formula (L 1 -163), (L 1 -1)~(L 1 -78) and / or (L 1 -92)~(L 1 -162), preferably of the formula (L 1 -163), (L1 -1)~(L 1 -54) and / or (L 1 -92)~(L 1 -162), particularly preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -29) and / or (L 1 -92)~(L 1 -162), in which the sum of the indices k, l, g, h and j in the structure may in each case be 3 or less, preferably 2 or less, and more preferably 1 or less.

[0088] Preferred compounds of the present invention having groups of the formulae (H-1) to (H-26) are represented by the formula (L 1 -163), (L 1 -1)~(L 1 -78) and / or (L 1 -92)~(L 1 -162), preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -54) and / or (L 1 -92)~(L 1 -162), particularly preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -29) and / or (L 1 -92)~(L 1 -162), 2 Advantageously, the compound of formula (L 1 -163), (L 1 -1)~(L 1 -78) and / or (L 1 -92)~(L 1 -162), preferably of the formula (L 1 -163), (L 1 -1)~(L 1 -54) and / or (L 1 -92)~(L 1 -162), particularly preferably of the formula (L 1 -163), (L 1 -1)~(L 1-29) and / or (L 1 -92)~(L 1 -162), the sum of the indices k, l, g, h and j in the structure may in each case be 3 or less, preferably 2 or less, and more preferably 1 or less.

[0089] Preferably, the formula (L 1 -1)~(L 1 -163) 1 The radical is R 1 The radical does not form a fused aromatic or heteroaromatic ring system with the ring atoms of the aryl or heteroaryl group to which it is attached, and preferably does not form any fused ring system. 1 or R 2 Possible R groups that may be attached to the radical 2 , R 3 The formation of fused ring systems with substituents is also included.

[0090] In addition, Ar 1 , Ar 2 , Ar 3 , Ar 4 and / or R 1 The radicals are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each of which may be selected from the group consisting of one or more R 1 or R 2It may be the case that the phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylene radicals are particularly preferred.

[0091] Furthermore, in the structures of formulae (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc)(IIId), (IVa)-(IVy), (Va)-(Vh) and / or (VIa)-(VIt), at least one R 1 or Ar 1 The radical has the formula (R 1 -1)~(R 1 -177), or in the structures of formulae (H-1) to (H-26), (Q-1) to (Q-44), and (Z-1) to (Z-91), at least one Ar 1 or R 1 The radical has the formula (R 1 -1)~(R 1 -177). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] where the symbols used are as follows: Y 1 is O, S or NR 2 , preferably O or S; i, independently at each occurrence, is 0, 1 or 2; j, independently at each occurrence, is 0, 1, 2 or 3; h is, independently at each occurrence, 0, 1, 2, 3 or 4; g, independently at each occurrence, is 0, 1, 2, 3, 4, or 5; R 2 has the meaning given above, especially in formula (I) and / or formula (II), and the dotted bond indicates the position of attachment.

[0092] The above formula (R 1 -1)~(R 1 Of the structures of formula (R 1 -1)~(R 1 -64) and (R 1 -94)~(R 1 -177), particularly preferably a group of the formula (R 1 -1)~(R 1 -64) and (R 1 -115)~(R 1 -177) base.

[0093] Preferably, the formula (R 1 -1)~(R 1 -177) in which the sum of the indices i, j, h and g is in each case 3 or less, preferably 2 or less, more preferably 1 or less.

[0094] Preferably, the formula (L 1 -1)~(L 1 -177) 2 The radical is R 2 The radical does not form a fused aromatic or heteroaromatic ring system with the ring atoms of the aryl or heteroaryl group to which it is attached, and preferably does not form any fused ring system. 2 Possible R groups that may be attached to the radical 3 The formation of fused ring systems with substituents is also included.

[0095] The compounds of the invention are aromatic or heteroaromatic R 1 or R 2 Substituted by groups, especially in the case of their form as host material, electron transport material or hole transport material, preferably does not have aryl or heteroaryl groups with more than two aromatic 6-membered rings fused together. More preferably, the substituent does not have any aryl or heteroaryl groups with 6-membered rings fused together. The reason for this is that the triplet energy of these structures is low. Despite being fused aryl groups with more than two aromatic 6-membered rings fused directly together, phenanthrene and triphenylene are also suitable in the present invention. Because they have high triplet levels.

[0096] In a further preferred embodiment of the invention, R 2 are, for example, identical or different at each occurrence in the structures of formula (I) and preferred forms of this structure or structures referred to in these formulas, and are selected from the group consisting of H, D, an aliphatic hydrocarbyl radical having 1 to 10 carbon atoms, preferably 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, preferably 5 to 24 aromatic ring atoms, more preferably 5 to 13 aromatic ring atoms, and which may be substituted, but preferably unsubstituted, by one or more alkyl groups each having 1 to 4 carbon atoms.

[0097] In a further preferred embodiment of the invention, R 3is, for example, identical or different at each occurrence in the structures of formula (I) and preferred forms of this structure or structures referred to in these formulas, and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 10 carbon atoms, preferably 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, preferably 5 to 24 aromatic ring atoms, more preferably 5 to 13 aromatic ring atoms, and which may be substituted, but preferably is unsubstituted, by one or more alkyl groups each having 1 to 4 carbon atoms.

[0098] Particularly preferred are compounds of the invention having the structure of formula (I) or (IIa)-(IId), in which a total of no more than four, preferably no more than two, radicals of formula X are not CH or CD, and in which at least one R a or the R radical comprises an electron transport group, preferably a triazine group, more preferably a group of formula (QL) where Q is a group of formula (Q-23) or (L1-Z) where Z is a group of formula (Z-48), and has the following characteristics: [ka]

[0099] Further, preferred are compounds of the invention having the structure of formula (IIIa), where p=0 and where the sum of the subscripts m is 3 or less, preferably 2 or less, particularly preferably 1, and where at least one R is an electron transport group, preferably a triazine group, more preferably a group of formula (QL) (where Q is a group of formula (Q-23)) or of formula (L 1 -Z), where Z is a group of formula (Z-48), having the following characteristics: [ka]

[0100] Particularly preferred are compounds of the invention having the structure of formula (IVa), (IVb), (IVc), preferably (IVa), or compounds having the structure of formula (Va), (Vb), (Ve), preferably (Vb), in which the sum of the indices m and n is less than or equal to 3, preferably less than or equal to 2, particularly preferably 0, and in which the group of formula (L1-Z) comprises at least one electron transport group, preferably a triazine group, more preferably a group of formula (L1-Z), in which Z is a group of formula (Z-48), and which have the following characteristics: [ka]

[0101] Examples of suitable compounds of the present invention are those of formulas 1-407 shown below: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0102] Preferred forms of the compounds of the invention are specifically illustrated in the Examples, and these compounds can be used alone or in combination with further compounds for all purposes of the invention.

[0103] The preferred embodiments described above can be combined with one another if desired, provided that the conditions specified in claim 1 are met. In a particularly preferred embodiment of the invention, the preferred embodiments described above are applied simultaneously.

[0104] The compounds of the invention can in principle be prepared in a variety of ways, however the methods described below have been found to be particularly suitable.

[0105] Thus, the present invention further provides a method for preparing a compound comprising the structure of formula (I) in which a compound comprising at least one nitrogen-containing heterocyclic group is combined with a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction.

[0106] Suitable compounds comprising at least one nitrogen-containing heterocyclic group are often commercially available, the starting compounds detailed in the examples being obtainable by known methods, as referenced therein.

[0107] Compounds comprising at least one nitrogen-containing heterocyclic group can be reacted with further aryl or heteroaryl compounds in known coupling reactions, the conditions necessary for this purpose are well known to those skilled in the art, and the detailed descriptions in the examples will assist those skilled in the art in carrying out these reactions.

[0108] Particularly suitable and preferred all coupling reactions leading to CC and / or CN bond formation are those due to Buchwald, Suzuki, Yamamoto, Stille, Heck, Negishi, Sonogashira and Hiyama. These reactions are well known and the examples provide further guidance to the skilled artisan.

[0109] In all of the synthetic schemes that follow, the compounds are shown with a small number of substituents to simplify the structures, and this does not preclude the presence of additional substituents as desired in the process.

[0110] Exemplary embodiments are shown in the following schemes, without these being intended to be limiting in any way: The constituent steps of the individual schemes can be combined with each other if desired. Scheme 1: [ka] Scheme 2: [ka] Scheme 3: [ka]

[0111] The definitions of the symbols used in Schemes 1 to 3 are as follows: 1-Z, and for clarity, the numbering is omitted.

[0112] The methods shown for the synthesis of the compounds of the present invention should be considered as illustrative only: a person skilled in the art may develop alternative synthetic routes within the scope of his / her common knowledge in the art.

[0113] The basics of the preparation methods detailed above are in principle known from the literature for similar compounds and can be readily adapted by those skilled in the art to the preparation of the compounds of the invention. Further information can be found in the Examples.

[0114] By these methods, optionally followed by purification, such as recrystallization or sublimation, the compounds of the present invention comprising the structure of formula (I) can be obtained in high purity, preferably greater than 99% ( 1 H-NMR and / or HPLC).

[0115] The compounds of the invention may also have suitable substituents, such as relatively long alkyl groups (about 4 to 20 carbon atoms), especially branched alkyl groups, or optionally substituted aryl groups, such as xylyl, mesityl or branched terphenyl or quaterphenyl groups, which provide solubility in standard organic solvents, such as toluene or xylene, at room temperature and at sufficient solubility concentrations to allow the compounds to be processed in solution. These soluble compounds are particularly suitable for processing in solution, for example by printing methods. Moreover, it must be emphasized that the compounds of the invention, which comprise at least one structure of formula (I), already have increased solubility in these solvents.

[0116] The compounds of the present invention can also be mixed with polymers. It is also possible to covalently incorporate these compounds into polymers. This is especially possible for compounds substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic ester, or with reactive polymerizable groups such as olefins or oxetanes. They find use as monomers for producing the corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably carried out via halogen or boronic acid functional groups, or via polymerizable groups. It is possible to further crosslink the polymer via such groups. The compounds and polymers of the present invention can be used in the form of crosslinked or non-crosslinked layers.

[0117] The present invention further provides polymers, oligomers or dendrimers comprising one or more structures of formula (I) or compounds of the invention as detailed above, in which there are one or more bonds to the compounds of the invention or to the structures of formula (I) to the oligomer, polymer or dendrimer. By linking the structures or compounds of formula (I), they therefore form side chains of the polymer or oligomer or are linked within the main chain. The polymers, oligomers or dendrimers may be conjugated, partially conjugated or not conjugated. The oligomers or polymers may be linear, branched or dendritic. For the repeat units of the compounds of the invention in the oligomers, dendrimers and polymers, the same preferred forms apply as described above.

[0118] To prepare oligomers or polymers, the monomers of the invention are homopolymerized or copolymerized with further monomers. The units of formula (I) or the preferred forms described above and below are preferably present in the range of 0.01 to 99.9 mol %, preferably 5 to 90 mol %, more preferably 20 to 80 mol %. Suitable and preferred comonomers forming the polymer backbone are fluorenes (for example according to EP 842208 or WO 2000 / 022026), spirobifluorenes (for example according to EP 707020, EP 894107 or WO 2006 / 061181), paraphenylenes (for example according to WO 92 / 18552), carbazoles (for example according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes ( For example, according to EP1028136), dihydrophenanthrenes (for example, according to WO2005 / 014689), cis- and trans-indenofluorenes (for example, according to WO2004 / 041901 or WO2004 / 113412), ketones (for example, according to WO2005 / 040302), phenanthrenes (for example, according to WO2005 / 104264 or WO2007 / 017066), or a plurality of these units. The polymers, oligomers and dendrimers may also contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.

[0119] Furthermore, of particular interest are compounds of the invention characterized by a high glass transition temperature. In this connection, preference is given to compounds of the invention comprising the structure of formula (I) or the preferred forms described above and below, which have a glass transition temperature (measured according to DIN 51005 (2005-08 edition)) of at least 70°C, more preferably at least 110°C, even more preferably at least 125°C, and especially preferably at least 150°C.

[0120] To process the compounds of the invention in liquid phase, for example by spin-coating or printing methods, a formulation of the compounds of the invention is required. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, it is preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone ... Examples of the solvent include cyclohexane, cyclohexanediol ...

[0121] Therefore, the present invention also relates to a formulation comprising the compound of the present invention and at least one further compound.The further compound is, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents.Alternatively, the further compound can be an organic or inorganic compound, for example a light-emitting compound, in particular a phosphorescent dopant, and / or a further matrix material, which are also used in electronic devices.This further compound can also be a polymer.

[0122] Therefore, the present invention further provides a composition comprising the compound of the present invention and at least one additional organic functional material.The functional material is generally an organic or inorganic material that is introduced between the anode and the cathode.Preferably, the organic functional material is selected from the group consisting of fluorescent emitter, phosphorescent emitter, multi-leg emitter, emitter that shows TADF (thermally activated delayed fluorescence), host material, electron transport material, electron injection material, hole transport material, hole injection material, electron blocking material, hole blocking material, wide gap material and n-dopant.

[0123] In a particular embodiment of the present invention, the compounds according to the invention can be used as matrix materials, in particular for phosphorescent emitters, which matrix materials are in many cases used in combination with further matrix materials.

[0124] The present invention therefore also relates to a composition comprising at least one compound comprising a structure of formula (I), or the preferred forms described above and below, the preferred forms of which are described above and below, and at least one further matrix material.

[0125] The present invention further provides compositions comprising at least one compound comprising at least one of the structures of formula (I) or preferred forms described above and below, and at least one wide band gap material, where wide band gap material is understood to mean the material disclosed in US 7,294,849. These systems show particularly advantageous performance data in electroluminescent devices.

[0126] Preferably, the additional compound has a band gap of 2.5 eV or more, preferably 3.0 eV or more, and most preferably 3.5 eV or more. One method of calculating the band gap uses the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

[0127] Molecular orbitals, especially the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), their energy levels and the energy of the lowest triplet state T1 or the lowest excited singlet state S1 of the material are determined using quantum chemical calculations. To calculate the organic material, a structure optimization is first performed using the "ground state / semi-empirical / initial spin / AM1 / charge 0 / spin singlet" method. Then, energy calculations are performed based on the optimized structure. Here, the "TD-SCF / DFT / initial spin / B3PW91" method is used with the "6-31G(d)" basis set (charge 0, spin singlet). The HOMO energy level HEh or the LUMO energy level LEh is obtained in Hartree units from the energy calculation. This is used to determine the HOMO and LUMO energy levels in electron volts by calibrating with cyclic voltammetry measurements as follows: HOMO(eV)=((HEh*27.212)-0.9899) / 1.1206 LUMO(eV)=((LEh*27.212)-2.0041) / 1.385 In the context of the present invention, these values ​​are considered to be the HOMO and LUMO energy levels of the material.

[0128] The lowest triplet state T1 is defined as the energy of the triplet state with the lowest energy evident from the quantum chemical calculations given.

[0129] The lowest excited singlet state S1 is defined as the energy of the excited singlet state with the lowest energy evident from the described quantum chemical calculations.

[0130] The method described here is independent of the software package used and will always give the same results. Examples of programs frequently used for this purpose are "Gaussian09W" (Gaussian) and Q-Chem4.1 (Q-Chem).

[0131] The present invention further provides a composition comprising at least one compound comprising at least one structure of formula (I) or the preferred forms described above and below, and at least one phosphorescent emitter, where the term "phosphorescent emitter" is also understood to mean phosphorescent dopant.

[0132] In a system comprising a matrix material and a dopant, the dopant is understood to mean the component which has the smaller proportion in the mixture. Correspondingly, in a system comprising a matrix material and a dopant, the matrix material is understood to mean the component which has the greater proportion in the mixture.

[0133] Preferred phosphorescent dopants for use in the matrix system, preferably the mixed matrix system, are the preferred phosphorescent dopants specified below.

[0134] The term "phosphorescent dopant" typically encompasses compounds in which emission occurs via a spin-forbidden transition, such as from an excited triplet state, or a state with a higher spin quantum number, such as a quintet state.

[0135] Suitable phosphorescent compounds (=triplet emitters) are compounds that emit light, preferably in the visible range, when appropriately excited, and furthermore contain at least one atom with atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, in particular a metal with this atomic number. The phosphorescent emitters used are preferably compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum. In the context of the present invention, all luminescent compounds containing the above metals are considered as phosphorescent compounds.

[0136] Examples of the above-mentioned illuminants are described in WO00 / 70655, WO2001 / 41512, WO2002 / 02714, WO2002 / 15645, EP1191613, EP1191612, EP1191614, WO05 / 033244, WO05 / 019373, US2005 / 0258742, WO2009 / 146770, WO2010 / 015307, WO2010 / 031485, WO2010 / 054731, WO2010 / 054728, WO2010 / 086089, WO2010 / 099852, WO20

[0023] Applications including WO2010 / 102709, WO2011 / 032626, WO2011 / 066898, WO2011 / 157339, WO2012 / 007086, WO2014 / 008982, WO2014 / 023377, WO2014 / 094961, WO2014 / 094960, WO2014 / 094960, WO2016 / 124304, WO2016 / 015815, WO2016 / 000803, WO2015117718, WO2015104045 and WO2015036074. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as further known to those skilled in the art in the field of organic electroluminescent devices are suitable, and those skilled in the art can use further phosphorescent complexes without inventive ingenuity.

[0137] Explicit examples of phosphorescent dopants are given in the table below: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0138] In a particular embodiment of the invention, the compounds of the invention can be used as hole blocking materials, preferably in a hole blocking layer, in which case the compounds of the invention used as hole blocking materials comprise at least one electron transport group. In a preferred embodiment, the compounds of the invention used as hole blocking materials comprise fewer hole transport groups than electron transport groups, more preferably no hole transport groups.

[0139] Furthermore, the compounds of the present invention are used as electron or exciton blocking materials, preferably in an electron or exciton blocking layer, in which case the compounds of the present invention used as electron or exciton blocking materials comprise at least one hole transporting group. In a preferred embodiment, the compounds of the present invention used as electron or exciton blocking materials comprise fewer electron transporting groups than hole transporting groups, more preferably no electron transporting groups, which may be the case, as described above or below, for R of formula (QL). a or R radical.

[0140] The above-mentioned compound comprising the structure of formula (I) or the preferred form detailed above can be preferably used as an active component in an electronic device. An electronic device is understood to be a device comprising an anode, a cathode, and at least one layer between the anode and the cathode, said layer comprising at least one organic or organometallic compound. Thus, the electronic device of the present invention comprises an anode, a cathode, and an intermediate layer comprising at least one compound comprising the structure of formula (I).

[0141] Preferred electronic devices here are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), organic electrical sensors, light emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasmonic light emitting devices (DM Koller et al., Nature Pho~nics 2008, 1-4), preferably organic electroluminescent devices (OLEDs, PLEDs), in particular phosphorescent OLEDs containing at least one compound comprising the structure of formula (I). Particularly preferred are organic electroluminescent devices. Active components are generally organic or inorganic materials introduced between the anode and the cathode, such as charge injecting, charge transporting or charge blocking materials, but especially light emitting materials and matrix materials.

[0142] A preferred embodiment of the present invention is an organic electroluminescent device. The organic electroluminescent device comprises an anode, a cathode and at least one light-emitting layer. In addition to these layers, the organic electroluminescent device may also comprise further layers, for example, in each case, 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 generating layers and / or organic or inorganic p / n junctions. In this case, one or more hole transport layers can be p-doped, for example, with metal oxides such as MoO3 or WO3, or with electron-deficient (per)fluorinated aromatic systems, and / or one or more electron transport layers can be n-doped. Similarly, an intermediate layer, which has, for example, an exciton blocking function and / or controls the charge balance in the organic electroluminescent device, may be introduced between the two light-emitting layers. However, it should be noted that each of these layers does not necessarily have to be present.

[0143] Here, the organic electroluminescent element may comprise one light-emitting layer or may comprise multiple light-emitting layers. If multiple light-emitting layers are present, they preferably have multiple emission maxima over the entire range from 380 nm to 750 nm, so as to produce white light overall, i.e., various light-emitting compounds capable of emitting fluorescence or phosphorescence are used in the light-emitting layers. Particularly preferred are three-layer systems (for basic structures, see, for example, WO2005 / 011013) in which the three layers emit blue, green and orange or red light, or systems with three or more light-emitting layers. The system may be a hybrid structure in which one or more layers emit fluorescence and one or more other layers emit phosphorescence.

[0144] In a preferred embodiment of the present invention, the organic electroluminescent device comprises the compound of the present invention comprising the structure of formula (I) or of the preferred forms detailed above as a matrix material, preferably as an electron-conducting matrix material, in one or more light-emitting layers, preferably in combination with a further matrix material, preferably a hole-conducting matrix material. The light-emitting layer comprises at least one light-emitting compound. In a further preferred embodiment, the further matrix material is a compound with a large band gap that is not involved or is not involved to a significant extent in the hole and electron transport in the layer. In a further preferred embodiment of the present invention, the compound of the present invention comprising the structure of formula (I) or of the preferred forms detailed above is present as a matrix material, preferably as a hole-conducting matrix material, in one or more light-emitting layers, preferably in combination with a further matrix material, preferably an electron-conducting matrix material.

[0145] Suitable matrix materials which can be used in combination with the compounds of formula (I) or according to the preferred embodiments are aromatic ketones; aromatic phosphine oxides; or aromatic sulfoxides or sulfones (for example according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680); triarylamines, in particular monoamines (for example according to WO 2014 / 015935); carbazole derivatives (for example CBP (N,N-biscarbazolylbiphenyl) or W carbazole derivatives as disclosed in US2005 / 039246, US2005 / 0069729, JP2004 / 288381, EP1205527, or WO2008 / 086851; indolocarbazole derivatives (for example according to WO2007 / 063754 or WO2008 / 056746); indenocarbazole derivatives (for example according to WO2010 / 136109 and WO2011 / 000455); azacarbazole derivatives (for example according to EP1617710, EP1617711, EP1731584, JP20 05 / 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. according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746); zinc complexes (e.g. according to EP 652273 or WO 2009 / 062578); diazasilol or tetraazasilol derivatives (e.g. according to diazaphosphole derivatives (for example according to WO2010 / 054730); bridged carbazole derivatives (for example according to US2009 / 0136779, WO2010 / 050778, WO2011 / 042107, WO2011 / 088877 or WO2012 / 143080); triphenylene derivatives (for example according to WO2012 / 048781); lactams (for example according to WO2011 / 116865, WO2011 / 137951 or WO2013 / 064206);Or 4-spirocarbazole derivatives (for example according to WO2014 / 094963 or unpublished application EP14002104.9). It is also possible for further phosphorescent emitters, which emit at shorter wavelengths than the actual emitter, to be present in the mixture as co-hosts;

[0146] Preferred co-host materials are triarylamine derivatives, especially monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams, and carbazole derivatives.

[0147] Preferred triarylamine derivatives to be used as co-host materials together with the compounds of the present invention are selected from the compounds of the following formula (TA-1): [ka] Here, Ar 1 are identical or different at each occurrence, have 6 to 40 carbon atoms, and in each case, one or more R 2 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 60 aromatic ring atoms and in each case one or more R 2 an aryloxy group, optionally substituted by a radical, or an aryloxy group having 5 to 60 aromatic ring atoms and, in each case, one or more R 2 an aralkyl group optionally substituted by a radical, where two or more adjacent R 2 The substituents are optionally monocyclic or polycyclic, aliphatic, heteroaromatic, aromatic or heteroaromatic ring systems, preferably monocyclic or polycyclic aliphatic ring systems (which may be one or more R 3 radical), where the symbol R 2 has the meaning given above, especially in formula (I). 1 are identical or different at each occurrence and have 5 to 24, preferably 5 to 12, aromatic ring atoms, and in each case one or more R 2The radical is an aryl or heteroaryl group which may be substituted, but is preferably unsubstituted.

[0148] Preferred Ar 1 Exemplary groups are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which may be selected from the group consisting of one or more R 2 The radicals may be substituted, but are preferably unsubstituted.

[0149] Preferably, Ar 1 The groups may be the same or different at each occurrence and are defined as R 1 -1~R 1 -177 group, more preferably R 1 -1~R 1 -64, -64.

[0150] In a preferred embodiment of the compound represented by formula (TA-1), at least one Ar 1 The group is selected from the group consisting of biphenyl groups, which may be ortho-, meta- or para-biphenyl groups. In a further preferred embodiment of the compound of formula (TA-1), at least one Ar 1 The group is selected from a fluorene group or a spirobifluorene group, where these groups may be bonded to the nitrogen atom in the 1-, 2-, 3- or 4-position, respectively. In an even more preferred embodiment of the compound of formula (TA-1), at least one group Ar 1is selected from a phenylene or biphenyl group which is an ortho-, meta- or para-bonded group and is substituted by a dibenzofuran, benzothiophene or carbazole group, in particular a dibenzofuran group, where the dibenzofuran or benzothiophene group is bonded to the phenylene or biphenyl group via the 1-, 2-, 3- or 4-position and where the carbazole group is bonded to the phenylene or biphenyl group via the 1-, 2-, 3- or 4-position or via a nitrogen atom.

[0151] In a particularly preferred embodiment of the compound of formula (TA-1), one Ar 1 The radical is selected from fluorene or spirobifluorene radicals, in particular from 4-fluorene or 4-spirobifluorene radicals, and one Ar 1 The group is selected from a biphenyl group, in particular a para-biphenyl group, or a fluorene group, in particular a 2-fluorene group, and a third Ar 1 The radicals are selected from para-phenylene or para-biphenyl radicals substituted with a dibenzofuran radical, in particular a 4-dibenzofuran radical, or with a carbazole radical, in particular an N-carbazole radical or a 3-carbazole radical.

[0152] In a preferred embodiment, the co-host material is a carbazole compound, and it is particularly preferred if the carbazole compound is a biscarbazole or tricarbazole compound, and it is highly preferred if the carbazole compound is selected from the following structures: [ka] [ka]

[0153] Preferred indenocarbazole derivatives to be used as co-host materials with the compounds of the present invention are selected from the compounds of formula (TA-2): [ka] Here, Ar 1 and R 1 has the meaning given above, especially in formulae (I) and (TA-1). 1 A preferred form of the group is the structure (R 1 -1)~(R 1 -177), more preferably R 1 -1~R 1 -64.

[0154] A preferred embodiment of the compound of formula (TA-2) is the compound of formula (TA-2a) below: [ka] Here, Ar 1 and R 1 has the meaning given above, in particular in formula (I) and / or (TA-1), in which the two R 1 The radicals are preferably, identical or different, alkyl radicals having 1 to 4 carbon atoms, in particular a methyl radical, or an aromatic ring system having 6 to 12 carbon atoms, in particular a phenyl radical. More preferably, the two R 1 More preferably, the R bonded to the indenocarbazole basic skeleton in formula (TA-2a) is a methyl group. 1 The substituents are H or a carbazole group which can be bonded to the indenocarbazole base skeleton via the 1-, 2-, 3- or 4-position or via a nitrogen atom, in particular via the 3-position.

[0155] Further preferred indenocarbazoles as co-hosts are disclosed in WO2010 / 136109 and WO2013 / 041176.

[0156] Preferred 4-spirocarbazole derivatives to be used as co-host materials with the compounds of the present invention are selected from the compounds of formula (TA-3): [ka] Here, Ar 1 and R 1 has the meaning given above, in particular in formulae (I), (II) and / or (Q-1). 1 A preferred form of the group is the structure (R 1 -1)~(R 1 -177), more preferably R 1 -1~R 1 -64.

[0157] A preferred form of the compound of formula (TA-3) is the compound of formula (TA-3a): [ka] Here, Ar 1 and R 1 has the meaning given above, in particular in formulae (I), (II) and / or (Q-1). 1 A preferred form of the group is the structure (R 1 -1)~(R 1 -177), more preferably R 1 -1~R 1 -64.

[0158] Preferred co-host materials contain a carbazole group as well as a triazine group, and it is particularly preferred when the two groups are formed by a dibenzofuran or dibenzothiophene bridge. Very particularly preferred co-host materials having triazine-dibenzofuran / dibenzothiophene-carbazole structural units are disclosed in WO2015 / 169412.

[0159] Preferred lactams for use as co-host materials with the compounds of the present invention are selected from compounds of formula (LAC-1): [ka] Here, R 1 has the meaning given above, especially in formula (I).

[0160] A preferred form of the compound of formula (LAC-1) is the compound of formula (LAC-1a): [ka] Here, R 1 has the meaning given above, especially in formula (I), where R 1 is preferably identical or different at each occurrence and is H or has 5 to 40 aromatic ring atoms and one or more radicals R 2 an aromatic or heteroaromatic ring system, optionally substituted with R 2 has the meaning given above, in particular in formula (I). Most preferably, R 1 The substituents are selected from H and 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, each of which is substituted with one or more non-aromatic radicals R 2 The appropriate R is selected from the group consisting of aromatic or heteroaromatic ring systems, which may be substituted, but are preferably unsubstituted. 1 Examples of substituents are phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaternary phenyl, especially branched quaternary phenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl (each of which may be selected from the group consisting of one or more R 2 wherein the preferred structure R 1 R-1 to R-177, more preferably R 1 -1~R 1 The structure is the same as that shown for -64.

[0161] It is also preferred to use mixtures of different matrix materials, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material, as well as mixtures of charge-transporting matrix materials with electrically inactive matrix materials which are not involved to any significant extent, if at all, in the charge transport, as described, for example, in WO 2010 / 108579.

[0162] Furthermore, the use of a mixture of two or more triplet emitters and matrices is preferred, where a triplet emitter with a shorter wavelength emission spectrum acts as a co-matrix for a triplet emitter with a longer wavelength emission spectrum.

[0163] More preferably, the compounds of the present invention comprising the structure of formula (I) in a preferred form can be used as a matrix material in an organic electronic device, in particular an organic electroluminescent device, such as an OLED or an OLEC, in an emitting layer, in which the matrix material comprising the structure of formula (I) or the preferred forms described above and below is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

[0164] In this case, the ratio of the matrix material in the light-emitting layer is 50.0 to 99.9 volume %, preferably 80.0 to 99.5 volume %, and more preferably 92.0 to 99.5 volume % for the fluorescent-emitting layer, and 85.0 to 97.0 volume % for the phosphorescent-emitting layer.

[0165] Correspondingly, the proportion of the dopant is 0.1 to 50.0 volume %, preferably 0.5 to 20.0 volume %, and more preferably 0.5 to 8.0 volume % for the fluorescent-emitting layer, and 3.0 to 15.0 volume % for the phosphorescent-emitting layer.

[0166] The light-emitting layer of the organic electroluminescent device may also be a system that contains several matrix materials (mixed matrix system) and / or several dopants. In this case, too, the dopant is generally the material that has a smaller proportion in the system, and the matrix material is the material that has a larger proportion in the system. However, in individual cases, the proportion of a single matrix material in the system may be smaller than the proportion of a single dopant.

[0167] In a further preferred embodiment of the invention, the compound comprising the structure of formula (I) or the preferred embodiments described above and below is used as one component of a mixed matrix system. The mixed matrix system preferably comprises two or three different matrix materials, more preferably two different matrix materials. In this case, it is preferred that one of the two materials is a material with hole transport properties and the other material is a material with electron transport properties. However, the desired electron transport and hole transport properties of the mixed matrix component may also be mainly or completely incorporated in a single mixed matrix component, in which case the further mixed matrix component(s) fulfills the other function. The two different matrix materials may be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1 and most preferably 1:4 to 1:1. It is preferred to use the mixed matrix system in a phosphorescent organic electroluminescent device. More detailed information on the mixed matrix system is given, inter alia, in application WO2010 / 108579.

[0168] The present invention further provides an electronic device, preferably an organic electroluminescent device, comprising, as hole-conducting compound in one or more hole-conducting layers, one or more of the compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention.

[0169] In a preferred embodiment of the present invention, the organic electroluminescent device comprises an inventive compound having the structure of formula (I) or the preferred embodiments described above, and / or at least one inventive oligomer, polymer or dendrimer, as electron-conducting compound in the electron-conducting layer.

[0170] The present invention further provides an electronic device, preferably an organic electroluminescent device, comprising one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more electron transport layers, preferably in combination with a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention with a material having a high dielectric constant, for example an alkali metal or alkaline earth metal fluoride, the corresponding oxide or carbohydrate, for example LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc., or an organic alkali metal complex, for example Liq (lithium quinolinate), particularly preferably an organic alkali metal complex, preferably Liq). The two different materials in the electron transport layer may here be present in a ratio of 1:50 to 50:1, preferably 1:10 to 10:1, more preferably 1:4 to 4:1, most preferably 1:2 to 2:1.

[0171] The present invention further provides an electronic device, preferably an organic electroluminescent device, comprising one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in an emitting layer as matrix material, preferably in combination with a phosphorescent emitter.

[0172] The cathode is preferably a metal, metal alloy or multilayer structure composed of various metals, such as alkaline earth metals, alkali metals, metals of the main group or lanthanides (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.), having a low work function. Also suitable are alloys composed of alkali metals or alkaline earth metals and silver, for example alloys composed of magnesium and silver. In the case of multilayer structures, in addition to the metals, further metals with a relatively high work function, such as Ag, can also be used, in which case combinations of metals such as Mg / Ag, Ca / Ag or Ba / Ag are commonly used. Also, a thin intermediate layer, preferably composed of a material with a high dielectric constant, can be introduced between the metal cathode and the organic semiconductor. Examples of suitable materials for this purpose are fluorides of alkali metals or alkaline earth metals, and also the corresponding oxides or carbonates (e.g. LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Also useful for this purpose are organic alkali metal complexes, such as Liq (lithium quinolinate).The layer thickness of this layer is preferably 0.5 to 5 nm.

[0173] The anode is preferably a material with a high work function. The anode preferably has a work function greater than 4.5 eV against vacuum. Firstly, metals with high redox potential, such as Ag, Pt or Au, are suitable for this purpose. Secondly, metal / metal oxide electrodes (e.g. Al / Ni / NiOx, Al / P~x) are also preferred. For some applications, at least one electrode must be transparent or partially transparent to allow either the irradiation of the organic material (O-SC) or the emission of light (OLED / PLED, O-laser). Here, preferred anode materials are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Furthermore, preferred are doped conductive organic materials, in particular doped conductive polymers, such as PEDOT, PANI or derivatives of these polymers. It is further preferred when a p-type doped hole transport material is applied to the anode as a hole injection layer, in which case suitable p-dopants are metal oxides, such as MoO3 or WO3, or electron-deficient (per)fluorinated aromatic systems. Further suitable p-dopants are HAT-CN (hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection into materials with a low HOMO, i.e. a large HOMO in magnitude.

[0174] In the further layers, any material used in the prior art for such layers can generally be used, and the skilled person can combine any of these materials with the materials according to the invention in an electronic device without inventive ingenuity.

[0175] Since the service life of such components is significantly shortened by the presence of water and / or air, the components are accordingly structured (depending on the application), provided with contacts and finally hermetically sealed.

[0176] Further preferred are electronic devices, in particular organic electroluminescent devices, characterized in that one or more layers are applied by sublimation. -5 Less than millibars, preferably 10 -6 It is applied by vacuum deposition in a vacuum sublimation system at an initial pressure of less than mbar. The initial pressure can be lower or higher, for example 10 -7 Submillibars are also possible.

[0177] Also preferred are electronic devices, in particular organic electroluminescent devices, characterized in that one or more layers are applied by the OVPD (organic vapor phase deposition) method or by means of sublimation of a carrier gas. -5 It is applied at pressures of mbar to 1 bar. A special case of this method is the OVJP (Organic Vapor Jet Printing) method, in which the material is applied directly through a nozzle and further structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0178] Further preferred are electronic devices, in particular organic electroluminescent devices, characterized in that one or more layers are produced from solution, for example by spin coating or by any printing method, for example by screen printing, flexographic printing, offset printing or nozzle printing, but more preferably by LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds are required, which can be obtained, for example, by suitable substitution.

[0179] Electronic devices, in particular organic electroluminescent devices, can also be produced as hybrid systems by coating one or more layers from solution and one or more other layers by vacuum deposition, for example an emissive layer comprising a compound of formula (I) and a matrix material can be coated from solution and thereto a hole blocking layer and / or an electron transporting layer can be coated by vacuum deposition under reduced pressure.

[0180] These methods are generally known to those skilled in the art and can be readily applied to electronic devices, particularly organic electroluminescent devices, comprising compounds of formula (I) or the preferred forms detailed above.

[0181] The electronic devices, in particular organic electroluminescent devices, of the present invention are notable for one or more of the following surprising advantages over the prior art: 1. Electronic devices, especially organic electroluminescent devices, comprising compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below, especially as host materials or electron conducting materials and / or hole conducting materials, have very good lifetimes.In this context, these compounds provide particularly low roll-off, i.e. a small decrease in the power efficiency of the device at high luminance. 2. The electronic device, particularly the organic electroluminescent device, comprising the compound, oligomer, polymer or dendrimer having the structure of formula (I) or the preferred forms described above and below as an electron conducting material and / or host material has excellent efficiency.In this context, the compound, oligomer, polymer or dendrimer of the present invention having the structure of formula (I) or the preferred forms described above or below provides low operating voltage when used in the electronic device. 3. The compounds, oligomers, polymers or dendrimers of the invention having the structure of formula (I) or the preferred forms described above and below, exhibit very high stability and longevity. 4. The use of compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below makes it possible to avoid the formation of light loss channels in electronic devices, in particular in organic electroluminescent devices, so that these devices are characterized by high PL efficiency and thus high EL efficiency of the emitter, as well as good energy conduction from the matrix to the dopant. 5. The use of compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below in layers of electronic devices, in particular organic electroluminescent devices, results in high mobility of electronically conductive structures. 6. Compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below are characterized by excellent thermal stability, and compounds having a molecular weight of less than about 1200 g / mol have good sublimability. 7. The compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below have excellent glass film forming properties. 8. Compounds, oligomers, polymers or dendrimers having the structure of formula (I) or the preferred forms described above and below form very good films from solution. 9. The compounds, oligomers, polymers or dendrimers comprising the structure of formula (I) or the preferred forms described above and below have a surprisingly high triplet level T1.

[0182] These above mentioned advantages are not accompanied by degradation of other electronic properties.

[0183] The compounds and mixtures of the present invention are suitable for use in electronic devices. Electronic devices are understood to mean devices that contain at least one layer that contains at least one organic compound. Devices may also contain layers that contain inorganic materials or are entirely made of inorganic materials.

[0184] The present invention therefore provides the use of the compounds or mixtures according to the invention in electronic devices, in particular organic electroluminescent devices.

[0185] The present invention further provides the use of the compounds of the invention and / or the oligomers, polymers or dendrimers of the invention as host materials for phosphorescent emitters, electron transport materials and / or hole transport materials in electronic devices, preferably as host materials for red or green phosphorescent emitting compounds or as electron transport materials together with fluorescent emitters in organic electroluminescent devices.

[0186] The present invention further provides the use of the compounds of the invention and / or the oligomers, polymers or dendrimers of the invention as part of an electron transport layer in an electronic device, in particular in combination with a material having a high dielectric constant.

[0187] The present invention further provides an electronic device comprising at least one of the compounds or mixtures of the present invention as shown above. In this case, the preferred compounds as described above are also applied to the electronic device. More preferably, the electronic device is selected from the group consisting of organic electroluminescent devices (OLED, PLED), organic integrated circuits (O-IC), organic field effect transistors (O-FET), organic thin film transistors (O-TFT), organic light emitting transistors (O-LET), organic solar cells (O-SC), organic photodetectors, organic photoreceptors, organic field quenching devices (O-FQD), organic electric sensors, light emitting electrochemical cells (LEC), organic laser diodes (O-laser), and organic plasmonic light emitting devices (DMKoller et al., Nature Pho~nics 2008, 1-4), preferably organic electroluminescent devices (OLED, PLED), in particular phosphorescent OLED.

[0188] In a further embodiment of the present invention, the organic electroluminescent device of the present invention does not include a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, which means that the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO2005 / 053051.Furthermore, the same or similar metal complex as the metal complex in the light-emitting layer can also be used as a hole transport or hole injection material directly adjacent to the light-emitting layer, as described, for example, in WO2009 / 030981.

[0189] In the further layer of the organic electroluminescent device of the present invention, any material as is commonly used according to the prior art can be used.Therefore, those skilled in the art can use any material known for organic electroluminescent devices in combination with the compound of the present invention according to formula (I) or preferred form without inventive ingenuity.

[0190] The compounds of the invention generally have very good properties when used in organic electroluminescent devices.In particular, when the compounds of the invention are used in organic electroluminescent devices, the lifetime is significantly better than that of similar compounds according to the prior art.At the same time, other properties of organic electroluminescent devices, especially efficiency and voltage, are also better or at least comparable.

[0191] It should be noted that variations of the embodiments described in the present invention are included within the scope of the present invention. Each feature disclosed in the present invention may be replaced with an alternative feature that fulfills the same purpose or an equivalent or similar purpose, unless this is explicitly excluded. Therefore, each feature disclosed in the present invention should be considered as an example of a general series, or an equivalent or similar feature, unless otherwise specified.

[0192] All features of the present invention can be combined with one another in any way, unless the particular features and / or steps are mutually exclusive. This is particularly true for the preferred features of the present invention. Similarly, features of non-essential combinations can be used separately (and not in combination).

[0193] It should be noted that many features, and in particular features of the preferred forms of the invention, should be considered as inventive in their own right and not merely as part of the forms of the invention, and that independent protection can be sought for these features in addition to or instead of the invention presently claimed.

[0194] The technical teachings disclosed with the present invention may be abstracted and combined with other embodiments.

[0195] The present invention will now be described in more detail with reference to the following examples, without however limiting the invention thereto.

[0196] Using the following detailed description, one skilled in the art can, without inventive elaboration, further manufacture the electronic device of the present invention and thereby practice the present invention throughout the scope of the claims.

[0197] Working Example The following syntheses are carried out under a protective gas atmosphere in dry solvents unless otherwise stated. The reactants are commercially available from ALDRICH. The numbers of the reactants known from the literature (some of these are shown in square brackets) are the corresponding CAS numbers. Synthesis Example [ka]

[0198] Synthesis Example a) 1-Bromo-4b,9-diazaindeno[1,2-a]inden-10-one [ka] In a 2 liter flask, 89.0 g (754 mmol; 1.50 equiv.) of benzimidazole [CAS 51-17-2], 102 g (502 mmol; 1.00 equiv.) of 2-bromo-6-fluorobenzoaldehyde [CAS 360575-28-6] and 108 g (778 mmol; 1.55 equiv.) of potassium carbonate [CAS 584-08-7] are suspended in 1500 ml of DMSO [CAS 67-68-5]. The reaction mixture is stirred for 18 hours at 105° C. while introducing air. After cooling to room temperature, the reaction is poured onto 2.5 liters of ice water. The precipitated solid is filtered and washed with ethyl acetate [CAS 141-78-6]. 43.3 g (144.7 mmol, 29% of theory) of product is obtained as an orange solid.

[0199] In a similar manner, the following compounds can be obtained: [ka]

[0200] b) 10-(4'-chlorobiphenyl-2-yl)-10H-4b,9-diazaindeno[1,2-a]inden-10-ol [ka] In a 1 liter flask, under protective gas, 20.9 g (78.2 mmol; 1.07 equiv.) of 2-bromo-4'-chlorobiphenyl [CAS 179526-95-5] is dissolved in 50 ml of dry THF [CAS 109-99-9] and cooled to -78 ° C. Then, 30.7 ml (2.5 mol / l; 76.7 mmol; 1.05 equiv.) of n-butyllithium [CAS 109-72-8] is added dropwise and the mixture is stirred for another 2 hours. A suspension of 16.1 g (73.0 mmol, 1.00 equiv.) of 4b,9-diazaindeno[1,2-a]inden-10-one [CAS 138479-49-9] in 370 ml of dry THF [CAS 109-99-9] is added dropwise to this mixture. The resulting mixture is allowed to warm slowly to room temperature and stirred for an additional 18 hours.

[0201] The reaction is stopped by adding 300 ml of water and the remaining phases are separated. The aqueous phase is extracted with ethyl acetate (3x150 ml) [CAS141-78-6] and the combined organic phases are washed with water (2x150 ml). The solvent is removed under reduced pressure to give the crude product, which is finally dissolved in dichloromethane [CAS75-09-2] and precipitated by adding heptane. After filtration, 25.3 g (61.8 mmol; 85%) of the product can be obtained as a brown filter residue.

[0202] In a similar manner, the following compounds can be obtained: [ka]

[0203] c) 2-chlorospiro[fluorene-9,11'-indolo[1,2-a]benzimidazole] [ka] In a 500 ml flask, 24.9 g (60.9 mmol; 1.00 equiv.) of 10-(4'-chlorobiphenyl-2-yl)-10H-4b,9-diazaindeno[1,2-a]inden-10-ol and 116 g (609 mmol; 10.0 equiv.) of toluenesulfonic acid monohydrate [CAS6192-52-5] are suspended in 290 ml of toluene [CAS108-88-3] and the mixture is stirred at 115°C for 72 hours. Once the conversion is complete, the mixture is cooled to room temperature and the reaction solution is concentrated. The crude product is taken up in ethyl acetate (500 ml) [CAS141-78-6] and washed with water (2x250 ml). After filtration through silica gel and precipitation with heptane, 19.1 g (80%, 48.8 mmol) of product are obtained in the form of a beige solid.

[0204] In a similar manner, the following compounds can be obtained: [ka]

[0205] d) 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,11'-indolo[1,2-a]benzimidazole] [ka] In a 1 L flask, under protective gas, 18.6 g (47.5 mmol; 1.00 equiv.) of 2-chlorospiro[fluorene-9,11'-indolo[1,2-a]benzimidazole] and 14.5 g (57 mmol, 1.20 equiv.) of bis(pinacolato)diborane [CAS 73183-34-3] are dissolved in 450 ml of dry dioxane [CAS 123-91-1] and the mixture is degassed for 30 min. Subsequently, 10.2 g (105 mmol, 2.20 equiv.) of potassium acetate [CAS 127-08-2] and 1.76 g (2.38 mmol, 5 mol%) of trans-dichlorobis(tricyclohexylphosphine)palladium(II) complex [CAS 29934-17-6] are added and the mixture is heated to 90 ° C overnight. After the reaction is complete, the mixture is diluted with 300 ml of toluene [CAS 108-88-3] and extracted with water. The solvent is removed on a rotary evaporator and the resulting solid is dried. 17.9 g of product (37.1 mmol, 78% of theory) is converted without further purification.

[0206] In a similar manner, the following compounds can be obtained: [ka]

[0207] e) 10,10-dimethyl-1,8-diazatetracyclo[7.7.0.0 2,7 .0 11,16 ]Hexadeca-2,4,6,8,11(16),12,14-heptane [ka] Under an inert atmosphere, 147 g (774 mmol, 4.00 equiv.) of titanium(IV) chloride [CAS 7550-45-0] and dichloromethane [CAS 75-09-2] are initially charged at -40 °C. Then, 387 ml (2 mol / l, 774 mmol, 4.00 equiv.) of dimethylzinc solution [CAS 544-97-8] are added at such a rate that the temperature does not exceed -35 °C. Then, 42.6 g (193.6 mmol, 1.00 equiv.) of 4b,9-diazaindeno[1,2-a]inden-10-one are added. The resulting solution is slowly warmed to room temperature and quenched by the addition of ethanol and then water. The phases are separated and the organic phase is concentrated to a solid. The crude product is repeatedly recrystallized from a mixture of heptane [CAS 142-82-5] and ethyl acetate [CAS 141-78-6]. 5.03 g (21.3 mmol, 11% of theory) of product are obtained.

[0208] f) 5-bromo-10,10-dimethyl-1,8-diazatetracyclo[7.7.0.0 2,7 .0 11,16 ]Hexadeca-2,4,6,8,11(16),12,14-heptane [ka] Under protective gas, 4.83 g (20.6 mmol, 1.00 eq.) of 3-[3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl]-9-(triphenylen-2-yl)-9H-carbazole are suspended in 30 ml of dry DMF [CAS68-12-2] and cooled to 0° C. Then, 4.03 g (22.7 mmol, 1.1 eq.) of NBS [CAS128-08-5] are added and the reaction mixture is stirred for 16 hours while warming to room temperature. The reaction is terminated by the addition of 150 ml of water and stirred for 30 minutes. After filtration and drying, 5.48 g (17.5 mmol; 85% of theory) of product can be obtained.

[0209] g) N-(9,9-dimethylfluoren-4-yl)-N-(4-phenylphenyl)spiro[fluorene-9,11'-indolo[1,2-a]benzimidazol]-2-amine [ka] An initial charge of 15.2 g (38.9 mmol; 1.00 equiv.) of 2-chlorospiro[fluorene-9,11'-indolo[1,2-a]benzimidazole], 14.5 g (39.3 mmol; 1.01 equiv.) of biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-4-yl)amine [CAS 1421789-16-3] and 4.96 g (42.7 mmol; 1.10 equiv.) of sodium tert-pentoxide [CAS 14593-46-5] in 200 ml of toluene [CAS 108-88-3] is inactivated in argon steam for 30 minutes. Then 479 mg (1.17 mmol; 3 mol%) of dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6], 262 mg (1.17 mmol; 3 mol%) of palladium acetate [CAS 3375-31-3] are added and the mixture is heated to reflux for 18 hours. After completion of the conversion and cooling to room temperature, 500 ml of water are added to the reaction. After phase separation and extraction of the aqueous phase with toluene [CAS 108-88-3], the combined organic phase is concentrated and heptane is added. The precipitated solid is separated. Purification by Soxhlet extraction, recrystallization and vacuum evaporation gives the desired product (6.63 g; 9.26 mmol; 24% of theory).

[0210] In a similar manner, the following compounds can be obtained: [ka] [ka]

[0211] h) 2-[9-phenyl-6-(9-phenylcarbazol-3-yl)carbazol-3-yl]spiro[fluorene-9,11'-indolo[1,2-a]benzimidazole] [ka] 6.36 g (16.3 mmol; 1.00 equiv.) of 2-chlorospiro[fluorene-9,11'-indolo[1,2-a]benzimidazole], 11.4 g (18.7 mmol; 1.15 equiv.) of 9,9'-diphenyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H,9'H-[3,3']biscarbazolyl [CAS 1572537-61-1] and 7.49 g (32.5 mmol; 2.00 equiv.) of tripotassium phosphate [CAS 14593-46-5] are suspended in 210 ml of toluene [CAS 108-88-3] and 20 ml of water. To this suspension, 334 mg (814 μmol; 5 mol%) of dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6] and 183 mg (814 μmol; 5 mol%) of palladium acetate [CAS 3375-31-3] are added and the reaction mixture is heated under reflux for 16 hours. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 150 ml of water and then concentrated to dryness. The residue is recrystallized from toluene and finally sublimed under high vacuum. The residue is recrystallized from toluene and finally sublimed under high vacuum. The yield is 4.70 g (5.60 mmol, 34% of theory).

[0212] In a similar manner, the following compounds can be obtained: [ka] [ka]

[0213] i) 2-(4,6-diphenyl-1,3,5-triazin-2-yl)spiro[fluorene-9,11'-indolo[1,2-a]benzimidazole] [ka] 10.8 g (22.4 mmol; 1,20 equiv.) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,11'-indolo[1,2-a]benzimidazole], 5.00 g (18.7 mmol; 1.00 equiv.) of 2-chloro-4,6-diphenyl-[1,3,5]triazine and 8.58 g (39.2 mmol; 2.10 equiv.) of potassium phosphate tripotassium phosphate [CAS14593-46-5] are suspended in 45 ml of toluene [CAS108-88-3], 45 ml of dioxane [CAS123-91-1] and 45 ml of water. To this suspension, 383 mg (934 μmol; 5 mol%) of dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6], 210 mg (934 μmol; 5 mol%) of palladium acetate [CAS 3375-31-3] are added and the reaction mixture is heated under reflux for 16 hours. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 500 ml of water and concentrated to dryness. The residue is recrystallized from toluene [CAS 108-88-3] and finally sublimed under high vacuum. The yield is 5.32 g (9.05 mmol, 48% of theory).

[0214] In a similar manner, the following compounds can be obtained: [ka] [ka]

[0215] OLED manufacturing Examples I1 to I12 below (see Table 1) demonstrate the use of the materials of the invention in OLEDs.

[0216] The pretreatment of the glass substrates of examples I1 to I12 coated with a 50 nm thick structured ITO (indium tin oxide) is carried out using oxygen plasma before coating, followed by argon plasma. These plasma-treated glass substrates form the substrates on which the OLEDs are applied.

[0217] An OLED basically has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emissive layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL) and finally a cathode. The cathode is formed of an aluminum layer with a thickness of 100 nm. The exact structure of the OLED can be found in Table 1. The materials required for the manufacture of the OLED are shown in Table 2. The data of the OLED is shown in Table 3.

[0218] All materials are applied by thermal evaporation in a vacuum chamber. In this case, the light-emitting layer always consists of at least one matrix material (host material) and a light-emitting dopant (emitter) that is mixed in a certain volume percentage into the matrix material(s) by co-evaporation. A specification such as EG1:IC2:TEG1 (49%:44%:7%) means here that the material EG1 is present in the layer in a volume percentage of 49%, IC2 in the layer in a volume percentage of 44% and TEG1 in the layer in a volume percentage of 7%. Similarly, the electron-transporting layer may also consist of a mixture of two materials.

[0219] OLEDs are characterized by standard methods. For this purpose, the electroluminescence spectrum, the current efficiency (CE, measured in cd / A), and the external quantum efficiency (EQE, measured in %) are determined as a function of luminance and, like the lifetime, are calculated from the current-voltage-luminance characteristics assuming Lambertian emission characteristics. The electroluminescence spectrum is measured at a luminous flux density of 1000 cd / m 2 The CIE 1931 x and y color coordinates are calculated from it. The expression U1000 in Table 3 means a luminous flux density of 1000 cd / m2 The voltage required for CE1000 and EQE1000 is 1000cd / m 2 The current efficiency and external quantum efficiency obtained at 1000 Hz are shown. The lifetime LT is defined as the time until the luminous flux density drops to a certain percentage L1 from the initial luminous flux density when driven at a constant current. The value L1=80% in Table 3 means that the lifetime reported in the LT column corresponds to the time when the luminous flux density drops to 80% of the initial value.

[0220] Use of the compounds of the present invention as electron transport materials The material of the present invention can be used in the electron transport layer (ETL) of OLED. The compound EG1 of the present invention can be used in Examples I1, I2, I5 and I6 as an electron transport material in fluorescent blue OLED. Furthermore, the material of the present invention can then be used in the hole blocking layer (HBL). This is shown in Experiments I3, I4, I7 and I8.

[0221] Use of the compounds of the present invention as matrix materials in phosphorescent OLEDs The materials of the invention can be used in the light-emitting layer in phosphorescent (eg green) OLEDs. The compounds of the invention EG1 to EG4 can be used in examples I9 to I12 as matrix materials in the light-emitting layer. [Table 1] [Table 2-1] [Table 2-2] [Table 3]

[0222] heat resistance The compound EG1 of the invention shows a significant increase in heat resistance by comparison with the literature compound ST3, which is determined by heat treatment of both materials at 350° C. for 7 days in an evacuated glass ampoule. Analytical determination of purity (HPLC) shows the following results: [Table 4]

Claims

1. A compound comprising at least one structure of formula (I). 【Chemistry 1】 (wherein the symbols used are as follows: X is the same or different at each occurrence and is N or CR; R ａ are the same or different for each occurrence, H, D, F, Cl, Br, I, CN, NO ２ , N(Ar ａ ) ２ , N(R) ２ , C(=O)Ar ａ , C(=O)R ２ , P(=O)(Ar ａ ) ２ , P(Ar ａ ) ２ , B(Ar ａ ) ２ , B(OR) ２ , Si(Ar ａ ) ３ , Si(R) ３ a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which is optionally substituted by one or more R radicals, and wherein one or more non-adjacent CH ２ The groups are -RC=CR-, -C≡C-, Si(R) ２ , Ge(R) ２ , Sn(R) ２ , C=O, C=S, -O-, -Se-, -S-, C=Se, -C(=O)O-, -C(=O)NR-, C=NR, NR, P(=O)(R), SO or SO ２ and where one or more hydrogen atoms are replaced by D, F, Cl, Br, I, CN or NO ２ or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and optionally substituted by one or more R radicals, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and optionally substituted by one or more R radicals, or a combination of these systems; ａ The radicals, together with each other or with the R radicals, may form a ring system; Ar ａ are identical or different at each occurrence and are aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms and optionally substituted by one or more non-aromatic R radicals; and at the same time, two Ar ａ The radical is a bridge by a single bond or B(R), C(R) ２ , Si(R) ２ , C=O, C=NR, C=C(R) ２ , O, S, Se, S=O, SO ２ , N(R), P(R) and P(=O)R; R is the same or different at each occurrence and is H, D, OH, F, Cl, Br, I, CN, NO ２ , N(Ar) ２ , N(R １ ) ２ , C(=O)Ar, C(=O)R １ , P(=O)(Ar) ２ , P(Ar) ２ , B(Ar) ２ , B(OR １ ) ２ , Si(Ar) ３ , Si(R １ ) ３ a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be represented by one or more R ２ radical, wherein one or more non-adjacent CH ２ The group is -R １ C=CR １ -, -C≡C-, Si(R １ ) ２ , Ge(R １ ) ２ , Sn(R １ ) ２ , C=O, C=S, C=Se, -C(=O)O-, -C(=O)NR １ -, C=NR １ , N.R. １ , P(=O)(R １ ), —O—, —S—, —Se—, SO or SO ２ and where one or more hydrogen atoms are replaced by D, F, Cl, Br, I, CN or NO ２ or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be replaced by one or more R １ or having 5 to 60 aromatic ring atoms and one or more R １ an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 60 aromatic ring atoms and one or more R １ aryl or heteroaryl groups, or combinations of these systems, optionally substituted by radicals; １ the radicals may together form a ring system; Ar is the same or different at each occurrence and has 5 to 30 aromatic ring atoms and one or more non-aromatic R １ at the same time, two Ar radicals bonded to the same silicon, nitrogen, phosphorus or boron atom are bridged by a single bond or B(R １ ), C(R １ ) ２ , Si(R １ ) ２ , C=O, C=NR １ , C=C(R １ ) ２ , O, S, Se, S=O, SO ２ , N(R １ ), P(R １ ) and P(=O)R １ may also be coupled together via a bridge selected from: R １ are the same or different for each occurrence, H, D, OH, F, Cl, Br, I, CN, NO ２ , N(Ar １ ) ２ , N(R ２ ) ２ , C(=O)Ar １ , C(=O)R ２ , P(=O)(Ar １ ) ２ , P(Ar １ ) ２ , B(Ar １ ) ２ , B(OR ２ ) ２ , Si(Ar １ ) ３ , Si(R ２ ) ３ a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be represented by one or more R ２ radical, wherein one or more non-adjacent CH ２ The group is -R ２ C=CR ２ -, -C≡C-, Si(R ２ ) ２ , Ge(R ２ ) ２ , Sn(R ２ ) ２ , C=O, C=S, C=Se, C=NR ２ , -C(=O)O-, -C(=O)NR ２ -, N.R. ２ , P(=O)(R ２ ), —O—, —S—, —Se—, SO or SO ２ and where one or more hydrogen atoms are replaced by D, F, Cl, Br, I, CN or NO ２ or having 5 to 40 aromatic ring atoms, and in each case, one or more R ２ an aromatic or heteroaromatic ring system, or a ring system having 5 to 40 aromatic ring atoms, optionally substituted by a radical, and one or more R ２ an aryloxy or heteroaryloxy group, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R ２ aryl or heteroaryl groups, or combinations of these systems, optionally substituted by radicals; １ the radicals may together form a ring system; Ar １ are the same or different at each occurrence and have 5 to 30 aromatic ring atoms and one or more non-aromatic R ２ at the same time, two Ar １ The radical is bridged by a single bond or B(R ２ ), C(R ２ ) ２ , Si(R ２ ) ２ , C=O, C=NR ２ , C=C(R ２ ) ２ , O, S, Se, S=O, SO ２ , N(R ２ ), P(R ２ ) and P(=O)R ２ may also be coupled together via a bridge selected from: R ２ are the same or different for each occurrence, H, D, F, Cl, Br, I, CN, B (OR ３ ) ２ , NO ２ , C(=O)R ３ , C.R. ３ = C(R ３ ) ２ , C(=O)OR ３ , C(=O)N(R ３ ) ２ , Si(R ３ ) ３ , P(R ３ ) ２ , B(R ３ ) ２ , N(R ３ ) ２ , NO ２ , P(=O)(R ３ ) ２ , OSO ２ R ３ , OR ３ , S(=O)R ３ , S(=O) ２ R ３ , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be represented by one or more R ３ radical, wherein one or more non-adjacent CH ２ The group is -R ３ C=CR ３ -, -C≡C-, Si(R ３ ) ２ , Ge(R ３ ) ２ , Sn(R ３ ) ２ , C=O, C=S, C=NR ３ , -C(=O)O-, -C(=O)NR ３ -, N.R. ３ , P(=O)(R ３ ), —O—, —S—, —Se—, SO or SO ２ and where one or more hydrogen atoms are replaced by D, F, Cl, Br, I, CN or NO ２ or having 5 to 40 aromatic ring atoms, and in each case, one or more R ３ an aromatic or heteroaromatic ring system, or a ring system having 5 to 40 aromatic ring atoms, optionally substituted by a radical, and one or more R ３ an aryloxy or heteroaryloxy group, or a combination of these systems, optionally substituted by a radical; ２ the substituents may together form a ring system; R ３ are identical or different at each occurrence and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and may be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; ３ The substituents can together form a ring system.

2. 2. The compound of claim 1, comprising at least one structure of formula (IIa), (IIb), (IIc) or (IId). 【Chemistry 2】 (wherein the symbols R and X have the meanings set forth in claim 1, p is 0 or 1 and Y is B(R), C(R) ２ , Si(R) ２ , C=O, C=NR, C=C(R) ２ , O, S, Se, S=O, SO ２ , N(R), P(R) and P(=O)R, where R is not -OH.

3. 3. The compound of claim 1 or 2, comprising at least one structure of formula (IIIa), (IIIb), (IIIc) or (IIId). 【Chemistry 3】 in which the symbol R has the meaning according to claim 1, the symbols Y and p have the meaning according to claim 2, l is 1, 2, 3, 4 or 5 and m is 0, 1, 2, 3 or 4, with the proviso that R is not -OH.

4. The compound comprises a hole transport group selected from formulas (H-1) to (H-3), where R ａ 4. The compound according to claim 1, wherein one of the groups or one of the R groups comprises a hole transporting group. 【Chemistry 4】 (wherein the dotted bond indicates the position of the bond, and Ar ２ , Ar ３ , Ar ４ each independently represents an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, each of which is represented by one or more R １ and optionally substituted by radicals; p is 0 or 1, and W １ is C(R １ ) ２ , Si(R １ ) ２ , C=O, N-Ar １ , B.R. １ , P.R. １ , P.O.R. １ , SO, SO ２ , Se, O or S, where the symbol Ar １ and R １ has the meaning given in claim 1, where the presence of an N-N bond is excluded and in the case where Y is NR, the index p is 1.

5. The compound comprises an electron transport group represented by formula (QL) ａ 5. The compound according to claim 1, wherein one of the groups or one of the R groups comprises an electron transport group. 【Chemistry 5】 (Here, L １ is a bond or has 5 to 40 aromatic ring atoms and one or more R １ represents an aromatic or heteroaromatic ring system, optionally substituted by radicals, and Q is an electron transport group selected from the structures of formula (Q-1), (Q-2), (Q-4), (Q-3), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and / or (Q-10), 【Chemistry 6】 where the dotted lines indicate the bond positions, Q′ is the same or different at each occurrence, CR １ or N, and Q'' is NR １ , O or S; where at least one Q′ is N; Here, R １ has the meaning given in claim 1)

6. At least one R in formula (I), (IIa), (IIb), (IIc), (IId), (IIIa), (IIIb), (IIIc) or (IIId) ａ or the R group is of the formula L １ A group represented by -Z (wherein L １ is a bond or has 5 to 40 aromatic ring atoms and one or more R １ represents an aromatic or heteroaromatic ring system, optionally substituted by a radical; Z represents R １ , Ar or formula Z ａ Or Z ｂ where the symbols Ar and R １ has the meaning given in claim 1 and Z ａ Or Z ｂ The compound according to any one of claims 1 to 5, characterized in that: 【Chemistry 7】 wherein W is the same or different at each occurrence, has 5 to 30 aromatic ring atoms, and is selected from one or more R １ Ar and R are optionally substituted aromatic or heteroaromatic ring systems, nitrogen atoms, boron atoms, phosphorus atoms or phosphine oxide groups, with the dotted lines indicating the points of attachment and the symbols Ar and R １ has the meaning given in claim 1, with the proviso that R １ is not -OH)

7. The compound of claim 6, comprising at least one structure of formula (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), (IVh), (IVi), (IVj), (IVk), (IVl), (IVm), (IVn), (IVo), (IVp), (IVq), (IVr), (IVs), (IVt), (IVu), (IVv), (IVw), (IVx) or (IVy). 【Chemistry 8-1】 【Chemistry 8-2】 【Chemistry 8-3】 【Chemistry 8-4】 【Chemistry 8-5】 【Chemistry 8-6】 【Chemistry 8-7】 【Chemistry 8-8】 (Here, the symbol R １ has the meaning given in claim 1 and the symbol L １ and Z have the meanings according to claim 6, l is 1, 2, 3, 4 or 5, m is 0, 1, 2, 3 or 4 and n is 0, 1, 2 or 3, with the proviso that R １ is not -OH)

8. 8. The compound of claim 6 or 7, comprising at least one structure of formula (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg) or (Vh). 【Chemistry 9-1】 【Chemistry 9-2】 【Chemistry 9-3】 (Here, the symbol R １ has the meaning given in claim 1 and the symbol L １ and Z has the meaning according to claim 6, m is 0, 1, 2, 3 or 4 and n is 0, 1, 2 or 3.

9. 8. The compound according to claim 6 or 7, comprising at least one structure of formula (VIa), (VIb), (VIc), (VId), (VIe), (VIf), (VIg), (VIh), (VIi), (VIj), (VIk), (VIl), (VIm), (VIn), (VIo), (VIp), (VIq), (VIr), (VIs) or (VIt). 【Chemistry 10-1】 【Chemistry 10-2】 【Chemistry 10-3】 【Chemistry 10-4】 【Chemistry 10-5】 【Chemistry 10-6】 (Here, the symbol R １ has the meaning given in claim 1 and the symbol L １ and Z has the meaning according to claim 6, l is 1, 2, 3, 4 or 5, m is 0, 1, 2, 3 or 4 and n is 0, 1, 2 or 3.

10. 10. An oligomer, polymer or dendrimer comprising one or more compounds according to any one of claims 1 to 9, wherein apart from hydrogen atoms or substituents there is one or more bonds of said compounds to said polymer, oligomer or dendrimer.

11. A composition comprising at least one compound according to any one of claims 1 to 9 or an oligomer, polymer or dendrimer according to claim 10 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, multipod emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials and hole blocking materials.

12. A formulation comprising at least one compound according to any one of claims 1 to 9, or an oligomer, polymer or dendrimer according to claim 10, or a composition according to claim 11, and at least one solvent.

13. Use of at least one compound according to any one of claims 1 to 9, or an oligomer, polymer or dendrimer according to claim 10, or a composition according to claim 11, as a host material, a hole transport material or an electron transport material in an electronic device.

14. A method for preparing at least one compound according to any one of claims 1 to 9, or an oligomer, polymer or dendrimer according to claim 10, characterized in that at least one nitrogen-containing heterocyclic group is attached to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction.

15. 12. An electronic device comprising at least one compound according to any one of claims 1 to 9, an oligomer, polymer or dendrimer according to claim 10, or a composition according to claim 11, said electronic device being selected from the group consisting of an organic electroluminescent device, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic photodetector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, and an organic laser diode.

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