CN115244728A - Use of sulfone compounds in organic electronic devices - Google Patents

Abstract

The present invention relates to the use of compounds in electronic devices. The present invention also relates to novel compounds, especially for use in electronic devices, and electronic devices comprising these compounds.

Description

Use of sulfone compounds in organic electronic devices

The present invention describes the use of sulfone compounds in organic electronic devices. The present invention also relates to novel sulfone compounds and methods for preparing the compounds of the present invention and electronic devices comprising these compounds.

Structures of organic electroluminescent devices in which organic semiconductors are used as functional materials are described, for example, in US 4539507, US 5151629, EP 0676461, WO 98/27136 and WO 2010/151006 A1. The luminescent materials used are generally organometallic complexes which exhibit phosphorescence. For quantum mechanical reasons, up to four times the energy and power efficiency can be achieved using organometallic compounds as phosphorescent emitters. In electroluminescent devices in general, and especially in electroluminescent devices exhibiting phosphorescence, there is still a need for improvement, eg in terms of efficiency, operating voltage and lifetime. Also known are organic electroluminescent devices comprising fluorescent emitters or emitters exhibiting TADF (Thermally Activated Delayed Fluorescence).

The performance of organic electroluminescent devices does not only depend on the emitters used. Also of particular importance here are other materials used in particular, such as host/matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials. Improvements to these materials can lead to significant improvements in electroluminescent devices.

In general, in the case of these materials, for example as emitters, preferably as fluorescent emitters, or as host materials, hole transport materials or electron transport materials, there is still a need for improvement, especially with regard to lifetime, and in terms of device efficiency and operating voltage. Furthermore, the compounds should have high color purity.

Another object of the present invention is to provide suitable use in organic electronic devices, especially in organic electroluminescent devices, as fluorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence) and when used in such Compounds that result in good device performance in devices, as well as corresponding electronic devices.

It is therefore an object of the present invention to provide compounds which are suitable for use in organic electronic devices, especially organic electroluminescent devices and which result in good device performance when used in such devices, and corresponding electronic devices .

A particular object of the present invention is to provide compounds which lead to high lifetime, good efficiency and low operating voltage. In particular, the properties of the host material, hole transport material or electron transport material also have a crucial influence on the lifetime and efficiency of organic electroluminescent devices.

Another problem addressed by the present invention can be considered to provide compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, especially as host materials. More particularly, the problem addressed by the present invention is to provide host materials suitable for use in red, yellow and blue phosphorescent electroluminescent devices.

In addition, the compounds, especially when they are used as host materials, hole transport materials or electron transport materials in organic electroluminescent devices, will lead to devices with excellent color purity.

Furthermore, the compounds should be processable in a very simple manner and in particular exhibit good solubility and film-forming properties. For example, the compounds should exhibit increased oxidative stability and improved glass transition temperature.

Another aim can be considered to provide electronic devices with excellent properties as cheaply as possible and with constant quality.

Furthermore, the electronics should be able to be used or adapted for many purposes. More particularly, the performance of electronic devices should be maintained over a wide temperature range.

Surprisingly, the specific compounds described in detail below have been found to solve these problems and eliminate the disadvantages of the prior art. The use of said compounds results in organic electronic devices, especially organic electroluminescent devices, with very good properties, especially with regard to lifetime, efficiency and operating voltage. Accordingly, the present invention provides electronic devices, especially organic electroluminescent devices, comprising such compounds, and corresponding preferred embodiments.

Accordingly, the present invention provides the use of a compound comprising at least one structure of formula (I), preferably a compound of formula (I), in an organic electronic device,

in:

W is C=O, C=N-Ar or SO2 _;

Ar is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups; the Ar groups here may be combined with at least one second Ar group, R group, X group, or another group forms a ring system;

X is N or CR, provided that no more than two X groups in a ring are N;

R is the same or different in each case and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar') ₂ , N(R1 _{)2 ,} C( ⁼ O)N (Ar') ₂ , C(=O)N(R ¹ ) ₂ , C(Ar') ₃ , C(R ¹ ) ₃ , Si(Ar') ₃ , Si(R ¹ ) ₃ , B(Ar' ) ₂ , B(R ¹ ) ₂ , C(=O)Ar', C(=O)R ¹ , P(=O)(Ar') ₂ , P(=O)(R ¹ ) ₂ , P( Ar') ₂ , P(R ¹ ) ₂ , S(=O)Ar', S(=O)R ¹ , S(=O) ₂ Ar', S(=O) ₂ R ¹ , OSO ₂ Ar' , OSO ₂ R ¹ , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or A branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl The groups may in each case be substituted by one or more R ¹ groups, wherein one or more non-adjacent CH ₂ groups may be replaced by R ¹ C=CR ¹ , C≡C, Si(R ¹ ) _2. C=O, C=S, C=Se, C=NR ¹ , -C(=O)O-, -C(=O)NR ¹ -, NR ¹ , P(=O)(R ¹ ) , -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring having ₅ to 60 aromatic ring atoms and in each case may be substituted by ^one or more R1 groups system, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and may be substituted with ^one or more R groups; at the same time, two R groups may also be taken together to form a ring system or form a ring system with another group;

Ar' is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by ^one or more R groups; at the same time, bonded to the same carbon The two Ar' groups of atoms, silicon atoms, nitrogen atoms, phosphorus atoms or boron atoms can also be via a bridging group via a single bond or selected from the group consisting of B(R ¹ ), C(R ¹ ) ₂ , Si(R ¹ . ) ₂ , C=O, C=NR ¹ , C=C(R ¹ ) ₂ , O, S, S=O, SO ₂ , N(R ¹ ), P(R ¹ ), and P(=O)R The bridging bases of ¹ are connected together;

R ¹ is the same or different in each case and is H, D, F, Cl, Br, I, CN, NO ₂ , N(Ar”) ₂ , N(R ² ) ₂ , C(=O)Ar” , C(=O)R ² , P(=O)(Ar”) ₂ , P(Ar”) ₂ , B(Ar”) ₂ , B(R ² ) ₂ , C(Ar”) ₃ , C( R ² ) ₃ , Si(Ar”) ₃ , Si(R ² ) ₃ , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or 3 to 40 A branched or cyclic alkyl, alkoxy or thioalkoxy group of carbon atoms, or an alkenyl group of 2 to 40 carbon atoms, each of which may be replaced by a or more R ² groups, wherein one or more non-adjacent CH ₂ groups may be substituted with -R ² C=CR ² -, -C≡C-, Si(R ² ) ₂ , C=O, C=S, C=Se, C=NR ² , -C(=O)O-, -C(=O)NR ² -, NR ² , P(=O)(R ² ), -O-, - S-, SO or SO and where one or more of the _hydrogen atoms can be replaced by D, F, Cl, Br, I, CN or NO, or with ₅ to 60 aromatic ring atoms and in each case Aromatic or heteroaromatic ring systems which may be substituted with one or more R groups, or ^aryloxy or heteroaryl groups having ⁵ to 60 aromatic ring atoms which may be substituted with one or more R groups an oxy group, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and may be substituted with one or more R groups, or a combination of these systems; simultaneously, ^two or More preferably adjacent R ¹ groups can form a ring system together; at the same time, one or more R ¹ groups can form a ring system with another part of the compound;

Ar" is the same or different in each case and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which may be substituted by one or more R groups ^; at the same time, bonded to the same carbon The two Ar" groups of atoms, silicon atoms, nitrogen atoms, phosphorus atoms or boron atoms can also be via a bridging group through a single bond or selected from B(R ² ), C(R ² ) ₂ , Si(R ² ) ) ₂ , C=O, C=NR ² , C=C(R ² ) ₂ , O, S, S=O, SO ₂ , N(R ² ), P(R ² ), and P(=O)R The bridging bases of ² are connected together;

R ² is in each case the same or different and is selected from H, D, F, CN, aliphatic hydrocarbyl radicals having 1 to 20 carbon atoms, or aromatic or heterocyclic radicals having 5 to 30 aromatic ring atoms Aromatic ring systems in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be replaced by Substituted with one or more alkyl groups, each of which has from 1 to 4 carbon atoms; at the same time, ^two or more preferably adjacent substituents R2 may together form a ring system.

The compounds of the invention can preferably be used as active compounds in electronic devices. Active compounds are generally organic or inorganic materials such as charge-injecting, charge-transporting or charge-blocking materials, but especially light-emitting materials and base material. Organic materials are preferred here.

The compounds used according to the invention are preferably pure organic compounds. Pure organic compounds are compounds that are not associated with metal atoms, ie do not form coordination compounds with metal atoms or do not form covalent bonds with metal atoms. The pure organic compound here preferably does not contain any metal atoms used in the phosphorescent emitter. These metals, such as copper, molybdenum, etc., especially rhenium, ruthenium, osmium, rhodium, iridium, palladium, will be discussed in detail later.

Compounds that can be used as active compounds in organic electronic devices may preferably be selected from fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection Materials, hole transport materials, hole injection materials, n-type dopants, p-type dopants, wide bandgap materials, electron blocking materials and/or hole blocking materials. Preferred here are fluorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-type doping materials Dopants, p-type dopants, wide bandgap materials, electron blocking materials and/or hole blocking materials. Particularly preferably, the above-detailed compounds comprising the structure of formula (I), preferably compounds of formula (I), are used as host materials, electron transport materials, hole blocking materials and/or compounds exhibiting TADF (thermally activated delayed fluorescence). Emitters, more preferably as host material for phosphorescent emitters, and especially preferably as host material for blue phosphorescent _emitters if W is C=O or SO2.

In the context of the present invention, adjacent carbon atoms are carbon atoms that are directly bonded to each other. In addition, "adjacent groups" in the group definition means that these groups are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply especially correspondingly to the terms "adjacent group" and "adjacent substituent".

In the context of the present specification, the expression that two or more groups can together form a ring is understood to mean, in particular, that the two groups are connected to each other by a chemical bond and formally eliminate two hydrogen atoms. This is illustrated by the following scheme:

In addition, however, the above expressions should also be understood to mean that if one of the two groups is hydrogen, the second group is bound to the bonding position of the hydrogen atom, thereby forming a ring. This will be illustrated by the following scheme:

A fused aryl group, fused aromatic ring system or fused heteroaromatic ring system in the context of the present invention is one in which two or more aromatic groups are fused to each other (ie condensed) along a common edge, A group such that, for example, two carbon atoms belong to at least two aromatic or heteroaromatic rings, as is the case, for example, in naphthalene. In contrast, for example, fluorene is not a fused aryl group in the context of the present invention because the two aromatic groups in fluorene do not share a side. A corresponding definition applies to heteroaryl groups and fused ring systems which may contain, but not necessarily also, heteroatoms.

If ^two or more preferably adjacent R, R1 and/or R2 groups are taken together to form ^a ring system, the result may be a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

Aryl groups in the context of the present invention contain from 6 to 60 carbon atoms, preferably from 6 to 40 carbon atoms, more preferably from 6 to 30 carbon atoms; heteroaryl groups in the context of the present invention contain from 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, more preferably 2 to 30 carbon atoms, and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. Said heteroatoms are preferably selected from N, O and/or S. Aryl groups or heteroaryl groups are here understood to mean simple aromatic rings, ie benzene, or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or hetero Aryl groups such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, and the like.

Aromatic ring systems in the context of the present invention contain 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms in the ring system. Heteroaromatic ring systems in the context of the present invention contain from 1 to 60 carbon atoms, preferably from 1 to 40 carbon atoms, more preferably from 1 to 30 carbon atoms, and at least one heteroatom in the ring system, provided that the carbon atoms The sum with heteroatoms is at least 5. Said heteroatoms are preferably selected from N, O and/or S. An aromatic or heteroaromatic ring system in the context of the present invention is understood to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also Interrupted by non-aromatic units (preferably less than 10% of non-H atoms) such as carbon, nitrogen or oxygen atoms or carbonyl groups. For example, aromatic ring systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diarylethers, stilbene, etc. should therefore also be regarded as aromatic ring systems in the context of the present invention, and The same is true for systems in which two or more aryl groups are interrupted by, for example, linear or cyclic alkyl groups or by silyl groups. In addition, systems in which two or more aryl or heteroaryl groups are directly bonded to each other, such as biphenyl, terphenyl, tetraphenyl or bipyridine, should likewise be regarded as aromatic or heteroaromatic rings Tie.

Cyclic alkyl, alkoxy or thioalkoxy groups in the context of the present invention are understood to mean monocyclic, bicyclic or polycyclic groups.

In the context of the present invention, C ₁ to C ₂₀ alkyl groups in which the individual hydrogen atoms or CH ₂ groups may also be substituted by the aforementioned groups are understood to mean, for example, methyl, ethyl, n-propyl, isopropyl propyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl , neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-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 base, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, Pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-di Methyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl- n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl -n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-decyl-1- base, 1,1-diethyl-n-dodecane-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-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 groups. Alkenyl groups are understood to mean, for example, vinyl, 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. A C ₁ to C ₄₀ alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or 2-methylbutoxy.

嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、

唑、苯并

唑、萘并

唑、蒽并

唑、菲并

唑、异

唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘、4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩

嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-

二唑、1,2,4-

二唑、1,2,5-

二唑、1,3,4-

二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑。have from 5 to 60, preferably from 5 to 40, more preferably from 5 to 30 aromatic ring atoms and in each case can also be substituted by the abovementioned groups and can be linked to the aromatic ring via any desired position. An aromatic or heteroaromatic ring system to which a heteroaromatic system is attached is understood to mean, for example, a group derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, pyrene, chicory, Perylene, fluoranthene, benzofluoranthene, tetracene, pentacene, benzopyrene, biphenyl, bidiphenylidene, terphenyl, bitriphenylidene, fluorene, spirobifluorene, dihydrophenanthrene, dihydro Pyrene, tetrahydropyrene, cis or trans indenofluorene, cis or trans monobenzoindenofluorene, cis or trans dibenzoindenofluorene, trimeric indene, heterotrimeric indene, spirotri polyindene, spiroisotrimeric indene, 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, benzene And-7,8-quinoline, phenothiazine, pheno

oxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthroimidazole, pyridimidazole, pyrazinimidazole, quinoxalineimidazole,

azoles, benzos

azole, naphtho

azole, anthracene

azole, phenanthroline

azole, iso

azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazathene, 2,7-di Azapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraza Hetero perylene, pyrazine, phenazine, phen

oxazine, phenothiazine, fluorochrome, 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-triazole oxazine, 1,2,4-triazine, 1,2,3-triazine, tetrazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3 , 5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.

In a preferred configuration, the compounds used according to the invention may comprise at least one structure of formula (IIa), (IIb) and/or (IIc), preferably selected from formulae (IIa), (IIb) and (IIc) )compound of,

wherein the Ar and R groups have the definitions given above, especially for formula (I), the designations m are the same or different and are 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, particularly preferably 0 or 1.

It is also possible that two Ar groups, preferably two Ar groups bound to a nitrogen atom in formula (IIb), together form a ring having 5 to 60 aromatic atoms and may be replaced by one or more R groups A group-substituted aromatic or heteroaromatic ring system wherein the R group has the definitions detailed above, especially for formula (I).

In a preferred configuration, the compounds used according to the invention may comprise at least one structure of formula (IIb-1), (IIb-2), (IIb-3) and/or (IIb-4), preferably selected from compounds of formula (IIb-1), (IIb-2), (IIb-3) and/or (IIb-4),

wherein the X and R groups have the definitions given above, especially for formula (I), the designations m are the same or different and are 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, particularly preferably 0 or 1.

唑、苯并噻唑、5-芳基菲啶-6酮、9,10-脱氢菲、荧蒽、萘、菲、蒽、苯并蒽、茚并[1,2,3-jk]芴、芘、苝、苣、硼吖嗪、硼氧六环、硼杂环戊熳、硼氮六环、硼氮杂环戊熳、酮、氧化膦、芳基硅烷、硅氧烷及其组合。Preferably, at least one of the Ar and/or R groups is selected from: phenyl, fluorene, indenofluorene, spirobifluorene, carbazole, indenocarbazole, indolocarbazole, spirocarbazole , pyrimidine, triazine, quinazoline, quinoxaline, pyridine, quinoline, isoquinoline, lactam, triarylamine, dibenzofuran, dibenzothiophene, imidazole, benzimidazole, benzo

azole, benzothiazole, 5-arylphenanthridine-6-one, 9,10-dehydrophenanthrene, fluoranthene, naphthalene, phenanthrene, anthracene, benzanthracene, indeno[1,2,3-jk]fluorene, Pyrene, perylene, chicory, borazine, boroxane, borazine, borazane, borazine, ketone, phosphine oxide, arylsilane, siloxane, and combinations thereof.

A further possible preference is that any R group bonded directly to the nitrogen atom is not selected from the group consisting of OH, F, Cl, Br, I, CN, NO2, N(Ar _{)2 ,} N(R ¹ ) ₂ , wherein R ¹ has the definitions given above, especially for formula (I). In a further preferred embodiment, the structures of formula (I) and the preferred configurations of these structures shown above and below do not have any NN bonds.

唑基，苯并噻唑基，1-咔唑基、2-咔唑基、3-咔唑基、4-咔唑基或9-咔唑基，1-萘基或2-萘基，蒽基，优选9-蒽基，反式和顺式茚并芴基，茚并咔唑基，吲哚并咔唑基，螺咔唑基，5-芳基-菲啶-6-酮基，9,10-脱氢菲基，荧蒽基，甲苯基，均三甲苯基，苯氧基甲苯基，苯甲醚基，三芳基胺基，双(三芳基胺基)，三(三芳基胺基)，六甲基茚满基，四氢化萘基，单环烷基，双环烷基，三环烷基，烷基(例如叔丁基、甲基、丙基)，烷氧基，烷基硫基，烷基芳基，三芳基甲硅烷基，三烷基甲硅烷基，呫吨基，10-芳基吩

嗪基，菲基和/或联三苯叉基，所述基团中的每个可被一个或多个基团取代，但优选未被取代，特别优选的是苯基、螺二芴、芴、二苯并呋喃、二苯并噻吩、蒽、菲、联三苯叉基团。It is also possible that at least one of the Ar and/or R groups is selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl , tetraphenyl, especially branched tetraphenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl, 9,9'-diarylfluorenyl, 1-spirobi Fluorenyl, 2-spirobifluorenyl, 3-spirobifluorenyl or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-diphenyl furanyl or 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl or 4-dibenzothienyl, pyrenyl, triazinyl , imidazolyl, benzimidazolyl, benzo

azolyl, benzothiazolyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl, 1-naphthyl or 2-naphthyl, anthracenyl , preferably 9-anthryl, trans and cis-indenofluorenyl, indenocarbazolyl, indolocarbazolyl, spirocarbazolyl, 5-aryl-phenanthridine-6-one, 9,10 -Dehydrophenanthrenyl, fluoranthene, tolyl, mesityl, phenoxytolyl, anisole, triarylamine, bis(triarylamine), tris(triarylamine), Hexamethylindanyl, tetralinyl, monocycloalkyl, bicycloalkyl, tricycloalkyl, alkyl (eg tert-butyl, methyl, propyl), alkoxy, alkylthio, Alkylaryl, triarylsilyl, trialkylsilyl, xanthyl, 10-arylphene

Azinyl, phenanthryl and/or triphenylidene, each of said groups may be substituted by one or more groups, but preferably unsubstituted, particularly preferred are phenyl, spirobifluorene, fluorene , Dibenzofuran, dibenzothiophene, anthracene, phenanthrene, bi-triphenylidene group.

When the structures detailed above and below are substituted with substituents R, these substituents R are preferably selected from H, D, F, CN, N(Ar') ₂ , C(=O)Ar', P(=O )(Ar') ₂ , a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms , or an alkenyl group of 2 to 10 carbon atoms, each of which may be substituted by one or more R groups, wherein ^one or more non-adjacent _CH groups may be replaced by O-substituted and wherein one or more hydrogen atoms may be replaced by D or F, having 5 to 24 aromatic ring atoms and in each case by ^one or more R groups, but preferably unsubstituted aromatic aromatic or heteroaromatic ring systems, or aralkyl or heteroaralkyl groups having 5 to 25 aromatic ring atoms and which may be substituted by ^one or more R groups; Atomically bonded two substituents R may optionally form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by ^one or more R groups; wherein the Ar group has the above text, especially the definitions given for formula (I).

More preferably, these substituents R are selected from H, D, F, CN, N(Ar') ₂ , straight chain alkyl having 1 to 8 carbon atoms, preferably 1, 2, 3 or 4 carbon atoms groups, or branched or cyclic alkyl groups having 3 to 8 carbon atoms, preferably 3 or 4 carbon atoms, or 2 to 8 carbon atoms, preferably 2, 3 or 4 carbon atoms alkenyl groups of atoms, each of which may be substituted by ^one or more R groups, but preferably unsubstituted, or having 5 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms aromatic or heteroaromatic ring systems of aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms and in each case may be substituted by one or more non-aromatic R ¹ groups but preferably unsubstituted; , optionally, preferably ^two substituents R1 bonded to adjacent carbon atoms may optionally form ^a monocyclic or polycyclic aliphatic which may be substituted by one or more R2 groups but is preferably unsubstituted A ring system in which Ar may have the definition detailed above.

More preferably, the substituent R is selected from H or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, said aromatic or heteroaromatic ring Each of the aromatic ring systems may be substituted with ^one or more non-aromatic R1 groups, but are preferably unsubstituted. Examples of suitable substituents R are selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, tetraphenyl, especially branched tetraphenyl base, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl, 1-spirobifluorenyl, 2-spirobifluorenyl, 3-spirobifluorenyl or 4-spirobifluorenyl, Pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinoxalinyl, quinolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl or 4-dibenzofuranyl Dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl or 4-dibenzothienyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl and indenocarbazolyl, each of which may be substituted by ^one or more R1 groups, but is preferably unsubstituted.

A further possibility is that the structures shown above and below, preferably the substituents R of the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) do not form any A fused aromatic or heteroaromatic ring system, preferably any fused ring system. This includes the formation of fused ring systems with possible substituents R ¹ and R ² which may be bonded to the R or R ¹ group.

In another embodiment, it is possible that the compounds used according to the invention contain hole-transporting groups, which may be present in formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-1) to At least one of the Ar and/or R groups detailed above in the structure of (IIb-4) preferably especially comprises and preferably represents a hole transport group. Hole transport groups are known in the art, and they preferably include triarylamine or carbazole groups.

It is preferably possible that the hole transport group comprises a group selected from the group consisting of formulae (H-1) to (H-3) and preferably a group selected from the group consisting of formulae (H-1) to (H-3) group,

where the dotted keys mark the connection locations and the symbols are defined as follows:

Ar ² , Ar ³ , Ar ⁴ are in each case independently an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, said aromatic ring system or Each of the heteroaromatic ring systems may be substituted with ^one or more R groups;

p is 0 or 1;

Z is a bond or C(R ¹ ) ₂ , Si(R ¹ ) ₂ , C=O, NR ¹ , NAr ¹ , BR ¹ , PR ¹ , PO(R ¹ ), SO, SO ₂ , Se, O or S , preferably a bond or C(R ¹ ) ₂ , N-Ar ¹ , O or S;

wherein Ar ¹ is an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, which may be replaced by one or more R ¹ group is substituted and said R ¹ group has the definitions detailed above, especially for formula (I). At the same time, the presence of NN bonds is preferably excluded.

It is also possible that the hole transport group comprises a group selected from the group consisting of formulae (H-4) to (H-26) and preferably a group selected from the group consisting of formulae (H-4) to (H-26). group,

Wherein Y ¹ is O, S, C(R ¹ ) ₂ or NAr ¹ , the dotted key marks the connection 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, R ¹ has the definitions given above, especially for formula (I), and Ar ¹ and Ar ² have the above, especially for formula (H-1) and/or Definition given in (H-2). At the same time, the presence of NN bonds is preferably excluded.

It is clear from the wording above that if marked p=0, the corresponding Ar ² group is absent and a bond is formed.

Preferably, the Ar ² group may be fully conjugated with an aromatic or heteroaromatic group or a nitrogen atom to which the Ar ² group of formulae (H-1) to (H-26) may be bonded.

In another 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 6 to 12 carbon atoms and can be A substituted, but preferably unsubstituted, aromatic ring system with one or more R ¹ groups, wherein R ¹ may have the definitions given above, especially for 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 heteroaromatic ring atoms, said aromatic ring system or heteroaromatic ring Each of the systems may be substituted, but preferably unsubstituted, by one or more R ¹ groups, wherein R ¹ may have the definitions given above, especially for formula (I).

More preferably, the symbols Ar shown in the formulae (H- ¹ ) to (H-26) are especially those having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, more preferably 6 to 10 ring atoms Aryl or heteroaryl groups such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system corresponds directly (ie, via an atom of the aromatic or heteroaromatic group) to another group Atomic bonding.

It is also possible that the Ar ² groups shown in formulae (H-1) to (H-26) comprise an aromatic ring having not more than two fused aromatic and/or heteroaromatic 6-membered rings system; preferably, it does not contain any fused aromatic or heteroaromatic ring systems with fused 6-membered rings. Therefore, the naphthyl structure is superior to the anthracene structure. In addition, fluorenyl, spirobifluorenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures. Particular preference is given to structures having no condensed, eg phenyl, biphenyl, terphenyl and/or tetraphenyl structures.

It is also possible here that the Ar ² groups shown in the formulae (H-1) to (H-26) have in particular not more than 1 nitrogen atom, preferably not more than 2 heteroatoms, particularly preferably not more than 1 Heteroatoms and especially preferably no heteroatoms.

In another preferred embodiment of the present invention, Ar ³ and/or Ar ⁴ are in each case the same or different and have 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms An aromatic or heteroaromatic ring system, and more preferably an aromatic ring system having 6 to 12 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 aromatic ring atoms, the aromatic ring system or each of the heteroaromatic ring systems may be substituted, but preferably unsubstituted, by one or more R ¹ groups, where R ¹ may have the definitions given above, especially in formula (I).

In another embodiment, it is possible that the compounds used according to the invention comprise groups containing electron-transporting groups, which may be present in the formulae (I), (IIa) to (IIc) and/or (IIb- Preferred at least one of the above-detailed Ar and/or R groups in the structures 1) to (IIb-4) especially comprises and preferably represents an electron-transporting group-containing group. Electron transport groups are well known in the art and facilitate the ability of compounds to transport and/or conduct electrons.

In addition, compounds used according to the present invention exhibit surprising advantages, said compounds comprising at least one structure selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, Quinoline, isoquinoline, imidazole and/or benzimidazole, particular preference is given to pyrimidine, triazine and quinazoline. These structures generally facilitate the ability of the compound to transport and/or conduct electrons.

In a preferred configuration of the present invention, it is feasible that the electron-transporting group-containing group is a group that can be represented by formula (QL),

wherein L ¹ represents a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, aromatic ring atoms and which may be substituted by one or more R ¹ groups, and Q is an electron transporting group , wherein R ¹ has the definition given above, especially for formula (I), and the dashed bond marks the position of attachment.

Preferably, the L ¹ group may form complete conjugation with the Q group and the atom (preferably a carbon or nitrogen atom) to which the L ¹ group of formula (QL) is bound. Complete conjugation of an aromatic or heteroaromatic system is formed once a direct bond is formed between adjacent aromatic or heteroaromatic rings. Another bond between the aforementioned conjugated groups, eg via a sulfur, nitrogen or oxygen atom or a carbonyl group, is not detrimental to the conjugation. In the case of the fluorene system, the two aromatic rings are directly bonded, where the sp hybridized carbon atom at the ⁹ -position does prevent fusing of these rings, but conjugation is possible because the sp at the ⁹ -position Hybrid carbon atoms are not necessarily located between the electron transporting Q group and the atom through which the group of formula (QL) is bonded to other structural elements of the compound. In contrast, in the case of the second spirobifluorene structure, if the bond between the Q group and the aromatic or heteroaromatic group to which the L ¹ group of formula (QL) is bonded is via a spirobifluorene Complete conjugation can be formed by the same phenyl group in the fluorene structure or via the phenyl groups directly bonded to each other and in one plane in the spirobifluorene structure. If the bond between the Q group and the aromatic or heteroaromatic group to which the L1 group ^of formula (QL) is bonded is through a second spirobifluorene bonded via an ^sp3 hybridized carbon atom at the 9 position When different phenyl groups in the structure are bonded, the conjugation is interrupted.

In another preferred embodiment of the present invention, L ¹ is a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably having 6 to 12 carbon atoms Aromatic ring systems, and which may be substituted, but preferably unsubstituted, by one or more R ¹ groups, where R ¹ may have the definitions given above, especially for 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, the aromatic ring system and the heteroaromatic ring Each of the systems may be substituted, but preferably unsubstituted, by one or more R ² groups, where R ² may have the definitions given above, especially for formula (I).

More preferably, the symbols L ¹ shown in formula (QL) are in particular the same or different in each case and are bonds or have 5 to 24 ring atoms, preferably 6 to 13 ring atoms, more preferably 6 to 10 An aryl or heteroaryl group of 1 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded to the corresponding atom of the other group, i.e. via an aromatic or heteroaromatic The atoms of the group are bonded.

It is also possible that the L ¹ group shown in formula (QL) comprises an aromatic ring system having no more than two fused aromatic and/or heteroaromatic 6-membered rings, preferably not comprising any fused aromatic and/or heteroaromatic 6-membered rings of aromatic or heteroaromatic ring systems. Therefore, the naphthyl structure is superior to the anthracene structure. In addition, fluorenyl, spirobifluorenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures.

Particular preference is given to structures having no condensed, eg phenyl, biphenyl, terphenyl and/or tetraphenyl structures.

Examples of suitable aromatic or heteroaromatic ring systems L ¹ are selected from o-, m- or p-phenylene, o-, m- or p-biphenylene, terphenyl Subunits, especially branched terphenylene, tetraphenylene, especially branched tetraphenylene, fluorene, spirobifluorene, dibenzofuran, dibenzothiophene and carbazolylidene groups, each of which may be substituted with one or more R ¹ groups, but is preferably unsubstituted.

It is also possible that the L ¹ groups shown in formula (QL) have in particular not more than 1 nitrogen atom, preferably not more than 2 heteroatoms, particularly preferably not more than 1 heteroatom and more preferably no heteroatoms.

Preferably, the Q group or electron transporting group especially shown in formula (QL) may be selected from formulae (Q-1), (Q-2), (Q-3), (Q-4), (Q-1) -5), (Q-6), (Q-7), (Q-8), (Q-9) and/or (Q-10) structures,

where the dotted key marks the connection position,

Q' is the same or different in each case and is CR ¹ or N, and

Q" is NR ¹ , O or S;

where at least one Q' is N, and

R ¹ is as defined above, especially in formula (I).

In addition, the Q group or electron transporting group shown in particular in formula (QL) may preferably be selected from formulae (Q-11), (Q-12), (Q-13), (Q-14) and/or (Q-15) structure,

wherein the symbol R ¹ has the definitions given above especially for formula (I), X' is N or CR ¹ and the dashed bond marks the position of attachment, wherein X' is preferably a nitrogen atom.

In another embodiment, the Q group or electron transporting group shown in particular in formula (QL) may be selected from formulae (Q-16), (Q-17), (Q-18), (Q-19 ), (Q-20), (Q-21) and/or (Q-22) structures,

wherein the symbol R ¹ has the definition detailed above especially for formula (I), the dashed bond marks the position of attachment and m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and n is 0, 1, 2 or 3, preferably 0, 1 or 2, and o is 0, 1 or 2, preferably 1 or 2. The structures of formulae (Q-16), (Q-17), (Q-18) and (Q-19) are preferred here.

In another embodiment, the Q group or electron transporting group shown in particular in formula (QL) may be selected from structures of formula (Q-23), (Q-24) and/or (Q-25),

where the symbol R ¹ has the definition detailed above especially for formula (I), and the dashed bond marks the position of attachment.

In another embodiment, the Q group or electron transporting group shown in particular in formula (QL) may be selected from formulae (Q-26), (Q-27), (Q-28), (Q-29 ) and/or (Q-30) structure,

wherein the symbols Ar ¹ and R ¹ have the definitions given above in particular for formula (I) and/or (H-2), (H-3), X' is N or CR ¹ and the dashed bond marks the position of attachment. Preferably, in the structures of formulae (Q-26), (Q-27) and (Q-28) exactly one X' is a nitrogen atom.

Preferably, the Q group or electron transporting group especially shown in formula (QL) may be selected from formulae (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) structure,

wherein the symbols Ar ¹ and R ¹ have the definitions detailed above in particular for formula (I) and/or (H-2) or (H-3), the dashed bond marks 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 1 is 1, 2, 3 , 4 or 5, preferably 0, 1 or 2.

In another preferred embodiment of the invention, Ar ¹ is in each case the same or different and is an aromatic or heteroaromatic ring system, preferably having 5 to 24 aromatic ring atoms, preferably 6 to 18 An aryl or heteroaryl group of two aromatic ring atoms, and more preferably an aromatic ring system, preferably an aryl group having 6 to 12 aromatic ring atoms, or a heteroaromatic ring system, preferably Heteroaryl groups having ⁵ to ¹³ aromatic ring atoms, each of said groups may be substituted by one or more R groups, but preferably unsubstituted, wherein R may have the above, Especially the definitions detailed in formula (I).

Preferably, the symbol Ar1 is ^an aryl or heteroaryl group such that the aromatic or heteroaromatic group of the aromatic or heteroaromatic ring system is directly (ie, via an atom of the aromatic or heteroaromatic group) ) is bonded to the corresponding atom of a further group (eg a carbon or nitrogen atom of the (H-1) to (H-26) or (Q-26) to (Q-44) groups shown above).

Advantageously, Ar ¹ in formulae (H-1) to (H-26) or (Q-26) to (Q-44) has 6 to 12 aromatic ring atoms and may be replaced by one or more R ² The group is a substituted, but preferably unsubstituted, aromatic ring system in which R ² may have the definitions detailed above, especially for formula (I).

Preferably, the R ^{1 or R 2 group in the formulae (H-1) to (H-26) or (Q-1) to (Q-44) is not an aryl group to which the R 1 or R 2 group is} bonded The ring atoms of the radical or heteroaryl groups Ar ¹ , Ar ² , Ar ³ and/or Ar ⁴ form a fused ring system. This includes the formation ^{of fused} ring systems with possible substituents R2 that may be bonded to the R1 group.

唑基，苯并噻唑基，1-咔唑基、2-咔唑基、3-咔唑基或4-咔唑基，1-萘基或2-萘基，蒽基，优选9-蒽基，菲基和/或联三苯叉基，所述基团中的每个可被一个或多个R¹基团取代，但优选未被取代，特别优选苯基、螺二芴、芴、二苯并呋喃、二苯并噻吩、蒽、菲、联三苯叉基团，其中所述R¹基团具有上文，尤其是在式(I)中给出的定义。It is also possible that the Ar', Ar ¹ , Ar ² , Ar ³ and/or Ar ⁴ radicals are selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched Chain terphenyl, tetraphenyl, especially branched tetraphenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl, 1-spirobifluorenyl, 2-spirobi Fluorenyl, 3-spirobifluorenyl or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl or 4-dibenzofuranyl Benzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazole base, benzo

azolyl, benzothiazolyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl, 1-naphthyl or 2-naphthyl, anthracenyl, preferably 9-anthryl , phenanthryl and/or triphenylidene, each of said groups may be substituted by one or more R ¹ groups, but preferably unsubstituted, particularly preferably phenyl, spirobifluorene, fluorene, difluorene Benzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylidene groups, wherein the R ¹ group has the definitions given above, especially in formula (I).

In a preferred embodiment, it is possible that at least two Ar and/or in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) The R group comprises a hole transport group and preferably represents a hole transport group.

It is also possible that at least one of the Ar and/or R groups in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) comprises two a hole transport group. The hole transporting group can be considered herein as the R ¹ group, in which case the substituent R ¹ in the structures of formulae (H-1) to (H-26) should be replaced by the R ² group.

In a preferred embodiment, it is possible that at least two Ar and/or in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) The R group includes an electron-transporting group-containing group and preferably represents an electron-transporting group-containing group.

It is also possible that at least one of the Ar and/or R groups in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) comprises two a group containing an electron-transporting group. A group containing an electron transporting group may be considered herein as a R ¹ group, in which case the substituent R in the structures of formula (QL) and/or (Q-1) to (Q-44) ¹ should be replaced by the ^R2 group.

In a preferred configuration, it is possible that the Ar and/or R groups in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) At least one of the R and/or Ar groups comprises and preferably represents a hole-transporting group, and at least one of the R and/or Ar groups comprises and preferably represents an electron-transporting group-containing group.

It is also possible that at least one of the Ar and/or R groups in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) comprises a Electron-transporting groups and hole-transporting groups. An electron-transporting group-containing group or a hole-transporting group may be considered herein to be an R ¹ group, in which case formula (QL), (Q-1) to (Q-44) or (H The substituent R ¹ in the structures of -1) to (H-26) should be replaced by an R ² group.

In another configuration, it is possible that at least one of the Ar and/or R groups comprises at least one group that results in a wide bandgap material. The expression "group leading to a wide-bandgap material" indicates that the compound can be used as a wide-bandgap material, and therefore the compound has a corresponding group. Wide bandgap materials will be discussed in detail later.

It is also possible that at least one of the Ar and/or R groups contains at least one group that results in a material serving as host material. The expression "group leading to a material used as host material" indicates that the compound can be used as a host material, and therefore the compound has the corresponding group. The host material will be discussed in detail later.

In another configuration, it is possible that the compound comprises a fused aromatic or heteroaromatic ring system having at least 2, preferably three, fused rings that may be optionally substituted.

Preferably, at least one of the Ar and/or R groups in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) comprises at least one group having two One, preferably an aromatic or heteroaromatic ring system having three fused aromatic or heteroaromatic rings.

It is preferably possible that the aromatic or heteroaromatic ring system having two, preferably three, fused aromatic or heteroaromatic rings is selected from the groups of formulae (Ar-1) to (Ar-17) ,

wherein X' is N or CR ¹ , preferably CR ¹ , and L ¹ represents a bond or an aromatic or heterocyclic atom having 5 to 40, preferably 5 to 30, aromatic ring atoms which may be substituted by one or more R ¹ groups Aromatic ring system in which R ¹ has the definition detailed above especially for formula (I) and the dashed bond marks the position of attachment.

Most preferably, where possible, the aromatic or heteroaromatic ring system having two, preferably three, fused aromatic or heteroaromatic rings is selected from the group consisting of formulae (Ar'-1) to (Ar'-17) the group,

wherein L ¹ represents a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, aromatic ring atoms and which may be substituted by one or more R ¹ groups, wherein R ¹ has the above, In particular for the definition detailed in formula (I), the dashed bond marks the position of attachment and is marked as follows:

p is 0 or 1;

e is 0, 1 or 2, preferably 0 or 1;

j is in each case independently 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 or 1;

h is in each case independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, more preferably 0 or 1;

s is an integer in the range from 0 to 7, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4, especially preferably 0, 1 or 2.

Preferably, the sum of the labels p, e, j, h and s in the structures of formulae (Ar'-1) to (Ar'-17) is in each case not greater than 3, preferably not greater than 2 and more preferably not greater than 1.

The structures of formulae (Ar-1) to (Ar-17) and/or (Ar'-1) to (Ar'-17) shown above for compounds suitable for use as fluorescent emitters or blue OLED materials are Especially preferred groups.

In another preferred embodiment of the present invention, L in the structures of formulae (Ar-1) to (Ar-17) and/or (Ar'-1) to (Ar'-17) shown above ¹ group is an aromatic or heteroaromatic ring system having 5 to 40, preferably ⁵ to 30, aromatic ring atoms and preferably substituted by ^one or more R1 groups, wherein R1 has the above, especially Definitions given for formula (I).

When aromatic and/or heteroaromatic groups are substituted with substituents R ¹ , these substituents R ¹ are preferably selected from H, D, F, CN, N(Ar") ₂ , C(=O)Ar", P(=O)(Ar") ₂ , a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms, or a branched or cyclic alkyl or alkane group having 3 to 10 carbon atoms An oxy group, or an alkenyl group of ² to 10 carbon atoms, each of which may be substituted with one or more R groups, one or more of which are non-adjacent _CH groups can be replaced by O and in which one or more hydrogen atoms can be replaced by D or F, have ⁵ to 24 aromatic ring atoms and in each case can be substituted by one or more R groups but are preferably not A substituted aromatic or heteroaromatic ring system, or an aralkyl or heteroaralkyl group having ⁵ to 25 aromatic ring atoms and which may be substituted by one or more R groups; Two substituents R1 bonded to adjacent carbon atoms may optionally form ^a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by ^one or more R1 groups; wherein The Ar" group has the definitions given above, especially for formula (I).

More preferably, these substituents R ¹ are selected from H, D, F, CN, N(Ar") ₂ , having 1 to 8 carbon atoms, preferably straight chain alkanes having 1, 2, 3 or 4 carbon atoms radicals, or branched or cyclic alkyl groups having 3 to 8 carbon atoms, preferably 3 or 4 carbon atoms, or 2 to 8 carbon atoms, preferably 2, 3 or 4 carbon atoms Alkenyl groups of carbon atoms, each of which may be substituted by one or more R groups, but preferably unsubstituted, or having ⁵ to 24 aromatic ring atoms, preferably 6 to 18 Aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms and in each case may be substituted by one or more non-aromatic R ¹ groups but are preferably unsubstituted aromatic or heteroaromatic ring systems; At the same time, the ^two substituents R1, preferably bonded to adjacent carbon atoms, may optionally form ^a monocyclic or polycyclic aliphatic ring system which may be substituted by one or more R2 groups but is preferably unsubstituted, wherein Ar ¹ may have the definition detailed above.

Most preferably, the substituent R1 is selected from H or ^an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, said aromatic or heteroaromatic ring is in each case substituted by one or more non-aromatic R ² groups, but is preferably unsubstituted. Examples of suitable substituents R ¹ are selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, tetraphenyl, especially branched tetraphenyl Phenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl, 1-spirobifluorenyl, 2-spirobifluorenyl, 3-spirobifluorenyl or 4-spirobifluorenyl , pyridyl, pyrimidinyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl or 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzofuranyl Benzothienyl, 3-dibenzothienyl or 4-dibenzothienyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl and indenocarbazolyl , each of said groups may be substituted with one or more R ² groups, but are preferably unsubstituted.

It is also possible that the substituent R ¹ of the aromatic or heteroaromatic ring system does not form a fused aromatic or heteroaromatic ring system with further ring atoms of the aromatic or heteroaromatic ring system, preferably any fused aromatic or heteroaromatic ring system Ring system. This includes the formation ^{of fused} ring systems with possible substituents R2 that may be bonded to the R1 group.

It is also possible that at least one R ¹ or Ar" group in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) is selected from the group consisting of formula ( Groups of R ¹ -1) to (R ¹ -43), or formulae (H-1) to (H-26), (QL), (Q-1) to (Q-44), (Ar-1) ) to (Ar-17) and/or at least one R ¹ in the structures of (Ar'-1) to (Ar'-17) is a group selected from the group consisting of formulae (R ¹ -1) to (R ¹ -43) group:

The symbols used are as follows:

Y ³ is O, S or NR ² , preferably O or S;

k is independently 0 or 1 in each case;

i is independently in each case 0, 1 or 2;

j is independently in each case 0, 1, 2 or 3;

h is independently in each case 0, 1, 2, 3 or 4;

g is independently in each case 0, 1, 2, 3, 4 or 5;

R ² may have the definitions given above, especially for formula (I), and the dashed bond marks the position of attachment.

Preference is given here to groups of the formulae R ¹ -1 to R ¹ -28, particular preference being given to R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ¹ -13, R ¹ -14, R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21 and/or R ¹ -22 groups.

It is preferably possible that the sum of the labels k, i, j, h and g in the structures of formulae (R ¹ -1) to (R ¹ -43) is in each case not greater than 3, preferably not greater than 2 and More preferably not more than 1.

Preferably, the R ² group in the formulae (R ¹ -1) to (R ¹ -43) does not form a fused ring atom with the aryl or heteroaryl group to which the R ² group is bound. Aromatic or heteroaromatic ring systems, and preferably not forming any fused ring systems.

The groups of formulae (R ¹ -1) to (R ¹ -43) detailed above are preferably Ar groups of formula (I) or Ar ³ , Ar of formulae (H-1) to (H-3) ⁴ groups or preferred embodiments of these formulae, wherein, in this case, the R ² groups shown in formulae (R ¹ -1) to (R ¹ -43) are replaced by R ¹ groups. The preferences detailed above with respect to formulae (R ¹ -1 ) to (R ¹ -43) apply accordingly.

It is preferably feasible that the compound contains at least one linking group selected from formulae (L ¹ -1) to (L ¹ -76); preferably, in formula (H-1) to (H-26) In the structure, the Ar ² group is selected from formulae (L ¹ -1) to (L ¹ -76), or the electron transport group is via a linking group selected from formula (L ¹ -1) to (L ¹ -76) Linked to other structural units, or the L ¹ group in formula (QL), (Ar-1) to (Ar-17) and/or (Ar'-1) to (Ar'-17) is selected from formula ( L ¹ -1) to (L ¹ -76) groups,

where the dotted key marks the connection position in each case, the mark k is 0 or 1, the mark l is 0, 1 or 2, the mark j is independently 0, 1, 2 or 3 in each case; the mark h is in each case each case is independently 0, 1, 2, 3 or 4, the notation g is 0, ¹ , 2, 3, 4 or 5; the notation ^Y2 is O, S or NR1, preferably O or S; and the notation R ¹ has the definitions given above, especially for formula (I).

It is preferably possible that the sum of the labels k, l, g, h and j in the structures of formulae (L ¹ -1) to (L ¹ -76) is in each case at most 3, preferably at most 2 and more At most 1 is preferred.

Preferred compounds having groups of formulae (H-1) to (H-26) comprise Ar ² groups selected from formulae (L ^{1 -1} ) to (L ¹ -46) and/or One of (L ¹ -57) to (L ¹ -76), preferably one of formulae (L ¹ -1) to (L ¹ -32) and/or (L ¹ -57) to (L ¹ -76), Especially preferred is one of the formulae (L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ -68). Advantageously, the formulae (L ¹ -1) to (L ¹ -46) and/or (L ¹ -57) to (L ¹ -76), preferably the formulae (L ¹ -1) to (L ¹ -32) and /or (L ¹ -57) to (L ¹ -76), structures of formulae (L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ -68) are particularly preferred The sum of the indices k, l, g, h and j in may in each case be no greater than 3, preferably no greater than 2 and more preferably no greater than 1.

Preferred compounds having a group of formula (QL) comprise an L ¹ group representing a bond or which is selected from formulae (L ^{1 -1} ) to (L ¹ -46) and/or (L ¹ - 57) to ^one of (L 1-76), preferably ^one of formulae (L ^1-1 ) to (L 1-32) and/or (L ^1-57 ) to (L ^1-76 ), especially preferred formula ( One of L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ -68). Advantageously, the formulae (L ¹ -1) to (L ¹ -46) and/or (L ¹ -57) to (L ¹ -76), preferably the formulae (L ¹ -1) to (L ¹ -32) and /or (L ¹ -57) to (L ¹ -76), particularly preferably structures of the formulae (L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ -68) The sum of the labels k, l, g, h and j in may in each case be no greater than 3, preferably no greater than 2 and more preferably no greater than 1.

Preferred compounds having groups of formulae (Ar-1) to (Ar-17) and/or (Ar'- ¹ ) to (Ar'-17) comprise ^an L1 group which is a bond or It is selected from one of formulae (L ¹ -1) to (L ¹ -46) and/or (L ¹ -57) to (L ¹ -76), preferably formulae (L ¹ -1) to (L ¹ -32) ) and/or one of (L ¹ -57) to (L ¹ -76), particularly preferably the formulae (L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ - 68) one. Advantageously, the formulae (L ¹ -1) to (L ¹ -46) and/or (L ¹ -57) to (L ¹ -76), preferably the formulae (L ¹ -1) to (L ¹ -32) and /or (L ¹ -57) to (L ¹ -76), particularly preferably structures of the formulae (L ¹ -1) to (L ¹ -10) and/or (L ¹ -57) to (L ¹ -68) The sum of the labels k, l, g, h and j in may in each case be no greater than 3, preferably no greater than 2 and more preferably no greater than 1.

Preferably, the R ¹ group in the formulae (L ¹ -1) to (L ¹ -76) does not form a fused ring atom with the aryl group or the heteroaryl group to which the R ¹ group is bound. Aromatic or heteroaromatic ring systems, and preferably not forming any fused ring systems.

In a preferred configuration, compounds useful according to the invention may be represented by at least one of the structures of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) . Preferably, the compounds comprising the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) have not more than 5000 g/mol, preferably not more than 4000 g/mol, particularly preferably Molecular weights of not more than 3000 g/mol, particularly preferably not more than 2000 g/mol and most preferably not more than 1200 g/mol.

Furthermore, preferred compounds which can be used according to the invention are characterized in that they are sublimable. These compounds typically have molar masses of less than about 1200 g/mol.

When the compounds ^of the present invention are substituted with aromatic or heteroaromatic R1 or R2 groups, it is preferred that these do not present any aryl or heteroaryl groups having more than ^two aromatic six-membered rings directly fused to each other group. More preferably, the substituents are completely free of any aryl or heteroaryl groups having six-membered rings directly fused to each other. The reason for this preference is the low triplet energy of such structures. Condensed aryl groups having more than two aromatic six-membered rings directly fused to each other but still suitable according to the invention are phenanthrene and bitriphenylidene, since these also have high triplet energy levels.

Where compounds of the invention are formulated for use as fluorescent emitters or as blue OLED materials, preferred compounds may contain corresponding groups, such as fluorene, anthracene and/or pyrene groups, which may be replaced by R ¹ or R ² group is substituted, or the group is substituted by ^a substituent R ¹ or R ² to (L ^1-1 ) to (L 1-76) or (R ^1-1 ) to (R ^1-43 ) group is formed by the corresponding substitution.

In another preferred embodiment of the invention, for example in the structures of formulae (I), (IIa) to (IIc) and/or (IIb-1 ) to (IIb-4) and the structures or references to these formulae R ² in preferred embodiments of the structure of , in each case the same or different and selected from H, D, F, CN, has 1 to 10 carbon atoms, preferably 1, 2, 3 or 4 carbon atoms aliphatic hydrocarbyl groups, or having 5 to 30 aromatic ring atoms, preferably 5 to 24 aromatic ring atoms, more preferably 5 to 13 aromatic ring atoms and may be composed of one or more each having 1 to 4 A carbon atom alkyl group substituted but preferably unsubstituted aromatic or heteroaromatic ring system.

Preferably, the ^R2 group does not form a fused aromatic or heteroaromatic ring system with a ring atom of the aryl or heteroaryl group to which the ^R2 group is bound, and preferably does not form any fused Ring system.

It is also possible that the compounds of the invention are not in direct contact with the metal atoms and are preferably not ligands of metal complexes.

The present invention further provides compounds comprising at least one structure of formula (III), preferably compounds of formula (III),

wherein the symbols X and W have the definitions given above, especially for formula (I), and HetAr is a heteroaromatic ring having 5 to 60 aromatic ring atoms and which may be substituted by ^one or more R groups system, wherein the HetAr group may form a ring system together with at least one Ar group, R group or another group, wherein HetAr is preferably selected from the above-defined formulae (H-1) to (H-26 ) or a group selected from formulae (QL) and (Q-1) to (Q-44) as defined above.

In another preferred embodiment, it is practicable that the compounds of the present invention comprise structures of formula (IVa), (IVb) and/or (IVc), wherein the compounds of the present invention may be more preferably selected from formula (IVa) , (IVb) and/or (IVc) compounds:

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and HetAr has the above, especially for formula (III) is given the definition, and is preferably selected from the above-defined formulae (H-1) to (H-26) or from the above-defined formulae (QL) and (Q-1) to (Q- 44) group.

In addition particular preference is given to compounds of the invention having the structure of formula (IVa), said compounds having the following properties:

Herein, the groups of formulae Q-11 to Q-25 in the compounds having the structures of formula (IVa) detailed in the table shown above comprise R ¹ groups preferably representing groups having ⁶ to 18 aromatic ring atoms, preferably aromatic or heteroaromatic ring systems having from 6 to 13 aromatic ring atoms, each of which may be replaced by one or more non-aromatic ring systems Group R2 groups are substituted; preferably, the groups of formulae Q ^- 11 to Q-25 in the compounds having the structures of formula (IVa) detailed in the table shown above have at least ^one R1 group, preferably at least Two R ¹ groups selected from formulae (R ^{1 -1} ) to (R ¹ -43), preferably formulae R ¹ -1 to R ¹ -28 and R ¹ -34 to R ¹ -38 groups, particularly preferably of formula R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ¹ -13, R ¹ -14, A group of R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ¹ -24 and/or R ¹ -37.

Also particularly preferred are compounds of the invention having the structure of formula (IVa), in which the HetAr group has and preferably represents at least one QL group, in which Q is selected from Q-16 to Q-19 and Q-23 to Q-25, preferably Q -23 to Q-25, more preferably Q-23, the compounds have the following properties:

Particular preference is also given to compounds according to the invention having the structure of formula (IVa), wherein the HetAr group has and preferably represents at least one hole-transporting group, wherein the hole-transporting group is selected from H-1 to H-3, the Compounds have the following properties:

Particular preference is also given to compounds according to the invention having the structure of formula (IVa), wherein the HetAr group has and preferably represents at least one hole-transporting group, wherein the hole-transporting group is selected from H-4 to H-26, the Compounds have the following properties:

Also particularly preferred are compounds of the invention having the structure of formula (IVb), said compounds having the following properties:

In the present context, the groups of formulae Q-11 to Q-25 in the compounds having the structures of formula (IVb) detailed in the table shown above comprise a R ¹ group preferably representing ^a group having 6 to 18 aromatic ring atoms, preferably aromatic or heteroaromatic ring systems having 6 to 13 aromatic ring atoms, each of said aromatic or heteroaromatic ring systems may be Aromatic R ² groups are substituted; preferably, the groups of formulae Q-11 to Q-25 in the compounds having the structures of formula (IVa) detailed in the table shown above have at least one R ¹ group, preferably At least two R ¹ groups selected from formulae (R ^{1 -1} ) to (R ¹ -43), preferably formulae R ¹ -1 to R ¹ -28 and R ¹ -34 to R ^1-38 groups, especially preferably of formula R ^1-1 , R ^1-3 , R ^1-4 , R ^1-10 , R ^1-11 , R ^1-12 , R ^1-13 , R ^1-14 , R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ¹ -24 and/or R ¹ -37 groups .

In a preferred embodiment, it is possible that at least one of the HetAr groups and the Ar and/or R groups in the structures of formula (III), (IVa), (IVb) and/or (IVc) Each contains and preferably represents a hole transport group.

It is also possible that the HetAr groups in the structures of formula (III), (IVa), (IVb) and/or (IVc) comprise two hole transporting groups. A hole transporting group can be regarded as an R ¹ group herein, in which case the substituent R ¹ in the structures of formulae (H-1) to (H-26) should be replaced by an R ² group.

In a preferred embodiment, it is feasible that at least one of the HetAr group and the Ar and/or R group in the structures of formula (III), (IVa), (IVb) and/or (IVc) Each of them includes and preferably represents a group containing an electron transport group.

It is also possible that the HetAr groups in the structures of formula (III), (IVa), (IVb) and/or (IVc) comprise two groups containing electron transporting groups. A group containing an electron transporting group can be considered herein as a R ¹ group, in which case the substituent R in the structures of formula (QL) and/or (Q-1) to (Q-44) ¹ should be replaced by the ^R2 group.

In a preferred configuration, it is possible that HetAr, Ar and/or R in the structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) At least one of the groups comprises and preferably represents a hole-transporting group, and at least one of the HetAr, Ar and/or R groups comprises and preferably represents an electron-transporting group-containing group.

It is also possible that the HetAr groups in the structures of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) comprise electron-transporting group-containing groups and empty hole transport group. An electron-transporting group-containing group or a hole-transporting group may be considered herein as a R ¹ group, in which case formula (QL), (Q-1) to (Q-44) or (H The substituent R ¹ in the structures of -1) to (H-26) should be replaced by an R ² group.

The present invention additionally provides compounds comprising at least one structure of formula (V), preferably compounds of formula (V),

wherein the symbols X and W have the definitions given above, especially for formula (I), and KonAr denotes having two, preferably three, fused aromatic or heteroaromatic rings and having from 10 to 60 aromatic ring atoms , preferably an aromatic or heteroaromatic ring system of 12 to 40 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by ^one or more R groups, wherein the KonAr group may be Forms a ring system with at least one Ar group, R group, X group or another group, wherein KonAr is preferably selected from formulae (Ar-1) to (Ar-17) and (Ar'- 1) Groups to (Ar'-17), more preferably selected from groups of formulae (Ar-3) to (Ar-17) and (Ar'-3) to (Ar'-17) as defined above .

In another preferred embodiment, it is practicable that the compounds of the present invention comprise structures of formula (VIa), (VIb) and/or (VIc), wherein the compounds of the present invention may be more preferably selected from formula (VIa) , (VIb) and/or (VIc) compounds:

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and KonAr has the above, especially for formula (V) is defined as given, and preferably is a group selected from formulae (Ar-1) to (Ar-17) and (Ar'-1) to (Ar'-17) as defined above, more preferably Groups selected from formulae (Ar-3) to (Ar-17) and (Ar'-3) to (Ar'-17) as defined above.

In addition, particular preference is given to compounds of the invention having the structures of formula (V), (VIa), (VIb) and/or (VIc), said compounds having the following properties:

In this context, compounds of formula Ar-5 or Ar'-5 in compounds having the structures of formula (V), (VIa), (VIb) and/or (VIc) detailed in the tables presented above The group comprises an R ¹ group, which preferably represents ^an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, said aromatic or each of the heteroaromatic ring systems may be substituted with one or more non-aromatic R ² groups; preferably, having the formulae (V), (VIa), (VIb detailed in the tables shown above ) and/or the compound of the structure of (VIc), the group of formula Ar-5 or Ar'-5 has at least one R ¹ group selected from formula (R ^{1 -1} ) to ( R ¹ -43), preferably groups of formulae R ¹ -1 to R ¹ -28 and R ¹ -34 to R ¹ -38, especially preferred formulae R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ¹ -13, R ¹ -14, R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ^A group of ^1-21 , R1-22, ^R1-24 and/or ^R1-37 . These R ¹ groups, preferably representing aromatic or heteroaromatic ring systems having 6 to 18 aromatic ring atoms, are preferably the attachment of the L ¹ groups in formula (Ar-5) or formula (Ar'-5) The para position of the site, denoted p=1, and the R ¹ group preferably represents an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms.

In a preferred configuration, the compounds of the present invention may comprise at least one structure of formula (VIb-1) and/or (VIb-2), preferably selected from formula (VIb-1) and/or (VIb-2) compound of,

wherein the X and R groups have the definitions given above, especially for formula (I), the designations m are the same or different and are 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, particularly preferably 0 or 1, and the ring KON means having two, preferably three, fused aromatic or heteroaromatic rings and having 10 to 60 aromatic ring atoms, preferably 12 to 40 aromatic ring atoms Aromatic or heteroaromatic ring systems of aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by ^one or more R groups, wherein R may have the above, especially for formula ( ^I ) given the definition.

It is also possible that the ring KON shown in formula (VIb-1) and/or (VIb-2) is bonded to the ring having two nitrogen atoms via adjacent carbon atoms, so that the ring fused to ring KON is 5-membered ring. The ring KON in formula (VIb-1) and/or (VIb-2) is fused to the ring through two nitrogen atoms.

It is also possible that the ring KON in the structures of formula (VIb-1) and/or (VIb-2) forms substructures of formulae (KON-1) to (KON-10),

wherein X' is N or CR ¹ , preferably CR ¹ , wherein R ¹ may have the definitions given above, especially for formula (I), and the nitrogen atoms are each in the position indicated by o with 5 to 60 carbons Aromatic or heteroaromatic ring systems of atoms combine to form a ring.

It is also possible that the ring KON in the structures of formula (VIb-1) and/or (VIb-2) forms substructures of formulae (KON'-1) to (KON'-10),

wherein R ¹ has the definitions given above, especially for formula (I), the reference o is 0, 1 or 2, preferably 0 or 1, and the reference n is 0, 1, 2 or 3, preferably 0, 1 or 2 , and the label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the nitrogen atoms are each bound to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the position identified by o to form a ring.

In another preferred embodiment, it is possible that the compounds of the present invention comprise structures of formulae (VIb-3) to (VIb-10), wherein the compounds of the present invention are more preferably selected from the group consisting of formulae (VIb-3) to (VIb-10) Compounds of (VIb-10):

wherein the symbols R and R ¹ have the definitions given above, especially for formula (I), the symbol s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, More preferably 0, 1 or 2, label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, label n is 0, 1, 2 or 3, preferably 0, 1 or 2, label 1 is 0 , 1 or 2.

With regard to the structures of formulae (VIb-1) to (VIb-8), the preferred features detailed above for the structures/compounds of formula (I) apply. This is especially true of the R group. The structures of formulae (VIb-1) to (VIb-8) may more preferably have hole transport and/or hole conductor groups as defined above.

Also particularly preferred are the compounds of the invention having the structures of formulae (VIb-1) to (VIb-8) which have the following properties:

In this context, the groups of formulae Q-11 to Q-25 in compounds having the structures of formulae (VIb- ¹ ) to (VIb-8) detailed in the tables shown above comprise the R1 group, The R ¹ group preferably represents an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, in which Each may be substituted with one or more non ^- aromatic R2 groups; preferably, compounds of formulae Q-11 to Q-25 in compounds having the structure of formula (IVa) detailed in the table shown above The group has at least one R ¹ group, preferably at least two R ¹ groups selected from formulae (R ^{1 -1} ) to (R ¹ -43), preferably formula R ¹ -1 to R ¹ -28 and R ¹ -34 to R ¹ -38 groups, particularly preferably the formulae R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ¹ -13, R ¹ -14, R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ¹ -24 and /or a group of R ¹ -37.

The present invention further provides a compound comprising at least one structure of formula (VII), preferably a compound of formula (VII):

wherein the symbols Ar and W have the definitions given above, especially for formula (I), and the ring KON denotes having two, preferably three, fused aromatic or heteroaromatic rings and having from 10 to 60 aromatic rings Ring atoms, preferably aromatic or heteroaromatic ring systems of ¹² to 40 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by ^one or more R groups, wherein R may have Above, in particular the definitions given for formula (I).

It is also possible that the ring KON shown in formula (VII) is bonded to a five-membered ring having W and SO ₂ groups via adjacent carbon atoms, so that the ring fused to ring KON is a five-membered ring. The ring KON in formula (VII) is fused to a ring having W and SO ₂ groups.

It is also possible that the ring KON in the structure of formula (VII) forms the formulae (KON-1) to (KON-10) and/or the formulae (KON'-1) to (KON'-10) as detailed above ), wherein the W or SO ₂ group is in each case bound to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the position identified by o to form a ring.

In another preferred embodiment, it is feasible that the compounds of the present invention comprise structures of formulae (VII-1) to (VII-10), wherein the compounds of the present invention may be more preferably selected from formula (VII-1) Compounds to (VII-10):

wherein the symbols R ¹ and Ar have the definitions given above, especially for formula (I), the designation s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, More preferably 0, 1 or 2, label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, label n is 0, 1, 2 or 3, preferably 0, 1 or 2, label 1 is 0 , 1 or 2.

With regard to the structures of formulae (VII) and (VII-1) to (VII-10), the preferred features detailed above for the structures/compounds of formula (I) apply. This is especially true for W and Ar groups. The structures of formulae (VII) and (VII-1) to (VII-10) may more preferably have hole transport and/or hole conductor groups as defined above.

Also particularly preferred are the compounds of the invention having the structures of the formulae (VII) and (VII-1) to (VII-10), said compounds having the following properties:

In the present context, the groups of formulae Q-11 to Q-25 in compounds having the structures of formulae (VII) and (VII-1) to (VII-10) detailed in the tables shown above comprise R ¹ group, which preferably denotes an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, each of said aromatic or heteroaromatic ring systems may be substituted by one or more non ^- aromatic R2 groups; preferably, groups of formulae Q-11 to Q-25 in compounds having the structure of formula (IVa) detailed in the table shown above group has at least one R ¹ group, preferably at least two R ¹ groups, the R ¹ group is selected from formulae (R ¹ -1) to (R ¹ -43), preferably formula R ¹ -1 to R ¹ -28 and R ¹ -34 to R ¹ -38 groups, particularly preferred formulae R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ^1-13 , ^R1-14 , ^R1-16 , ^R1-17 , ^R1-18 , ^R1-19 , ^R1-20 , ^R1-21 , ^R1-22 , ^R1-24 and/ or the group of R ¹ -37.

The present invention also provides compounds comprising at least one structure of formula (VIII), preferably a compound of formula (VIII):

wherein the symbols X, Ar and W have the definitions given above, especially for formula (I), wherein the structure/compound has at least one aromatic or heteroaromatic ring system, said aromatic or heteroaromatic ring The system has 5 to 60 carbon atoms and is fused to a non-aromatic or non-heteroaromatic ring system.

It is preferably possible that the non-aromatic or non-heteroaromatic ring system fused to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms is a non-aromatic or non-heteroaromatic ring system having at least 2 rings, preferably at least 3 rings Aromatic or non-heteroaromatic polycyclic ring systems.

It is preferably possible that a non-aromatic or non-heteroaromatic ring system fused to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms is bonded to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms Two adjacent ring atoms of an aromatic ring system, preferably carbon atoms. Thus, the binding sites of the non-aromatic or non-heteroaromatic ring system are preferably arranged ortho-positioned relative to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms.

It is also possible that non-aromatic or non-heteroaromatic ring systems fused to aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms are formed by preferably adjacent at least two R groups. The at least two groups may be provided by the X group and/or the substituent R combined with the Ar group, wherein Ar may be combined with the nitrogen atom shown in formula (VIII) and via the W group (C=N -Ar) binding.

In this context, in structures/compounds of formula (VIII), it is possible that at least two, preferably adjacent, R groups form together with a further group to which the two R groups are bound a fused ring, wherein the two R groups form at least one structure of formulae (RA-1) to (RA-12):

wherein R has the definitions given above, especially for formula ( ^I ), the dashed bond represents the point of attachment to the atom of the group to which the two R groups are bound, and the further symbols have the following definitions:

Y ⁴ is the same or different in each case and is C(R ¹ ) ₂ , (R ¹ ) ₂ CC(R ¹ ) ₂ , (R ¹ )C=C(R ¹ ), NR ¹ , NAr′, O or S, preferably C(R ¹ ) ₂ , (R ¹ ) ₂ CC(R ¹ ) ₂ , (R ¹ )C=C(R ¹ ), O or S;

^Ra is the same or different in each case and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or an alkane having 2 to 40 carbon atoms or alkenyl group, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy group An oxy, alkenyl or alkynyl group may in each case be substituted by one or more R ² groups, wherein one or more non-adjacent CH ₂ groups may be replaced by R ² C=CR ² , C ≡C, Si(R ² ) ₂ , C=O, C=S, C=Se, C=NR ² , -C(=O)O-, -C(=O)NR ² -, NR ² , P (=O)(R ¹ ), -O-, -S-, SO or SO ₂ , or having 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R ² groups an aromatic or heteroaromatic ring system, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups; meanwhile, ^two R ^a Groups can also form together a ring system;

s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2;

t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2;

v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2.

It is also possible that at least two of the R groups forming the structures of formulae (RA-1) to (RA-12) and forming the fused ring are R groups from adjacent X groups.

In a preferred embodiment of the present invention, at least two R groups, together with a further group to which the two R groups are bound, form a fused ring, wherein the two R groups preferably form the formula (RA-1a ) to at least one of the structures of (RA-4f):

where the symbols R ^a and R ¹ and the symbols s and t have the definitions given above, especially for formulae (RA-1) to (RA-12), the dashed bond indicates the attachment site, and the symbols m are 0, 1 , 2, 3 or 4, preferably 0, 1 or 2.

In a further preferred configuration, at least two R groups form a fused ring together with another group to which the two R groups are bound, wherein the two R groups form a structure of formula (RB):

wherein R ¹ has the definitions described above, especially for formula (I), the dashed bond represents the site of attachment, the label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y ⁵ is C(R ¹ ) ₂ , NR ¹ , NAr, O or S, preferably C(R ¹ ) ₂ , NAr or O.

It is possible here that at least two of the R groups forming the structure of formula (RB) and forming the fused ring are R groups from adjacent X groups.

It is also possible that the at least two R groups forming the structure of ^formula (RB) and forming the fused ring R groups are adjacent, especially in an ortho position such that the ring is together with the Y group is a 5-membered ring.

In another preferred embodiment, it is practicable that the compounds of the present invention comprise structures of formulae (VIII-1) to (VIII-13), wherein the compounds of the present invention may be more preferably selected from formula (VIII-1) A compound to (VIII-13), wherein the compound has at least one fused ring:

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the designation n is 0, 1, 2 or 3, preferably 0, 1 or 2, the notation 1 is 0, 1 or 2, and the notation o denotes the attachment site of the fused ring.

Condensed rings, especially in formulae (VIII) and (VIII-1) to (VIII-13), preferably from formulae (RA-1) to (RA-12), formulae (RA-1a) to (RA-4f) ) and/or at least one of the structures of formula (RB) is formed together with a ring atom marked by the symbol o, with particular preference being given to formulae (RA-1) to (RA-12), formulae (RA-1a) to (RA -4f) structure.

With regard to the structures of formulae (VIII) and (VIII-1 ) to (VIII-13), the preferred features detailed above for the structures/compounds of formula (I) apply. This is especially true for W and Ar groups. The structures of formulae (VIII) and (VIII-1) to (VIII-13) may more preferably have hole transport and/or hole conductor groups as defined above.

Also particularly preferred are compounds of the invention having the structures of the formulae (VIII) and (VIII-1) to (VIII-13), said compounds having the following properties:

In this context, groups of formulae Q-11 to Q-25 in compounds of formulae (VIII) and (VIII-1) to (VIII-13) detailed in the tables presented above comprise R ¹ group, said R ¹ group preferably represents an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, said aromatic or heteroaromatic ring system Each of the ring systems may be substituted with one or more non-aromatic R ² groups; preferably, compounds of formula Q-11 to The group of Q-25 has at least one R ¹ group, preferably at least two R ¹ groups, the R ¹ group is selected from formulae (R ¹ -1) to (R ¹ -43), preferably formula R ¹ -1 to R ¹ -28 and R ¹ -34 to R ¹ -38, particularly preferably the formulae R ¹ -1, R ¹ -3, R ¹ -4, R ¹ -10, R ¹ -11, R ¹ -12, R ¹ -13, R ¹ -14, R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ^1-24 and/or R ^1-37 groups.

The invention furthermore provides structures comprising exactly two, exactly three or exactly four formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) and/or the same Preferred embodiments, especially formulae (III), (IVa) to (IVc), (V), (VIa) to (VIc), (VII), (VII-1 ) to (VII-10), (VIII) , (VIII-1) to (VIII-10) of the structure of the compound.

More preferably, the compound is selected from compounds of formulae (IXa) to (IXc):

wherein the symbols Ar and W have the definitions given above, especially for formula ( ^I ), X is N, CR, and if the L group is bound to X, X is C, provided that there are not more than two in a ring and L ¹ represents a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, aromatic ring atoms and which may be substituted by one or more R ¹ groups, wherein L ¹ is preferably a bond or a group selected from formulae (L ¹ -1) to (L ¹ -76) as defined above, wherein, in formula (VIIa), the L ¹ group is more preferably not a bond .

More preferably, the compound is selected from compounds of formulae (Xa) to (Xc):

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation m is 0, 1, 2, 3 or 4, preferably 0, ¹ or 2, and L has the above, especially The definitions given for formulae (IXa) to (IXc) are preferably selected from the groups of formulae (L ¹ -1) to (L ¹ -76) defined above, wherein in formulae (IXa) to ( In IXc), the L ¹ group is more preferably not a bond.

More preferably, the compound is selected from compounds of formulae (XIa) to (XIc):

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation n is 0, 1, 2 or 3, preferably 0, 1 or 2, the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and L ¹ has the definitions given above, especially for formulae (IXa) to (IXc), and is preferably selected from the above-defined formulae (L ¹ -1) to ( L ¹ -76) group.

More preferably, the compound is selected from compounds of formulae (XIIa) to (XIIc):

wherein the symbols R and Ar have the definitions given above, especially for formula (I), the designation n is 0, 1, 2 or 3, preferably 0, 1 or 2, the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and L ¹ has the definitions given above, especially for formulae (IXa) to (IXc), and is preferably selected from the above-defined formulae (L ¹ -1) to ( L ¹ -76) group.

In a preferred configuration, the compounds of the present invention may comprise at least one structure of formula (XIII-1) and/or (XIII-2), preferably selected from formula (XIII-1) and/or (XIII-2) compound of:

wherein the X and R groups have the definitions given above, especially for formula (I), the designations m are the same or different and are 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, especially preferably 0 or 1, the designation z is 2, 3 or 4, and the ring AR ⁿ is an aromatic ring having 5 to 60 aromatic ring atoms which may be substituted by one or more R ¹ groups or a heteroaromatic ring system, wherein R ¹ may have the definitions given above, especially for formula (I).

Preferably, the ring AR ⁿ is an aromatic or heteroaromatic having two, preferably three, fused aromatic or heteroaromatic rings and having 10 to 60 aromatic ring atoms, preferably 12 to 40 aromatic ring atoms family ring system.

It is also possible that the ring AR ⁿ shown in formula (XIII-1) and/or (XIII-2) is bonded to the ring having two nitrogen atoms via adjacent carbon atoms, so that the ring fused to the ring KON The ring is a 5-membered ring. Ring AR ⁿ in formula (XIII-1) and/or (XIII-2) is fused to the ring through two nitrogen atoms.

It is also possible that the ring AR ⁿ in the structure of formula (XIII) forms substructures of formulae (AR ⁿ -1) to (AR ⁿ -29):

wherein X' is N or CR ¹ , preferably CR ¹ , wherein R ¹ may have the definitions given above, especially for formula (I), U is selected from O, S, C(R ¹ ) ₂ , N(R ¹ ), B(R ¹ ), Si(R ¹ ) ₂ , C=O, S=O, SO ₂ , P(R ¹ ) and P(=O)R ¹ , and the W or SO ₂ groups are each in The position identified by o binds to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to form a ring.

It is also possible that ring AR ⁿ in the structure of formula (XIII) forms substructures of formulae (AR ^nl -1) to (AR ^nl -30),

wherein X' is N or CR ¹ , preferably CR ¹ , wherein R ¹ may have the definitions given above, especially for formula (I), U is selected from O, S, C(R ¹ ) ₂ , N(R ¹ ), B(R ¹ ), Si(R ¹ ) ₂ , C=O, S=O, SO ₂ , P(R ¹ ) and P(=O)R ¹ , marked o as 0, 1 or 2, Preferably 0 or 1, label n is 0, 1, 2 or 3, preferably 0, 1 or 2, label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and label 1 is 0, 1 , 2, 3, 4, 5 or 6, preferably 0, 1 or ₂ , and the W or SO groups are each bound to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the position identified by o to form a ring.

It is also possible that, in formulae (AR ^nl -1) to (AR ^nl -30), the sum of the labels o, n, m and l is not greater than 6, preferably not greater than 4 and more preferably not greater than 2.

With regard to the structures of formula (XIII-1) and (XIII-2), the preferred features detailed above for the structures/compounds of formula (I) apply. This is especially true of the R group. The structures of formulae (XIII-1) and (XIII-2) may more preferably have hole transport and/or hole conductor groups as defined above.

Also particularly preferred are compounds of the invention having the structures of formulae (XIII-1) and (XIII-2), said compounds having the following properties:

In this context, the groups of formulae Q-11 to Q-25 in compounds having the structures of formulae (XIII- ¹ ) and (XIII-2) detailed in the tables presented above comprise the R1 group, It preferably denotes an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, each of said aromatic or heteroaromatic ring systems may be replaced by a or more non-aromatic R ² groups; preferably, the groups of formulae Q-11 to Q-25 in the compound having the structure of formula (IVa) detailed in the table shown above have at least one R ¹ group, preferably at least two R ¹ groups selected from formulae (R ^{1 -1} ) to (R ¹ -43), preferably formulae R ¹ -1 to R ¹ -28 and R Groups from ^1-34 to R ^1-38 , particularly preferred formulae R ^1-1 , R ^1-3 , R ^1-4 , R ^1-10 , R ^1-11 , R ^1-12 , R ^1-13 , R ¹ -14, R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ¹ -24 and/or R ¹ - 37 groups.

The present invention also provides a compound of formula (XIV):

wherein the symbols Ar and W have the definitions given above, especially for formula (I), the designation z is 2, 3 or 4, and the ring AR ⁿ is a ring having 5 to 60 aromatic ring atoms and may be formed by one or more Aromatic or heteroaromatic ring systems substituted with R ¹ groups, wherein R ¹ may have the definitions given above, especially for formula (I).

It is also possible that the ring AR ⁿ in the structure of formula (XIV) forms the formulae (AR ⁿ -1 ) to (AR ⁿ -29) and/or the formulae (AR ^nl -1 ) to (AR as detailed above ^nl -30) in which the W or SO ₂ group is in each case bound to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the position identified by o to form a ring.

It is also possible that the ring AR ⁿ in the structure of formula (XIV) is bonded to a five-membered ring with W and SO ₂ groups via adjacent carbon atoms, so that in the structure of formula (XIV) the ring AR ^{n is} fused The closed ring is a 5-membered ring. The ring KON in _formula (XIV) is fused to a ring having W and SO2 groups.

With regard to the structure of formula (XIV), the preferred features detailed above for the structure/compound of formula (I) apply. This is especially true for W and Ar groups. The structures of formula (XIV) may more preferably have hole transport and/or hole conductor groups as defined above.

In addition particular preference is given to compounds of the invention having the structure of formula (XIV), said compounds having the following properties:

In the present context, the groups of formulae Q-11 to Q-25 in the compounds having the structures of formula (XIV) detailed in the table shown above comprise the R ¹ group, which preferably represents ^a group having 6 to 18 aromatic ring atoms, preferably aromatic or heteroaromatic ring systems having from 6 to 13 aromatic ring atoms, each of which may be replaced by one or more non-aromatic ring systems Group R ² groups are substituted; preferably, the groups of formulae Q-11 to Q-25 in the compounds having the structures of formula (IVa) detailed in the tables shown above have at least one R ¹ group, Preferably at least two R ¹ groups selected from the group consisting of formulae (R ^{1 -1} ) to (R ¹ -43), preferably formulae R ¹ -1 to R ¹ -28 and R ¹ -34 to R ^1-38 groups, especially preferred formulae R ^1-1 , R ^1-3 , R ^1-4 , R ^1-10 , R ^1-11 , R ^1-12 , R ^1-13 , R ^1-14 , A group of R ¹ -16, R ¹ -17, R ¹ -18, R ¹ -19, R ¹ -20, R ¹ -21, R ¹ -22, R ¹ -24 and/or R ¹ -37.

Preferred embodiments of the compounds of the invention are detailed in the examples, and these compounds can be used alone or in combination with further compounds for all purposes of the invention.

The above-described preferred embodiments can be combined with each other as necessary as long as the conditions stated in claim 1 are satisfied. In a particularly preferred embodiment of the present invention, the preferred embodiments described above apply simultaneously.

The compounds of the invention can in principle be prepared by various methods. However, the method described below has been found to be particularly suitable.

Accordingly, the present invention also provides a process for the preparation of a compound of the present invention, preferably a compound comprising a structure of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4), Therein, in a coupling reaction, a compound comprising at least one benzisothiazole group is linked with a compound comprising at least one aromatic or heteroaromatic group.

Suitable compounds comprising at least one heterocyclic structure are in many cases commercially available, and the starting compounds detailed in the examples can be obtained by known methods, to which reference is therefore made.

These compounds can be reacted with further compounds comprising at least one aromatic or heteroaromatic group by known coupling reactions, the necessary conditions for this purpose are known to those skilled in the art and detailed in the Examples It is helpful for those skilled in the art to carry out these reactions.

All particularly suitable and preferred coupling reactions leading to C-C bond formation and/or C-N bond formation are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are widely known and the examples will provide further guidance to those skilled in the art.

The principles of the preparation methods detailed above are in principle known from the literature for analogous compounds and can be readily adapted by those skilled in the art for the preparation of the compounds of the present invention. Additional information can be found in the Examples.

By these methods, purification, eg recrystallization or sublimation, is necessary, to obtain compounds of the invention comprising structures of formula (I) in high purity, preferably greater than 99% (determined by ¹ H NMR and/or HPLC).

The compounds of the present invention may also have suitable substituents, such as longer alkyl groups (about 4 to 20 carbon atoms), especially branched alkyl groups, or optionally substituted aryl groups, such as A xylyl, mesityl or branched terphenyl or tetraphenyl group which results in solubility in standard organic solvents such that the compound is soluble in sufficient concentrations in toluene or xylene at room temperature, in order to be able to process the compound from solution. These soluble compounds are particularly well suited for processing from solution, eg by printing methods. Furthermore, it should be emphasized that structures comprising at least one of the formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) and their preferred implementations shown in further structures Compounds of the present invention in this manner have enhanced solubility in these solvents.

Additionally, the compounds of the present invention may contain one or more crosslinkable groups. "Crosslinkable group" refers to a functional group capable of irreversible reaction. This forms an insoluble cross-linked material. Crosslinking can generally be facilitated by heating or by UV radiation, microwave radiation, x-radiation or electron beams. In this case, almost no by-products are formed during the crosslinking. In addition, the crosslinkable groups that may be present in the functional compound are very easy to crosslink so that a relatively small amount of energy is required for crosslinking (eg <200°C in the case of thermal crosslinking).

Examples of crosslinkable groups are units containing double bonds, triple bonds, precursors capable of forming double or triple bonds in situ, or heterocyclic addition polymerizable groups. Crosslinkable groups include vinyl, alkenyl, preferably vinyl and propenyl, C _4-20 cycloalkenyl, azide, ethylene oxide, oxetane, bis(hydrocarbyl)amino, cyanate ester, hydroxyl, glycidyl ether, C _1-10 alkyl acrylate, C _1-10 alkyl methacrylate, alkenyloxy, preferably vinyloxy, perfluoroalkenyloxy, preferably perfluorovinyloxy, Alkynyl, preferably ethynyl, maleimide, cyclobutylphenyl, tris(C _1-4 )-alkylsiloxy and tris(C _1-4 )-alkylsilyl. Cyclobutylphenyl, vinyl and alkenyl are particularly preferred.

The compounds of the present invention can also be mixed with polymers. It is also possible to covalently incorporate these compounds into polymers. Compounds substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acids or boronic esters, or with reactive polymerizable groups such as alkenes or oxetanes are particularly feasible. These can be used as monomers for the preparation of the corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably effected via halogen functional groups or boronic acid functional groups or via polymerizable groups. The polymers can additionally be crosslinked via such groups. The compounds and polymers of the present invention can be used in the form of crosslinked or uncrosslinked layers.

Accordingly, the present invention also provides structures comprising one or more of the above-detailed structures of formulae (I), (IIa) to (IIc) and/or (IIb-1 ) to (IIb-4) or compounds of the invention Oligomers, polymers or dendrimers wherein one or more of the compounds of the invention or structures of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) are present a linkage to the polymer, oligomer or dendrimer. Depending on the structures of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or the linkages of the compounds, these thus form oligomers or polymer side chains or Bonded within the main chain. The polymer, oligomer or dendrimer may be conjugated, partially conjugated or non-conjugated. The oligomer or polymer may be linear, branched or dendritic. The same preferred features as described above apply to the repeating units of the compounds of the invention in oligomers, dendrimers and polymers.

To prepare the oligomers or polymers, the monomers of the present invention are homopolymerized or copolymerized with further monomers. Preference is given to copolymers in which the units of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or the preferred embodiments described above and below are in the range from 0.01 to 99.9 It is present in a range of mol%, preferably 5 to 90 mol%, more preferably 20 to 80 mol%. Suitable and preferred comonomers forming the basic backbone of the polymer are selected from fluorene (eg according to EP 842208 or WO 2000/022026), spirobifluorene (eg according to EP 707020, EP 894107 or WO 2006/061181), p-benzene subunit (eg according to WO 92/18552), carbazole (eg according to WO 2004/070772 or WO 2004/113468), thiophene (eg according to EP 1028136), dihydrophenanthrene (eg according to WO 2005/014689) , cis- and trans-indenofluorenes (eg according to WO 2004/041901 or WO 2004/113412), ketones (eg according to WO 2005/040302), phenanthrenes (eg according to WO 2005/104264 or WO 2007/017066) or more plant these units. The polymers, oligomers and dendrimers may also contain additional units, such as hole transport units, especially those based on triarylamines, and/or electron transport units.

Also of particular interest are compounds of the invention having high glass transition temperatures. Especially preferred in this regard are compounds comprising the structures of formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or the preferred embodiments described above and below , which has a glass transition temperature 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, measured according to DIN 51005 (2005-08 edition).

烷，苯氧基甲苯，尤其是3-苯氧基甲苯，(-)-葑酮，1,2,3,5-四甲基苯，1,2,4,5-四甲基苯，1-甲基萘，2-甲基苯并噻唑，2-苯氧基乙醇，2-吡咯烷酮，3-甲基苯甲醚，4-甲基苯甲醚，3,4-二甲基苯甲醚，3,5-二甲基苯甲醚，苯乙酮，α-萜品醇，苯并噻唑，苯甲酸丁酯，异丙苯，环己醇，环己酮，环己基苯，十氢化萘，十二烷基苯，苯甲酸乙酯，茚满，NMP，对甲基异丙基苯，苯乙醚，1,4-二异丙基苯，二苄醚，二乙二醇丁基甲基醚，三乙二醇丁基甲基醚，二乙二醇二丁基醚，三乙二醇二甲基醚，二乙二醇单丁基醚，三丙二醇二甲基醚，四乙二醇二甲基醚，2-异丙基萘，戊苯，己苯，庚苯，辛苯，1,1-双(3,4-二甲基苯基)乙烷，2-甲基联苯，3-甲基联苯，1-甲基萘，1-乙基萘，辛酸乙酯，癸二酸二乙酯，辛酸辛酯，庚苯，异戊酸薄荷酯，己酸环己酯或这些溶剂的混合物。In order to process the compounds of the invention from the liquid phase, eg by spin coating or by printing methods, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF , THP, Chlorobenzene, Di

Alkane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1 -methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole , 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin , dodecylbenzene, ethyl benzoate, indan, NMP, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, Triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether , 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methyl Biphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl caprylate, diethyl sebacate, octyl caprylate, heptylbenzene, menthyl isovalerate, cyclohexyl caproate or mixtures of these solvents.

Accordingly, the present invention also provides formulations or compositions comprising at least one compound of the present invention and at least one additional compound. Said additional compound may, for example, be a solvent, especially one of the abovementioned solvents or a mixture of these solvents. If the additional compound contains a solvent, the mixture is referred to herein as a formulation. Alternatively, the further compound may be at least one further organic or inorganic compound which is also used in electronic devices, eg a light-emitting compound and/or a further matrix material. Suitable light-emitting compounds and additional host materials in connection with organic electroluminescent devices are listed below. The additional compound may also be polymeric.

Accordingly, the present invention additionally provides a composition comprising a combination comprising the following compounds:

A) one or more compounds comprising at least one structure of formula (I), preferably one or more compounds of formula (I),

wherein the symbols X, W and Ar have the definitions given above, especially for formula (I);

B) additional compounds selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, exciton blocking materials, electron injection materials, electron transport materials, electron blocking materials, Hole injecting materials, hole conducting materials, hole blocking materials, n-type dopants, p-type dopants, wide bandgap materials and/or charge generating materials.

The present invention also provides a composition comprising at least one structure or The compounds of the preferred embodiments described above and below, as well as at least one wide bandgap material, are understood to mean materials within the meaning of the disclosure of US 7,294,849. These systems exhibit particularly favorable performance data in electroluminescent devices.

Preferably, the additional compound may have a band gap of 2.5 eV or more, preferably 3.0 eV or more, very preferably 3.3 eV or more. One way to calculate the band gap is via the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

The molecular orbitals of the material, in particular the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels as well as the energy of the lowest triplet state T ₁ and the lowest excited singlet state S ₁ are determined via quantum chemical calculations energy of. To calculate metal-free organic substances, geometry optimization is first performed by the "ground state/semi-empirical/default spin/AM1/charge 0/spin singlet state" method. Subsequently, energy calculations are implemented based on the optimized geometry. This was done using the "TD-SCF/DFT/default spin/B3PW91" method with the "6-31G(d)" basis set (charge 0, spin singlet). For metal-containing compounds, the geometry was optimized via the "ground state/Hartrey-Fock/default spin/LanL2MB/charge 0/spin singlet" method. The energy calculations are carried out similarly to the method described above for organic substances, except that the "LanL2DZ" basis set is used for the metal atoms and the "6-31G(d)" basis set is used for the ligands. The HOMO energy level HEh or the LUMO energy level LEh in Hartree units is obtained from the energy calculation. This is used to determine the HOMO and LUMO levels in electron volts calibrated by 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 this application, these values are considered to be the HOMO and LUMO levels of the material.

The lowest triplet state T ₁ is defined as the triplet state energy with the lowest energy apparent from the quantum chemical calculations.

The lowest excited singlet state S ₁ is defined as the excited singlet state energy with the lowest energy apparent from the quantum chemical calculations.

The method described here is independent of the software package used and always gives the same results. Examples of commonly used programs for this purpose are "Gaussian09W" (Gauss) and Q-Chem 4.1 (Q-Chem).

The present invention also relates to a composition comprising at least one structure comprising formulae (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or the above and The compounds of the preferred embodiments described below and the at least one phosphorescent emitter, the term "phosphorescent emitter" should also be understood to mean a phosphorescent dopant.

A dopant in a system comprising a matrix material and a dopant is understood to mean a component with a smaller proportion in the mixture. Correspondingly, matrix material in a system comprising matrix material and dopant is to be understood as meaning the components having a larger proportion in the mixture.

Preferred phosphorescent dopants for use in matrix systems, preferably mixed matrix systems, are the preferred phosphorescent dopants specified below.

The term "phosphorescent dopant" generally encompasses compounds in which luminescence is achieved by spin-forbidden transitions, such as transitions from an excited triplet state or a state with a higher spin quantum number, such as a quintet state.

Suitable phosphorescent compounds (=triplet emitters) are in particular compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than Atoms of 56 and less than 80, especially compounds of metals with this atomic number. Preferred phosphorescent emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.

Examples of the abovementioned illuminants can be found in the following applications: WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/10202629, WO 2010/10202620 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/1040185, WO 2015/1040185, WO 2015/104018 2016/015815, WO 2016/124304, WO 2017/032439, WO 2018/011186, WO 2018/001990, WO 2018/019687, WO 2018/019688, WO 2018/041769, WO 2018/054796, WO 2018/0561998 2018/069197, WO 2018/069273, WO 2018/178001, WO 2018/177981, WO 2019/020538, WO 2019/115423, WO 2019/158453 and WO 2019/179909. In general, all phosphorescent complexes for phosphorescent electroluminescent devices according to the prior art and known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art will be able to Additional phosphorescent complexes are used with creative effort.

Examples of phosphorescent dopants are listed in the table below:

When the compound used according to the invention is used as matrix material for phosphorescent compounds in the light-emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters). Phosphorescence in the context of the present invention is understood to mean light emission from excited states with higher spin multiplicity, ie spin states >1, in particular from excited triplet states. In the context of the present application, all luminescent complexes containing transition metals or lanthanides, in particular all iridium, platinum and copper complexes, are to be regarded as phosphorescent compounds.

The mixture of compound and luminescent compound used according to the invention contains between 99% and 1% by volume, preferably between 98% and 10% by volume, more preferably between 99% and 10% by volume, based on the total mixture of emitter and matrix material. Between 97% and 60% by volume and especially between 95% and 80% by volume of the compounds of the invention. Accordingly, based on the total mixture of emitter and host material, the mixture contains between 1% and 99% by volume, preferably between 2% and 90% by volume, more preferably between 3% and 3% by volume. Between 40% by volume and in particular between 5% and 20% by volume of the emitter.

In one embodiment of the invention, the compound used according to the invention is used here as the sole matrix material ("single host") for the phosphorescent emitter.

In a preferred embodiment of the present invention, the organic electroluminescent device contains a compound used according to the present invention, preferably comprising the formulae (I), (IIa) to (IIc) and/or (IIb-1) to ( The structure of IIb-4) or the compounds of the preferred embodiments detailed above as matrix material in one or more light-emitting layers, preferably as electron-conducting matrix material, preferably in combination with further matrix materials, preferably hole-conducting matrix materials . In another preferred embodiment of the present invention, the further matrix material is an electron transport compound. In yet another preferred embodiment, the further host material is a compound with a large band gap, which, if it does participate in hole and electron transport in the layer, does not participate in hole and electron transport to a significant extent. The light-emitting layer contains at least one light-emitting compound.

In another particularly preferred embodiment of the present invention, the organic electroluminescent device of the present invention comprises in the hole-transport layer or electron-transport layer the compound used according to the present invention, preferably comprising the formulae (I), (IIa) to The structures of (IIc) and/or (IIb-1) to (IIb-4) or compounds of the preferred embodiments detailed above.

Accordingly, the present invention also relates to a composition comprising at least one compound used according to the invention, preferably comprising the formulae (I), (IIa) to (IIc) and/or (IIb-1) to ( The structure of IIb-4) or a compound of the preferred embodiments described above and below, and at least one additional matrix material.

Suitable matrix materials which can be used in combination with compounds of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or according to preferred embodiments are aromatic ketones, aromatic oxides Phosphine or aromatic sulfoxides or sulfones, eg according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680; triarylamines, carbazole derivatives, eg CBP(N,N-biscarbazole) azolylbiphenyl) or carbazole derivatives disclosed in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176; indolocarbazole derivatives, For example according to WO 2007/063754 or WO 2008/056746; indenocarbazole derivatives, for example according to WO 2010/136109, WO2011/000455, WO 2013/041176 or WO 2013/056776; azacarbazole derivatives, for example according to EP1617710, EP 1617711, EP 1731584, JP 2005/347160; bipolar matrix materials, eg according to WO2007/137725; silanes, eg according to WO 2005/111172; according to WO 2006/117052; triazine derivatives, eg according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877; zinc complexes, eg according to EP652273 or WO 2009/062578; silazacyclopentane or silatetraazacyclopentane derivatives, for example according to WO2010/054729; phosphodiazepine derivatives, for example according to WO 2010/054730 bridged carbazole derivatives, eg according to WO 2011/042107, WO 2011/060867, WO 2011/088877 and WO 2012/143080; bitriphenylidene derivatives, eg according to WO 2012/048781; dibenzos Furan derivatives, eg according to WO 2015/169412, WO2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565; or biscarbazoles, eg according to JP 3139321B2; lactams, eg according to WO 2011/ 116865, WO 2011/137951 or WO 2013/064206; 4-spiro Carbazole derivatives, eg according to WO 2014/094963 or WO 2015/192939. Additional phosphorescent emitters that emit at a shorter wavelength than the actual emitter can likewise be present in the mixture as co-hosts.

Preferred co-host materials are triazine, quinazoline, quinoxaline, triarylamine derivatives, especially monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives .

Preference can also be given to using a plurality of different matrix materials in the form of mixtures, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Preference is likewise given to using mixtures of charge-transporting matrix materials and electrically inert matrix materials which, even if they participate in charge transport, do not significantly participate, as described, for example, in WO 2010/108579. Particularly suitable as co-host materials in combination with the compounds according to the invention are compounds which have a large band gap and which themselves do not participate in charge transport of the light-emitting layer at least to a significant extent. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or WO 2010/006680.

Furthermore, it is preferred to use a mixture of two or more triplet emitters and a host. In this case, the triplet emitter with the shorter-wave emission spectrum is used as a co-host for the triplet emitter with the longer-wave emission spectrum.

More preferably, in a preferred embodiment, compounds for use according to the invention comprising structures of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) can be found in In the light-emitting layers of organic electronic devices, especially in organic electroluminescent devices, for example in OLEDs or OLECs, they are used as matrix materials. In this case, a compound containing a compound comprising a structure of formula (I), (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or the preferred embodiments described above and below The host material is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

The proportion of matrix material in the light-emitting layer is in this case between 50.0% and 99.9% by volume for a fluorescent light-emitting layer, preferably between 80.0% and 99.5% by volume, and more preferably between 92.0% by volume between 99.5% by volume and between 85.0% and 97.0% by volume for phosphorescent light-emitting layers.

Accordingly, the proportion of dopants for the fluorescent light-emitting layer is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume, and more preferably between 0.5 and 8.0% by volume between 3.0 and 15.0 vol% for phosphorescent light-emitting layers.

The light-emitting layer of the organic electroluminescent device may also comprise a system containing multiple host materials (mixed-matrix systems) and/or multiple dopants. Also in this case, the dopants are generally those materials that have a smaller proportion in the system and the host materials are those materials that have a larger proportion in the system. In individual cases, however, the proportion of a single host material in the system may be smaller than the proportion of a single dopant.

In another preferred embodiment of the present invention, structures comprising formulae (I), (IIa) to (IIc) and/or (IIb-1 ) to (IIb-4) or preferred as described above and below The compounds of the embodiments are used as components of mixed matrix systems. The mixed matrix system preferably comprises two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, 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 components can also be combined predominantly or completely in a single mixed-matrix component, in which case the further mixed-matrix components fulfill other functions. 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. Mixed-matrix systems are preferably used in phosphorescent organic electroluminescent devices. One source of more detailed information on mixed matrix systems is application WO 2010/108579.

The present invention also provides the use of the compounds of the invention in electronic devices, especially in organic electroluminescent devices.

The invention furthermore provides the compounds used according to the invention and/or the oligomers, polymers or dendrimers according to the invention as fluorescent emitters in electronic devices, emitters exhibiting 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 and/or wide bandgap material, preferably as fluorescent emitter (singlet emitter), host Use of materials, hole transport materials and/or electron transport materials.

The invention furthermore provides an electronic component comprising at least one compound which can be used according to the invention and/or a compound according to the invention. An electronic device in the context of the present invention is a device having an anode, a cathode and at least one intermediate layer comprising at least one organic compound. The assembly may also comprise inorganic materials or layers formed entirely of inorganic materials.

The electronic device is preferably selected from the following, more preferably, the electronic device is selected from organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), preferably organic light emitting diodes (OLED), small molecule-based organic light emitting diodes (sOLED), polymer-based organic light-emitting diodes (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), organic plasmonic light-emitting devices (D.M.Koller et al., Nature Photonics 2008, 1-4 ), 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 optics Detectors, organic photoreceptors, organic field quenching devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), more preferably organic light emitting diodes (OLEDs), based on small Molecular organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), especially phosphorescent OLEDs.

The organic electroluminescent device includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, such as in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitons Blocking layers, electron blocking layers and/or charge generating layers. It is likewise possible to introduce, for example, an intermediate layer with an exciton blocking function between the two light-emitting layers. However, it should be noted that each of these layers does not necessarily have to be present. In this case, the organic electroluminescent device may contain one light-emitting layer, or it may contain a plurality of light-emitting layers. If a plurality of light-emitting layers are present, these preferably have in total a plurality of emission peaks between 380 nm and 750 nm, so that the overall result is white emission; in other words, a plurality of light-emitting compounds which can fluoresce or phosphoresce are used in the light-emitting layer. Especially preferred are systems with three emitting layers, wherein the three layers exhibit blue, green and orange or red emission. The organic electroluminescent device of the present invention may also be a tandem electroluminescent device, especially a white-emitting OLED.

In another embodiment of the present invention, the organic electroluminescent device of the present invention does not contain any separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, which means The light-emitting layer is directly adjacent to the hole injection layer or anode, and/or the light-emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode, as described for example in WO2005/053051. In addition, the same or similar metal complexes as the metal complexes in the light-emitting layer can be used as hole transport or hole injection material for the immediately adjacent light-emitting layer, as described for example in WO 2009/030981.

Depending on the exact structure, the compounds of the present invention can be used in different layers. The compounds of the formula (I) or the preferred embodiments detailed above are preferably included in the light-emitting layer as host material for phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), in particular fluorescent emitters or phosphorescent emitters of organic electroluminescent devices. In addition, the compounds of the present invention can also be used in electron transport layers and/or in hole transport layers and/or in exciton blocking layers and/or in hole blocking layers. Particular preference is given to using the compounds according to the invention as matrix materials for red, orange or yellow phosphorescent emitters, in particular red phosphorescent emitters, in emitting layers, or as electron-transporting materials or hole-blocking layers in electron-transporting layers or hole-blocking layers Material.

The present invention also provides an electronic device, preferably an organic electroluminescent device, comprising one or more compounds of the invention and/or at least one oligomer of the invention in one or more electron-conducting layers compounds, polymers, or dendrimers as electron-conducting compounds.

In the further layers, generally any material as used for said layers according to the prior art can be used, and a person skilled in the art can combine any of these materials with the material of the present invention without inventive step incorporated in electronic devices.

The components are structured accordingly (depending on the application), contact connections are provided and finally hermetically sealed, since the lifetime of these components is severely shortened in the presence of water and/or air.

Also preferred are electronic devices, in particular organic electroluminescent devices, characterized in that one or more layers are applied by a sublimation process. In this case, the material is applied by vapor deposition in a vacuum sublimation system at an initial pressure of generally less than 10 ⁻⁵ mbar, preferably less than 10 ⁻⁶ mbar. The initial pressure can also be lower or higher, eg less than ^10-7 mbar.

Equally preferred are electronic components, in particular organic electroluminescent components, characterized in that one or more layers are applied by an OVPD (Organic Vapor Deposition) method or by means of sublimation of a carrier gas. In this case, the material is applied at a pressure of 10 ⁻⁵ 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 is thus structured (eg MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

Also preferred are electronic devices, especially organic electroluminescent devices, characterized in that they are characterized from solution, for example by spin coating, or by any printing method such as screen printing, flexographic printing, lithography or nozzle printing, but more preferably LITI (photo-induced thermal imaging, thermal transfer) or ink jet printing to create one or more layers. For this purpose, soluble compounds are required, which are obtained, for example, by suitable substitution.

In addition, hybrid methods are possible in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.

Those skilled in the art are generally aware of these methods and can apply them to organic electroluminescent devices comprising the compounds of the present invention without inventive step.

The electronic devices of the present invention, in particular organic electroluminescent devices, stand out over the prior art by one or more of the following surprising advantages:

1. Compounds, oligomers, polymers or dendrimers described above and below or preferred embodiments comprising the compounds, oligomers, polymers or dendrimers used according to the invention, in particular as emitters, preferably as fluorescent emitters, as electron-conducting materials and/or Or hole transport materials or electronic devices as matrix materials, especially organic electroluminescent devices, have very good lifetimes.

2. Compounds, oligomers, polymers or dendrimers described above and below or preferred embodiments comprising the compounds, oligomers, polymers or dendrimers used according to the invention, in particular as emitters, preferably as fluorescent emitters, as electron transport materials, Hole transport materials and/or electronic devices as host materials, especially organic electroluminescent devices, have excellent efficiencies. More particularly, the efficiency is much higher compared to similar compounds that do not contain the structures of the present invention. In this context, the compounds, oligomers, polymers or dendrimers of the invention or the preferred embodiments described above and below yield low operating voltages when used in electronic devices. In this context, these compounds in particular give low roll-off, ie a slight decrease in the power efficiency of the device at high luminous densities.

3. Comprising compounds, oligomers, polymers and dendrimers or preferred embodiments described above and below, as emitters, preferably as fluorescent emitters, as electron transport materials, hole transport materials and/or Electronic devices as host materials, especially organic electroluminescent devices, have very narrow emission bands with low FullWidth Half Maximum (FWHM) values and result in particularly pure color luminescence recognizable by low CIE y-values .

4. The compounds, oligomers, polymers or dendrimers or preferred embodiments described above and below for use according to the invention exhibit very high thermal and photochemical stability and result in compounds with very long lifespan.

5. Using compounds, oligomers, polymers or dendrimers or preferred embodiments described above and below, the formation of optical loss channels in electronic devices, especially organic electroluminescent devices, can be avoided. Thus, these devices are characterized by high PL efficiency and thus high EL efficiency of the emitter, and excellent energy transfer from the host to the dopant.

6. The compounds, oligomers, polymers or dendrimers or preferred embodiments described above and below have excellent glass film formation.

7. The compounds, oligomers, polymers or dendrimers or preferred embodiments described above and below form very good films from solution.

These above-mentioned advantages are generally not accompanied by further degradation of electronic properties.

In the further layers of the organic electroluminescent device of the present invention, any material commonly used according to the prior art can be used. Therefore, a person skilled in the art can, without inventive step, combine any material known for use in organic electroluminescent devices with the compounds of the present invention which can be used as active compounds in organic electronic devices, preferably comprising formula (I) , (IIa) to (IIc) and/or (IIb-1) to (IIb-4) or compounds according to preferred embodiments are used in combination.

The compounds of the present invention generally have very good properties when used in organic electroluminescent devices. Especially in the case of the compounds according to the invention for use in organic electroluminescent devices, the lifetime is significantly better compared to similar compounds according to the prior art. At the same time, the other properties of the organic electroluminescent device, especially efficiency and voltage, are likewise better or at least comparable.

It should be noted that variations of the embodiments described in the present invention are encompassed by the scope of the present invention. Unless expressly excluded, any feature disclosed in the present invention may be replaced by an alternative feature serving the same or equivalent or similar purpose. Accordingly, unless stated otherwise, any features disclosed in this specification should be considered as examples of a generic series or as equivalent or similar features.

All features of the invention may be combined with each other in any way, unless specific features and/or steps are mutually exclusive. This is especially true of the preferred features of the invention. Likewise, features that are not necessarily combined may be used individually (but not in combination).

Furthermore, it should be pointed out that many of the features, especially those of the preferred embodiments of the invention, should be considered inventive in their own right and should not be regarded as merely some embodiments of the invention. For these features, independent protection may be sought in addition to or in lieu of any presently claimed invention.

The technical teachings of the present disclosure may be distilled and combined with other embodiments.

The present invention is illustrated in detail by the following examples without intending to limit the present invention thereby.

A person skilled in the art will be able to use the details given without inventive step to manufacture further electronic devices of the invention and thus implement the invention within the full scope of what is claimed.

Example

Unless otherwise stated, the following syntheses were performed in anhydrous solvents under a protective gas atmosphere. Additionally, the metal complexes are handled in the dark or under yellow light. Solvents and reagents can be purchased from eg Sigma-ALDRICH or ABCR. The corresponding numbers in square brackets or reference numbers for individual compounds refer to the CAS numbers of the compounds known from the literature. Where compounds can have multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown in a representative fashion.

Synthesis of Compounds of the Invention

Example B1:

Similar to the procedure of F. Zhao et al, Tetrahedron Letter, 2017, 58(32), 3132. To 2.56 g [10 mmol] of 4-phenylbenzo[h]quinazoline [4786-81-6] and 2.02 g [11 mmol] of saccharin [81-07-2] in 80 ml of ethyl acetate (EA) To the solution was added 8.60 g (20 mmol) of [bis(trifluoroacetoxy)iodo]benzene [2712-78-9], and the mixture was stirred at 60 °C for 12 h. After cooling, 100 ml of water are carefully added, the mixture is stirred for 10 minutes, and the organic phase is separated off, washed with saturated sodium chloride solution and concentrated to dryness. The soluble product was first purified by flash chromatography (silica gel, n-heptane/EA (ethyl acetate), Torrent automated column system from A. Semrau). Further purification was achieved by repeated chromatography or by thermal extraction from DCM (dichloromethane)/acetonitrile (1:2 to 1:5, vv) and crystallization by fractional sublimation under high vacuum. Yield: 2.80 g (6.3 mol) 63%; Purity: about 99.9% according to HPLC.

The following compounds can be prepared analogously:

Example B50:

Similar to the procedure of Yu-Qing Ouyang et al., Synth. Commun., 2017, 47(8), 771. The aryldiazonium tetrafluoroborates used were prepared from the corresponding arylamines (here 2-amino-9,9'-spirobifluorene) as described therein and were further converted immediately.

1.83 g [10 mmol] of saccharin [81-07-2], 1.38 g [10 mmol] of potassium carbonate, 198 mg [2 mmol] of cuprous(I) chloride, 30 g of A solution of 4.77g [11mmol] of 2-spiro-9,9'-bisfluorenyl diazonium tetrafluoroborate in 20ml of DMSO was added dropwise to the mixture of glass beads (3mm in diameter) and 50ml of DMSO (Note: gas evolution , foaming!), and then stirred for another 12h. The salts were filtered off as a DMSO slurry using a bed of diatomaceous earth, rinsed with a small amount of DMSO, and the filtrate was poured into 500 ml of water. The mixture was extracted three times with 100 ml each of dichloromethane (DCM) and the combined organic phases were washed three times with 200 ml each of water and once with 200 ml of saturated sodium chloride solution and concentrated to dryness. The soluble product was first purified by flash chromatography (silica gel, n-heptane/EA (ethyl acetate), Torrent automated column system from A. Semrau). Further purification was achieved by repeated chromatography or by thermal extraction from DCM/acetonitrile (1:2 to 1:5, vv) and crystallization by fractional sublimation under high vacuum. Yield: 2.85 g (5.7 nmol), 57%; Purity: about 99.9% according to HPLC.

The following compounds can be prepared analogously:

Example B100:

2.08 g [10 mmol] of 9,10-diaminophenanthrene [53348-04-2], 2.02 g [10 mmol] of 2-cyanobenzenesulfonyl chloride [69360-26-5], 2.86 ml [12 mmol] of trisodium A mixture of n-butylamine and 20 ml of o-dichlorobenzene was stirred at 150°C for 30 minutes. After cooling, 50 ml of ethanol were carefully added starting from about 100°C, and while the mixture was still warm, the product was filtered off and washed three times with 15 ml each of ethanol and dried under reduced pressure. The soluble product was first purified by flash chromatography (silica gel, n-heptane/EA (ethyl acetate), Torrent automated column system from A. Semrau). Further purification was achieved by thermal extraction from DCM (dichloromethane)/acetonitrile (1:2, vv) and repeated crystallization by fractional sublimation under high vacuum. Yield: 1.93 g (5.4 mmol), 54%; Purity: about 99.9% according to HPLC.

The following compounds can be prepared analogously:

Example: Fabrication of OLEDs

1) Vacuum processing devices:

The OLEDs of the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is adapted to the situation described here (variation of layer thickness, materials used).

In the following examples, results for various OLEDs are presented. Clean glass plates (washed in Miele laboratory glass washer, Merck Extran detergent) coated with structured ITO (indium tin oxide) with a thickness of 50 nm were pretreated with UV ozone for 25 min (PR-100 UV ozone generation from UVP PEDOT:PSS (poly(3,4-ethylidenedioxythiophene):poly(styrene sulfonate), available as CLEVIOS ^™ P VP AI 4083) within 30 minutes for improved processing from Heraeus Precious Metals GmbH Deutschland, spin-coated from aqueous solution) and baked at 180°C for 10 minutes. These coated glass sheets form the substrate to which the OLEDs are applied.

The OLED basically had the following layer structure: substrate/hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (available from Novaled), 20 nm/hole transport layer 1 (HTL1) ( Consists of 170nm for blue devices, 215nm for green/yellow devices, and 110nm for red devices) / Hole Transport Layer 2 (HTL2) / Emitting Layer (EML) / Hole Blocking Layer (HBL) / Electrons Transport layer (ETL)/optional electron injection layer (EIL from ETM2) and finally cathode. The cathode was formed from an aluminum layer with a thickness of 100 nm.

First, vacuum processed OLEDs are described. For this purpose, all materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the light-emitting layer always consists of at least one host material (host material) and light-emitting dopants (emitters) which are added to the one or more host materials by co-evaporation in specific volume proportions. The details given for example in the form of M1:M2:Ir(L1) (55%:35%:10%) here means that the material M1 is present in the layer in a volume ratio of 55% and M2 is present in a volume ratio of 35% in the layer, and Ir(L1) is present in the layer in a volume ratio of 10%. Similarly, the electron transport layer can also consist of a mixture of the two materials. The exact structure of the OLED can be found in Table 1. The materials used to fabricate the OLEDs are shown in Table 6.

The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectrum was measured, and the current efficiency (measured in cd/A), the power efficiency ( measured in lm/W) and external quantum efficiency (EQE, measured in percent), and lifetime. Electroluminescence spectra were measured at a luminous density of 1000 cd/m ² and these were used to calculate the CIE 1931 x and y color coordinates.

Use of the compounds of the invention as emitter materials in phosphorescent OLEDs

Among other uses, the compounds of the present invention can be used as electron-conducting host material eTMM in the emissive layer EML of phosphorescent OLEDs, and as electron-transporting material in HBL and ETL. The results of the OLEDs are collated in Table 2.

Table 1: Structure of OLED

Table 2: Results of vacuum processed OLEDs

Use of compounds of the invention as emitter materials in fluorescent OLEDs

One use of the compounds of the invention is as emitters (dopants) in fluorescent OLEDs. The results of the OLEDs are collated in Table 3.

Table 3: Structure of OLED

Table 4: Results of vacuum processed OLEDs

2) Solution-processed devices:

The compounds of the present invention can also be processed from solution, and in them OLEDs are produced which are much simpler in terms of processing technology than vacuum processed OLEDs, but still have good properties. The manufacture of these components is based on the manufacture of polymer light-emitting diodes (PLEDs), which have been described several times in the literature (eg in WO 2004/037887). The structure contains substrate/ITO/hole injection layer (60nm)/intermediate layer (20nm)/light emitting layer (60nm)/hole blocking layer (10nm)/electron transport layer (40nm)/cathode. For this purpose, a substrate (soda lime glass) from Technoprint was used, to which an ITO structure (indium tin oxide, transparent conductive anode) was applied. The substrates were cleaned with deionized water and detergent (Deconex 15PF) in a clean room and then activated by UV/ozone plasma treatment. Then, a 20 nm hole injection layer (PEDOT:PSS from Clevios ^™ ) was also applied by spin coating in a clean room. The required spin rate depends on the degree of dilution and the specific spin coater geometry. To remove residual water from the layers, the substrates were baked on a hot plate at 200°C for 30 minutes. The intermediate layer used is for hole transport, in this case HL-X from Merck. Optionally, the intermediate layer can also be replaced by one or more layers that only have to satisfy the condition that they will not be re-leached by subsequent processing steps of EML deposition from solution. To produce the light-emitting layer, the triplet emitter of the invention is dissolved together with the matrix material in toluene or chlorobenzene. Typical solids contents of these solutions range from 16 to 25 g/l when the typical 60 nm layer thickness for devices is achieved by means of spin coating as here. The solution-processed devices contained light-emitting layers Ma:Mb:Ir (w%:x%:z%) or Ma:Mb:Mc:Ir (w%:x%:y%:z%); see Table 3. The light-emitting layer was spin-coated in an inert gas atmosphere (argon in this example) and baked at 160°C for 10 minutes. A hole blocking layer (10nm ETM1) and an electron transport layer (40nm ETM1(50%)/ETM2(50%)) were vapor deposited on top of the latter (from a vapor deposition system from Lesker et al., with a typical vapor deposition pressure of 5× 10 ^-6 mbar). Finally, an aluminium cathode (100 nm) (high purity metal from Aldrich) was applied by vapour deposition. In order to protect the device from air and air humidity, the device was finally encapsulated and then characterized. The OLED examples cited have not been optimized. Table 5 summarizes the data obtained.

Table 5: Results for materials processed from solution

Table 6: Structural formulas of the materials used

The materials of the present invention, when used in the light-emitting layer EML, the hole blocking layer HBL and the electron transport layer ETL, lead to improved EQE (external quantum efficiency) together with reduced voltage and thus overall power efficiency.

Claims (22)

1. The use of a compound comprising at least one structure of formula (I), preferably a compound of formula (I), in organic electronic devices,

in: W is C=O, C=N-Ar or SO2 _; Ar is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups; the Ar groups here may be combined with The second Ar group, R group, X group or another group forms a ring system; X is N or CR, provided that no more than two X groups in a ring are N; R is the same or different in each case and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar') ₂ , N(R1 _{)2 ,} C( ⁼ O)N (Ar') ₂ , C(=O)N(R ¹ ) ₂ , C(Ar') ₃ , C(R ¹ ) ₃ , Si(Ar') ₃ , Si(R ¹ ) ₃ , B(Ar' ) ₂ , B(R ¹ ) ₂ , C(=O)Ar', C(=O)R ¹ , P(=O)(Ar') ₂ , P(=O)(R ¹ ) ₂ , P( Ar') ₂ , P(R ¹ ) ₂ , S(=O)Ar', S(=O)R ¹ , S(=O) ₂ Ar', S(=O) ₂ R ¹ , OSO ₂ Ar' , OSO ₂ R ¹ , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or A branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl The groups may in each case be substituted by one or more R ¹ groups, wherein one or more non-adjacent CH ₂ groups may be replaced by R ¹ C=CR ¹ , C≡C, Si(R ¹ ) _2. C=O, C=S, C=Se, C=NR ¹ , -C(=O)O-, -C(=O)NR ¹ -, NR ¹ , P(=O)(R ¹ ) , -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring having ₅ to 60 aromatic ring atoms and in each case may be substituted by ^one or more R1 groups system, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and may be substituted with ^one or more R groups; at the same time, two R groups may also be taken together to form a ring system or form a ring system with another group; Ar' is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by ^one or more R groups; at the same time, bonded to the same carbon The two Ar' groups of atoms, silicon atoms, nitrogen atoms, phosphorus atoms or boron atoms can also be via a bridging group via a single bond or selected from the group consisting of B(R ¹ ), C(R ¹ ) ₂ , Si(R ¹ . ) ₂ , C=O, C=NR ¹ , C=C(R ¹ ) ₂ , O, S, S=O, SO ₂ , N(R ¹ ), P(R ¹ ), and P(=O)R The bridging bases of ¹ are connected together; R ¹ is the same or different in each case and is H, D, F, Cl, Br, I, CN, NO ₂ , N(Ar”) ₂ , N(R ² ) ₂ , C(=O)Ar” , C(=O)R ² , P(=O)(Ar”) ₂ , P(Ar”) ₂ , B(Ar”) ₂ , B(R ² ) ₂ , C(Ar”) ₃ , C( R ² ) ₃ , Si(Ar”) ₃ , Si(R ² ) ₃ , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or 3 to 40 A branched or cyclic alkyl, alkoxy or thioalkoxy group of carbon atoms, or an alkenyl group of 2 to 40 carbon atoms, each of which may be replaced by a or more R ² groups, wherein one or more non-adjacent CH ₂ groups may be substituted with -R ² C=CR ² -, -C≡C-, Si(R ² ) ₂ , C=O, C=S, C=Se, C=NR ² , -C(=O)O-, -C(=O)NR ² -, NR ² , P(=O)(R ² ), -O-, - S-, SO or SO2 replacement and one or more of the _hydrogen atoms can be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic having ₅ to 60 aromatic ring atoms Aromatic ring systems, each of which may be substituted with one or more R groups, or which have ⁵ to 60 aromatic ring atoms and may be substituted with one or more ^R groups group-substituted aryloxy or heteroaryloxy groups, or aralkyl or heteroaralkyl groups having ⁵ to 60 aromatic ring atoms and which may be substituted with one or more R groups, or these A combination of systems; at the same time, two or more preferably adjacent R ¹ groups may together form a ring system; at the same time, one or more R ¹ groups may form a ring system with another moiety of the compound; Ar" is the same or different in each case and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which may be substituted by one or more R groups ^; at the same time, bonded to the same carbon The two Ar" groups of atoms, silicon atoms, nitrogen atoms, phosphorus atoms or boron atoms can also be via a bridging group through a single bond or selected from B(R ² ), C(R ² ) ₂ , Si(R ² ) ) ₂ , C=O, C=NR ² , C=C(R ² ) ₂ , O, S, S=O, SO ₂ , N(R ² ), P(R ² ), and P(=O)R The bridging bases of ² are connected together; R ² is in each case the same or different and is selected from H, D, F, CN, aliphatic hydrocarbyl radicals having 1 to 20 carbon atoms, or aromatic or heterocyclic radicals having 5 to 30 aromatic ring atoms Aromatic ring systems in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and in which the aromatic or heteroaromatic ring system may be replaced by a or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more preferably adjacent substituents R ² may together form a ring system. 2. The use according to claim 1, wherein the compound comprising the structure of formula (I), preferably the compound of formula (I), is used in organic electronic devices as fluorescent emitters, phosphorescent emitters, display TADF (thermally activated Delayed fluorescence) emitter, host material, exciton blocking material, electron injection material, electron transport material, electron blocking material, hole injection material, hole conducting material, hole blocking material, n-type dopant, p-type Dopants, wide bandgap materials and/or charge generating materials, preferably as host materials, electron transport materials, hole blocking materials and/or emitters exhibiting TADF (thermally activated delayed fluorescence), more preferably as phosphorescent emitters and especially preferably, if W is C=O or SO ₂ , for use as a host material for blue phosphorescent emitters. 3. Use according to claim 1 or 2, characterized in that the compound comprises at least one structure of formula (IIa), (IIb) and (IIc), and is preferably selected from the group consisting of formula (IIa), (IIb) and compounds of (IIc),

wherein the Ar and R groups have the definitions given in claim 1 and the designation m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2. 4. The use according to one or more of the preceding claims, characterized in that two Ar groups, preferably two Ar groups bound to a nitrogen atom in formula (IIb), together form a An aromatic or heteroaromatic ring system of 60 aromatic ring atoms and which may be substituted by one or more R ¹ groups, wherein the R ¹ groups have the definition detailed in claim 1 . 5. Use according to one or more of the preceding claims, characterized in that at least one of the Ar and/or R groups is selected from the following groups: phenyl, fluorene, indenofluorene, Spirobifluorene, Carbazole, Indenocarbazole, Indolocarbazole, Spirocarbazole, Pyrimidine, Triazine, Quinazoline, Quinoxaline, Pyridine, Quinoline, Isoquinoline, Lactam, Triarylamine , dibenzofuran, dibenzothiophene, imidazole, benzimidazole, benzo

azole, benzothiazole, 5-arylphenanthridine-6-one, 9,10-dehydrophenanthrene, fluoranthene, naphthalene, phenanthrene, anthracene, benzanthracene, indeno[1,2,3-jk]fluorene, Pyrene, perylene, chicory, borazine, boroxane, borazine, borazane, borazine, ketone, phosphine oxide, arylsilane, siloxane, and combinations thereof. 6. Use according to at least one of the preceding claims, characterized in that the compound contains a hole-transporting group, wherein preferably one of the Ar and/or R groups contains a hole-transporting group and preferably is a hole transport group. 7. Use according to claim 6, characterized in that the hole transport group comprises a group selected from formulae (H-1) to (H-3) and preferably is selected from formula (H-1) to (H-3) groups,

where the dotted keys mark the connection locations and the symbols are defined as follows: Ar ² , Ar ³ , Ar ⁴ are in each case independently an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, said aromatic ring system or Each of the heteroaromatic ring systems may be substituted with ^one or more R groups; p is 0 or 1; Z is a bond or C(R ¹ ) ₂ , Si(R ¹ ) ₂ , C=O, NR ¹ , N-Ar ¹ , BR ¹ , PR ¹ , PO(R ¹ ), SO, SO ₂ , Se, O or S, preferably a bond or C(R ¹ ) ₂ , N-Ar ¹ , O or S; wherein Ar ¹ is an aromatic ring system having 6 to 40 carbon atoms or a heteroaromatic ring system having 3 to 40 carbon atoms, which may be replaced by one or more R ¹ group is substituted, and said R ¹ group has the definitions detailed above, especially in claim 1 . 8. Use according to claim 6 or 7, characterized in that the hole transport group comprises a group selected from formulae (H-4) to (H-26) and preferably is selected from formula (H- 4) to the group of (H-26),

Wherein Y ¹ represents O, S, C(R ¹ ) ₂ or NAr ¹ , the dotted line key marks the connection 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, Ar ¹ , Ar ² and R ¹ have the definitions given in claim 9 . 9. The use according to at least one of the preceding claims, characterized in that the compound comprises a group containing an electron-transporting group, wherein preferably one of the Ar and/or R groups comprises a group containing an electron-transporting group group and preferably represents a group containing an electron-transporting group. 10. Use according to claim 9, characterized in that the electron transport group is selected from the group consisting of formula (Q-11), (Q-12), (Q-13), (Q-14) and/or ( Q-15) structure,

wherein the symbol R1 has the definition given above in claim ¹ , X ^' is N or CR1 and the dashed bond marks the position of attachment, wherein X' preferably represents a nitrogen atom. 11. Use according to claim 9 or 10, characterized in that the electron transport group is selected from the group consisting of formula (Q-26), (Q-27), (Q-28), (Q-29) and/ or (Q-30) structure,

wherein the symbols Ar ¹ and R ¹ have the definitions given above in claim 1 or 9, X' is N or CR ¹ and the dashed bond marks the position of attachment, wherein preferably exactly one X' represents a nitrogen atom. 12. Use according to at least one of the preceding claims, characterized in that at least one of the Ar and/or R groups comprises at least one fused aromatic or heteroaromatic having two, preferably three An aromatic or heteroaromatic ring system of an aromatic ring. 13. Use according to claim 12, characterized in that the aromatic or heteroaromatic ring system having two, preferably three fused aromatic or heteroaromatic rings is selected from the group consisting of formula (Ar- 1) to (Ar-17) groups,

wherein X' is N or CR ¹ , preferably CR ¹ , and L ¹ represents a bond or an aromatic or heterocyclic atom having 5 to 40, preferably 5 to 30, aromatic ring atoms which may be substituted by one or more R ¹ groups Aromatic ring system, R ¹ has the definition detailed in claim 1 and the dashed bond marks the position of attachment. 14. A composition comprising a combination comprising the following compounds: A) one or more compounds comprising at least one structure of formula (I), preferably one or more compounds of formula (I),

wherein the symbols X, W and Ar have the definitions given in claim 1; B) additional compounds selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, exciton blocking materials, electron injection materials, electron transport materials, electron blocking materials, Hole injecting materials, hole conducting materials, hole blocking materials, n-type dopants, p-type dopants, wide bandgap materials and/or charge generating materials. 15. A compound comprising at least one structure of formula (III), preferably a compound of formula (III),

wherein the symbols X and W have the definitions given in claim 1, and HetAr is a heteroaromatic ring system having 5 to 60 aromatic ring atoms and may be substituted by ^one or more R groups; the HetAr group The group here may form a ring system together with an Ar group, an R group, an X group or another group; wherein HetAr is preferably selected from the formulae (H-1) to (H-1) as defined in claims 7 and 8 26) or a group selected from the group consisting of formulae (Q-11) to (Q-30) as defined in claims 10 and 11. 16. A compound comprising at least one structure of formula (V), preferably a compound of formula (V),

wherein the symbols X and W have the definitions given in claim 1, and KonAr represents having two, preferably three, fused aromatic or heteroaromatic rings and having 10 to 60 aromatic ring atoms, preferably 12 to 40 An aromatic or heteroaromatic ring system of aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by ^one or more R groups, wherein the KonAr group may be combined with an Ar group, R The group, the X group or another group forms a ring system, wherein KonAr is preferably a group selected from the group consisting of formulae (Ar-1) to (Ar-17) as defined in claim 13, more preferably selected from the group consisting of claim 13 Groups of formulae (Ar-3) to (Ar-17) as defined in 13. 17. A compound comprising at least one structure of formula (VII), preferably a compound of formula (VIII),

wherein the symbols X, Ar and W have the definitions given above, especially in claim 1, wherein the structure/compound has at least one aromatic or heteroaromatic ring system, the aromatic or heteroaromatic ring The system has 5 to 60 carbon atoms and has a non-aromatic or non-heteroaromatic ring system fused thereto. 18. A compound comprising exactly two, exactly three or exactly four formulae (I) as defined in claim 1 and/or formulae (IIa) to (IIc) as defined in claim 3 Structure. 19. A compound having at least one of formulae (IXa) to (IXc),

wherein the symbols Ar and W have the definitions given in claim ¹ , X is N, CR, and if the L group is combined with X, then X is C, provided that no more than two X groups in a ring are N; and L ¹ represents a bond or an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, aromatic ring atoms, and which may be surrounded by one or more R ¹ group substitution. 20. An oligomer, polymer or dendrimer containing at least one use as defined in one or more of claims 1 to 14 The compound in , or a compound according to any one of claims 15 to 17, wherein, instead of a hydrogen atom or substituent, there is one or more bonds to the corresponding structural isomer in the mixture, with The polymer, oligomer or dendrimer is formed. 21. A formulation comprising one or more compounds according to one or more of claims 15 to 19, oligomers, polymers or dendrimers according to claim 20 A molecule or composition according to claim 14 and at least one solvent. 22. An electronic device comprising at least one compound according to the use as defined in one or more of claims 1 to 14, according to one or more of claims 15 to 19 A compound according to claim 22, an oligomer, polymer or dendrimer according to claim 22, or a composition according to claim 14, wherein the electronic device is preferably selected from organic electroluminescent devices, Organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field quenching devices, light emitting electrochemical cells and organic laser diodes.