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Definitions

• the present invention relates to materials for use in electronic devices, especially as host material for phosphorescent emitters in organic electroluminescent devices, and to electronic devices, especially organic electroluminescent devices, comprising these materials.
• Emitting materials used in organic electroluminescent devices are increasingly organometallic complexes which exhibit phosphorescence rather than fluorescence, especially iridium or platinum complexes.
• organometallic complexes which exhibit phosphorescence rather than fluorescence, especially iridium or platinum complexes.
• phosphorescent organometallic compounds as phosphorescent emitters.
• phosphorescent OLEDs are not just determined by the triplet emitters used. Also of particular significance here are especially the other materials used, such as matrix materials, hole blocker materials, electron transport materials, hole transport materials and electron or exciton blocker materials. Improvements to these materials can thus also lead to distinct improvements in the OLED properties. For fluorescent OLEDs too, there is still a need for improvement in these materials.
• lactams for example according to WO 2011/137951 or WO 2013/064206, are one kind of matrix materials used for phosphorescent emitters.
• matrix materials used for phosphorescent emitters.
• the present invention provides a compound of the following formula (1)
• Adjacent X groups in the context of the present invention are X groups bonded directly to one another.
• Adjacent substituents in the context of the present invention are substituents bonded to atoms that are in turn bonded directly to one another, or bonded to the same atom.
• An aryl group in the context of this invention contains 6 to 60 carbon atoms; a heteroaryl group in the context of this invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum total of carbon atoms and heteroatoms is at least 5.
• the heteroatoms are preferably selected from N, O and/or S.
• An aryl group or heteroaryl group is understood here to mean either a simple aromatic cycle, i.e.
• Aromatic systems joined to one another by a single bond for example biphenyl, by contrast, are not referred to as an aryl or heteroaryl group but as an aromatic ring system.
• An aromatic ring system in the context of this invention contains 6 to 80 carbon atoms in the ring system.
• a heteroaromatic ring system in the context of this invention contains 2 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum total of carbon atoms and heteroatoms is at least 5.
• the heteroatoms are preferably selected from N, O and/or S.
• An aromatic or heteroaromatic ring system in the context of this invention shall be understood to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which it is also possible for two or more aryl or heteroaryl groups to be joined by a nonaromatic unit, for example a carbon, nitrogen or oxygen atom.
• systems such as fluorene, 9,9′-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. shall also be regarded as aromatic ring systems in the context of this invention, and likewise systems in which two or more aryl groups are joined, for example, by a short alkyl group.
• an aliphatic hydrocarbyl radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 40 carbon atoms and in which individual hydrogen atoms or CH 2 groups may also be replaced by the abovementioned groups are preferably understood to mean the methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-
• An alkoxy group having 1 to 40 carbon atoms is preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
• a thioalkyl group having 1 to 40 carbon atoms is understood to mean especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthi
• alkyl, alkoxy or thioalkyl groups according to the present invention may be straight-chain, branched or cyclic, where one or more nonadjacent CH 2 groups may be replaced by the abovementioned groups; in addition, it is also possible for one or more hydrogen atoms to be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, further preferably F or CN, especially preferably CN.
• An aromatic or heteroaromatic ring system which has 5-80 aromatic ring atoms and may also be substituted in each case by the abovementioned R 1 radicals or a hydrocarbyl radical and which may be joined to the aromatic or heteroaromatic system via any desired positions is especially understood to mean groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, tru
• Each cycle having X groups in the structure of the formula (1) is a five- or six-membered ring, where ring formation between the R radicals can also give rise to fused structures. Even when adjacent X groups are a group of the formula (2), (3) or (4), larger fused structures arise. This means that not more than one X—X moiety per cycle is O, S or NR. It is preferable here when the group of the formula (2) is bonded within a six-membered ring. It is further preferable when each cycle contains not more than one group of the formula (2), (3) or (4). Thus, when a cycle in formula (1) contains a group of the formula (2), it is preferable when the other X groups in this cycle are the same or different and are each CR or N, especially CR.
• not more than one X group per cycle is N. More preferably, no X group is N, meaning that all the X groups that are not a group of the formula (2), (3) or (4) or O, S or NR are more preferably CR.
• At least one of the A 1 and A 2 groups is a single bond.
• a group of the formula (2) is bonded to the same half of the spiro compound on which this A 1 or A 2 group which is a single bond is also present.
• a 1 and A 2 are a single bond.
• two adjacent X groups are a group of the formula (2).
• the compound of the formula (1) contains one or two groups of the formula (2), more preferably exactly one group of the formula (2).
• ⁇ represents the linkage to the nitrogen atom in the group of the formula (2)
• # represents the linkage to the E group in the group of the formula (2)
• the further symbols used are as defined above.
• the two X groups in the cycle to which the group of the formula (2) is bonded are CR or N, especially CR.
• these groups may either be bonded to the same half of the spiro compound, as indicated schematically in the following formula (11), or they may be bonded to the two different halves of the spiro compound, as indicated schematically in the following formula (12):
• a preferred embodiment of compounds having two groups of the formula (2) is the compound of the following formula (12a):
• Preferred compounds of the formulae (5a) to (35a) are the compounds of the formulae (5b) to (10b):
• Z is the same or different and is C ⁇ O or C ⁇ S, more preferably C ⁇ O.
• E is a single bond.
• CR 2 , C ⁇ O or NR more preferably a single bond, CR 2 or C ⁇ O and most preferably a single bond.
• the Ar 1 group is a group of the following formula (13), (14), (15), (16) and (17)
• the Ar 2 group is a group of one of the following formulae (20), (21) and (22)
• At least one of the Ar 1 and Ar 2 groups is a 6-membered aryl or a 6-membered heteroaryl group. More preferably, both Ar 1 and Ar 2 groups are a 6-membered aryl or a 6-membered heteroaryl group. More preferably, thus, Ar 1 is a group of the formula (13) and, at the same time, Ar 2 is a group of the formula (20).
• Preferred embodiments of the group of the formula (2) are therefore the compounds of the following formulae (23) to (29):
• two adjacent W groups can be a group of the abovementioned formula (18) or (19).
• not more than one W symbol in total per cycle is N, and the remaining W symbols that are not a group of the formula (18) or (19) are CR.
• all W symbols that are not a group of the formula (18) or (19) are CR.
• Particularly preferred groups of the formula (2) are therefore the groups of the following formulae (23a) to (29a):
• Very particularly preferred groups of the formula (2) are the groups of the formula (23) or (23a) or (23b)
• Z is preferably C ⁇ O.
• E is preferably a single bond.
• Z is C ⁇ O and, at the same time, E is a single bond.
• two adjacent W groups are a group of the formula (18) or (19), that not more than one G group is N. More preferably, all G groups are CR. It is additionally preferable, when two adjacent W groups are a group of the formula (19), that E in the group of the formula (19) is CR 2 , C ⁇ O or NR, especially CR 2 or NR.
• Suitable compounds are therefore the compounds listed in the following table:
• Preferred compounds are the compounds listed in the following table:
• Particularly preferred compounds are the compounds listed in the following table:
• R in the abovementioned formulae is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, CN, N(Ar 3 ) 2 , C( ⁇ O)Ar 3 , 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 or alkynyl group having 2 to 10 carbon atoms, each of which may be substituted by one or more R 1 radicals, where one or more nonadjacent CH 2 groups may be replaced by O and where one or more hydrogen atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals.
• R in the abovementioned formulae is the same or different at each instance and is selected from the group consisting of H, D, F, CN, N(Ar 3 ) 2 , a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms or a cyclic alkyl group having 5 or 6 carbon atoms, each of which may be substituted by one or more R 1 radicals, where one or more hydrogen atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals.
• R in the abovementioned formulae is the same or different at each instance and is selected from the group consisting of H and an aromatic or heteroaromatic ring system which has 6 to 24, preferably 6 to 18, aromatic ring atoms and may be substituted in each case by one or more R 1 radicals.
• electron-deficient heteroaromatic groups are five-membered heteroaromatic rings having at least two heteroatoms or six-membered heteroaromatic rings having at least one heteroatom, to each of which may be fused another one or more aromatic or heteroaromatic groups.
• the Z group is C ⁇ O and/or when at least one of the R radicals is a substituted or unsubstituted carbazole, indenocarbazole or indolocarbazole, each of which may be bonded via a carbon atom or a nitrogen atom.
• the compounds of the invention do not have any aryl or heteroaryl groups in which two or more six-membered aryl or heteroaryl groups are fused directly to one another. More preferably, in this case, the compound of the invention does not contain any aryl or heteroaryl groups having six-membered rings fused directly to one another at all.
• either all R radicals are H or exactly one or two R radical(s) is/are an aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, and the other R radicals are H.
• R radicals are an aromatic or heteroaromatic ring system
• preferred R radicals are the same or different at each instance and are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, ortho-terphenyl, meta-terphenyl, para-terphenyl or branched terphenyl, ortho-quaterphenyl, meta-quaterphenyl, para-quaterphenyl or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, anthracene, phenanthrene, triphenylene, pyrene, benzanthracene, pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, 1-, 2- or 3-carbazole, 1-, 2- or 3-dibenzofuran, 1-, 2- or 3-dibenzofuran
• Preferred aromatic or heteroaromatic ring systems R are selected from the groups of the following formulae R-1 to R-53:
• R-1 group no, one, two or three A symbols are N.
• Particular preference is given to phenyl of the formula R-1a, pyrimidine of the formula R-1b or triazine of the formula R-1c
• R 1 is as defined above and, in formula R-1a, is especially H or an aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted by one or more R 2 radicals, and, in formula R-1b and R-1c, is in each case especially an aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted by one or more R 2 radicals.
• not more than one A symbol per cycle is N. More preferably, the symbol A is the same or different at each instance and is CR 1 , especially CH.
• At least one Y 1 group is C(R 1 ) 2 or NR 1 .
• the substituent R 1 bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may also be substituted by one or more R 2 radicals.
• this substituent R 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 24 aromatic ring atoms, which does not have any fused aryl groups and which does not have any fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-membered ring groups are fused directly to one another, and which may also be substituted in each case by one or more R 2 radicals.
• Particular preference is given to phenyl, biphenyl, terphenyl and quaterphenyl.
• R 1 is preferably the same or different at each instance and is a linear alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms, preferably 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, which may also be substituted by one or more R 2 radicals.
• R 1 is a methyl group or a phenyl group. In this case, the R 1 radicals together may also form a ring system, which leads to a spiro system.
• R is a triarylamine group which may be substituted by one or more R 1 radicals.
• the latter is preferably selected from the structures of the following formula R-54:
• Ar 4 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 18 aromatic ring atoms in each case, preferably 6 to 12 aromatic ring atoms in each case, and may be substituted in each case by one or more R 1 radicals.
• the alkyl groups preferably have not more than five carbon atoms, more preferably not more than 4 carbon atoms, most preferably not more than 1 carbon atom.
• suitable compounds are also those substituted by alkyl groups, especially branched alkyl groups, having up to 10 carbon atoms or those substituted by oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups.
• the compounds of the formula (1) or the preferred embodiments can be prepared by synthesis steps known to those skilled in the art, as shown in schematic form in scheme 1.
• the synthesis proceeds from a halogen-functionalized, especially bromine-functionalized, spirobifluorene derivative.
• the starting materials are the corresponding functionalized spiro compounds having A 1 and A 2 groups.
• the latter is converted in a C—N coupling reaction, for example a Hartwig-Buchwald coupling, with an ortho-haloamino-substituted aromatic or heteroaromatic, for example an ortho-chloroaminobenzene derivative, followed by a palladium-catalyzed ring closure reaction to give the corresponding spirocarbazole derivative.
• the reaction can also be effected with an ortho-halobenzyl bromide or a corresponding heteroaromatic compound, followed by a palladium-catalyzed ring closure reaction and oxidation of the cyclic amine to the lactam.
• Substituted compounds are obtainable by using correspondingly substituted reactants.
• inventive compounds especially compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic ester, or by reactive polymerizable groups such as olefins or oxetanes, may find use as monomers for production of corresponding oligomers, dendrimers or polymers.
• the oligomerization or polymerization is preferably effected via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is additionally possible to crosslink the polymers via groups of this kind.
• the compounds of the invention and polymers may be used in the form of a crosslinked or uncrosslinked layer.
• the invention therefore further provides oligomers, polymers or dendrimers containing one or more of the above-detailed inventive compounds, wherein one or more bonds of the inventive compound to the polymer, oligomer or dendrimer are present. According to the linkage of the compound of the invention, it therefore forms a side chain of the oligomer or polymer or is incorporated in the main chain.
• the polymers, oligomers or dendrimers may be conjugated, partly conjugated or nonconjugated.
• the oligomers or polymers may be linear, branched or dendritic. For the repeat units of the compounds of the invention in oligomers, dendrimers and polymers, the same preferences apply as described above.
• the monomers of the invention are homopolymerized or copolymerized with further monomers. Preference is given to homopolymers or copolymers wherein the units of formula (1) or the above-recited preferred embodiments are present to an extent of 0.01 to 99.9 mol %, preferably 5 to 90 mol %, more preferably 20 to 80 mol %.
• Suitable and preferred comonomers which form the polymer base skeleton are chosen from fluorenes (for example according to EP 842208 or WO 2000/22026), spirobifluorenes (for example according to EP 707020, EP 894107 or WO 2006/061181), paraphenylenes (for example according to WO 92/18552), carbazoles (for example according to WO 2004/070772 or WO 2004/113468), thiophenes (for example according to EP 1028136), dihydrophenanthrenes (for example according to WO 2005/014689), cis- and trans-indenofluorenes (for example according to WO 2004/041901 or WO 2004/113412), ketones (for example according to WO 2005/040302), phenanthrenes (for example according to WO 2005/104264 or WO 2007/017066) or else a plurality of these units.
• fluorenes for example according to EP 842208 or
• the polymers, oligomers and dendrimers may contain still further units, for example hole transport units, especially those based on triarylamines, and/or electron transport units.
• the polymers may contain triplet emitters either in copolymerized form or mixed in as a blend. Specifically the combination of units of formula (1′) or the above-recited preferred embodiments with triplet emitters leads to particularly good results.
• the compounds of formula (1) or the above-recited preferred embodiments may also be further functionalized and thus be converted to extended structures. Examples here include the Suzuki reaction with arylboronic acids or the Hartwig-Buchwald reaction with primary or secondary amines.
• the compounds of formula (1) or the above-recited preferred embodiments may also be bonded directly to phosphorescent metal complexes or else to other metal complexes.
• formulations of the compounds of the invention are required. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferable to use mixtures of two or more solvents.
• Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, ( ⁇ )-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, do
• NMP NMP, p-cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or mixtures of these solvents.
• the present invention therefore further provides a formulation comprising a compound of the invention and at least one further compound.
• the further compound may, for example, be a solvent, especially one of the abovementioned solvents or a mixture of these solvents.
• the further compound may alternatively be at least one further organic or inorganic compound which is likewise used in the electronic device, for example an emitting compound and/or a further matrix material. Suitable emitting compounds and further matrix materials are listed at the back in connection with the organic electroluminescent device.
• This further compound may also be polymeric.
• the compounds of the invention are suitable for use in an electronic device, especially in an organic electroluminescent device.
• the present invention further provides for the use of the above-recited inventive compounds of formula (1) or of the preferred embodiments in an electronic device, especially in an organic electroluminescent device.
• An electronic device in the context of the present invention is a device comprising at least one layer comprising at least one organic compound.
• This component may also comprise inorganic materials or else layers formed entirely from inorganic materials.
• the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic plasmon emitting devices (D. M. Koller et al., Nature Photonics 2008, 1-4), but preferably organic electroluminescent devices (OLEDs), more preferably phosphorescent OLEDs.
• OLEDs organic electroluminescent devices
• O-ICs organic integrated circuits
• O-FETs organic field-effect transistors
• OF-TFTs organic thin-film transistors
• the organic electroluminescent device comprises cathode, anode and at least one emitting layer. Apart from these layers, it may comprise further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocker layers, electron transport layers, electron injection layers, exciton blocker layers, electron blocker layers and/or charge generation layers. It is likewise possible for interlayers having an exciton-blocking function, for example, to be introduced between two emitting layers. However, it should be pointed out that not necessarily every one of these layers need be present. In this case, it is possible for the organic electroluminescent device to contain an emitting layer, or for it to contain a plurality of emitting layers.
• emission layers preferably have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce are used in the emitting layers.
• various emitting compounds which may fluoresce or phosphoresce are used in the emitting layers.
• systems having three emitting layers, where the three layers show blue, green and orange or red emission for the basic construction see, for example, WO 2005/011013).
• the compound of the invention according to the above-detailed embodiments may be used in different layers, according to the exact structure.
• Preference is given to an organic electroluminescent device comprising a compound of formula (1) or the above-recited preferred embodiments as matrix material for fluorescent or phosphorescent emitters, especially for phosphorescent emitters, and/or in a hole blocker layer and/or in an electron transport layer and/or in an electron-blocking or exciton-blocking layer and/or in a hole transport layer, according to the exact substitution.
• the compound of formula (1) or the above-recited preferred embodiments is used as matrix material for a fluorescent or phosphorescent compound, especially for a phosphorescent compound, in an emitting layer.
• the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, where at least one emitting layer contains at least one compound of the invention as matrix material.
• the compound of formula (1) or the above-recited preferred embodiments is used as matrix material for an emitting compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
• Phosphorescence in the context of this invention is understood to mean luminescence from an excited state having higher spin multiplicity, i.e. a spin state >1, especially from an excited triplet state.
• all luminescent complexes with transition metals or lanthanides, especially all iridium, platinum and copper complexes shall be regarded as phosphorescent compounds.
• the mixture of the compound of formula (1) or the above-recited preferred embodiments and the emitting compound contains between 99% and 1% by volume, preferably between 98% and 10% by volume, more preferably between 97% and 60% by volume and especially between 95% and 80% by volume of the compound of formula (1) or the above-recited preferred embodiments, based on the overall mixture of emitter and matrix material.
• the mixture contains between 1% and 99% by volume, preferably between 2% and 90% by volume, more preferably between 3% and 40% by volume and especially between 5% and 20% by volume of the emitter, based on the overall mixture of emitter and matrix material.
• a further preferred embodiment of the present invention is the use of the compound of formula (1) or the above-recited preferred embodiments as matrix material for a phosphorescent emitter in combination with a further matrix material.
• matrix materials which can be used in combination with the inventive compounds are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, for example according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g.
• CBP N,N-biscarbazolylbiphenyl
• 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, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for example according to WO 2007/137725, silanes, for example according to WO 2005/111172, azaboroles or boronic esters, for example according to WO 2006/117052, triazine derivatives, for example according to WO 2007/063754, WO 2008/0567
• Suitable phosphorescent compounds are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal having this atomic number.
• Preferred phosphorescence 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 above-described emitters can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244, WO 2005/019373. US 2005/0258742, WO 2010/086089. WO 2011/157339, WO 2012/007086, WO 2012/163471, WO 2013/000531, WO 2013/020631. WO 2014/008982 and WO 2014/023377.
• the organic electroluminescent device of the invention does not contain any separate hole injection layer and/or hole transport layer and/or hole blocker layer and/or electron transport layer, meaning that the emitting layer directly adjoins the hole injection layer or the anode, and/or the emitting layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005/053051. It is additionally possible to use a metal complex identical or similar to the metal complex in the emitting layer as hole transport or hole injection material directly adjoining the emitting layer, as described, for example, in WO 2009/030981.
• the compound of formula (1) or the above-recited preferred embodiments is used as electron transport material in an electron transport or electron injection layer.
• the emitting layer may be fluorescent or phosphorescent.
• the compound when used as electron transport material, it may be preferable for it to be doped, for example with alkali metal complexes, for example LiQ (lithium hydroxyquinolinate).
• the compound of formula (1) or the above-recited preferred embodiments is used in a hole blocker layer.
• a hole blocker layer is understood to be a layer which directly adjoins an emitting layer on the cathode side.
• the compound of formula (1) or the above-recited preferred embodiments is used in a hole transport layer or in an electron blocker layer or exciton blocker layer.
• an organic electroluminescent device characterized in that one or more layers are coated by a sublimation process.
• the materials are applied by vapor deposition in vacuum sublimation systems at an initial pressure of less than 10 ⁇ 5 mbar, preferably less than 10 ⁇ 6 mbar. It is also possible that the initial pressure is even lower, for example less than 10 ⁇ 7 mbar.
• an organic electroluminescent device characterized in that one or more layers are coated by the OVPD (organic vapor phase deposition) method or with the aid of a carrier gas sublimation.
• the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
• OVJP organic vapor jet printing
• the materials are applied directly by a nozzle and thus structured (for example, M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
• an organic electroluminescent device characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, offset printing. LITI (light-induced thermal imaging, thermal transfer printing), inkjet printing or nozzle printing.
• LITI light-induced thermal imaging, thermal transfer printing
• inkjet printing or nozzle printing For this purpose, soluble compounds are needed, which are obtained, for example, through suitable substitution.
• 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 vapor deposition.
• the syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere.
• the reactants can be sourced from ALDRICH or ABCR.
• the numbers given in square brackets for the compounds known from the literature indicate the CAS numbers of these compounds.
• the mixture is cooled to room temperature and then a solution of 25.9 g (100 mmol) of 1-bromofluorenone [36804-63-4] in 500 mL of THF is added dropwise, and the reaction mixture is heated to 50° C. for 4 h and then stirred at room temperature for a further 12 h. 100 mL of water are added, the mixture is stirred briefly, the organic phase is removed and the solvent is removed under reduced pressure. The residue is suspended in 500 mL of glacial acetic acid heated to 40° C., 0.5 mL of conc. sulfuric acid is added to the suspension and the mixture is then stirred at 100° C. for 2 h.
• Br-biphenyl Br-fluorenone Product Br-spiro Yield 2052-07-5 2041-19-2 85% 13029-09-9 486-25-9 90% 1161009-88-6 2052-07-5 216312-73-1 85% 13029-09-9 4269-17-4 90% 1257321-41-7
• a 1 L four-neck flask is initially charged with 29 g (50 mmol) of 3a and 9.90 g (101 mmol) of potassium acetate in 500 mL of DMF, and argon is passed through for 30 minutes. Subsequently, 1.75 g (1.51 mmol) of Pd(PPh 3 ) 4 are added and the mixture is heated under reflux for 16 h until conversion is complete. The reaction mixture is cooled down to room temperature and hydrolyzed with 400 mL of water. The precipitated solid is filtered and washed with water. After drying under reduced pressure, the product is obtained as a gray solid. Yield: 4.7 g (50.0 mmol, corresponding to 99% of theory).
• PEDOT:PSS poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate
• the OLEDs basically have the following layer structure: substrate/hole transport layer (HTL)/optional interlayer (IL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode.
• the cathode is formed by an aluminum layer of thickness 100 nm.
• the exact structure of the OLEDs can be found in Table 1.
• the materials used for production of the OLEDs are shown in Table 3.
• the emission layer always consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation.
• the material from example 5e is present in the layer in a proportion by volume of 45%, the material IC2 in a proportion by volume of 45% and TEG1 in a proportion by volume of 10%.
• the electron transport layer may also consist of a mixture of two materials.
• the OLEDs are characterized in a standard manner.
• the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) are as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming Lambertian radiation characteristics.
• the electroluminescence spectra are determined at a luminance of 1000 cd/m 2 , and the CIE 1931 x and y color coordinates are calculated therefrom.
• the parameter U1000 in Table 2 refers to the voltage which is required for a luminance of 1000 cd/m 2 .
• CE1000 and PE1000 respectively refer to the current and power efficiencies which are achieved at 1000 cd/m 2 .
• EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd/m 2 .
• Examples C1-C2 are comparative examples according to the prior art; examples I1-I11 show data of OLEDs of the invention.
• the materials of the invention when used as matrix materials in phosphorescent OLEDs, give significant improvements in voltage and power efficiency over the prior art.
• the compound 5d of the invention in combination with the green-emitting dopant TEG1, it is possible to observe a significant improvement in voltage and power efficiency over the prior art (C1, C2) (example I1).

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