WO2021175706A1 - Utilisation de composés sulfone dans un dispositif électronique organique - Google Patents

Utilisation de composés sulfone dans un dispositif électronique organique Download PDF

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WO2021175706A1
WO2021175706A1 PCT/EP2021/054773 EP2021054773W WO2021175706A1 WO 2021175706 A1 WO2021175706 A1 WO 2021175706A1 EP 2021054773 W EP2021054773 W EP 2021054773W WO 2021175706 A1 WO2021175706 A1 WO 2021175706A1
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formula
group
aromatic
radicals
formulas
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PCT/EP2021/054773
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German (de)
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Philipp Stoessel
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Merck Patent Gmbh
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Priority to CN202180018027.1A priority Critical patent/CN115244728A/zh
Priority to EP21706988.9A priority patent/EP4115457A1/fr
Publication of WO2021175706A1 publication Critical patent/WO2021175706A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention describes the use of sulfone compounds in an organic electronic device.
  • the invention also relates to new sulfone compounds and processes for the preparation of the compounds according to the invention, as well as electronic devices containing these compounds.
  • organic electroluminescent devices in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461, WO 98/27136 and WO 2010/151006 A1.
  • Organometallic complexes that exhibit phosphorescence are often used as emitting materials.
  • the use of organometallic compounds as phosphorescence emitters can achieve up to four times the energy and power efficiency.
  • organic electroluminescent devices are known which comprise fluorescent emitters or emitters which exhibit TADF (thermally activated delayed fluorescence).
  • organic electroluminescent devices are not only determined by the emitters used.
  • the other materials used such as host / matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials, are of particular importance here. Improvements in these materials can lead to significant improvements in electroluminescent devices.
  • these materials exist, for example for use as emitters, preferably as fluorescent emitters, as matrix materials, hole transport materials or electron transport materials
  • emitters preferably as fluorescent emitters
  • matrix materials preferably as hole transport materials or electron transport materials
  • electron transport materials preferably as electron transport materials
  • the compounds should have a high degree of color purity.
  • Another object of the present invention is to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, as fluorescent emitters or emitters which show TADF (thermally activated delayed fluorescence), and which when used in this device lead to good device properties, as well as the provision of the corresponding electronic device.
  • fluorescent emitters or emitters which show TADF (thermally activated delayed fluorescence)
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which lead to good device properties when used in this device, and to provide the corresponding electronic device .
  • the properties of the matrix materials, the hole transport materials or the electron transport materials have a significant influence on the service life and the efficiency of the organic electroluminescent device.
  • Another object of the present invention can be seen in providing compounds which are suitable for use in a phosphorescent or fluorescent electroluminescent device, in particular as a matrix material.
  • a matrix material in particular as a matrix material.
  • the compounds should lead to devices which have excellent color purity.
  • the compounds should be as easy to process as possible, in particular they should exhibit good solubility and film formation.
  • the compounds should exhibit increased oxidation stability and an improved glass transition temperature.
  • a further object can be seen in providing electronic devices with excellent performance as inexpensively as possible and of constant quality. Furthermore, the electronic devices should be able to be used or adapted for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range. Surprisingly, it has been found that certain compounds described in more detail below achieve these objects and eliminate the disadvantage of the prior art.
  • the use of the compounds leads to very good properties of organic electronic devices, in particular of organic electroluminescent devices, in particular with regard to the service life, the efficiency and the operating voltage.
  • Electronic devices, in particular organic electroluminescent devices, which contain compounds of this type, and the corresponding preferred embodiments are therefore the subject matter of the present invention.
  • the present invention therefore provides a use of a compound comprising at least one structure of the formula (I), preferably a compound of the formula (I), Formula (I) where:
  • Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R, here the group Ar can be with at least one second group Ar, one radical R, one group X. or another group form a ring system;
  • X stands for N or CR, with the proviso that not more than two of the groups X in one cycle stand for N;
  • 0S0 2 Ar ', 0S0 2 R 1 a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy - Or thioalkoxy group with 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group can each be substituted by one or more radicals R 1 , one or more nonadjacent CH 2 groups being substituted by C.
  • Ar ' is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 1 , two radicals Ar' which are attached to the same carbon atom, Si Bond atom, N atom, P atom or B atom, also through a single bond or a bridge, selected from B (R 1 ), C (R 1 ) 2,
  • R 2 is on each occurrence, identically or differently, selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms in which one or more H atoms can be replaced by D, F, CI, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, two or more, preferably adjacent, substituents R 2 with one another form a ring system; in an organic electronic device.
  • the present compounds can be used as an active compound in electronic devices.
  • Active compounds are generally the organic or inorganic materials that are introduced between anode and cathode, for example in an organic electronic device, in particular in an organic electroluminescent device, for example charge injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials. Organic materials are preferred here.
  • a compound to be used according to the invention is preferably a purely organic compound.
  • a purely organic compound is a compound that is not in connection with a metal atom, i.e. neither forms a coordination compound with a metal atom, nor forms a covalent bond with a metal atom.
  • a purely organic compound preferably does not include a metal atom which is used in phosphorescence emitters. These metals, such as copper, molybdenum, etc., in particular rhenium, ruthenium, osmium, rhodium, iridium, palladium, will be described in detail later.
  • the compound that can be used as an active compound in an organic electronic device can preferably be selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials , Hole injection materials, n-dopants, p-dopants, wide-band gap materials, electron blocking materials and / or hole blocking materials.
  • fluorescent emitters phosphorescent emitters, emitters which show TADF (thermally activated delayed fluorescence)
  • host materials electron transport materials, exciton blocking materials, electron injection materials, hole transport materials , Hole injection materials, n-dopants, p-dopants, wide-band gap materials, electron blocking materials and / or hole blocking materials.
  • fluorescent emitters emitters that show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-dopants, p-dopants, wide-band gap materials, electron blocking materials and / or hole blocking materials preferred.
  • Adjacent carbon atoms in the context of the present invention are carbon atoms that are directly linked to one another.
  • neighborhboring radicals in the definition of the radicals means that these Radicals are bonded to the same carbon atom or to adjacent carbon atoms.
  • a condensed aryl group, a condensed aromatic ring system or a condensed heteroaromatic ring system for the purposes of the present invention is a group in which two or more aromatic groups are fused to one another via a common edge, so that, for example, two carbon atoms are part of the at least two aromatic or heteroaromatic rings belong, as for example in naphthalene.
  • fluorene for example, is not a condensed aryl group for the purposes of the present invention, since the two aromatic groups in fluorene do not have a common edge.
  • Corresponding definitions apply to Heteroaryl groups and for fused ring systems, which can also contain heteroatoms, but do not have to.
  • radicals R, R 1 and / or R 2 form a ring system with one another, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system can result.
  • an aryl group contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, particularly preferably 6 to 30 carbon atoms;
  • a heteroaryl group contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, particularly preferably 2 to 30 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 results.
  • the heteroatoms are preferably selected from N, O and / or S.
  • an aryl group or heteroaryl group either a simple aromatic cycle, i.e.
  • benzene or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl group, for example naphthalene, anthracene,
  • an aromatic ring system contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, particularly preferably 6 to 30 carbon atoms, in the ring system.
  • a heteroaromatic ring system for the purposes of this invention contains 1 to 60 C, preferably 1 to 40 C atoms, particularly preferably 1 to 30 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5 results.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system that does not necessarily contain only aryl or heteroaryl groups, but also contains several aryl or Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
  • B. a C, N or O atom or a carbonyl group can be interrupted.
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, Diaryl ethers, stilbene, etc.
  • aryl groups are understood to be aromatic ring systems in the context of this invention, and likewise systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group.
  • systems in which two or more aryl or heteroaryl groups are bonded directly to one another such as.
  • biphenyl, terphenyl, quaterphenyl or bipyridine can also be understood as an aromatic or heteroaromatic ring system.
  • a cyclic alkyl, alkoxy or thioalkoxy group in the context of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.
  • a C1 to C20 alkyl group in which individual H atoms or CH2 groups can also be substituted by the groups mentioned above, for example the radicals methyl, ethyl, n-propyl, i-propyl, Cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-hept
  • alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
  • An alkynyl group includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or Understood octinyl.
  • a C1 to C40 alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • aromatic or heteroaromatic ring system with 5 to 60, preferably 5-40 aromatic ring atoms, particularly preferably 5 to 30 aromatic ring atoms, which can be substituted by the above-mentioned radicals and which can be linked via any positions on the aromatic or heteroaromatic , for example, groups are understood which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, Spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-mon
  • the compound to be used according to the invention can comprise at least one structure of the formulas (Ila), (Mb) and / or (IIc), preferably selected from the compounds of the formulas (Ila), (Mb) and (IIc)
  • two groups Ar preferably the two groups Ar bonded to a nitrogen atom in formula (Mb), together form an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms which can be substituted by one or more radicals R, where the radical R has the meanings given above, in particular for formula (I).
  • the compound to be used according to the invention can comprise at least one structure of the formulas (IIb-1), (IIb-2), (IIb-3) and / or (IIb-4), preferably selected from the compounds of the formulas ( llb-1), (llb-2), (llb-3) and / or (llb-4) where the radicals X and R have the meaning given above, in particular for formula (I), the index m, identically or differently, 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2 , is particularly preferably 0 or 1.
  • At least one of the radicals Ar and / or R is selected from the group of phenyls, fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, quinazolines, quinoxalines, pyridines, quinolines, iso-quinolines, lactams , Triarylamines, dibenzofurans, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzthiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, naphthalenes, phenanthrenes, anthracenes, benzanthracenes, perylenes, chryenes, pyrenes, , Boroxines, boroie,
  • Fermer can preferably be provided that a radical R bonded directly to a nitrogen atom does not represent a group selected from OH, F, CI, Br, I, CN, N0 2 , N (Ar) 2 , N (R 1 ) 2 , where R 1 has the meaning given above, in particular for formula (I).
  • R 1 has the meaning given above, in particular for formula (I).
  • the structures of the formulas (I) and the preferred embodiments of these structures set out above and below do not have an NN bond.
  • At least one of the radicals Ar and / or R is selected from the group consisting of phenyl, orthometa- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2- , 3- or 4-fluorenyl, 9,9'-diaryl-fluorenyl 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2 -, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl,
  • substituents R are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar ') 2, a straight-chain alkyl group with 1 to 8 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms Atoms, or a branched or cyclic alkyl group with 3 to 8 carbon atoms, preferably with 3 or 4 carbon atoms, or an alkenyl group with 2 to 8 carbon atoms, preferably with 2, 3 or 4 carbon atoms, each with one or more radicals R 1 can be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each with one or several non-aromatic radicals R 1 can be substituted, but is preferably unsubstituted; optionally two substituents R 1 , preferably those bonded to adjacent carbon atoms, can
  • the substituents R are particularly preferably selected from the group consisting of Fl or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which can be substituted with one or more non-aromatic radicals R 1, but is preferably unsubstituted.
  • substituents R are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinoxalinyl, quinolinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4- dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, which can each be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • substituents R of the structures set out above and below preferably structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4), do not contain any condensed aromatic or heteroaromatic ring system, preferably not forming a condensed ring system. This includes the
  • the compound to be used according to the invention comprises a hole transport group, wherein preferably at least one of the groups Ar and / or R set out above, which inter alia in a structure according to the formulas (I), (IIa) to (IIc ) and / or (IIb-1) to (IIb-4) may be included, comprises, preferably represents, a hole transport group.
  • Hole transport groups are known to those skilled in the art, these preferably comprising triarylamine or carbazole groups.
  • the hole transport group comprises a group, preferably a group, which is selected from the formulas (H-1) to (H-3),
  • Ar 2 , Ar 3 , Ar 4 are each independently an aromatic ring system with 6 to 40 carbon atoms or a heteroaromatic ring system with 3 to 40 carbon atoms, which can each be substituted by one or more radicals R 1; p is 0 or 1;
  • Ar 1 is an aromatic ring system with 6 to 40 carbon atoms or a heteroaromatic ring system with 3 to 40 carbon atoms, which can be substituted by one or more radicals R 1 , and the radicals R 1 are the above, in particular for formula ( I) has the meaning set out above.
  • the presence of an NN bond is preferably excluded here.
  • the hole transport group comprises a group, preferably a group, which is selected from the formulas (H-4) to (H-26),
  • the presence of an NN bond is preferably excluded here.
  • the group Ar 2 can preferably form a continuous conjugation with the aromatic or heteroaromatic radical or the nitrogen atom to which the group Ar 2 according to the formulas (H-1) to (H-26) can be bonded.
  • Ar 2 is an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which can be substituted by one or more radicals R 1 , but is preferably unsubstituted where R 1 can have the meaning given above, in particular for formula (I).
  • Ar 2 particularly preferably stands for an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, which in each case can be substituted by one or more radicals R 1 , but is preferably unsubstituted, where R 1 is the can have in particular the meaning mentioned for formula (I).
  • Ar 2 set out in formulas (H-1) to (H-26), among other things, preferably stands for an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.
  • the group Ar 2 set out in formulas (H-1) to (H-26) is an aromatic ring system with at most two condensed aromatic and / or heteroaromatic 6-membered rings, preferably no condensed aromatic or heteroaromatic ring system with condensed 6-membered rings - Wrestling includes. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures. Structures which have no condensation, such as, for example, phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.
  • the group Ar 2 set out, inter alia, in formulas (H-1) to (H-26) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.
  • Ar 3 and / or Ar 4 identically or differently on each occurrence, represent an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system with 6 up to 12 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 , but is preferably unsubstituted, where R 1 can have the meaning given above, in particular in formula (I) .
  • the compound to be used according to the invention comprises a radical comprising electron transport groups, where preferably at least one of the groups Ar and / or R set out above, which, inter alia, have a structure according to the formulas (I), (IIIa) to (llc) and / or (llb-1) to (llb-4) may be included, a
  • Comprises electron transport group-comprising radical preferably represents.
  • Electron transport groups are well known in the art and promote the ability of compounds to transport and / or conduct electrons.
  • compounds to be used according to the invention show surprising advantages which comprise at least one structure selected from the group consisting of pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, quinoxalines, quinolines, isoquinolines, imidazoles and / or benzimidazoles, pyrimidines, triazines and quinazolines are particularly preferred.
  • These structures generally promote the ability of compounds to transport and / or conduct electrons.
  • the radical comprising electron transport groups stands for a group which can be represented by the formula (QL),
  • L 1 represents a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , and Q is an electron transport group, where R 1 is the has the meaning mentioned above, in particular for formula (I), and the dashed bond marks the attachment position.
  • the group L 1 can preferably form a continuous conjugation with the group Q and the atom, preferably the carbon or nitrogen atom, to which the group L 1 according to formula (QL) is bonded.
  • a continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings.
  • a further link between the aforementioned conjugated groups does not damage a conjugation.
  • the two aromatic rings are directly bound, whereby the sp 3 hybridized carbon atom in position 9 prevents condensation of these rings, but conjugation can take place, since this sp 3 hybridized carbon atom in position 9 is not necessarily between the electron-transporting group Q and the atom via which the group of the formula (QL) bonds to further structural elements of a compound.
  • a continuous conjugation can be formed in the case of a second spirobifluorene structure if the connection between the group Q and the aromatic or heteroaromatic radical to which the group L 1 according to formula (QL) is bonded via the same phenyl group of the spirobifluorene structure or via Phenyl groups of the spirobifluorene structure, which are directly bonded to one another and lie in one plane, takes place. If the connection between the group Q and the aromatic or heteroaromatic radical to which the group L 1 according to formula (QL) is bound, is via different phenyl groups of the second spirobifluorene structure, which are connected via the sp 3 hybridized carbon atom in position 9 the conjugation interrupted.
  • L 1 represents a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which can be substituted by one or more radicals R 1 , but is preferably unsubstituted, where R 1 can have the meaning given above, in particular for formula (I).
  • L 1 particularly preferably stands for an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, which in each case can be substituted by one or more radicals R 2 , but is preferably unsubstituted, where R 2 is the can have in particular the meaning mentioned for formula (I).
  • L 1 set out in formula (QL), inter alia, preferably stands, identically or differently on each occurrence, for a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.
  • the group L 1 set out in formula (QL) comprises an aromatic ring system with at most two condensed aromatic and / or heteroaromatic 6-membered rings, preferably no condensed aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures.
  • Structures which have no condensation such as, for example, phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.
  • Suitable aromatic or heteroaromatic ring systems L 1 are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, especially branched terphenylene, quaterphenylene, especially branched quaterphenylene, fluorenylene, Spirobifluorenylen, Dibenzofuranylen, Dibenzothienylen and Carbazolylen, each by a or more radicals R 1 can be substituted, but are preferably unsubstituted.
  • the group L 1 set out, inter alia, in formula (QL) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.
  • the group Q or the electron transport group set out in the formula (QL), inter alia, can preferably be selected from structures of the formulas (Q-1), (Q-2), (Q-4), (Q-4), (Q- 5), (Q-6),
  • Q ' represents CR 1 or N, identically or differently on each occurrence
  • Q “represents NR 1 , 0 or S; where at least one Q 'is equal to N and
  • R 1 is as defined above, in particular in formula (I).
  • the group Q set out in the formula (QL) or the electron transport group can preferably be selected from a structure of the formulas (Q-11), (Q-12), (Q-13),
  • the group Q or the electron transport group set out inter alia in the formula (QL) can be selected from structures of the formulas (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22)
  • the structures of the formulas (Q-16), (Q-17), (Q-18) and (Q-19) are preferred here.
  • the group Q or the electron transport group set out inter alia in the formula (QL) can be selected from structures of the formulas (Q-23), (Q-24) and / or (Q-25),
  • the group Q or the electron transport group set out inter alia in the formula (QL) can be selected from structures of the formulas (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30),
  • the group Q or the electron transport group set out in the formula (QL), inter alia, can preferably be selected from structures of the formulas (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), Formula (Q-43) Formula (Q-44) in which the symbols Ar 1 and R 1 have the meaning given above, inter alia, for formula (I) and / or (H-2) or (H-3), the dashed bond the connection position is marked and m 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n 0, 1, 2 or 3, preferably 0 or 1, n 0,
  • Ar 1 identically or differently on each occurrence, represents an aromatic or heteroaromatic ring system, preferably an aryl or Heteroaryl radical with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferred for an aromatic ring system, preferably an aryl radical with 6 to 12 aromatic ring atoms or a heteroaromatic ring system, preferably a heteroaryl group with 5 to 13 aromatic ring atoms, each can be substituted by one or more radicals R 2 , but is preferably unsubstituted, where R 2 can have the meaning shown above, in particular in formula (I).
  • Ar 1 preferably stands for an aryl or heteroaryl radical, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group, for example a C. - Or N atom of the groups (H-1) to (H-26) or (Q-26) to (Q-44) shown above.
  • Ar 1 in the formulas (H-1) to (H-26) or (Q-26) to (Q-44) advantageously represents an aromatic ring system with 6 to 12 aromatic ring atoms, which with one or more radicals R 2 may be substituted, but is preferably unsubstituted, where R 2 can have the meaning given above, in particular for formula (I).
  • the radicals R 1 or R 2 in the formulas (H-1) to (H-26) or (Q-1) to (Q-44) preferably form with the ring atoms of the aryl group or heteroaryl group Ar 1 , Ar 2 , Ar 3 and / or Ar 4 to which the radicals R 1 or R 2 are bonded, not a fused ring system. This includes the formation of a condensed ring system with possible substituents R 2 which can be bonded to the radicals R 1.
  • the group Ar ', Ar 1 , Ar 2 , Ar 3 and / or Ar 4 is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl , especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1- , 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4- Carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and
  • At least two radicals Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) each have one Include, preferably represent, hole transport group.
  • At least one of the radicals Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises two hole transport groups.
  • a hole transport group can be regarded as the radical R 1 , in which case the substituents R 1 set out in the structures of the formulas (H-1) to (H-26) are to be replaced by radicals R 2.
  • At least two radicals Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) each have one Electron transport group-comprising radical include, preferably represent.
  • At least one of the radicals Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises two electron transport groups Includes leftovers.
  • a radical comprising electron transport groups can be regarded as the radical R 1 , in which case the substituents R 1 set out in the structures of the formulas (QL) and / or (Q-1) to (Q-44) are replaced by radicals R 2 are to be replaced.
  • At least one of the radicals Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises, preferably represents, a hole transport group, and at least one of the radicals R and / or Ar comprises, preferably represents, a radical comprising electron transport groups.
  • a radical comprising electron transport groups or a hole transport group can be regarded as the radical R 1 , in which case the structures of the formulas (QL), (Q-1) to (Q-44) or (H-1) to ( H- 26) R substituents set forth are to be replaced by radicals R 1. 2
  • At least one of the radicals Ar and / or R comprises at least one group which leads to wide-band-gap materials.
  • group that leads to wide-band-gap materials states that the compounds can be used as wide-band-gap materials, so that the compounds have corresponding groups. Wide band gap materials are discussed in more detail later.
  • At least one of the radicals Ar and / or R comprises at least one group which leads to materials which are used as host material.
  • group that leads to materials that are used as host material states that the compounds can be used as host materials, so that the compounds have corresponding groups. Host materials are set out in more detail later.
  • the compound comprises a condensed aromatic or heteroaromatic ring system with at least 2, preferably three condensed rings, which can optionally be substituted.
  • at least one of the radicals Ar and / or R in structures of the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises at least one aromatic or heteroaromatic ring system with two, preferably with three fused aromatic or heteroaromatic rings.
  • the aromatic or heteroaromatic ring system with two, preferably three, condensed aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar-1) to (Ar-17) where X 'is N or CR 1 , preferably CR 1 , L 1 is a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1, where R 1 has the meaning set out above, in particular for formula (I), and the dashed bond marks the attachment position.
  • the aromatic or heteroaromatic ring system with two, preferably three, condensed aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar'-1) to (Ar'-17) (Ar'-10) (Ar'-11) (Ar'-12) where L 1 represents a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , where R 1 has the meaning given above, in particular for formula (I) has, the dashed bond marks the attachment position and the following applies to the indices: p is 0 or 1; e is 0, 1 or 2, preferably 0 or 1; j is independently on each occurrence 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably preferably 0 or 1; h on each occurrence is independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably preferably 0 or 1; s is an integer in the range from 0
  • the sum of the indices p, e, j, h and s in the structures of the formulas (Ar'-1) to (Ar'-17) is preferably at most 3, preferably at most 2 and particularly preferably at most 1.
  • the structures of the formulas (Ar-1) to (Ar-17) and / or (Ar'-1) to (Ar'-17) set out above are particularly preferred radicals for compounds which are suitable for use as fluorescent emitters or as blue OLED materials are suitable.
  • the group L 1 in the structures of the formulas (Ar-1) to (Ar-17) and / or (Ar'-1) to (Ar'-17) presented above represents an aromatic or represents a heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , where R 1 has the meaning given above, in particular for formula (I).
  • substituents R 1 are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar “ ) 2, a straight-chain alkyl group with 1 to 8 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 8 carbon atoms, preferably with 3 or 4 carbon atoms, or an alkenyl group with 2 to 8 carbon atoms, preferably with 2, 3 or 4 carbon atoms, each of which can be substituted with one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably 6 to 13 aromatic ring atoms, which in each case can be substituted by one or more non-aromatic radicals R 1 , but is preferably unsubstituted; optionally two substituents R 1 , preferably those bonded to adjacent carbon
  • the substituents R 1 are very particularly preferably selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which is substituted with one or more non-aromatic radicals R 2 can be, but is preferably unsubstituted.
  • substituents R 1 are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl , 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, which can each be substituted by one or more radicals R 2 , but are preferably unsubstituted.
  • the substituents R 1 of an aromatic or heteroaromatic ring system with further ring atoms of the aromatic or heteroaromatic ring system do not form a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system.
  • R 1 or Ar stands for a group, which is selected from the formulas (R 1 -1) to (R 1 -43), or in a structure according to formula (H-1) to (H-26), (QL), (Q-1) to (Q -44), (Ar-1) to (Ar-17) and / or (Ar'-1) to (Ar'-17) at least one R 1 represents a group selected from the formulas (R 1 - 1) to (R 1 - 43) Formula (R 1 -22) Formula (R 1 -23) Formula (R 1 -24) Formula (R 1 -37) Formula (R 1 -38) Formula (R 1 -39)
  • Y 3 is 0, S or NR 2 , preferably 0 or S; k is independently 0 or 1 on each occurrence; i is independently 0, 1 or 2 on each occurrence; j is independently 0, 1, 2 or 3 on each occurrence; h is independently on each occurrence 0, 1, 2, 3 or 4; g is independently at each occurrence 0, 1, 2, 3, 4 or 5;
  • R 2 can have the meaning mentioned above, in particular for formula (I), and the dashed bond marks the attachment position.
  • the groups of the formulas R 1 -1 to R 1 -28 are preferred, the groups 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 are particularly preferred. It can preferably be provided that the sum of the indices k, i, j, h and g in the structures of the formulas (R 1 -1) to (R 1 -43) is in each case at most 3, preferably at most 2 and particularly preferably at most 1 .
  • radicals R 2 in the formulas (R 1 -1) to (R 1 -43) preferably form with the ring atoms of the aryl group or fleteroaryl group to which the radicals R 2 are bound, no condensed aromatic or heteroaromatic ring system, preferably no condensed ring system.
  • radicals of the formulas (R 1 -1) to (R 1 -43) set out above represent preferred radicals Ar according to formula (I) or Ar 3 , Ar 4 according to formulas (H-1) to (H-3) or preferred embodiments of these formulas, in which case the groups R 2 set out in formulas (R 1 -1) to (R 1 -43) are to be replaced by radicals R 1.
  • the preferences set out above with regard to formulas (R 1 -1) to (R 1 -43) apply accordingly.
  • the compound comprises at least one linking group which is selected from the formulas (L 1 -1) to (L 1 -76), preferably in the structure according to formulas (H-1) to (H-26) ) the group Ar 2 is selected from the formulas (L 1 -1) to (L 1 -76) or the electron transport group is connected to further structural elements via a connecting group which is selected from the formulas (L 1 -1) to ( L 1 -76) or the radical L 1 in formulas (QL), (Ar-1) to (Ar-17) and / or (Ar'-1) to (Ar'-17) represents a group which has been selected is from the formulas (L 1 -1) to (L 1 -76), Formula (U-19) Formula (L 1 -20) Formula (L 1 -21)
  • Formula (U-34) Formula (U-35) Formula (L 1 -36) Formula (U-52) Formula (U-53) Formula (L 1 -54)
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -76) is in each case at most 3, preferably at most 2 and particularly preferably at most 1 .
  • Preferred compounds with a group of the formulas (H-1) to (H-26) include a group Ar 2 , which is selected from one of the formulas (L 1 -1) to (U-46) and / or (L 1 - 57) to (L 1 -76), preferably of the formula (L 1 -1) to (L 1-32) and / or (L 1 -57) to (-76 L 1), particularly preferably of the formula (L 1 -1) to (U-10) and / or (L 1 -57) to (U-68).
  • a group Ar 2 which is selected from one of the formulas (L 1 -1) to (U-46) and / or (L 1 - 57) to (L 1 -76), preferably of the formula (L 1 -1) to (L 1-32) and / or (L 1 -57) to (-76 L 1), particularly preferably of the formula (L 1 -1) to (U-10) and / or (L 1 -57) to (U-68).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (U-46) and / or (L 1 -57) to (L 1 -76), preferably of the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -76), especially preferably of the formula (L 1 -1) to (L 1 - 10) and / or (L 1 -57) to (L 1 -68) are each at most 3, preferably at most 2 and particularly preferably at most 1.
  • Preferred compounds with a group of the formula (QL) include a group L 1 which represents a bond or which is selected from one of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -76), preferably of the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -76), especially preferably of the formula (L 1 -1 ) to (L 1 -10) and / or (L 1 -57) to (L 1 -68).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -76) , preferably of the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -76), particularly preferably of the formula (L 1 -1) to (L 1 -10 ) and / or (L 1 -57) to (L 1 -68) are each at most 3, preferably at most 2 and particularly preferably at most 1.
  • Preferred compounds having a group of the formulas (Ar-1) to (Ar-17) and / or (Ar'-1) to (Ar'-17) comprise a group L 1 which represents a bond or which is selected from one of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -76), preferably of the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (-76 L 1), particularly preferably of the formula (L 1 -1) to (L 1 - 10) and / or (L 1 -57) to (L 1 -68).
  • radicals R 1 in the formulas (L 1 -1) to (L 1 -76) preferably do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system, with the ring atoms of the aryl group or heteroaryl group to which the radicals R 1 are bonded .
  • a compound which can be used according to the invention can be represented by at least one of the structures according to formula (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4).
  • Compounds comprising structures according to the formula preferably have (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4), a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and very particularly preferably less than or equal to 1200 g / mol.
  • preferred compounds which can be used according to the invention are distinguished by the fact that they can be sublimed. These compounds generally have a molar mass of less than approx. 1200 g / mol.
  • the compound according to the invention is substituted by aromatic or heteroaromatic groups R 1 or R 2 , it is preferred if these do not have any aryl or heteroaryl groups with more than two aromatic six-membered rings fused directly to one another.
  • the substituents particularly preferably have no aryl or heteroaryl groups with six-membered rings fused directly to one another. This preference is due to the low triplet energy of such structures.
  • Condensed aryl groups with more than two aromatic six-membered rings condensed directly to one another which are nevertheless also suitable according to the invention, are phenanthrene and triphenylene, since these too have a high triplet level.
  • preferred compounds can contain corresponding groups, for example fluorene, anthracene and / or pyrene groups, which can be substituted with groups R 1 or R 2 or which are substituted by corresponding substitution of the groups (L 1 -1) to (L 1 -76) or (R 1 -1) to (R 1 -43) with the substituents R 1 or R 2 are formed.
  • R 2 is , for example, in a structure according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) and preferred embodiments of this structure or the structures , in which reference is made to these formulas, selected identically or differently from the group on each occurrence consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 10 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, particularly preferably with 5 to 13 aromatic ring atoms, which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.
  • radicals R 2 with the ring atoms of the aryl group or heteroaryl group to which the radicals R 2 are bonded preferably do not form a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system.
  • the compound according to the invention is not in direct contact with a metal atom, and preferably does not represent a ligand for a metal complex.
  • the present invention again further provides a compound comprising at least one structure of the formula (III), preferably a compound according to the formula (III),
  • HetAr is a heteroaromatic ring system with 5 to 60 aromatic ring atoms which can be substituted by one or more radicals R 1 , the group HetAr can form a ring system with at least one group Ar, one radical R or another group, where HetAr preferably stands for a group which is selected from the formulas (H-1) to (H-26) defined above or which is selected from the previously defined formulas (QL) and (Q-1) to (Q-44).
  • the compounds according to the invention comprise a structure of the formula (IVa), (IVb) and / or (IVc), the compounds according to the invention being particularly preferably selected from the compounds of the formula (IVa), ( IVb) and / or (IVc),
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table above include radicals R 1 , which are preferably an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 represent up to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 R 1 -3, R 1 -4, R 1 -10, R: 1 - 11 R 1 R 1 -12 -13 -14 R 1 R 1 R 1 R
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVb) shown in the table above include radicals R 1 , which are preferably an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 represent up to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 R 1 -3, R 1 -4, R 1 -10, R: 1 - 11 R 1 R 1 -12 -13 -14 R 1 R 1 R 1 R
  • the radical HetAr and at least one of the radicals Ar and / or R in a structure according to the formulas (III), (IVa), (IVb) and / or (IVc) each comprise a hole transport group, preferably represent.
  • the radical HetAr comprises two hole transport groups in a structure according to the formulas (III), (IVa), (IVb) and / or (IVc).
  • a hole transport group can be viewed as a radical R 1 in which case the substituents R 1 set out in the structures of the formulas (H-1) to (H-26) are to be replaced by radicals R 2.
  • the residue FletAr and at least one of the residues Ar and / or R in a structure according to the formulas (III), (IVa), (IVb) and / or (IVc) each comprise an electron transport group Rest include, preferably represent.
  • the residue FletAr in a structure according to the formulas (III), (IVa), (IVb) and / or (IVc) comprises two residues comprising electron transport groups.
  • a radical comprising electron transport groups can be regarded as the radical R 1 , in which case the substituents R 1 set out in the structures of the formulas (QL) and / or (Q-1) to (Q-44) are replaced by radicals R 2 are to be replaced.
  • At least one of the radicals HetAr, Ar and / or R in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises, preferably represents, a hole transport group, and at least one of the radicals HetAr, Ar and / or R comprises, preferably represents, a radical comprising electron transport groups.
  • the radical HetAr in a structure according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) comprises both a radical comprising electron transport groups and a Hole transport group.
  • a radical comprising an electron transport group or a hole transport group can be regarded as the radical R 1 , in which case the structures of the formulas (QL), (Q-1) to (Q-44) or (H-1) to (H -26) R substituents set forth are to be replaced by radicals R 1. 2
  • the present invention again further provides a compound comprising at least one structure of the formula (V), preferably a compound according to the formula (V), where the symbols X and W have the meanings given above, in particular for formula (I), and KonAr represents an aromatic or heteroaromatic ring system with two, preferably three, fused aromatic or heteroaromatic rings, which has 10 to 60 aromatic ring atoms, preferably 12 to 40 aromatic ones Has ring atoms, wherein the aromatic or heteroaromatic ring system can be substituted with one or more radicals R 1 , wherein the group KonAr can form a ring system with at least one group Ar, one radical R, one group X or another group, KonAr preferably for a group which is selected from the formulas (Ar-1) to (Ar-17) and (Ar'-1) to (Ar'-17) defined above, particularly preferably a group which is selected from the formulas (Ar-3) to (Ar-17) and (Ar'-3) to (AM 7) defined above.
  • the compounds according to the invention comprise a structure of the formula (Via), (VIb) and / or (VIc), the compounds according to the invention being particularly preferably selected from the compounds of the formula (Via), ( Vlb) and / or (Vlc),
  • the groups of the formulas Ar-5 or Ar'-5 of the compounds shown in the table presented above with structures of the formulas (V), (Via), (Vlb) and / or (Vlc) radicals R 1 which preferably include represent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which can be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Ar-5 and Ar'-5 of the compounds with structures of the formulas (V), (Via), (Vlb) and / or (Vlc) set forth in the table set out above preferably have at least a radical R 1 which is selected from the formulas (R 1 -1) to (R 1 - 43), preferably groups of the formulas R 1 -1 to R 1 -28 and R 1 -34 to R 1 -38, particularly preferred groups of the formulas R 1 -1, R 1 -3, R 1 -4, R 1 -10,
  • the compound according to the invention can comprise at least one structure of the formulas (Vlb-1) and / or (Vlb-2), preferably selected from the compounds of the formulas (Vlb-1) and / or (Vlb-2) , where the radicals X and R have the meaning given above, in particular for formula (I), the index m, identically or differently, 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2 , is particularly preferably 0 or 1 and the ring KON is an aromatic or heteroaromatic ring system with two, preferably with three fused aromatic or heteroaromatic rings, which has 10 to 60 aromatic ring atoms, preferably 12 to 40 aromatic ring atoms, the aromatic or heteroaromatic ring system can be substituted by one or more radicals R 1 , where R 1 can have the meaning given above, in particular for formula (I).
  • the ring KON shown in formulas (Vlb-1) and / or (Vlb-2) binds to the ring with two nitrogen atoms via adjacent carbon atoms, so that the ring on which the ring KON is condensed is a 5 Ring represents.
  • the ring KON in formulas (Vlb-1) and / or (Vlb-2) is fused to the ring with two nitrogen atoms.
  • the ring KON forms a partial structure of the formulas (KON-1) to (KON-10) in a structure according to formulas (Vlb-1) and / or (Vlb-2)
  • the ring KON forms a partial structure of the formulas (KON'-1) to (KON'-10) in a structure according to formulas (Vlb-1) and / or (Vlb-2) where R 1 has the meaning given above, in particular for formulas (I), the index o is 0, 1 or 2, preferably 0 or 1, the index n is 0, 1, 2, or 3, preferably 0, 1 or 2 and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the N atoms in each case at the positions marked by o on the aromatic or heteroaromatic ring system Binds 5 to 60 carbon aromas to form a ring.
  • the compounds according to the invention comprise a structure of the formula (Vlb-3) to (Vlb-10), the compounds according to the invention being particularly preferably selected from the compounds of the formulas (Vlb-3) to ( Vlb-10)
  • Formula (Vlb-7) Formula (Vlb-8) where the symbols R and R 1 have the meanings given above, in particular for formula (I), the index s 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly is preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2, index I. Is 0, 1 or 2.
  • Structures of the formulas (VIb-1) to (VIb-8) can preferably have hole transport and / or hole guiding groups, as defined above.
  • radicals R 1 which are preferably an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each of which can be substituted by one or more non-aromatic radicals R 2 ;
  • the groups of the formulas Q-11 to Q-25 preferably have those in the table set out above Compounds shown with structures of the formula (IVa) at least one radical R 1 , preferably at least two R 1, which / is / are selected from among the formulas (R 1 -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably groups of the formulas R 1 -1, R 1 -3, R 1 -4, R 1 -
  • the present invention again further provides a compound comprising at least one structure of the formula (VII), preferably a compound of the formula (VII), where the symbols Ar and W have the meanings given above, in particular for formula (I), and the ring KON represents an aromatic or heteroaromatic ring system with two, preferably three, fused aromatic or heteroaromatic rings, which has 10 to 60 aromatic ring atoms, preferably 12 to Has 40 aromatic ring atoms, it being possible for the aromatic or heteroaromatic ring system to be substituted by one or more radicals R 1 , where R 1 can have the meaning given above, in particular for formula (I).
  • the ring KON shown in formula (VII) binds to the five-membered ring with the groups W and SO2 via adjacent carbon atoms, so that the ring on which the ring KON is fused represents a 5-membered ring.
  • the ring KON in formula (VII) is condensed onto the ring with the groups W and SO2.
  • the ring KON in a structure according to formula (VII) has a partial structure of the formulas (KON-1) to (KON-10) and / or the formulas (KON'-1) to (KON'-10 ) forms, as stated above, with the group W and SO2 respectively on the positions marked by o binds to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms to form a ring.
  • the compounds according to the invention comprise a structure of the formulas (VII-1) to (VII-10), the compounds according to the invention being particularly preferably selected from the compounds of the formulas (VII-1) to ( VII-10)
  • Formula (VII-5) Formula (VII-6) Formula (VII-9) Formula (VII-10) where the symbols R 1 and Ar have the meanings given above, in particular for formula (I), the index s 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2, index I is 0, 1 or 2.
  • radicals R 1 which are preferably an aromatic or represent a heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which can be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 , R 1 -3, R 1 -4, R 1 -10, R 1 -11, R 1
  • the present invention again further provides a compound comprising at least one structure of the formula (VIII), preferably a compound according to the formula (VIII), Formula (VIII) where the symbols X, Ar and W have the meanings given above, in particular for formula (I), where the structure A / erbigation has at least one aromatic or heteroaromatic ring system with 5 to 60 carbon atoms to which a non-aromatic or non-heteroaromatic ring system is condensed.
  • the non-aromatic or non-heteroaromatic ring system which is fused to an aromatic or heteroaromatic ring system with 5 to 60 carbon atoms, is a non-aromatic or non-heteroaromatic multicyclic ring system with at least 2 rings, preferably at least 3 rings represents.
  • the non-aromatic or non-heteroaromatic ring system which is fused to an aromatic or heteroaromatic ring system with 5 to 60 carbon atoms, to two adjacent ring atoms, preferably carbon atoms of the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms binds.
  • the binding sites of the non-aromatic or non-heteroaromatic ring system are preferably in the otho position with respect to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms.
  • Formula RA-7 Formula RA-8 Formula RA-9 where R 1 has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points to the atoms of the groups to which the two radicals R bond, and the other symbols have the following meanings:
  • R 1 is on each occurrence, identically or differently, F, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy - Or thioalkoxy group with 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group can each be substituted by one or more radicals R 2 , one or more nonadjacent CFh groups being substituted by
  • Ring atoms which in each case can be substituted by one or more radicals R 2 , or an aryloxy or fleteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2;
  • two radicals R a here can also form a ring system with one another;
  • s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2;
  • t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, or 4, particularly 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, particularly preferably 0, 1 or 2.
  • the at least two radicals R which form the structures of the formulas (RA-1) to (RA-12) and form a condensed ring, represent radicals R from adjacent X groups.
  • the at least two radicals R form a condensed ring with the other groups to which the two radicals R bond, the two radicals R preferably at least one of the structures of the formulas (RA-1a) to (RA- 4f)
  • Formula RA-4a Formula RA-4b Forme
  • RA.4c Formula RA-4f
  • the symbols R a and R 1 and the indices s and t have the meanings given above, in particular for formulas (RA-1) to (RA-12), the dashed bonds represent the attachment points and the index m 0 , 1, 2, 3 or 4, preferably 0, 1 or 2.
  • At least two radicals R form a condensed ring with the other groups to which the two radicals R bond, the two radicals R forming structures of the formula (RB)
  • Formula RB where R 1 has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points, the index 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.
  • radicals R which form the structures of the formula (RB) and form a condensed ring, represent radicals R from adjacent X groups.
  • radicals R which form structures of the formula (RB) and form a condensed ring
  • radicals R are adjacent, in particular are in the ortho position, so that the ring with the group Y 5 is a 5- Ring represents.
  • the compounds according to the invention have a structure of the formula (VIII-1) to (VIII-13), the compounds according to the invention being particularly preferably selected from the compounds of the formulas (VIII-1) to (VIII-13), the compounds having at least one condensed ring
  • the condensed ring in particular in formulas (VIII) and (VIII-1) to (VIII-13), is preferred by at least one of the structures of the formulas (RA-1) to (RA-12), the formulas (RA-1a ) to (RA-4f) and / or the formula (RB) together with the ring atoms marked with the symbol o, whereby structures of the formulas (RA-1) to (RA-12), the formulas (RA -1a) to (RA-4f) are particularly preferred.
  • radicals R 1 which are preferably an aromatic table or represent a heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, which can in each case be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 , R 1 -3, R 1 -4, R 1 -10, R 1 -11, R
  • Yet another subject matter of the present invention is a compound which has exactly two, exactly three or exactly four structures according to formula (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) and / or their preferred embodiments, in particular structures according to the formula (III), (IVa) to (IVc), (V), (Via) to (Vlc), (VII), (VII-1) to (VII-10), (VIII), (VIII- 1) to (VI 11-10).
  • the compounds are particularly preferably selected from compounds of the formulas (IXa) to (IXc), where the symbols Ar and W have the meanings given above, in particular for formula (I), X stands for N, CR or C, if a group L 1 binds to this, with the proviso that not more than two of the groups X in a cycle represent N; and L 1 represents a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , L 1 preferably representing a bond or a group selected is from the formulas (L 1 -1) to (L 1 -76) defined above, where in formula (VIIa) the group L 1 particularly preferably does not represent a bond.
  • the compounds are particularly preferably selected from compounds of the formulas (Xa) to (Xc), Formula (Xc) where the symbols R and Ar have the meanings given above, in particular for formula (I), the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and L 1 is the above, has in particular the meaning mentioned for formula (IXa) to (IXc), preferably represents a group which is selected from the formulas (L 1 -1) to (L 1 -76) defined above, where in formulas (IXa) to ( IXc) the group L 1 particularly preferably does not represent a bond.
  • the compounds selected from V are particularly preferred.
  • the compounds are particularly preferably selected from compounds of the formulas (XIIa) to (XIIc),
  • the compound according to the invention can comprise at least one structure of the formulas (XIII-1) and / or (XIII-2), preferably selected from the compounds of the formulas (XIII-1) and / or (XIII-2) , where the radicals X and R have the meaning given above, in particular for formula (I), the index m, identically or differently, 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2 , is particularly preferably 0 or 1, the index z is 2, 3 or 4 and the ring AR n is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 1 , where R 1 is the may have the meaning given above, in particular for formula (I).
  • the ring AR n preferably represents an aromatic or n heteroaromatic ring system with two, preferably with three condensed aromatic or heteroaromatic rings, which has 10 to 60 aromatic ring atoms, preferably 12 to 40 aromatic ring atoms.
  • the ring AR n shown in formulas (XIII-1) and / or (XIII-2) is attached to the ring with two via adjacent carbon atoms
  • Nitrogen atoms binds, so that the ring to which the ring KON is fused represents a 5-ring.
  • the ring AR n in formulas (XIII-1) and / or (XIII-2) is fused to the ring with two nitrogen atoms. 0
  • the index o is 0, 1 or 2, preferably 0 or 1
  • the index n is 0, 1, 2, or 3, preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2
  • the index I is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1 or 2
  • the groups W or S0 2 binds in each case at the positions marked by o to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms to form a ring.
  • the sum of the indices o, n, m and I is at most 6, preferably at most 4 and particularly preferably at most 2.
  • Structures of the formulas (XIII-1) and (XIII-2) can preferably have hole transport and / or hole guiding groups, as defined above.
  • Compounds according to the invention with structures of the formulas (XIII-1) and (XIII-2) which have the following properties are also particularly preferred:
  • radicals R 1 which are preferably an aromatic or heteroaromatic ring system with 6 represent up to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which can be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 , R 1 -3, R 1 -4, R 1 - 10 R 1 -1 1 R 1 -12 R1-13 r
  • Yet another object of the present invention is a compound of the formula (XIV), where the symbols Ar and W have the meanings given above, in particular for formula (I), the index z is 2, 3 or 4 and the ring AR n is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, with one or more R 1 can be substituted, where R 1 can have the meaning given above, in particular for formula (I).
  • the ring AR n in a structure according to formula (XIV) is a partial structure of the formulas (AR n -1) to (AR n -29) and / or the formulas (AR nl -1) to (AR nl -30), as set out above, the group W or SO2 bonding in each case to the positions marked by o to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms to form a ring.
  • the ring AR n in a structure according to formula (XIV) binds via adjacent carbon atoms to the five-membered ring with the groups W and SO2, so that the ring to which the ring AR n is in a structure according to formula ( XIV) is condensed represents a 5-ring.
  • the ring KON in formula (XIV) is fused to the ring with the groups W and SO2.
  • the preferences set out above for structures / compounds of the formula (I) apply. This is especially true for groups W and Ar. Structures of the formulas (XIV) can preferably have hole transport and / or hole conducting groups, as these have been defined above.
  • radicals R 1 which are preferably an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 represent up to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 2;
  • the groups of the formulas Q-11 to Q-25 of the compounds with structures of the formula (IVa) shown in the table presented above preferably have at least one radical R 1 , preferably at least two radicals R 1 , which is / are selected from from the formulas (1 R -1) to (R 1-43), preferably groups of the formulas R 1 R -1 to 1 -28, and R 1 to R -34 1 -38, particularly preferably from groups of the formulas R 1 -1 R 1 -3, R 1 -4, R 1 -10, R: 1 - 11 R 1 R 1 -12 -13 -14 R 1 R 1 R 1 R 1 R 1
  • the compounds according to the invention can in principle be prepared by various methods. However, the methods described below have proven to be particularly suitable.
  • the present invention therefore further provides a process for the preparation of the compounds according to the invention, preferably compounds comprising structures of the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4), in which in a coupling reaction a compound comprising at least one benzisothiazole group is linked to a compound comprising at least one aromatic or heteroaromatic group.
  • Suitable compounds comprising at least one heterocyclic structure can in many cases be obtained commercially, the starting compounds set out in the examples being obtainable by known processes, so that reference is made to them.
  • the compounds according to the invention comprising structures according to formula (I), can be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR and / or HPLC).
  • the compounds according to the invention can also have suitable substituents, for example by longer alkyl groups (approx. 4 to 20 carbon atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups, which allow solubility cause in common organic solvents, so that the compounds are soluble, for example, in toluene or xylene at room temperature in sufficient concentration to be able to process the compounds from solution.
  • These soluble compounds are particularly suitable for processing from solution, for example by printing processes.
  • the compounds of the present invention can contain one or more crosslinkable groups.
  • Networkable group means a functional group that is able to react irreversibly. This creates a crosslinked material that is insoluble.
  • the crosslinking can usually be assisted by heat or by UV, microwave, X-ray or electron radiation. In this case, there is too little by-product formation during crosslinking.
  • the crosslinkable groups that can be contained in the functional compounds crosslink very easily, so that lower amounts of energy are required for crosslinking (eg ⁇ 200 ° C. for thermal crosslinking).
  • crosslinkable groups are units which contain a double bond, a triple bond, a precursor which is capable of in situ formation of a double or triple bond, or a heterocyclic, addition-polymerizable radical.
  • Crosslinkable groups include vinyl, alkenyl, preferably ethenyl and propenyl, C4-2o-cycloalkenyl, azide, oxirane, oxetane, di (hydrocarbyl) amino, cyanate ester, hydroxy, glycidyl ether, Ci-io-alkyl acrylate, Ci-io-alkyl meth- acrylate, alkenyloxy, preferably ethenyloxy, perfluoroalkenyloxy, preferably perfluoroethenyloxy, alkynyl, preferably ethynyl, maleimide, cyclobutylphenyl, tri (Ci-4) -alkylsiloxy and tri (Ci-4)
  • the compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is possible in particular with compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups such as olefins or oxetanes. These can be used as monomers for producing corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization takes place preferably via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups.
  • the compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore also relates to oligomers, polymers or dendrimers containing one or more of the above-listed structures of the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or compounds according to the invention, where one or more bonds of the compounds according to the invention or of the structures of the formulas (I),
  • oligomer or dendrimer for the polymer, oligomer or dendrimer are present.
  • these therefore form a side chain of the oligomer or polymer or are in the main chain connected.
  • the polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below are 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%, are present.
  • Suitable and preferred comonomers which form the polymer backbone are selected from fluorene (e.g. according to EP 842208 or WO 2000/022026), spirobifluoren (e.g.
  • the polymers, oligomers and dendrimers can also contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units. Furthermore, compounds according to the invention which are distinguished by a high glass transition temperature are of particular interest.
  • compounds according to the invention are particularly preferred, comprising structures according to the formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below are preferred, which have a glass transition temperature of at least 70 ° C., particularly preferably of at least 110 ° C., very particularly preferably of at least 125 ° C. and particularly preferably of at least 150 ° C., determined according to DIN 51005 (version 2005-08).
  • formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It can be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (- ) -Fenchon,
  • the present invention therefore also provides a formulation or a composition containing at least one compound according to the invention and at least one further compound.
  • the further compound can be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation.
  • the further compound can, however, also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and / or a further matrix material. Suitable emitting
  • compositions comprising a combination
  • fluorescent emitters phosphorescent emitters, emitters which show TADF (thermally activated delayed fluorescence)
  • host materials exciton blocking materials, electron injection materials, electron transport materials, Electron blocking materials, hole injection materials, hole conductor materials, hole blocking materials, n-dopants, p-dopants, wide-band gap materials and / or charge generation materials.
  • compositions containing at least one compound comprising at least one structure according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or those above and Preferred embodiments set out below and at least one wide-band-gap material, wide-band-gap material being understood to mean a material within the meaning of the disclosure of US Pat. No. 7,294,849.
  • These systems show particularly advantageous performance data in electroluminescent devices.
  • the additional compound can preferably have a band gap of 2.5 eV or more, preferably 3.0 eV or more, very preferably 3.3 eV or more.
  • the band gap can be calculated using the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).
  • Molecular orbitals especially the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels and the energy of the lowest triplet state Ti or the lowest excited singlet state Si of the materials are determined using quantum chemical calculations.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • TD-SCF / DFT / Default Spin / B3PW91 with the basic set “6-31 G (d)” is used (Charge 0, Spin Singlet).
  • the geometry is optimized using the “Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet” method.
  • the energy calculation is analogous to the method described above for the organic substances, with the difference that the basic set “LanL2DZ” is used for the metal atom and the basic set “6-31 G (d)” is used for the ligands.
  • the HOMO energy level HEh or LUMO energy level LEh in Hartree units is obtained from the energy bill. From this, the HOMO and LUMO energy levels calibrated using cyclic voltammetry measurements are determined in electron volts as follows:
  • these values are to be viewed as HOMO or LUMO energy levels of the materials.
  • the lowest triplet state Ti is defined as the energy of the triplet state with the lowest energy, which results from the quantum chemical calculation described.
  • the lowest excited singlet state Si is defined as the energy of the excited singlet state with the lowest energy, which results from the quantum chemical calculation described.
  • the method described here is independent of the software package used and always delivers the same results. Examples of programs often used for this purpose are "Gaussian09W” (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).
  • the present invention also relates to a composition
  • a composition comprising at least one compound comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below as well at least one phosphorescent emitter, the term phosphorescent emitter also being understood to mean phosphorescent dopants.
  • a dopant in a system comprising a matrix material and a dopant, is understood to mean that component whose proportion in the mixture is the smaller.
  • a matrix material in a system comprising a matrix material and a dopant is understood to mean that component whose proportion in the mixture is the greater.
  • Preferred phosphorescent dopants for use in matrix systems, preferably mixed matrix systems, are the preferred phosphorescent dopants specified below. Dopants of the term phosphorescent are typical
  • a spin-forbidden transition for example a transition from an excited triplet state or a state with a higher spin quantum number, for example a quintet state.
  • Particularly suitable phosphorescent compounds are compounds which, with suitable excitation, emit light, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 , especially a metal with this atomic number.
  • phosphorescence emitter compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used, in particular compounds which contain iridium or platinum.
  • Examples of the emitters described above can be found in the applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005 / 0258742, WO 2009/146770, WO 2010/015307, WO
  • phosphorescent dopants examples include phosphorescent dopants.
  • the compound to be used according to the invention is used as a matrix material for a phosphorescent 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 the luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the mixture of the compound to be used according to the invention and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 80% by volume. -% of the compound according to the invention based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter based on the total mixture Emitter and matrix material.
  • the compound to be used according to the invention is used as the single matrix material (“single host”) for the phosphorescent emitter.
  • the organic electroluminescent device contains the compound to be used according to the invention, preferably a compound comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments listed above as matrix material, preferably as electron-conducting matrix material in one or more emitting layers, preferably in combination with a further matrix material, preferably a hole-conducting matrix material.
  • the further matrix material is an electron-transporting compound.
  • the further matrix material is a compound with a large band gap which does not participate, or does not participate to a significant extent, in the transport of holes and electrons in the layer.
  • An emitting layer comprises at least one emitting compound.
  • an organic electroluminescent device comprises the compound to be used according to the invention, preferably a compound comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4 ) or the preferred embodiments listed above in a hole transport layer or an electron transport layer.
  • the present invention therefore also relates to a composition containing at least one compound to be used according to the invention, preferably a compound comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below, as well as at least one further matrix material.
  • Suitable matrix materials which can be used in combination with the compounds according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or according to the preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. B.
  • CBP N, N-biscarbazolylbiphenyl
  • CBP N, N-biscarbazolylbiphenyl
  • indolocarbazole derivatives e.g. B. according to WO 2007/063754 or WO 2008/056746
  • indenocarbazole derivatives e.g. B. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776
  • azacarbazole derivatives e.g. B.
  • bipolar matrix materials e.g. B. according to WO 2007/137725
  • silanes e.g. B. according to WO 2005/111172
  • azaboroles or boronic esters e.g. B. according to WO 2006/117052
  • triazine derivatives e.g. B. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877
  • zinc complexes e.g. B.
  • diazasilol or tetraazasilol derivatives e.g. B. according to WO 2010/054729
  • diazaphosphole derivatives e.g. B. according to WO 2010/054730
  • bridged carbazole derivatives e.g. B. according to WO 2011/042107, WO 2011/060867, WO 2011/088877 and WO 2012/143080
  • triphenylene derivatives e.g. B. according to WO 2012/048781
  • dibenzofuran derivatives e.g. B.
  • WO 2015/169412 WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565 or biscarbazole, e.g. B. according to JP 3139321 B2, lactams, e.g. B. according to WO 2011/116865, WO 2011/137951 or WO 2013/064206, 4-spirocarbazole derivatives, e.g. B. according to WO 2014/094963 or WO 2015/192939.
  • a further phosphorescent emitter which emits with a shorter wave than the actual emitter, can also be present as a co-host in the mixture.
  • Preferred co-host materials are triazines, quinazolines, quinoxalines, triarylamine derivatives, in particular monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.
  • ⁇ can also be preferred to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material.
  • a mixture of a charge-transporting matrix material and an electrically inert matrix material which is not or not to a significant extent involved in charge transport, such as, for. B. described in WO 2010/108579.
  • compounds are particularly suitable as co-matrix material which have a large band gap and themselves do not, or at least not to a significant extent, participate in the charge transport of the emitting layer.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • triplet Emitter with the shorter-wave emission spectrum as a co-matrix for the triplet emitter with the longer-wave emission spectrum.
  • a compound to be used according to the invention comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) can particularly preferably be used in a preferred embodiment as matrix material in an emission layer of an organic electronic device, can be used in particular in an organic electroluminescent device, for example in an OLED or OLEC.
  • the matrix material containing the compound comprises structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below in the electronic device in combination with one or more dopants, preferably phosphorescent dopants, present.
  • the proportion of the matrix material in the emitting layer is in this case between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably between 92.0 and 99.5% by volume for fluorescent emitting layers and for phosphorescent emitting layers between 85.0 and 97.0% by volume.
  • the proportion of the dopant is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferably between 0.5 and 8.0% by volume for fluorescent emitting layers and between 3.0 and 15.0% by volume for phosphorescent emitting layers. -%.
  • An emitting layer of an organic electroluminescent device can also contain systems comprising a plurality of matrix materials (mixed matrix systems) and / or a plurality of dopants.
  • the dopants are generally those materials whose proportion in the system is the smaller and the matrix materials are those materials whose proportion in the system is the greater.
  • the proportion of an individual matrix material in the system can be smaller than the proportion of an individual dopant.
  • the compounds comprising structures according to formulas (I), (IIa) to (IIc) and / or (IIb-1) to (IIb-4) or the preferred embodiments set out above and below are used as one Component used by mixed matrix systems.
  • the mixed matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials.
  • one of the two materials is a material with hole-transporting properties and the other material is a material with electron-transporting properties.
  • the desired electron-transporting and hole-transporting properties of the mixed-matrix components can also be mainly or completely in a single mixed-matrix component be combined, the further or the further mixed matrix components fulfilling other functions.
  • the two different matrix materials can be present in a ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, particularly preferably 1:10 to 1: 1 and very particularly preferably 1: 4 to 1: 1.
  • Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. More detailed information on mixed matrix systems is contained, inter alia, in the application WO 2010/108579.
  • Another object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • Another object of the present invention is the use of a compound to be used according to the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as a fluorescent emitter, emitter which shows TADF (thermally activated delayed fluorescence), fluff material, electron transport material, electron injection material, Hole transport material, hole injection material, electron blocking material, hole blocking material and / or wide band gap material, preferably as a fluorescent emitter (singlet emitter), host material, hole transport material and / or electron transport material.
  • TADF thermalally activated delayed fluorescence
  • fluff material fluff material
  • electron transport material electron injection material
  • Hole transport material, hole injection material, electron blocking material, hole blocking material and / or wide band gap material preferably as a fluorescent emitter (singlet emitter), host material, hole transport material and / or electron transport material.
  • An electronic device in the sense of the present invention is a device which has anode, cathode and at least one intermediate layer
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLED, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O lasers), "organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLED,
  • the organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can also contain other layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. Interlayers, which for example have an exciton-blocking function, can also be introduced between two emitting layers. It should be noted, however, that it is not necessary for each of these layers to be present.
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers.
  • the organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs.
  • the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, d. H. 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. Furthermore, it is possible to use a metal complex, which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport or hole injection material, such as. B. described in WO 2009/030981.
  • the compound according to the invention can be used in different layers, depending on the precise structure.
  • An organic electroluminescent device containing a compound is preferred according to formula (I) or the preferred embodiment set out above in an emitting layer as a matrix material for phosphorescent emitters, for emitters which show TADF (thermally activated delayed fluorescence), in particular for fluorescent emitters or phosphorescent emitters.
  • the compound according to the invention can also be used in an electron transport layer and / or in a hole transport layer and / or in an exciton blocking layer and / or in a hole blocking layer.
  • the compound according to the invention is particularly preferably used as a matrix material for red, orange or yellow phosphorescent emitters, in particular for red phosphorescent emitters, in an emitting layer or as electron transport or hole blocking material in an electron transport or hole blocking layer.
  • the present invention also relates to an electronic device, preferably an organic electroluminescent device, which comprises one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more electron-conducting layers as the electron-conducting compound.
  • an electronic device preferably an organic electroluminescent device, which comprises one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more electron-conducting layers as the electron-conducting compound.
  • the device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since the service life of such devices is drastically shortened in the presence of water and / or air.
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with a sublimation process.
  • an initial pressure usually less than 10 -5 mbar, preferably less than 10 -6 mbar. It is also possible for the initial pressure to be even lower or even higher, for example less than 10 7 mbar.
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with 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.
  • OVPD Organic Vapor Phase Deposition
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and structured in this way (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers of solution, such as, for. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing) can be produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink-jet printing
  • Hybrid methods are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited.
  • organic electroluminescent devices containing the compounds according to the invention without any inventive step.
  • the electronic devices according to the invention in particular organic electroluminescent devices, are distinguished by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers to be used according to the invention, or the preferred embodiments set out above and below, in particular as emitters, preferably as fluorescent emitters, as electron-conducting materials and / or hole transport materials or as matrix materials a very good lifespan.
  • Electronic devices in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers to be used according to the invention, or the preferred embodiments set out above and below, in particular as emitters, preferably as fluorescent emitters, as electron transport materials, hole transport materials and / or as host materials, have a excellent efficiency. In particular, the efficiency is significantly higher compared to analogous compounds which do not contain a structure according to the invention.
  • the compounds, oligomers, polymers or dendrimers according to the invention or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices. In particular, these connections cause a low roll-off, i.e. a small drop in the power efficiency of the device at high luminance levels.
  • Electronic devices in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers or the preferred embodiments set out above and below as Emitters, preferably as fluorescent emitters, as electron transport materials, hole transport materials and / or as host materials, have very narrow emission bands with low FWHM values (Full Width Half Maximum) and lead to particularly pure color emission, recognizable by the small CIE-y - values.
  • the compounds, oligomers, polymers or dendrimers to be used according to the invention or the preferred embodiments set out above and below show a very high thermal and photochemical stability and lead to compounds with a very long service life.
  • optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by a high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants.
  • the compounds according to the invention When used in organic electroluminescent devices, the compounds according to the invention generally have very good properties. In particular, when the compounds according to the invention are used in organic electroluminescent devices, the service life is significantly better compared to similar compounds according to the prior art. The further properties of the organic electroluminescent device, in particular the efficiency and the voltage, are also better or at least comparable.
  • the following syntheses are carried out under a protective gas atmosphere in dried solvents.
  • the metal complexes are also handled with exclusion of light or under yellow light.
  • the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds which can have several enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative.
  • OLEDs according to 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 conditions described here (layer thickness variation, materials used).
  • the OLEDs basically have the following layer structure: substrate / hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / hole transport layer 1 (HTL1) consisting of HTM1, 170 nm for blue devices, 215 nm for green / yellow devices, 110 nm for red devices / hole transport layer 2 (HTL2) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL from ETM2) and finally a cathode .
  • the cathode is formed by a 100 nm thick aluminum layer.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is added to the matrix material or the matrix materials by co-evaporation in a certain volume proportion.
  • a specification like M1: M2: lr (L1) (55%: 35%: 10%) means that the material M1 in a volume fraction of 55%, M2 in one Volume fraction of 35% and I r (L 1) is present in a volume fraction of 10% in the layer.
  • the electron transport layer can also consist of a mixture of two materials.
  • Table 1 The exact structure of the OLEDs is shown in Table 1.
  • the materials used to produce the OLEDs are shown in Table 6.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in Im / W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance, calculated from the current-voltage-luminance- Characteristic curves (IUL characteristics), assuming a Lambertian radiation characteristic, and the service life is determined.
  • the electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and the CIE 1931 x and y color coordinates are calculated from this.
  • the compounds according to the invention can be used, inter alia, as electron-conducting host material eTMM in the emission layer EML of a phosphorescent OLED and as electron transport material in the HBL and the ETL.
  • eTMM electron-conducting host material
  • HBL emission layer
  • ETL electron transport material
  • the compounds according to the invention can be used, inter alia, as emitters (Dorand) in a fluorescent OLED.
  • the results of the OLEDs are summarized in Table 3.
  • Table 3 Structure of the OLEDs
  • the compounds according to the invention can also be processed from solution, where they lead to OLEDs which are considerably simpler in terms of process technology, compared to the vacuum-processed OLEDs, with nevertheless good properties.
  • the production of such components is based on the production of polymer light-emitting diodes (PLEDs), which has already been described many times in the literature (e.g. in WO 2004/037887).
  • the structure consists of substrate / ITO / hole injection layer (60 nm) / interlayer (20 nm) / emission layer (60 nm) / hole blocking layer (10 nm) /
  • Electron transport layer 40 nm/ cathode together.
  • substrates from Technoprint sinalime glass
  • ITO structure indium tin oxide, a transparent, conductive anode
  • the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by a UV / ozone plasma treatment.
  • a 20 nm hole injection layer PEDOT: PSS from Clevios TM
  • the required spin rate depends on the degree of dilution and the specific spin coater geometry.
  • the substrates are baked for 30 minutes at 200 ° C.
  • the interlayer used is used for hole transport, in which case HL-X from Merck is used.
  • the interlayer can also be replaced by one or more layers that only have to meet the condition not to be detached again by the downstream processing step of EML deposition from solution.
  • the triplet emitters according to the invention are dissolved together with the matrix materials in toluene or chlorobenzene.
  • the typical solids content of such solutions is between 16 and 25 g / L if, as here, the typical layer thickness of 60 nm for a device is to be achieved by means of spin coating.
  • the solution-processed devices contain an emission layer Ma: Mb: lr (w%: x%: z%) or Ma: Mb: Mc: lr (w%: x%: y%: z%), see table 3.
  • the emission layer is centrifuged in an inert gas atmosphere, in the present case argon, and baked at 160 ° C for 10 minutes.
  • the materials according to the invention lead to improved EQE (External Quantum Efficacy) in conjunction with reduced voltage and thus overall to improved power efficiency .

Abstract

La présente invention concerne l'utilisation de composés dans des dispositifs électroniques. L'invention concerne en outre de nouveaux composés, en particulier destinés à être utilisés dans des dispositifs électroniques, et des dispositifs électroniques comprenant ces composés.
PCT/EP2021/054773 2020-03-02 2021-02-26 Utilisation de composés sulfone dans un dispositif électronique organique WO2021175706A1 (fr)

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CN114409645A (zh) * 2021-12-28 2022-04-29 华南协同创新研究院 一种基于糖精衍生物的分子及其制备方法与应用

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CN114409645A (zh) * 2021-12-28 2022-04-29 华南协同创新研究院 一种基于糖精衍生物的分子及其制备方法与应用

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