EP3880657A1 - Zur herstellung einer organischen elektronischen vorrichtung einsetzbare verbindungen - Google Patents

Zur herstellung einer organischen elektronischen vorrichtung einsetzbare verbindungen

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Publication number
EP3880657A1
EP3880657A1 EP19805570.9A EP19805570A EP3880657A1 EP 3880657 A1 EP3880657 A1 EP 3880657A1 EP 19805570 A EP19805570 A EP 19805570A EP 3880657 A1 EP3880657 A1 EP 3880657A1
Authority
EP
European Patent Office
Prior art keywords
group
formula
atoms
radicals
aromatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19805570.9A
Other languages
German (de)
English (en)
French (fr)
Inventor
Philipp Stoessel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP3880657A1 publication Critical patent/EP3880657A1/de
Pending legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • 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
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    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/64—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings with a bridged ring system
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    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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    • H10K85/30—Coordination compounds
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • 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
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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    • 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
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    • Y02E10/549—Organic PV cells

Definitions

  • the present invention describes connections, particularly for use in electronic devices.
  • the invention further relates to a method for producing the connections according to the invention and electronic devices containing these connections.
  • OLEDs organic electroluminescent devices
  • Organometallic complexes which show phosphorescence are often used as emitting materials. For quantum mechanical reasons, using organometallic compounds as phosphorescence emitters, up to four times the energy and power efficiency is possible. In general, there is still a need for improvement with OLEDs, in particular also with OLEDs that show phosphorescence, for example with regard to efficiency, operating voltage and service life. Furthermore, organic electroluminescent devices are known which comprise phosphorescent emitters, fluorescent emitters or emitters which show TADF (thermally activated delayed fluorescence).
  • TADF thermalally 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. Improvements in these materials can lead to significant improvements in electroluminescence
  • the compounds should have a high color purity.
  • Another object of the present invention is to provide compounds which are suitable for use in an organic compound
  • Electroluminescent device as an emitter, preferably as
  • Phosphorescent emitters, fluorescent emitters or emitters are suitable which show TADF (thermally activated delayed fluorescence) and which lead to good device properties when used in this device, and the provision of the corresponding electronic device.
  • TADF thermalally activated delayed fluorescence
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic compound
  • Electroluminescent device which lead to good device properties when used in this device, and the provision of the corresponding electronic device.
  • Electron transport materials have a significant impact on the life and 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 OLED, in particular as a matrix material.
  • the compounds, in particular when they are used as matrix materials, as hole conductor materials or as electron transport materials in organic electroluminescent devices are also used as matrix materials.
  • the compounds should be as easy to process as possible, in particular show good solubility and film formation.
  • the compounds should show increased oxidation stability and an improved glass transition temperature.
  • the electronic devices should be able to be used or adapted for many purposes.
  • the performance of the electronic devices should be maintained over a wide temperature range.
  • Embodiments are therefore the subject of the present invention.
  • the present invention therefore relates to an organic functional connection which can be used to produce functional layers of electronic devices, which thereby
  • the compound comprises at least one structural element of the formula (I) and / or (la), the compound preferably has the formulas mentioned Formula (I) Formula (Ia) where the dashed bond represents the linkage of this group with a further part of the organically functional compound and the following also applies:
  • X is the same or different with each occurrence of CR or N with the
  • Ring atoms which can each be substituted by one or more radicals R 2 , or an aryloxy or fleteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2 , or an aralkyl or
  • Fleteroaralkyl group with 5 to 60 aromatic ring atoms which can be substituted with one or more radicals R 2 , or a combination of these systems; two or more, preferably adjacent radicals R 1 can form a ring system with one another; one or more radicals R 1 can form a ring system with a further part of the compound;
  • Ring atoms which can each be substituted by one or more R 3 radicals, or an aryloxy or fleteroaryloxy group having 5 to 40 aromatic ring atoms, which can be substituted by one or more R 3 radicals, or a combination thereof
  • Each occurrence of R 3 is selected identically or differently from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 C atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more F1 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 3 together form a ring system.
  • Compounds which can be used to produce functional layers of electronic devices are generally the organic or inorganic materials which are used, for example, in an organic electronic device, in particular in an organic one
  • Electroluminescent device are introduced between the anode and cathode, for example charge injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials. Organic materials are preferred.
  • connection which can be used to produce functional layers of electronic devices is a purely organic connection.
  • a purely organic compound is a compound that does not have a metal atom in it
  • Forms coordination compound still forms a covalent bond with a metal atom.
  • a purely organic compound preferably does not comprise a metal atom which is used in phosphorescence emitters. These metals, such as copper, molybdenum, etc.
  • connection used to create functional layers The connection used to create functional layers
  • phosphorescent emitters emitters that show TADF (thermally activated delayed fluorescence), host materials,
  • Electron transport materials exciton blocking materials
  • Electron injection materials hole conductor materials
  • Formula (II) Formula (Ila) wherein the dashed bond represents the linkage of this group with another part of the organically functional compound, the radicals R 1 have the meaning given above, in particular for formula (I) and / or (Ila), the Index v 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4 and especially is preferably 0 or 1 and the index u is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4 and particularly preferably 0 or 1.
  • adjacent carbon atoms are carbon atoms which are directly linked to one another. Furthermore, “neighboring residues” in the definition of the residues means that these
  • a fused aryl group, a fused aromatic ring system or a fused heteroaromatic ring system in the sense of the present invention is a group in which two or more
  • condensed, d. H. are fused, so that, for example, two carbon atoms belong to the at least two aromatic or heteroaromatic rings, such as in naphthalene.
  • fluorene is not a condensed aryl group in the sense of the present
  • Fleteroatoms may or may not contain.
  • an aryl group contains 6 to 60 C atoms, preferably 6 to 40 C atoms, particularly preferably 6 to 30 C atoms;
  • a fleteroaryl group in the sense of this invention contains 2 to 60 C atoms, preferably 2 to 40 C atoms, particularly preferably 2 to 30 C atoms and at least one fletero atom, with the proviso that the sum of C atoms and fleteroatoms is at least 5 results.
  • the fleteroatoms are preferably selected from N, O and / or S.
  • an aryl group or heteroaryl group either a simple aromatic cycle, ie 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 in the sense of this invention contains 6 to 60 C atoms, preferably 6 to 40 C atoms, particularly preferably 6 to 30 C atoms in the ring system.
  • a heteroaromatic ring system in the sense 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 hetero atom in the ring system, with the proviso that the sum of C atoms and
  • Heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as a system which does not necessarily only contain aryl or heteroaryl groups, but also in which 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 may be interrupted.
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.
  • aromatic ring systems in the sense of this invention, and also systems in which two or more aryl groups, for example, by one linear or cyclic alkyl group or interrupted by a silyl group.
  • systems in which two or more aryl or heteroaryl groups are bonded directly to one another such as, for.
  • biphenyl, terphenyl, quaterphenyl or bipyridine are also to be understood as an aromatic or heteroaromatic ring system.
  • a cyclic alkyl, alkoxy or thioalkoxy group in the sense of this invention means a monocyclic, a bicyclic or a polycyclic group.
  • Ci to C20 alkyl group in which also individual H atoms or CH2 groups by the groups mentioned above can be substituted, 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-hepty
  • An alkenyl group means, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
  • An alkynyl group means, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
  • Ci to C4o alkoxy group means, 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 in each case be substituted with the abovementioned radicals and which can be linked via any positions on the aromatic or heteroaromatic , are understood, for example, groups which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene,
  • compounds are preferred in which the structural element of the formula (I), (Ia), (II) and / or (Ila) of the organically functional compound has a high degree of symmetry, preferably based on the linking point (s) of this group is symmetrically substituted with another part of the organic functional compound.
  • Compound is selected from the group of fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles,
  • Spirocarbazoles pyrimidines, triazines, lactams, triarylamines,
  • the organically functional compound comprises a group which is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched
  • anthracenyl preferably 9-anthracenyl, trans- and cis-lindenofluorenyl, indenocarbazolyl, indolocarbazolyl, spirocarbazolyl, 5-aryl-phenanthridin-6-one-yl, 9,10-dehydrophenanthrenyl, fluoranthenyl, tolyl, mesity , Phenoxytolulyl, anisolyl, triarylaminyl, bis-triarylaminyl, tris-triarylaminyl, flexamethylindanyl, tetralinyl, monocycloalkyl, biscycloalkyl, tricycloalkyl, alkyl, such as, for example tert-butyl, methyl, propyl, alkoxyl,
  • Structural element A a comprises a corresponding group or can be represented by a corresponding group.
  • substituents R and / or R 1 selected from the group consisting of H, D, F, CN, N (Ar) 2, N (Ar 1 ) 2, a straight-chain alkyl group having 1 to 8 C atoms are particularly preferred 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 1 , 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 preferred with 6 to 13 aromatic ring atoms, each of which can be substituted with one or more non-aromatic radicals R 1 or R 2 , but is preferably unsubstituted; optionally two substituents R 1
  • the substituents R are particularly preferably selected from the group consisting of F1 or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, which are each substituted with one or more non-aromatic radicals R 1 can, but preferably
  • R is unsubstituted.
  • suitable 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, 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.
  • the substituents R 1 are very particularly preferably selected from the group consisting of an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, which can each be substituted with one or more non-aromatic radicals R 2 , but preferred
  • R 1 is unsubstituted.
  • suitable substituents R 1 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, 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 and / or R 1 of the bullvalene structure according to the formulas (I), (Ia), (II) and / or (Ila) do not form a condensed aromatic or heteroaromatic ring system with one another, preferably not a condensed ring system. This includes the formation of a condensed ring system with possible substituents R 1 , R 2 , R 3 , which can be bound to the radicals R 1 or R 2 .
  • the organically functional compound comprise at least one group which comprises at least one of the formulas (lilac), (llll), (Ille), (llld), (Ille), (Ulf), (lllg) and / or (lllh) corresponds to Formula (Ille)
  • X is the same or different at each occurrence N or CR
  • Groups X in a cycle are N;
  • m is independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, with the proviso that the sum of the indices m per ring is at most 4, preferably at most 2;
  • o is independently 0, 1 or 2, preferably 0 or 1, with each occurrence, with the proviso that the sum of the indices o per ring is at most 2, preferably at most 1;
  • a a is a functional structural element, preferably has an aromatic or heteroaromatic ring system each having 5 to 40 ring atoms, which can be substituted by one or more substituents R;
  • a b comprises, preferably a structure of the formula (I) or (Ia) and / or a structure of the formula (II) or (I Ia), the symbol R being the same as above, especially for the formula (I) or (Ia) meaning mentioned, with the proviso that the
  • the sum of the groups A a and / or A b is preferably 1 to 10, particularly preferably 1 to 5 and is particularly preferably 1, 2, 3 or 4.
  • the sum of the indices m, o and u in the structures of the formulas (purple) to (IIIh) and (IVa) to (IVh) is in each case at most 6, preferably at most 4 and particularly preferably at most 2.
  • the functional structural element A a in the structures of the formulas (purple) to (IIIh) and (IVa) to (IVh) has at least one aromatic or heteroaromatic ring system, each with 5 to 40 Has ring atoms, which can be substituted with one or more substituents R 1 .
  • the functional structural element A a in the structures of the formulas (lilac) to (IIIh) and (IVa) to (IVh) is preferably selected from the group of the fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, Lactams,
  • Triarylamines dibenzofurans, dibenzothiophenes, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzothiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, fluoradenes.
  • the functional structural element A a is selected from hole transport groups, electron transport groups, host material groups or wide-band gap groups. These groups are known as such and are described below.
  • connection which can be used for the production of functional layers of electronic devices comprises a hole transport group, these being preferably triarylamine or carbazole groups.
  • the hole transport group is linked to at least one bullvalene structure via one or two linkages, which is represented as a broken line in formulas (I) or (Ia).
  • At least one of the groups R and / or R 1 in a structure according to the formulas (I), (la), (II), (lla) (lilac) to (lllh) and / or (IVa) to (IVh) , (IVc) (V) comprises a hole transport group, preferably represents.
  • the hole transport group comprises a group, preferably stands for 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 C atoms or a heteroaromatic ring system with 3 to 40 C atoms, which can each be substituted by one or more radicals R 1 ; p is 0 or 1;
  • the presence of an NN bond is preferably excluded.
  • the hole transport group comprises a group, preferably stands for a group which is selected from the formulas (H-4) to (H-26),
  • Formula (H-20) Formula (H-21) where Y 1 is O, S, C (R 1 ) 2, NR 1 or NAr 1 , the dashed bond marks the attachment position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is the same or different with each occurrence is 0, 1, 2, 3 or 4, p is 0 or 1,
  • Ar 1 and R 1 the above, in particular for formula (I) or (la) and Ar 2 the above, in particular for formula (H-1), (H-2) or (H-3)
  • Ar 2 represents 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 preferably unsubstituted where R 1 can have the meaning given above, in particular for formula (I).
  • Ar 2 particularly preferably represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic
  • 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 for formula (I).
  • Ar 2 which is set forth in formulas (H-1) to (H-26), furthermore preferably represents an aryl or fleteroaryl 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 bound 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 rings, preferably not a condensed aromatic or heteroaromatic ring system with condensed 6 - Rings includes. Accordingly,
  • Naphthyl structures preferred over anthracene structures.
  • Farther 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 in formulas (H-1) to (H-26), inter alia, has at most 1 nitrogen atom, preferably at most 2 fleteroatoms, particularly preferably at most one
  • Fleteroatom and particularly preferably has no fleteroatom.
  • Ar 3 and / or Ar 4 are the same or different for each occurrence
  • aromatic or heteroaromatic ring system with 6 to 24
  • aromatic ring atoms preferably with 6 to 18 aromatic
  • Ring atoms particularly preferably for an aromatic ring system with 6 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 is the same as above, can have in particular the meaning shown in formula (I) or (Ia).
  • connection which can be used for providing functional layers of electronic devices, comprises a remainder comprising an electron transport group.
  • Links which is represented in formulas (I) or (la) as a dashed link, is linked to at least one bullvalene structure.
  • At least one of the groups R and / or R 1 in a structure according to the formulas (I), (la), (II), (lla) (lilac) to (lllh) and / or (IVa) to (IVh) preferably comprises a radical comprising an electron transport group.
  • Electron transport groups are well known in the art and promote the ability of compounds to transport and / or conduct electrons.
  • Functional layers of electronic devices can be used, surprising advantages which include at least one structure selected from the group pyridines, pyrimidines, pyrazines, pyridazines, triazines,
  • Quinazolines, quinoxalines, quinolines, isoquinolines, imidazoles and / or benzimidazoles is selected, with pyrimidines, triazines and quinazolines being particularly preferred. These structures generally promote the ability of compounds to transport and / or conduct electrons.
  • the radical comprising the electron transport group 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 , Q is an electron transport group, wherein R 1 is the same as 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 respectively
  • heteroaromatic systems are formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings.
  • a further link between the above-mentioned conjugated groups, for example via an S, N or O atom or a carbonyl group, does not harm a conjugation.
  • the two aromatic rings are bonded directly, although the sp 3 hybridized carbon atom in position 9 is one
  • L 1 represents a bond or an aromatic or heteroaromatic
  • Ring atoms preferably an aromatic ring system with 6 to 12 carbon atoms, which by one or more radicals R 1
  • L 1 particularly preferably represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, which can in each case be substituted by one or more radicals R 2 , but is preferably unsubstituted, where R 2 is the same as above, can have in particular the meaning given for formula (I).
  • L 1 which is set out, inter alia, in formula (QL), preferably identically or differently, represents a bond or an aryl or fleteroaryl radical having 5 to 24 ring atoms on each occurrence,
  • Ring atoms so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is direct, i.e. via an atom of the aromatic or heteroaromatic group to which the atom of the further group is bound.
  • the group L 1 set out in formula (QL) comprises an aromatic ring system with at most two condensed aromatic and / or heteroaromatic 6-rings, preferably no condensed aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are also 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, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, Spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, each with a or more radicals R 1 can be substituted, but are preferably unsubstituted.
  • the group L 1 which is set forth in formula (QL), has at most 1 nitrogen atom, preferably at most 2 fletero atoms, particularly preferably at most one fletero atom and particularly preferably no fletero atom.
  • 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-1), (Q-2), (Q-4), (Q-4), (Q- 5), (Q-6), (Q-7), (Q-8), (Q-9) and / or (Q-10)
  • Q represents NR 1 , O or S
  • R 1 is as previously defined, in particular in formula (I) or (Ia).
  • the substituents R 1 in the structures of the formulas (Q-1) to (Q-10) are in structures according to formulas (II), (IIa) and (IVa) to (IVh)
  • the group Q or the electron transport group set out, inter alia, in the formula (QL) can preferably be selected from a structure of the formulas (Q-11), (Q-12), (Q-13), (Q-14) and / or (Q-15)
  • Electron transport group can be selected from structures of the formulas (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22)
  • Electron transport group can be selected from structures of the formulas (Q-23), (Q-24) and / or (Q-25),
  • Electron transport group can be selected from structures of the formulas (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30), where symbols Ar 1 and R 1 have the meaning previously given, inter alia, for formula (I) or (Ia), X 'is N or CR 1 and the dashed bond marks the attachment position.
  • X ' is N or CR 1 and the dashed bond marks the attachment position.
  • X ' represents a nitrogen atom.
  • the group Q set out in the formula (QL) or the electron transport group can preferably be selected be 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) wherein the symbols Ar 1 and R 1 have the meaning set forth above for formula (I) or (la), the dashed bond
  • the substituents R 1 in the structures of the formulas (Q-11) to (Q-44) are in structures of the formulas (II), (IIa) and (IVa) to (IVh)
  • Ar 1 is the same or different in each occurrence for an aromatic or heteroaromatic ring system, preferably an aryl or
  • Fleteroaryl radical with 5 to 24 aromatic ring atoms preferably with 6 to 18 aromatic ring atoms, particularly preferably for an aromatic ring system, preferably an aryl radical with 6 to 12 aromatic ring atoms or a heteroaromatic ring system, preferably a fleteroaryl group with 5 to 13 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 , but is preferably unsubstituted, where R 2 can have the meaning given above, in particular in formula (I).
  • Ar 1 preferably represents an aryl or fleteroaryl radical, so that an aromatic or heteroaromatic group
  • aromatic or heteroaromatic ring system directly, i.e. via an atom of the aromatic or heteroaromatic group to which the respective atom of the further group is bound, for example a C or N atom from the groups (H-1) to (H-26) or (Q-26) to ( Q-44).
  • 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, in particular 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, imimdazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, indenocarbazolyl, 1- or 2-naphthyl, anthracenyl,
  • the organically functional connection comprises at least one group that leads to materials with wide band gap.
  • group that leads to wide-band gap materials means that the connections can be used as wide-band gap materials, so that the connections have corresponding groups. Wide band gap materials will be discussed in more detail later.
  • the organically functional compound comprises at least one group which leads to materials which are used as
  • Host material can be used.
  • group leading to materials used as host material means that the
  • Compounds can be used as host materials, so that the compounds have corresponding groups. Host materials will be discussed in more detail later. In a further embodiment it can be provided that the
  • Compound which can be used for the production of functional layers of electronic devices comprises a fused aromatic or heteroaromatic ring system with at least 2, preferably three fused rings, which may optionally be substituted.
  • connection which can be used for the production of functional layers of electronic devices, comprises at least one aromatic or heteroaromatic ring system with at least two, preferably with three condensed aromatic or heteroaromatic rings.
  • aromatic or heteroaromatic ring system with at least two, preferably with three condensed aromatic or
  • heteroaromatic rings is linked to at least one bullvalene structure via one or two linkages, which is represented, for example, in formulas (I) or (la) as a dashed bond.
  • At least one of the groups R and / or R 1 in a structure according to the formulas (I), (la), (II), (lla) (lilac) to (lllh) and / or (IVa) to (IVh) comprises at least one aromatic or heteroaromatic ring system with at least two, preferably with three condensed aromatic or heteroaromatic rings, preferably represents.
  • heteroaromatic ring system with two, preferably with three
  • condensed aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar-1) to (Ar-11)
  • the structural element of the formula (Ia) or (I Ia) is condensed onto an aromatic or heteroaromatic ring system with 5 to 60 carbon atoms, which is selected from the groups of the formulas (Ar-12) to (Ar-58 )
  • X ' is N or CR 1 , preferably CR 1
  • Y' is selected from O, S, C (R 1 ) 2 , Si (R 1 ) 2, Ge (R 1 ) 2 , NR 1 or NAr 1 , preferred O, S, NAr 1 , particularly preferably NAr 1
  • Structures of the formulas (Ar-2) to (Ar-54) are preferred and structures of the formulas (
  • the double bond shown in the structures according to formulas (la) or (lla), which is marked with the dashed bond, can be regarded as part of the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms to which the
  • Structural element according to formula (la) or (lla) is condensed.
  • At least one, particularly preferably at least two of the groups X 'per ring are selected from C-Fl and C-D.
  • compounds having partial structures of the formulas (Ar-1) to (Ar-58) are preferred in which no more than four, preferably no more than two, groups X 'represent N, and particularly preferably all groups X' represent CR 1 , preferably at most four, particularly preferably at most three and particularly preferably at most two of the groups CR 1 for which X 'is not equal to the group CH.
  • aromatic or heteroaromatic ring system with two, preferably with three condensed aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar'-1) to (Ar'-11)
  • L 1 is a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 , where R 1 has the meaning given above, in particular for formula (I) or (Ia), 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 0, 1, 2 or 3, preferably 0.1 or 2, particularly preferably 0 or 1 at each occurrence;
  • h is independently 0, 1, 2, 3 or 4, preferably 0.1 or 2, particularly preferably 0 or 1 with each occurrence;
  • i is independent on each occurrence 0, 1 or 2;
  • n is an integer in the range from 0 to 7, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2.
  • the sum of the indices p, e, i, j, h and m in the structures of the formulas (Ar'-1) to (Ar'-11) is preferably at most 3,
  • the structural element of the formula (Ia) or (Ila) is condensed to an aromatic or heteroaromatic ring system with 5 to 60 carbon atoms, which is selected from the groups of the formulas (Ar'-12) to (Ar'- 57 where R 1 is the one mentioned above, in particular for formula (I) or (Ia)
  • the index o is 0, 1 or 2, preferably 0 or 1, the index n 0, 1, 2, or 3,
  • aromatic or heteroaromatic ring system with 5 to 60
  • Carbon flavors bind to form a ring.
  • Structures of the formulas (Ar'-2) to (Ar'-53) are preferred and structures of the formulas (Ar'-4) to (Ar'-15) and (Ar'-22) to (Ar'-43) are particularly preferred .
  • the sum of the indices o, n, m and I is at most 6, preferably at most 4 and particularly preferably at most 2.
  • the structures of the formulas (Ar-1) to (Ar-158) and / or (Ar'-1) to (Ar'-57) can preferably be hole transport groups
  • Residues comprising electron transport groups, preferably
  • radicals comprising electron transport groups according to formula (QL), the electron transport group preferably being represented by formulas (Q-1) to (Q-44).
  • the substituents R 1 in the structures of the formulas (H-1) to (H-26) and / or (Q-1) to (Q-44) are to be replaced by substituents R 2 .
  • the organically functional compound comprises at least one solubility-imparting group.
  • a solubility-imparting group or a solubility-imparting structural element can preferably preferably comprise a longer alkyl group (approx. 4 to 20 carbon atoms), in particular a branched alkyl group, or an optionally substituted aryl group.
  • the preferred aryl groups include a xylyl, mesityl, terphenyl or quaterphenyl group, with branched ones
  • Terphenyl or quaterphenyl groups are particularly preferred.
  • the compound contains at least one solubility-imparting structural element or a solubility-imparting group and contains at least one functional structural element or a functional group, the functional structural element or the functional group is selected from hole transport groups,
  • Electron transport groups, structural elements or groups, which lead to host materials or structural elements or groups with wide-band gap properties are provided.
  • substituents R 1 are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar 1 ) 2, a straight-chain alkyl group having 1 to 8 C atoms, preferably having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 8 C atoms, preferably with 3 or 4 C atoms, or an alkenyl group with 2 to 8 C atoms, preferably with 2, 3 or 4 C atoms, the can each 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 with 6 to 13 aromatic ring atoms, which can each be substituted with one or more non-aromatic radicals R 1 , but is preferably unsubstituted; optionally two substituents R 1 , preferably those on adjacent ones
  • Carbon atoms are bonded, form a monocyclic or polycyclic, aliphatic ring system which can be substituted with one or more radicals R 2 , but is preferably unsubstituted, where Ar 1 can have the meaning set out above.
  • 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 with one or more non-aromatic radicals R 2 may be substituted, but is preferably unsubstituted.
  • substituents R 1 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, 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.
  • Ring atoms of the aromatic or heteroaromatic ring system do not form a condensed aromatic or heteroaromatic ring system, preferably do not form a condensed ring system. This includes the formation of a condensed ring system with possible substituents R 2 , R 3 , which can be bound to the radicals R 1 .
  • Compound comprises at least one group, preferably in the structure according to formula (lilac) to (IIIh) and / or (IVa) to (IVh) at least one structural element A a or at least one radical Ar 1 , Ar 2 , Ar 3 , Ar 4 and / or R 1 comprises a group, preferably represents a group which is selected from the formulas (R 1 -1) to (R 1 - 92)
  • Y 1 is O, S or NR 2 , preferably O or S;
  • k is independently 0 or 1 at each occurrence
  • i is independent on each occurrence 0, 1 or 2;
  • j is independently 0, 1, 2 or 3 at each occurrence
  • h is independently 0, 1, 2, 3 or 4 at each occurrence
  • g is independently 0, 1, 2, 3, 4 or 5 at each occurrence
  • R 2 can have the meaning given above, in particular for formula (I) or (Ia), and
  • the dashed binding marks the binding position.
  • the groups of the formulas R 1 -1 to R 1 -54 are preferred, the groups R 1 -1, R 1 -3, R 1 -5, R 1 -6, R 1 -15, R 1 -29, R 1 -30, R 1 -31, R 1 -32, R 1 -33, R 1 -38, R 1 -39, R 1 -40, R 1 -41, R 1 -42, R 1 -43, R 1 -44 and / or R 1 -45 particularly preferred.
  • the sum of the indices k, i, j, h and g in the structures of the formulas (R 1 -1) to (R 1 -92) is 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 -92) with the ring atoms of the aryl group or fleteroaryl group to which the radicals R 2 are bonded do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system .
  • radicals of the formulas (R 1 -1) to (R 1 -92) described 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 this
  • Formulas in which case the groups R 2 set out in formulas (R 1 -1) to (R 1 -92) are to be replaced by R 1 radicals.
  • the preferences set out above with regard to formulas (R 1 -1) to (R 1 -92) apply accordingly.
  • the compound comprise at least one connecting group which is selected from the formulas (L 1 -1) to (L 1 -108), 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 -108) or the electron-conducting group with further structural elements via a
  • connecting group which is selected from the formulas (L 1 -1) to (L 1 -108) or the rest L 1 in formulas (QL), (Ar-1) to (Ar-1 1) and / or (Ar'-1) to (Ar'-1 1) stands for a group which is selected from the formulas (L 1 -1) to (L 1 -108),
  • the index k is 0 or 1
  • the index I is 0, 1 or 2
  • the index j is independently 0, 1, 2 or 3 each time it occurs
  • the index h in each Occurrence is independently 0, 1, 2, 3 or 4
  • the index g is 0, 1, 2, 3, 4 or 5
  • the symbol Y 2 is O, S or NR 1 , preferably O or S
  • the symbol R 1 has the meaning given above, in particular for formula (I) or (la).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -108) is in each case at most 3, preferably at most 2 and particularly preferably at most 1 .
  • Preferred compounds according to the invention with a group of the formulas (H-1) to (H-26) comprise a group Ar 2 which is selected from one of the formulas (L 1 -1) to (L 1 -78) and / or (L 1 -92) to (L 1 -108), preferably of the formula (L 1 -1) to (L 1 -54) and / or (L 1 -92) to (L 1 -108), particularly preferably of the formula ( L 1 -1) to (L 1 -29) and / or (L 1 -92) to (L 1 - 103).
  • the sum of the indices k, I, g, h and j can advantageously be in the
  • Preferred compounds according to the invention having a group of the formula (QL) comprise a group L 1 which is a bond or which is selected from one of the formulas (L 1 -1) to (L 1 -78) and / or (L 1 -92 ) to (L 1 -108), preferably of the formula (L 1 -1) to (L 1 -54) and / or (L 1 -92) to (L 1 - 108), particularly preferably of the formula (L 1 - 1) to (L 1 -29) and / or (L 1 -92) to (L 1 -103).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -78) and / or (L 1 -92) to (L 1 -108) can advantageously be , preferably of the formula (L 1 -1) to (L 1 -54) and / or (L 1 -92) to (L 1 -108), particularly preferably of the formula (L 1 -1) to (L 1 -29) ) and / or (L 1 -92) to (L 1 - 103) in each case at most 3, preferably at most 2 and particularly preferably at most 1.
  • Preferred compounds according to the invention having a group of the formulas (Ar-1) to (Ar-1 1) and / or (Ar'-1) to (Ar'-1 1) comprise a group L 1 which is a bond or which is selected is from one of the Formulas (L 1 -1) to (L 1 -78) and / or (L 1 -92) to (L 1 -108), preferably of the formula (L 1 -1) to (L 1 -54) and / or (L 1 -92) to (L 1 -108), particularly preferably of the formula (L 1 -1) to (L 1 -29) and / or (L 1 -92) to (L 1 -103).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -78) and / or (L 1 -92) to (L 1 -108) can advantageously be , preferably of the formula (L 1 -1) to (L 1 -54) and / or (L 1 -92) to (L 1 -108), particularly preferably of the formula (L 1 -1) to (L 1 -29) ) and / or (L 1 -92) to (L 1 -103) in each case at most 3, preferably at most 2 and particularly preferably at most 1.
  • radicals R 2 in the formulas (L 1 -1) to (L 1 -108) with the ring atoms of the aryl group or fleteroaryl group to which the radicals R 2 are bonded do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system .
  • electronic devices can be used, selected from the group of phenyls, fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, lactams, triarylamines, dibenzofurans, dibenzothienes, imidazoles,
  • Benzimidazoles benzoxazoles, benzothiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, fluoradenes.
  • Functional layers of electronic devices can be used, preferably compounds comprising structures according to the formulas (I), (la), (II), (lla), (lilac) to (lllh) and / or (IVa) to (IVh), 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, particularly preferably less than or equal to 2000 g / mol and very particularly preferably less than or equal to 1200 g / mol.
  • 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, particularly preferably less than or equal to 2000 g / mol and very particularly preferably less than or equal to 1200 g / mol.
  • compounds according to the invention are defined by structures according to the formulas (purple) to (IIIh) and / or (IVa) to (IVh). Furthermore, preferred compounds according to the invention are distinguished in that they can be sublimed. These compounds generally have a molecular weight of less than approximately 1200 g / mol. If the compound according to the invention is substituted with aromatic or heteroaromatic groups R 1 or R 2 , it is preferred if these have no aryl or heteroaryl groups with more than two aromatic six-membered rings which are directly condensed 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 more so with the low triplet energy
  • Condensed aryl groups with more than two aromatic six-membered rings 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 by groups R 1 or R 2 or by appropriate substitution of the groups (R 1 -1) to (R 1 -92), preferably (R 1 -33) to (R 1 -57) and (R 1 - 76) to (R 1 -86), or (L 1 -1) to (L 1 -109), preferably (L 1 -30) to (L 1 -60) and (L 1 -71) to (L 1 -91), with the groups R 1 or R 2 or by appropriate substitution of the groups (R 1 -1) to (R 1 -92), preferably (R 1 -33) to (R 1 -57) and (R 1 - 76) to (R 1 -86), or (L 1 -1) to (L 1 -109), preferably (L 1 -30) to (L 1 -60) and (L 1 -71) to (L 1 -91), with the groups R 1 or
  • R 2 for example in the case of a structure of the formula (I) and preferred embodiments of this structure or the structures in which reference is made to these formulas, is the same or different selected from the group consisting of each occurrence H, D, an aliphatic hydrocarbon radical with 1 to 10 C atoms, preferably with 1, 2, 3 or 4 C 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, through one or more
  • Alkyl groups each having 1 to 4 carbon atoms can be substituted, but is preferably unsubstituted.
  • the radicals R 2 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 2 are bonded. This includes the formation of a condensed ring system with possible substituents R 3 , which may be attached to the radicals R 2 .
  • R 3 for example in the case of a structure of the formulas (I), (Ia), (II), (Ila), (III) to (IIIh), (IVa) to (IVh), is preferred Embodiments of this structure or the structures in which reference is made to these formulas, each occurrence, identically or differently selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 10 carbon atoms, preferably having 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, each of which has one or more alkyl groups 1 to 4 carbon atoms can be substituted, but is preferably unsubstituted.
  • the group consisting of H, D, F, CN an aliphatic hydrocarbon radical having 1 to 10 carbon atoms, preferably having 1 , 2, 3 or 4 carbon atoms
  • the combinations of the partial structure of the formula II include
  • Residues comprising electron transport groups are preferred according to the following table
  • Production of functional layers of electronic devices can be used, a ligand in a metal complex.
  • Metal complexes have unexpected technical advantages.
  • Another object of the present invention is therefore a metal complex comprising one or more structural elements of the formula (I) and / or (Ia) or preferred embodiments thereof
  • the present invention accordingly furthermore relates to a metal complex comprising at least one structure of the general formula (1) M (L) n (L ') m Formula (1) where applies to the symbols and indices used
  • M is a transition metal, preferably copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum,
  • Silver, gold or europium particularly preferably iridium or platinum;
  • L is the same or different at each occurrence a bidentate ligand; L ’is the same or different each time a ligand occurs; n is 1, 2 or 3, preferably 2 or 3, particularly preferably 2; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1, particularly preferably 0; several ligands L can also be linked to one another or L to L 'via a single bond or a bivalent or trivalent bridge and thus span a tridentate, tetradentate, pentadentate or hexadentate ligand system, characterized in that the metal complex has at least one partial structure of the formula ( 2) and / or (2a) contains:
  • Formula (2) wherein the dashed bond represents the linkage of this group with a further part of the metal complex of formula (1) and the symbol X has the meaning set out above for formula (I) or (Ia). It can further be provided that the metal complex contains at least one partial structure of the formula (2-1) and / or (2a-1):
  • Symbols u, v and R 1 have the meanings previously given, inter alia, for formulas (I), (la), (II) or (lla).
  • the linkage of the substructure according to formula (2), (2a) (2-1) or (represented by a dashed bond in formula (2), (2a) (2-1) or (2a-1) is 2a-1) with one
  • aromatic or heteroaromatic ring system preferably an aryl or fleteroaryl radical with preferably 5 to 40 ring atoms
  • Ring system preferably the aryl or fleteroaryl radical having 5 to 40 ring atoms, preferably 5 to 24 with ring atoms and particularly preferably 6 to 12 with ring atoms with one or more radicals R, as previously defined for formula (2); however, this residue is preferably unsubstituted.
  • the aromatic or heteroaromatic ring system or the aryl or fleteroaryl radical is preferably part of a ligand L and coordinates directly to the metal M.
  • (2a), (2-1) and / or (2a-1) is directly connected to the metal atom M. This can preferably be done via one of the radicals R or R 1 .
  • the metal complexes of the formula (1) according to the invention can have one or two ; three or more of the partial structures of the formula (2) set out in more detail above (2a) or their preferred embodiments.
  • a metal complex of the formula (1) according to the invention can comprise exactly one partial structure of the formula (2) or (2a).
  • Metal complexes of the formula (1) can preferably contain two, particularly preferably three or more of the partial structures of the formula (2) and / or (2a) set out above or their preferred embodiments.
  • the invention comprises
  • Metal complexes of the formula (1) one, two, three or six partial structures of the formula (2) and / or (2a) or their preferred embodiments.
  • Metal complexes can preferably have one, two or three bidentates
  • the coordinating atoms of the bidentate ligands can be selected identically or differently at each occurrence from C, N, P, O, S and / or B, particularly preferably C, N and / or O and very particularly preferably C and / or N.
  • the bidentate ligands preferably have one carbon atom and one nitrogen atom or two carbon atoms or two nitrogen atoms or two oxygen atoms or one oxygen atom and one nitrogen atom as coordinating atoms.
  • the coordinating atoms of each of the ligands can be the same or they can be different. At least one, particularly preferably all, of the bidentate ligands preferably has one carbon atom and one nitrogen atom or two carbon atoms as coordinating atoms, in particular one
  • the bidentate ligands and very particularly preferably for M Ir all three bidentate ligands have a carbon atom and a nitrogen atom or two carbon atoms as coordinating atoms, in particular a carbon atom and a nitrogen atom. It is thus particularly preferably an iridium complex in which all three bidentate ligands are ortho-metallated, ie form a metallacycle with the iridium in which there is at least one iridium-carbon bond.
  • the metal complex particularly preferably does not comprise any monodentate ligands and all bidentate ligands, identically or differently, have at least one carbon atom as coordinating atom on each occurrence.
  • the bidentate ligands can be linked to one another and can have further coordination points, so that the term “bidentate ligand” denotes a ligand which has at least two coordination points. If a bidentate ligand has exactly two coordination points, this is explicitly stated.
  • the index n in formula (1) can be 1 and the index m can be 0 at the same time, in which case, for example, the bidentate ligands L are linked to one another and span a hexadentate ligand system.
  • the three ligands linked to one another can also be regarded as partial ligands.
  • indices in the formula (1) set out above or the preferred embodiments of this formula depend on the type of metal and a possible linkage of the ligands.
  • a metal complex containing iridium and a hexadentate tripodal ligand or a metal complex containing platinum and a tetradentate ligand being particularly preferably formed.
  • the metal complex according to formula (1) preferably comprises three bidentate ligands L, which can optionally also be linked.
  • the three bidentate ligands can be the same or different. If the bidentate ligands are the same, they are preferably also the same
  • C3-symmetric iridium complexes are formed in polypodal complexes. It can also be advantageous to choose the three bidentate ligands differently or to select two ligands the same and the third ligand differently, so that Ci-symmetrical metal complexes arise because this allows greater variation possibilities of the ligands, so that the desired properties of the Complex things such as the location of HOMO and LUMO or the emission color can be varied more easily.
  • the solubility of the complexes can also be improved without having to add long aliphatic or aromatic solubilizing groups.
  • the three bidentate ligands are either chosen identically or two of the bidentate ligands are chosen identically and the third bidentate ligand is different from the first two bidentate ligands.
  • the metal complex has three bidentate ligands, all three ligands being selected identically or two of the bidentate ligands being selected identically and the third bidentate ligand being different from the first two bidentate ligands.
  • the metal is Ir (III) and the
  • Metal complex has three bidentate ligands, two of the bidentate ligands to the iridium via a carbon atom and a
  • Coordinate nitrogen atom and the third of the bidentate ligands coordinates to the iridium via one carbon atom and one nitrogen atom or via two carbon atoms or via two nitrogen atoms, preferably the third of the bidentate ligands coordinates to the iridium via one carbon atom and one nitrogen atom or via two carbon atoms.
  • the metal is Pt, which is coordinated to two bidentate ligands.
  • the metallacycle which is spanned from the metal and the bidentate ligand is a five-membered ring, which is particularly preferred when the coordinating the atoms are C and N, C and C, N and N or N and O. If the coordinating atoms are O, one can also
  • Metallasechring be preferred. This is shown schematically below:
  • N is a coordinating nitrogen atom
  • C is a coordinating carbon atom
  • O is coordinating oxygen atoms and the carbon atoms shown are atoms of the bidentate ligand.
  • At least one of the bidentate ligands are selected identically or differently on each occurrence the structures of the following formulas (L-1), (L-2), (L-3), (L-4) and / or (L-5)
  • CyC is identical or different with each occurrence a substituted or unsubstituted aryl or fleteroaryl group with 5 to 14 aromatic ring atoms, each of which coordinates to the metal via a carbon atom and which is in each case connected to CyD via a covalent bond;
  • CyD is the same or different with each occurrence a substituted or unsubstituted fleteroaryl group with 5 to 14 aromatic ring atoms, which coordinates to the metal via a nitrogen atom or via a carbene carbon atom and which is linked to CyC via a covalent bond;
  • CyE is a substructure the same or different with each occurrence
  • ligands L can also be linked to one another or L to L 'via a single bond or a bivalent or trivalent bridge and thus span a tridentates, tetradentates, pentadentates or hexadentates ligand system, these optional bonds to a bridge being indicated by the dashed bond is;
  • several of the optional substituents can form a ring system with one another; a substituent can also coordinate to M; furthermore, the optional radicals are preferably selected from the radicals R mentioned above and / or the partial structure of the formula (2) and / or (2a).
  • CyD coordinates in the ligands of the formulas (L-1) and (L-2) preferably via a neutral nitrogen atom or via a carbene carbon atom.
  • one of the two groups CyD in the ligand of the formula (L-3) preferably coordinates via a neutral nitrogen atom and the other of the two groups CyD via an anionic nitrogen atom.
  • CyC also preferably coordinates in the ligands of the formulas (L-1) and (L-2) via anionic carbon atoms.
  • CyC is an aryl or heteroaryl group with 6 to 13 aromatic ring atoms, particularly preferably with 6 to 10 aromatic ring atoms, very particularly preferably with 6 aromatic ring atoms, which coordinates to the metal via a carbon atom which can be substituted by one or more radicals R and which is linked to CyD via a covalent bond.
  • CyC group are the structures of the following formulas (CyC-1) to (CyC-20), where CyC binds to CyD at the position marked with # and coordinates to the metal at the position marked with *, R has the meaning given above, in particular for formula (I) or (la), and applies to the other symbols used: X is the same or different at each occurrence CR or N, with preferably a maximum of two symbols X per cycle representing N;
  • W is NR, O or S; the ligands can optionally be connected by a bridge via the group CyC, the binding to the bridge preferably being able to take place via the position marked with “o”, the position marked with “o” representing a carbon atom if this is one
  • a maximum of two symbols X in CyC preferably stand for N, particularly preferably a maximum of one symbol X in CyC stands for N, very particularly preferably all symbols X stand for CR, with the proviso that if CyC is bound to a bridge, it is a symbol X stands for C and the bridge is attached to this carbon atom.
  • CyC are the groups of the following formulas (CyC-1 a) to (CyC-20a),
  • Binding is preferred via the position marked with “o” in the formulas shown above, so that the radical R is then preferably not present in this position.
  • the structures shown above, which do not contain a carbon atom marked with an “o”, are preferably not bound directly to a bridge.
  • the position of the bond at which the (partial) ligands can be connected to one another by means of a bridge can vary
  • Metals may be different, the preference given in the structures of the formulas (CyC-1) to (CyC-20) and (CyC-1 a) to (CyC-20a), for example, for iridium.
  • the examples provide valuable information, the bridge preferably taking place via a position which is adjacent to the coordination or binding site with the metal atom.
  • Preferred groups among the groups (CyC-1) to (CyC-19) are the groups (CyC-1), (CyC-3), (CyC-8), (CyC-10), (CyC-12), ( CyC-13) and (CyC-16), and particularly preferred are the groups (CyC-1 a), (CyC-3a), (CyC-8a), (CyC-10a), (CyC-12a), (CyC -13a) and (CyC-16a).
  • CyC comprises a partial structure of the formula (2), (2a), (2-1) and / or (2a-1) or the preferred embodiments of this partial structure or is formed by suitable substitution with radicals R, in which case the groups X in formula (2) or (2a) stand for CR 1 .
  • a radical R particularly preferably represents in the preceding Embodiments of the group CyC set forth represent a partial structure of the formula (2) or (2a), so that the connection point shown in formula (2) by a dashed bond directly with the aromatic or heteroaromatic ring system set out in the group CyC
  • the CyC group is directly connected to the one in the CyC group by two connection points
  • CyD is a fleteroaryl group having 5 to 13 aromatic ring atoms, particularly preferably having 6 to 10 aromatic ring atoms, which coordinates to the metal via a neutral nitrogen atom or via a carbene carbon atom and which coordinates with one or several radicals R can be substituted and which is connected via a covalent bond to CyC.
  • Preferred embodiments of the group CyD are the structures of the following formulas (CyD-1) to (CyD-14),
  • X is the same or different at each occurrence CR or N with the proviso that a maximum of two symbols X per cycle stand for N;
  • W is the same or different at each occurrence NR, O or S;
  • R has the above, in particular for formula (I) or (la)
  • CyD-10 (CyD-13) and (CyD-14) via a neutral nitrogen atom
  • CyD-5 and (CyD-6) via a carbene carbon atom
  • CyD-11) and (CyD-12) via an anionic nitrogen atom to the metal.
  • a maximum of two symbols X in CyD preferably stand for N, particularly preferably a maximum of one symbol X in CyD stands for N, particularly preferably all symbols X stand for CR, with the proviso that when CyD is bound to a bridge, a Symbol X stands for C and the bridge is attached to this carbon atom.
  • CyD are the groups of the following formulas (CyD-1 a) to (CyD-14b),
  • the position of the bond at which the (partial) ligands can be connected to one another by means of a bridge can vary
  • Metals may be different, with the preference given in the structures of the formulas (CyD-1) to (CyD-14) and (CyD-1 a) to (CyD-14b), for example, for iridium.
  • the examples give valuable directions, the bridge preferably taking place via a position which is adjacent to the coordination or binding site with the metal atom.
  • Preferred groups among the groups (CyD-1) to (CyD-10) are the groups (CyD-1), (CyD-2), (CyD-3), (CyD-4), (CyD-5) and ( CyD-6), in particular (CyD-1), (CyD-2) and (CyD-3), and particularly preferred are the groups (CyD-1 a), (CyD-2a), (CyD-3a), ( CyD-4a), (CyD-5a) and (CyD-6a), in particular (CyD-1 a), (CyD-2a) and (CyD-3a).
  • CyC is an aryl or heteroaryl group with 6 to 13 aromatic ring atoms, and at the same time CyD is a heteroaryl group with 5 to 13 aromatic ring atoms.
  • CyC is particularly preferably an aryl or heteroaryl group with 6 to 10 aromatic ring atoms, and at the same time CyD is a heteroaryl group with 5 to 10 aromatic ring atoms.
  • CyC is very particularly preferably an aryl or heteroaryl group with 6 aromatic ring atoms and CyD is a heteroaryl group with 6 to 10 aromatic ring atoms. CyC and CyD can be substituted with one or more R groups.
  • CyD is a partial structure of the formula (2), (2a), (2-1) and / or (2a-1) or the preferred embodiments comprises this substructure or is formed by suitable substitution with radicals R, in which case the groups X in formula (2) or (2a) stand for CR 1 .
  • a radical R in the previously described embodiments of the group CyD particularly preferably represents a partial structure of the formula (2) or (2a), so that the point of attachment shown in formula (2) by a dashed bond directly with the aromatic set out in the group CyD or heteroaromatic ring system
  • the CyD group is directly connected to the one in the CyD group by two connection points
  • the above-mentioned preferred groups (CyC-1) to (CyC-20) and (CyD-1) to (CyD-14) can be combined with one another in the ligands of the formulas (L-1) and (L-2). At least one of the groups CyC or CyD can have a suitable connection point to a bridge, suitable connection points being identified with “o” in the formulas mentioned above. It is particularly preferred if the groups CyC and CyD mentioned above as particularly preferred, that is to say the groups of the formulas (CyC-1 a) to (CyC-20a) and the groups of the formulas (CyD1 -a) to (CyD-14b) can be combined with each other. Combinations in which neither CyC nor CyD has such a suitable attachment point for a bridge are therefore not preferred.
  • the above-mentioned preferred groups (CyD-1) to (CyD-14) in the ligands of the formulas (L-4) and (L-5) can be combined with groups of the Formulas (2), (2a), (2-1) and (2a-1) can be combined.
  • at least one of the groups CyD or a partial structure of the formulas (2), (2a), (2-1) and (2a-1) can have a suitable connection point to a bridge, suitable connection points in the formulas mentioned above having “o " Marked are.
  • Preferred ligands (L-1) are the structures of the following formulas (L-1- 1) and (L-1 -2), and preferred ligands (L-2) are the structures of the following formulas (L-2-1) to (L-2-3),
  • the ligands can optionally be connected by a bridge, the binding to the bridge preferably being possible via the position marked with “o”, the position marked with “o” being a carbon atom represents if this represents a bridge binding point.
  • Particularly preferred ligands (L-1) are the structures of the following formulas (L-1 -1 a) and (L-1 -2b), and particularly preferred ligands (L-2) are the structures of the following formulas (L-2 -1 a) to (L-2-3a), where the symbols used have the meanings mentioned above and the ligands can optionally be connected by a bridge, the binding to the bridge preferably being possible via the position marked with “o”, the position marked with “o” being a carbon atom represents if this represents a bridge binding point. If the ligands are not bridged, the position marked with “o” can also be substituted with a radical R.
  • the above-mentioned preferred groups CyD in the ligands of the formula (L-3) can be combined with one another as desired, it being preferred to have a neutral group CyD, that is to say a group (CyD-1) to (CyD-10), (CyD -13) or (CyD-14), with an anionic group CyD, ie a group (CyD-11) or CyD-12), the ligands can optionally be connected by a bridge, the binding to the bridge can preferably take place via the position marked with “o”, suitable connection points in the above formulas being marked with “o”.
  • the position of the bond at which the (partial) ligands can be connected to one another via a bridge can be different for different metals, with the stated preference in the Structures of the formulas (L-1-1) to (L-2-3) and (L-1-1 a) to (L-2-3a) or the preferred embodiments of these structures described below apply, for example, to iridium.
  • the examples provide valuable information, the bridge preferably taking place via a position which is adjacent to
  • Formula (RB-7) Formula (RB-8) Formula (RB-9) Formula (RB-10) where R 1 has the meanings given above and the dashed bonds indicate the bonds to CyC or CyD.
  • the asymmetrical of the above groups can be in either of the two Possibilities are built in, for example in the group of the formula (RB-10) the oxygen atom can bind to the group CyC and the carbonyl group to the group CyD, or the oxygen atom can bind to the group CyD and the carbonyl group to the group CyC.
  • the group of the formula (RB-7) is particularly preferred if this results in the formation of a ring to form a six-membered ring, as represented, for example, by the formulas (L-23) and (L-24) below.
  • Preferred ligands which are formed by ring formation of two radicals R on the different cycles are the structures of the formulas (L-5) to (L-32) listed below,
  • the ligands optionally being able to be connected by a bridge, the binding to the bridge preferably being able to take place via the position marked with “o”, the position marked with “o” being a Represents carbon atom if it represents a bridge binding site.
  • one symbol X stands for N and the other symbols X stand for CR, or all symbols X stand for CR with the proviso that if these ligands are linked via a bridge, a symbol X stands for C and the bridge is bonded to this carbon atom.
  • Nitrogen atom a group R is bound as a substituent which is not hydrogen or deuterium.
  • This substituent R is preferably a group selected from CF3, OCF3, alkyl or alkoxy groups with 1 to 10 C atoms, in particular branched or cyclic alkyl or alkoxy groups with 3 to 10 C atoms, one
  • Another suitable bidentate ligand is the ligand of the following formula (L-33) or (L-34),
  • R has the meanings given above, * represents the position of the coordination to the metal, where the ligands can optionally be connected by a bridge, the bond to the bridge preferably via the position marked with "o", and the following applies to the other symbols used:
  • X is the same or different at each occurrence CR or N with the proviso that a maximum of one symbol X per cycle stands for N, where X is C, if at this position the ligand with a bridge
  • Carbon atoms preferably have a structure of the following formula (BR-11),
  • ligands (L-33) or (L-34) at most one group of the formula (BR-11) is present. They are therefore preferably ligands of the following formulas (L-35) to (L-40),
  • Y is the same or different at each occurrence for CR 1 or N and preferably at most one symbol Y for N, where R 1 has the meaning given above.
  • a total of 0, 1 or 2 of the symbols X and, if present, Y are in the ligand of the formulas (L-33) to (L-40).
  • Y is particularly preferably a total of 0 or 1 of the symbols X. and, if available, Y for N.
  • the group X which is in the ortho position for coordination to the metal, stands for CR.
  • this radical R which is bonded to the metal in the ortho position for coordination, is preferably selected from the group consisting of H, D,
  • one of the atoms X or, if present, Y is N, if a group R which is not hydrogen or deuterium is bonded as a substituent adjacent to this nitrogen atom.
  • This substituent R is preferably a group selected from CF3, OCF3, alkyl or alkoxy groups with 1 to 10 C atoms, in particular branched or cyclic alkyl or alkoxy groups with 3 to 10 C atoms, with a dialkylamino group 2 to 10 carbon atoms, aromatic or heteroaromatic ring systems or aralkyl or fleteroaralkyl groups. These groups are sterically demanding groups.
  • this radical R can also form a cycle with an adjacent radical R.
  • bidentate ligands are the structures of the following formulas (L-41) to (L-45), preferably at most one of the three bidentate ligands representing one of these structures,
  • the ligands (L-41) to (L-43) coordinating to the metal via the explicitly drawn nitrogen atom and the negatively charged oxygen atom and the ligands (L-44) and (L-45) via the two oxygen atoms, R and X have the meanings given above, in particular for formula (I) or (Ia), it being possible for the ligands to be optionally connected by a bridge, the binding to the bridge preferably being possible via the position marked with “o”, where XC is if the ligand is connected to a bridge at this position or, in formula (L-44) or (L-45), the carbon atom can have a substituent R if the ligand is not connected to a bridge at this position.
  • the preferred embodiments for X outlined above are also preferred for the ligands of formulas (L-41) to (L-43).
  • the ligands optionally being able to be connected by a bridge, the binding to the bridge preferably being possible via the position marked with “o” or in formula (L-41 a), (L-42a) or (L-43a) the carbon atom
  • R particularly preferably represents hydrogen, the ligands optionally being able to be connected by a bridge, the binding to the bridge preferably being possible via the position marked with “o”, so that the structures of the following formulas ( L-41 b) to (L-43b),
  • X and R have the meanings given above and * represents the position of the coordination to the metal, where the ligands can optionally be connected by a bridge.
  • the group R bonded to N preferably does not stand for H, but for an alkyl, heteroalkyl, aryl or heteroaryl group, as has been explained above for R.
  • Preferred ligands of the formula (L-46) are therefore the ligands of the following formulas (L-46a),
  • Embodiments preferably comprise at least one partial structure of the formula (2) and / or (2a), this partial structure preferably being formed by suitable substitution with radicals R or R 1 , in which case the groups X in formula (2) or (2a) stand for CR 1 .
  • a radical R in the previously described embodiments of the ligands of the formulas (L-1) to (L-46) particularly preferably represents a partial structure of the formula (2) or (2a), so that the one in formula (2) is indicated by a dashed line Binding point set out directly with the aromatic or
  • heteroaromatic ring system is connected.
  • ligands of the formulas (L-1) to (L-46) are replaced by two
  • the metal complexes correspond to the general formula
  • the ligands L and L ' can be regarded as three bidentate partial ligands that coordinate to a metal.
  • the bridge can preferably represent an aryl or heteroaryl group with 5 to 36 aromatic ring atoms, which can be substituted by one or more radicals R.
  • one or more radicals R Preferably one
  • Metal complex of the general formula (1 a) contain structures of the formulas (2-1) and / or (2a-1) set out above.
  • a tetradentate ligand system is preferably formed in a structure according to formula (1a).
  • organometallic complexes in the sense of the present invention is a complex which has at least one metal-carbon bond to the ligand.
  • the iridium or platinum complex is not charged, i. H. electrically neutral.
  • the iridium complex preferably contains either three bidentate, monoanionic
  • Ligand or a tripodal, hexadentate, trianionic ligand, and the platinum complex contains either two bidentate, monoanionic ligands or a tetradentate, dianionic ligand.
  • the binding of the ligand to the iridium or the platinum can be both a coordination bond and a covalent bond or the covalent portion of the bond can vary depending on the ligand. If it is mentioned in the present application that the ligand or the ligand coordinates or binds to the iridium or the platinum, then
  • M is platinum, so that an organometallic platinum complex comprises a partial structure of the formula (2) or (2a). If M is platinum, this complex preferably comprises two bidentate ligands which can be linked to one another.
  • these ligands are selected identically or differently preferably from the ligands of the formulas (L-1), (L-2) and (L-3) shown above, with the abovementioned preferences also being valid for this.
  • M platinum and the platinum complex comprises a tetradentate ligand, then this can be represented schematically by the following formula (Lig '):
  • V ' is selected from CR2, NR, O, S and BR, preferably CR2 and
  • L1 and L2 are identical or different each time bidentate ligands, preferably monoanionic bidentate ligands. Since the ligand has two bidentate ligands, there is a total of one tetradentate ligand, that is to say a ligand which coordinates or binds to the platinum via four coordination sites.
  • the platinum complex formed with this ligand of the formula (Lig ') can thus be represented schematically by the following formula:
  • the position of the bond at which the (partial) ligands can be connected to one another via a bridge can be different
  • Metals may be different, with the stated preference
  • the examples provide valuable information, the bridge preferably taking place via a position which is adjacent to the coordination or binding site with the metal atom.
  • M is iridium. It can be provided that the metal is Ir (III) and the
  • Metal complex has three bidentate ligands, two of the bidentate ligands to the iridium via a carbon atom and a
  • Coordinates nitrogen atoms preferably the third of the bidentate ligands coordinating to the iridium via a carbon atom and a nitrogen atom or via two carbon atoms.
  • the tripodal, hexadentate ligand contains three bidentates
  • Partial ligands which may be the same or different and which coordinate to an iridium atom, the three bidentate part-ligands being linked via a bridge of the following formula (3) or formula (4)
  • X 1 is the same or different at each occurrence CR or N;
  • a 1 is the same or different at each occurrence C (R) 2 or O;
  • X 2 is the same or different at each occurrence CR or N or two adjacent groups X 2 together represent NR, O or S, so that a five-membered ring is formed, and the remaining X 2 are the same or different each time for CR or N; or two adjacent groups X 2 together stand for CR or N if one of the groups X 3 stands for N in the cycle, so that a five-membered ring is formed; with the proviso that a maximum of two adjacent groups X 2 represent N;
  • X 3 is C at each occurrence or one group X 3 stands for N and the other group X 3 in the same cycle stands for C; with the proviso that two adjacent groups X 2 together represent CR or N if one of the groups X 3 in the cycle is N;
  • R ' is the same or different H, D, one with each occurrence
  • alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, where the alkyl group can in each case be substituted with one or more radicals R 1 and with one or more non-adjacent CFh groups Si (R 1 ) 2 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 ;
  • the three bidentate partial ligands can be closed to form a cryptate in addition to the bridge of the formula (3) or (4).
  • radicals R or R 1 or R 2 together form a ring system, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic.
  • the radicals which form a ring system with one another can be adjacent, ie these radicals are bonded to the same carbon atom or to carbon atoms which are bonded directly to one another, or they can be further apart.
  • the structure of the hexadentate, tripodal ligands can be represented schematically by the following formula (Lig):
  • V represents the bridge according to formula (3) or (4) and L1, L2 and L3, identical or different, each represent bidentate partial ligands, preferably monoanionic bidentate partial ligands.
  • bidentat means that the respective ligand in complex M coordinates or binds to the iridium via two coordination sites.
  • Tripodal means that the ligand has three partial ligands which are bonded to the bridge V or the bridge of the formula (3) or (4). Since the ligand has three bidentate partial ligands, there is a total of one hexadentate ligand, that is to say a ligand which coordinates or binds to the iridium via six coordination sites.
  • the term “bidentate partial ligand” means that this unit would be a bidenate ligand if the bridge of the formula (3) or (4) were not present. Due to the formal abstraction of a hydrogen atom on this bidentate ligand and the connection to the bridge of formula (3) or (4), however, this is not a separate ligand, but part of the hexadentate ligand thus formed, so that the term “ Partial ligand ”is used.
  • the iridium complex formed with this ligand of the formula (Lig) can thus be represented schematically by the following formula: where V represents the bridge according to formula (3) or (4) and L1, L2 and L3, identically or differently, each represent bidentate partial ligands in each occurrence.
  • Suitable embodiments of the group of formula (3) are the structures of the following formulas (6) to (9), and suitable embodiments of the group of formula (4) are
  • R is the same or different on each occurrence H, D, F, CN, a
  • radicals R 1 straight-chain alkyl or alkoxy group with 1 to 10 C atoms or an alkenyl group with 2 to 10 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 10 C atoms, each of which is substituted by one or more radicals R 1 may, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 1 ;
  • R 1 is the same or different H, D, F, CN, a
  • radicals R 2 can, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each represented by one or more
  • Radicals R 2 can be substituted; two or more adjacent radicals R 1 here can form a ring system with one another;
  • R 2 is the same or different H, D, F or a at each occurrence
  • R is the same or different on each occurrence H, D, F, CN, a
  • R 1 is the same or different, H, D, F, CN, a straight-chain alkyl group with 1 to 4 C atoms or a branched or cyclic alkyl group with 3 to 6 C atoms, each with one or more radicals R 2 may be substituted, or an aromatic or heteroaromatic ring system with 6 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 ; two or more adjacent radicals R 1 here can form a ring system with one another;
  • R 2 is the same or different H, D, F or a at each occurrence
  • all groups X 1 in the group of the formula (3) are CR, so that the central trivalent cycle of the formula (3) is a benzene. All groups X 1 are particularly preferably CH. In a further preferred embodiment of the invention, all groups X 1 represent a nitrogen atom, so that the central trivalent cycle of the formula (3) represents a triazine.
  • Preferred embodiments of the formula (3) are thus the structures of the formulas (6) and (7).
  • the structure of the formula (6) is particularly preferably a structure of the following formula (6 '),
  • the group of formula (5) can be a heteroaromatic five-membered ring or an aromatic or heteroaromatic six-membered ring.
  • the group of the formula (5) contains at most two heteroatoms in the aromatic or heteroaromatic unit, particularly preferably at most one heteroatom. This does not exclude that substituents that may be attached to this group can also contain heteroatoms.
  • this definition does not preclude the formation of condensed aromatic or heteroaromatic structures, such as naphthalene, benzimidazole, etc., from the ring formation of substituents.
  • the condensed groups can be condensed at any position of the unit according to formula (5), as represented by the condensed benzo group in formulas (15a) to (15c).
  • the groups as they are attached to the unit of the formula (5) in the formulas (15d) to (15j) are therefore also condensed at other positions in the unit of the formula (5).
  • the group of the formula (3) can particularly preferably be represented by the following formulas (3a) to (3m), and the group of the formula (4) can particularly preferably be represented by the following formulas (4a) to (4m):
  • X 2 is preferably the same or different for each occurrence of CR.
  • the group of formulas (3a) to (3m) is selected from the groups of formulas (6a ') to (6m') and the group of formulas (4a) to (4m) is selected from the groups of formulas (10a ') to (10m'),
  • X 2 is preferably the same or different for each occurrence of CR.
  • a particularly preferred embodiment of the group of the formula (3) is the group of the following formula (6a "),
  • R in the above formulas are particularly preferably identical or different H, D or an alkyl group having 1 to 4 carbon atoms.
  • R H is very particularly preferred.
  • the structure of the following formulas (6a ′′) is very particularly preferred,
  • the metal complex according to the invention contains two substituents R or two substituents R 1 which are bonded to adjacent carbon atoms and which together form an aliphatic ring according to one of the formulas described below.
  • the two substituents R which form this aliphatic ring can be attached to the bridge of the formulas (3) or
  • the aliphatic ring which is formed by the ring formation of two substituents R with one another or of two substituents R 1 with one another is preferably described by one of the following formulas (40) to (46),
  • R 3 is not equal to H.
  • a double bond between the two carbon atoms is formally represented in the structures of the formulas (40) to (46) shown above and in the further embodiments of these structures mentioned as preferred. This represents a simplification of the chemical structure if these two carbon atoms are integrated in an aromatic or heteroaromatic system and the bond between these two carbon atoms is therefore formally between the degree of bond of a single bond and that of a double bond.
  • the drawing in of the formal double bond is thus not to be interpreted as limiting the structure, but it is obvious to the person skilled in the art that this is an aromatic bond.
  • Benzylic protons are taken to mean protons that bind to a carbon atom that are bonded directly to the ligand. This can be achieved in that the carbon atoms of the aliphatic ring system which bind directly to an aryl or heteroaryl group are completely substituted and contain no hydrogen atoms bonded.
  • the absence of acidic benzylic protons in formulas (40) to (42) is achieved in that Z 1 and Z 3 , when they represent C (R 3 ) 2, are defined such that R 3 is not hydrogen is. This can also be achieved by the fact that the carbon atoms of the aliphatic ring systems that bind directly to an aryl or heteroaryl group that
  • At most one of the groups Z 1 , Z 2 and Z 3 represents a hetero atom, in particular O or NR 3
  • the other groups represent C (R 3 ) 2 or C (R 1 ) 2 or Z 1 and Z 3 stand for the same or different in each occurrence for O or NR 3 and Z 2 stands for C (R 1 ) 2
  • Z 1 and Z 3 are identical or different in each occurrence for C (R 3 ) 2 and Z 2 stands for C (R 1 ) 2 and particularly preferably for C (R 3 ) 2 or CH 2 .
  • Preferred embodiments of the formula (40) are therefore the structures of the formula (40-A), (40-B), (40-C) and (40-D), and a particularly preferred embodiment of the formula (40-A) ) are the structures of the formulas (40-E) and (40-F), Formula (40-E) Formula (40-F) wherein R 1 and R 3 have the meanings given above and Z 1 , Z 2 and Z 3 are identical or different in each occurrence and represent O or NR 3 .
  • Preferred embodiments of the formula (41) are the structures of the following formulas (41 -A) to (41 -F),
  • Preferred embodiments of the formula (42) are the structures of the following formulas (42-A) to (42-E), Formula (42-D) Formula (42-E) wherein R 1 and R 3 have the meanings given above and Z 1 , Z 2 and Z 3 are the same or different in each occurrence for O or NR 3 .
  • the radicals R 1 which are bonded to the bridgehead are H, D, F or CFI3.
  • Z 2 further preferably represents C (R 1 ) 2 or O, and particularly preferably C (R 3 ) 2.
  • Preferred embodiments of the formula (43) are thus a structure of the formula (43-A) and (43-B), and a particularly preferred embodiment of the formula (43-A) is a structure of the formula (43-C),
  • the radicals R 1 which are bonded to the bridgehead are H, D, F or CFI3.
  • Z 2 further preferably represents C (R 1 ) 2.
  • Preferred embodiments of the formulas (44), (45) and (46) are thus the
  • the group G is furthermore preferably in the formulas (43), (43-A), (43-B), (43-C), (44), (44-A), (45), (45-A) , (46) and (46-A) for a 1,2-ethylene group which can be substituted with one or more radicals R 2 , where R 2 is preferably the same or different on each occurrence for H or an alkyl group with 1 to 4 C. -Atoms, or an ortho-arylene group with 6 to 10 carbon atoms, which can be substituted with one or more radicals R 2 , but is preferably unsubstituted, in particular an ortho-phenylene group, which can be substituted with one or more radicals R 2 can, but is preferably unsubstituted.
  • R 3 in the groups of the formulas (40) to (46) and in the preferred embodiments, identically or differently, represents F, a straight-chain alkyl group having 1 to 10 C atoms or one at each occurrence branched or cyclic alkyl group with 3 to 20 C atoms, where one or more non-adjacent CFh groups can be replaced by R 2 C CR 2 and one or more Fl atoms can be replaced by D or F, or an aromatic or heteroaromatic ring system with 5 to 14 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 ; two radicals R 3 , which are bonded to the same carbon atom, can form an aliphatic or aromatic ring system with one another and thus span a spiro system; furthermore, R 3 can form an aliphatic ring system with an adjacent radical R or R 1 .
  • R 3 in the groups of formulas (40) to (46) and in the preferred embodiments, identically or differently, represents F, a straight-chain alkyl group having 1 to 3 C atoms, in particular, each time it occurs Methyl, or an aromatic or heteroaromatic ring system with 5 to 12 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 , but is preferably unsubstituted; two radicals R 3 , which are bonded to the same carbon atom, can form an aliphatic or aromatic ring system with one another and thus span a spiro system; furthermore, R 3 can form an aliphatic ring system with an adjacent radical R or R 1 .
  • radicals R are particularly preferably selected identically or differently from the group consisting of H, D, F, N (R 1 ) 2 , a straight-chain alkyl group having 1 to 6 C atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where one or more H atoms can be replaced by D or F, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 ; two adjacent radicals R or R with R 1 here can also form a mono- or polycyclic ring system with one another.
  • Purposes can be used.
  • Embodiments can be combined with one another as desired.
  • the preferred embodiments mentioned above apply simultaneously.
  • the compounds according to the invention can be prepared by various methods. However, there have been the following
  • the present invention therefore furthermore relates to a process for the preparation of the compounds according to the invention, preferably compounds comprising at least one structure of the formulas (I), (Ia), (II), (Ila), (purple) to (Illh), (IVa ) to (IVh), and / or metal complexes comprising at least one partial structure of the formulas (2), (2a), (2-1), (2a-1), in which, in a coupling reaction, a compound comprising a structure of the formula ( I), (la), (II) and / or (lla), with a compound comprising at least one aromatic or heteroaromatic group.
  • Suitable compounds comprising at least one structure of the formula (I), (Ia), (II) and / or (Ila) 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 becomes.
  • Particularly suitable and preferred coupling reactions which all lead to C-C linkages and / or C-N linkages are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI,
  • the compounds according to the invention comprising structures of the 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 be suitable
  • substituents for example by longer alkyl groups (approx. 4 to 20 carbon atoms), in particular branched alkyl groups, or
  • aryl groups for example xylyl, mesityl or branched terphenyl or quaterphenyl groups, the one
  • soluble compounds are particularly suitable for processing from solution, for example by printing processes.
  • the compounds according to the invention comprising at least one structural element of the formulas (I), (la), (II), (lla), have a structure of the formulas (purple) to (IIIh), (IVa) to (IVh) , and / or metal complexes according to the invention, comprising at least a partial structure of the formulas (2), (2a), (2-1) and / or (2a-1), already have an increased solubility in these solvents.
  • the compounds of the present invention may contain one or more crosslinkable groups.
  • Crosslinkable group means a functional group that is capable of irreversibly reacting. This creates a cross-linked material that is insoluble.
  • Crosslinking can usually be supported by heat or by UV, microwave, X-ray or electron radiation. There is 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 for the
  • Crosslinking is required (e.g. ⁇ 200 ° C for thermal
  • crosslinkable groups are units which contain a double bond, a triple bond, a precursor which is capable of forming a double or triple bond in situ, or a heterocyclic, addition-polymerizable radical.
  • Crosslinkable groups include vinyl, alkenyl, preferably ethenyl and others
  • the compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds 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 the production of corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably carried out 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 furthermore relates to oligomers, polymers or dendrimers containing one or more of the abovementioned
  • the polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences as described above apply to the repeat units of the compounds according to the invention in oligomers, dendrimers and polymers.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Copolymers are preferred, the units having structural elements of the formulas (I), (la), (II), (lla) or units of the formulas (purple) to (IIIh), (IVa) to (IVh) or those previously and Below preferred embodiments of 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 fluorenes (for example according to EP 842208 or WO 2000/022026), spirobifluorenes (for example according to EP 707020, EP 894107 or WO 2006/061 181) , Para-phenylenes (e.g.
  • WO 92/18552 carbazoles (e.g. according to WO 2004/070772 or WO 2004/1 13468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. B. according to WO 2005/014689), cis- and trans-indofluorenes (e.g. according to WO 2004/041901 or WO 2004/1 13412), ketones (e.g. according to WO 2005/040302), phenanthrenes (e.g. B. according to WO 2005/104264 or WO 2007/017066) or several of these units.
  • the polymers, oligomers and dendrimers can also contain further units, for example hole transport units, in particular those based on triaryl amines, and / or electron transport units.
  • Functional layers of electronic devices can be used, preferably compounds comprising at least one structural element of the formulas (I), (la), (II), (lla), a structure of the formulas (purple) to (IIIh), (IVa) to (IVh) , and / or a metal complex comprising at least a partial structure of the formulas (2), (2a), (2-1), (2a-1), or the preferred embodiments described above and below, which have a glass transition temperature of at least 70 ° C, particularly preferably at least 1 10 ° C, very particularly preferably at least 125 ° C and particularly preferably at least 150 ° C, determined according to DIN 51005 (version 2005-08).
  • Formulations of the compounds according to the invention are necessary for processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this. Suitable and preferred
  • Solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl TFIF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-) - Fenchon,
  • Another object of the present invention is therefore a formulation containing a 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 solvents mentioned above, or a mixture of these solvents.
  • the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound, for example a fluorescent dopant, a phosphorescent dopant or a compound, the TADF (thermally activated delayed fluorescence ) shows, in particular a phosphorescent dopant, and / or a further matrix material.
  • This further connection can also be polymeric.
  • Another object of the present invention is therefore a composition containing a compound according to the invention and at least one further organically functional material.
  • Functional materials are generally the organic or inorganic materials that are inserted between the anode and cathode.
  • the organically functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials, hole blocking materials, Wide band gap materials and n-dopants.
  • the present invention therefore also relates to a composition
  • a composition comprising at least one compound according to the invention, preferably a compound comprising at least one structural element of the formulas (I), (Ia), (II), (Ila), a structure of the formulas (purple) to (IIIh) , (IVa) to (IVh), and / or a metal complex, comprising at least a partial structure of the formulas (2), (2a), (2-1), (2a-1), or those above and below
  • the present invention has the further matrix material
  • the present invention further provides a composition comprising at least one compound according to the invention, preferably a compound comprising at least one structural element of the formulas (I), (Ia), (II), (Ila), a structure of the formulas (purple) to ( IIIh), (IVa) to (IVh), and / or a metal complex, comprising at least a partial structure of the formulas (2), (2a), (2-1), (2a-1), or those previously and subsequently
  • the additional connection can preferably have a band gap of 2.5 eV or more, preferably 3.0 eV or more, very preferably 3.5 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 and the lowest excited singlet state Si of the materials are determined using quantum chemical calculations.
  • a geometry optimization is first carried out using the “Ground State / Semi-empirical / Default Spin / AM 1 / Charge 0 / Spin Singlet” method. This is followed by an energy calculation based on the optimized geometry.
  • the method “TD-SCF / DFT / Default Spin / B3PW91” with the basic set “6-31 G (d)” is used (Charge 0, Spin Singlet).
  • the geometry is determined using the “Ground State / Hartree-Fock / Default
  • 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 frequently used programs 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 at least one structural element of the formulas (I), (la), (II), (lla) or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), and / or a metal complex comprising at least one partial structure of the formulas (2), (2a), (2-1), (2a-1), or the preferred embodiments described above and below, and at least one phosphorescent emitter , whereby the term phosphorescent emitter is also understood to mean phosphorescent dopants.
  • a dopant is understood to mean that component whose proportion in the mixture is the smaller one. Accordingly, a matrix material in a system containing a matrix material and a dopant is understood to mean that component whose proportion in the mixture is the larger.
  • Preferred phosphorescent dopants for use in matrix systems are the preferred phosphorescent dopants given below.
  • phosphorescent dopants are typical
  • Compounds includes, in which the light emission takes place through a spin-prohibited transition, for example a transition from one excited triplet state or a state with a higher one
  • Suitable phosphorescent compounds are, in particular, compounds which, when suitably excited, emit light, preferably in the visible range, and also at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 contain, especially a metal with this atomic number.
  • Preferred phosphorescence emitters are compounds which contain copper, molybdenum, tungsten, rhenium,
  • the compounds described above comprising at least one structural element of the formulas (I), (la), (II), (lla), a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), and / or a metal complex comprising at least one partial structure of the formulas (2), (2a), (2-1), (2a-1), or the preferred embodiments listed above, can preferably be used as an active component in an electronic device .
  • an electronic device is a device understood which anode, cathode and at least one layer between anode and cathode contains, this layer containing at least one organic or organometallic compound.
  • the electronic device according to the invention thus contains anode, cathode and at least one intermediate layer which contains at least one compound comprising structures of the formula (I).
  • Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting devices Transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), organic electrical sensors, light-emitting electrochemical cells
  • OLEDs organic electroluminescent devices
  • O-ICs organic integrated circuits
  • O-FETs organic field-effect transistors
  • O-TFTs organic thin-film transistors
  • O-TFTs organic light-emitting devices Transistors
  • O-LETs organic solar cells
  • O-SCs organic optical detectors
  • organic laser diodes O-laser
  • organic plasmon emitting devices DM Koller et ai, Nature Photonics 2008, 1-4
  • OLEDs organic electroluminescent devices
  • PLEDs organic electroluminescent devices
  • phosphorescent OLEDs contained in at least one Layer at least one compound comprising structures of the formula (I) and / or (la)).
  • Organic are particularly preferred
  • Electroluminescent devices are generally the organic or inorganic materials which are introduced between the anode and cathode, for example charge injection, charge transport or charge blocking materials, but in particular emitters and matrix materials.
  • Organic electroluminescent devices are a preferred embodiment of the invention.
  • the organic electroluminescent device contains cathode, anode and at least one emitting layer. In addition to these layers, it can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers,
  • Electron injection layers exciton blocking layers
  • Electron blocking layers, charge generation layers and / or organic or inorganic p / n junctions It is possible for one or more hole transport layers to be p-doped, for example with metal oxides such as M0O3 or WO3 or with (per) fluorinated
  • Electron transport layers are n-doped.
  • interlayers can be introduced between two emitting layers which, for example, have an exciton-blocking function and / or
  • the organic electroluminescent device can be a
  • Tandem OLEDs are also preferred. It can also be a hybrid system, where one or more layers fluoresce and one or more other layers phosphoresce.
  • the organic electroluminescent device contains the compound according to the invention, preferably a compound comprising at least one structural element of the formulas (I), (Ia), (II), (Ila) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), or the preferred ones listed above
  • Embodiments as matrix material preferably as
  • an emissive layer comprises at least one emissive compound.
  • the present invention comprises an organic one according to the invention
  • Electroluminescent device the compound according to the invention, preferably a compound comprising at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh ), or the preferred ones listed above
  • Suitable matrix materials which, in combination with the compounds comprising at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (lilac) to (lllh), (IVa) to ( IVh), or can be used 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, in particular monoamines, e.g. B. according to WO 2014/015935, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or those in WO 2005/039246, US
  • bipolar matrix materials e.g. B. according to WO 2007/137725, silanes, z. B. according to WO 005/111172, Azaborole or Boronester, z. B. according to WO 2006/117052, triazine derivatives, for. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, e.g. B. according to EP 652273 or WO
  • a further phosphorescent emitter which emits at shorter wavelengths than the actual emitter, can likewise be present as a co-host in the mixture.
  • Preferred co-host materials are triarylamine derivatives, in particular monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.
  • charge-transporting matrix material and an electrically inert matrix material, which is not or not to a significant extent
  • Charge transport is involved, such as. B. described in WO 2010/108579.
  • triplet emitter with the shorter-wave emission spectrum serves as a co-matrix for the triplet emitter with the longer-wave emission spectrum.
  • a compound according to the invention can particularly preferably comprise at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), in a
  • the matrix material comprising the compound comprises at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), or the preferred embodiments explained above and below in the electronic device in Combination with one or more dopants, preferably
  • the proportion of the matrix material in the emitting layer in this case is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably for fluorescent emitting layers between 92.0 and 99.5% by volume and for phosphorescent emitting layers between 85.0 and 97.0% by volume.
  • the proportion of the dopant is between 0.1 and
  • 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 larger.
  • the proportion of an individual matrix material in the system can be smaller than the proportion of an individual dopant.
  • the compounds comprising at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), or the preferred ones explained above and below
  • Embodiments used as a component of 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 combined in a single mixed matrix component, 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 precise information on mixed matrix systems can be found, inter alia, in application WO 2010/108579.
  • the present invention furthermore 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
  • cathode Metals with low work function, metal alloys or multi-layer structures made of different metals are preferred as cathode, such as, for example, alkaline earth metals, alkali metals, main group metals or lanthanides (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.) . Alloys made of an alkali or alkaline earth metal and silver are also suitable, for example an alloy of magnesium and silver. In the case of multilayer structures, other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as, for example, B. Ag, in which case combinations of the metals such as Mg / Ag, Ca / Ag or Ba / Ag are generally used. It can also be preferred between a metallic cathode and the
  • organic semiconductor to introduce a thin intermediate layer of a material with a high dielectric constant.
  • a material with a high dielectric constant for example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates are possible (e.g. LiF, L12O, BaF2, MgO, NaF, CsF, CS2CO3, etc.).
  • Organic alkali metal complexes are also suitable for this, e.g. B. Liq (lithium quinolinate).
  • the layer thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode.
  • the anode preferably has a work function greater than 4.5 eV vs. Vacuum on.
  • metals with a high redox potential are suitable for this, such as Ag, Pt or Au.
  • metal / metal oxide electrodes eg Al / Ni / NiO x , Al / PtO x
  • at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (O-SC) or the coupling out of light (OLED / PLED, O-LASER).
  • Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred.
  • conductive, doped organic materials in particular conductive doped polymers, e.g.
  • a p-doped hole transport material is applied to the anode as a hole injection layer, metal oxides, for example M0O3 or WO3, or (per) fluorinated electron-deficient aromatics being suitable as p-dopants.
  • metal oxides for example M0O3 or WO3, or (per) fluorinated electron-deficient aromatics being suitable as p-dopants.
  • Other suitable p-dopants are HAT-CN (hexacano-hexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection in materials with a deep HOMO, i.e. a large HOMO.
  • 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 thereby
  • Sublimation processes are coated.
  • the materials Evaporated in vacuum sublimation systems at an initial pressure of usually less than 10 -5 mbar, preferably less than 10 -6 mbar. It is also possible that the initial pressure is still lower or even higher, for example less than 10 -7 mbar.
  • an electronic device in particular an organic electroluminescent device, which thereby
  • OVPD Organic Vapor Phase Deposition
  • Carrier gas sublimation are coated.
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and 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 thereby
  • ком ⁇ онент B. by spin coating, or with any printing method, 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 (ink jet printing). Soluble compounds are required for this, which are obtained, for example, by suitable substitution.
  • any printing method 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 (ink jet printing).
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink jet printing
  • the electronic device especially the organic one
  • Electroluminescent device can also be manufactured as a hybrid system by applying one or more layers of solution and evaporating one or more other layers.
  • an emitting layer comprising a compound according to the invention comprising at least one structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (lllh), ( IVa) to (IVh), or a metal complex, comprising structures of the formulas (2), (2a), (2-1) and / or (2a-1), and a matrix to apply material from solution and to evaporate a hole blocking layer and / or an electron transport layer thereon in vacuo.
  • Structural element of the formulas (I), (la), (II), (lla) and / or a structure of the formulas (purple) to (IIIh), (IVa) to (IVh), or metal complexes, comprising structures of the formulas (2 ), (2a), (2-1) and / or (2a-1), or the preferred embodiments listed above can be used.
  • the electronic devices according to the invention are distinguished by one or more of the following surprising advantages over the prior art:
  • Electron transport materials, hole conductor materials and / or as host materials have excellent efficiency.
  • the efficiency is significantly higher than that of analog Connections that do not contain a bullvalene structure.
  • the compounds, oligomers, polymers or dendrimers according to the invention which can be used as active compounds in an organic electronic device, or the preferred embodiments described above and below, have a slight effect
  • Oligomers, polymers or dendrimers which can be used as active compounds in an organic electronic device or the preferred ones mentioned above and below
  • Embodiments electron transport materials, hole conductor materials and / or host materials have excellent color purity.
  • the compounds, oligomers, polymers or dendrimers according to the invention which can be used as active compounds in an organic electronic device, or the preferred embodiments explained above and below show a very high thermal and photochemical stability and lead to
  • Electroluminescent devices the formation of optical signals
  • Loss channels can be avoided. These devices are characterized by a high PL and thus high EL efficiency of emitters and an excellent energy transfer from the matrices to dopants. 6. Compounds, oligomers, polymers or dendrimers which can be used as an active compound in an organic electronic device, or the preferred embodiments explained above and below have excellent results
  • An electronic device is understood to mean a device which
  • the component contains at least one layer containing at least one organic compound.
  • the component can also contain inorganic materials or layers which are made entirely of inorganic materials.
  • Another object of the present invention is therefore the use of the compounds or mixtures according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • Yet another object of the present invention is the use of a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as a phosphorescent emitter,
  • fluorescent emitter emitter showing TADF (thermally activated delayed fluorescence), host material, electron transport material,
  • Electron injection material hole conductor material, hole injection material, Electron blocking material, hole blocking material and / or wide band gap material, preferably as an emitter, host material, hole conductor material and / or electron transport material.
  • Another object of the present invention is an electronic device containing at least one of the compounds or mixtures according to the invention described above.
  • Electronic device is particularly preferably selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), organic electrical sensors, light-emitting electrochemical cells (LECs),
  • organic laser diodes O-lasers
  • organic plasmon emitting devices D.M. Koller et ai, Nature Photonics 2008, 1-4
  • OLEDs organic electroluminescent devices
  • PLEDs organic electroluminescent devices
  • 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, ie. 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.
  • a metal complex which is identical or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as hole transport or hole injection material, such as. B. in WO
  • 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 using the compounds according to the invention in organic electroluminescent devices
  • the following syntheses are carried out in a protective gas atmosphere in dried solvents.
  • the metal complexes are also handled under 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 connections refer to the CAS numbers of the compounds known from the literature.
  • a valence-isomeric or tautomeric form is shown as a representative.
  • n-heptane 100 ml of n-heptane are mixed with 330 mg (0.5 mmol) of bis [(1, 2,5,6-h) -1, 5-cyclo-octadiene] di ⁇ -methoxydi-iridium (l) [12148-71 -9 ], then with 268 mg (1 mmol) of 4,4 - di-tert-butyl- [2,2-] bipyridinyl [72914-19-3] and then with 508 mg (2 mmol) of bis- (pinacolato) diborane offset and 15 min. stirred at room temperature.
  • the residue is taken up in 50 ml of ethyl acetate, washed three times with 30 ml of 3% by weight aqueous acetylcysteine solution, three times with 30 ml of water and once with 30 ml of sat. Saline and dries over magnesium sulfate.
  • the drying agent is filtered off, the filtrate is evaporated to dryness, the solid is stirred warm with 20 ml of methanol, the product which has crystallized out is filtered off with suction, washed twice with 5 ml of methanol each time and dried in vacuo.
  • Residue is flash chromatographed (CombiFlash torrent from A. Semrau). Yield: 1.65 g (4 mmol), 40%; Purity: approx. 97% n.
  • Vacuum takes up the residue in 100 ml DCM, mixed with 30 ml conc. Ammonia solution, stirred for 1 h at room temperature, separates the org. Phase, washes three times with 30 ml conc. Ammonia solution, washes three times with 30 ml of 3% by weight aqueous acetylcysteine solution, three times with 30 ml of water and once with 30 ml of sat. Saline and dries over magnesium sulfate. The magnesium sulfate is filtered off over a silica gel bed pre-slurried with DCM, the filtrate is evaporated to dryness and the residue is flash chromatographed (CombiFlash Torrent from A. Semrau). Yield: 1.25 g (3.3 mmol) 33%. Purity according to 1 FI-NMR approx. 95%.
  • the compounds according to the invention can also be processed from solution and lead there to process-technically simpler OLEDs, compared to the vacuum-processed OLEDs, but with 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 (for example 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 Electron transport layer (40 nm) / cathode together.
  • substrates from Technoprint silicon
  • 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 SS from CleviosTM) is also applied in the clean room by spin coating.
  • the required spin rate depends on the degree of dilution and the specific spin coater geometry.
  • the substrates are baked on a hot plate at 200 ° C. for 30 minutes.
  • the interlayer used serves that
  • the interlayer can be replaced by one or more layers, which only have to meet the condition by which downstream processing step of the EML deposition from solution not to be detached again.
  • the triplet emitters according to the invention are used together with the
  • the 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
  • the solution-processed devices contain an emission layer made of Matrix1: Matrix2: lr (L) with the specified percentages.
  • the emission layer is spun on in an inert gas atmosphere, in the present case argon, and baked at 160 ° C. for 10 minutes.
  • the hole blocking layer (10nm RETM1) and the electron transport layer (40nm RETM1 (50%) / RETM2 (50%)) are vapor-deposited (vapor deposition systems from Lesker or the like, typical vapor pressure 5 x 10 -6 mbar).
  • a cathode made of aluminum (100 nm) high-purity metal from Aldrich) is evaporated.
  • the service life LD50 is defined as the time after which the luminance in operation with a starting brightness of 1000 cd / m 2 to 50% of the

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EP19805570.9A 2018-11-14 2019-11-12 Zur herstellung einer organischen elektronischen vorrichtung einsetzbare verbindungen Pending EP3880657A1 (de)

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CN113015720A (zh) 2021-06-22

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