EP3877369A1 - Composés pouvant être utilisés dans un dispositif électronique organique - Google Patents

Composés pouvant être utilisés dans un dispositif électronique organique

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Publication number
EP3877369A1
EP3877369A1 EP19800959.9A EP19800959A EP3877369A1 EP 3877369 A1 EP3877369 A1 EP 3877369A1 EP 19800959 A EP19800959 A EP 19800959A EP 3877369 A1 EP3877369 A1 EP 3877369A1
Authority
EP
European Patent Office
Prior art keywords
radicals
group
aromatic
atoms
substituted
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
EP19800959.9A
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German (de)
English (en)
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
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Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP3877369A1 publication Critical patent/EP3877369A1/fr
Pending legal-status Critical Current

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    • 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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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • 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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    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • connections 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
  • the structure of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461,
  • Organic electroluminescent devices are also known which comprise fluorescent emitters or emitters which show TADF (thermally activated delayed fluorescence). The properties of 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
  • Matrix materials, electron transport materials, hole transport materials, phosphorescent emitters, fluorescent emitters or emitters that show TADF (thermally activated delayed fluorescence) are not described in these documents.
  • TADF thermally activated delayed fluorescence
  • 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 suitable as fluorescent emitters or emitters which show TADF (thermally activated delayed fluorescence) and which lead to good device properties when used in this device, as well as the provision of the corresponding electronic device.
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic
  • 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.
  • Electrodes that have excellent color purity. Furthermore, 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.
  • Another task can be seen in electronic
  • 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 a compound which can be used as an active compound in an organic electronic device, the compound preferably being a purely organic compound, characterized in that the compound comprises at least one structure of the formula (I), preferably the compound has the formula mentioned
  • l is an integer ranging from 1 to 8, preferably 2, 4, 6 or 8;
  • Ring atoms which can each be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, by one or more R 2 radicals can be substituted, or an aralkyl or
  • Ring system with 5 to 40 aromatic ring atoms which can be substituted in each case by one or more radicals R 3 , or an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 3 , or a combination thereof Systems; two or more, preferably adjacent, substituents R 2 can be one with the other
  • 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 H atoms can be replaced by D, F, Cl, 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.
  • Active compounds are generally the organic or inorganic materials which are introduced, for example, in an organic electronic device, in particular in an organic electroluminescent device 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.
  • the compound that can be used as an active compound in an organic electronic device is preferably a purely organic compound.
  • a purely organic compound is a compound that is not related to a metal atom, i.e. neither
  • Metal atom forms a coordination compound, still with one
  • Metal atom forms a covalent bond.
  • a purely organic compound preferably does not comprise a metal atom which is in
  • Phosphorescence emitters are used. These metals, such as copper, molybdenum, etc. in particular rhenium, ruthenium, osmium, rhodium, iridium, palladium, are described in detail later.
  • the compound which can be used as an active compound in an organic electronic device can preferably be selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which show TADF (thermally activated delayed fluorescence), host materials, electron transport materials,
  • Exciton blocking materials electron injection materials, Hole conductor materials, hole injection materials, n-dopants, p-dopants, wide-band gap materials, electron blocking materials and / or hole blocking materials.
  • fluorescent emitters emitters that show TADF (thermally activated delayed fluorescence)
  • host materials electron transport materials, exciton blocking materials, electron injection materials, hole conductor materials, hole injection materials, n-dopants, p-dopants, wide band gap materials, electron blocking materials and / or hole blocking materials are preferred.
  • the inventive TADF thermally activated delayed fluorescence
  • Compound comprises at least one structure of the formula (II),
  • the compound preferably has the formula mentioned
  • radical R is the one mentioned above, in particular for formula (I)
  • adjacent carbon atoms are carbon atoms which are directly linked to one another.
  • adjacent residues in the definition of the residues means that these residues are bonded to the same carbon atom or to adjacent carbon atoms.
  • 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
  • Heteroatoms may or may not contain. If two or more, preferably adjacent radicals R, R 1 , R 2 and / or R 3 together form a ring system, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system can result.
  • an aryl group contains 6 to 60 C atoms, preferably 6 to 40 C atoms, particularly preferably 6 to 30 C atoms;
  • a heteroaryl group in the sense of this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, particularly preferably 2 to 30 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 results.
  • the heteroatoms are preferably selected from N, O and / or S.
  • an aryl group or heteroaryl group either a simple aromatic cycle, 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.
  • a cyclic alkyl, alkoxy or thioalkoxy group in the sense of this invention means a monocyclic, a bicyclic or a polycyclic group.
  • 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.
  • a C 1 - to C 40 -alkoxy group vitellinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinsky
  • 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,
  • connections are preferred which have point symmetry. Furthermore, connections are preferred which have axis symmetry.
  • the compounds according to the invention can preferably comprise at least one structure of the formulas (IIIa), (IIIb) or (IIIc); the compound preferably has the formulas mentioned
  • Compound comprises at least one structure of the formulas (IVa), (IVb) and / or (IVc), the compound preferably has the formulas mentioned
  • R a has the meaning given above, in particular for formula (II).
  • at least two of the radicals R a in the structures of the formulas (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or ( V) are the same, preferably all radicals R a are the same.
  • at least two of the radicals R a in the structures of the formulas (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) are different.
  • At least one of the radicals R and / or R a is preferably selected from the group of the 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. It can further be provided that at least one of the radicals R and / or R a is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched
  • substituents R and / or R a are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar) 2 , a straight-chain alkyl group having 1 to 8 C atoms, preferably having 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, which can each 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 preferably with 6 to 13 aromatic ring atoms, each can be substituted by one or more non-aromatic radicals R 1 , but is preferably unsubstituted; optionally two substituents R 1 , preferably those on adjacent
  • 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 can have the meaning set out above.
  • the substituents R are particularly preferably selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each of which is substituted by 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 a 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 1 , but preferred
  • R a is unsubstituted.
  • suitable substituents R a 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 and / or R a of the cuban structure according to the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) with one another do not form a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system. This includes the formation of a condensed one
  • the compound which can be used as an active compound in an organic electronic device comprises a hole transport group, preferably at least one of the groups R and / or R a having a structure according to the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) comprises a hole transport group, preferably represents.
  • Hole transport groups are known in the art, these
  • 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 symbols Ar 1 and R 1 have the meaning given above, in particular for formula (I).
  • the presence of an NN bond is preferably excluded here.
  • the hole transport group comprises a group, preferably stands for a group which is selected from the formulas (H-4) to (H-26),
  • 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 substituted by one or more radicals R 1 may be, but is preferably unsubstituted, where R 1 is the same as above,
  • Ar 2 which is set out in formulas (H-1) to (H-26), is also preferably an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is 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. 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. It can further be provided that the group Ar 2, which is set out in formulas (H-1) to (H-26), among other things, at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one
  • 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 may have the meaning shown above, in particular in formula (I).
  • the compound which can be used as an active compound in an organic electronic device comprises a radical comprising an electron transport group, preferably at least one of the groups R and / or R a having a structure according to the formulas ( I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) a radical comprising an electron transport group, preferably represents.
  • Electron transport groups are well known in the art and promote the ability of compounds to transport and / or conduct electrons. Furthermore, compounds which can be used as an active compound in an organic electronic device have surprising advantages which comprise at least one structure selected from the group consisting of pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, quinoxalines, quinolines, isoquinolines, imidazoles and / or benzimidazoles is selected, with pyrimidines, triazines and quinazolines being particularly preferred. These structures generally promote the ability of compounds to transport and / or conduct electrons. In a preferred embodiment of the present invention it can be provided that 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 may be substituted by one or more radicals R 1
  • Q is an electron transport group, where R 1 is the previously has in particular the meaning given 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
  • R 1 may have the meaning given above, in particular for formula (I).
  • 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).
  • the symbol L 1 which is set out, inter alia, in formula (QL), preferably identically or differently, represents a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms on each occurrence,
  • 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.
  • 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, which can each be substituted by one or more radicals R 1 , 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 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.
  • 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 ' represents the same or different at each occurrence CR 1 or N, and Q''represents NR 1 , O or S;
  • R 1 is as previously defined, in particular in formula (I).
  • 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)
  • R 1 has the meaning set out above for formula (I)
  • the dashed bond marks the attachment position and m 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n 0, 1, 2 or 3, preferably 0, 1 or 2 and o is 0, 1 or 2, preferably 1 or 2.
  • the structures of the formulas (Q-16), (Q-17), (Q-18) and (Q-19) are preferred.
  • the group Q or the group set forth in the formula (QL), inter alia, can
  • Electron transport group can be selected from structures of the formulas (Q-23), (Q-24) and / or (Q-25),
  • the symbol R 1 has the meaning previously given, inter alia, for formula (I) and the dashed bond marks the attachment position.
  • the group Q or the electron transport group set out, inter alia, in the formula (QL) can be selected from structures of the formulas (Q-26), (Q-27), (Q-28), (Q-29 ) and / or (Q-30), where symbols Ar 1 and R 1 have the meanings given above for formula (I) bis, X 'is N or CR 1 and the dashed bond marks the attachment position.
  • the group Q set out in the formula (QL) or the electron transport group can 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), wherein the symbols Ar 1 and R 1 have the meaning set out above for formula (I), the dashed bond
  • Ar 1 is the same or different in each occurrence for an aromatic or heteroaromatic ring system, preferably an aryl or
  • Heteroaryl radical with 5 to 24 aromatic ring atoms preferably with 6 to 18 aromatic ring atoms, particularly preferably for an aromatic ring system, preferably an aryl radical with 6 to 12 aromatic ring atoms or a heteroaromatic ring system, preferably a heteroaryl group with 5 to 13 aromatic ring atoms, each 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).
  • the symbol Ar 1 preferably represents an aryl or heteroaryl radical, so that an aromatic or heteroaromatic group
  • Ar 1 in the formulas (H-1) to (H-26) or (Q-26) to (Q-44) advantageously represents an aromatic ring system with 6 to 12 aromatic ring atoms, which contains one or more radicals R 2 may be substituted, but is preferably unsubstituted, where R 2 may have the meaning given above, in particular for formula (I).
  • the radicals R 1 or R 2 in the formulas (H-1) to (H-26) or (Q-1) to (Q-44) preferably form with the ring atoms of the aryl group or
  • 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,
  • Formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) each comprise, preferably represent, a hole transport group, preferably two radicals R a each comprise a hole transport group, preferably represent. It can further be provided that at least one of the radicals R and / or R a has a structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) comprises two hole transport groups.
  • a hole transport group can be regarded as the radical R 1 , in which case the substituents R 1 set out in the structures of the formulas (H-1) to (H-26) are to be replaced by radicals R 2 .
  • R 1 substituents R 1 set out in the structures of the formulas (H-1) to (H-26) are to be replaced by radicals R 2 .
  • R 2 radicals R 1 .
  • Formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) each comprise a radical comprising an electron transport group
  • radicals R and / or R a preferably represent, preferably two radicals R a each Include electron transport group-comprising rest, preferably represent. It can further be provided that at least one of the radicals R and / or R a has a structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) two residues comprising electron transport groups.
  • a radical comprising an electron transport group can be regarded as radical R 1 , in which case those set out in the structures of the formulas (Q-1) to (Q-44)
  • Substituents R 1 are to be replaced by radicals R 2 .
  • at least one of the radicals R and / or R a has a structure according to the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), ( IVb), (IVc) and / or (v) a hole-transport group comprising, preferably represents, and at least one of the radicals R and / or R comprises a an electron transport group-comprising radical, preferably represents, with preferably one of R a is a
  • Hole transport group comprises, preferably represents, and at least one of the radicals R a comprises an electron transport group-comprising radical, preferably represents. It can further be provided that at least one of the radicals R and / or R a has a structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) both comprise a radical comprising an electron transport group and a hole transport group.
  • Hole transport group can be regarded as the radical R 1 , in which case the substituents R 1 set out in the structures of the formulas (Q-1) to (Q-44) or (H-1) to (H-26) are represented by radicals R 2 are replacing.
  • at least one of the radicals R and / or R a comprises at least one group which 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 Compounds have corresponding groups. Wide band gap materials will be discussed in more detail later.
  • at least one of the radicals R and / or R a comprises at least one group which leads to materials which are used as host material.
  • 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
  • At least one of the radicals R and / or R a preferably comprises in structures of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) at least one aromatic or heteroaromatic ring system with two, preferably with three fused aromatic or heteroaromatic rings. It can preferably be provided that the aromatic or
  • heteroaromatic ring system with two, preferably with three fused aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar-1) to (Ar-11)
  • 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 is preferably Sum of the indices p, e, i, j, h and m in the structures of the formulas (Ar'-1) to (Ar'-11) in each case at most 3,
  • H atoms can be replaced by D or F, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which can be substituted with one or more radicals R 2 , but is preferably unsubstituted, or an aralkyl or heteroar alkyl group with 5 to 25 aromatic ring atoms, which may be substituted with one or more radicals R 2 ; optionally two substituents R 1 , which are preferably bonded to adjacent carbon atoms, can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which is linked to a or more radicals R 1 can be substituted, the group Ar 1 having the meaning given above, in particular for formula (I).
  • substituents R 1 are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar 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, each with one or more non-aromatic radicals R 1 can be substituted, 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. It can further be provided that the substituents R 1 are one
  • 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 .
  • At least one Radical R 1 or Ar 1 represents a group which is selected from the formulas (R 1 - 1) to (R 1 - 92), or in a structure of the formulas (H-1) to (H-26), ( QL), (Q-1) to (Q-44), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) at least one radical Ar 1 or R 1 stands for 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), and
  • 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 .
  • the radicals R 2 in the formulas (R 1 -1) to (R 1 -92) together with the ring atoms of the aryl group or heteroaryl group to which the radicals R 2 are bonded do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system . This includes the formation of a condensed ring system with possible substituents R 3 , which may be attached to the radicals R 2 .
  • 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 of these formulas, in which case the groups R 2 set out in the formulas (R 1 -1) to (R 1 -92) are to be replaced by radicals R 1 .
  • the preferences set out above with regard to formulas (R 1 -1) to (R 1 -92) apply accordingly.
  • the compound comprises 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 transport group is connected to further structural elements via a connecting group which is selected from the formulas (L 1 -1) to ( L 1 -108) or the radical L 1 in formulas (QL), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents a group which is selected is from the formulas (L 1 -1) to (L 1 -108),
  • Formula (L 1 -106) Formula (L 1 -107) Formula (L 1 -108) where the dashed bonds each mark the attachment positions, the index k is 0 or 1, the index l is 0, 1 or 2, the index j is independently 0, 1, 2 or 3 on each occurrence; the index h is independently 0, 1, 2, 3 or 4 on each occurrence, 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; and the symbol R 1 has the meaning given above, in particular for formula (I). It can preferably be provided that the sum of the indices k, l, g, h and j in the structures of the formulas (L 1 -1) to (L 1 -108) in each case at most 3,
  • 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, l, 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, l, 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 with a group of the formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) 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, l, 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.
  • the radicals R 2 in the formulas (L 1 -1) to (L 1 -108) preferably do not form a condensed aromatic or heteroaromatic with the ring atoms of the aryl group or heteroaryl group to which the radicals R 2 are bonded Ring system, preferably no condensed ring system.
  • Compounds which can be used as an active compound in an organic electronic device preferably compounds comprising structures of the formulas (I), (II), (IIIa) to (IIIc), (IVa) to (IVc) and / or (V ), 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 on.
  • preferred compounds according to the invention are distinguished in that they can be sublimed. These compounds generally have a molecular weight of less than about 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 condensed directly to one another and 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
  • R 2 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, which is replaced by 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 is , for example in the case of a structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) and 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 with 1 to 10 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24
  • aromatic ring atoms particularly preferably having 5 to 13 aromatic ring atoms, which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.
  • Compounds according to the invention having structures of the formula (II) are particularly preferred, the index m being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and the index l being an integer in the range 1 to 8, which have the following characteristics:
  • n an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • both radicals R a are the same.
  • Structures of the formulas (IIIa) and (IIIb) are preferred, structures of the formulas (IIIb) being particularly preferred.
  • Compounds according to the invention having structures of the formulas (IVa), (IVb) or (IVc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • all radicals R a are the same.
  • Compounds according to the invention having structures of the formula (II) are particularly preferred, the index m being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and the index l being an integer in the range 1 to 8, which have the following characteristics:
  • index m being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and the index l being an integer in the range 1 to 8, which have the following characteristics:
  • index m being an integer in the range from 0 to 4
  • index l is an integer in the range 1 to 8, which have the following properties:
  • index m being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and the index l being an integer in the range 1 to 8, which have the following characteristics:
  • both radicals R a are the same.
  • Structures of the formulas (IIIa) and (IIIb) are preferred, structures of the formulas (IIIb) being particularly preferred.
  • Compounds according to the invention with structures of the formulas (IIIa), (IIIb) or (IIIc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • both radicals R a are the same. Structures of the formulas (IIIa) and (IIIb) are preferred, structures of the formulas (IIIb) being particularly preferred. Compounds according to the invention having structures of the formulas (IIIa), (IIIb) or (IIIc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and having the following properties :
  • both radicals R a are the same. Structures of the formulas (IIIa) and (IIIb) are preferred, structures of the formulas (IIIb) being particularly preferred. Compounds according to the invention having structures of the formulas (IIIa), (IIIb) or (IIIc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0 and having the following properties :
  • both radicals R a are the same.
  • Structures of the formulas (IIIa) and (IIIb) are preferred, structures of the formulas (IIIb) being particularly preferred.
  • Compounds according to the invention having structures of the formulas (IVa), (IVb) or (IVc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • all four radicals R a are the same. Structures of the formulas (IVa) and (IVb) are preferred, structures of the formulas (IVa) being particularly preferred. Compounds according to the invention having structures of the formulas (IVa), (IVb) or (IVc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • all four radicals R a are the same. Structures of the formulas (IVa) and (IVb) are preferred, structures of the formulas (IVa) being particularly preferred. Compounds according to the invention having structures of the formulas (IVa), (IVb) or (IVc) are furthermore particularly preferred, the index n being an integer in the range from 0 to 4, preferably 0 to 2 and particularly preferably 0, which have the following properties :
  • all four radicals R a are the same. Structures of the formulas (IVa) and (IVb) are preferred, structures of the formulas (IVa) being particularly preferred. Compounds according to the invention having structures of the formulas (IVa), (IVb) or (IVc) are furthermore particularly preferred, where the index n is a integer in the range from 0 to 4, preferably 0 to 2 and especially
  • all radicals R a are the same. It can further be provided that the compound which can be used as an active compound in an organic electronic device is not in direct contact with a metal atom,
  • ligand for a metal complex preferably does not represent a ligand for a metal complex.
  • suitable compounds according to the invention are the structures shown below according to the following formulas 1 to 23:
  • the present invention therefore furthermore relates to a process for the preparation of the compounds according to the invention, preferably compounds comprising structures of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V), in which, in a coupling reaction, a compound comprising at least one non-aromatic or non-heteroaromatic multicyclic ring system having a cubane structure is linked to a compound comprising at least one aromatic or heteroaromatic group.
  • Suitable compounds comprising at least one non-aromatic or non-heteroaromatic multicyclic ring system with a cubane structure can in many cases be obtained commercially, the starting compounds set out in the examples being obtainable by known processes, so that reference is made to them. These compounds can be reacted with further compounds, comprising at least one aromatic or heteroaromatic group, by known coupling reactions, the necessary conditions for this being known to the person skilled in the art and detailed
  • 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
  • the compounds for example in toluene or xylene at room temperature, are soluble in sufficient concentration to be able to process the compounds from solution. These soluble compounds are particularly suitable for processing from solution, for example by printing processes.
  • the compounds according to the invention comprising at least one structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) 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
  • Cyclobutylphenyl, vinyl and alkenyl are particularly preferred.
  • 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.
  • 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
  • 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 of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) 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 (e.g. according to EP 842208 or WO 2000/022026), spirobifluorenes (e.g.
  • EP 707020 EP 894107 or WO 2006/061181
  • para phenylenes e.g. according to WO 92/18552
  • carbazoles e.g. according to WO 2004/070772 or WO 2004/113468
  • thiophenes e.g. according to EP 1028136
  • dihydrophenanthrenes e.g. according to WO 2005/014689
  • cis and trans indenofluorene e.g. according to WO 2004/041901 or WO 2004/113412
  • ketones e.g. according to WO 2005/040302
  • phenanthrenes e.g. . 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 triarylamines, and / or electron transport units.
  • the cuban structure shown in formula (I) can be the core of an oligomer, polymer and / or dendrimer.
  • the radical R and / or Ra can be part of an oligomeric, polymeric or dendrimeric structure.
  • linear structural elements can be formed. Structures of the formulas (IVa), (IVb), (IVc) and / or (V) can give rise to branches which, depending on the design, can cause networking.
  • Device can be used as an active connection, preferred
  • 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-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-) - Fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4- Dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenz
  • 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 structures of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), ( IVc) and / or (V) or those before and after
  • 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 structure of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), ( IVb), (IVc) and / or (V) or the preferred embodiments described above and below, and at least one wide-band gap material, with wide-band gap material being a material in the sense of the disclosure of US Pat. No. 7,294,849 is understood.
  • 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 caused by the Energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) can be calculated.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • LUMO (eV) ((LEh * 27.212) -2.0041) /1.385
  • these values are to be regarded as HOMO or LUMO energy levels of the materials.
  • the lowest triplet state T 1 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 S 1 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 structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or ( V) or the preferred embodiments described above and below, and at least one phosphorescent emitter, the term phosphorescent emitter also being understood to mean phosphorescent dopants.
  • a dopant is understood to mean that component whose proportion in the mixture is the smaller one.
  • 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, preferably mixed-matrix systems are the preferred phosphorescent dopants given below.
  • the term phosphorescent dopants are typical
  • Compounds comprises in which the light emission takes place through a spin-prohibited transition, for example a transition from an 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 Contain atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number.
  • Preferred phosphorescence emitters are compounds which contain copper, molybdenum, tungsten, rhenium,
  • An electronic device is understood to mean a device which contains the anode, cathode and at least one layer located between the anode and cathode, 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 electroluminescent devices OLEDs, PLEDs, in particular phosphorescent OLEDs, containing at least a layer of at least one compound comprising structures of the formula (I).
  • OLEDs organic laser diodes
  • organic plasmon emitting devices DM Koller et al., Nature Photonics 2008, 1-4
  • OLEDs organic electroluminescent devices
  • Active components 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 emission materials 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 other layers, for example each have 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 MoO 3 or WO 3, or with (per) fluorinated ones
  • 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 structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb) , (IVc) and / or (V) or the preferred embodiments listed above as matrix material, preferably as electron-conducting matrix material in one or several emitting layers, preferably in combination with a further matrix material, preferably a hole-conducting matrix material.
  • the further matrix material is an electron-transporting compound.
  • the further matrix material is a compound with a large band gap, which is not or not significantly involved in the hole and electron transport in the layer.
  • An emissive layer comprises at least one emissive compound.
  • an organic electroluminescent device comprises the compound according to the invention, preferably a compound comprising structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) or the preferred embodiments listed above in a hole-conducting layer or an electron-conducting layer.
  • Suitable matrix materials which, in combination with the compounds of the formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) or
  • aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones e.g.
  • WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 2008/086851 disclosed carbazole derivatives, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, for. B. according to WO 2010/136109 and WO 2011/000455, aza-carbazole derivatives, for. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, e.g. B. according
  • WO 2007/137725 silanes, e.g. 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, for. B. according to EP 652273 or WO 2009/062578, diazasilol or tetraazasilol derivatives, e.g. B. according to WO 2010/054729, diazaphosphol derivatives, for. B. according to WO 2010/054730, bridged carbazole derivatives, for. B. according to US 2009/0136779, WO 2010/050778, WO
  • phosphorescent emitter which emits shorter waves than the actual emitter, can 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. It can also be preferred to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. The use of a mixture of a is also preferred
  • 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. It is further preferred to use a mixture of two or more triplet emitters together with a matrix.
  • the 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 comprising structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) is particularly preferred in a preferred Embodiment can be used as a matrix material in an emission layer of an organic electronic device, in particular in an organic electroluminescent device, for example in an OLED or OLEC.
  • Matrix material containing compound comprising structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) or those before and after executed preferred embodiments in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.
  • 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. Accordingly, 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 structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V ) or the preferred embodiments explained above and below are used as a component of mixed matrix systems.
  • the mixed matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials.
  • one of the two materials is a material with hole-transporting properties and the other material is a material with electron
  • the desired electron-transporting and hole-transporting properties of the mixed matrix components can, however, 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.
  • 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 such as, for example, alkaline earth metals, alkali metals, main group metals or lanthanoids (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.
  • other metals can also be used 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, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.).
  • Organic alkali metal complexes in question 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 as a hole injection layer to the anode, metal oxides, for example MoO 3 or WO 3 , or (per) fluorinated electron-deficient aromatics being suitable as p-dopants.
  • metal oxides for example MoO 3 or WO 3
  • fluorinated electron-deficient aromatics being suitable as p-dopants.
  • 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.
  • all materials can be used in the further layers, as are used for the layers according to the prior art, and the person skilled in the art can combine each of these materials with the materials according to the invention in an electronic device without inventive step.
  • 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 are 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
  • 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 containing a compound according to the invention comprising structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa), (IVb), (IVc) and / or (V) and apply a matrix material from solution and then a hole blocking layer and / or an electron transport layer in a vacuum evaporate.
  • organic electroluminescent devices containing compounds according to the invention comprising structures according to formulas (I), (II), (IIIa), (IIIb), (IIIc), (IVa) , (IVb), (IVc) and / or (V) or those listed above
  • the electronic devices according to the invention are distinguished by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic ones
  • Electron transport materials, hole conductor materials and / or as host materials have excellent efficiency.
  • the efficiency is significantly higher compared to analog compounds that do not contain a Cuban structure.
  • the compounds, oligomers, polymers or Dendrimers, which can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below are minor
  • 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 as electron transport materials are provided.
  • Hole conductor materials and / or as host materials have excellent color purity. 4.
  • 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
  • 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 fluorescent emitter, emitter which shows 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 fluorescent emitter (singlet 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. The preferences set out above for the connection also apply to the electronic devices.
  • 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-laser
  • organic plasmon emitting devices OLEDs, PLEDs
  • OLEDs 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
  • Tripotassium phosphate monohydrate 1.15 g (1 mmol) of tetrakis-triphenylphosphino-palladium (0), 50 g of glass balls (3 mm in diameter) and 150 ml of DMSO are heated to 120 ° C. for 24 h. After cooling to 60 ° C, the reaction mixture is poured into 300 ml of a water-methanol mixture (1: 1, vv), stirred for 30 min. after, the raw product is suctioned off and washed three times with 30 ml of methanol each. The crude product is dissolved in 200 ml DCM, the solution is filtered over a silica gel bed slurried with DCM.
  • O-3-BRSE-Ph-C and O-4-BRSE-Ph-C can be reacted with mono-bromo-functionalized oligo-phenylenes, fluorene, carbazole, dibenzofuran or mixtures thereof.
  • the cleaning is done by falling the crude product from DCM into methanol or by
  • Solution-processed devices A: From low-molecular soluble functional materials The materials according to the invention can be processed from solution. 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).
  • PLEDs polymer light-emitting diodes
  • the structure consists of substrate / ITO / hole injection layer (60 nm) / interlayer (20 nm) /
  • substrates from Technoprint are used, on which the ITO structure (indium tin oxide, a transparent, conductive anode) is applied.
  • the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by UV / ozone plasma treatment.
  • a 20 nm hole injection layer is also applied in the clean room by spin coating (PEDOT: PSS from Clevios TM ).
  • the required spin rate depends on the degree of dilution and the specific spin coater geometry.
  • the substrates are baked on a hot plate at 200 ° C. for 30 minutes.
  • the interlayer used is for hole transport, in this case HL-X from Merck is used.
  • the interlayer can also be replaced by one or more layers, which only have to meet the condition of the downstream one
  • the triplet emitters according to the invention are dissolved together with the matrix materials in toluene or chlorobenzene.
  • the typical solids content of such solutions is between 16 and 25 g / L if, as here, the typical layer thickness of 60 nm for a device is to be achieved by means of spin coating.
  • the solution-processed devices contain an emission layer made of Material1: Material2: Material3: Emitter (weight percentages see Table1).
  • the emission layer is spun on in an inert gas atmosphere, in the present case argon, and baked at 160 ° C. for 30 minutes.
  • the hole blocking layer (10 nm ETM1) and the electron transport layer (40 nm ETM1 (50%) / ETM2 (50%)) are evaporated on top
  • the OLED examples mentioned have not yet been optimized; Table 1 summarizes the data obtained.
  • the service life LD50 is defined as the time after which the luminance drops to 50% of the starting luminance during operation with a starting brightness of 1000 cd / m2.
  • ITO Indium tin oxide
  • HTL hole transport layer
  • EML emission layer
  • HBL Lock blocking layer
  • ETL electron transport layer
  • substrates from Technoprint are used, to which the ITO structure (indium tin oxide, a transparent, conductive anode) is applied.
  • the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by UV / ozone plasma treatment.
  • an 80 nm hole injection layer PEDOT-PSS (commercially available from Heraeus GmbH & Co.KG, Germany) 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 180 ° C. for 20 minutes. They serve as the hole transport layer
  • Compounds according to the invention optionally in combination with other hole conductor materials. They are applied from toluene solution, solids content typically approx. 7 g / l with a layer thickness of approx. 20 nm, by spin coating under an inert atmosphere (argon) and 60 min. baked at 220 ° C. To produce the emission layer, the triplet emitters are dissolved together with the matrix materials in toluene or chlorobenzene.
  • the typical solids content of such solutions is between 16 and 25 g / L, if, as here, the typical layer thickness of 60 nm for a device
  • the solution-processed triplet devices contain an emission layer made of Material1: Material2: Material3: Emitter (weight percentages see Table1).
  • the emission layer is spun on in an inert gas atmosphere, in the present case argon, and baked at 160 ° C. for 20 minutes.
  • the hole blocking layer (10nm ETM1) and the electron transport layer (40nm ETM1 (50%) / ETM2 (50%)) are evaporated on top (Lesker vapor deposition systems, etc., more typically
  • the service life LD50 is the time after which the luminance in operation with a starting brightness of 1000 cd / m2 to 50% of the

Abstract

La présente invention concerne des composés pouvant être utilisés en tant que composé actif dans un dispositif électronique organique, en particulier pour une utilisation dans des dispositifs électroniques. L'invention concerne également un procédé de fabrication des composés selon l'invention, ainsi que des dispositifs électroniques les contenant.
EP19800959.9A 2018-11-05 2019-11-04 Composés pouvant être utilisés dans un dispositif électronique organique Pending EP3877369A1 (fr)

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JP7023946B2 (ja) 2016-10-13 2022-02-22 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 金属錯体
CN110785424B (zh) * 2017-05-04 2023-10-24 新泽西鲁特格斯州立大学 在分子晶体中结合了离子键和配位键的发光和可分散的杂化材料
EP3774769A1 (fr) * 2018-03-28 2021-02-17 Bayer Pharma Aktiengesellschaft Composés de 4-(3-amino-6-fluoro-1h-indazol-5-yl)-1,2,6-triméthyl-1,4-dihydropyridine-3,5-dicarbonitrile pour le traitement de troubles hyperprolifératifs

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US20210391538A1 (en) 2021-12-16
KR20210088629A (ko) 2021-07-14
JP2022506382A (ja) 2022-01-17
CN112955437A (zh) 2021-06-11
US11917906B2 (en) 2024-02-27

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