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WO2025051734A1 - Matériaux pour dispositifs électroluminescents organiques - Google Patents

Matériaux pour dispositifs électroluminescents organiques Download PDF

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Publication number
WO2025051734A1
WO2025051734A1 PCT/EP2024/074588 EP2024074588W WO2025051734A1 WO 2025051734 A1 WO2025051734 A1 WO 2025051734A1 EP 2024074588 W EP2024074588 W EP 2024074588W WO 2025051734 A1 WO2025051734 A1 WO 2025051734A1
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radicals
atoms
substituted
moiety
formula
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Amir Hossain Parham
Christian EICKHOFF
Sebastian Stolz
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Merck Patent GmbH
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Merck Patent GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to compounds containing at least one of indolocarbazole moiety Z', at least one of N-heteroaryl moiety Z h , and at least one of moiety Z* represented by Formula (1) and electronic devices containing these compounds, in particular organic electroluminescence devices containing these compounds as matrix materials, optionally in combination with another compound.
  • Phosphorescent organometallic complexes are often used in organic electroluminescent devices (OLEDs). In general, there is still room for improvement with OLEDs, for example with regard to efficiency, operating voltage and service life.
  • OLEDs organic electroluminescent devices
  • the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials, are also of particular importance here. Improvements in these materials can therefore also lead to significant improvements in the OLED properties.
  • WO18236092 A1 US 20160163995 AA and US 2023019297 AA describe the compound containing indolocarbazole group, N-heteroaryl group and dibenzofuran group as as matrix materials.
  • WO1 8198844 A1 and US2013248849 AA describes the compound containing indolocarbazole group, N-heteroaryl group and phenyl group as as matrix materials.
  • the problem addressed by the present invention is therefore providing a host material which is suitable for use in an electronic device, especially in a fluorescent or phosphorescent organic electroluminescent device, and which lead to good device properties, especially with regard to an improved lifetime, and providing the corresponding electronic device.
  • the advantages are especially also manifested in the presence of the combination of at least one compound containing at least one of indolocarbazole moiety Z', at least one of N-heteroaryl moiety Z h , and at least one of moiety Z* represented by Formula (1) as the first host material and further compound as the second host material, for example in combination with one or more compounds of the formulae (HH- 1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6).
  • the present invention therefore first provides a compound containing at least one of indolocarbazole moiety Z', at least one of N-heteroaryl moiety Z h , and at least one of moiety Z* represented by Formula (1): where the groups and indices that occur are as follows:
  • Y 11 is S or O
  • X 11 is CR 11 or N
  • X 12 is CR 12 or N
  • X 13 is CR 13 or N
  • X 14 is CR 14 or N
  • X 15 is CR 15 or N
  • X 16 is CR 16 or N
  • X 17 is CR 17 or N
  • X 18 is CR 18 or N
  • X 19 is CR 19 or N
  • X 19 is CR 19 or N
  • X 20 is CR 20 or N, wherein at least one of X 11 to X 20 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’;
  • Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case also be substituted by one or more radicals R'; and
  • R is the same or different at each instance and is H, D, F, Cl, Br, I, CN, a straightchain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms.
  • the invention further provides a mixture containing at least one compound containing at least one of indolocarbazole moiety Z', at least one of N-heteroaryl moiety Z h , and at least one of moiety Z* represented by Formula (1) as described above or hereinafter and at least one further compound and/or at least one solvent, wherein the further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, TADF (Thermally activated delayed fluorescence) emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, n-dopants, wide band gap materials, electron blocking materials and hole blocking materials.
  • fluorescent emitters phosphorescent emitters
  • TADF Thermally activated delayed fluorescence
  • D or "D-atom" in the context of this invention means deuterium.
  • Indolocarbazole moiety in the context of this invention means the moiety including an indolocarbazole group.
  • N-heteroaryl moiety in the context of this invention means the moiety including a heteroaryl group including at least one N atom as a ring formation atom.
  • An aryl group in the context of this invention contains 6 to 60 ring atoms, preferably carbon atoms.
  • a heteroaryl group in the context of this invention contains 5 to 60 ring atoms, where the ring atoms include carbon atoms and at least one heteroatom, with the proviso that the sum total of carbon atoms and heteroatoms adds up to at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aryl group or heteroaryl group is understood here to mean either a simple aromatic cycle, i.e.
  • phenyl derived from benzene, or a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a fused aryl or heteroaryl group, for example derived from naphthalene, anthracene, phenanthrene, quinoline or isoquinoline.
  • An aryl group having 6 to 18 carbon atoms is therefore preferably phenyl, naphthyl, phenanthryl or triphenylenyl, with no restriction in the attachment of the aryl group as substituent.
  • the aryl or heteroaryl group in the context of this invention may bear one or more R radicals, where the substituent R is described below.
  • An aromatic ring system in the context of this invention contains 6 to 60 ring atoms in the ring system.
  • the aromatic ring system also includes aryl groups as described above.
  • An aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and triphenylenyl.
  • a heteroaromatic ring system in the context of this invention contains 5 to 60 ring atoms and at least one heteroatom.
  • a preferred heteroaromatic ring system has 10 to 40 ring atoms and at least one heteroatom.
  • the heteroaromatic ring system also includes heteroaryl groups as described above.
  • the heteroatoms in the heteroaromatic ring system are preferably selected from N, O and/or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is understood to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which it is also possible for a plurality of aryl or heteroaryl groups to be interrupted by a nonaromatic unit (preferably less than 10% of the atoms other than H), for example a carbon, nitrogen or oxygen atom or a carbonyl group.
  • a nonaromatic unit preferably less than 10% of the atoms other than H
  • systems such as 9,9'- spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc.
  • aromatic or heteroaromatic ring systems in the context of this invention, and likewise systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group.
  • systems in which two or more aryl or heteroaryl groups are bonded directly to one another for example biphenyl, terphenyl, quaterphenyl or bipyridine, are likewise encompassed by the definition of the aromatic or heteroaromatic ring system.
  • An aromatic or heteroaromatic ring system which has 5 to 60 ring atoms and may be joined to the aromatic or heteroaromatic system via any desired positions is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- ortrans-indenofluorene, cis- ortrans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, trux
  • the abbreviation Ar at each instance is in each case independently an aromatic or heteroaromatic ring system having 5 to 60 ring atoms and may be substituted by one or more R' radicals, where the details for the aromatic ring system or heteroaromatic ring system apply here correspondingly.
  • the R’ radical or the R’ radicals has/have a definition as described above or described hereinafter.
  • Ar is preferably in each case independently an aryl group which has 6 to 40 ring atoms and may be substituted by one or more R’ radicals, or a heteroaryl group having 5 to 40 ring atoms and containing O or S as heteroatom, which may be substituted by one or more R’ radicals, where the details for the aryl group or heteroaryl group and R’ as described above or hereinafter are applicable correspondingly.
  • Ars is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 ring atoms and may be substituted by one or more nonaromatic R 7 radicals; at the same time, two Ars radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R 7 ), C(R 7 )2, O and S, where the R 7 radical or the substituents R 7 has/have a definition as described above or hereinafter.
  • Ars is an aryl group having 6 to 20 ring atoms as described above.
  • a cyclic alkyl, alkoxy or thioalkyl group in the context of this invention is understood to mean a monocyclic, bicyclic or polycyclic group.
  • a straight-chain alkyl group having 1 to 40 C atoms, branched or cyclic alkyl group having 3 to 40 C atoms is understood to mean, for example, the methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1 -methylcyclopentyl, 2-methylpentyl, n- heptyl, 2-heptyl,
  • a straight-chain alkoxy group having 1 to 40 C atoms or branched alkoxy group having 3 to 40 C atoms is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n- propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • a straight-chain thioalkyl group having 1 to 40 C atoms is understood to mean, for example, S-alkyl groups, for example thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n- propyl, 1-thio-i-butyl, 1-thio-n-butyl or 1 -thio-t-butyl.
  • An aryloxy or heteroaryloxy group having 5 to 60 ring atoms means O-aryl or O-heteroaryl and means that the aryl or heteroaryl group is bonded via an oxygen atom, where the aryl or heteroaryl group is defined as described above.
  • An aralkyl or heteroaralkyl group having 5 to 40 ring atoms means that an alkyl group as described above is substituted by an aryl group or heteroaryl group, where the aryl or heteroaryl group is defined as described above.
  • all X 11 to X 20 is not N.
  • the indolocarbazole moiety Z' is represented by Formula (2): Formula (2) Formula 2A wherein in Formula (2) and 2A, X 2a is CR 20a or C, X 2b is CR 20b or C, X 2c is CR 20c or C, and X 2d is CR 20d or C, X 2a and X 2b , X 2b and X 2c , and X 2c and X 2d are the same or different at each instance and are linked by a single bond or double bond, wherein X 2a and X 2b is C and X 2a --X 2b in Formula (2) is binding with the dotted line in Formula 2A, X 2b and X 2c is C and X 2b --X 2c in Formula (2) is binding with the dotted line in Formula 2A, or X 2c and X 2d is C and X 2c --X 2d in Formula (2) is binding with the dotted line
  • the indolocarbazole moiety Z i is represented by Formula 2-1: wherein in Formula 2-1, R 20c , R 20d , and R 21 to R 30 have the definition given above or given hereinafter.
  • R 21 and R 22 is a binding site to the moiety Z* represented by Formula (1) or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’.
  • the compound satisfies at least one of Conditions A and B:
  • At least one of X 11 to X 13 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’ ⁇ Condition B>
  • At least one of X 14 to X 17 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’.
  • the compound satisfies at least one of Conditions A-1 to A-3, B-1 and B-2, preferrably satisfies at least one of Conditions A-1 , A-2, A-3, and B-2, particularly preferrably satisfies at least one of Conditions A-1 and B-2, and very particularly preferrably satisfies Condition A-1 :
  • X 11 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’ ⁇ Condition A-2>
  • X 12 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’ ⁇ Condition A-3>
  • X 13 is not N and is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’ ⁇ Condition B-1 >
  • X 13 is not N and is a binding site to the indolocarbazole moiety Z' via linker *-(L n ) na -*’ ⁇ Condition 1-B-1 >
  • X 14 is not N and is a binding site to the indolocarbazole moiety Z' via linker *-(L n ) na -*’
  • X 15 is not N and is a binding site to the indolocarbazole moiety Z' via linker *-(L n ) na -*’ ⁇ Condition 2-A-1>
  • X 13 is not N and is a binding site to the N-heteroaryl moiety Z h via linker *-(L n ) na -*’
  • the compound satisfies only one of Conditions A-1 to A-3, B-1 and B-2. In one embodiment of the compound or preferred embodiments of the host material of the compound above, the compound satisfies only one of Conditions 1-A-1 to 1-A-3, 1-B-1 , 1- B-2, 2-A-1 to 2-A-3, 2-B-1 and 2-B-2.
  • At least one of N atoms in the indolocarbazole moiety Z' is a binding site to the N-heteroaryl moiety Z h or the moiety Z* represented by Formula (1).
  • one of N atoms in the indolocarbazole moiety Z' is a binding site to the N-heteroaryl moiety Z h or the moiety Z* represented by Formula (1).
  • one of N atoms in the indolocarbazole moiety Z' is a binding site to the N-heteroaryl moiety Z h and the other N atom in the indolocarbazole moiety Z' is a binding site to the moiety Z* represented by Formula (1).
  • N atoms in the indolocarbazole moiety Z' is a binding site to the N-heteroaryl moiety Z h via linker *-(L n ) na -*’ ⁇ Condition C-2>
  • the compound is partially deuterated or fully deuterated.
  • the indolocarbazole moiety Z' comprises at least one of deuterium.
  • the moiety Z* represented by Formula (1) comprises at least one of deuterium.
  • At least one of R 11 to R 20 in Formula (1) comprises at least one of deuterium, wherein at least one of R 11 to R 20 is a binding site to the indolocarbazole moiety Z' or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’.
  • At least one of R 20a , R 20b , R 20c , R 20d and R 21 to R 30 in Formula (2) and Formula 2A, or at least one of R 20c , R 20d , and R 21 to R 30 in Formula 2-1 comprises at least one of deuterium, wherein at least one of R 20a , R 20b , R 20c , R 20d and R 21 to R 30 is a binding site to the moiety Z‘ represented by Formula (1) or the N-heteroaryl moiety Z h via linker *- (L n ) na -*’.
  • At least one of R 31 to R 35 , L 1 to L 3 , Z‘ and Z' in Formula 1-1 or 1-2 comprises at least one of deuterium.
  • the degree of deuteration of the compound is about 1 mol% to 100 mol%, is preferably at least 10 mol% to 100 mol%, is particularly preferably 50 mol% to 95 mol% and is particularly preferably 70 mol% to 90 mol%.
  • R 21 and R 22 are identically or differently at each occurrence, aromatic ring systems having 6 to 40 ring atoms, heteroaromatic ring systems having 5 to 40 ring atoms or a binding site to the moiety Z* represented by Formula (1) or the N-heteroaryl moiety Z h via linker *-(L n ) na -*’.
  • the compounds according to the invention can be prepared by means of known synthesis methods, such as following methods.
  • the following synthesis schemes show the compounds used to simplify structures with a small number of substituents. This does not exclude the presence of any other substituents in the procedures.
  • Particularly suitable compounds of the formula (1) are the compounds E1 to E24 of table o
  • the compounds of the invention can be prepared by synthesis steps known to those skilled in the art, for example bromination, Suzuki coupling, Ullmann coupling, Hartwig- Buchwald coupling, etc.
  • R 1 corresponds to R 11 to R 20
  • R 2 corresponds to R 20a , R 20b , R 20c , R 20d and R 21 to R 30
  • R 3 corresponds to R 31 to R 35
  • X corresponds to a halogen atom in Schemes 1 and 2
  • formulations of the compounds of the invention or of mixtures of compounds of the invention with further functional materials such as matrix materials, fluorescent emitters, phosphorescent emitters and/or emitters that exhibit TADF, are required.
  • These formulations may, for example, be solutions, dispersions or emulsions.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1, 2,3,5- tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2- methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4- methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decal
  • inventive compounds (optionally the compounds of formulae 1-1 or 1-2) as described above or described as preferred, are suitable for use in an organic electroluminescent device, especially as matrix material.
  • the compound of the invention When the compound of the invention is used as matrix material or, synonymously, host material in an emitting layer, it is preferably used in combination with a further compound.
  • the invention therefore further provides a mixture containing at least one inventive compound or at least one preferred compound of the formulae 1-1 or 1-2 as defined, or a compound from table 1 or one of compounds E1 to E24 and at least one further compound selected from the group of the matrix materials, phosphorescent emitters, fluorescent emitters and/or emitters that exhibit TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture of the invention are described hereinafter.
  • the present invention likewise further provides a formulation containing at least one compound of the invention, as described above, or a mixture of the invention, as described above, and at least one solvent.
  • the solvent may be an abovementioned solvent or a mixture of these solvents.
  • the present invention further provides an organic electronic device containing an anode, a cathode and at least one organic layer, containing at least one inventive compound or at least one preferred compound of the formulae 1-1 or 1-2 as defined, or a compound from table 1 or one of compounds E1 to E24.
  • the organic electronic device may be selected, for example, from organic integrated circuits (OlCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors.
  • OlCs organic integrated circuits
  • OFETs organic field-effect transistors
  • OTFTs organic thin-film transistors
  • O electroluminescent devices organic electroluminescent devices
  • organic solar cells (OSCs) organic solar cells
  • organic optical detectors organic photoreceptors.
  • the organic electronic device is preferably an organic electroluminescent device.
  • the organic electroluminescent device (synonymous with organic electroluminescence device) of the invention is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC, LEC, LEEC), an organic laser diode (O-laser) or an organic light-emitting diode (OLED).
  • OLET organic light-emitting transistor
  • OFQD organic field quench device
  • OLED organic light-emitting electrochemical cell
  • O-laser organic laser diode
  • OLED organic light-emitting diode
  • the organic electroluminescent device of the invention is especially an organic lightemitting diode or an organic light-emitting electrochemical cell.
  • the device of the invention is more preferably an OLED.
  • the organic layer of the device of the invention preferably comprises, as well as a lightemitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocker layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocker layer, an electron blocker layer and/or charge generation layers.
  • EML lightemitting layer
  • HIL hole injection layer
  • HTL hole transport layer
  • HBL hole blocker layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an exciton blocker layer an electron blocker layer and/or charge generation layers.
  • the device of the invention to include two or more layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL and HBL.
  • interlayers having an exciton-blocking function for example, to be introduced between two emitting layers.
  • a plurality of emission layers are present, these preferably have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce are used in the emitting layers. It is also possible for two or more fluorescent and/or phosphorescent compounds to be present in an emitting layer. Especially preferred are systems having three emitting layers, where the three layers show blue, green and orange or red emission. As an alternative to the combination as described above, an emitting layer may also show yellow emission. Combinations of this kind are known to those skilled in the art.
  • the organic electroluminescent device of the invention may also be a tandem electroluminescent device, especially for white-emitting OLEDs.
  • the device may also comprise inorganic materials or else layers formed entirely from inorganic materials.
  • inventive compound as described above or as described as preferred can be used in different layers, according to the exact structure. Preference is given to an organic electroluminescent device containing the inventive compound or the above-recited preferred embodiments in an emitting layer as matrix material for fluorescent emitters, phosphorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), especially for phosphorescent emitters.
  • the compound of the invention can also be used in an electron transport layer and/or in a hole transport layer and/or in an exciton blocker layer and/or in a hole blocker layer. Particular preference is given to using the compound of the invention as matrix material in an emitting layer or as electron transport material or hole blocker material in an electron transport layer or hole blocker layer.
  • the present invention further provides an organic electronic device as described above, wherein the organic layer comprises at least one light-emitting layer containing at least one inventive compound or at least one preferred compound of the formulae 1-1 or 1-2 as defined, or a compound from table 1 or one of compounds E1 to E24.
  • At least one further matrix material is selected in the light-emitting layer, and this is used together with inventive compounds as described above or described as preferred or with the compounds from table 1 or the compounds E1 to E24.
  • the present invention accordingly further provides an organic electronic device as described above, wherein the organic layer comprises at least one light-emitting layer containing at least one inventive compound or at least one preferred compound of the formulae 1-1 or 1-2 as defined, or a compound from table 1 or one of compounds E1 to E24, and at least one further matrix material.
  • the present invention accordingly further provides an organic electronic device as described above, wherein the organic layer comprises at least one light-emitting layer containing at least one inventive compound or at least one preferred compound of the formulae 1-1 or 1-2 as defined, or a compound from table 1 or one of compounds E1 to E24, and two further matrix materials.
  • Suitable matrix materials that can be used in combination with the compounds of the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives or dibenzofuran derivatives.
  • a further phosphorescent emitter having shorter-wavelength emission than the actual emitter is present as co-host in the mixture, or a compound not involved in charge transport to a significant extent, if at all, for example a wide band-gap compound.
  • a wide-band gap material is understood herein to mean a material within the scope of the disclosure of US 7,294,849 which is characterized by a band gap of at least 3.5 eV, the band gap being understood to mean the gap between the HOMO and LUMO energy of a material.
  • Particularly suitable hole-transporting materials that can advantageously be combined with inventive compound or compounds of the formulae 1-1 or 1-2 as defined, as described above or described with preference, in a mixed matrix system may be selected from the compounds of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described hereinafter.
  • the invention accordingly further provides an organic electronic device containing an anode, a cathode and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer comprises at least one inventive compound as matrix material 1, as described above or as described with preference, and at least one compound of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) as matrix material 2, , where the symbols and indices used are as follows:
  • a 1 is C(R 7 ) 2 , NR 7 , O or S;
  • L is a bond, O, S, C(R 7 ) 2 or NR 7 ;
  • a at each instance is independently a group of the formula (HH-4-1) or (HH-4-2),
  • X2 is the same or different at each instance and is CH, CR 6 or N, where not more than 2 symbols X2 can be N;
  • II 1 , II 2 where they occur are a bond, O, S, C(R 7 )2 or NR 7 ;
  • Ars is the same or different at each instance and is independently an aromatic or heteroaromatic ring system which has 5 to 40 ring atoms and may be substituted by one or more R 7 radicals;
  • s is preferably 0 or 1 when the R 6 radical is not D, or more preferably 0.
  • t is preferably 0 or 1 when the R 6 radical is not D, or more preferably 0.
  • u is preferably 0 or 1 when the R 6 radical is not D, or more preferably 0.
  • the sum total of the indices s, t and u in compounds of the formulae (HH-1), (HH-2), (HH- 3), (HH-5) or (HH-6) is preferably not more than 6, especially preferably not more than 4 and more preferably not more than 2. This is preferably the case when R 6 is not D.
  • c, c1 , c2 at each instance are each independently 0 or 1 , where the sum total of the indices at each instance c+c1+c2 is 1.
  • c2 is preferably defined as 1.
  • L is preferably a single bond or C(R 7 )2 where R 7 has a definition given above; more preferably, L is a single bond.
  • v is preferably 0 or 1 when the R 6 radical is not D.
  • II 1 or II 2 where they occur are preferably a single bond or C(R 7 )2 where R 7 as a definition given above; more preferably, II 1 or II 2 where they occur are a single bond.
  • R 6 is the same or different at each instance and is selected from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl group may in each case be substituted by one or more R 7 radicals, or an aromatic heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 ring atoms, and may be substituted in each case by one or more R 7 radicals.
  • R 6 is the same or different at each instance and is selected from the group consisting of D or an aromatic heteroaromatic ring system which has 6 to 30 ring atoms and may be substituted by one or more R 7 radicals.
  • Ars in compounds of the formulae (HH-1), (HH-2), (HH-3), (HH-5) or (HH-6) is selected from phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta- or para-terphenyl or branched terphenyl, quaterphenyl, especially ortho-, meta- or para-quaterphenyl or branched quaterphenyl, fluorenyl which may be joined via the 1 , 2, 3 or 4 position, spirobifluorenyl which may be joined via the 1 , 2, 3 or 4 position, naphthyl, especially 1- or 2-bonded naphthyl, or radicals derived from indole, benzofuran, benzothiophene, carbazole which may be joined via the 1 , 2, 3 or 4 position, dibenzofuran which may be joined via the 1 , 2, 3 or 4 position, dibenzothiophene which may be joined
  • the substituent R 7 bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may also be substituted by one or more R 8 radicals.
  • this substituent R 7 is the same or different at each instance and is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, especially having 6 to 18 aromatic ring atoms.
  • R 7 are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably unsubstituted, and radicals derived from triazine, pyrimidine and quinazoline, which may be substituted by one or more R 8 radicals.
  • R 7 bonded to this carbon atom are preferably the same or different at each instance and are a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more R 5 radicals.
  • R 7 is a methyl group or a phenyl group.
  • the R 7 radicals together may also form a ring system, which leads to a spiro system.
  • these compounds are partly or fully deuterated, more preferably fully deuterated.
  • HH-4 Compounds of the formula (HH-4) are disclosed, for example, in W02021/180614, pages 110 to 119, especially as examples on pages 120 to 127.
  • the preparation thereof is disclosed in W02021/180614 A1 on page 128, and in the synthesis examples on pages 214 to 218.
  • the at least one further matrix material is a deuterated compound
  • this at least one matrix material is a mixture of deuterated compounds of the same chemical base structure that differ merely by the level of deuteration.
  • this is a mixture of deuterated compounds of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described above, wherein the deuteration level of these compounds is at least 50% to 90%, preferably 70% to 100%.
  • this is a mixture of deuterated compounds of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and/or (HH-6), as described above, wherein the deuteration level of these compounds is at least 50% to 90%, preferably 70% to 100%.
  • Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014 A, WO2017/122988 A1 , KR2020052820 A, KR101978651 B1 and WO2018/110887 A1 or in Bulletin of the Chemical Society of Japan, 2021 , 94(2), 600-605 or Asian Journal of Organic Chemistry, 2017, 6(8), 1063- 1071.
  • a suitable method of deuterating a compound by exchange of one or more hydrogen atoms for deuterium atoms is a treatment of the compound to be deuterated in the presence of a platinum catalyst or palladium catalyst and a deuterium source.
  • deuterium source means any compound that contains one or more deuterium atoms and is able to release them under suitable conditions.
  • the platinum catalyst is preferably dry platinum on charcoal, preferably 5% dry platinum on charcoal.
  • the palladium catalyst is preferably dry palladium on charcoal, preferably 5% dry palladium on charcoal.
  • a suitable deuterium source is D2O, benzene-d6, chloroform-d, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4 or toluene-d8.
  • a preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent.
  • a particularly preferred deuterium source is the combination of D2O with a fully deuterated organic solvent, where the fully deuterated solvent here is not restricted.
  • Particularly suitable fully deuterated solvents are benzene-d6 and toluene-d8.
  • a particularly preferred deuterium source is a combination of D2O and toluene-d8.
  • the reaction is preferably conducted with heating, more preferably with heating to temperatures between 100°C and 200°C.ln addition, the reaction is preferably conducted under pressure.
  • Suitable further matrix materials for a combination with compounds of the formula (1), as described above or described as preferred are the compounds described in WO2019/229011 A1 , table 3, pages 137 to 203, which may also be partly or fully deuterated.
  • Suitable further matrix materials for a combination with compounds of the formula (1) or preferred compounds of the formula (1), as described above or described as preferred are the compounds described in WO2021/180625 A1 , table 3, pages 131 to 137, and in table 4, pages 137 to 139, which may also be partly or fully deuterated.
  • Suitable further matrix materials for a combination with inventive compounds or preferred inventive compounds, as described above or described as preferred are the compounds described in WO2011/088877 A1 , table on page 30, compounds 1 to 166, which may also be partly or fully deuterated.
  • Suitable further matrix materials for a combination with inventive compounds or preferred inventive compounds, as described above or described as preferred are the compounds described in WO2011/128017 A1 , table on page 23, compounds 1 to 151 , which may also be partly or fully deuterated.
  • Suitable further matrix materials for a combination with inventive compounds or preferred inventive compounds are the compounds described in KR20230034896 A, on pages 42 to 47, compounds [2-1] to [2- 110], or on pages 49 to 51 , compounds [3-1] to [3-26],
  • HH-1 for a combination with inventive compounds or preferred compounds of the formulae 1-1 or 1-2, as described above or described with preference, especially suitable compounds are those of the formula (HH-1) and/or of the formula (HH-4) and/or of the formula (HH-5), as described above or described as preferred.
  • HH-1 for a combination with inventive compounds or preferred compounds of the formulae 1-1 or 1-2, as described above or described with preference, especially suitable compounds are those of the formula (HH-1) in which at least one Ars group is a heteroaromatic ring system which has 5 to 40 ring atoms and may be substituted by one or more R 7 radicals and/or compounds of the formula (HH-4) and/or compounds of the formula (HH-5).
  • Particularly suitable compounds of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6) that are selected in accordance with the invention and are preferably used in combination with at least one inventive compound in the electroluminescent device of the invention are the compounds in table 4.
  • the aforementioned host materials of the inventive compounds or formulae 1-1 or 1-2 and the embodiments thereof that are described as preferred or the compounds from table 1 and compounds E1 to E24 can be combined as desired in the device of the invention with the aforementioned matrix materials/host materials, the matrix materials/host materials of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) and their embodiments in table 3 that are described as preferred or the compounds from table 3, or compounds H1 to H33.
  • Very particularly preferred mixtures of the inventive compounds with the host materials of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) for the device of the invention are obtained by combination of the compounds E1 to E24 with the compounds H1 to H33 as shown hereinafter in table 5.
  • the first mixture M1 for example, is a combination of compound E1 with H1.
  • the concentration of the host material of the inventive compound or formulae 1-1 or 1-2 as described above or described as preferred in the mixture of the invention or in the lightemitting layer of the device of the invention is typically in the range from 5% by weight to 90% by weight, preferably in the range from 10% by weight to 85% by weight, more preferably in the range from 20% by weight to 85% by weight, even more preferably in the range from 30% by weight to 80% by weight, very especially preferably in the range from 20% by weight to 60% by weight and most preferably in the range from 30% by weight to 50% by weight, based on the overall mixture or based on the overall composition of the light-emitting layer.
  • the concentration of the sum total of all host materials of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), as described above or described as preferred, in the mixture of the invention or in the light-emitting layer of the device of the invention is typically in the range from 10% by weight to 95% by weight, preferably in the range from 15% by weight to 90% by weight, more preferably in the range from 15% by weight to 80% by weight, even more preferably in the range from 20% by weight to 70% by weight, very especially preferably in the range from 40% by weight to 80% by weight and most preferably in the range from 50% by weight to 70% by weight, based on the overall mixture or based on the overall composition of the light-emitting layer.
  • the present invention also relates to a mixture which, as well as the aforementioned host materials of inventive compounds, called host material 1 hereinafter, and the host material of at least one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), called host material 2 hereinafter, as described above or described as preferred, also comprises at least one phosphorescent emitter.
  • the present invention also relates to a mixture selected from M1 to M693 that also comprises at least one phosphorescent emitter.
  • the present invention also relates to an organic electroluminescent device as described above or described as preferred, wherein the light-emitting layer, as well as the aforementioned host materials of the formulae (1) and at least one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), as described above or described as preferred, especially the material combinations M1 to M693, also comprises at least one phosphorescent emitter.
  • phosphorescent emitters typically encompasses compounds where the light is emitted through a spin-forbidden transition from an excited state having higher spin multiplicity, i.e. a spin state > 1 , for example through a transition from a triplet state or a state having an even higher spin quantum number, for example a quintet state. This is preferably understood to mean a transition from a triplet state.
  • Suitable phosphorescent emitters are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal having this atomic number.
  • Preferred phosphorescence emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
  • all luminescent compounds containing the abovementioned metals are regarded as phosphorescent emitters.
  • Preferred phosphorescent emitters according to the present invention conform to the formula (Illa) Formula (Illa) where the symbols and indices for this formula (Illa) are defined as follows: n+m is 3, n is 1 or 2, m is 2 or 1,
  • X is the same or different at each instance and is N or CR
  • the invention accordingly further provides an organic electroluminescent device as described above or described as preferred, characterized in that the light-emitting layer, as well as the host materials 1 and 2, comprises at least one phosphorescent emitter conforming to the formula (Illa) as described above.
  • n is preferably 1 and m is preferably 2.
  • one X is selected from N and the other X are CR, or all X are the same or different at each instance and are CR.
  • emitters of the formula (Illa) at least one R is preferably different from H. In emitters of the formula (Illa), preferably two R are different from H and have one of the other definitions given above for the emitters of the formula (Illa).
  • Ri is H or D
  • R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 carbon atoms or a partly or fully deuterated branched or linear alkyl group having 1 to 10 carbon atoms or a cycloalkyl group which has 4 to 10 carbon atoms and may be partly or fully substituted by deuterium.
  • Preferred phosphorescent emitters according to the present invention conform to the formulae (VI), (VII) or (VIII)
  • Ri is H or D
  • R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 carbon atoms or a partly or fully deuterated branched or linear alkyl group having 1 to 10 carbon atoms or a cycloalkyl group which has 4 to 10 carbon atoms and may be partly or fully substituted by deuterium.
  • Preferred examples of phosphorescent emitters are described in WO2019/007867 on pages 120 to 126 in table 5, and on pages 127 to 129 in table 6. The emitters are incorporated into description by this reference.
  • any mixture selected from the sum of the mixtures M1 to M693 is preferably combined with a compound of the formula (Illa) or a compound of the formulae (I) to (VIII) or a compound from table 6.
  • the light-emitting layer in the organic electroluminescent device of the invention containing at least one phosphorescent emitter, is preferably an infrared-emitting or yellow-, orange-, red-, green-, blue- or ultraviolet-emitting layer, more preferably a yellow- or green-emitting layer and most preferably a green-emitting layer.
  • a yellow-emitting layer is understood here to mean a layer having a photoluminescence maximum within the range from 540 to 570 nm.
  • An orange-emitting layer is understood to mean a layer having a photoluminescence maximum within the range from 570 to 600 nm.
  • a red-emitting layer is understood to mean a layer having a photoluminescence maximum within the range from 600 to 750 nm.
  • a green-emitting layer is understood to mean a layer having a photoluminescence maximum within the range from 490 to 540 nm.
  • a blueemitting layer is understood to mean a layer having a photoluminescence maximum within the range from 440 to 490 nm.
  • the photoluminescence maximum of the layer is determined here by measuring the photoluminescence spectrum of the layer having a layer thickness of 50 nm at room temperature, where the layer comprises the inventive combination of the host material 1 of the inventive compound or formulae 1-1 or 1-2 and of the host material 2 consisting of at least one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), and the corresponding emitter.
  • the photoluminescence spectrum of the layer is recorded, for example, with a commercial photoluminescence spectrometer.
  • the photoluminescence spectrum of the emitter chosen is generally measured in oxygen- free solution, 10 -5 molar, at room temperature, a suitable solvent being any in which the chosen emitter dissolves in the concentration mentioned. Particularly suitable solvents are typically toluene or 2-methyl-THF, but also dichloromethane. Measurement is effected with a commercial photoluminescence spectrometer.
  • Preferred phosphorescent emitters are accordingly yellow emitters, preferably of the formula (Illa), of the formulae (I) to (VIII) or from table 6, the triplet energy Ti of which is preferably ⁇ 2.3 eV to ⁇ 2.1 eV.
  • Preferred phosphorescent emitters are accordingly green emitters, preferably of the formula (Illa), of the formulae (I) to (VIII) or from table 6, the triplet energy Ti of which is preferably ⁇ 2.5 eV to ⁇ 2.3 eV.
  • Particularly preferred phosphorescent emitters are accordingly green emitters, preferably of the formula (Illa), of the formulae (I) to (VIII) or from table 6 as described above, the triplet energy Ti of which is preferably ⁇ 2.5 eV to ⁇ 2.3 eV.
  • green emitters preferably of the formula (Illa), of the formulae (I) to (VIII) or from table 6, as described above, are selected for the mixture of the invention or emitting layer of the invention.
  • fluorescent emitters it is also possible for fluorescent emitters to be present in the light-emitting layer of the device of the invention or in the mixture of the invention.
  • Preferred fluorescent emitting compounds are selected from the class of the arylamines, where preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a fused ring system, more preferably having at least 14 ring atoms.
  • Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines or aromatic chrysenediamines.
  • An aromatic anthraceneamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9 position.
  • Aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10 positions.
  • Aromatic pyreneamines, pyrenediamines, chryseneamines and chrysenediamines are defined analogously, where the diarylamino groups are bonded to the pyrene preferably in the 1 position or 1,6 positions.
  • Further preferred emitting compounds are indenofluoreneamines or -diamines, benzoindenofluoreneamines or - diamines, and dibenzoindenofluoreneamines or -diamines, and indenofluorene derivatives having fused aryl groups.
  • pyrenearylamines Likewise preferred are benzoindenofluoreneamines, benzofluoreneamines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives joined to furan units or to thiophene units.
  • the light-emitting device or the mixture of the invention may additionally also comprise materials that exhibit TADF (thermally activated delayed fluorescence).
  • the at least one light-emitting layer of the organic electroluminescent device may have three or four different matrix materials, preferably three different matrix materials.
  • These corresponding mixed matrix systems may consist of the matrix materials described for the host material 1 and the host material 2, but they may also comprise, as a third or fourth matrix material, for example alongside a host material 1 or host material 2, wide-band-gap materials, bipolar host materials, electron transport materials (ETM) or hole transport materials (HTM).
  • the mixed matrix system is optimized for an emitter of the formula (Illa), of the formulae (I) to (VIII), or for an emitter from table 6.
  • the mixture aside from the constituents of the host material of the inventive compound and the host material 2 as described above or described with preference, does not comprise any further constituents, i.e. functional materials.
  • These mixtures are also referred to as premix systems that are used as the sole material source in the vapor deposition of the host materials for the light-emitting layer and have a constant mixing ratio in the vapor deposition. In this way, it is possible in a simple and rapid manner to achieve the vapor deposition of a layer with homogeneous distribution of the components without the need for precise actuation of a multitude of material sources.
  • the mixture aside from the constituents of the host material of the inventive compound and the host material 2, as described above or described with preference, also comprises a phosphorescent emitter, as described above.
  • this mixture may also be used as the sole material source.
  • premix systems consisting of two matrix materials, namely one compound of the inventive compounds or the formula 1-1 or 1-2 and one compound of one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6).
  • premix systems consisting of three matrix materials, namely one compound of the inventive compounds or the formulae 1-1 or 1-2 and two compounds of one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6).
  • the components or constituents of the light-emitting layer of the device of the invention may thus be processed by vapor deposition or from solution.
  • the material combination of host materials 1 and 2, as described above or described as preferred, optionally with the phosphorescent emitter, as described above or described as preferred, are provided for that purpose in a formulation containing at least one solvent. Suitable formulations have been described above.
  • the light-emitting layer in the device of the invention contains preferably between 99.9% and 1% by volume, further preferably between 99% and 10% by volume, especially preferably between 98% and 60% by volume, very especially preferably between 97% and 80% by volume, of matrix material composed of at least one compound of the inventive compounds or the formula 1-1 or 1-2 and at least one compound of one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) according to the preferred embodiments, based on the overall composition of emitter and matrix material.
  • the light-emitting layer in the device of the invention preferably contains between 0.1% and 99% by volume, further preferably between 1% and 90% by volume, more preferably between 2% and 40% by volume, most preferably between 3% and 20% by volume, of the emitter based on the overall composition of the light-emitting layer composed of emitter and matrix material. If the compounds are processed from solution, preference is given to using the corresponding amounts in % by weight rather than the above-specified amounts in % by volume.
  • the present invention also relates to an organic electroluminescent device as described above or described as preferred, wherein the organic layer comprises a hole injection layer (HIL) and/or a hole transport layer (HTL), the hole-injecting material and holetransporting material of which belongs to the class of the arylamines.
  • HIL hole injection layer
  • HTL hole transport layer
  • the sequence of layers in the organic electroluminescent device of the invention is preferably as follows: anode I hole injection layer I hole transport layer I emitting layer I hole blocker layer I electron transport layer / electron injection layer / cathode.
  • This sequence of the layers is a preferred sequence.
  • Materials used for the electron transport layer may be any materials as used according to the prior art as electron transport materials in the electron transport layer.
  • aluminum complexes for example Alqs, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.
  • Suitable cathodes of the device of the invention are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth metal and silver, for example an alloy composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, it is also possible to use further metals having a relatively high work function, for example Ag or Al, in which case combinations of the metals such as Ca/Ag, Mg/Ag or Ba/Ag, for example, are generally used.

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Abstract

La présente invention concerne des composés contenant au moins une fraction indolocarbazole Zi, au moins une fraction N-hétéroaryle Zh et au moins une fraction Zt représentée par la formule (1), des mélanges et des dispositifs électroniques contenant ces composés, en particulier des dispositifs électroluminescents organiques contenant ces composés en tant que matériaux de matrice, matériaux de transport d'électrons ou matériaux d'obstruction de trous.
PCT/EP2024/074588 2023-09-06 2024-09-03 Matériaux pour dispositifs électroluminescents organiques Pending WO2025051734A1 (fr)

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