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WO2025228800A1 - Matériaux pour dispositifs électroniques organiques - Google Patents

Matériaux pour dispositifs électroniques organiques

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Publication number
WO2025228800A1
WO2025228800A1 PCT/EP2025/061312 EP2025061312W WO2025228800A1 WO 2025228800 A1 WO2025228800 A1 WO 2025228800A1 EP 2025061312 W EP2025061312 W EP 2025061312W WO 2025228800 A1 WO2025228800 A1 WO 2025228800A1
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Prior art keywords
atoms
residues
compounds
aromatic
group
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PCT/EP2025/061312
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German (de)
English (en)
Inventor
Amir Hossain Parham
Sebastian Stolz
Jonas Valentin Kroeber
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of WO2025228800A1 publication Critical patent/WO2025228800A1/fr
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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C07D487/12—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 three hetero rings
    • C07D487/14—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to compounds and organic electronic devices such as OLEDs (organic light-emitting diodes) which contain these compounds, for example as hole transport materials and/or matrix materials, optionally in combination with a further matrix material.
  • OLEDs organic light-emitting diodes
  • the present invention further relates to mixtures containing these compounds.
  • organic electroluminescent devices e.g., OLEDs or OLECs – organic light-emitting electrochemical cells
  • organic semiconductors are used as organic functional materials
  • organometallic complexes exhibiting phosphorescence have become established as emitting materials.
  • using organometallic compounds as phosphor emitters allows for up to four times the energy and power efficiency.
  • organic electroluminescent devices are not solely determined by the emitters used.
  • the other materials employed such as host and matrix materials, hole-blocking materials, electron transport materials, and electron/exciton blocking materials, are also of particular importance. Improvements to these materials can lead to significant enhancements in electroluminescent devices.
  • matrix material is commonly used to refer to a host material for phosphorescent emitters. This usage of the term “matrix material” is also applied to the present invention.
  • triarylamine compounds such as spirobifluorenamines and fluorenamines are known to be used as hole transport and hole injection materials in electronic devices.
  • carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, benzofurocarbazole derivatives, and benzothienocarbazole derivatives are used as matrix materials for phosphorescent emitters.
  • Indolocarbazole derivatives, which can be used as matrix materials in OLEDs are known, among others, from KR. 10201800999539, US 2023/159550, US 2016/0293853 or WO 2011/128017 described.
  • the object of the present invention is therefore to provide compounds suitable for use in an organic electroluminescent device (synonymously used for use in an organic light-emitting device) and which, when used in this device, result in favorable properties, as well as to provide the corresponding organic light-emitting device.
  • the object of the present invention is to provide compounds that lead to a long lifetime, good efficiency, and low operating voltage in a phosphorescent or fluorescent, especially phosphorescent, OLED.
  • the properties of the matrix materials also have a significant influence on the lifetime and efficiency of the organic electroluminescent device.
  • organic light-emitting devices containing compounds according to the following formula (1) exhibit improvements over the prior art, particularly when the compounds are used as matrix material for phosphorescent emitters.
  • the combination of at least one compound of formula (1) as the first host material and at least one electron-transporting compound for example in combination with one or more compounds of formulas (A), (B), (C), (D) or (E), as a further host material or further host materials in a light-emitting layer of an organic electronic device, in particular an organic electroluminescent device (synonymous with organic light-emitting device), solves this problem and eliminates the disadvantages of the prior art.
  • a first object of the invention are compounds of formula (I), Formula (I), where:
  • Ring system selected from the group consisting of carbazole, dibenzofuran or dibenzothiophene, each of which may be substituted by one or more R 5 residues;
  • R1 , R2 , R3 , R4 are, in each occurrence, the same or different: H, D, F, a straight-chain alkyl, alkoxy, or thioalkoxy group with 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy, or thioalkoxy group with 3 to 40 C atoms, or an alkenyl group with 2 to 20 C atoms, wherein in each group one or more H atoms may be replaced by D, an aromatic ring system with 6 to 40 ring atoms, or a heteroaromatic ring system with 5 to 40 ring atoms, wherein the aromatic or heteroaromatic ring systems may each be substituted by one or more R6 residues; Two or more adjacent residues R 1 , two or more adjacent residues R 2 , two or more adjacent residues R 3 , can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted with one
  • Another object of the invention is a mixture comprising at least one compound of formula (I) as previously described or more preferably described later, and at least one further compound selected from the group consisting of matrix materials, phosphorescent emitters, fluorescent emitters and/or emitters exhibiting TADF (thermally activated delayed fluorescence).
  • TADF thermalally activated delayed fluorescence
  • Another aspect of the invention is the use of at least one compound of formula (I) in an organic electronic device.
  • Another object of the invention is an organic electronic, preferably light-emitting, device comprising an anode, a cathode and at least one organic layer containing at least one compound of formula (I), as previously described or more preferably described later.
  • D or “D atom” denotes deuterium.
  • the degree of deuteration indicates the proportion of hydrogen atoms replaced by deuterium. Since deuterated compounds are often mixtures of compounds that differ in the precise position and proportion of D atoms, the degree of deuteration represents the average proportion of hydrogen atoms replaced by D. Thus, a degree of deuteration of 50 mol% means that, on average, 50 mol% of the hydrogen atoms in the compound are replaced by D, representing an average degree of deuteration.
  • An aryl group according to this invention contains 6 to 40 ring atoms, preferably carbon atoms.
  • a heteroaryl group according to this invention contains 5 to 40 ring atoms, wherein the ring atoms comprise carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from nitrogen, oxygen, and/or sulfur.
  • aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., phenyl, derived from benzene, or a simple heteroaromatic cycle, for example, derived from furan or thiophene, or a fused aryl or heteroaryl group, for example, derived from naphthalene, anthracene, phenanthrene, or benzopyrans.
  • An aryl group with 6 to 30 carbon atoms is therefore Preferably phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylenyl, fluoranthenyl, dibenzoanthracene, chrysenyl, or perylenyl, wherein the attachment of the aryl group as a substituent is not restricted.
  • the aryl group according to this invention can bear one or more substituents, the suitable substituent being described below. Deuterium is preferred.
  • a heteroaryl group is understood to be either a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine, or thiophene, or a condensed heteroaryl group, for example derived from quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, or carbazole.
  • the term heteroaryl group also includes a heteroaryl group that is bonded by a single bond to an aryl group or to another heteroaryl group, for example phenyl-bipyridyl or bipyridyl.
  • the heteroaryl group in the sense of this invention may bear one or more substituents, the suitable substituent being described below. Deuterium is preferred as the substituent. If no such substituent is described, the heteroaryl group is unsubstituted.
  • An aromatic ring system according to this invention contains 6 to 40 carbon atoms in the ring system.
  • the aromatic ring system comprises aryl groups, as previously described, and the term is used synonymously below.
  • a heteroaromatic ring system according to this invention contains 5 to 40 ring atoms and at least one heteroatom.
  • a preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom.
  • the heteroaromatic ring system comprises heteroaryl groups as previously described, and the term is used synonymously hereafter.
  • An aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be linked via any position on the aromatic or heteroaromatic compound and which can bear one or more substituents, as described below, preferably includes the following groups, which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, Naphthacene, Pentacene, Benzopyrene, Biphenyl, Terphenyl, Quaterphenyl, Fluorene, 9,9-Dimethylfluorene, 9,9-Diphenylfluorene, Spirobifluorene, Dihydrophenanthrene, Dihydropyrene, Tetrahydropyrene, cis- or trans-indenofluorene, cis-
  • a straight-chain alkyl group with 1 to 20 carbon atoms preferably with 1 to 10 carbon atoms, more preferably with 1 to 6 carbon atoms, or a branched alkyl group with 3 to 20 carbon atoms, preferably with 3 to 10 carbon atoms, more preferably with 3 to 8 carbon atoms, in which one or more non-adjacent CH2 groups may be replaced by O or S, and wherein at least one hydrogen atom may be replaced by D, F, or CN, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n-propoyl, 1-thio-i-butyl, 1-Thio-n-butyl or 1-Thio-t-butyl understood.
  • Adjacent carbon atoms within the meaning of the present invention are carbon atoms that are directly linked to one another. Furthermore, “adjacent residues” in the definition of residues means that these residues are bonded to the same carbon atom or to neighboring carbon atoms. These definitions apply accordingly, inter alia, to the terms “adjacent groups” and “adjacent substituents”.
  • the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following diagram:
  • Ar represents an aromatic ring system with 6 to 25 ring atoms, preferably an aryl group with 6 to 18 C atoms, which may be substituted by one or more R 5 residues, or is selected from the group consisting of carbazole, dibenzofuran or dibenzothiophene, each of which may be substituted by one or more R 5 residues.
  • Ar is therefore preferably selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, in particular 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl, triphenylenyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl, each of which may be substituted by one or more R 5 residues.
  • Ar is therefore particularly preferably selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, triphenylenyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl, each of which may be substituted by one or more R 5 residues.
  • the residues R1 , R2 , R3 , R4 are the same or different in each occurrence and are preferably selected from the group consisting of H, D, a straight-chain alkyl, alkoxy, or thioalkoxy group with 1 to 20 carbon atoms, preferably with 1 to 10 carbon atoms, particularly preferably with 1 to 6 carbon atoms, a branched or cyclic alkyl, alkoxy, or thioalkoxy group with 3 to 20 carbon atoms, preferably with 3 to 10 carbon atoms, particularly preferably with 3 to 8 carbon atoms, wherein in each of the respective groups one or more H atoms may be replaced by D, or an alkenyl group with 2 to 4 carbon atoms, or an aryl group with 6 to 25 carbon atoms, preferably with 6 to 18 carbon atoms, or a heteroaryl group with 5 to 25 Ring atoms, preferably with 5 to 13 ring atoms, wherein the aryl or heteroaryl group may
  • residues R1 , R2 , R3 , and R4 are the same or different in each occurrence and are selected from the group consisting of H, D, an aryl group with 6 to 18 carbon atoms, or a heteroaryl group with 5 to 13 ring atoms, each of which may be substituted with one or more residues R6 .
  • Suitable aryl groups as residues R1 , R2 , R3 , and R4 are phenyl, ortho-, meta-, or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, 1-, 2-, 3-, or 4-fluorenyl, in particular 4-fluorenyl, 1-, 2-, 3-, or 4-spirobifluorenyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl, and/or triphenylenyl.
  • Suitable heteroaryl groups as residues R1 , R2 , R3 and R4 are 1-, 2-, 3- or 4-carbazolyl, N-carbazolyl, 1-, 2-, 3- or 4-dibenzofuranyl or 1-, 2-, 3- or
  • the R5 group is preferably selected, in each instance, from the group consisting of H, D, OH, a straight-chain alkyl group with 1 to 10 carbon atoms, preferably with 1 to 6 carbon atoms, a branched or cyclic alkyl group with 3 to 10 carbon atoms, preferably with 3 to 8 carbon atoms, wherein one or more hydrogen atoms in these alkyl groups may be replaced by D, or an aryl group with 6 to 18 carbon atoms, or a heteroaryl group with 5 to 13 ring atoms, wherein in the aryl or heteroaryl group one or more hydrogen atoms may be replaced by D or an alkyl group with 1 to 4 carbon atoms, preferably by D.
  • a dibenzofuran, dibenzothiophene, or a carbazole may be selected as the heteroaryl group.
  • the residue R 5 is selected in each occurrence, either the same or different, from the group consisting of H, D, an aryl group with 6 to 18 C atoms, dibenzofuranyl or carbazolyl, wherein one or more H atoms may be replaced by D.
  • the residue R 5 is preferably selected from the group consisting of H or D, either the same or different, for each occurrence.
  • the residue R5 is preferably selected, in each instance, as the same or different from the group consisting of H, D, OH, a straight-chain alkyl group with 1 to 10 carbon atoms, preferably with 1 to 6 carbon atoms, a branched or cyclic alkyl group with 3 to 10 carbon atoms, preferably with 3 to 8 carbon atoms, wherein one or more hydrogen atoms in these alkyl groups may be replaced by D, or an aryl group with 6 to 18 carbon atoms, or a heteroaryl group with 5 to 13 ring atoms, wherein in the aryl or heteroaryl group one or more hydrogen atoms may be replaced by D or an alkyl group with 1 to 4 carbon atoms, preferably by D.
  • a dibenzofuran, dibenzothiophene, or a carbazole may be selected as the heteroaryl group.
  • the residue R 5 is selected in each occurrence, either the same or different, from the group consisting of H, D, an aryl group with 6 to 18 C atoms, dibenzofuranyl or carbazolyl, wherein one or more H atoms may be replaced by D.
  • the residue R 5 is preferably selected from the group consisting of H or D, either the same or different in each occurrence. If Ar is a carbazolyl, then the residue R 5 on the N atom is preferably an aryl group with 6 to 18 C atoms or a heteroaryl group with 5 to 13 ring atoms, wherein one or more H atoms in the aryl or heteroaryl group may be replaced by D.
  • At least one of the residues R1 , R2 , R3 , R4 , or R6 is D and none of the residues R5 represents D, or in the compounds according to the invention, at least one of the residues R5 is D and none of the residues R1 , R2 , R3 , R4 , or R6 represents D. It is further preferred within the scope of the present invention that at least one of the residues R1 , R2 , R3 , R4 , or R6 is D and at least one of the residues R5 is D.
  • all residues are R5 D and none of the residues R1 , R2 , R3 , R4 , or R6 represent D. It is also possible that all residues are R1 , R2 , R3 , R4 , or R6 represent D and at least one of the residues is R5 D.
  • the compounds of formula (I) are deuterated compounds, it is possible during their preparation, provided that the preparation is carried out by reacting a non-deuterated compound of formula (I) with a deuterating source, or provided that deuterated starting compounds are chosen for the preparation which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is formed, which differ only in the degree of deuteration and/or the deuteration patterns.
  • the average degree of deuteration is 5 mol% to 100 mol%, preferably 30 mol% to 95 mol%, particularly preferably 50 mol% to 90 mol%, and most preferably 70 mol% to 95 mol%.
  • deuteration methods are known to those skilled in the art and are described, for example, in KR2016041014, WO2017/122988, KR202005282, KR101978651 and WO2018/110887 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 for deuterating a compound by exchanging one or more hydrogen atoms for dium atoms is to treat the compound to be deuterated in the presence of a platinum or palladium catalyst and a deuterium source.
  • deuterium source means any compound that contains one or more dium atoms and can release them under suitable conditions.
  • the platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon.
  • the palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon.
  • 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, the fully deuterated solvent not being restricted here.
  • 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 carried out under heating, more preferably under heating to temperatures between 100 °C and 200 °C. Furthermore, the reaction is preferably carried out under pressure.
  • an index such as D1-D29 means that in the corresponding compound, 1 to 29 H atoms can be replaced by D; that is, the first number indicates the minimum number of H substitutions by D, and the second number indicates the maximum number of H substitutions by D. For example, if Di is chosen, this means that one of the 29 H atoms can be replaced by a D atom.
  • Particularly suitable compounds of formula (I) are compounds H1 to H30 of Table 2.
  • the compounds according to the invention can be prepared by synthesis steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc.
  • the compounds are shown with a small number of substituents to simplify the structures. This does not preclude the presence of any further substituents in the processes.
  • the methods shown for the synthesis of the compounds according to the invention are to be understood as examples. Those skilled in the art can develop alternative synthetic routes within the scope of their general technical knowledge.
  • Scheme 1 For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention or of mixtures of compounds according to the invention with further functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters and/or emitters exhibiting TADF, are required. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose.
  • Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ⁇ -terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin.
  • a suitable formulation is a formulation containing at least one compound according to the invention, as described above, or a mixture according to the invention, as described below, and at least one solvent.
  • the solvent can be one of the solvents mentioned above or a mixture of these solvents.
  • the compounds of formula (I) according to the invention are suitable for use in an organic electroluminescent device, in particular as a hole transport material, as a hole injection material, as an electron blocking material or as a matrix material.
  • a further object of the invention is therefore a mixture comprising at least one compound of formula (I) or a compound from Table 1 or one of compounds H1 to H30 and at least one further compound selected from the group consisting of matrix materials, phosphorescent emitters, fluorescent emitters and/or emitters exhibiting TADF (thermally activated delayed fluorescence).
  • matrix materials phosphorescent emitters, fluorescent emitters and/or emitters exhibiting TADF (thermally activated delayed fluorescence).
  • Another object of the present invention is an organic electronic device comprising an anode, a cathode and at least one organic layer, containing at least one compound of formula (I) or at least one preferred compound of formula (I), or a compound of Table 1 or one of the compounds H1 to H30.
  • the organic electronic device can 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, and organic photoreceptors.
  • OlCs organic integrated circuits
  • OFETs organic field-effect transistors
  • OTFTs organic thin-film transistors
  • O electroluminescent devices organic solar cells (OSCs), organic optical detectors, and organic photoreceptors.
  • the organic electronic device is an organic electroluminescent device (synonymously, an organic light-emitting device is used).
  • the organic electroluminescent device according to the invention is, for example, an organic light-emitting transistor (OLET), an organic field-quench device (OFQD), an organic light-emitting electrochemical cell (OLEC), 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 layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), and an electron transport layer.
  • the device according to the invention may contain an electron beam layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer, and/or charge-generation layers.
  • EML electron beam layer
  • EIL electron injection layer
  • EIL electron injection layer
  • an exciton blocking layer an electron blocking layer
  • charge-generation layers Several layers of this group, preferably selected from EML, HIL, HTL, ETL, EIL, and HBL, may also be included in the device according to the invention.
  • interlayers which may, for example, have an exciton-blocking function, may be introduced between two emitting layers.
  • the organic electroluminescent device according to the invention may also be a tandem electroluminescent device, particularly for white-emitting LEDs.
  • the device may also contain inorganic materials or layers composed entirely of inorganic materials.
  • the compound of formula (I) according to the invention can be used in different layers, depending on the precise structure.
  • a preferred option is an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters, or emitters containing TADF. (thermally activated delayed fluorescence), particularly for phosphorescent emitters.
  • the compound according to the invention can also be used in a hole transport layer and/or in an exciton blocking layer and/or in an electron blocking layer.
  • the compound according to the invention is particularly preferably used as a matrix material in an emitting layer or as a hole transport or electron blocking material in a hole transport or electron blocking layer.
  • Another object of the present invention is an organic electronic device as previously described, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of formula (I) or a compound of Table 1 or one of the compounds H1 to H30.
  • At least one further matrix material is selected for the device according to the invention in the light-emitting layer, which is used with compounds of formula (I) as previously described or preferably described, or with the compounds of Table 1 or the compounds H1 to H30.
  • Another object of the present invention is therefore an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer comprising at least one compound of formula (I) or a compound of Table 1 or one of compounds H1 to H30 and at least one further matrix material.
  • Another object of the present invention is therefore also an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer comprising at least one compound of formula (I) or a compound of Table 1 or one of compounds H1 to H30 and at least two further matrix materials.
  • Suitable matrix materials that can be used in combination with the compounds according to 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, azaborols or boron esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives.
  • a further phosphorescent emitter with a shorter wavelength than the actual emitter can be used. emitted, present as a co-host in the mixture, or a compound that does not participate in charge transport or does not participate to a significant extent, such as a wide band-gap compound.
  • wide-band-gap-Mater ⁇ a ⁇ is understood to be a material as defined in the revelation of US 7,294,849, characterized by a band gap of at least 3.5 eV, where band gap is understood to be the distance between the HOMO and LUMO energy of a material.
  • Particularly suitable matrix materials which are advantageously combined with compounds of formula (I), as previously or preferably described, in a mixed matrix system, can be selected from the compounds of formulas (A), (B), (C), (D) or (E), as described below.
  • a further object of the invention is therefore an organic electronic, in particular organic electroluminescent, device comprising 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 compound of formula (I) as matrix material 1, as previously described or preferably described, and at least one compound of formulas (A), (B), (C), (D) or (E) as matrix material 2 (further matrix material):
  • Formula (B), el (E) where the following applies to the symbols and indices used:
  • N is the same or different in each occurrence N or CR X , preferably N;
  • L is, in each occurrence, either a single bond or an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, each of which may be substituted with one or more R 11 residues;
  • R is the same or different in each occurrence D, F, CN, a straight-chain alkyl group with 1 to 10 C atoms, a branched or cyclic alkyl group with 3 to 10 C atoms, or an alkenyl group with 2 to 10 C atoms, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more R 8 substituents, and two adjacent substituents R## may together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, which may be substituted with one or more R 8 substituents;
  • Y is either the same or different from N or CR 1 1 in each occurrence, excluding the possibility that two adjacent Ys simultaneously represent N; 2 is O or S;
  • Ar 1 in each instance, represents an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more R 1 1 residues;
  • R 8 is, in each occurrence, the same or different H, D, F or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by F;
  • the substituent R 8 can independently preferentially stand for H, D or phenyl, whereby the H atoms of the phenyl group can be replaced by D singly or multiple times.
  • Another object of the invention is an organic electronic device, in particular an organic electroluminescent device comprising an anode, 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 compound of formula (I) as matrix material 1, as previously described or preferably described, and at least one compound of formulas (A), (B), (C), (D) and/or (E) as matrix material 2, as previously or preferably described.
  • the at least one light-emitting layer comprises at least one compound of formula (I) as matrix material 1, as previously described or preferably described, and at least one compound of formulas (A), (B), (C), (D) and/or (E) as matrix material 2, as previously or preferably described.
  • Preferred compounds of formula (A) are the compounds of formulas (Aa), (Ab), (Ac), (Ad), (Ae) and (Af), Formula (Aa)
  • W, W 1 means O, S, C(R W )2 or N- Ar 1 , either the same or different, depending on the occurrence;
  • R ⁇ sub> w ⁇ /sub> in each instance, is either a straight-chain alkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more hydrogen atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, a straight-chain alkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more hydrogen atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN; the two R ⁇ sub> w ⁇ /sub> substituents bonding to the same carbon atom may also form a ring system together;
  • A is the same or different CR 11 or N at each occurrence, with a maximum of two groups A per cycle representing N and where A represents C when L is bound to this position; a3 is either the same or different from 0, 1, 2, 3 or 4 in each occurrence; b3 is either the same or different from 0, 1, 2 or 3 in each occurrence; BJ
  • Ring B ⁇ is derived from an aryl group with 6 to 20 ring atoms, which may be substituted with one or more substituents R##;
  • L 1 is an aromatic ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more R 1 1 substituents; where L, X, Ar 1 , R 11 and R## have the meanings given above.
  • X preferably represents N.
  • W preferably represents O or N-Ar 1 .
  • A preferably represents CR 11 , whether the same or different, where A denotes a C atom when bonded to L.
  • W represents N-Ar 1 and the linker L, which is bonded to the structural unit containing W, preferably represents L-1 to L-13, which may be substituted with one or more substituents R 1 1 ,
  • R 11 preferably represents D or a non-deuterated, partially or fully deuterated aryl group with 6 to 18 carbon atoms.
  • R 11 particularly preferably represents D.
  • Particularly preferred compounds of formulas (A) and (Aa) are the compounds of formulas (Aa-1) to (Aa-8), Formula (Aa-1),
  • Ar 2 is either the same or different, an aromatic ring system with 6 to 40
  • Ring atoms which may be substituted with one or more substituents R 11 ;
  • L 2 is a bond or an aromatic ring system with 6 to 40 ring atoms, which may be substituted with one or more substituents R 11 ,
  • R 11 )x, (R 11 )y, (R 11 )xi , (R 1 1 )yi represent a monosubstitution, a disubstitution, a trisubstitution or the maximum permissible substitution with the substituent R 1 1 , R 18 is, in each occurrence, either the same or different, a straight-chain alkyl group with
  • all X preferably represent N.
  • the linkers L and L 2 are preferably a single bond.
  • the linker L is preferentially a single bond in every occurrence.
  • one of the linkers L preferably represents one of the groups L-1 to L-13, which may be substituted with one or more substituents R 11 , as described above.
  • one of the linkers L preferably represents the group L-12, which may be substituted with one or more substituents R 11 , as described above.
  • This single linker L is preferably bonded to the diazadibenzofuran or diazadibenzothiophene unit. All other linkers L are preferably single bonds.
  • substituents R 1 1 in (R 11 )x, (R 11 )y, (R 11 )xi , (R 11 )yi are preferably present as indicated below, most particularly preferably D.
  • the substituents R 11 of the substituent Ar 2 are preferably selected from D and/or CN. At least one R 11 of the substituent Ar 2 CN is particularly preferred.
  • substituents R 11 in (R 1 1 )x are preferably present as indicated, particularly preferably D.
  • substituents R 11 in (R 1 1 )y are preferably as indicated when occurring, but particularly preferably represent a non-deuterated, partially or completely deuterated aryl group with 6 to 18 C atoms.
  • Preferred compounds of formula (Ac) are compounds in which one of the linkers L is selected from groups L-1 to L-13, where L-1 to L-13 may be substituted with one or more substituents R 11 , as described above.
  • one of the linkers L is particularly preferably selected from groups L-1, L-2, L-3, L-8, L-9, L-12 and L-13, which may be substituted with one or more substituents R 11 , as described above.
  • This one linker L is preferentially bound to the carbazole unit of the compounds of formula (Ac).
  • All other left-handed L ties are preferably single ties.
  • Preferred compounds of formula (Ad) are compounds in which one of the linkers L is selected from groups L-1 to L-13, where L-1 to L-13 may be substituted with one or more substituents R 11 , as described above.
  • one of the linkers L is particularly preferably selected from groups L-1, L-2, L-3, L-8, L-9, L-12, and L-13, which may be substituted with one or more substituents R 11 , as described above.
  • one of the linkers L is particularly preferably selected from group L-12, which may be substituted with one or more substituents R 11 , as described above.
  • one of the linkers L is particularly preferably selected from group L-9, which may be substituted with one or more substituents R 11 , as described above.
  • This single linker L is preferentially bound to the 4/7-naphtho[1,2,3,4-de/]carbazole unit of the compounds of formula (Ad). All other linkers L are preferably single bonds.
  • all linkers L represent a single bond.
  • Preferred compounds of formula (Ae) are compounds in which W1 represents O or C( RW ) 2 , particularly preferably C( RW )2, where Rw has a meaning as described above. In this embodiment, it is preferred that Rw represents methyl or that two substituents Rw together with the carbon atom to which they bond form a ring system.
  • one of the linkers L is selected from groups L-1 to L-13, wherein L-1 to L-13 may be substituted with one or more substituents R11 , as described above.
  • one of the linkers L is particularly preferably selected from groups L-1, L-2, and L-3, which may be substituted with one or more substituents R11 , as described above.
  • This single linker L is preferably bonded to the carbazole-containing structural unit of the compounds of formula (Ae). All other linkers L are preferably single bonds. In an alternative embodiment of the compounds of formula (Ae), all linkers L represent single bonds.
  • Particularly preferred compounds of formulas (A) and (Af) are the compounds of formulas (Af-1) to (Af-3),
  • R 18 is a straight-chain alkyl group with 1 to 10 C atoms or an aryl group with 6 to 12 C atoms, wherein two substituents R 18 together can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more substituents R 11 ;
  • L 3 is a bond or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more substituents R 11 , wherein X, L, Ar 1 and R 1 1 have a previously mentioned or a previously and subsequently preferred meaning.
  • the linker L 3 is preferably selected as a single bond or from the group L-1 to L-13, wherein L-1 to L-13 may be substituted with one or more substituents R 1 1 , as described above.
  • the linker L 3 is particularly preferably selected from the group L-1 to L-7 and L-12, wherein L-1 to L-7 and L-12 may be substituted with one or more substituents R 1 1 , as described above.
  • the linker L 3 is particularly preferred from the group L-12, which may be substituted with one or more substituents R 11 , as previously described.
  • the linker L is preferably selected independently of one another as a single bond or from the group L-1 to L-13, wherein L-1 to L-13 may be substituted with one or more substituents R 1 1 , as previously described.
  • all linkers L are preferably single bonds.
  • substituents R 11 in (R 11 )x, (R 11 )y are preferably present as indicated below, most particularly preferably D.
  • the further matrix material it is selected from a combination of formulas (Aa-1), (Aa-2), (Aa-4), (Ad), (Ae) and (Af-1).
  • Ar 1 is used in each combination of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2) and (Af-3)
  • Ar 1 is used in each
  • Y 3 stands for O, S, NAr 4 or C(R # )2, preferably for O or NAr 4 ;
  • R# represents a methyl group or phenyl, which can be partially or completely deuterated, and where two substituents R# can represent a spirobifluorenyl group, which can be partially or completely deuterated, m represents 0 or 1 and
  • Ar* stands for phenyl, biphenyl or terphenyl, which may be partially or completely deuterated.
  • R# preferably stands for methyl
  • Y 3 preferably represents O or S, especially O.
  • m is preferably 0.
  • R 13 particularly preferably represents H, D, or a non-deuterated, partially or completely deuterated aryl group with 6 to 18 carbon atoms.
  • R 13 very preferably represents H, D, or non-deuterated, partially or completely deuterated phenyl.
  • R 13 very preferably represents H or D.
  • Ar 1 -1 to Ar 1 -12 the groups In Ar 1 -1, Ar 1 -2, Ar 1 -3, Ar 1 -9, Ar 1 -10, Ar 1 -11 and Ar 1 -12 are particularly preferred, with all symbols and indices having a meaning as previously described.
  • Preferred compounds of formula (B) are the compounds of formula (Ba), Formula (Ba), where Y, V 2 , L, R 10 , R 11 and a3 have a previously specified meaning, D corresponds to deuterium and a4 means 0, 1 or 2.
  • Particularly preferred compounds of formula (B) are the compounds of orme ( c), where Y, V 2 , L, R 10 , R 11 and a3 have a previously specified meaning, D
  • (Ba), (Bb) and (Bc) L is preferably a single bond.
  • Preferred compounds of formula (C) are the compounds of formula (Ca), Formula (Ca) where the symbols and indices for this formula (Ca) have the following meaning: W 1 is the same or different in each occurrence O, S, C(R W )2 or N-Ar 1 ;
  • #X is CR or NAr 1 , preferably NAr 1 ;
  • R w is, in each occurrence, either a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN; a3 is, in each occurrence, either 0, 1, 2, 3, or 4;
  • Ring B is derived from an aryl group with 6 to 20 ring atoms, which may be substituted with one or more substituents R##; where L, Ar 1 and R## have the meanings given above.
  • R 11 is the same or different in each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which may be partially or completely deuterated. can.
  • R 11 is the same or different in each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system with 6 to 30 ring atoms, which may each be partially or completely deuterated.
  • At least one of the other matrix materials is a deuterated compound
  • this at least one matrix material is a mixture of deuterated compounds with the same basic chemical structure, differing only in the degree of deuteration and/or the deuteration pattern.
  • deuterated mixtures and the preparation of deuterated materials as previously described for compounds of formula (I), apply accordingly.
  • this is a mixture of deuterated compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E), as previously described, wherein the average degree of deuteration of these compounds is at least 10 mol% to 100 mol%, preferably 50 mol% to 95 mol%, and particularly preferably 70 mol% to 90 mol%.
  • Suitable compounds of formula (A) are known, for example, from the following publications: W02007/077810A1, W02008/056746A1, W02010/136109A1, WO2011/057706A2, WO2011/160757A1, WO2012/023947A1, WO2012/048781 A1, WO2013/077352A1, WO2013147205A1, WO2013/083216A1, WO2014/094963A1, WO2014/007564A1, W02014/015931A1, W02015/090504A2, W02015/105251A1, WO2015/169412A1, WO2016/015810A1, WO2016/013875A1, W02016/010402A1, WO2016/033167A1, WO2017/178311A1, WO2017/076485A1, WO2017/186760A1, W02018/004096A1, WO2018/016742A1, WO2018/123783A1, WO2018/159964A1, WO
  • Particularly suitable compounds of formula (A) are compounds from WO2015/169412A1, described on pages 28 to 63, 93 and 110 to 114, compounds from W02019/007866A1, described in Tables 1 to 8 on pages 37 to 100, compounds from WO2019/096717A2, described in Table 1 on pages 27 to 33 and the compounds described on pages 96 to 102, compounds from W02019/229011A1, described in Tables 1 and 2 on pages 31 to 117 and compounds described on pages 251 to 254, compounds from W02021/037401A1, described on pages 31 to 64 and compounds P1 to P110 on pages 132 to 144, compounds from W02020/169241 A1, described in Table 1 on pages 30 to 73 and connections 1 to 36 and 67 to 81 on pages 74 to 78, as well as connections described on pages 223 to 231; connections from WO2023247662A1, described in Tables 1 and 2 on pages 18 to 23 and connections described on pages 100 to 102; connections from WO2023247663A1, described
  • Suitable compounds of formula (B) are known, for example, from the following publications: WO2015/182872A1, W02015/105316A1, WO2017/109637A1, W02018/060307A1, WO2018/151479A2, WO2018/088665A2, WO2018/060218A1, WO2018/234932A1, W02019/058200A1, W02019/017730A1, W02019/017731A1, WO2019/066282A1, WO2019/059577A1, WO2020/141949A1 W02020/067657A1, WO2022063744A1, W02022/090108A1, WO2022/207678A1, WO2023061998A1, KR20170139443A, KR20190036867A, KR2019035308A, KR2021147993A, CN110294753A, CN110437241A, US2016/072078A1, US2019/148646A1.
  • Suitable compounds of formula (C) are known, for example, from the following publications: W02017/160089A1, W02019/017730A1, WO2019/017731 A1, W02020/032424A1.
  • Suitable compounds of formula (E) are known, for example, from the following publications: WO2015/093878A1, WO2016/033167A1, WO2017/183859A1, WO2017/188655A1, WO2018/159964A1.
  • compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb) and/or (Bc) are particularly suitable, as described above or preferably, or corresponding compounds from the following tables that fall under these formulas.
  • suitable host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E) which can be combined according to the invention with the above-mentioned compounds as described above are the structures listed below in Tables 3 and 4.
  • Particularly suitable compounds of formulas (A), (Aa), (Ab), (Ac), (Ad), (Ae), (Af) and/or (B) which can be combined according to the invention with the above-mentioned compounds as described above, and in the The compounds E1 to E56 of Table 4 are used in the electroluminescent device or mixture according to the invention.
  • the host materials mentioned above according to the invention, as well as their preferably described embodiments, can be combined in the device according to the invention as desired with the aforementioned matrix materials/host materials, the matrix materials/host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E), as well as their preferably described embodiments of Table 3 or the compounds E1 to E56 of Table 4.
  • Particularly preferred mixtures of the compounds of formula (1) with the host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D), or (E) for the device according to the invention are obtained by combining compounds H1 to H30 with compounds E1 to E56.
  • Table 5 below shows particularly preferred mixtures.
  • the first mixture, M1 for example, is a combination of compound E1 with H1.
  • the concentration of the host material of formula (I), as previously described or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is typically in the range of 10 wt.% to 95 wt.%, preferably in the range of 15 wt.% to 90 wt.%, more preferably in the range of 15 wt.% to 80 wt.%, even more preferably in the range of 20 wt.% to 70 wt.%, most preferably in the range of 40 wt.% to 80 wt.% and most preferably in the range of 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer.
  • the concentration of the sum of all host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E), as previously or preferably described, in the inventive mixture or in the light-emitting layer of the inventive device is typically in the range of 5 wt.% to 90 wt.%, preferably in the range of 10 wt.% to 85 wt.%, more preferably in the range of 20 wt.% to 85 wt.%, even more preferably in the range of 30 wt.% to 80 wt.%, most preferably in the range of 20 wt.% to 60 wt.% and most preferably in the
  • the present invention also relates to a mixture which, in addition to the host materials of formula (I) mentioned above, hereinafter referred to as host material 1, and the host material of at least one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E), as previously described or preferably described, contains at least one phosphorescent emitter.
  • the present invention also relates to a mixture selected from a combination of compounds H1 to H30 with compounds E1 to E56 or mixtures M1 to M630, which contains at least one phosphorescent emitter.
  • the present invention also relates to an organic electroluminescent device as previously described or preferably described, wherein the light-emitting layer, in addition to the aforementioned host materials of the formula (1) and at least one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) and (E), as previously described or preferably described, in particular the material combinations M1 to M630, contains at least one phosphorescent emitter.
  • phosphorescent emitters typically encompasses compounds in which light emission occurs through a spin-forbidden transition from an excited state with a higher spin multiplicity, i.e., a spin state > 1, for example, through a transition from a triplet state or a state with an even higher spin quantum number, such as a quintet state.
  • a transition from a triplet state is preferred.
  • Suitable phosphorescent emitters are compounds that, upon suitable excitation, emit light, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and particularly preferably greater than 56 and less than 80, especially a metal with this atomic number.
  • Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphorescent emitters, especially compounds containing iridium or platinum.
  • all luminescent compounds containing the aforementioned metals are considered phosphorescent emitters.
  • all phosphorescent complexes are suitable, such as those used in phosphorescent OLEDs according to the prior art and as are known to those skilled in the art in the field of organic electroluminescence devices.
  • Preferred phosphorescent emitters according to the present invention correspond to formulas (1), (2), (3), (4) or (5), where the symbols and indices for these formulas (1), (2), (3), (4) and (5) are
  • Ri is H or D
  • R2 is H, D, F, CN or a branched or linear alkyl group with 1 to 10 C atoms or a partially or completely deuterated branched or linear alkyl group with 1 to 10 C atoms or a cycloalkyl group with 4 to 10 C atoms, which may be partially or completely substituted with deuterium.
  • Preferred phosphorescent emitters according to the present invention Formula (6), where the symbols and indices for this formula (6) have the following meanings: n+m is 3, n is 1 or 2, m is 2 or 1 ,
  • X is the same or different N or CR in each occurrence
  • R is the same or different in each occurrence H, D, F, CN or a branched or linear alkyl group with 1 to 10 C atoms or a partially or completely deuterated branched or linear alkyl group with 1 to 10 C atoms or a cycloalkyl group with 4 to 7 C atoms which may be partially or completely substituted with deuterium or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms which may be partially or completely substituted with deuterium.
  • n is preferably 1 and m is preferably 2.
  • emitters of formula (6) preferably one X is selected from N and the other X represent CR, or all X represent CR, either the same or different, in each occurrence.
  • at least one R is preferably different from H.
  • emitters of formula (6) preferably two R are different from H and have one of the meanings previously given for the emitters of formula (6).
  • Another object of the invention is therefore an organic electroluminescent device, as previously described or preferably described, characterized in that the light-emitting layer contains, in addition to the host materials 1 and 2, at least one phosphorescent emitter corresponding to one of formulas (1) to (6), as previously described, preferably to formula (6).
  • 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. These emitters are included in the description by reference.
  • each mixture is preferably selected from the sum of the mixtures M1 to M630 and combined with a compound of formulas (1) to (6) or a compound from Table 6.
  • the light-emitting layer in the organic electroluminescent device according to the invention comprising at least one phosphorescent emitter, is preferably an infrared-emitting, yellow, orange, red, green, blue or ultraviolet-emitting layer, particularly preferably a yellow or green-emitting layer, and most preferably a green-emitting layer.
  • a yellow emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 540 to 570 nm.
  • An orange emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 570 to 600 nm.
  • a red emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 600 to 750 nm.
  • a green emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 490 to 540 nm.
  • a blue emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 440 to 490 nm.
  • the photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, wherein the layer comprises the inventive combination of the host material 1 of formula (I) and the host material 2, consisting of at least one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) and (E), and the corresponding emitter.
  • the layer comprises the inventive combination of the host material 1 of formula (I) and the host material 2, consisting of at least one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6
  • the photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer.
  • the photoluminescence spectrum of the chosen emitter is typically measured in oxygen-free 10 ⁇ 5 molar solution at room temperature, and any solvent is suitable in which the chosen emitter dissolves. the specified concentration dissolves. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. Measurement is performed with a commercially available photoluminescence spectrometer.
  • Preferred phosphorescent emitters are therefore yellow emitters, preferably of formulas (1) to (6) or from Table 6, whose triplet energy T1 is preferably at ⁇ 2.3 eV to ⁇ 2.1 eV.
  • Preferred phosphorescent emitters are therefore green emitters, preferably of formulas (1) to (6) or from Table 6, whose triplet energy T1 is preferably at ⁇ 2.5 eV to ⁇ 2.3 eV.
  • Particularly preferred phosphorescent emitters are therefore green emitters, preferably of formulas (1) to (6) or from Table 6, as previously described, whose triplet energy T1 is preferably at ⁇ 2.5 eV to ⁇ 2.3 eV.
  • green emitters preferably of formulas (1) to (6) or from Table 6, as previously described, selected for the mixture or emitting layer according to the invention.
  • the light-emitting layer of the device or mixture according to the invention may also contain fluorescent emitters.
  • Preferred fluorescent emitting compounds are selected from the class of arylamines, wherein preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a condensed ring system, particularly preferably with at least 14 ring atoms.
  • Preferred examples are aromatic anthracene amines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines.
  • aromatic anthracene amine is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at position 9.
  • An aromatic anthracene diamine is understood to be a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at positions 9 and 10.
  • Aromatic pyrenamines, pyrendiamines, chrysenamines and chrysendiamines are defined analogously, with the diarylamine groups on the pyrene preferably located in the 1-position or in the 1,6-position. Position bound.
  • emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene arylamines are also preferred. Benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units are also preferred. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials exhibiting TADF (thermally activated delayed fluorescence).
  • TADF thermalally activated delayed fluorescence
  • the at least one light-emitting layer of the organic electroluminescent device can have three or four different matrix materials, preferably three different matrix materials.
  • These corresponding mixed-matrix systems can consist of the matrix materials described for host material 1 and host material 2, but they can also include, for example, wide-band-gap materials, bipolar host materials, electron transport materials (ETMs), or hole transport materials (HTMs) as a third or fourth matrix material, in addition to host material 1 or host material 2.
  • the mixed-matrix system is optimized for an emitter of formulas (1) to (6) or for an emitter from Table 6.
  • the mixture contains, in addition to the components of the host material of formula (I) and host material 2 as previously or preferably described, no further components, i.e., functional materials.
  • these are material mixtures used as such for the production of the light-emitting layer.
  • These mixtures are also referred to as premix systems, which are used as the sole material source during the deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during deposition. This allows for the simple and rapid deposition of a layer with a uniform distribution of components without the need for precise control of a multitude of material sources.
  • the mixture contains, in addition to the components of the host material of formula (I) and the host material 2 as previously described or preferably described, a phosphorescent emitter as previously described. With a suitable mixing ratio during evaporation, this mixture can also be used as the sole material source.
  • premix systems consisting of two matrix materials, namely a compound of formula (1) and a compound of one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E).
  • a compound of formula (1) consisting of two matrix materials, namely a compound of formula (1) and a compound of one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B),
  • premix systems consisting of three matrix materials, namely a compound of formula (1) and two compounds of one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E).
  • the components of the light-emitting layer of the device according to the invention can thus be processed by vapor deposition or from solution.
  • the material combination of the host materials 1 and 2, as previously or preferably described, optionally with the phosphorescent emitter, as previously or preferably described, is provided for this purpose in a formulation containing at least one solvent. Suitable formulations have been previously described.
  • the light-emitting layer in the device according to the invention, according to the preferred embodiments, and the emitting compound preferably contains between 99.9 and 1 vol.%, more preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, and most preferably between 97 and 80 vol.% of matrix material consisting of at least one compound of formula (1) and at least one compound of one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Aa-6), (Aa-7), (Aa-8), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (Bb), (Be), (C), (Ca), (D) or (E) according to the preferred embodiments, based on the total composition of emitter and matrix material.
  • the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%, and most preferably between 3 and 20 vol.% of the emitter, based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt.% are preferably used instead of the amounts in vol.% specified above.
  • the present invention also relates to an organic electroluminescent
  • the layer contains a hole injection layer (HIL) and/or a hole transport layer (HTL), whose hole-injecting material and hole-transporting material belong to the class of arylamines.
  • HIL hole injection layer
  • HTL hole transport layer
  • the sequence of layers in the organic electroluminescence device according to the invention is preferably the following:
  • This sequence of layers is a preferred sequence.
  • all materials used as electron transport materials in the electron transport layer according to the prior art can be used as materials for the electron transport layer.
  • aluminum complexes for example Alqa
  • zirconium complexes for example Zrq4
  • benzimidazole derivatives triazine derivatives
  • pyrimidine derivatives pyridine derivatives
  • pyrazine derivatives quinoxaline derivatives
  • quinoline derivatives quinoline derivatives
  • oxadiazole derivatives aromatic ketones
  • the present invention also relates to an organic electroluminescent device as previously or preferably described, wherein the organic layer comprises a hole injection layer (HIL) and/or a hole transport layer (HTL) and/or an electron blocking layer, the hole-injecting material and hole-transporting material of which is selected from the compounds of formula (1) as previously or preferably described.
  • HIL hole injection layer
  • HTL hole transport layer
  • electron blocking layer the hole-injecting material and hole-transporting material of which is selected from the compounds of formula (1) as previously or preferably described.
  • Suitable cathodes for the device according to the invention include metals with low work function, metal alloys, or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys of an alkali or alkaline earth metal and silver are also suitable, for example, a magnesium-silver alloy. In multilayer structures, additional metals with relatively high work functions, such as Ag or Al, can also be used, typically in combinations of these metals, such as Ca/Ag, Mg/Ag, or Ba/Ag.
  • a thin interlayer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor may also be preferred.
  • Suitable materials for this purpose include, for example, alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, T2O, BaFz, MgO, NaF, CsF, CS2CO3).
  • LiF, T2O, BaFz, MgO, NaF, CsF, CS2CO3 Lithium quinolinate
  • the thickness of this layer is preferably between 0.5 and 5 nm.
  • anodes Materials with a high work function are preferred as anodes.
  • the anode has a work function greater than 4.5 eV vs. vacuum.
  • Metals with a high redox potential such as Ag, Pt, or Au, are suitable for this purpose.
  • metal/metal oxide electrodes e.g., Al/Ni/NiOx, Al/PtOx
  • at least one of the electrodes must be transparent or semi-transparent to allow either the irradiation of the organic material (organic solar cell) or the extraction of light (OLED, O-LASER).
  • Preferred anode materials in this case are conductive mixed metal oxides.
  • ITO Indium tin oxide
  • IZO indium zinc oxide
  • Conductive doped organic materials are also preferred.
  • the anode can also consist of several layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • the organic electroluminescent device according to the invention is structured, contacted and finally sealed accordingly during its manufacture (depending on the application), since the lifetime of the devices according to the invention is shortened in the presence of water and/or air.
  • the manufacture of the device according to the invention is not limited in this respect. It is possible to coat one or more organic layers, including the light-emitting layer, using a sublimation process. In this process, the materials are deposited in vacuum sublimation systems at an initial pressure of less than 10 ⁇ 5 mbar, preferably less than 10 ⁇ 6 mbar. However, it is also possible for the initial pressure to be even lower, for example, less than 10 ⁇ 7 mbar.
  • the organic electroluminescence device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation.
  • the materials are coated at a pressure between 10 ⁇ 5 mbar. and applied at 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured.
  • a further preferred feature of the organic electroluminescent device according to the invention is that one or more organic layers containing the composition according to the invention are produced from solution, e.g., by spin coating, or by any printing process, e.g., screen printing, flexographic printing, nozzle printing, or offset printing, but particularly preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. Soluble host materials 1 and 2 and phosphorescent emitters are required for this purpose. Processing from solution has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively. This technique is particularly suitable for the mass production of organic electroluminescent devices.
  • Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.
  • a further object of the description is therefore a method for producing the organic electroluminescent device according to the invention, as previously described or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the hole injection layer and/or hole transport layer, is applied by vapor phase deposition, in particular with a sublimation process and/or with an OVPD (Organic Vapor Phase Deposition) process and/or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing process.
  • vapor phase deposition in particular with a sublimation process and/or with an OVPD (Organic Vapor Phase Deposition) process and/or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing process.
  • OVPD Organic Vapor Phase Deposition
  • the organic layer according to the invention preferably the light-emitting layer
  • the materials used can each be placed in a separate material source and then evaporated from the different material sources ("co-evaporation”).
  • the different materials can be premixed ("premixed,” premix systems) and The mixture is placed in a single material source from which it is then evaporated (“premix evaporation”). This allows for the simple and rapid deposition of the light-emitting layer with a uniform distribution of components, without the need for precise control of numerous material sources.
  • a method for producing the organic electroluminescent device according to the invention characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and/or hole-blocking layer, is applied by vapor deposition, in particular by a sublimation process and/or by an OVPD (Organic Vapor Phase Deposition) process and/or by means of carrier gas sublimation, or from solution, in particular by spin coating or by a printing process.
  • vapor deposition in particular by a sublimation process and/or by an OVPD (Organic Vapor Phase Deposition) process and/or by means of carrier gas sublimation, or from solution, in particular by spin coating or by a printing process.
  • OVPD Organic Vapor Phase Deposition
  • a method for producing the organic electroluminescent device according to the invention as previously described or preferably described, characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of formula (I) together with the other materials forming the light-emitting layer are deposited successively or simultaneously from at least two material sources from the gas phase.
  • a method for producing the device according to the invention characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of formula (I) together with at least one further matrix material as a premix, is deposited from the gas phase successively or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters and/or emitters exhibiting TADF (thermally activated delayed fluorescence).
  • TADF thermalally activated delayed fluorescence
  • the electronic devices according to the invention are characterized by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the
  • optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. This results in these devices exhibiting high PL and thus high EL efficiency of emitters, or excellent energy transfer from the matrices to dopants.
  • the compounds according to formula (I) or the preferred embodiments described above and below have a triplet level T1, which may, for example, be in the range of 2.40 eV to 2.90 eV.
  • a further object of the present invention is the use of a compound according to formula (I) or a mixture according to the invention in an organic electroluminescent device.
  • each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose.
  • each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.
  • Pd2(dba)3 with SPhos [657408-07-6] or tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2] can also be used as a catalyst system (palladium source and ligand).
  • the OLEDs listed in Table 7 are substrates made of glass platelets coated with 50 nm thick, structured ITO (indium tin oxide). The exact structure of the OLEDs is shown in Table 7. The materials required for fabricating the OLEDs are listed in Table 9, unless otherwise described earlier.
  • the emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (emitter), which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction.
  • a specification such as E3:H2:TEG2 (48%:40%:12%) 40nm means that material E3 is present in a volume fraction of 48% as host material 1, compound H2 as host material 2 in a fraction of 40%, and TEG2 in a fraction of 12% in a 40nm thick layer.
  • the hole injection layer (HIL) and the electron transport layer (ETL) can also consist of a mixture of two materials.
  • the OLEDs are characterized according to standard procedures. For this, the electroluminescence spectra and current-voltage-luminance (IUL) characteristics are measured, and the EQE is calculated from these measurements. The calculation assumes a Lambertian emission characteristic. EQE10 denotes the external quantum efficiency at a current density of 10 mA/ cm2 .
  • EQE (Ex) 100 * (EQE10(Ex) / EQE10(V)).
  • the lifetime LT90 is defined as the time after which the luminance, when operating at a constant current density jo in mA/ cm2, decreases from a starting luminance L0 (in cd/ m2 ) to 90% of this starting luminance.
  • the current density used is 80 mA/ cm2 .
  • the compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs.
  • Example V1 is a comparative example according to the prior art, while examples Ex1 to Ex10 show data for OLEDs according to the invention.
  • the examples according to the invention demonstrate, in particular, an advantage in the lifetime of the device.

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Abstract

La présente invention concerne des composés et des dispositifs électroniques organiques tels que des OLED (diodes électroluminescentes organiques) qui contiennent ces composés, par exemple en tant que matériaux de transport de trous et/ou matériaux de matrice, éventuellement combinés à un autre matériau de matrice. La présente invention concerne également des mélanges contenant ces composés.
PCT/EP2025/061312 2024-04-30 2025-04-25 Matériaux pour dispositifs électroniques organiques Pending WO2025228800A1 (fr)

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