EP4437814A1 - Matériaux pour dispositifs électroniques - Google Patents

Matériaux pour dispositifs électroniques

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Publication number
EP4437814A1
EP4437814A1 EP22821946.5A EP22821946A EP4437814A1 EP 4437814 A1 EP4437814 A1 EP 4437814A1 EP 22821946 A EP22821946 A EP 22821946A EP 4437814 A1 EP4437814 A1 EP 4437814A1
Authority
EP
European Patent Office
Prior art keywords
aromatic
radicals
substituted
atoms
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22821946.5A
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German (de)
English (en)
Inventor
Philipp Stoessel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP4437814A1 publication Critical patent/EP4437814A1/fr
Pending legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • 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
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/90—Ring systems containing bridged rings containing more than four rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and electronic devices, in particular organic electroluminescent devices containing these materials.
  • Organic-based charge transport materials e.g. triarylamine-based hole transporters
  • organic or polymer light-emitting diodes OLEDs or PLEDs
  • O-SC organic solar cells
  • O-FET organic field effect transistors
  • O-TFT organic thin-film transistors
  • O-IC organic switching elements
  • O-lasers organic laser diodes
  • Electronic devices within the meaning of this invention are understood to mean organic electronic devices which contain organic semiconductor materials as functional materials.
  • the electronic devices stand for electroluminescent devices such as OLEDs.
  • OLEDs in which organic compounds are used as functional materials are known to the person skilled in the art from the prior art.
  • OLEDs are electronic devices that have one or more layers that include organic compounds and emit light when a voltage is applied.
  • Electronic devices usually comprise a cathode, an anode and at least one functional, preferably emissive, layer. In addition to these layers, they can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge generation layers.
  • the hole transport layers and electron transport layers have a major influence on the performance data of electronic devices.
  • the object of the present invention is to provide compounds which are suitable for use in an electronic device, in particular an OLED, in particular as material for hole-transport layers or material for electron-transport layers, and lead to good properties there.
  • the present invention relates to a compound of the formula (1),
  • R 2 is the same or different on each occurrence and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more H atoms can also be replaced by D or F; two or more substituents R 2 can be linked to one another and form a ring; where at least one group R and/or R' is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can each be substituted by one or more R 1 radicals, with two or more R radicals preferably bonded to the same cycle can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1 .
  • An aryl group within the meaning of this invention contains 6 to 40 carbon atoms; a heteroaryl group within the meaning of this invention contains 5 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, 0 and/or S.
  • An aryl group or heteroaryl group is either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc.
  • Aromatics linked together by a single bond such as, for example Biphenyl, on the other hand, is not referred to as an aryl or heteroaryl group, but as an aromatic ring system.
  • An aromatic ring system within the meaning of this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms in the ring system.
  • a heteroaromatic ring system within the meaning of this invention contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 results.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system which does not necessarily only contain aryl or heteroaryl groups, but also in which several aryl or heteroaryl groups a non-aromatic moiety (preferably less than 10% of the non-H atoms), such as e.g. B. a C, N or O atom or carbonyl group can be connected.
  • systems are to be understood here, in which two or more aryl or heteroaryl groups are linked directly to one another, such as, for. B. biphenyl, terphenyl, bipyridine or phenylpyridine.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. should also be understood as aromatic ring systems for the purposes of this invention, and also systems in which two or more Aryl groups are linked, for example, by a linear or cyclic alkyl group or by a silyl group.
  • Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups and groups in which two or more aryl or heteroaryl groups are linked directly to one another, for example biphenyl, terphenyl, quaterphenyl or bipyridine, and fluorene or spirobifluorene .
  • An electron-rich heteroaromatic ring system is characterized in that it is a heteroaromatic ring system that does not contain any electron-deficient heteroaryl groups.
  • An electron-deficient heteroaryl group is a six-membered heteroaryl group containing at least one nitrogen atom or a five-membered heteroaryl group containing at least two heteroatoms, one of which is a nitrogen atom and the other is oxygen, sulfur or a substituted nitrogen atom, it being possible for further aryl or heteroaryl groups to be fused onto these groups.
  • electron-rich heteroaryl groups are five-membered-membered heteroaryl groups with exactly one heteroatom selected from oxygen, sulfur or substituted nitrogen, to which further aryl groups and/or further electron-rich five-membered-membered heteroaryl groups can be fused.
  • electron-rich heteroaryl groups are pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene or indenocarbazole.
  • An electron-rich heteroaryl group is also referred to as an electron-rich heteroaromatic radical.
  • An electron-poor heteroaromatic ring system is characterized in that it contains at least one electron-poor heteroaryl group, and more preferably no electron-rich heteroaryl groups.
  • alkyl group is used as a generic term both for linear or branched alkyl groups and for cyclic alkyl groups.
  • alkenyl group and alkynyl group are used as generic terms both for linear or branched alkenyl or alkynyl groups and for cyclic alkenyl or alkynyl groups.
  • a cyclic alkyl, alkoxy or thioalkoxy group in the context of this invention is understood as meaning a monocyclic, a bicyclic or a polycyclic group.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 40 carbon atoms, and in which individual H atoms or CH 2 groups are also substituted by the abovementioned groups can be, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methyl- pentyl, n
  • An alkoxy group OR 1 having 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s- Pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
  • a thioalkyl group SR 1 having 1 to 40 carbon atoms is, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopenten
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, it being possible for one or more non-adjacent CH2 groups to be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO2, preferably F, Cl or CN, particularly preferably F or CN.
  • an aromatic or heteroaromatic ring system with 5-60 aromatic ring atoms, preferably 5-40 aromatic ring atoms, which can also be substituted in each case with the above-mentioned radicals or a hydrocarbon radical and which can be linked via any positions on the aromatic or heteroaromatic are understood in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene , cis or trans indenofluorene, cis or trans indenocarbazole, cis or trans indolocarbazole
  • a maximum of two symbols X per cycle stand for N, particularly preferably a maximum of one symbol X.
  • no X is N.
  • the compound has no fused ring system formed by at least two R radicals.
  • the compound has no further CN groups apart from those explicitly listed in formula (1) or the preferred embodiments.
  • the dipole moment of the compound can be controlled by the CN groups.
  • the CN groups are not arranged in the same direction and not parallel to the C3 axis of the triptycene, ie not in the ortho position to R′ in each case on the same side of the triptycene.
  • only at most one CN group placed in such a position is not at its maximum.
  • the CN groups are arranged in such a way that the molecule has at least one mirror plane.
  • At least one group R is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 1 radicals, with two or more preferably attached to the radicals R bonded to the same cycle can together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which can be substituted by one or more radicals R 1 .
  • R, R', Ar', R 1 and R 2 are described below.
  • the preferences given below for R, R′, Ar′, R 1 and R 2 occur simultaneously and apply to the structures of the formula (1) and to all preferred embodiments listed above.
  • R is selected identically or differently on each occurrence from the group consisting of D, F, OR 1 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group can be substituted by one or more radicals R 1 , but is preferably unsubstituted, and where one or more non-adjacent CH 2 groups are replaced by O can be, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which can each be substituted by one or more radicals R 1 ; two R radicals can also form an aliphatic, aromatic or heteroaromatic ring system with one another.
  • R is particularly preferably selected identically or differently on each occurrence from the group consisting of F, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, in which case the alkyl group can be substituted by one or more radicals R 1 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1 non-aromatic radicals R 1 may be substituted.
  • R is very particularly preferably selected identically or differently on each occurrence from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is replaced by one or more radicals R 1 , preferably non-aromatic radicals R 1 , may be substituted.
  • R' is selected identically or differently on each occurrence from the group consisting of H, D, F, OR 1 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms -Atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group may be substituted by one or more radicals R 1 , but is preferably unsubstituted, and where one or more non-adjacent CH2 groups can be replaced by 0, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 ; two R radicals can also form an aliphatic, aromatic or heteroaromatic ring system with one another.
  • R' is particularly preferably selected identically or differently on each occurrence from the group consisting of H, D, F or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which is in each case replaced by one or more radicals R 1 , preferably non-aromatic radicals R 1 may be substituted.
  • R' is selected identically or differently on each occurrence from the group consisting of H, D or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which is in each case replaced by one or more radicals R 1 , preferably non-aromatic radicals R 1 may be substituted.
  • R and R' if they represent an aromatic or heteroaromatic ring system, are preferably selected from the groups of the following formulas R-1 to R-163, R1
  • R 1 has the meanings given above, the dashed bond represents the bond to formula (1) and the following also applies:
  • Ar 3 is identical or different on each occurrence and is a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which can be substituted by one or more R 1 radicals;
  • a 1 is identical or different on each occurrence, BR 1 , C(R 1 ) 2 , NR 1 , O or S, preferably C(R 1 ) 2 , BR 1 , NR 1 , O or S;
  • Ar 3 comprises divalent aromatic or heteroaromatic ring systems based on the groups of R-1 to R-163, where p is 0 and the dashed bond and an R 1 for the bond to the aromatic or heteroaromatic group after R-1 until R-163 stands.
  • the substituent R 1 which is bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more R 2 radicals.
  • this substituent R 1 is identical or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, which no fused aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are fused directly to one another, and which can each also be substituted by one or more radicals R 2 .
  • phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35 it being possible for these structures to be substituted by one or more radicals R 1 , but they are preferably unsubstituted.
  • a 1 is C(R 1 ) 2
  • the substituents R 1 bonded to this carbon atom are preferably identical or different on each occurrence for a linear alkyl group having 1 to 10 carbon atoms or for a branched or cyclic alkyl group with 3 to 10 carbon atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 .
  • R 1 very particularly preferably represents a methyl group or a phenyl group.
  • the radicals R 1 can also form a ring system with one another, which leads to a spiro system.
  • R 1 is selected identically or differently on each occurrence from the group consisting of H, D, F, OR 2 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, it being possible for the alkyl or alkenyl group to be substituted by one or more R 2 radicals and for one or more non-adjacent CH2 groups to be replaced by O , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 ; two or more radicals R 1 can form an aliphatic ring system with one another.
  • R 1 is the same or different on each occurrence selected from the group consisting of H, a straight-chain alkyl group with 1 up to 6 carbon atoms, in particular with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group can be substituted with one or more radicals R 2 , but is preferably unsubstituted is, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 , but is preferably unsubstituted.
  • R 2 is the same or different on each occurrence of H, F, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms which is linked to an alkyl group having 1 to 4 carbon atoms. Atoms may be substituted, but is preferably unsubstituted.
  • all radicals R 1 if they represent an aromatic or heteroaromatic ring system, or R 2 if they represent aromatic or heteroaromatic groups, are selected from the groups R-1 to R-163, which, however, then are each substituted accordingly with R 2 or the groups mentioned for R 2 .
  • radicals R do not form any further aromatic or heteroaromatic groups fused onto the basic structure of the formula (1).
  • the alkyl groups in compounds according to the invention which are processed by vacuum evaporation preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms, very particularly preferably no more than 1 carbon atom.
  • the preferred embodiments mentioned above can be combined with one another at will within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously.
  • the compounds according to the invention can be prepared by synthesis steps known to those skilled in the art, such as, for. B. bromination, Suzuki coupling, Ullmann coupling, Heck reaction, Hartwig-Buchwald coupling, cyanation, etc., are shown.
  • a further subject of the present invention is therefore a process for preparing the compounds according to the invention, characterized by the following steps:
  • the compounds according to the invention can, starting from bis- or triscyanotriptycenes known from the literature, by mono-, di- or tri-halogenation (iodination, bromination, chlorination) directionally in the ortho position to the CN groups, under palladium catalysis with N- Halogenimides, such as N-halosuccinimides, are halogenated, for example analogously to B. Du et al., J. Org. Chem. 2013, 78, 2786, see scheme 1. Hydroxy-substituted bis- or triscyanotriptycenes known from the literature can be carried out according to standard methods known from the literature, e.g. B.
  • triptycene halides or triflates can be borylated by reaction with B 2 Pin 2 under palladium catalysis in the presence of a phosphine (e.g. dppf, PCy 3 , S-Phos) and a base, typically potassium acetate. See Scheme 2. Both the halides, the triflates and the boronic esters can be further functionalized using standard methods via CC (e.g. Suzuki) or CN (e.g. Buchwald or Ullmann) coupling, see Scheme 3.
  • CC e.g. Suzuki
  • CN e.g. Buchwald or Ullmann
  • Formulations of the compounds according to the invention are required for the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene , (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4 -Methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclo- Hexanol, cyclohexanone, cyclohexylbenzene, decalin,
  • a further subject matter of the present invention is therefore a formulation, in particular a solution, dispersion or emulsion, comprising at least one compound according to the invention and at least one further compound.
  • the further connection can be, for example, a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. The preparation of such solutions is known to the person skilled in the art and is described, for example, in WO 2002/072714, WO 2003/019694 and the literature cited therein.
  • the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and/or a matrix material.
  • This further connection can also be polymeric.
  • the compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device (OLED). Depending on the substitution, the compounds can be used in different functions and layers.
  • OLED organic electroluminescent device
  • a further object of the present invention is therefore the use of a connection according to the invention in an electronic device.
  • Yet another subject matter of the present invention is an electronic device containing at least one connection according to the invention.
  • the compounds according to the invention can be present as a racemate or as a pure enantiomer, in particular when they are used.
  • An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or also layers that are made up entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs). ), organic laser diodes (O-lasers) and organic plasmon emitting devices, but preferably organic electroluminescent devices (OLEDs).
  • O-ICs organic integrated circuits
  • O-FETs organic field effect transistors
  • OF-TFTs organic thin-film transistors
  • O-LETs organic light-emitting transistors
  • O-SCs organic solar cells
  • DSSCs dye-sensitized organic solar cells
  • organic optical detectors organic photo
  • the device is particularly preferably an organic electroluminescent device comprising cathode, anode and at least one emitting layer, wherein at least one organic layer, which can be an emitting layer, hole transport layer, electron transport layer, hole blocking layer, electron blocking layer or another functional layer, at least one compound of the invention includes.
  • the layer depends on the substitution of the compound.
  • the organic electroluminescent device can also contain further layers, for example one each or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers (charge generation layers) and/or organic or inorganic p/n transitions.
  • interlayers can be introduced between two emitting layers, which have an exciton-blocking function, for example.
  • each of these layers does not necessarily have to be present.
  • the organic electroluminescence device can contain an emitting layer, or it can contain a plurality of emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in white emission overall, i. H. in the emitting layers different emitting compounds are used which can fluoresce or phosphoresce. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green and orange or red emission (the basic structure is described, for example, in WO 2005/011013).
  • the organic electroluminescence device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.
  • the compound of the formula (1) is preferably used in an organic electroluminescent device which comprises one or more phosphorescent emitters.
  • the compound according to the invention according to the embodiments listed above can be used in different layers, depending on the exact structure.
  • the organic electroluminescence device can contain an emitting layer or it can contain a plurality of emitting layers, with at least one layer containing at least one compound according to the invention. Furthermore, the compound of the invention in an electron transport layer and / or in a Hole blocking layer and/or in a hole transport layer and/or in an exciton blocking layer.
  • phosphorescent compound typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g. B. a transition from a triplet excited state or a state with a higher spin quantum number, e.g. B. a quintet state.
  • Suitable phosphorescent compounds are, in particular, compounds which, when suitably excited, emit light, preferably in the visible range, and also at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 included. All luminescent complexes with transition metals or lanthanides are considered to be preferred as phosphorescent compounds, particularly if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold or europium, particularly compounds containing indium, contain platinum or copper. In the context of the present invention, all luminescent indium, platinum or copper complexes are considered to be phosphorescent emitting compounds.
  • Examples of the emitter described above can be registered where 00/70655, where 2002/02714, WO 2002/15645, EP 1191612, EP 1191614, WO 05/019373, US 2005/ 0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO 2011/032626, WO 2011/ 066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/117718, WO 2016/ 015815, WO 2016/124304, WO 2017/032439, WO 2018/011186, WO 2018/041769, WO 2019/020538, WO 2018/178
  • all phosphorescent complexes such as those according to the prior art are suitable are used for phosphorescent OLEDs and as are known to the person skilled in the field of organic electroluminescence, and the person skilled in the art can use further phosphorescent complexes without any inventive step. It is also possible for a person skilled in the art, without any inventive activity, to use further phosphorescent complexes in combination with the compounds of the formula (1) in organic electroluminescent devices. Further examples are listed in a table below.
  • the compound of formula (1) in an electronic device which contains one or more fluorescent emitting compounds.
  • the compounds of the formula (1) are used as hole-transporting material.
  • the compounds are preferably contained in a hole-transport layer, an electron-blocking layer or a hole-injection layer. Use in an electron blocking layer is particularly preferred.
  • a hole-transporting layer within the meaning of the present application is a layer with a hole-transporting function between the anode and the emitting layer.
  • hole-injection layers and electron-blocking layers are understood as meaning specific embodiments of hole-transport layers.
  • a hole-injection layer is a hole-transport layer which is directly adjacent to the anode or is only separated from the anode by a single coating.
  • an electron blocking layer is that hole transport layer which is directly adjacent to the emitting layer on the anode side.
  • the OLED according to the invention preferably comprises two, three or four hole-transporting layers between the anode and the emitting layer Layers of which preferably at least one, particularly preferably precisely one or two, contain a compound of the formula (1).
  • the compound of the formula (1) is used as a hole transport material in a hole transport layer, a hole injection layer or an electron blocking layer, the compound can be used as a pure material, i. H. in a proportion of 100%, can be used in the hole transport layer, or it can be used in combination with one or more other compounds.
  • the organic layer which contains the compound of the formula (1) then additionally contains one or more p-type dopants.
  • P-type dopants used in accordance with the present invention are preferably those organic electron-accepting compounds capable of oxidizing one or more of the other compounds in the mixture.
  • p-dopants are those in WO 2011/073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO 2009/00 3455, WO 2010/094378, WO 2011/120709, US 2010/0096600, WO 2012/095143 and DE 102012209523.
  • Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenylenes, azatriphenylenes, l 2 , metal halides, preferably transition metal halides, metal oxides, preferably metal oxides, which contain at least one transition metal or a metal of main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as a binding site.
  • Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re 2 O 7 , MoO 3 , WO 3 and ReO 3 .
  • the p-type dopants are preferably present in a substantially homogeneous distribution in the p-type layers. This can e.g. B. be achieved by co-evaporation of the p-dopant and the hole transport material matrix.
  • Preferred p-dopants are in particular the following compounds:
  • the compound of the formula (1) is used as a hole-transport material in combination with a hexaazatriphenylene derivative, as described in US 2007/0092755.
  • the hexaazatriphenylene derivative is particularly preferably used here in a separate layer.
  • the compound of the formula (1) is used in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent compounds.
  • the proportion of the matrix material in the emitting layer is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume, particularly preferably between 92.0 and 99.5% by volume -%. for fluorescent emitting layers and between 85.0 and 97.0% by volume for phosphorescent emitting layers.
  • the proportion of the emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume, particularly preferably between 0.5 and 8.0% by volume for fluorescent ones emissive layers and between 3.0 and 15.0% by volume. for phosphorescent emitting layers.
  • An emitting layer of an organic electroluminescence device can also comprise systems that contain a large number of matrix materials (mixed matrix systems) and/or a large number of emitting compounds.
  • the emitting compounds are usually those that have the smaller proportion in the system and the matrix materials are those that have the larger proportion in the system.
  • the proportion of a single matrix material in the system can be lower than the proportion of a single emitting compound.
  • the compounds of the formula (1) are preferably used as a component of mixed matrix systems.
  • the mixed matrix systems preferably consist of two or three different matrix materials, particularly preferably two different matrix materials. In this case, one of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties.
  • the compound of formula (1) is preferably the matrix material with hole-transporting properties.
  • the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely combined in a single mixed matrix component, with the other mixed matrix component(s) fulfilling (fulfilling) other functions.
  • the two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1 and most preferably 1:4 to 1:1.
  • Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. A source for more detailed information on mixed matrix systems is the application WO 2010/108579.
  • the mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds.
  • mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices.
  • Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent compounds mentioned below or the preferred matrix materials for fluorescent compounds, depending on which type of emitting compound is used in the mixed matrix system becomes.
  • Preferred phosphorescent compounds for use in mixed matrix systems are the same as described above generally preferred phosphorescent emitter materials described.
  • Examples of phosphorescent compounds are listed below.
  • Preferred fluorescent emitting compounds are selected from the class of arylamines.
  • an arylamine or an aromatic amine is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems which are bonded directly to the nitrogen.
  • at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms.
  • Preferred examples of these are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
  • aromatic anthracenamine is understood as meaning a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • aromatic anthracenediamine a compound is to be understood in which two diarylamino groups are bonded directly to an anthracene group, preferably in positions 9, 10.
  • Aromatic pyreneamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously, in which the diarylamino groups are bonded to the pyrene preferably in the 1-position or 1,6-position are.
  • emitting compounds are indenofluorenamines or fluorenediamines, for example according to WO 2006/108497 or WO 2006/122630, benzoindenofluorenamines or -fluorenediamines, for example according to WO 2008/006449, and dibenzoindenofluorenamines or -diamines, for example according to WO 2007/ 140847 and the indenofluorene derivatives with fused aryl groups disclosed in WO 2010/012328.
  • the pyrenearylamines disclosed in WO 2012/048780 and in WO 2013/185871 are also preferred.
  • benzoindenofluorenamines disclosed in WO 2014/037077 are also preferred.
  • the benzofluorenamines disclosed in WO 2014/106522 are also preferred.
  • the extended benzoindenofluorenes disclosed in WO 2014/111269 and in WO 2017/036574 are also preferred.
  • the extended benzoindenofluorenes disclosed in WO 2017/028940 and in WO 2017/028941 disclosed phenoxazines and disclosed in WO 2016/150544 fluorine derivatives bonded to furan units or to thiophene units.
  • Useful matrix materials include materials from different classes of substances.
  • Preferred matrix materials are selected from the classes of oligoaryls (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoaryls with fused aromatic groups, the oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461) , the polypodal metal complexes (e.g. according to WO 2004/081017), the hole-conducting compounds (e.g.
  • the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides etc. (e.g. according to WO 2005/084081 and WO 2005/084082 ), the atropisomers (for example according to WO 2006/048268), the boronic acid derivatives (for example according to WO 2006/117052) or the benzanthracenes (for example according to WO 2008/145239).
  • Particularly preferred matrix materials are selected from the classes of oligoarylenes with naphthalene, anthracene, benzanthracene and/or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides.
  • Very particularly preferred matrix materials are selected from the classes of oligoarylenes, which include anthracene, benzanthracene, benzophenanthrene and/or pyrene or atropisomers of these compounds.
  • an oligoarylene is a compound in which at least three aryl or arylene groups are connected to one another.
  • WO 2006/097208, WO 2006/131192, WO 2007/065550, WO 2007/110129, WO 2007/065678, WO 2008/145239, WO 2009/100925, WO 2011/054442 and EP 155 3154 disclosed anthracene derivatives, the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012/0187826, the benzanthracenylanthracene compounds disclosed in WO 2015/158409, the indenobenzofurans disclosed in WO 2017/025165 and the phenanthrylanthracenes disclosed in WO 2017/036573.
  • Preferred matrix materials for phosphorescent compounds are, as are compounds of the formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B. CBP (N, N-bis carbazolylbiphenyl) or WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, z. B.
  • CBP N, N-bis carbazolylbiphenyl
  • WO 2005/039246 US 2005/0069729, JP 2004/288381
  • WO 2012/048781 lactams, z. B. according to WO 2011/116865 or WO 2011/137951, or dibenzofuran derivatives, z. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as for example in WO 2010/108579 described.
  • Examples of suitable hole-transporting matrix materials are the structures listed in the table below.
  • Suitable charge transport materials such as can be used in the hole injection or hole transport layer or in the electron blocking layer or in the electron transport layer of the electronic component according to the invention, in addition to the compounds of the formula (1), for example those in Y. Shirota et al., Chem. Rev 2007, 107(4), 953-1010, or other materials used in these prior art layers.
  • the OLED according to the invention preferably comprises two or more different hole-transporting layers.
  • the compound of the formula (1) can be used in one or more or in all hole-transporting layers.
  • the compound of the formula (1) is used in exactly one or exactly two hole-transporting layers, and other compounds, preferably aromatic amine compounds, are used in the other hole-transporting layers present.
  • Further compounds which, in addition to the compounds of the formula (1), are preferably used in hole-transporting layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (eg according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene Derivatives (e.g.
  • WO 01/049806 amine derivatives with fused aromatics
  • spirobifluorenamines for example according to WO 2012/034627 or WO 2013/120577
  • Fluorenamines for example according to WO 2014/015937, WO 2014/015938, WO 2014/015935 and WO 2015/082056)
  • spirodibenzopyranamines for example according to WO 2013/083216
  • dihydroacridine derivatives for example according to WO 2012/150001
  • Spirodibenzofuran and Spirodibenzo- thiophene for example after where 2015/022051, where 2016/102048 and where 2016/131521)
  • phenanthrendialylamine for example according to Wo 2015/131976)
  • Spirotribenzotropolone for example according to where 2016/087017
  • spirobifluorenes substituted by diarylamino groups in the 4-position is very particularly preferred, in particular the use of those compounds which are claimed and disclosed in WO 2013/120577 and the use of diarylamino groups in the 2-position substituted spirobifluorenes as hole-transporting compounds, in particular the use of those compounds which are claimed and disclosed in WO 2012/034627.
  • Aluminum complexes e.g. Alq3, zirconium complexes, e.g. Zrq4, lithium complexes, e.g. Liq, 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.
  • Other suitable materials are derivatives of the aforementioned compounds, as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
  • an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process.
  • the materials are vapour-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.
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated using the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • OVPD organic vapor phase deposition
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured.
  • an organic electroluminescent device characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing method, such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or nozzle printing.
  • any printing method such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or nozzle printing.
  • Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited. These methods are generally known to the person skilled in the art and can be applied to organic electroluminescent devices comprising the compounds according to the invention without any inventive step.
  • the electronic devices containing one or more compounds of the formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications (e.g. light therapy).
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished by one or more of the following properties:
  • the compounds according to the invention lead to high efficiencies, in particular to a high EQE.
  • the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that may have multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as representative.
  • Desiccant is filtered off over a silica gel bed pre-slurried with DCM, the filtrate is concentrated in vacuo and the distilled DCM is successively replaced with about 200 ml of methanol, the product which has crystallized out is filtered off with suction, washed with a little methanol and dried in vacuo. Further purification is carried out in each case by repeated hot extraction crystallization (customary organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractionated sublimation or tempering in a high vacuum. Yield: 20.7 g (34 mmol) 68%; Purity: approx. 99.9% according to HPLC.
  • reaction of the boron esters S300 to S312, S400, S500 and S501 is carried out analogously using tetrakistriphenylphosphinopalladium(O) in DMSO or S-Phos/Pd(OAc) 2 (2:1) in toluene: dioxane: water ( 4:1 :4, vvv).
  • the residue is taken up in 1000 ml DCM, filtered through a bed of silica gel preslurried with DCM, and the filtrate is washed twice with 300 ml of 10% ammonia solution, twice with 300 ml of water each time, once with it 200 ml total saline solution and dried over sodium sulfate.
  • Desiccant is filtered off over a silica gel bed pre-slurried with DCM, the filtrate is slowly concentrated on a rotary evaporator, the DCM which has been distilled off is successively replaced with approx.
  • OLEDs according to the invention and OLEDs according to the prior art are produced using a general method according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the compounds T according to the invention can be used in the electron transport layer (ETL) and the hole blocking layer (HBL). All materials are thermally evaporated in a vacuum chamber.
  • the emission layer (EML) always consists of at least one matrix material (host material, host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is added to the matrix material or matrix materials by co-evaporation in a certain volume fraction is added.
  • a specification such as SMB:D (97:3%) means that the material SMB is present in the layer in a volume proportion of 97% and the dopant D in a proportion of 3%.
  • the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance are calculated from current-voltage-luminance characteristics (IUL characteristics) below assumption of a Lambertian radiation characteristic and the service life.
  • the EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd/m 2
  • the service life is determined at an initial luminance of 10000 cd/m 2 .
  • the LT80 in (h) is the measured time in which the brightness has fallen to 80% of the initial brightness.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • Emission layer see Table 1
  • HBL Hole Blocker Layer
  • Electron transport layer see Table 1
  • the compounds according to the invention can be used in the electron transport layer (ETL), the hole blocking layer (HBL) and in the emission layer (EML) as matrix material (host material, host material) M (see Table 5) or T (see materials according to the invention).
  • matrix material host material, host material
  • EML emission layer
  • all materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is admixed to the matrix material or matrix materials by co-evaporation in a certain proportion by volume.
  • a specification such as M1 :M2:lr (55%:35%:10%) means that the material M1 accounts for 55% by volume, M2 for 35% by volume and Ir for 10% by volume in the layer present.
  • the electron transport layer can also consist of a mixture of two materials.
  • the exact structure of the OLEDs can be found in Table 3.
  • the materials used to fabricate the OLEDs are shown in Table 5.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance are calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic and the service life.
  • the specification of the EQE in (%) and the voltage in (V) takes place at a luminance of 1000 cd/m 2
  • the service life is at an initial luminance of 1000 cd/m 2 for blue and red, 10000 cd/m 2 for green and yellow emitting components.
  • the specification LT80 in (h) is the measured time in which the brightness falls to 80% of the initial brightness.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • EBL Electron blocking layer
  • HBL Hole blocking layer
  • EML Electron injection layer
  • HBL Hole blocking layer
  • ETL Electron injection layer
  • EIL Electron injection layer

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  • Organic Chemistry (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne des composés qui sont appropriés pour être utilisés dans des dispositifs électroniques, et des dispositifs électroniques, plus particulièrement des dispositifs électroluminescents organiques, contenant ces composés.
EP22821946.5A 2021-11-25 2022-11-23 Matériaux pour dispositifs électroniques Pending EP4437814A1 (fr)

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