EP3888147A1 - Composés pour dispositifs électroniques - Google Patents

Composés pour dispositifs électroniques

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Publication number
EP3888147A1
EP3888147A1 EP19809485.6A EP19809485A EP3888147A1 EP 3888147 A1 EP3888147 A1 EP 3888147A1 EP 19809485 A EP19809485 A EP 19809485A EP 3888147 A1 EP3888147 A1 EP 3888147A1
Authority
EP
European Patent Office
Prior art keywords
aromatic ring
atoms
ring systems
groups
radicals
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
EP19809485.6A
Other languages
German (de)
English (en)
Inventor
Amir Hossain Parham
Jens ENGELHART
Christian EICKHOFF
Christian Ehrenreich
Jonas Valentin Kroeber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP3888147A1 publication Critical patent/EP3888147A1/fr
Pending legal-status Critical Current

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    • 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
    • C07D487/16—Peri-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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D471/22—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 systems contains four or more hetero rings
    • 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
    • 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
    • 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
    • C07D487/22—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 four or more hetero rings
    • 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
    • C07D495/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/18—Carrier blocking layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present application relates to certain N-heteroaromatic
  • connections are suitable for use in electronic devices.
  • Organic electronic devices which are organic semiconductor materials
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • the term OLEDs is understood to mean electronic devices which have one or more layers containing organic compounds and which emit light when electrical voltage is applied.
  • the structure and the general principle of operation of OLEDs are known to the person skilled in the art.
  • Devices have emissive layers, in particular
  • phosphorescent emissive layers New compounds are still being sought for use in these layers, in particular compounds which can serve as matrix material in an emitting layer.
  • compounds are sought which have a high glass transition temperature TG and a high oxidation and temperature Have stability, in particular high oxidation and temperature stability.
  • Devices are suitable, in particular for use in OLEDs, again particularly for use as matrix materials for
  • Compounds have a high glass transition temperature TG and a high oxidation and temperature stability.
  • the subject of the present application is an electronic one
  • Z 1 is the same or different at each occurrence C, CR 1 or N;
  • Z 2 is the same or different at each occurrence C, CR 2 or N;
  • Ar 1 is selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with one or more radicals R 3 and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with one or more radicals R 3 ;
  • a circle within a six- or five-membered ring means that the ring in question is aromatic or
  • the definition Z 1 C means that the structural element of the formula (I) is part of a larger condensed ring system
  • An aryl group in the sense of this invention is understood to mean either a single aromatic cycle, that is to say benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or anthracene.
  • a condensed aromatic polycycle consists of two or more together condensed individual aromatic cycles. Condensation between cycles means that the cycles share at least one edge with one another.
  • An aryl group in the sense of this invention contains 6 to 40 aromatic ring atoms, none of which is a hetero atom.
  • a heteroaryl group means either a single heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a condensed heteroaromatic polycycle, for example quinoline or carbazole.
  • a condensed heteroaromatic polycycle exists in the sense of the present
  • Heteroaryl group in the sense of this invention contains 5 to 40 aromatic ring atoms, at least one of which represents a hetero atom.
  • the heteroatoms of the heteroaryl group are preferably selected from N, O and S.
  • radicals mentioned can be understood to mean, in particular, groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene,
  • An aromatic ring system in the sense of this invention is a system which does not necessarily only contain aryl groups, but which can additionally contain one or more non-aromatic rings which are condensed with at least one aryl group. Not this one
  • aromatic rings contain only carbon atoms as
  • Ring atoms examples of groups included in this definition are tetrahydronaphthalene, fluorene and spirobifluorene.
  • aromatic ring system also includes systems which consist of two or more aromatic ring systems which are connected to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl and 3,5-diphenyl-1-phenyl.
  • An aromatic ring system in the sense of this invention contains 6 to 40 carbon atoms and no heteroatoms in the ring system.
  • the definition of “aromatic ring system” does not include heteroaryl groups.
  • a heteroaromatic ring system corresponds to that mentioned above
  • Ring system not only contain aryl groups and heteroaryl groups, but one or more can not
  • Heteroaryl group are condensed.
  • the non-aromatic rings can contain only carbon atoms as ring atoms, or they can additionally contain one or more heteroatoms, the
  • Heteroatoms are preferably selected from N, O and S.
  • An example of such a heteroaromatic ring system is benzopyranyl.
  • the term “heteroaromatic ring system” is understood to mean systems which consist of two or more aromatic or heteroaromatic ring systems which are linked to one another via single bonds
  • Heteroaromatic ring system in the sense of this invention contains 5 to 40 ring atoms which are selected from carbon and heteroatoms, at least one of the ring atoms being a heteroatom.
  • the heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S.
  • an aromatic ring system cannot have a hetero atom as a ring atom, whereas a heteroaromatic ring system must have at least one hetero atom as a ring atom.
  • This heteroatom can be used as a ring atom of a non-aromatic heterocyclic ring or as a ring atom of one
  • each aryl group is included in the term “aromatic ring system” and each heteroaryl group is included in the term “heteroaromatic ring system”.
  • Ring atoms or a heteroaromatic ring system with 5 to 40 aromatic ring atoms are understood in particular to be groups which are derived from the groups mentioned above under aryl groups and heteroaryl groups and from biphenyl, terphenyl, quaterphenyl, fluorene, Spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxes, spirotruxes, spiroisotruxes,
  • a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms in which also individual H atoms or Chh groups can be substituted by the groups mentioned above when defining the radicals, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t- Butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neo-pentyl, n-hexyl, cyclohexyl, neo-hexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethyl, n-propy
  • radicals can be substituted, preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2nd -Methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n -Butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s
  • Hexinylthio, heptinylthio or octinylthio understood.
  • the wording that two or more radicals can form a ring with one another is to be understood, inter alia, to mean that the two radicals are linked to one another by a chemical bond.
  • the above-mentioned formulation should also be understood to mean that in the event that one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring.
  • Ar 1 is preferably selected the same or different for each occurrence from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthalene, fluorene, benzofluorene,
  • Ar 1 can be selected the same or different for each occurrence from combinations of groups derived from benzene, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene , Benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran,
  • Benzimidazole quinazoline, quinoxaline, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, where the groups can each be substituted by one or more radicals R 3 .
  • Ar 1 is particularly preferably selected the same or different from phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, Naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, triazinyl, pyrimidyl, pyridyl, quinazoline, quinoxaline and quinoline, where the groups mentioned can each be substituted by one or more radicals R 3 .
  • no more than one group Z 1 per formula is N, and the other groups Z 1 are selected from C and CR 1 .
  • Z 1 is preferably selected the same or different from C and CR 1 for each occurrence.
  • no more than one group Z 2 per formula is N, and the other groups Z 2 are selected from C and CR 2 .
  • Z 2 is preferably selected the same or different from C and CR 2 at each occurrence.
  • K is preferably 0.
  • R 1 is preferably selected identically or differently from H, D, F, CN, Si (R 4 ) 3, N (R 4 ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and
  • R 1 is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic
  • Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R 4 .
  • Each occurrence of R 2 is preferably selected identically or differently from H, D, F, CN, Si (R 4 ) 3, N (R 4 ) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and
  • R 2 is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic
  • Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R 4 .
  • R 3 is preferably selected identically or differently from H, D, F, CN, Si (R 4 ) 3, N (R 4 ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and
  • R 3 is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring systems Ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic
  • Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R 4 .
  • R 4 is preferably selected identically or differently from H, D, F, CN, Si (R 5 ) 3, N (R 5 ) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and
  • R 5 is preferably equal to H.
  • Formula (I) preferably corresponds to one of the following formulas:
  • Z 1 is the same or different C or CR 1 on each occurrence. According to an alternative preferred embodiment
  • the embodiment is exactly one group Z 1 per formula equal to N, and the remaining groups Z 1 are the same or different C or CR 1 each time they occur.
  • Z 2 is the same or different C or CR 2 on each occurrence.
  • exactly one group Z 2 per formula is N, and the remaining groups Z 2 are the same or different C or CR 2 on each occurrence.
  • Z 1 is the same or different C or CR 1 on each occurrence
  • Z 2 is the same on each occurrence or different C or CR 2 .
  • Z 1 is on each occurrence, identically or differently, C or CR 1
  • Z 2 and precisely one group per formula is equal to N
  • the remaining groups Z 2 are on each occurrence, identically or differently, C or CR. 2
  • Ar 2 is selected from aromatic ring systems with 4 to 40 aromatic ring atoms which are substituted with radicals R A and heteroaromatic ring systems with 3 to 40 aromatic ring atoms which are substituted with radicals R A , and wherein Z 1 is the same or different on each occurrence Is CR 1 or N and the other symbols are defined as above.
  • Ar 2 is preferably an aromatic ring system with 4 aromatic
  • Ring atoms which are substituted by radicals R A that is, condensed benzene, which is substituted with radicals R A.
  • the group Ar 2 shown in formulas (I-3) to (1-14) and (1-18) to (I-20) above is fused to the five-ring and six-ring, respectively, just like a benzene group to one in a naphthalene group other benzene group is fused by both benzene groups sharing two carbon atoms and the bond between them.
  • Ar 2 is a unit C4FI4 derived from a benzene ring.
  • R A is preferably selected identically or differently from H, D, F, CN, Si (R 4 ) 3, N (R 4 ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40
  • aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and
  • Alkoxy groups the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R 4 .
  • Z 1 is preferably equal to CR 1 .
  • exactly one group Z 1 per formula is N, and the remaining groups Z 2 are CR 1 .
  • aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 4 (radical A), - Heteroaromatic ring systems with 5 to 40 aromatic
  • Residues A are preferably selected the same or different at each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthyl, fluorenyl and spirobifluorenyl, each of which is substituted by radicals R A.
  • radicals B are preferably selected identically or differently from dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, triazinyl, pyrimidyl, pyridyl, quinazolinyl, quinoxalinyl and quinolinyl, each of which is substituted by radicals R A.
  • Exactly one group R 1 , R 2 , R 3 or R A is preferably present in the formulas (1-1) to (I-20) above, which is selected from the above-mentioned radicals A, B or C. Particularly preferred in this case the other existing groups R 1 , R 2 , R 3 and R A are equal to Fl.
  • connection corresponds to the following formulas the symbols which occur are as defined above and preferably correspond to their preferred embodiments mentioned above.
  • all groups R 1 are preferably the same H.
  • All groups R 2 are also preferably H.
  • All groups R 3 are H.
  • Also preferred are all groups R A are H.
  • All groups R 1 , R 2 , R 3 and R A are H .
  • (1-1-1), (1-1 1-1), (1-12-1) and (1-15-1) is at least a group selected from groups R 1 , R 2 , R 3 and R A selected from the above-mentioned radicals A, B and C. Particularly preferred in this case are the other groups R 1 , R 2 , R 3 and R A equal to Fl .
  • Ar 2 is furthermore preferably a fused-on benzene group which is substituted by radicals R A. Accordingly, preferred ones
  • Preferred in the formulas (1-3-1 -A), (1-4-1 -A), (1-11-1-A) and (1-12-1 -A) are all groups R 1 equal to Fl .
  • all groups R 2 are preferably Fl.
  • all groups R 3 are preferably Fl.
  • all groups R A are preferably equal to Fl.
  • All groups R 1 , R 2 , R 3 and R A are particularly preferably equal to Fl.
  • According to an alternative preferred embodiment in the formulas (1-3-1 -A), (1-4-1 -A), (1-1 1 -1 -A) and (1-12-1 -A) is at least a group selected from groups R 1 , R 2 , R 3 and R A selected from the above-mentioned radicals A, B and C. Particularly preferred in this case are the other groups R 1 , R 2 , R 3 and R A equal to Fl .
  • R 2 is preferably selected from radicals A, B and C.
  • R 1 is preferably H.
  • R 1 is preferably H and / or R A is H, particularly preferably R 1 and R A are the same H.
  • R A is preferably selected from radicals A, B and C.
  • R 1 is preferably H and / or R 2 is H, particularly preferably R 1 and R 2 are the same H.
  • R 1 is preferably selected from radicals A, B and C.
  • R 2 is preferably H and / or R A is H, particularly preferably R 2 and R A are the same H.
  • R 1 is H and / or R 2 is H, particularly preferably R 1 and R 2 are H.
  • HetAr heteroaromatic ring system
  • X reactive group, preferably CI, Br or I.
  • HetAr heteroaromatic ring system
  • Ar aromatic or heteroaromatic ring system
  • X reactive group, preferably CI, Br or I.
  • X reactive group, preferably CI, Br or I.
  • a 1,3-dicarboxylic acid benzene which bears an amino group in the 2-position or a halogen group in the 2-position
  • a 1,3-dicarboxylic acid benzene is produced which has an N-pyrrole group in the 2-position wearing.
  • the two carboxylic acid groups are converted into arylamide groups via the corresponding carboxylic acid chlorides.
  • the compound on the pyrrole group is then brominated in positions 2 and 5.
  • a Buchwald reaction is carried out in which the two nitrogen atoms of the two arylamide groups each form a ring with the pyrrole group.
  • a coupling product is first produced which has a ketone group. This is then converted into an oxime group. The oxime is converted into the two isomeric cyclic lactams in a Beckmann rearrangement. These can be separated from each other by preparative means, for example by chromatography. In a last step, the NH group of the lactam unit is further converted in a Ullmann coupling, so that an aromatic group is bound to the NH group of the lactam unit.
  • the application thus also relates to a process for the preparation of a compound comprising a structural element of the formula (I), characterized in that starting from a compound of the formula (In-1) or (In-II) wherein HetAr is a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is substituted with radicals R 2 , and Z 1 in each
  • Occurrence is the same or different CR 1 or N,
  • a halogen substituent is introduced, preferably CI, Br or I, in a second step in an Ullmann coupling reaction on the nitrogen atom of the lactam group an aromatic or
  • heteroaromatic ring system is introduced, and in a third step in the position of the halogen substituent, an amino group is introduced via a Buchwald coupling, which carries aromatic or heteroaromatic ring systems as a substituent, or an aromatic or heteroaromatic ring system is introduced via a Suzuki coupling.
  • Ring systems with 5 to 40 aromatic ring atoms which are substituted by one or more R 3 radicals characterized in that, in a first step, halogen substituents, preferably Br, are introduced in the two positions vicinal to the N atom of HetAr, and in a second step, the amide groups of the formula (Int-III) in a metal-catalyzed coupling reaction at the positions of the halogen substituents bind to HetAr so that two lactam rings are formed.
  • Hydroxylamine derivative is implemented, this hydroxylamine derivative is then reacted in a second step in a Beckmann rearrangement, and the lactam derivative obtained is then reacted in a third step on the nitrogen of the lactam unit in a Ullmann coupling.
  • the Beckmann rearrangement preferably produces two isomeric lactam derivatives, which are separated by chromatography before a further reaction takes place.
  • the compounds containing a structural element of the formula (I), in particular compounds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, can be used as monomers to produce corresponding oligomers,
  • Suitable reactive Leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic esters, amines, alkenyl or alkynyl groups with a terminal C - C double bond or CC triple bond, oxiranes, oxetanes, groups which have a cycloaddition, for example a 1,3-dipolar cycloaddition , such as dienes or azides, carboxylic acid derivatives, alcohols and silanes.
  • the invention therefore furthermore relates to oligomers, polymers or dendrimers containing one or more compounds containing a structural element of the formula (I), the bond (s) to the polymer, oligomer or dendrimer to any, in formula (I) with R 1 , R 2 or R 3 substituted positions can be localized.
  • R 1 , R 2 or R 3 substituted positions can be localized.
  • an oligomer is understood to mean a compound which is composed of at least three monomer units.
  • a polymer is understood to mean a compound which is composed of at least ten monomer units.
  • the polymers, oligomers or dendrimers according to the invention can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers according to the invention can be linear, branched or dendritic.
  • the units of the formula (I) can be linked directly to one another or they can be linked to one another via a bivalent group, for example via a substituted or unsubstituted alkylene group, via a fletero atom or via a bivalent aromatic or heteroaromatic group.
  • branched and dendritic structures for example, three or more units of the formula (I) can be linked via a trivalent or higher-valent group, for example via a trivalent or higher-valent aromatic or heteroaromatic group, to form a branched or dendritic oligomer or polymer.
  • a trivalent or higher-valent group for example via a trivalent or higher-valent aromatic or heteroaromatic group
  • the same preferences apply to the repeat units in oligomers, dendrimers and polymers as described above for compounds containing a structural element of the formula (I).
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Suitable and preferred comonomers are selected from fluorenes, spirobifluorenes, paraphenylenes, carbazoles, thiophenes, dihydrophenanthrenes, cis and trans-indofluorenes, ketones,
  • the polymers, oligomers and dendrimers usually contain further units, for example emitting (fluorescent or phosphorescent) units, such as.
  • emitting (fluorescent or phosphorescent) units such as.
  • the polymers, oligomers and dendrimers according to the invention have advantageous properties, in particular long life spans
  • the polymers and oligomers according to the invention are generally prepared by polymerizing one or more types of monomer, of which at least one monomer in the polymer leads to repeat units of the formula (I).
  • Suitable polymerization reactions are known to the person skilled in the art and are described in the literature. The following are particularly suitable and preferred polymerization reactions which lead to C-C or C-N linkages:
  • Formulations of the compounds according to the invention are required for processing the compounds containing a structural element of the formula (I) from the liquid phase, for example by spin coating or by printing processes.
  • These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methylbenzoate, mesitylene, tetralin, veratrol, THF, methyl-TFIF, 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, D-terpineol,
  • Methyl benzoate NMP, p-cymene, phenetol, 1,4-diisopropylbenzene,
  • Triethylene glycol dimethyl ether diethylene glycol monobutyl ether
  • Tripropylene glycol dimethyl ether Tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1, 1-bis (3,4-dimethylphenyl) ethane or mixtures of these solvents.
  • the invention therefore also relates to a formulation, in particular a solution, dispersion or emulsion
  • Solvent preferably an organic solvent. A person skilled in the art knows how such solutions can be prepared.
  • the formulation also contains the compound according to the application
  • the at least one further matrix material and the at least one phosphorescent emitter are each selected from those given below as preferred
  • the compounds according to the application are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs). Depending on the substitution, the compounds are used in different functions and layers.
  • OLEDs organic electroluminescent devices
  • Another object of the invention is therefore the use of the connections according to the application in electronic devices.
  • the electronic devices are preferably selected from the group consisting of organic integrated circuits (OlCs), organic field-effect transistors (OFETs), organic
  • OFTs Thin film transistors
  • OLETs organic light emitting transistors
  • OSCs organic solar cells
  • OLEDs organic electroluminescent devices
  • Another object of the invention is an electronic device containing at least one connection as defined above.
  • the electronic device is preferred
  • OLED organic electroluminescent device
  • Electron transport layers and hole blocking layers which is particularly preferably selected from emitting layers, very particularly phosphorescent emitting layers, contains at least one compound as defined above.
  • the organic electroluminescent device can also contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers,
  • Electron injection layers electron blocking layers
  • Charge generation layers and / or organic or inorganic p / n transitions are Charge generation layers and / or organic or inorganic p / n transitions.
  • the sequence of the layers of the organic electroluminescent device is preferred:
  • At least one hole-transporting layer of the device is p-doped, that is to say contains at least one p-dopant.
  • P-dopants are preferably selected from electron acceptor compounds. Particularly preferred p-dopants are selected from
  • Transition metal halides metal oxides, preferably metal oxides containing at least one transition metal or a metal of the 3rd
  • Transition metal complexes preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one
  • Oxygen atom as a binding site are also preferred.
  • Transition metal oxides as dopants preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2Ü7 , M0O3, WO3 and Re03.
  • bismuth complexes in particular Bi (III) complexes, in particular bismuth complexes with benzoic acid derivatives as complex ligands.
  • the organic electroluminescent device according to the invention can contain several emitting layers. These emission layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H. in the emitting layers there are various emissive
  • Three-layer systems that is to say systems with three emitting layers, are particularly preferred, with one of the three layers showing blue, one of the three layers green and one of the three layers showing orange or red emission.
  • an individually used emitter connection can also be suitable for generating white light
  • Wavelength range emitted Wavelength range emitted.
  • the compounds are used in an electronic device which contains one or more phosphorescent emitting compounds in an emitting layer.
  • the compounds are preferred in the
  • emitting layer in combination with the phosphorescent emitting compound, particularly preferably in a mixture with at least one further matrix material.
  • This is preferably selected from hole-conducting matrix materials, electron-conducting matrix materials and matrix materials which have both hole-conducting properties and electron-conducting properties (bipolar matrix materials), particularly preferably from electron-conducting matrix materials and bipolar matrix materials, very particularly preferably from
  • phosphorescent emitting compounds preferably includes those compounds in which the light is emitted by a spin-prohibited transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, for example a quintet state.
  • the compound containing a structural element of the formula (I) is used in an emitting layer as a matrix material in combination with one or more phosphorescent emitting compounds.
  • the phosphorescent emitting compound is preferably a red or green phosphorescent emitter.
  • the total proportion of all matrix materials in the phosphorescent emitting layer in this case is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably between 85.0 and 97.0% by volume.
  • the proportion of the phosphorescent emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferably for between 3.0 and 15.0% by volume.
  • the phosphorescent emitting layer contains only one matrix compound, preferably one
  • the emitting layer is preferably a red phosphorescent emitting layer.
  • Electroluminescent device preferably comprises two or more
  • Matrix materials (mixed matrix systems). One of them is preferably a compound containing a structural element of the formula (I).
  • the mixed matrix systems preferably comprise two or three different ones
  • Matrix materials particularly preferably two different ones
  • Matrix materials one of which is preferably a compound containing a structural element of the formula (I).
  • one of the two matrix materials has the function of a hole-transporting material, and the other of the two matrix materials has the function of an electron-transporting material.
  • the compound containing a structural element of the formula (I) is particularly preferred
  • the further compound which is present in the emitting layer mixed with the compound containing a structural element of the formula (I) is the hole-transporting material.
  • the further compound is preferably selected from carbazole compounds, biscarbazole compounds,
  • Indolocarbazole compounds and indenocarbazole compounds preferably have no electron-poor heteroaromatics
  • the compound containing a structural element of the formula (I) preferably has one or more
  • the compound containing a structural element of the formula (I) is the hole-transporting matrix material
  • the further compound which is present in the emitting layer mixed with the compound containing a structural element of the formula (I) is the electron-transporting matrix material.
  • the further connection is preferably selected
  • Carbazole compounds and indenocarbazole compounds preferably have one or more electron-deficient aromatics, preferably triazine, as substituents.
  • the compound containing a structural element of the formula (I) preferably has none
  • one of the two materials is a wide-band gap material, and there are one or two further matrix materials in the emitting layer, by means of which an electron-transporting function and / or a hole-transporting function of the mixed matrix are fulfilled .
  • this can be done in that, in addition to the wide-bandgap material, a further matrix material is present in the emitting layer, which has electron-transporting properties, and another matrix material is present in the emitting layer, which is hole-transporting
  • Such matrix materials are also referred to as bipolar matrix materials.
  • two different matrix materials are present in the emitting layer, these can be in a volume ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, particularly preferably 1:10 to 1: 1 and very particularly preferably 1: 4 to 1: 1.
  • the compound containing a structural element of the formula (I) is preferably present in the same proportion as the further matrix compound, or it is present in a higher proportion than the further matrix compound.
  • the absolute proportion of the compound containing a structural element of the formula (I) in the mixture of the emitting layer, when used as matrix material in a phosphorescent emitting layer, is preferably 10% by volume to 85% by volume, more preferably 20% by volume. % to 85% by volume, even more preferably 30% by volume to 80% by volume, most preferably 20% by volume to 60% by volume and most preferably 30% by volume to 50% by volume. -%.
  • the absolute proportion of the second matrix compound in this case is preferably 15% by volume to 90% by volume, more preferably 15% by volume to 80% by volume, even more preferably 20% by volume to 70% by volume. %, very particularly preferably 40% by volume to 80% by volume, and most preferably 50% by volume to 70% by volume.
  • a solution containing the phosphorescent emitter and the two or more matrix materials can be prepared in accordance with a preferred embodiment of the invention. This can be applied by means of spin coating, printing processes or other processes. In this case, after the solvent has evaporated, the phosphorescent emitting layer of the mixed matrix type remains.
  • the phosphorescent emitting layer of the mixed-matrix type is produced by gas phase deposition.
  • the layer can be applied.
  • each of the at least two different matrix materials can be presented in one material source, whereupon the two or more different material sources are evaporated simultaneously (“co-evaporation”).
  • the at least two matrix materials can be premixed and the mixture obtained can be placed in a single material source from which it is finally evaporated. The latter
  • the process is known as the premix process.
  • the present application therefore also relates to a mixture comprising a compound of the formulas given above and at least one further compound which is selected from
  • Matrix compounds and their chemical structure are also preferred.
  • connection is used as an electron-transporting material.
  • the compound in particular selects at least one group from electron-poor heteroaryl groups, preferably azine groups Contains triazine groups, pyrimidine groups and pyridine groups, and benzimidazole groups.
  • the compound is used as an electron transporting material, then it is preferably in a hole blocking layer, one
  • Electron transport layer or used in an electron injection layer is then n-doped, or it is in a mixture with another
  • the electron-transporting compound preferably lithium quinolinate (LiQ).
  • the compound containing a structural element of the formula (I) can also be present in the layer selected from the hole blocking layer, electron transport layer and electron injection layer, but also as a pure material.
  • an n-dopant is an organic or
  • Naphthylene carbodiimides pyridines, acridines and phenazines; Fluorenes and radical compounds.
  • Preferred fluorescent emitting compounds are selected from the class of arylamines. Under an arylamine or a
  • aromatic amine in the sense of this invention is a compound understood that contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bound directly to the nitrogen. At least one of these is preferred aromatic or hetero
  • aromatic ring systems a condensed ring system, particularly preferably with at least 14 aromatic ring atoms.
  • Preferred examples of this are aromatic anthracenamines, aromatic
  • Anthracene diamines aromatic pyrenamines, aromatic pyrendiamines, aromatic chrysenamines or aromatic chrysediamines.
  • An aromatic anthracenamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • An aromatic anthracene diamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10 position.
  • Aromatic pyrenamines, pyrendiamines, chrysenamines and chrysenamines are defined analogously, the diarylamino groups being preferably attached to the pyrene in the 1-position or in the 1,6-position.
  • Further preferred emitting compounds are indenofluorenamines or -diamines, benzoindenofluorenamines or -diamines, and dibenzoindenofluoramines or -diamines, and also indenofluorene derivatives with condensed aryl groups. Pyrene-arylamines are also preferred.
  • benzoindenofluorene amines benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives which are linked to furan units or to thiophene units.
  • Preferred matrix materials for fluorescent emitters are selected from the classes of the oligoarylenes (e.g. 2,2 ', 7,7'-tetraphenylspirobifluorene), in particular the oligoarylenes containing condensed aromatic groups, the oligoarylenevinylenes, the polypodal metal complexes, the hole-conducting compounds, the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; the atropisomers, the boronic acid derivatives or the
  • Benzanthracenes Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, oligoarylenvinylenes, ketones, phosphine oxides and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene,
  • an oligoarylene is to be understood as a compound in which at least three aryl or arylene groups are bonded to one another.
  • Particularly suitable phosphorescent emitting compounds are compounds which, when suitably excited, emit light, preferably in the visible range, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 .
  • Compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used as phosphorescent emitting compounds, in particular compounds which contain iridium, platinum or copper.
  • all luminescent iridium, platinum or copper complexes are considered
  • preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, e.g. B.
  • CBP N, N-biscarbazolylbiphenyl or carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, aza-carbazole derivatives, bipolar matrix materials, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, carbohydrate derivatives, dibenzazole derivatives, carboxylate derivatives, dibenzazolazole derivatives, dibenzazole derivatives, dicarboxyl derivatives, Derivatives,
  • Triphenylene derivatives or lactams.
  • a phosphorescent emitter in combination with a phosphorescent emitter and a further matrix material, which is preferably selected from the above-mentioned preferred matrix materials and is particularly preferably selected from carbazole compounds,
  • Suitable charge transport materials such as those in the hole injection or hole transport layer or electron blocking layer or in the
  • Electron transport layer of the electronic according to the invention is Electron transport layer of the electronic according to the invention
  • Device can be used, for example, are those in Y.
  • Aluminum complexes for example Alq3, zirconium complexes, for example Zrq 4 , lithium complexes, for example 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.
  • Electron transporting layers are shown in the following table:
  • Preferred materials for hole-transporting layers of OLEDs are indenofluorenamine derivatives, amine derivatives,
  • Hexaazatriphenylene derivatives amine derivatives with condensed aromatics, monobenzoindenofluorenamines, dibenzoindenofluorenamines,
  • Dihydroacridine derivatives spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene-diarylamines, and 9,10-dihydroanthracene-spiro-amine compounds are used.
  • the following compounds HT-1 to HT-72 are suitable for use in a layer with a hole-transporting function, in particular in a hole-injection layer, a hole-transport layer and / or an electron blocking layer, or for use in an emitting layer as a matrix material, in particular as a matrix material in one emitting layer containing one or more
  • the compounds HT-1 to HT-72 are generally well suited for the above-mentioned uses in OLEDs of all types and
  • the connections show good performance data in OLEDs, in particular good service life and good efficiency.
  • Processes for the preparation of the compounds HT-1 to HT-72 are known in the prior art.
  • processes for the preparation of the compounds HT-16, HT-17 and HT-72 are disclosed in WO2014 / 079527, there on pages 32-33 and in the exemplary embodiments.
  • Manufacturing process of the compound HT-18 are disclosed in WO 2013/120577 and W02017 / 144150 in the description and the exemplary embodiments.
  • Methods for producing the compounds HT-20 to HT-32 are disclosed in WO2012 / 034627, there on p. 39-40 and in the exemplary embodiments.
  • Metals with a low work function, metal alloys or multilayer structures are made as the cathode of the electronic device
  • alkaline earth metals such as, for example, alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example an alloy of, are also suitable
  • Magnesium and silver In the case of multilayer structures, other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as, for example, B. Ag or Al, in which case combinations of the metals, such as Ca / Ag, Mg / Ag or Ba / Ag are usually used. It can also be preferred to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. For example, alkali metal or
  • Alkaline earth metal fluorides but also the corresponding oxides or
  • LiF, L12O, BaF2, MgO, NaF, CsF, CS2CO3, etc. Lithium quinolinate (LiQ) can also be used.
  • the layer thickness of this layer is preferably between 0.5 and 5 nm.
  • the anode preferably has a work function greater than 4.5 eV vs. Vacuum on. Metals with a high redox potential are suitable for this, such as Ag, Pt or Au. On the other hand, metal / metal oxide electrodes (eg Al / Ni / NiO x , Al / PtO x ) can also be preferred. For some applications, at least one of the electrodes must be transparent or
  • anode materials are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • ITO Indium tin oxide
  • IZO indium zinc oxide
  • conductive, doped organic materials in particular conductive doped polymers.
  • the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • the device is structured (depending on the application), contacted and finally sealed in order to exclude damaging effects of water and air.
  • the electronic device is characterized in that one or more layers are coated using a sublimation process.
  • the materials are evaporated 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 electronic device is also preferred.
  • Carrier gas sublimation are coated.
  • the materials are applied at a pressure between 10 5 mbar and 1 bar.
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and structured in this way (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
  • An electronic device is also preferred.
  • one or more layers of solution such as. B. by spin coating, or by any printing method, such as. B. screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing). Soluble connections are necessary for this. High solubility can be achieved by suitable substitution of the compounds.
  • one or more layers of solution and one or more layers are applied by a sublimation process to produce an electronic device according to the invention.
  • Electronic devices containing one or more connections as defined above are preferred in displays as light sources in
  • Illumination applications and as light sources in medical and / or cosmetic applications e.g. light therapy.
  • Example b 7-bromo-6- (3,5-diphenylphenyl) indolo [1,2-a] quinazolin-5-one
  • Example c 6- (3,5-diphenylphenyl) -7-phenyl-indolo [1, 2-a] quinazolin-5-one 13.3 g (110.0 mmol) phenylboronic acid, 59 g (110.0 mmol) 7-bromo-6- (3,5-diphenylphenyl) indolo [1, 2-a] quinazolin-5-one and 44.6 g (210.0 mmol) tripotassium phosphate are dissolved in 500 ml of toluene, 500 ml of dioxane and 500 ml of water are suspended.
  • the mixture is carefully concentrated on a rotary evaporator, the precipitated solid is filtered off with suction and washed with water and ethanol.
  • the crude product is purified twice using a fleece extractor (toluene / fleptan 1: 1) and the solid obtained is recrystallized from toluene. After sublimation, 8.2 g (12 mmol, 48%) of the desired target compound are obtained.
  • Glass plates that are coated with structured ITO (indium tin oxide) with a thickness of 50 nm are first treated with an oxygen plasma, followed by an argon plasma, before the coating. These glass plates, which have been treated with plasma, form the substrates to which the OLEDs are applied.
  • structured ITO indium tin oxide
  • the OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electrons
  • EBL emission layer
  • EML hole blocking layer
  • HBL electron transport layer
  • EIL electron injection layer
  • cathode is formed by a 100 nm thick aluminum layer.
  • the exact structure of the OLEDs can be found in Tables 1a to 1c.
  • the data of the OLEDs are listed in Tables 2a to 2c.
  • the materials required to manufacture the OLEDs are shown in Table 3.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material or the matrix materials by cover vaporization in a certain volume fraction.
  • An indication like A: B: C (45%: 45%: 10%) means that material A in a volume fraction of 45%, material B in a volume fraction of 45% and material C in a volume fraction of 10 % is present in the shift.
  • the electron transport layer or one of the other layers can also consist of a mixture of two materials.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra and the external quantum efficiency are determined as a function of the luminance, calculated from current-voltage-luminance characteristics, assuming a Lambertian radiation characteristic.
  • the electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and the CIE 1931 x and y color coordinates are calculated therefrom.
  • EQE1000 describes the external quantum efficiency that is achieved at 1000cd / m 2 .
  • Examples E1 to E6 the materials according to the invention are used as matrix material in the emission layer of green phosphorescent OLEDs.
  • E10 and E11 are used in Examples E10 and E11 as ETL and HBL of blue fluorescent OLEDs. Use as ETL and HBL in phosphorescent OLEDs is also possible.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne des composés N-hétéroaromatiques condensés, des procédés de production de ces composés et des dispositifs électroniques contenant ces composés.
EP19809485.6A 2018-11-30 2019-11-29 Composés pour dispositifs électroniques Pending EP3888147A1 (fr)

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WO2023052363A1 (fr) * 2021-09-29 2023-04-06 Boehringer Ingelheim International Gmbh Nouvelles tétrahydroquinoléines et chimères ciblant la protéolyse (protac) les comprenant utilisées en tant qu'agents de dégradation de smarca
WO2023197744A1 (fr) * 2022-04-15 2023-10-19 陕西莱特光电材料股份有限公司 Composé azoté, dispositif électroluminescent organique et appareil électronique
CN115536662A (zh) * 2022-06-29 2022-12-30 广州大学 一种含脒基结构的四环吲哚类化合物、合成方法及其应用

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DD297963A5 (de) * 1988-11-23 1992-01-30 Bayer Aktiengesellschaft,De N-aryl-stickstoffheterocyclen, verfahren sowie neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren
GB0017508D0 (en) * 2000-07-17 2000-08-30 Novartis Ag Antimicrobials
DE102010045405A1 (de) 2010-09-15 2012-03-15 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
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KR102015765B1 (ko) 2012-02-14 2019-10-21 메르크 파텐트 게엠베하 유기 전계발광 소자용 스피로비플루오렌 화합물
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KR20160040826A (ko) * 2014-10-06 2016-04-15 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
JP2017537466A (ja) * 2014-10-24 2017-12-14 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ 有機エレクトロルミネッセンス素子
US9856208B2 (en) * 2015-09-03 2018-01-02 The Royal Institution For The Advancement Of Learning/Mcgill University Method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond
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