EP3044285A1 - Heterocyclische verbindungen - Google Patents

Heterocyclische verbindungen

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Publication number
EP3044285A1
EP3044285A1 EP14752276.7A EP14752276A EP3044285A1 EP 3044285 A1 EP3044285 A1 EP 3044285A1 EP 14752276 A EP14752276 A EP 14752276A EP 3044285 A1 EP3044285 A1 EP 3044285A1
Authority
EP
European Patent Office
Prior art keywords
formula
radicals
group
ring
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP14752276.7A
Other languages
German (de)
English (en)
French (fr)
Inventor
Philipp Stoessel
Nils KOENEN
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
Priority to EP14752276.7A priority Critical patent/EP3044285A1/de
Publication of EP3044285A1 publication Critical patent/EP3044285A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • 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
    • C07D471/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
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    • 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
    • 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
    • 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
    • C07D491/08—Bridged 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/14—Perylene derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
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    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/002—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being condensed in peri position and in 1-2 or 2-3 position
    • C09B5/008—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being condensed in peri position and in 1-2 or 2-3 position only N-containing hetero rings
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/022—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20
    • C09B5/028—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20 only N-containing hetero rings
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    • C09B57/001—Pyrene dyes
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • 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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    • H10K85/649—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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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Definitions

  • the present invention relates to heterocyclic compounds which are suitable for use in electronic devices. Furthermore, the present invention relates to processes for their preparation and electronic devices.
  • Organic-based charge transport materials e.g., triarylamine-based hole transporters
  • OLEDs or PLEDs organic or polymeric light emitting diodes
  • display and display devices or organic photoreceptors in copiers.
  • 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
  • the above arrangement represents the general structure of an organic electronic device, wherein different layers can be combined, so that in the simplest case an arrangement of two electrodes results, between which an organic layer is located.
  • the organic layer in this case fulfills all functions, including the emission of light in the case of OLEDs.
  • Such a system is described, for example, in WO 90/13148 A1 on the basis of poly (p-phenylenes).
  • These properties include in particular the energy efficiency with which an electronic device solves the given task.
  • the luminous efficacy should be high, so that as little electrical power as possible has to be applied in order to achieve a specific light flux.
  • the lowest possible voltage should be necessary to achieve a given luminance.
  • Another problem is in particular the lifetime of the electronic devices.
  • the object is to provide novel compounds which result in electronic devices with improved properties.
  • the object is to provide hole blocking materials, electron injection materials, electron transport materials, electron transporting matrix materials for mixed matrix systems and / or singlet matrix materials which show improved properties in terms of efficiency, operating voltage and / or lifetime.
  • the connections should be as easy as possible, in particular to show good solubility and film formation.
  • the electronic devices should be used or adapted for many purposes.
  • R 1 is the same or different H, D, F, Cl, Br, I at each occurrence
  • Ring atoms which may be substituted by one or more radicals R 2 , or a Diarylaminooeuvre, Diheteroarylaminooeuvre or Arylheteroarylaminooeuvre having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2 ; two or more adjacent radicals R 1 with each other or R 1 with R may be a mono- or polycyclic, aliphatic,
  • R 2 is the same or different at each occurrence, H, D, F or a
  • aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by F; two or more substituents R 2 may also together form a mono- or polycyclic aliphatic ring system; which is characterized in that the respective residues R of the two groups Y together with the carbon atoms of the heteroaromatic ring form a ring according to the following formulas;
  • Alkylene group having 1, 2 or 3 C atoms, which with one or
  • ortho-linked arylene or heteroarylene group having 5 to 14
  • aromatic ring atoms which may be substituted by one or more radicals R 2 ; and wherein the carbon-carbon double bond shown in the formula (5) to (11) of an aromatic double bond of the
  • R 3 is identical or different on each occurrence, F, a straight-chain
  • R 3 may be, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 , or an aryloxy or heteroaryl oxyoeuvre having 5 to 24 aromatic ring atoms, by one or more radicals R 2 may be substituted or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 ;
  • two radicals R 3 which are bonded to the same carbon atom, together form an aliphatic or aromatic ring system and thus form a spiro system;
  • G in the compound of the formula (1) is selected from O, an alkylene group having 1, 2 or 3 C atoms, which may be substituted by one or more radicals R 2 , is particularly preferred.
  • -CR 2 CR 2 - or an ortho-linked arylene or heteroarylene group of 5 to 14
  • G in the compound of the formula (1) is selected from an alkylene group having 1, 2 or 3 C atoms which may be substituted by one or more radicals R 2 , -CR 2 CRCR 2 - or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms, which may be substituted by one or more radicals R 2 .
  • G is an alkylene group, this may be a 1, 1, 1, 2, or 1, 3-alkylene group.
  • this is the presence of an additional ring based on the
  • Groups Y is essential to the invention, preferably a fused ring system, which is particularly preferably aliphatic. As is apparent from the above-mentioned formula (1), the radical Y contains no acidic benzylic protons. What is meant by acidic benzylic protons in the context of the present invention is defined below.
  • Carbon atoms formally lies between the degree of bonding of a single bond and that of a double bond.
  • the characterization of the formal double bond is not intended to be limiting to the structure, but it will be apparent to those skilled in the art that it is meant herein an aromatic bond.
  • the absence of acidic benzylic protons is achieved in formulas (5) to (7) by defining A 1 and A 3 when they are C (R 3 ) 2 , such that R 3 is other than hydrogen.
  • the absence of acidic benzylic protons is achieved in formulas (8) to (11) by being a bicyclic structure. Due to the rigid spatial arrangement, R 1 , if it is H, is significantly less acidic than benzylic protons, since the corresponding anion of the Bicyclic structure is not mesomeriestabilinstrument. Even though R 1 in
  • Formulas (8) to (11) is H, it is therefore a non-acidic proton in the context of the present application.
  • adjacent carbon atoms means that the carbon atoms are directly bonded to each other
  • adjacent radicals in the definition of radicals means that these radicals are attached to the same carbon atom or to adjacent carbon atoms.
  • An aryl group for the purposes of this invention contains 6 to 40 carbon atoms; a heteroaryl group in the context of this invention contains 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of
  • heteroatoms are preferably selected from N, O and / or S.
  • aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or
  • Heteroaryl group for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains 1 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and
  • Heteroatoms at least 5 results.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
  • a C, N or O atom or a carbonyl group may be interrupted.
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.
  • aromatic ring systems in the context of this invention and also systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group.
  • systems in which two or more aryl or heteroaryl groups are bonded directly to each other such as.
  • aromatic or heteroaromatic ring system are understood.
  • a cyclic alkyl, alkoxy or thioalkoxy group is understood as meaning a monocyclic, a bicyclic or a polycyclic group.
  • a C 1 - to C 4 -alkyl group in which individual H atoms or CH 2 groups may be substituted by the abovementioned groups, for example the radicals methyl, ethyl, n-propyl, i Propyl, cyclopropyl, n -butyl, i -butyl, s -butyl, t -butyl, cyclobutyl, 2-methylbutyl, n -pentyl, s -pentyl, t -pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n -Hexyl, s-hexyl, t -hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl,
  • alkenyl group is understood as meaning, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
  • alkynyl group is meant, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
  • Suitable C8 to C40 alkoxy groups include methoxy, trifluoromethoxy, ethoxy, n- Propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methyl-butoxy understood.
  • aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms, which may be substituted in each case with the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic, are understood, for example, groups which are derived from benzene, naphthalene , Anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans- indenofluorene, cis or trans monobenzoindenofluorene, cis or trans dibenz
  • the heteroaromatic ring system with the radical X 1 represents a system having 10 to 30 aromatic ring atoms, preferably 0 to 24 and particularly preferably 10 to 18.
  • compounds according to formula (1) are preferred in which the ring structures according to one of the formulas (5), (6), (7), (8), (9), (10) and / or (11) at most two, preferably at most one of the groups A 1 , A 2 and A 3 is O, S or NR 3 , especially preferably none of the groups A, A 2 and A 3 is O, S or NR 3 . Furthermore, compounds according to formula (1) are preferred in which
  • At least one of the groups A 1 and A 3 is the same or different for O or NR 3 and A 2 is C (R 1 ) 2 .
  • compounds are preferred, which are characterized in that in the ring structures according to one of the formulas (5), (6), (7), (8), (9), (10) and / or (11) the groups A 1 and A 3 are the same or different at each occurrence for C (R 3 ) 2 and A 2 is C (R 1 ) 2 , preferably C (R 3 ) 2 or CH 2 and particularly preferably CH 2 .
  • Bridged head stand for H, D, F or CH 3 .
  • the two groups Y have a ring structure according to one of the following formulas (5-A), (5-B), (5-C), (5-D), ( 5-E) and / or (5-F)
  • Examples of particularly preferred groups of the formula (5-A) to (5-F) are the following groups of the formulas (5-1) to (5-69)
  • Groups Y have a ring structure according to any of the following formulas (6-A) to (6-F)
  • Examples of particularly preferred groups of the formula (6-A) to (6-F) are the groups of the formulas (6-1) to (6-14) listed below.
  • Formula (7-D) form formula (7-E), wherein R 1 and R 3 have the abovementioned meanings, A 1 , A 2 and A 3 are the same or different at each occurrence for O or NR 3 and the dashed lines represent the bonds of the two radicals Y to the ring comprising the radical X 1 according to formula (1).
  • the two groups Y in the structure according to formula (1) can have a ring structure according to one of the following formulas (8-A) to (8-C)
  • Formula (8-A) Formula (8-B) form formula (8-C), wherein the symbols used have the meanings given above and the dashed lines the bonds of the two radicals Y to the ring comprising the radical X 1 according to formula ( 1).
  • formulas (8-A) to (8-C) preference is given to those compounds which have structures according to formulas (8-B) and (8-C), where compounds having structures of the formula (8-C ) are particularly preferred.
  • Examples of particularly preferred groups of the formula (8-A) and (8-C) are the groups of the formulas (8-1) to (8-3) listed below.
  • Formula (9-A) Formula (10-A) form formula (11-A), wherein the symbols used have the meanings given above and the dashed lines the bonds of the two radicals Y to the ring comprising the radical X 1 according to formula ( 1).
  • Examples of particularly preferred groups of formula (9-A), (10-A) and (11-A) are the following groups of formulas (9-1) to (9-27).
  • the group G in stands for a 1,2-ethylene group which may be substituted by one or more radicals R 2 , where R 2 is preferably the same or different at each occurrence for H or an alkyl group having 1 to 4 C atoms, or an ortho-arylene group having 6 to 10 C atoms in the ring, which may be substituted by one or more radicals R 2 , but is preferably unsubstituted, in particular an ortho-phenylene group, which may be substituted by one or more radicals R 2 , but is preferably unsubstituted.
  • two radicals R 3 which are bonded to the same carbon atom, together form an aliphatic or aromatic ring system and thus form a spiro system;
  • R 3 can form an aliphatic ring system with an adjacent radical R or R 1 .
  • the radical R 3 may preferably be identical or different at each occurrence for F, a straight-chain alkyl group having 1 to 3 C atoms, in particular methyl, or an aromatic or heteroaromatic ring system with 5 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 , but is preferably unsubstituted, are;
  • two radicals R 3 which are bonded to the same carbon atom, together form an aliphatic or aromatic ring system and thus form a spiro system; furthermore, R 3 can with a
  • adjacent radical R or R 1 form an aliphatic ring system.
  • a maximum of three symbols X in the formula (1) set out above and in the preferred embodiments of this formula for N particularly preferably a maximum of two symbols X in formula (1) represent N, very particularly preferably at most one symbol X in formula ( 1) for N.
  • all symbols X are particularly preferably CR in structures of the formula (1).
  • the compounds have at least two ring structures according to the formulas (5) to (11).
  • CyG (CyH) n where CyG and CyH together each span a ring and where symbols and indices are: n is 2 or 3 or 4, where n is 2 or 3;
  • CyG is a structural element selected from the formulas
  • CyH is at least one structural element according to the following formula
  • a maximum of three symbols X and X "in CyG and / or CyH stands for N, more preferably at most two symbols X and X" in CyG and / or CyH for N, most preferably at most one symbol of X and X "in CyG and / or CyH for N.
  • all symbols X stand for CR and all X "for CR 1 in structures of the formula
  • CyG (CyH) n CyG (CyH) n . It will be understood that the present invention also includes regioisomers resulting from the manner in which the ring CyH is fused.
  • heterocyclic compounds according to the invention comprising structures of the formula (1), may also be chiral, depending on the structure. This is especially the case if they contain substituents,
  • alkyl, alkoxy or aralkyl groups which have one or more stereocenters. Since it is in the basic structure of
  • Heterocyclic compound can also act on a chiral structure, the formation of diastereomers and several pairs of enantiomers is possible.
  • the compounds of the invention then comprise both the mixtures of the different diastereomers or the corresponding racemates as well as the individual isolated diastereomers or
  • the compound may be in the form of an enantiomeric mixture, more preferably a diastereomeric mixture.
  • the properties of electronic devices that are obtainable using the compounds according to the invention can be increased unexpectedly.
  • the compound according to formula (1) has no N-oxide, ester or amide groups.
  • the above-mentioned preferred embodiments can be combined with one another as desired. In a particularly preferred embodiment of the invention, the abovementioned preferred embodiments apply simultaneously.
  • the compounds according to the invention can in principle be prepared by various methods. However, the methods described below have been found to be particularly suitable.
  • another object of the present invention is a process for the preparation of the compounds comprising structures according to formula (1), in which at least one primary arylamine with at least one ß-keto-vinyl alcohol (or the tautomeric ß-keto-aldehyde) a ⁇ -keto-enamine compound is reacted, which is then cyclized.
  • the compounds of the invention comprising structures of formula (1) in high purity, preferably more than 99% (determined by 1 H-NMR and / or HPLC).
  • the compounds according to the invention can also have suitable substituents, for example by longer alkyl groups (about 4 to 20 C atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups, which have a Solubility in common organic solvents cause, such as toluene or xylene at Room temperature soluble in sufficient concentration to process the complexes from solution can.
  • These soluble compounds are particularly suitable for processing from solution, for example by printing processes. It should also be noted that the compounds according to the invention comprising at least one structure of the formula (1) already have an increased solubility in these solvents.
  • the compounds of the invention may also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is particularly possible with compounds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably carried out via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is still possible, the
  • the compounds of the invention and polymers can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore furthermore provides oligomers, polymers or dendrimers containing one or more of the abovementioned structures of the formula (1) or compounds according to the invention, where one or more bonds of the compounds according to the invention or of the structures of the formula (1) to the polymer, oligomer or dendrimer available. Depending on the linkage of the structures of the formula (1) or the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain.
  • the polymers, oligomers or dendrimers may be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers may be linear, branched or dendritic.
  • the repeat units of the compounds according to the invention in oligomers, dendrimers and polymers have the same preferences as described above.
  • the monomers according to the invention are homopolymerized or copolymerized with further monomers. Preference is given to copolymers in which the units of the formula (1) or the preferred embodiments described above are present at 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%.
  • Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (eg according to EP 842208 or WO 2000/022026), spirobifluorenes (eg according to US Pat
  • the polymers, oligomers and dendrimers may also contain other units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.
  • the present compounds can be a relatively low
  • Another object of the present invention is accordingly a compound having a molecular weight of preferably at most 10,000 g / mol, more preferably at most 5000 g / mol and especially preferably at most 3000 g / mol. Furthermore, preferred compounds are characterized in that they are sublimable. These compounds generally have one
  • Yet another object of the present invention is a formulation comprising a compound of the invention or an oligomer according to the invention, polymer or dendrimer and at least one further compound.
  • the further compound may preferably be a solvent.
  • the further compound can also be a further organic or inorganic compound which is likewise used in the electronic device, for example a matrix material.
  • This further compound may also be polymeric.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) Fenchone, 1, 2,3,5-tetrannethylbenzene, 1, 2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3 , 4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin,
  • Yet another object of the present invention is a composition containing a compound of the invention and at least one further organically functional material functional
  • Materials are generally the organic or inorganic materials incorporated between anode and cathode.
  • the organically functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials,
  • Electron blocking materials and hole blocking materials therefore also relates to a composition comprising at least one compound comprising structures according to formula (1) and at least one further matrix material. According to a particular aspect of the present invention, the other
  • a further subject of the present invention is a composition comprising at least one compound comprising at least one structure according to formula (1) and at least one wide band gap material, wherein a wide band gap material is a material in the sense of
  • the additional compound may have a band gap of 2.5 eV or more, preferably 3.0 eV or more, most preferably from
  • the band gap can be calculated among other things by the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • these values are to be regarded as HOMO or LUMO energy levels of the materials.
  • the lowest triplet state Ti is defined as the energy of the triplet state with the lowest energy, which results from the described quantum chemical calculation.
  • the lowest excited singlet state Si is defined as the energy of the excited singlet state with the lowest energy which results from the described quantum chemical calculation.
  • the method described here is independent of the software package used and always gives the same results. Examples of frequently used programs for this purpose are "Gaussian09W” (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.)
  • the present invention also relates to a composition comprising at least one compound comprising structures according to formula (1) and at least a phosphorescent emitter, wherein the term phosphorescent emitter and phosphorescent dopants are understood.
  • phosphorescent dopants are typically
  • phosphorescent dopants compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used, in particular compounds containing iridium, platinum or copper.
  • luminescent iridium, platinum or copper complexes are regarded as phosphorescent compounds.
  • Examples of phosphorescent dopants are listed in a following section.
  • a dopant is understood to mean the component whose proportion in the mixture is the smaller. Accordingly, under a matrix material in a system comprising a matrix material and a dopant understood that component whose proportion in the mixture is the larger.
  • Preferred phosphorescent dopants for use in mixed-matrix systems are those specified below
  • phosphorescent dopants can be found in the applications WO 2000/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244,
  • WO 2005/019373 and US 2005/0258742 are taken.
  • all the phosphorescent complexes used in the state of the art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescent devices are suitable for use in the devices according to the invention.
  • the above-described compound comprising structures of the formula (1) or the above-mentioned preferred embodiments may preferably be used as an active component in an electronic device.
  • an electronic device is a
  • Device comprising anode, cathode and at least one layer, said layer at least one organic or
  • the electronic device according to the invention thus contains anode, cathode and at least one layer which contains at least one compound comprising structures of the formula (1).
  • Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs),
  • O-FETs organic field-effect transistors
  • O-TFTs organic thin-film transistors
  • O-LETs organic solar cells
  • O-SCs organic solar cells
  • Detectors organic photoreceptors, organic field quench devices (O-FQDs), organic electrical sensors, light-emitting electrochemical cells (LECs) or organic laser diodes (O-lasers), containing in at least one layer at least one compound comprising structures of formula (1).
  • O-FQDs organic field quench devices
  • LOCs light-emitting electrochemical cells
  • O-lasers organic laser diodes
  • Active components are generally the organic or inorganic materials incorporated between the anode and cathode, for example, charge injection, charge transport or charge blocking materials, but especially emission materials and matrix materials.
  • a preferred embodiment of the invention are organic electroluminescent devices.
  • the organic electroluminescent device includes cathode, anode and at least one emitting layer.
  • they may 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, charge generation layers and / or organic or inorganic p / n junctions.
  • one or more hole transport layers are p-doped, for example, with metal oxides such as M0O 3 or WO 3 or with (per) fluorinated low-electron aromatics, and / or that one or more electron-transport layers are n-doped.
  • interlayers may be introduced between two emitting layers which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. It should be noted, however, that not necessarily each of these layers must be present.
  • the organic electroluminescent device can be any organic electroluminescent device.
  • the organic electroluminescent device can be any organic electroluminescent device.
  • three-layer systems the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, WO 2005/011013) or systems having more than three have emitting layers. It may also be a hybrid system wherein one or more layers fluoresce and one or more other layers phosphoresce.
  • the organic electroluminescent device contains the compound according to the invention
  • matrix material preferably as electron-conducting matrix material in one or more emitting layers, preferably in combination with another matrix material, preferably a hole-conducting matrix material.
  • Layer comprises at least one emitting compound.
  • the triplet level of the matrix material is higher than the triplet level of the
  • Suitable matrix materials for the compounds according to the invention are ketones, phosphine oxides, sulfoxides and sulfones, for. B. according to
  • WO 2010/006680 triarylamines, carbazole derivatives, z. B. CBP (N, N-bis-carbazolylbiphenyl), m-CBP or in WO 2005/039246,
  • bipolar matrix materials e.g. B. according to WO 2007/137725, silanes, z. B. according to WO 2005/11 1172, azaborole or boronic esters, z. B. according to WO 2006/117052, Diazasilolderivate, z. B. according to
  • WO 2010/054729 Diazaphospholderivate, z. B. according to WO 2010/054730, triazine derivatives, z. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, for. B. according to EP 652273 or
  • a plurality of different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Also preferred is the use of a mixture of one
  • charge-transporting matrix material and an electrically inert matrix material which does not or not to a significant extent on
  • Charge transport is involved, such. As described in WO 2010/108579.
  • triplet emitter with the shorter-wave emission spectrum serves as a co-matrix for the triplet emitter with the longer-wave emission spectrum.
  • a compound according to the invention comprising structures according to formula (1) can be used as matrix material in an emission layer of an organic electronic device, in particular in an organic electroluminescent device, for example in an OLED or OLEC.
  • the matrix material containing compound comprising structures according to formula (1) is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.
  • the proportion of the matrix material in the emitting layer in this case is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferred for fluorescent emitting layers between 92.0 and 99.5% by volume and for phosphorescent emitting layers between 85.0 and 97.0 vol.%.
  • the proportion of the dopant is between 0.1 and
  • An emitting layer of an organic electroluminescent device may also contain systems comprising a plurality of matrix materials (mixed-matrix systems) and / or multiple dopants. Also in this case, the dopants are generally those materials whose proportion in the
  • the proportion of a single matrix material in the system may be smaller than the proportion of a single dopant.
  • the compound comprising structures according to formula (1) are used as a component of mixed-matrix systems.
  • the mixed-matrix systems preferably comprise two or three different matrix materials, more preferably two different matrix materials.
  • One of the two materials preferably constitutes a material with hole-transporting properties and the other material a material with electron-transporting properties
  • electron-transporting and hole-transporting properties of the mixed-matrix components may also be mainly or completely combined in a single mixed-matrix component, with the further or the further mixed-matrix components being different
  • the two different matrix materials may 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. Preference is given to mixed-matrix systems in
  • an electronic device preferably an organic electroluminescent device, is the subject of the present invention, which comprises one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more embodiments comprises a plurality of electron-conducting layers, as an electron conductive compound.
  • low work function metals, metal alloys or multilayer structures of various metals are preferable, such as alkaline earth metals, alkali metals, main group metals or lanthanides (eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
  • alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver.
  • further metals which have a relatively high work function such as, for example, B. Ag, which then usually combinations of metals, such as Mg / Ag, Ca / Ag or Ba / Ag are used. It may also be preferred to introduce between a metallic cathode and the organic semiconductor a thin intermediate layer of a material with a high dielectric constant. For this example comes
  • Alkali metal or alkaline earth metal fluorides but also the corresponding oxides or carbonates in question (eg LiF, L12O, BaF 2 , MgO, NaF, CsF,
  • CS2CO3, etc. Likewise suitable for this purpose are organic alkali metal complexes, for. B. Liq (lithium quinolinate).
  • the layer thickness of this layer is preferably between 0.5 and 5 nm.
  • the anode high workfunction materials are preferred.
  • the anode has a work function greater than 4.5 eV. Vacuum up.
  • metals with a high redox potential are suitable for this purpose, such as, for example, Ag, Pt or Au.
  • metal / metal oxide electrodes eg Al / Ni / ⁇ , Al / PtO x
  • at least one of the electrodes must be transparent or partially transparent to allow either the irradiation of the organic material (O-SC) or the outcoupling of light (OLED / PLED, O-LASER).
  • Preferred anode materials here are conductive mixed metal oxides.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • conductive, doped organic materials in particular conductive doped polymers, for. B. PEDOT, PANI or derivatives of these polymers.
  • a p-doped hole transport material is applied to the anode as a hole injection layer is said to be suitable as p-dopant metal oxides, for example m0o 3 or WO3, or (per) fluorinated electron-deficient aromatics.
  • p-dopants are HAT-CN (hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection in materials with a deep HOMO, ie one
  • the device is structured accordingly (depending on the application), contacted and finally hermetically sealed because the life of such devices drastically shortened in the presence of water and / or air.
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with a sublimation method.
  • the materials are applied in vacuum sublimation at an initial pressure of usually less than 10 "5 mbar, preferably less than 10 ⁇ vapor-deposited 6 mbar. It is also possible that the initial pressure is even lower or even higher, for example less than 10" 7 mbar.
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 "5 mbar and 1 bar, a special case of this
  • OVJP Organic Vapor Jet Printing
  • an electronic device in particular an organic electroluminescent device, which is characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing process, such.
  • screen printing flexographic printing, offset printing or Nozzle printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing) can be produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink jet printing
  • soluble compounds are necessary, which are obtained for example by suitable substitution.
  • the electronic device in particular the organic electroluminescent device, can also be manufactured as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
  • the organic electroluminescent device can also be manufactured as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
  • efindungsdorfe connection comprising structures according to formula (1) and a matrix material from solution to apply and then a
  • the electronic devices according to the invention are distinguished by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers having structures of the formula (1), especially as electron-conducting materials, have a very good life.
  • Electroluminescent devices comprising compounds, oligomers, polymers or dendrimers having structures according to formula (1) as electron-conducting materials have an excellent efficiency. In particular, the efficiency is significantly higher than analogous compounds containing no structural unit according to formula (1).
  • the compounds according to the invention, oligomers, polymers or dendrimers having structures of the formula (1) show a very high stability and lead to compounds having a very high molecular weight
  • Structures according to formula (1) can be avoided in electronic devices, in particular organic electroluminescent devices, the formation of optical loss channels. As a result, these devices are distinguished by a high PL and thus high EL efficiency of emitters or an excellent energy transfer of the matrices to dopants.
  • Dendrimers having structures according to formula (1) in layers having structures according to formula (1) in layers
  • Electroluminescent devices leads to a high mobility of the electron-conductor structures.
  • Compounds, oligomers, polymers or dendrimers having structures of the formula (1) are distinguished by excellent thermal stability, with compounds having a molecular weight of less than about 1200 g / mol being readily sublimable
  • Compounds, oligomers, polymers or dendrimers having structures according to formula (1) have excellent glass film formation. 8. Compounds, oligomers, polymers or dendrimers having structures according to formula (1) form very good films from solutions.
  • Another object of the present invention is the use of a compound of the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as Lochblockiermaterial, electron injection material, and / or
  • Electron transport material is Electron transport material.
  • the following syntheses are carried out under an inert gas atmosphere in dried solvents.
  • the metal complexes are additionally handled in the absence of light or under yellow light.
  • the solvents and reagents may, for. 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.
  • a mixture of 16.8 g (100 mmol) of 5- [1-hydroxy-meth- (E) -ylidene] -2,2,4,4-tetramethylcyclopentanone, S1 and 14.3 g (100 mmol) of 1-amino-naphthalene, 134-32-7] is slowly heated to 160 ° C. at the water separator, the water formed in the reaction being slowly distilled off from the melt. After 10 h at 160 ° C is slowly added dropwise 100 ml of toluene and distilled this over the water from to remove the remaining water from the melt and the apparatus.
  • the deep brown melt thus obtained is mixed in an argon countercurrent with about 300 g of polyphosphoric acid (Merck KGaA) and then stirred at 160 ° C for a further 16 h. After cooling to 120 ° C is added to the black viscous melt dropwise with 400 ml of water (attention: Exotherm! And stirred until the melt has completely homogenized, with a brown solid precipitates. The suspension is transferred to a beaker with 2 l of water stirred for 1 h, filtered off with suction from the solid and washed once with 300 ml of water.
  • the solid After dry suction, the solid is re-suspended in 1 1 15 wt .-% ammonia solution and stirred for one hour, filtered off again, washed the solid until neutral reaction with water and then sucked dry.
  • the solid is dissolved in 500 ml of dichloromethane, the solution is washed with sat. Saline washed, the org. Phase is dried over magnesium sulfate. After removal of the drying agent, the solution is concentrated and the glassy residue is acidified once with Alox, basic, activity level 1 and once with silica gel with dichloromethane. The viscous oil thus obtained is replaced by two times fractionated Kugelrohr distillation of low boilers and non-volatile secondary components freed. Yield: 15.2 g (55 mmol), 55%; Purity: about 99.5% after 1 H NMR.
  • Phenylboronic acid [98-80-6], 5.8 g (30 mmol) of tripotassium phosphate, 123 mg (0.5 mmol) of palladium (II) acetate, 913 mg (3 mmol) of tri-o-tolylphosphine, 20 ml of toluene, 10 ml of dioxane and 30 ml of water is refluxed for 16 h.
  • inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the following examples introduce the results of different OLEDs.
  • Glass plates with structured ITO indium tin oxide form the substrates onto which the OLEDs are applied.
  • the OLEDs have in principle the following layer structure: substrate / hole transport layer 1 (HTL1) consisting of HTM doped with 3% NDP-9 (commercially available from Novaled), 20 nm / hole transport layer 2 (HTL2) / optional hole transport layer 3 (HTL3) / Emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional
  • HTL1 substrate / hole transport layer 1
  • HTM hole transport layer 2
  • HTL3 optional hole transport layer 3
  • Emission layer Emission layer
  • HBL optional hole blocking layer
  • ETL electron transport layer
  • Electron injection layer EIL
  • cathode is formed by a 100 nm thick aluminum layer.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter) which passes through the matrix material or the matrix materials
  • Cover vaporization is mixed in a certain volume fraction.
  • the electron transport layer may consist of a mixture of two materials. The exact structure of the OLEDs is shown in Table 1. The materials used to make the OLEDs are shown in Table 4.
  • the OLEDs are characterized by default. For this, the electroluminescence spectra, the current efficiency (measured in cd / A) and the voltage (measured at 1000 cd / m 2 in V) are determined from current
  • the lifetime is defined as the time after which the luminance has dropped to a certain level from a certain starting luminance.
  • the term LD50 means that the stated lifetime is the time at which the luminance has fallen to 50% of the starting luminance, ie from 1000 cd / m 2 to 500 cd / m 2 .
  • the values for the lifetime can be converted to an indication for other starting luminous densities with the aid of conversion formulas known to the person skilled in the art.
  • the life for a starting luminous flux of 1000 cd / m 2 is a common statement.
  • the compounds according to the invention can be used inter alia as triplex matrix material (TMM), electron transport material (ETM), hole blocking material (HBM), blue singlet matrix material (SMB) and blue singlet emitter (SEB) in OLEDs.
  • TMM triplex matrix material
  • ETM electron transport material
  • HBM hole blocking material
  • SMB blue singlet matrix material
  • SEB blue singlet emitter
  • the compounds according to the invention can also be processed from solution and lead there to much simpler process technology
  • OLEDs compared to the vacuum-processed OLEDs, with nevertheless good properties.
  • the production of such components is based on the production of polymeric light-emitting diodes (PLEDs), which has already been described many times in the literature (for example in WO 2004/037887).
  • the structure is composed of substrate / ITO / PEDOT (80 nm) / interlayer (80 nm) / emission layer (80 nm) / cathode.
  • substrates of the company Technoprint Sodalimeglas
  • the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by a UV / ozone plasma treatment. Thereafter, also in the clean room as
  • Buffer layer an 80 nm layer of PEDOT (PEDOT is a polythiophene derivative (Baytron P VAI 4083sp.) From HC Starck, Goslar, as aqueous Dispersion is supplied) applied by spin coating.
  • PEDOT is a polythiophene derivative (Baytron P VAI 4083sp.) From HC Starck, Goslar, as aqueous Dispersion is supplied) applied by spin coating.
  • the required spin rate depends on the degree of dilution and the specific spin coater geometry (typically 80 nm: 4500 rpm).
  • the substrates are baked for 10 minutes at 180 ° C on a hot plate.
  • the used interlayer serves the
  • HIL-012 is used by Merck.
  • Interlayer can alternatively be replaced by one or more layers, which only have to fulfill the condition by which
  • the emitters according to the invention are used together with the
  • Matrix materials dissolved in toluene The typical solids content of such solutions is between 16 and 25 g / L, if, as here, the typical for a device layer thickness of 80 nm is to be achieved by spin coating.
  • the solution-processed devices contain an emission layer
  • Emission layer is spun in an inert gas atmosphere, in the present case argon, and baked at 130 ° C for 30 min. Finally, a cathode is made of barium (5 nm) and then aluminum (100 nm) (high purity metals from Aldrich, especially barium 99.99% (stock number 474711);

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EP14752276.7A 2013-09-11 2014-08-13 Heterocyclische verbindungen Withdrawn EP3044285A1 (de)

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US20200129485A1 (en) 2018-09-19 2020-04-30 Forma Therapeutics, Inc. Treating sickle cell disease with a pyruvate kinase r activating compound
KR20210065972A (ko) 2018-09-27 2021-06-04 메르크 파텐트 게엠베하 입체 장애 함질소 헤테로방향족 화합물의 제조 방법
CN112739795A (zh) * 2018-09-27 2021-04-30 默克专利有限公司 可用作有机电子器件中的活性化合物的化合物
CN114409666B (zh) * 2021-12-06 2022-12-09 江西中医药大学 一种从沙棘中分离的高异黄酮骈木脂素化合物及其制备抗非酒精性脂肪肝药物的用途

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JP6576929B2 (ja) 2019-09-18
US20160226003A1 (en) 2016-08-04
CN105531348A (zh) 2016-04-27
CN105531348B (zh) 2017-11-07
KR20160052716A (ko) 2016-05-12

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