EP3938367A1 - Matériaux pour dispositifs électroluminescents organiques - Google Patents

Matériaux pour dispositifs électroluminescents organiques

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Publication number
EP3938367A1
EP3938367A1 EP20708117.5A EP20708117A EP3938367A1 EP 3938367 A1 EP3938367 A1 EP 3938367A1 EP 20708117 A EP20708117 A EP 20708117A EP 3938367 A1 EP3938367 A1 EP 3938367A1
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European Patent Office
Prior art keywords
aromatic
radicals
substituted
group
ring system
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
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EP20708117.5A
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German (de)
English (en)
Inventor
Amir Parham
Jonas Kroeber
Jens ENGELHART
Christian Ehrenreich
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of EP3938367A1 publication Critical patent/EP3938367A1/fr
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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
    • C07D487/02—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
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—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
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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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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
    • H10K85/658—Organoboranes
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • H—ELECTRICITY
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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
    • H10K50/15—Hole transporting layers
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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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and electronic devices, in particular organic electroluminescent devices containing them
  • OLEDs organic electroluminescent devices
  • phosphorescent organometallic complexes are often used as emitting materials.
  • OLEDs organic electroluminescent devices
  • the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials, are of particular importance here. Improvements in these materials can therefore also lead to improvements in the OLED properties.
  • Suitable matrix materials for OLEDs are, for example, aromatic lactams, such as. B. in WO 2011/116865, WO
  • the object of the present invention is to provide compounds which are suitable for use in an OLED, in particular as matrix material for phosphorescent emitters or as electron transport material, and which lead to good properties there.
  • the present invention relates to a compound of the formula (1),
  • X identically or differently on each occurrence, is CR or N; or two adjacent groups X represent a group of the following formula (2), and the other symbols X are identical or different on each occurrence for CR or N,
  • Y is CR or N
  • a 1 is identically or differently on each occurrence NAr 2 , S or
  • Z is CR or N;
  • Ar 1 is an aromatic ring system with 6 to 40 aromatic ring atoms, which can be substituted by one or more radicals R, or an electron-rich heteroaromatic ring system with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R.
  • R radicals
  • Y CR an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which with one or more
  • Radicals R can be substituted
  • Ar 2 is an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R;
  • R is on each occurrence, identically or differently, H, D, F, CI, Br, I,
  • Ar ' is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 1 ;
  • R 2 is on each occurrence, identically or differently, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, with 1 to 20 carbon atoms, in which one or more H atoms are also replaced by F could be.
  • an aryl group contains 6 to 40 carbon atoms;
  • a heteroaryl group contains 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, 0 and / or S.
  • an aryl group or heteroaryl group either a simple aromatic cycle, i.e.
  • benzene or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
  • aromatics linked to one another by a single bond, such as biphenyl are not referred to as an aryl or heteroaryl group, but as an aromatic ring system.
  • An aromatic ring system for the purposes of this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, in the ring system.
  • a heteroaromatic ring system for the purposes of this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and hetero atoms is at least 5.
  • the heteroatoms are preferably selected from N, 0 and / or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system that does not necessarily contain only aryl or heteroaryl groups, but also in which several aryl or heteroaryl groups are replaced by a non-aromatic Unit, such as B.
  • Phenyl pyridine for example, systems such as fluorene, 9,9‘-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems for the purposes of this invention, and likewise systems in which two or more aryl groups
  • aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups and groups in which two or more aryl or heteroaryl groups are linked directly to one another, for example biphenyl or bipyridine, and fluorene or spirobifluorene.
  • An electron-rich heteroaromatic ring system is characterized in that it is a heteroaromatic ring system which does not contain any electron-poor heteroaryl groups.
  • An electron-deficient heteroaryl group is a six-membered ring heteroaryl group with at least one nitrogen atom or a five-membered ring heteroaryl group with at least two heteroatoms, one of which is a nitrogen atom and the other is oxygen, sulfur or a substituted nitrogen atom, with further aryl or heteroaryl on these groups groups can be condensed.
  • electron-rich heteroaryl groups are five-membered ring heteroaryl groups with exactly one hetero atom, selected from oxygen, sulfur or substituted nitrogen, to which further aryl groups and / or further electron-rich five-membered heteroaryl groups can be fused.
  • electron-rich heteroaryl groups are pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene or indenocarbazole.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 40 carbon atoms, and in which also individual H atoms or CH 2 groups are represented by the above-mentioned groups can be substituted, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl , Cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cyclo-heptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoro
  • alkoxy group OR 1 with 1 to 40 carbon atoms, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s- Pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
  • a thioalkyl group SR 1 with 1 to 40 carbon atoms includes, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio,
  • Pentenylthio Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethynylthio,
  • Thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, it being possible for one or more non-adjacent CH 2 groups to be replaced by the abovementioned groups; Furthermore, one or more H atoms can also be replaced by D, F, CI, Br, I,
  • CN or N0 2 preferably F, CI or CN, particularly preferably F or CN, be replaced.
  • aromatic or heteroaromatic ring system with 5-60 aromatic ring atoms which can be substituted by the above mentioned radicals R 2 or a hydrocarbon radical and which can be linked via any positions on the aromatic or heteroaromatic, in particular groups are understood which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, Pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, spirotruxen, isotru
  • the compounds of the following formulas (5) and (6) are therefore preferred, Formula (5) Formula (6) where the symbols used have the meanings given above.
  • a maximum of one symbol X per cycle represents N, and the other symbols X, identically or differently, represent CR. In a particularly preferred embodiment of the invention, all symbols X, identically or differently, stand for CR.
  • two adjacent groups X stand for a group of the formula (2) and the other symbols X stand, identically or differently, for CR or N. If two Adjacent groups X represent a group of the formula (2), the group of the formula (2) is preferably bonded to the six-membered ring which is fused to the lactam ring and not to the six-membered ring which is fused to the five-membered ring.
  • the symbol A 1 in the group of the formula (2) preferably stands for NAr 2 .
  • a maximum of one group X is preferably N, and the other groups X are identical or different and are CR. Particularly preferably, all groups X, identically or differently, represent CR.
  • At most one group Z stands for N, and the other groups Z, identically or differently, stand for CR. It is particularly preferable for all of the Z groups, identically or differently, to represent CR.
  • the abovementioned preferences for X and Z in the formulas (17) to (20) particularly preferably occur simultaneously, so that the compounds of the following formulas (17-1) to (20-1) are particularly preferred,
  • a total of a maximum of three radicals R, particularly preferably a maximum of two radicals R and very particularly preferably a maximum of one radical R in the compounds of the formulas (17-1) to (20-1) represent a group other than hydrogen.
  • Ar 1 stands for a heteroaryl group, in particular for carbazole, aromatic or heteroaromatic substituents R on this heteroaryl group preferred.
  • Ar 1 is substituted by a group N (Ar ') 2 , so that the substituent Ar 1 as a whole represents a triarylamine or triheteroarylamine group.
  • Ar 1 stands for a heteroaryl group, in particular for triazine, pyrimidine, quinazoline or carbazole, aromatic or heteroaromatic substituents R on this heteroaryl group can also be preferred.
  • Ar 1 is substituted by a group N (Ar ') 2 , so that the substituent Ar 1 as a whole represents a triarylamine or triheteroarylamine group.
  • Ar 2 is an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted by one or more radicals R.
  • Ar 2 is particularly preferably an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 12 aromatic ring atoms, which can be substituted by one or more, preferably non-aromatic, radicals R.
  • Ar 2 stands for a heteroaryl group, in particular for triazine, pyrimidine, quinazoline or carbazole, aromatic or heteroaromatic substituents R on this heteroaryl group can also be preferred.
  • Ar 2 is substituted by a group N (Ar ') 2 , so that the substituent Ar 2 represents a triaryl amine or triheteroarylamine group as a whole.
  • Suitable aromatic or heteroaromatic ring systems Ar 1 or Ar 2 are selected identically or differently on each occurrence from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl , Quater- phenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which is linked via the 1-, 2-, 3-position - or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1-, 2-, 3- or 4-position , Dibenzofuran, which can be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position
  • Ar 1 or Ar 2 stands for a heteroaryl group, in particular for triazine, pyrimidine, quinazoline or carbazole, aromatic or heteroaromatic radicals R on this heteroaryl group can also be preferred.
  • R is selected on each occurrence identically or differently from the group consisting of H, D, F, N (Ar ') 2 , CN, OR 1 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group can be substituted by one or more radicals R 1 , but is preferably unsubstituted, and where one or more non-adjacent CH 2 groups can be replaced by O, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 ; two radicals R can also be aliphatic, aromatic or heteroaromatic with one another Form ring system.
  • R is particularly preferably selected identically or differently on each occurrence from the group consisting of H, N (Ar ') 2 , a straight-chain alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group can in each case be substituted with one or more radicals R 1 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each can be substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 .
  • R is very particularly preferably selected identically or differently on each occurrence from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which is represented by one or more radicals R 1 , preferably non-aromatic radicals R 1 , can be substituted. It can furthermore be preferred if R stands for a triaryl or -heteroarylamine group which can be substituted by one or more radicals R 1 .
  • This group is an embodiment of an aromatic or heteroaromatic ring system, in which case several aryl or
  • Heteroaryl groups are linked together by a nitrogen atom. If R stands for a triaryl or heteroarylamine group, this group preferably has 18 to 30 aromatic ring atoms and can be substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 .
  • Ar ' is an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 .
  • Ar ' is an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 13 aromatic ring atoms, which can be substituted by one or more, preferably non-aromatic, radicals R 1 .
  • Suitable aromatic or heteroaromatic ring systems R or Ar ' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or ver branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which is linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1-, 2-, 3- or 4-position can be linked, dibenzofuran, which can be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole , Indoloc
  • Phenanthrene triphenylene or a combination of two or three of these groups, each of which can be substituted with one or more radicals R 1 . If R or Ar 'stands for a heteroaryl group, in particular triazine, pyrimidine or quinazoline, aromatic or heteroaromatic radicals R 1 on this heteroaryl group can also be preferred.
  • R if they stand for an aromatic or heteroaromatic ring system, or Ar 'are preferably selected from the groups of the following formulas R-1 to R-76,
  • Ar 3 is on each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each with one or more radicals
  • R 1 can be substituted
  • Groups are embodiments of Ar '.
  • a 1 stands for NR or NR 1
  • the substituent R or R 1 which is bonded to the nitrogen atom, preferably stands for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which is also characterized by one or more radicals R 1 or R 2 can be substituted.
  • this substituent R or R 1 identically or differently on each occurrence, represents an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which have no condensed aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are fused directly to one another, and which in each case can also be substituted by one or more radicals R 1 or R 2 .
  • Phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for Ar-1 to Ar-11 or R-1 to R-11 are particularly preferred, these structures being represented by one or more radicals R 1 or R 2 may be substituted, but are preferably unsubstituted.
  • a 1 stands for C (R) 2 or C (R 1 ) 2
  • the substituents R and R 1 which are bonded to this carbon atom, are preferably identical or different on each occurrence for a linear alkyl group with 1 to 10 carbon atoms or for a branched or cyclic alkyl group with 3 to 10 carbon atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 1 or R 2 .
  • R or R 1 very particularly preferably represents a methyl group or a phenyl group.
  • the radicals R and R 1 can also form a ring system with one another, which leads to a spiro system.
  • At least one radical R is an electron-rich heteroaromatic ring system.
  • the electron-rich heteroaromatic ring system is preferably selected from the groups R-13 to R-42 shown above, where in the groups R-13 to R-16, R-18 to R-20, R-22 to R-24, R -27 to R-29, R-31 to R-33 and R-35 to R-37 at least one group A 1 represents NR 1 , where R 1 preferably represents an aromatic or heteroaromatic ring system, in particular an aromatic ring system.
  • At least one radical R is an electron-poor heteroaromatic ring system.
  • the electron-poor heteroaromatic ring system is preferably selected from the groups R-47 to R-50, R-57, R-58 and R-76 shown above.
  • R 1 identically or differently on each occurrence, is selected from the group consisting of H, D, F, CN, OR 2 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, where the alkyl or alkenyl group can in each case be substituted by one or more radicals R 2 and one or more non-adjacent CH 2 groups have been replaced by O.
  • R 1 can, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 ; two or more radicals R 1 here can form an aliphatic ring system with one another.
  • R 1, identically or differently on each occurrence, is selected from the group consisting of H, one
  • alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, it being possible for the alkyl group to be substituted by one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic table ring atoms, each of which can be substituted by one or more radicals R 2 , but is preferably unsubstituted.
  • R 2 identically or differently on each occurrence, is H, F, an alkyl group with 1 to 4 carbon atoms or an aryl group with 6 to 10 carbon atoms, which is associated with an alkyl group with 1 to 4 carbon atoms Atoms can be substituted, but is preferably unsubstituted.
  • Ar 1 , Ar 2 , R or Ar ' are groups of the formula -Ar 6 -N (Ar 4 ) (Ar 5 ), where Ar 4 , Ar 5 and Ar 6, identically or differently on each occurrence, represent an aromatic or a heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1 .
  • Ar 1 or Ar 2 such a group results in that the group Ar 1 or Ar 2 is substituted by a group N (Ar ') 2 .
  • the total number of aromatic ring atoms of Ar 4 , Ar 5 and Ar 6 is a maximum of 60 and preferably a maximum of 40.
  • Ar 6 and Ar 4 can be connected to one another and / or Ar 4 and Ar 5 to one another by a group selected from C (R 1 ) 2, NR 1 , O or S.
  • the linkage of Ar 6 and Ar 4 to one another or of Ar 4 and Ar 5 to one another preferably takes place in each case ortho to the position of the linkage with the nitrogen atom.
  • none of the groups Ar 4 , Ar 5 or Ar 6 are connected to one another.
  • Ar 6 is preferably an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 12 aromatic ring atoms, which can be substituted by one or more radicals R 1 .
  • Ar 6 is particularly preferably selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, which can each be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • Ar 6 is very particularly preferably an unsubstituted phenylene group. This is especially true when Ar 6 is linked to Ar 4 by a single bond
  • Ar 4 and Ar 5 are preferably, identically or differently on each occurrence, an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1 .
  • Particularly preferred groups Ar 4 and Ar 5 are selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta -, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4- spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene,
  • Ar 4 and Ar 5 identically or differently on each occurrence, represent an aromatic ring system with 6 to 24 aromatic ring atoms, which can be substituted by one or more radicals R 1 , in particular selected from the groups consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, in particular 1 -, 2 -, 3- or 4-fluorene, or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobifluorene.
  • R 1 radicals
  • the alkyl groups in compounds according to the invention which are processed by vacuum evaporation preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms, very particularly preferably no more than 1 carbon atom.
  • compounds are also suitable which are substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms or which are substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups.
  • the compounds of the formula (1) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer that is directly adjacent to a phosphorescent layer, it is further preferred if the compound does not contain condensed aryl or contains heteroaryl groups in which more than two six-membered rings are fused directly to one another.
  • the radicals Ar 1 , Ar 2 , R, Ar ′, R 1 and R 2 contain no condensed aryl or heteroaryl groups in which two or more six-membered rings are fused directly to one another.
  • the basic structure of the compounds according to the invention can be represented by the routes outlined in Schemes 1 and 2.
  • the basic structure is built up, which does not yet have an Ar 1 group.
  • the synthesis of the backbone is known in the literature.
  • the group Ar 1 can then be introduced in a next step with a coupling reaction, for example a Ullmann coupling or a Hartwig-Buchwald coupling.
  • a coupling reaction for example a Ullmann coupling or a Hartwig-Buchwald coupling.
  • a reactive leaving group such as chlorine or bromine
  • the present invention therefore also provides a method for the preparation of the compounds according to the invention, characterized by the following steps:
  • formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures for this purpose use two or more solvents.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, ( -) - fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5-tetramethylbenzene, 1 - methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3 , 4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzen
  • the present invention therefore also provides a formulation containing a compound according to the invention and at least one further compound.
  • the further compound can, for example, be a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents.
  • the further compound can, however, also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and / or a further matrix material. Suitable emitting compounds and other matrix materials are listed below in connection with the organic electric luminescent device.
  • This further compound can also be polymeric.
  • the compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device.
  • Another object of the present invention is therefore the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • Yet another subject matter of the present invention is an electronic device containing at least one compound according to the invention.
  • An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or layers that are made entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic Laser diodes (O lasers) and “organic plasmon emitting devices”, but preferably organic electroluminescent devices (OLEDs), particularly preferably phosphorescent OLEDs.
  • OLEDs organic electroluminescent devices
  • O-ICs organic integrated circuits
  • O-FETs organic field-effect transistors
  • OF-TFTs organic thin-film transistors
  • O-LETs organic light-emitting transistors
  • O-SCs organic solar cells
  • the organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can also contain other layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. As well Interlayers can be introduced between two emitting layers, which, for example, have an exciton-blocking function.
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H.
  • Various emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, the three layers showing blue, green and orange or red emission.
  • the organic electroluminescent device according to the invention can also be one
  • the compound according to the invention according to the embodiments listed above can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device containing a compound according to formula (1) or the preferred embodiments set out above in an emitting layer as a matrix material for phosphorescent emitters or for emitters showing TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters.
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers, at least one emitting layer containing at least one compound according to the invention as a matrix material.
  • the compound according to the invention can also be used in an electron transport layer and / or in a hole blocking layer and / or in a hole transport layer and / or in an exciton blocking layer.
  • the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
  • phospho- Rescence in the context of this invention is understood to mean the luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 80% by volume of the compound according to the invention, based on the Total mixture of emitter and matrix material.
  • the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter based on the total mixture Emitter and matrix material.
  • Another preferred embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with a further matrix material.
  • Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. B.
  • CBP N, N-biscarbazolylbiphenyl
  • CBP N, N-biscarbazolylbiphenyl
  • indolocarbazole derivatives e.g. B. according to WO 2007/063754 or WO 2008/056746
  • indenocarbazole derivatives e.g. B. according to WO
  • bipolar matrix materials e.g. B. according to WO 2007/137725, silanes, e.g. B. according to WO 2005/111172, aza borole or boronic ester, z. B. according to WO 2006/117052, triazine derivatives, z. B. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877, zinc complexes, e.g. B. according to EP 652273 or WO 2009/062578, diazasilol or tetra azasilol derivatives, z.
  • a further phosphorescent emitter which emits with a shorter wave than the actual emitter, can also be present as a co-host in the mixture, or a compound that does not participate or does not participate to a significant extent in the charge transport, as described, for example, in WO 2010/108579.
  • co-matrix materials especially if the compound according to the invention is substituted with an electron-poor heteroaromatic ring system, are selected from the group of bis-carbazoles, bridged carbazoles, triarylamines, dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives and the Carbazolamines.
  • Preferred biscarbazoles are the structures of the following formulas (21) and (22),
  • a 1 stands for CR2.
  • Preferred embodiments of the compounds of the formulas (21) and (22) are the compounds of the following formulas (21a) and (22a),
  • Examples of suitable compounds according to formula (21) or (22) are the compounds shown below.
  • Preferred bridged carbazoles are the structures of the following formula (23),
  • a 1 and R have the meanings given above and A 1 is preferably selected identically or differently on each occurrence from the group consisting of NAr 1 and CR 2.
  • Preferred dibenzofuran derivatives are the compounds of the following formula (24), where the oxygen can also be replaced by sulfur, so that a dibenzothiophene is formed, L stands for a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can also be substituted by one or more radicals R, and R and Ar 1 have the meanings given above.
  • the two groups Ar 1 which bind to the same nitrogen atom, or a group Ar 1 and a group L, which bind to the same nitrogen atom, can also be connected to one another, for example to form a carbazole.
  • Examples of suitable dibenzofuran derivatives are the compounds shown below.
  • Preferred carbazolamines are the structures of the following formulas (25), (26) and (27),
  • L stands for an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R, and R and Ar 1 have the meanings given above.
  • Examples of suitable carbazolamine derivatives are the compounds shown below.
  • Preferred co-matrix materials especially if the compound according to the invention is substituted with an electron-rich heteroaromatic ring system, for example a carbazole group, are further selected from the group consisting of triazine derivatives, pyrimidine derivatives and quinazoline derivatives.
  • Preferred triazine, Quinazoline or pyrimidine derivatives which can be used as a mixture together with the compounds according to the invention, are the compounds of the following formulas (28), (29) and (30),
  • the triazine derivatives of the formula (28) and the quinazoline derivatives of the formula (30), in particular the triazine derivatives of the formula (28), are particularly preferred.
  • Ar 1 in the formulas (28), (29) and (30) is, identically or differently, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, in particular with 6 to 24 aromatic ring atoms, on each occurrence can be substituted by one or more radicals R.
  • Suitable aromatic or heteroaromatic ring systems Ar 1 are the same as those set out above as embodiments for Ar 1 and Ar 2 , in particular the structures Ar-1 to Ar-76.
  • Suitable triazine compounds which can be used as matrix materials together with the compounds according to the invention are the compounds shown in the table below.
  • Suitable quinazoline compounds are the compounds shown in the following table:
  • Particularly suitable phosphorescent compounds are compounds which, when suitably excited, emit light, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 , especially a metal with this atomic number.
  • Preferred phosphorescent emitter compounds are copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are used, in particular compounds containing iridium or platinum.
  • Examples of phosphorescent dopants are listed below.
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated with a sublimation process.
  • the materials in vacuum sublimation systems become smaller at an initial pressure
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) process or with the aid of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 5 mbar and 1 bar.
  • OVJP Organic Vapor Jet Printing
  • OVJP Organic Vapor Jet Printing
  • an organic electroluminescent device characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • any printing process such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • Hybrid processes are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished by one or more of the following properties:
  • the compounds according to the invention used as matrix material for phosphorescent emitters, lead to long lifetimes.
  • the compounds according to the invention lead to high efficiencies, in particular to a high EQE. This is particularly true when the compounds are used as matrix material for a phosphorescent emitter.
  • the compounds according to the invention lead to low operating voltages. This is especially true when the connections are considered Matrix material can be used for a phosphorescent emitter.
  • the rotary evaporator is concentrated, the precipitated solid is filtered off with suction and washed with water and ethanol.
  • the crude product is purified twice by means of a hot extractor (toluene / heptane 1: 1) and the solid obtained is recrystallized from toluene. After sublimation, 8.2 g (12 mmol, 48%) of the product are obtained.
  • the following connections can be established in the same way:
  • Glass platelets 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 coating. This with Plasma-treated glass platelets form the substrates on 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) / electron blocking layer (EBL) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) and finally a cathode.
  • the cathode is formed by a 100 nm thick aluminum layer.
  • Tables 1 a to 1 c The data of the OLEDs are listed in Tables 2a to 2c.
  • the materials required to produce 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 mixed into the matrix material or matrix materials in a certain volume proportion by co-vaporization.
  • a specification such as IC1: 19a: TEG (45%: 45%: 10%) means that the material IC1 in a volume fraction of 45%, the material 19a in a volume fraction of 45% and TEG in a volume fraction of 10% in the layer is present.
  • the electron transport layer or one of the other layers can also consist of a mixture of two materials.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra and the external quantum efficiency (EQE, measured in%) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics, assuming a Lambertian emission 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 .
  • the materials according to the invention are used in Examples E1 to E4 and E9 as matrix material in the emission layer of green-phosphorescent OLEDs.
  • ETL or HBL of blue fluorescent OLEDs Another material according to the invention is used in Examples E7 and E8 as ETL or HBL of blue fluorescent OLEDs. Use as ETL and HBL in phosphorescent OLEDs is also possible.

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Abstract

La présente invention concerne des composés appropriés à une utilisation dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant ces composés.
EP20708117.5A 2019-03-12 2020-03-10 Matériaux pour dispositifs électroluminescents organiques Pending EP3938367A1 (fr)

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Family Cites Families (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4000275A (en) * 1969-11-24 1976-12-28 Eli Lilly And Company Immunosuppressants
DE3208218A1 (de) * 1982-03-06 1983-09-08 Basf Ag, 6700 Ludwigshafen Isoindolinfarbstoffe und deren verwendung
JPH07133483A (ja) 1993-11-09 1995-05-23 Shinko Electric Ind Co Ltd Ｅｌ素子用有機発光材料及びｅｌ素子
EP2306495B1 (fr) 1999-05-13 2017-04-19 The Trustees of Princeton University Dispositifs électroluminescents organiques a trés haute performance utilisant l'électrophosphorescence
CN1224297C (zh) 1999-12-01 2005-10-19 普林斯顿大学理事会 作为有机发光器件的磷光掺杂剂的l2mx形式的络合物
US6660410B2 (en) 2000-03-27 2003-12-09 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
GB0017508D0 (en) * 2000-07-17 2000-08-30 Novartis Ag Antimicrobials
EP1325671B1 (fr) 2000-08-11 2012-10-24 The Trustees Of Princeton University Composes organometalliques et electrophosphorescence organique presentant un deplacement d'emission
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 金属配位化合物
JP4154139B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子
JP4154138B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子、表示装置及び金属配位化合物
ITRM20020411A1 (it) 2002-08-01 2004-02-02 Univ Roma La Sapienza Derivati dello spirobifluorene, loro preparazione e loro uso.
JP4411851B2 (ja) 2003-03-19 2010-02-10 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子
EP2281861A3 (fr) 2003-04-15 2012-03-28 Merck Patent GmbH Mélanges de semi-conducteurs organiques destinés à l'émission et matériaux de matrice, leur utilisation et composants électroniques pourvus de ces mélanges
WO2004095890A1 (fr) 2003-04-23 2004-11-04 Konica Minolta Holdings, Inc. Matiere pour dispositif electroluminescent organique, dispositif electroluminescent organique, dispositif d'eclairage et affichage
DE10338550A1 (de) 2003-08-19 2005-03-31 Basf Ag Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs)
DE10345572A1 (de) 2003-09-29 2005-05-19 Covion Organic Semiconductors Gmbh Metallkomplexe
US7795801B2 (en) 2003-09-30 2010-09-14 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
US7790890B2 (en) 2004-03-31 2010-09-07 Konica Minolta Holdings, Inc. Organic electroluminescence element material, organic electroluminescence element, display device and illumination device
DE102004023277A1 (de) 2004-05-11 2005-12-01 Covion Organic Semiconductors Gmbh Neue Materialmischungen für die Elektrolumineszenz
US7598388B2 (en) 2004-05-18 2009-10-06 The University Of Southern California Carbene containing metal complexes as OLEDs
JP4862248B2 (ja) 2004-06-04 2012-01-25 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
ITRM20040352A1 (it) 2004-07-15 2004-10-15 Univ Roma La Sapienza Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso.
CN101171320B (zh) 2005-05-03 2013-04-10 默克专利有限公司 有机电致发光器件
CN102633820B (zh) 2005-12-01 2015-01-21 新日铁住金化学株式会社 有机电致发光元件用化合物及有机电致发光元件
DE102006025777A1 (de) 2006-05-31 2007-12-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
US8062769B2 (en) 2006-11-09 2011-11-22 Nippon Steel Chemical Co., Ltd. Indolocarbazole compound for use in organic electroluminescent device and organic electroluminescent device
DE102007002714A1 (de) 2007-01-18 2008-07-31 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102007053771A1 (de) 2007-11-12 2009-05-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102008027005A1 (de) 2008-06-05 2009-12-10 Merck Patent Gmbh Organische elektronische Vorrichtung enthaltend Metallkomplexe
DE102008033943A1 (de) 2008-07-18 2010-01-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008036247A1 (de) 2008-08-04 2010-02-11 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend Metallkomplexe
DE102008036982A1 (de) 2008-08-08 2010-02-11 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102008048336A1 (de) 2008-09-22 2010-03-25 Merck Patent Gmbh Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen
DE102008056688A1 (de) 2008-11-11 2010-05-12 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
WO2010054730A1 (fr) 2008-11-11 2010-05-20 Merck Patent Gmbh Dispositifs électroluminescents organiques
DE102008057050B4 (de) 2008-11-13 2021-06-02 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102008057051B4 (de) 2008-11-13 2021-06-17 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009007038A1 (de) 2009-02-02 2010-08-05 Merck Patent Gmbh Metallkomplexe
DE102009011223A1 (de) 2009-03-02 2010-09-23 Merck Patent Gmbh Metallkomplexe
DE102009013041A1 (de) 2009-03-13 2010-09-16 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009014513A1 (de) 2009-03-23 2010-09-30 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102009023155A1 (de) 2009-05-29 2010-12-02 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009031021A1 (de) 2009-06-30 2011-01-05 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009053644B4 (de) 2009-11-17 2019-07-04 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009053645A1 (de) 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtung
DE102009041414A1 (de) 2009-09-16 2011-03-17 Merck Patent Gmbh Metallkomplexe
DE102009048791A1 (de) 2009-10-08 2011-04-14 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009053382A1 (de) 2009-11-14 2011-05-19 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009053836A1 (de) 2009-11-18 2011-05-26 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009057167A1 (de) 2009-12-05 2011-06-09 Merck Patent Gmbh Elektronische Vorrichtung enthaltend Metallkomplexe
DE102010005697A1 (de) 2010-01-25 2011-07-28 Merck Patent GmbH, 64293 Verbindungen für elektronische Vorrichtungen
DE102010012738A1 (de) 2010-03-25 2011-09-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010019306B4 (de) 2010-05-04 2021-05-20 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
CN102939296B (zh) * 2010-06-15 2016-02-10 默克专利有限公司 金属络合物
DE102010027317A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
DE102010048608A1 (de) 2010-10-15 2012-04-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
EP2699571B1 (fr) 2011-04-18 2018-09-05 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
US9818948B2 (en) 2011-09-21 2017-11-14 Merck Patent Gmbh Carbazole derivatives for organic electroluminescence devices
US9515266B2 (en) 2011-10-20 2016-12-06 Merck Patent Gmbh Materials for organic electroluminescent devices
KR102021162B1 (ko) 2011-11-01 2019-09-11 메르크 파텐트 게엠베하 유기 전계발광 소자
KR102115141B1 (ko) * 2012-06-18 2020-05-26 미쯔비시 케미컬 주식회사 고분자 화합물, 전하 수송성 폴리머, 유기 전계 발광 소자용 조성물, 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명
US9837622B2 (en) 2012-07-13 2017-12-05 Merck Patent Gmbh Metal complexes
JP6363075B2 (ja) 2012-08-07 2018-07-25 メルク パテント ゲーエムベーハー 金属錯体
JP6556629B2 (ja) 2012-12-21 2019-08-07 メルク パテント ゲーエムベーハー 金属錯体
KR102188214B1 (ko) 2012-12-21 2020-12-08 메르크 파텐트 게엠베하 금속 착물
US9831448B2 (en) 2013-09-11 2017-11-28 Merck Patent Gmbh Metal complexes
KR101656942B1 (ko) 2013-09-30 2016-09-12 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
US11005050B2 (en) 2014-01-13 2021-05-11 Merck Patent Gmbh Metal complexes
EP3102650B1 (fr) 2014-02-05 2018-08-29 Merck Patent GmbH Complexes métalliques
CN114394958A (zh) 2014-05-05 2022-04-26 默克专利有限公司 用于有机发光器件的材料
WO2016015815A1 (fr) 2014-07-28 2016-02-04 Merck Patent Gmbh Complexes métalliques
CN106661006B (zh) 2014-07-29 2019-11-08 默克专利有限公司 用于有机电致发光器件的材料
US9876181B2 (en) 2014-08-13 2018-01-23 Merck Patent Gmbh Materials for organic electroluminescent devices
KR102554987B1 (ko) 2015-02-03 2023-07-12 메르크 파텐트 게엠베하 금속 착물
WO2017032439A1 (fr) 2015-08-25 2017-03-02 Merck Patent Gmbh Complexes métalliques
TW201718583A (zh) * 2015-11-23 2017-06-01 Nanjing Sanhome Pharmaceutical Co Ltd 新的表皮生長因子受體抑制劑及其應用
JP7080821B2 (ja) 2016-03-03 2022-06-06 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
TWI749026B (zh) 2016-07-14 2021-12-11 德商麥克專利有限公司 金屬錯合物
WO2018041769A1 (fr) 2016-08-30 2018-03-08 Merck Patent Gmbh Complexes métalliques binucléaires et trinucléaires obtenus à partir de deux ligands hexadentés tripodaux liés entre eux, destinés à être utilisés dans des dispositifs électroluminescents
CN106749273B (zh) * 2016-12-16 2020-05-15 中节能万润股份有限公司 一种母核为喹唑啉酮衍生物的化合物及其应用
US11569458B2 (en) 2017-03-29 2023-01-31 Merck Patent Gmbh Metal complexes
TWI776926B (zh) 2017-07-25 2022-09-11 德商麥克專利有限公司 金屬錯合物

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