WO2023052314A1 - Matériaux pour dispositifs électroniques - Google Patents

Matériaux pour dispositifs électroniques Download PDF

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WO2023052314A1
WO2023052314A1 PCT/EP2022/076741 EP2022076741W WO2023052314A1 WO 2023052314 A1 WO2023052314 A1 WO 2023052314A1 EP 2022076741 W EP2022076741 W EP 2022076741W WO 2023052314 A1 WO2023052314 A1 WO 2023052314A1
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aromatic
groups
substituted
radicals
formula
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PCT/EP2022/076741
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Philipp Stoessel
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Merck Patent Gmbh
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and electronic devices, in particular organic electroluminescent devices containing these materials.
  • Organic-based charge transport materials e.g. triarylamine-based hole transporters
  • organic or polymer light-emitting diodes OLEDs or PLEDs
  • O-SC organic solar cells
  • O-FET organic field effect transistors
  • O-TFT organic thin-film transistors
  • O-IC organic switching elements
  • O-lasers organic laser diodes
  • Electronic devices within the meaning of this invention are understood to mean organic electronic devices which contain organic semiconductor materials as functional materials.
  • the electronic devices stand for electroluminescent devices such as OLEDs.
  • OLEDs in which organic compounds are used as functional materials are known to the person skilled in the art from the prior art.
  • OLEDs are electronic devices that have one or more layers that include organic compounds and emit light when a voltage is applied.
  • Electronic devices usually comprise a cathode, an anode and at least one functional, preferably emissive, layer. In addition to these layers, they can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge generation layers. .
  • the object of the present invention is to provide compounds which are suitable for use in an electronic device, in particular an OLED, in particular as material for hole-transport layers or material for electron-transport layers, and lead to good properties there.
  • the present invention relates to a compound of the formula (1),
  • X is the same or different on each occurrence of CR or N with the proviso that a maximum of two groups of X per cycle are N;
  • R is the same or different on each occurrence and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which can each be substituted by one or more R 1 radicals;
  • Ar' is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which can be substituted by one or more R 1 radicals, where two or more R 1 groups can form an aromatic or heteroaromatic ring system together;
  • R 2 is the same or different on each occurrence and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more H atoms can also be replaced by D or F; two or more substituents R 2 can be linked to one another and form a ring.
  • An aryl group within the meaning of this invention contains 6 to 40 carbon atoms; a heteroaryl group within the meaning of this invention contains 5 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aryl group or heteroaryl group is either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or one 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 aryl or heteroaryl groups, but as aromatic ring systems.
  • An aromatic ring system within the meaning of this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms in the ring system.
  • a heteroaromatic ring system within the meaning of this invention contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system which does not necessarily only contain aryl or heteroaryl groups, but also in which several aryl or heteroaryl groups a non-aromatic moiety (preferably less than 10% of the non-H atoms), such as e.g. B. a C, N or O atom or carbonyl group can be connected.
  • aryl or heteroaryl groups preferably less than 10% of the non-H atoms
  • two or more aryl or heteroaryl groups are linked directly to each other, such as. B. biphenyl, terphenyl, bipyridine or phenylpyridine.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. should also be understood as aromatic ring systems for the purposes of this invention, and also systems in which two or more aryl groups, for example are linked by a linear or cyclic alkyl group or by a Si ly I group.
  • Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups and groups in which two or more aryl or heteroaryl groups are linked directly to one another, for example biphenyl, terphenyl, quaterphenyl or bipyridine, and also fluorene or spirobifluorene.
  • An electron-rich heteroaromatic ring system is characterized in that it is a heteroaromatic ring system that does not contain any electron-deficient heteroaryl groups.
  • An electron-deficient heteroaryl group is a six-membered-membered heteroaryl group containing at least one nitrogen atom or a five-membered-membered heteroaryl group containing at least two heteroatoms, one of which is a nitrogen atom and the other is oxygen, sulfur or a substituted nitrogen atom, further aryl or heteroaryl groups being attached to each of these groups can be condensed.
  • electron-rich heteroaryl groups are five-membered-membered heteroaryl groups with exactly one heteroatom selected from oxygen, sulfur or substituted nitrogen, to which further aryl groups and/or further electron-rich five-membered-membered heteroaryl groups can be fused.
  • electron-rich heteroaryl groups are pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene or indenocarbazole.
  • An electron-rich heteroaryl group is also referred to as an electron-rich heteroaromatic radical.
  • An electron-deficient heteroaromatic ring system is characterized as containing at least one electron-deficient heteroaryl group, and more preferably no electron-rich heteroaryl groups.
  • alkyl group is used as a generic term both for linear or branched alkyl groups and for cyclic alkyl groups.
  • alkenyl group and alkynyl group are used as generic terms both for linear or branched alkenyl or alkynyl groups and for cyclic alkenyl or alkynyl groups.
  • a cyclic alkyl, alkoxy or thioalkoxy group in the context of this invention is understood as meaning a monocyclic, a bicyclic or a polycyclic group.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 40 carbon atoms, and in which individual H atoms or CH 2 groups are also substituted by the abovementioned groups can be, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-
  • An alkoxy group OR 1 having 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
  • a thioalkyl group SR 1 having 1 to 40 carbon atoms is, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopenten
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, it being possible for one or more non-adjacent CH2 groups to be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO2, preferably F, Cl or CN, particularly preferably F or CN.
  • aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, preferably 5 - 40 aromatic ring atoms, which can be substituted in each case with the above-mentioned radicals or a hydrocarbon radical and which can be linked via any positions on the aromatic or heteroaromatic, in particular Understood groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis - or trans-indenofluorene, cis- or trans-indenocarbazole, cis-
  • the above formulation should also be understood to mean that if one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring. This should be illustrated by the following scheme:
  • Ar 1 is identical or different on each occurrence, a bivalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 1 ;
  • X is CR
  • all Xs are CR, where R is
  • Preferred embodiments of the compounds of the formulas (2), (3) and (4) are the following compounds of the formulas (2-1) to (4-1):
  • the compounds of formulas (2) and (3) or their preferred embodiments may form a pair of enantiomers depending on the substitution.
  • the compound according to the invention is preferably present as a racemate, but it can also be present as a pure enantiomer.
  • R, Ar 1 , Ar', R', R", R 1 and R 2 are described below.
  • the preferences given below for R, Ar 1 , Ar′, R′, R′′, R 1 and R 2 occur simultaneously and apply to the structures of the formula (1) and to all preferred ones listed above embodiments.
  • R is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, OR 1 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon Atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, in which case the alkyl or alkenyl group can be substituted by one or more radicals R 1 , but is preferably unsubstituted, and in which one or more non-adjacent CH 2 groups can be replaced by 0 , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 ; two radicals R can also form an aliphatic, aromatic or heteroaromatic ring system with one another.
  • R is particularly preferably selected identically or differently on each occurrence from the group consisting of H, F, CN, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where each alkyl group may be substituted by one or more radicals R 1 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 , can be substituted.
  • R is very particularly preferably selected on each occurrence, identically or differently, from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which can be substituted by one or more radicals R 2 , preferably non-aromatic radicals R 2 .
  • Suitable aromatic or heteroaromatic ring systems R are selected from phenyl, 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, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, 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, indolocarbazole
  • the groups R are preferably selected from the groups of the following formulas R-1 to R-163,
  • Ar 3 is identical or different on each occurrence, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which can be substituted by one or more radicals R 1 ;
  • a 1 is identical or different on each occurrence, BR 1 , C(R 1 ) 2 , NR 1 , O or S, preferably C(R 1 ) 2 , NR 1 , O or S;
  • Ar 3 comprises divalent aromatic or heteroaromatic ring systems based on the groups of R-1 to R-163, where p is 0 and the dashed bond and an R 1 is the bond to the aromatic or heteroaromatic group is after R-1 to R-163.
  • the substituent R 1 which is bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more R 2 radicals.
  • this substituent R 1 is identical or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, which has no fused aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are fused directly to one another, and which can each also be substituted by one or more R 2 radicals.
  • phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35 it being possible for these structures to be substituted by one or more radicals R 1 , but they are preferably unsubstituted.
  • a 1 is C(R 1 ) 2
  • the substituents R 1 bonded to this carbon atom are preferably identical or different on each occurrence for a linear alkyl group having 1 to 10 carbon atoms or for a branched or cyclic alkyl group with 3 to 10 carbon atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 .
  • R 1 very particularly preferably represents a methyl group or a phenyl group.
  • the radicals R 1 can also form a ring system with one another, which leads to a spiro system.
  • Suitable aromatic or heteroaromatic ring systems R" are selected from phenyl, 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, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which can be linked via the 1-, 2-, 3- or 4-position can be linked, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazol
  • the groups R" represent an aromatic or heteroaromatic ring system, they are preferably selected from the groups of the formulas R-1 to R-163, preferably R-1 to R-26, R-36 to R-38, R-44 to R-69.
  • R' is selected identically or differently on each occurrence from the group consisting of D, F, CN, OR 1 , an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which is replaced by one or more radicals R 1 may be substituted, provided that at least when two R' are present, one or both R' comprise at least one triazine group substituted with two R'' groups.
  • R' is particularly preferably selected identically or differently on each occurrence from the group consisting of D, F, CN or an aromatic tic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 , preferably non-aromatic radicals R 2 , with the proviso that at least when two R 'are present, one or both R 'Include at least one triazine group which is substituted with two radicals R'.
  • Suitable aromatic or heteroaromatic ring systems R' are selected from phenyl, 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, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which can be linked via the 1-, 2-, 3- or 4-position can be linked, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazol
  • the groups R′ if they represent an aromatic or heteroaromatic ring system, are preferably selected from the groups of the following formulas R-1 to R-163, where if two groups R′ are present, at least one represents R-79 .
  • R 1 is identical or different on each occurrence selected from the group consisting of H, D, F, CN, OR 2 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, the alkyl or alkenyl group each having one or more radicals R 2 may be substituted and where one or more non-adjacent CH2 groups may be replaced by 0, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals; two or more radicals R 1 can form an aliphatic ring system with one another.
  • R 1 is identical or different on each occurrence selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or one branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group may be substituted by one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more R 2 radicals may be substituted, but is preferably unsubstituted.
  • R 2 is the same or different on each occurrence of H, F, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms which is linked to an alkyl group having 1 to 4 carbon atoms. Atoms may be substituted, but is preferably unsubstituted.
  • all radicals R 1 if they represent an aromatic or heteroaromatic ring system, or R 2 if they represent aromatic or heteroaromatic groups, are selected from the groups R-1 to R-163, which, however, then are each substituted accordingly with R 2 or the groups mentioned for R 2 .
  • radicals R do not form any further aromatic or heteroaromatic groups fused onto the basic structure of the formula (1).
  • R on each occurrence is identical or different for H, D, F, CN or a group selected from the groups R-1 to R-163, with the proviso that p is 0 and R 1 represents H, D, F or CN for these groups, the groups R-1 to R-48, R-114 to R-120 being preferred.
  • R is the same or different on each occurrence on all cycles of the compound of formula (1) for H, D, F or CN, preferably H, except on the cycle to which the triazine group is attached.
  • R′′ is the same or different on each occurrence for a group R-1 to R-163, where R 1 is H, D, F or CN for these groups.
  • R'' and R' on each occurrence represent a group R-1 to R-163, where R 1 represents H, D, F or CN for these groups.
  • At least one Ar 1 , R'' and/or R' comprises more than 6 aromatic ring atoms.
  • At least one Ar 1 , R" and/or R' is selected from one of the groups R-44 to R-78, R-112, R-113, R-143, R-146, R-153 to R-163 with the proviso that p is 0, and in the case of Ar 1 there is a divalent group in which an R 1 represents the further bond to the triazine.
  • 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 that are processed from solution are also compounds that are substituted with alkyl groups, especially branched alkyl groups, having up to 10 carbon atoms or with oligoarylene groups, such as ortho-, meta-, para- or branched terphenyl or quaterphenyl groups are substituted.
  • alkyl groups especially branched alkyl groups, having up to 10 carbon atoms or with oligoarylene groups, such as ortho-, meta-, para- or branched terphenyl or quaterphenyl groups are substituted.
  • the preferred embodiments mentioned above can be combined with one another at will within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously.
  • the compounds according to the invention can be prepared by synthesis steps known to those skilled in the art, such as, for. B. bromination, Suzuki coupling, Ullmann coupling, Heck reaction, Hartwig-Buchwald coupling, etc., are shown.
  • a further subject of the present invention is therefore a process for the preparation of the compounds according to the invention, characterized by the following steps: (A) Synthesis of the basic structure according to formula (1);
  • the cyanation can also take place starting from the triflate.
  • Trz triazine
  • Suzuki coupling with an aryl/heteroaryl boronic acid or ester ((HO)2B-Ar), followed by a ruthenium-catalyzed triflate bromide Exchange, palladium-catalyzed borylation of the bromide, and final Suzuki coupling with a chlorotriazine: being represented.
  • Formulations of the compounds according to the invention are required for the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) - fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4 -dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decal
  • a further subject matter of the present invention is therefore a formulation, in particular a solution, dispersion or emulsion, comprising at least one compound according to the invention and at least one further compound.
  • the further compound can be a solvent, for example, in particular one of the abovementioned solvents or a mixture of these solvents.
  • the preparation of such solutions is known to the person skilled in the art and is described, for example, in WO 2002/072714, WO 2003/019694 and the literature cited therein.
  • the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and/or a matrix material. This further connection can also be polymeric.
  • the compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device (OLED). Depending on the substitution, the compounds can be used in different functions and layers.
  • OLED organic electroluminescent device
  • a further subject matter of the present invention is therefore the use of a connection according to the invention in an electronic device.
  • Yet another subject matter of the present invention is an electronic device containing at least one connection according to the invention.
  • the compounds according to the invention can be present as a racemate or as a pure enantiomer, in particular when they are used.
  • An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or also layers which are made up entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O -laser) and organic plasmon emitting devices, but preferably organic electroluminescent devices (OLEDs).
  • O-ICs organic integrated circuits
  • O-FETs organic field effect transistors
  • OF-TFTs organic thin-film transistors
  • O-LETs organic light-emitting transistors
  • O-SCs organic solar cells
  • DSSCs dye-sensitized organic solar cells
  • organic optical detectors organic photore
  • the device is particularly preferably an organic electroluminescent device comprising cathode, anode and at least one emitting layer, wherein at least one organic layer, which can be an emitting layer, hole transport layer, electron transport layer, hole blocking layer, electron blocking layer or another functional layer, comprises at least one compound according to the invention.
  • the layer depends on the substitution of the compound.
  • the organic electroluminescent device can 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, charge generation layers (charge generation layers) and/or organic or inorganic p/n transitions.
  • interlayers can be introduced between two emitting layers, which, for example, have an exciton-blocking function.
  • each of these layers does not necessarily have to be present.
  • the organic electroluminescence device can contain an emitting layer, or it can contain a plurality of emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in white emission overall, i. H. in the emitting layers different emitting compounds are used which can fluoresce or phosphoresce. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green and orange or red emission (the basic structure is described, for example, in WO 2005/011013).
  • the organic electroluminescence device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.
  • the compound of the formula (1) is preferably used in an organic electroluminescent device which comprises one or more phosphorescent emitters.
  • the connection according to the invention according to the embodiments listed above can be used in different layers, depending on the exact structure.
  • the organic electroluminescence device can contain an emitting layer or it can contain a plurality of emitting layers, with at least one layer containing at least one compound according to the invention. Furthermore, the compound 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.
  • phosphorescent compound typically refers to compounds where the emission of light occurs through a spin-forbidden transition, e.g. B. a transition from a excited triplet state or a state with a higher spin quantum number, e.g. B. a quintet state.
  • Suitable phosphorescent compounds are, in particular, compounds which, when suitably excited, emit light, preferably in the visible range, and also at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 included. All luminescent complexes with transition metals or lanthanides are considered to be preferred as phosphorescent compounds, particularly if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold or europium, particularly compounds containing indium, contain platinum or copper. In the context of the present invention, all luminescent indium, platinum or copper complexes are considered to be phosphorescent emitting compounds.
  • Examples of the emitters described above can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/ 0258742 WO 2009/146770 WO 2010/015307 WO 2010/031485 WO 2010/054731 WO 2010/054728 WO 2010/086089 WO 2010/099852 WO 2010/102709 WO 2010/099852 066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/104045, WO 2015/12018/12015/ 015815, WO 2016/124304, WO 2017/032439, WO 2018/011186, WO
  • all phosphorescent complexes are suitable as are used according to the prior art for phosphorescent OLEDs and as are known to the person skilled in the field of organic electroluminescence, and the person skilled in the art can use further phosphorescent complexes without any inventive step. It is also possible for the person skilled in the art, without any inventive activity, to produce further phosphorescent complexes in combination with the compounds of the formula (1) in organic form to use electroluminescent devices. Further examples are listed in a table below.
  • the compound of formula (1) in an electronic device which contains one or more fluorescent emitting compounds.
  • the compounds of the formula (1) are used as hole-transporting material.
  • the compounds are preferably contained in a hole transport layer, an electron blocking layer or a hole injection layer. Use in an electron blocking layer is particularly preferred.
  • a hole-transporting layer within the meaning of the present application is a layer with a hole-transporting function between the anode and the emitting layer.
  • hole-injection layers and electron-blocking layers are understood as meaning specific embodiments of hole-transport layers.
  • a hole-injection layer is a hole-transport layer which is directly adjacent to the anode or is only separated from the anode by a single coating.
  • an electron blocking layer is that hole transport layer which is directly adjacent to the emitting layer on the anode side.
  • the OLED according to the invention preferably comprises two, three or four hole-transporting layers between the anode and the emitting layer, of which preferably at least one, particularly preferably precisely one or two, contain a compound of the formula (1).
  • the compound of formula (1) as Lochtransportmatenal in a hole-transport layer, a hole-injection layer or a Electron blocking layer used, the compound can be used as pure material, ie in a proportion of 100%, in the hole transport layer, or it can be used in combination with one or more other compounds.
  • the organic layer which contains the compound of the formula (1) then additionally contains one or more p-type dopants.
  • P-type dopants used in accordance with the present invention are preferably those organic electron acceptor compounds capable of oxidizing one or more of the other compounds in the mixture.
  • p-dopants are those in WO 2011/073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO 2009/003417, WO 2009/003455 2011/120709, US 2010/0096600, WO 2012/095143 and DE 102012209523.
  • Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenylenes, azatriphenylenes, h, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni , Pd, and Pt with ligands containing at least one oxygen atom as a binding site.
  • Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2O?, MoOs, WO3 and ReOs.
  • the p-type dopants are preferably present in a substantially homogeneous distribution in the p-type layers. This can e.g. B. be achieved by co-evaporation of the p-dopant and the hole transport material matrix.
  • Preferred p-dopants are in particular the following compounds:
  • the compound of the formula (1) is used as a hole-transport material in combination with a hexaazatriphenylene derivative, as described in US 2007/0092755.
  • the hexaazatriphenylene derivative is particularly preferably used here in a separate layer.
  • the compound of the formula (1) is used in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent compounds.
  • the proportion of the matrix material in the emitting layer is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume, particularly preferably between 92.0 and 99.5% by volume -%. for fluorescent emitting layers and between 85.0 and 97.0% by volume for phosphorescent emitting layers.
  • the proportion of the emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume, particularly preferably between 0.5 and 8.0% by volume for fluorescent ones emissive layers and between 3.0 and 15.0% by volume. for phosphorescent emitting layers.
  • An emitting layer of an organic electroluminescent device can also comprise systems that contain a multiplicity of matrix materials (mixed matrix systems) and/or a multiplicity of emitting compounds.
  • the emitting compounds are usually those that have the smaller proportion in the system and the matrix materials are those that have the larger proportion in the system.
  • the proportion of a single matrix material in the system can be lower than the proportion of a single emitting compound.
  • the compounds of the formula (1) are preferably used as a component of mixed matrix systems.
  • the mixed matrix systems exist preferably from two or three different matrix materials, particularly preferably from two different matrix materials.
  • one of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties.
  • the compound of formula (1) is preferably the matrix material with hole-transporting properties.
  • the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely combined in a single mixed matrix component, with the further mixed matrix component(s) fulfilling other functions.
  • the two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1 and most preferably 1:4 to 1:1.
  • Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. A source for more detailed information on mixed matrix systems is the application WO 2010/108579.
  • the mixed matrix systems can contain one or more emissive compounds, preferably one or more phosphorescent compounds.
  • mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices.
  • Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent compounds mentioned below or the preferred matrix materials for fluorescent compounds, depending on which type of emitting compound is used in the mixed matrix system becomes.
  • Preferred phosphorescent compounds for use in mixed matrix systems are the same as described above generally preferred phosphorescent emitter materials described.
  • Examples of phosphorescent compounds are listed below.
  • Preferred fluorescent emitting compounds are selected from the class of arylamines.
  • an arylamine or an aromatic amine is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems which are bonded directly to the nitrogen.
  • at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms.
  • Preferred examples of these are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
  • An aromatic anthracenamine is understood as meaning a compound in which a diarylamino group is attached directly to an anthracene group, preferably in the 9-position.
  • An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9, 10-positions or 1, 6-position are attached to the pyrene.
  • Further preferred emitting compounds are indenofluorenamines or fluorenediamines, for example according to WO 2006/108497 or WO 2006/122630, benzoindenofluorenamines or -fluorenediamines, for example according to WO 2008/006449, and dibenzoindenofluorenamines or -diamines, for example according to WO 2007/140847, and those in WO 2010/012328 disclosed indenofluorene derivatives with fused aryl groups.
  • the pyrenearylamines disclosed in WO 2012/048780 and in WO 2013/185871 are also preferred.
  • benzoindenofluoreneamines disclosed in WO 2014/037077 are also preferred.
  • benzofluoreneamines disclosed in WO 2014/106522 are also preferred.
  • the extended benzoindenofluorenes disclosed in WO 2014/111269 and in WO 2017/036574 are also preferred.
  • the extended benzoindenofluorenes disclosed in WO 2017/028940 and in WO 2017/028941 Phenoxazines and the fluorine derivatives bonded to furan units or to thiophene units disclosed in WO 2016/150544.
  • boron compounds according to WO2020208051, WO2015102118, WO2016152418, WO2018095397, WO2019004248, WO2019132040, US20200161552, WO2021089450 can be used.
  • Useful matrix materials include materials from different classes of substances.
  • Preferred matrix materials are selected from the classes of oligoaryls (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoaryls with fused aromatic groups, the oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461) , the polypodal metal complexes (e.g. according to WO 2004/081017), the hole-conducting compounds (e.g.
  • the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides etc. (e.g. according to WO 2005/084081 and WO 2005/084082 ), the atropisomers (for example according to WO 2006/048268), the boronic acid derivatives (for example according to WO 2006/117052) or the benzanthracenes (for example according to WO 2008/145239).
  • Particularly preferred matrix materials are selected from the classes of oligoarylenes with naphthalene, anthracene, benzanthracene and/or pyrene or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides and sulfoxides.
  • Very particularly preferred matrix materials are selected from the classes of oligoarylenes, which include anthracene, benzanthracene, benzophenanthrene and/or pyrene or atropisomers of these compounds.
  • an oligoarylene is a compound in which at least three aryl or arylene groups are connected to one another.
  • anracthene derivatives disclosed in WO 2006/097208, WO 2006/131192, WO 2007/065550, WO 2007/110129, WO 2007/065678, WO 2008/145239, WO 2009/100925, WO 2011/054442 and EP 1553154 the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012/0187826, the benzanthracenylanthracene compounds disclosed in WO 2015/158409, the indenobenzofurans disclosed in WO 2017/025165 and the phenanthrylanthracenes disclosed in WO 2017/036573.
  • Preferred matrix materials for phosphorescent compounds are, as are compounds of the formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B. CBP (N, N-bis carbazolylbiphenyl) or WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, z. B.
  • CBP N, N-bis carbazolylbiphenyl
  • WO 2005/039246 US 2005/0069729, JP 2004/288381
  • WO 2012/048781 lactams, z. B. according to WO 2011/116865 or WO 2011/137951, or dibenzofuran derivatives, z. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010/108579.
  • Suitable charge transport materials can be used in the hole injection or hole transport layer or in the electron blocking layer or in the electron transport layer of the electronic component according to the invention, in addition to the compounds of formula (1), for example those in Y. Shirota et al., Chem. Rev. 2007 , 107(4), 953-1010, or other materials used in these prior art layers.
  • the OLED according to the invention preferably comprises two or more different hole-transporting layers.
  • the compound of the formula (1) can be used in one or more or in all of the hole-transporting layers.
  • the compound of the formula (1) is used in exactly one or exactly two hole-transporting layers, and other compounds, preferably aromatic amine compounds, are used in the other hole-transporting layers present.
  • Further compounds which, in addition to the compounds of the formula (1), are preferably used in hole-transporting layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (for example according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene Derivatives (e.g.
  • WO 01/049806 amine derivatives with fused aromatics
  • WO 95/09147 monobenzoindenofluorenamines (for example according to WO 08/006449), dibenzoindenofluorenamines (for example according to WO 07/140847), spirobifluorenamines (for example according to WO 2012 /034627 or WO 2013/120577), fluorenamines (for example according to WO 2014/015937, WO 2014/015938, WO 2014/015935 and WO 2015/082056), spirodibenzopyranamines (for example according to WO 2013/083216), dihydroacridine derivatives (for example according to WO 2012/150001), spirodibenzofurans and spirodibenzothiophenes (for example according to WO 2015/022051, WO 2016/102048 and WO 2016/
  • spirobifluorenes substituted by diarylamino groups in the 4-position as hole-transporting compounds is very particularly preferred, in particular the use of those compounds which are claimed and disclosed in WO 2013/120577 and the use of spirobifluorenes substituted by diarylamino groups in the 2-position as hole-transporting compounds Compounds, in particular the use of those compounds claimed and disclosed in WO 2012/034627.
  • Aluminum complexes e.g. Alq3, zirconium complexes, e.g. Zrq4, lithium complexes, e.g. Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives are particularly suitable.
  • Preferred cathodes of the electronic component are metals with a low work function, metal alloys or multilayer structures made of different metals, e.g. B. alkaline earth metals, alkali metals, main group metals or lanthanides (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys of an alkali or alkaline earth metal and silver, e.g. B. an alloy of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function can also be used, e.g. B. Ag or Al, usually combinations of metals such. B.
  • Ca / Ag, Mg / Ag or Ba / Ag can be used. It can also be advantageous to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.
  • suitable materials are alkali or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, Li2O, BaF2, MgO, NaF, CsF, CS2CO3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose.
  • the layer thickness of this layer is preferably between 0.5 and 5 nm.
  • Preferred anodes are high work function materials.
  • the anode has a work function greater than 4.5 eV versus vacuum.
  • metals with a high redox potential e.g. B. Ag, Pt or Au.
  • metal/metal oxide electrodes e.g. Al/Ni/NiOx, Al/PtOx
  • at least one of the electrodes must be transparent or partially transparent in order to allow the irradiation of the organic material (organic solar cell) or the emission of light (OLED, O-laser).
  • Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred.
  • the anode can also consist of two or more layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • the device is structured, contacted and finally sealed accordingly (depending on the application) in order to exclude harmful influences from water and air.
  • an organic electroluminescence device characterized in that one or more layers are coated using a sublimation process.
  • the materials are vapour-deposited in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10-7 mbar.
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated using the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure of between 10'5 mbar and 1 bar.
  • 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 (ink jet 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 (ink jet printing) or nozzle printing.
  • Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.
  • the electronic devices containing one or more compounds of the formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications (e.g. light therapy).
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished by one or more of the following properties:
  • the compounds according to the invention lead to high efficiencies, in particular to a high EQE.
  • the following syntheses are carried out under a protective gas atmosphere in dried solvents.
  • the metal complexes are also handled with the exclusion of light or under yellow light.
  • the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds relate to the CAS numbers of the compounds known from the literature. For compounds that may have multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as representative.
  • the glass beads are decanted off, the NMP is removed in vacuo, the residue is taken up in 500 ml of ethyl acetate (EA), washed twice with 300 ml of water each time, once with 200 ml of sat. saline and dried over magnesium sulfate.
  • EA ethyl acetate
  • the desiccant is filtered off over a silica gel bed preslurried with EE, the filtrate is concentrated to dryness, the residue is stirred with 200 ml of hot methanol, the product is filtered off with suction, washed with a little methanol and dried in vacuo. Yield: 36.9 g (90 mmol) 90%; Purity: approx. 97% according to 1 H-NMR.
  • a well-stirred mixture of 64.1 g (100 mmol) S302, 26.9 g (300 mmol) copper(I) cyanide, 100 g glass beads (3 mm diameter) and 400 ml NMP is stirred at 170° C. for 24 h. It is filtered while still hot over a silica gel bed pre-slurried with NMP and the filtrate is stirred into 1000 ml of 10% strength by weight aqueous ammonia solution. The precipitated crude product is filtered off with suction, washed three times with 100 ml of 10% strength by weight aqueous ammonia solution, twice with 100 ml of water and twice with 50 ml of methanol and dried in vacuo.
  • the mixture is allowed to cool and is decanted from the glass beads, most of the DMSO is removed in vacuo, the residue is treated with 300 ml of methanol and 200 ml of water, the crude product is filtered off with suction, washed twice with 200 ml of methanol each time and dried in vacuo.
  • the crude product is taken up in 300 ml DCM, filtered through a bed of silica gel pre-slurried with DCM, the filtrate is evaporated to dryness, the residue is stirred hot with 200 ml methanol, the crude product is filtered off and washed twice with 50 ml each time methanol and dried in vacuo.
  • the bromides S200-S306 can be used
  • Variant A via Grignard connection From a mixture of 40.9 g (100 mmol) S200, 7.9 mL (100 mmol)
  • a Grignard reagent is prepared with 4.9 g (200 mmol) of magnesium from 1,2-dichloroethane and 500 ml of THF. After the magnesium has been completely consumed, it is allowed to cool to room temperature and a solution of 28.1 g (105 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine [3842-55-5] is added dropwise with ice cooling 300 ml THF to.
  • the salts are filtered off while still warm through a bed of Celite pre-slurried with dioxane, the filtrate is concentrated to dryness, the boron ester is stirred out twice with 200 ml of hot methanol each time, filtered off and dried in vacuo.
  • the desiccant is filtered off over a silica gel bed pre-slurried with toluene, the filtrate is concentrated to dryness, the residue is stirred with 200 ml of hot methanol, filtered off and dried in vacuo.
  • OLEDs according to the invention and OLEDs according to the prior art are produced using a general method according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the compounds T according to the invention can be used in the electron transport layer (ETL) and the hole blocking layer (HBL). All materials are thermally evaporated in a vacuum chamber.
  • the emission layer (EML) always consists of at least one matrix material (host material, host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is added to the matrix material or matrix materials by co-evaporation in a certain volume fraction is added.
  • a specification such as SMB:D (97:3%) means that the material SMB is present in the layer in a volume proportion of 97% and the dopant D in a proportion of 3%.
  • the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) are calculated as a function of the luminance determined from current-voltage-luminance characteristics (IIIL characteristics) assuming a Lambertian emission characteristic and the service life.
  • the EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd/m 2
  • the service life is determined at an initial luminance of 10000 cd/m 2 .
  • the LT80 in (h) is the measured time in which the brightness has fallen to 80% of the initial brightness.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • Emission layer see Table 1
  • HBL Hole Blocker Layer
  • Electron transport layer see Table 1
  • the compounds T according to the invention can be used in the electron transport layer (ETL), the hole blocking layer (HBL) and in the emission layer (EML) as matrix material (host material, host material) M (see Table 5) or T (see materials according to the invention).
  • matrix material host material, host material
  • EML emission layer
  • all materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is admixed to the matrix material or matrix materials by co-evaporation in a certain proportion by volume.
  • a specification such as M1 :M2:lr (55%:35%:10%) means that the material M1 accounts for 55% by volume, M2 for 35% by volume and Ir for 10% by volume in the layer present.
  • the electron transport layer can also consist of a mixture of two materials. The precise structure of the OLEDs can be found in Table 3. The materials used to fabricate the OLEDs are shown in Table 5.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance are calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic and the service life.
  • the specification of the EQE in (%) and the voltage in (V) takes place at a luminance of 1000 cd/m 2
  • the service life is at an initial luminance of 1000 cd/m 2 for blue and red, 10000 cd/m 2 for green and yellow emitting components.
  • the specification LT80 in (h) is the measured time in which the brightness falls to 80% of the initial brightness.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer from HTM1, 180 nm for blue, 50 nm for green, 40 nm for yellow, 90 nm for red
  • Electron blocking layer (EBL) 20nm of EBM2 for blue, 20nm of EBM1 for green and yellow, 10nm for red
  • Emission layer see Table 3
  • HBL Hole Blocker Layer
  • Electron transport layer see Table 3

Abstract

La présente invention concerne des composés qui sont appropriés pour être utilisés dans des dispositifs électroniques, et des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant lesdits composés.
PCT/EP2022/076741 2021-09-28 2022-09-27 Matériaux pour dispositifs électroniques WO2023052314A1 (fr)

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Citations (167)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
WO1995009147A1 (fr) 1993-09-29 1995-04-06 Idemitsu Kosan Co., Ltd. Element electroluminescent organique et derive d'arylenediamine
EP0652273A1 (fr) 1993-11-09 1995-05-10 Shinko Electric Industries Co. Ltd. Matériau organique pour dispositif électroluminescent et dispositif électroluminescent
EP0676461A2 (fr) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Composés spiro et leur application comme matières électroluminescentes
JP2000053957A (ja) 1998-06-23 2000-02-22 Koto Gijutsu Kenkyuin Kenkyu Kumiai 新規な有機金属発光物質およびそれを含む有機電気発光素子
WO2000070655A2 (fr) 1999-05-13 2000-11-23 The Trustees Of Princeton University Dispositifs electroluminescents organiques a tres haute performance utilisant l'electrophosphorescence
WO2001041512A1 (fr) 1999-12-01 2001-06-07 The Trustees Of Princeton University Complexes de forme l2mx en tant que dopants phosphorescents pour del organiques
WO2001049806A1 (fr) 1999-12-31 2001-07-12 Lg Chemical Co., Ltd Dispositif electronique comprenant un compose organique presentant les caracteristiques de semi-conduction du dopage p
WO2002002714A2 (fr) 2000-06-30 2002-01-10 E.I. Du Pont De Nemours And Company Composes d'iridium electroluminescents contenant des phenylpyridines fluores, des phenylpyrimidines et des phenylquinolines, et dispositifs fabriques avec ces composes
WO2002015645A1 (fr) 2000-08-11 2002-02-21 The Trustees Of Princeton University Composes organometalliques et electrophosphorescence organique presentant un deplacement d'emission
EP1191612A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent, dispositif d'affichage et composé complexe d'un métal
EP1191614A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent et composé complexe d'un métal utilisé pour ce dispositif
EP1191613A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent, dispositif d'affichage et composé complexe d'un métal
EP1205527A1 (fr) 2000-03-27 2002-05-15 Idemitsu Kosan Co., Ltd. Dispositif a electroluminescence organique
WO2002072714A1 (fr) 2001-03-10 2002-09-19 Covion Organic Semiconductors Gmbh Solutions et dispersions de semi-conducteurs organiques
WO2003019694A2 (fr) 2001-08-24 2003-03-06 Covion Organic Semiconductors Gmbh Solutions de semi-conducteurs polymeres
WO2003060956A2 (fr) 2002-01-18 2003-07-24 Lg Chem, Ltd. Nouveau materiau permettant de transporter des electrons et affichage organique electroluminescent utilisant ledit materiau
WO2004013080A1 (fr) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Derives de spirobifluorene, leur preparation et leurs utilisations
WO2004028217A1 (fr) 2002-09-20 2004-04-01 Idemitsu Kosan Co., Ltd. Element organique electroluminescent
WO2004058911A2 (fr) 2002-12-23 2004-07-15 Covion Organic Semiconductors Gmbh Element electroluminescent organique
WO2004080975A1 (fr) 2003-03-13 2004-09-23 Idemitsu Kosan Co., Ltd. Derive heterocyclique contenant de l'azote et element electroluminescent organique utilisant ce derive
WO2004081017A1 (fr) 2003-03-11 2004-09-23 Covion Organic Semiconductors Gmbh Complexes metalliques
JP2004288381A (ja) 2003-03-19 2004-10-14 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子
WO2004093207A2 (fr) 2003-04-15 2004-10-28 Covion Organic Semiconductors Gmbh Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges
WO2005011013A1 (fr) 2003-07-21 2005-02-03 Covion Organic Semiconductors Gmbh Element electroluminescent organique
WO2005019373A2 (fr) 2003-08-19 2005-03-03 Basf Aktiengesellschaft Complexes de metal de transition comportant des ligands de carbene faisant office d'emetteurs pour diodes electroluminescentes organiques (delo)
US20050069729A1 (en) 2003-09-30 2005-03-31 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
WO2005033244A1 (fr) 2003-09-29 2005-04-14 Covion Organic Semiconductors Gmbh Complexes metalliques
EP1553154A1 (fr) 2002-08-23 2005-07-13 Idemitsu Kosan Co., Ltd. Dispositif organique electroluminescent et derive d'anthracene
WO2005084082A1 (fr) 2004-02-20 2005-09-09 Merck Patent Gmbh Dispositifs electroniques organiques
US20050258742A1 (en) 2004-05-18 2005-11-24 Yui-Yi Tsai Carbene containing metal complexes as OLEDs
WO2005111172A2 (fr) 2004-05-11 2005-11-24 Merck Patent Gmbh Nouveaux melanges de materiaux pour applications electroluminescentes
JP2005347160A (ja) 2004-06-04 2005-12-15 Konica Minolta Holdings Inc 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
EP1617710A1 (fr) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Materiau pour dispositif electroluminescent organique, dispositif electroluminescent organique, dispositif d'eclairage et affichage
WO2006005627A1 (fr) 2004-07-15 2006-01-19 Merck Patent Gmbh Derives oligomeres de spirobifluorene, leur elaboration et leur utilisation
WO2006048268A1 (fr) 2004-11-06 2006-05-11 Merck Patent Gmbh Dispositif electroluminescent organique
EP1661888A1 (fr) 2004-11-29 2006-05-31 Samsung SDI Co., Ltd. Composé contenant un phenylcarbazole et dispositif organiques électroluminiscent l'utilisant
WO2006097208A1 (fr) 2005-03-16 2006-09-21 Merck Patent Gmbh Nouveaux materiaux pour des dispositifs electroluminescents organiques
WO2006100896A1 (fr) 2005-03-18 2006-09-28 Idemitsu Kosan Co., Ltd. Derive d’amine aromatique et dispositif electroluminescent organique l’utilisant
WO2006108497A1 (fr) 2005-04-14 2006-10-19 Merck Patent Gmbh Composes pour dispositifs electroniques organiques
WO2006117052A1 (fr) 2005-05-03 2006-11-09 Merck Patent Gmbh Dispositif electroluminescent organique, et derives d'acide boronique et d'acide borinique utilises pour produire ce dispositif electroluminescent organique
EP1722602A1 (fr) 2004-03-05 2006-11-15 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique et affichage electroluminescent organique
WO2006122630A1 (fr) 2005-05-20 2006-11-23 Merck Patent Gmbh Composes pour dispositifs electroniques organiques
EP1731584A1 (fr) 2004-03-31 2006-12-13 Konica Minolta Holdings, Inc. Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, écran et dispositif d'éclairage
WO2006131192A1 (fr) 2005-06-09 2006-12-14 Merck Patent Gmbh Nouveaux materiaux destines a des dispositifs electroluminescents organiques
EP1749809A1 (fr) 2004-05-27 2007-02-07 Idemitsu Kosan Co., Ltd. Derive de pyrene asymetrique et dispositif electroluminescent organique utilisant celui-ci
US20070092755A1 (en) 2005-10-26 2007-04-26 Eastman Kodak Company Organic element for low voltage electroluminescent devices
WO2007063754A1 (fr) 2005-12-01 2007-06-07 Nippon Steel Chemical Co., Ltd. Compose pour element electroluminescent organique et element electroluminescent organique
WO2007065550A1 (fr) 2005-12-08 2007-06-14 Merck Patent Gmbh Nouvelles matières pour dispositifs électroluminescents organiques
WO2007065678A1 (fr) 2005-12-08 2007-06-14 Merck Patent Gmbh Nouvelles matieres pour dispositifs electroluminescents organiques
WO2007110129A1 (fr) 2006-03-24 2007-10-04 Merck Patent Gmbh Nouveaux materiaux pour disposifs electroluminescents organiques
WO2007137725A1 (fr) 2006-05-31 2007-12-06 Merck Patent Gmbh Nouveaux matériaux pour dispositifs électroluminescents organiques
WO2007140847A1 (fr) 2006-06-02 2007-12-13 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2008006449A1 (fr) 2006-07-11 2008-01-17 Merck Patent Gmbh Nouveaux matériaux destinés à des dispositifs électroluminescents organiques
EP1905754A1 (fr) 2005-07-06 2008-04-02 Idemitsu Kosan Co., Ltd. Dérivé du pyrène et dispositif électroluminescent organique l utilisant
WO2008056746A1 (fr) 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique
WO2008086851A1 (fr) 2007-01-18 2008-07-24 Merck Patent Gmbh Dérivés de carbazole pour des dispositifs électroluminescents organiques
EP1968131A1 (fr) 2005-12-27 2008-09-10 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique et materiau pour celui-ci
WO2008145239A2 (fr) 2007-05-29 2008-12-04 Merck Patent Gmbh Nouveaux matériaux destinés à des dispositifs électroluminescents organiques
WO2009003455A1 (fr) 2007-07-04 2009-01-08 Novaled Ag Composés quinoïdes et leur utilisation dans des matériaux de base semi-conducteurs, des composants électroniques et des composants optoélectroniques
EP2045848A1 (fr) 2007-07-18 2009-04-08 Idemitsu Kosan Co., Ltd. Matériau de dispositif électroluminescent organique et dispositif électroluminescent organique
WO2009062578A1 (fr) 2007-11-12 2009-05-22 Merck Patent Gmbh Dispositifs organiques électroluminescents contenant des complexes azométhine/métal
WO2009100925A1 (fr) 2008-02-13 2009-08-20 Merck Patent Gmbh Nouveaux matériaux pour des dispositifs organiques électroluminescents
WO2009146770A2 (fr) 2008-06-05 2009-12-10 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques
WO2010006680A1 (fr) 2008-07-18 2010-01-21 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010012328A1 (fr) 2008-07-29 2010-02-04 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2010015306A1 (fr) 2008-08-08 2010-02-11 Merck Patent Gmbh, Dispositif électroluminescent organique
WO2010015307A1 (fr) 2008-08-04 2010-02-11 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques avec des ligands isonitriles
WO2010031485A1 (fr) 2008-09-22 2010-03-25 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
US20100096600A1 (en) 2008-10-16 2010-04-22 Novaled Ag Square Planar Transition Metal Complexes and Organic Semiconductive Materials Using Them as Well as Electronic or Optoelectric Components
WO2010054730A1 (fr) 2008-11-11 2010-05-20 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2010054729A2 (fr) 2008-11-11 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010054731A1 (fr) 2008-11-13 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010054728A1 (fr) 2008-11-13 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010072300A1 (fr) 2008-12-22 2010-07-01 Merck Patent Gmbh Dispositif électroluminescent organique contenant des dérivés triazine
EP2213662A1 (fr) 2007-11-30 2010-08-04 Idemitsu Kosan Co., Ltd. Dérivé d'azaindénofluorènedione, matière de dispositif électroluminescent organique et dispositif électroluminescent organique
WO2010086089A1 (fr) 2009-02-02 2010-08-05 Merck Patent Gmbh Complexes métalliques
WO2010094378A1 (fr) 2009-02-17 2010-08-26 Merck Patent Gmbh Dispositif électronique organique
WO2010099852A1 (fr) 2009-03-02 2010-09-10 Merck Patent Gmbh Complexes métalliques avec des ligands azaborol, et dispositif électronique correspondant
WO2010102709A1 (fr) 2009-03-13 2010-09-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010108579A1 (fr) 2009-03-23 2010-09-30 Merck Patent Gmbh Dispositif électroluminescent organique
WO2010136109A1 (fr) 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011000455A1 (fr) 2009-06-30 2011-01-06 Merck Patent Gmbh Matériaux destinés à des dispositifs d'électroluminescence organique
EP2276085A1 (fr) 2008-03-27 2011-01-19 Nippon Steel Chemical Co., Ltd. Dispositif électroluminescent organique
WO2011032626A1 (fr) 2009-09-16 2011-03-24 Merck Patent Gmbh Complexes métalliques
WO2011042107A2 (fr) 2009-10-08 2011-04-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011054442A2 (fr) 2009-11-06 2011-05-12 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2011057706A2 (fr) 2009-11-14 2011-05-19 Merck Patent Gmbh Matières pour dispositif électroniques
WO2011060859A1 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
WO2011060867A1 (fr) 2009-11-18 2011-05-26 Merck Patent Gmbh Hétérocycles condensés contenant de l'azote pour des oled
WO2011060877A2 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
WO2011066898A1 (fr) 2009-12-05 2011-06-09 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques
WO2011073149A1 (fr) 2009-12-14 2011-06-23 Basf Se Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques et leur utilisation dans des oled
WO2011088877A1 (fr) 2010-01-25 2011-07-28 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2011116865A1 (fr) 2010-03-25 2011-09-29 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2011120709A1 (fr) 2010-03-31 2011-10-06 Osram Opto Semiconductors Gmbh Dopant pour une couche conductrice de trous pour composants semi-conducteurs organiques, et son utilisation
US8044390B2 (en) 2007-05-25 2011-10-25 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device, organic electroluminescent device, and organic electroluminescent display
WO2011137951A1 (fr) 2010-05-04 2011-11-10 Merck Patent Gmbh Dispositifs électroluminescents organiques
US8057712B2 (en) 2008-04-29 2011-11-15 Novaled Ag Radialene compounds and their use
WO2011157339A1 (fr) 2010-06-15 2011-12-22 Merck Patent Gmbh Complexes métalliques
WO2012007086A1 (fr) 2010-07-16 2012-01-19 Merck Patent Gmbh Complexes métalliques
WO2012034627A1 (fr) 2010-09-15 2012-03-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2012048780A1 (fr) 2010-10-15 2012-04-19 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2012048781A1 (fr) 2010-10-15 2012-04-19 Merck Patent Gmbh Matériaux à base de triphényles pour dispositifs électroluminescents organiques
WO2012095143A1 (fr) 2011-01-13 2012-07-19 Merck Patent Gmbh Composés pour des dispositifs électroluminescents organiques
US20120187826A1 (en) 2009-12-21 2012-07-26 Idemitsu Kosan Co., Ltd. Organic electroluminescent element using pyrene derivative
WO2012143080A2 (fr) 2011-04-18 2012-10-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2012150001A1 (fr) 2011-05-05 2012-11-08 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2013041176A1 (fr) 2011-09-21 2013-03-28 Merck Patent Gmbh Dérivés de carbazole pour des dispositifs électroluminescents organiques
WO2013056776A1 (fr) 2011-10-20 2013-04-25 Merck Patent Gmbh Matériaux destinés à des dispositifs électroluminescents organiques
WO2013083216A1 (fr) 2011-11-17 2013-06-13 Merck Patent Gmbh Dérivés de spiro-dihydroacridine et leur application comme matériaux pour dispositifs électroluminescents organiques
WO2013120577A1 (fr) 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
DE102012209523A1 (de) 2012-06-06 2013-12-12 Osram Opto Semiconductors Gmbh Hauptgruppenmetallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien
WO2013185871A1 (fr) 2012-06-12 2013-12-19 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2014008982A1 (fr) 2012-07-13 2014-01-16 Merck Patent Gmbh Complexes metalliques
WO2014015937A1 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Composés et dispositifs electroluminescents organiques
WO2014015938A1 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Dérivés de 2-diarylaminofluorène et composés électroniques organiques les contenant
WO2014015935A2 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Composés et dispositifs electroniques organiques
WO2014023377A2 (fr) 2012-08-07 2014-02-13 Merck Patent Gmbh Complexes métalliques
WO2014037077A1 (fr) 2012-09-04 2014-03-13 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2014072017A1 (fr) 2012-11-12 2014-05-15 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2014094961A1 (fr) 2012-12-21 2014-06-26 Merck Patent Gmbh Complexes métalliques
WO2014094960A1 (fr) 2012-12-21 2014-06-26 Merck Patent Gmbh Complexes métalliques
WO2014106522A1 (fr) 2013-01-03 2014-07-10 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2014111269A2 (fr) 2013-10-14 2014-07-24 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2015022051A1 (fr) 2013-08-15 2015-02-19 Merck Patent Gmbh Matériaux destinés à des dispositifs électroniques
WO2015036074A1 (fr) 2013-09-11 2015-03-19 Merck Patent Gmbh Complexes métalliques
WO2015082056A1 (fr) 2013-12-06 2015-06-11 Merck Patent Gmbh Composés et dispositifs électroniques organiques
WO2015086108A1 (fr) 2013-12-12 2015-06-18 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2015102118A1 (fr) 2014-02-18 2015-07-09 学校法人関西学院 Composé aromatique polycyclique
WO2015104045A1 (fr) 2014-01-13 2015-07-16 Merck Patent Gmbh Complexes métalliques
WO2015117718A1 (fr) 2014-02-05 2015-08-13 Merck Patent Gmbh Complexes métalliques
WO2015131976A1 (fr) 2014-03-07 2015-09-11 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015158409A1 (fr) 2014-04-16 2015-10-22 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015158411A1 (fr) 2014-04-14 2015-10-22 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015169412A1 (fr) 2014-05-05 2015-11-12 Merck Patent Gmbh Matières pour des dispositifs organiques électroluminescents
WO2016015810A1 (fr) 2014-07-29 2016-02-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016015815A1 (fr) 2014-07-28 2016-02-04 Merck Patent Gmbh Complexes métalliques
WO2016023608A1 (fr) 2014-08-13 2016-02-18 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016078738A1 (fr) 2014-11-18 2016-05-26 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2016087017A1 (fr) 2014-12-01 2016-06-09 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2016102048A1 (fr) 2014-12-22 2016-06-30 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2016124304A1 (fr) 2015-02-03 2016-08-11 Merck Patent Gmbh Complexes métalliques
WO2016131521A1 (fr) 2015-02-16 2016-08-25 Merck Patent Gmbh Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques
WO2016150544A1 (fr) 2015-03-25 2016-09-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016152418A1 (fr) 2015-03-25 2016-09-29 学校法人関西学院 Composé aromatique polycyclique et composition de formation de couche d'émission de lumière
WO2017025165A1 (fr) 2015-08-12 2017-02-16 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2017028940A1 (fr) 2015-08-14 2017-02-23 Merck Patent Gmbh Dérivés de phénoxazine pour dispositifs électroluminescents organiques
WO2017028941A1 (fr) 2015-08-14 2017-02-23 Merck Patent Gmbh Dérivés de phénoxazine pour dispositifs électroluminescents organiques
WO2017032439A1 (fr) 2015-08-25 2017-03-02 Merck Patent Gmbh Complexes métalliques
WO2017036574A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Dérivés de 6,9,15,18-tétrahydro-s-indacéno[1,2-b:5,6-b']difluorène et leur utilisation dans des dispositifs électroniques
WO2017036573A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2017148564A1 (fr) 2016-03-03 2017-09-08 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018011186A1 (fr) 2016-07-14 2018-01-18 Merck Patent Gmbh Complexes métalliques
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
WO2018095397A1 (fr) 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Composé organique contenant du bore et ses utilisations, mélange organique et dispositif électronique organique
WO2018178001A1 (fr) 2017-03-29 2018-10-04 Merck Patent Gmbh Complexes métalliques
WO2019004248A1 (fr) 2017-06-30 2019-01-03 住友化学株式会社 Composé macromoléculaire, et élément luminescent mettant en œuvre celui-ci
WO2019020538A1 (fr) 2017-07-25 2019-01-31 Merck Patent Gmbh Complexes métalliques
WO2019115423A1 (fr) 2017-12-13 2019-06-20 Merck Patent Gmbh Complexes métalliques
WO2019132040A1 (fr) 2017-12-28 2019-07-04 出光興産株式会社 Nouveau composé et élément électroluminescent organique
WO2019158453A1 (fr) 2018-02-13 2019-08-22 Merck Patent Gmbh Complexes métalliques
WO2020067143A1 (fr) * 2018-09-25 2020-04-02 国立大学法人京都大学 Composé, matériau luminescent, substance à fluorescence retardée, élément luminescent organique, capteur d'oxygène, et procédé et programme de conception d'une molécule
US20200161552A1 (en) 2018-11-21 2020-05-21 Sfc Co., Ltd. Indolocarbazole derivatives and organic electroluminescent devices using the same
WO2020208051A1 (fr) 2019-04-11 2020-10-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2021089450A1 (fr) 2019-11-04 2021-05-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20210100352A (ko) * 2020-02-06 2021-08-17 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Patent Citations (172)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
WO1995009147A1 (fr) 1993-09-29 1995-04-06 Idemitsu Kosan Co., Ltd. Element electroluminescent organique et derive d'arylenediamine
EP0652273A1 (fr) 1993-11-09 1995-05-10 Shinko Electric Industries Co. Ltd. Matériau organique pour dispositif électroluminescent et dispositif électroluminescent
EP0676461A2 (fr) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Composés spiro et leur application comme matières électroluminescentes
JP2000053957A (ja) 1998-06-23 2000-02-22 Koto Gijutsu Kenkyuin Kenkyu Kumiai 新規な有機金属発光物質およびそれを含む有機電気発光素子
WO2000070655A2 (fr) 1999-05-13 2000-11-23 The Trustees Of Princeton University Dispositifs electroluminescents organiques a tres haute performance utilisant l'electrophosphorescence
WO2001041512A1 (fr) 1999-12-01 2001-06-07 The Trustees Of Princeton University Complexes de forme l2mx en tant que dopants phosphorescents pour del organiques
WO2001049806A1 (fr) 1999-12-31 2001-07-12 Lg Chemical Co., Ltd Dispositif electronique comprenant un compose organique presentant les caracteristiques de semi-conduction du dopage p
EP1205527A1 (fr) 2000-03-27 2002-05-15 Idemitsu Kosan Co., Ltd. Dispositif a electroluminescence organique
WO2002002714A2 (fr) 2000-06-30 2002-01-10 E.I. Du Pont De Nemours And Company Composes d'iridium electroluminescents contenant des phenylpyridines fluores, des phenylpyrimidines et des phenylquinolines, et dispositifs fabriques avec ces composes
WO2002015645A1 (fr) 2000-08-11 2002-02-21 The Trustees Of Princeton University Composes organometalliques et electrophosphorescence organique presentant un deplacement d'emission
EP1191612A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent, dispositif d'affichage et composé complexe d'un métal
EP1191613A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent, dispositif d'affichage et composé complexe d'un métal
EP1191614A2 (fr) 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Dispositif luminescent et composé complexe d'un métal utilisé pour ce dispositif
WO2002072714A1 (fr) 2001-03-10 2002-09-19 Covion Organic Semiconductors Gmbh Solutions et dispersions de semi-conducteurs organiques
WO2003019694A2 (fr) 2001-08-24 2003-03-06 Covion Organic Semiconductors Gmbh Solutions de semi-conducteurs polymeres
WO2003060956A2 (fr) 2002-01-18 2003-07-24 Lg Chem, Ltd. Nouveau materiau permettant de transporter des electrons et affichage organique electroluminescent utilisant ledit materiau
WO2004013080A1 (fr) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Derives de spirobifluorene, leur preparation et leurs utilisations
EP1553154A1 (fr) 2002-08-23 2005-07-13 Idemitsu Kosan Co., Ltd. Dispositif organique electroluminescent et derive d'anthracene
WO2004028217A1 (fr) 2002-09-20 2004-04-01 Idemitsu Kosan Co., Ltd. Element organique electroluminescent
WO2004058911A2 (fr) 2002-12-23 2004-07-15 Covion Organic Semiconductors Gmbh Element electroluminescent organique
WO2004081017A1 (fr) 2003-03-11 2004-09-23 Covion Organic Semiconductors Gmbh Complexes metalliques
WO2004080975A1 (fr) 2003-03-13 2004-09-23 Idemitsu Kosan Co., Ltd. Derive heterocyclique contenant de l'azote et element electroluminescent organique utilisant ce derive
JP2004288381A (ja) 2003-03-19 2004-10-14 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子
WO2004093207A2 (fr) 2003-04-15 2004-10-28 Covion Organic Semiconductors Gmbh Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges
EP1617711A1 (fr) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Dispositif organique electroluminescent et affichage
EP1617710A1 (fr) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Materiau pour dispositif electroluminescent organique, dispositif electroluminescent organique, dispositif d'eclairage et affichage
WO2005011013A1 (fr) 2003-07-21 2005-02-03 Covion Organic Semiconductors Gmbh Element electroluminescent organique
WO2005019373A2 (fr) 2003-08-19 2005-03-03 Basf Aktiengesellschaft Complexes de metal de transition comportant des ligands de carbene faisant office d'emetteurs pour diodes electroluminescentes organiques (delo)
WO2005033244A1 (fr) 2003-09-29 2005-04-14 Covion Organic Semiconductors Gmbh Complexes metalliques
US20050069729A1 (en) 2003-09-30 2005-03-31 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
WO2005039246A1 (fr) 2003-09-30 2005-04-28 Konica Minolta Holdings, Inc. Dispositif electroluminescent organique, dispositif d'eclairage et afficheur
WO2005084082A1 (fr) 2004-02-20 2005-09-09 Merck Patent Gmbh Dispositifs electroniques organiques
WO2005084081A1 (fr) 2004-02-20 2005-09-09 Merck Patent Gmbh Dispositifs electroniques organiques
EP1722602A1 (fr) 2004-03-05 2006-11-15 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique et affichage electroluminescent organique
EP1731584A1 (fr) 2004-03-31 2006-12-13 Konica Minolta Holdings, Inc. Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, écran et dispositif d'éclairage
WO2005111172A2 (fr) 2004-05-11 2005-11-24 Merck Patent Gmbh Nouveaux melanges de materiaux pour applications electroluminescentes
US20050258742A1 (en) 2004-05-18 2005-11-24 Yui-Yi Tsai Carbene containing metal complexes as OLEDs
EP1749809A1 (fr) 2004-05-27 2007-02-07 Idemitsu Kosan Co., Ltd. Derive de pyrene asymetrique et dispositif electroluminescent organique utilisant celui-ci
JP2005347160A (ja) 2004-06-04 2005-12-15 Konica Minolta Holdings Inc 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
WO2006005627A1 (fr) 2004-07-15 2006-01-19 Merck Patent Gmbh Derives oligomeres de spirobifluorene, leur elaboration et leur utilisation
WO2006048268A1 (fr) 2004-11-06 2006-05-11 Merck Patent Gmbh Dispositif electroluminescent organique
EP1661888A1 (fr) 2004-11-29 2006-05-31 Samsung SDI Co., Ltd. Composé contenant un phenylcarbazole et dispositif organiques électroluminiscent l'utilisant
WO2006097208A1 (fr) 2005-03-16 2006-09-21 Merck Patent Gmbh Nouveaux materiaux pour des dispositifs electroluminescents organiques
WO2006100896A1 (fr) 2005-03-18 2006-09-28 Idemitsu Kosan Co., Ltd. Derive d’amine aromatique et dispositif electroluminescent organique l’utilisant
WO2006108497A1 (fr) 2005-04-14 2006-10-19 Merck Patent Gmbh Composes pour dispositifs electroniques organiques
WO2006117052A1 (fr) 2005-05-03 2006-11-09 Merck Patent Gmbh Dispositif electroluminescent organique, et derives d'acide boronique et d'acide borinique utilises pour produire ce dispositif electroluminescent organique
WO2006122630A1 (fr) 2005-05-20 2006-11-23 Merck Patent Gmbh Composes pour dispositifs electroniques organiques
WO2006131192A1 (fr) 2005-06-09 2006-12-14 Merck Patent Gmbh Nouveaux materiaux destines a des dispositifs electroluminescents organiques
EP1905754A1 (fr) 2005-07-06 2008-04-02 Idemitsu Kosan Co., Ltd. Dérivé du pyrène et dispositif électroluminescent organique l utilisant
US20070092755A1 (en) 2005-10-26 2007-04-26 Eastman Kodak Company Organic element for low voltage electroluminescent devices
WO2007063754A1 (fr) 2005-12-01 2007-06-07 Nippon Steel Chemical Co., Ltd. Compose pour element electroluminescent organique et element electroluminescent organique
WO2007065550A1 (fr) 2005-12-08 2007-06-14 Merck Patent Gmbh Nouvelles matières pour dispositifs électroluminescents organiques
WO2007065678A1 (fr) 2005-12-08 2007-06-14 Merck Patent Gmbh Nouvelles matieres pour dispositifs electroluminescents organiques
EP1968131A1 (fr) 2005-12-27 2008-09-10 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique et materiau pour celui-ci
WO2007110129A1 (fr) 2006-03-24 2007-10-04 Merck Patent Gmbh Nouveaux materiaux pour disposifs electroluminescents organiques
WO2007137725A1 (fr) 2006-05-31 2007-12-06 Merck Patent Gmbh Nouveaux matériaux pour dispositifs électroluminescents organiques
WO2007140847A1 (fr) 2006-06-02 2007-12-13 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2008006449A1 (fr) 2006-07-11 2008-01-17 Merck Patent Gmbh Nouveaux matériaux destinés à des dispositifs électroluminescents organiques
WO2008056746A1 (fr) 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique
WO2008086851A1 (fr) 2007-01-18 2008-07-24 Merck Patent Gmbh Dérivés de carbazole pour des dispositifs électroluminescents organiques
US8044390B2 (en) 2007-05-25 2011-10-25 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device, organic electroluminescent device, and organic electroluminescent display
WO2008145239A2 (fr) 2007-05-29 2008-12-04 Merck Patent Gmbh Nouveaux matériaux destinés à des dispositifs électroluminescents organiques
WO2009003455A1 (fr) 2007-07-04 2009-01-08 Novaled Ag Composés quinoïdes et leur utilisation dans des matériaux de base semi-conducteurs, des composants électroniques et des composants optoélectroniques
DE102007031220A1 (de) 2007-07-04 2009-01-08 Novaled Ag Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen
EP2045848A1 (fr) 2007-07-18 2009-04-08 Idemitsu Kosan Co., Ltd. Matériau de dispositif électroluminescent organique et dispositif électroluminescent organique
WO2009062578A1 (fr) 2007-11-12 2009-05-22 Merck Patent Gmbh Dispositifs organiques électroluminescents contenant des complexes azométhine/métal
EP2213662A1 (fr) 2007-11-30 2010-08-04 Idemitsu Kosan Co., Ltd. Dérivé d'azaindénofluorènedione, matière de dispositif électroluminescent organique et dispositif électroluminescent organique
WO2009100925A1 (fr) 2008-02-13 2009-08-20 Merck Patent Gmbh Nouveaux matériaux pour des dispositifs organiques électroluminescents
EP2276085A1 (fr) 2008-03-27 2011-01-19 Nippon Steel Chemical Co., Ltd. Dispositif électroluminescent organique
US8057712B2 (en) 2008-04-29 2011-11-15 Novaled Ag Radialene compounds and their use
WO2009146770A2 (fr) 2008-06-05 2009-12-10 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques
WO2010006680A1 (fr) 2008-07-18 2010-01-21 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010012328A1 (fr) 2008-07-29 2010-02-04 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2010015307A1 (fr) 2008-08-04 2010-02-11 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques avec des ligands isonitriles
WO2010015306A1 (fr) 2008-08-08 2010-02-11 Merck Patent Gmbh, Dispositif électroluminescent organique
WO2010031485A1 (fr) 2008-09-22 2010-03-25 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
US20100096600A1 (en) 2008-10-16 2010-04-22 Novaled Ag Square Planar Transition Metal Complexes and Organic Semiconductive Materials Using Them as Well as Electronic or Optoelectric Components
WO2010054730A1 (fr) 2008-11-11 2010-05-20 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2010054729A2 (fr) 2008-11-11 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010054731A1 (fr) 2008-11-13 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010054728A1 (fr) 2008-11-13 2010-05-20 Merck Patent Gmbh Matières pour des dispositifs électroluminescents organiques
WO2010072300A1 (fr) 2008-12-22 2010-07-01 Merck Patent Gmbh Dispositif électroluminescent organique contenant des dérivés triazine
WO2010086089A1 (fr) 2009-02-02 2010-08-05 Merck Patent Gmbh Complexes métalliques
WO2010094378A1 (fr) 2009-02-17 2010-08-26 Merck Patent Gmbh Dispositif électronique organique
WO2010099852A1 (fr) 2009-03-02 2010-09-10 Merck Patent Gmbh Complexes métalliques avec des ligands azaborol, et dispositif électronique correspondant
WO2010102709A1 (fr) 2009-03-13 2010-09-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010108579A1 (fr) 2009-03-23 2010-09-30 Merck Patent Gmbh Dispositif électroluminescent organique
WO2010136109A1 (fr) 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011000455A1 (fr) 2009-06-30 2011-01-06 Merck Patent Gmbh Matériaux destinés à des dispositifs d'électroluminescence organique
WO2011032626A1 (fr) 2009-09-16 2011-03-24 Merck Patent Gmbh Complexes métalliques
WO2011042107A2 (fr) 2009-10-08 2011-04-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011054442A2 (fr) 2009-11-06 2011-05-12 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2011057706A2 (fr) 2009-11-14 2011-05-19 Merck Patent Gmbh Matières pour dispositif électroniques
WO2011060859A1 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
WO2011060877A2 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
WO2011060867A1 (fr) 2009-11-18 2011-05-26 Merck Patent Gmbh Hétérocycles condensés contenant de l'azote pour des oled
WO2011066898A1 (fr) 2009-12-05 2011-06-09 Merck Patent Gmbh Dispositif électronique contenant des complexes métalliques
WO2011073149A1 (fr) 2009-12-14 2011-06-23 Basf Se Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques et leur utilisation dans des oled
US20120187826A1 (en) 2009-12-21 2012-07-26 Idemitsu Kosan Co., Ltd. Organic electroluminescent element using pyrene derivative
WO2011088877A1 (fr) 2010-01-25 2011-07-28 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2011116865A1 (fr) 2010-03-25 2011-09-29 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2011120709A1 (fr) 2010-03-31 2011-10-06 Osram Opto Semiconductors Gmbh Dopant pour une couche conductrice de trous pour composants semi-conducteurs organiques, et son utilisation
WO2011137951A1 (fr) 2010-05-04 2011-11-10 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2011157339A1 (fr) 2010-06-15 2011-12-22 Merck Patent Gmbh Complexes métalliques
WO2012007086A1 (fr) 2010-07-16 2012-01-19 Merck Patent Gmbh Complexes métalliques
WO2012034627A1 (fr) 2010-09-15 2012-03-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2012048780A1 (fr) 2010-10-15 2012-04-19 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2012048781A1 (fr) 2010-10-15 2012-04-19 Merck Patent Gmbh Matériaux à base de triphényles pour dispositifs électroluminescents organiques
WO2012095143A1 (fr) 2011-01-13 2012-07-19 Merck Patent Gmbh Composés pour des dispositifs électroluminescents organiques
WO2012143080A2 (fr) 2011-04-18 2012-10-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2012150001A1 (fr) 2011-05-05 2012-11-08 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2013041176A1 (fr) 2011-09-21 2013-03-28 Merck Patent Gmbh Dérivés de carbazole pour des dispositifs électroluminescents organiques
WO2013056776A1 (fr) 2011-10-20 2013-04-25 Merck Patent Gmbh Matériaux destinés à des dispositifs électroluminescents organiques
WO2013083216A1 (fr) 2011-11-17 2013-06-13 Merck Patent Gmbh Dérivés de spiro-dihydroacridine et leur application comme matériaux pour dispositifs électroluminescents organiques
WO2013120577A1 (fr) 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
DE102012209523A1 (de) 2012-06-06 2013-12-12 Osram Opto Semiconductors Gmbh Hauptgruppenmetallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien
WO2013185871A1 (fr) 2012-06-12 2013-12-19 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2014008982A1 (fr) 2012-07-13 2014-01-16 Merck Patent Gmbh Complexes metalliques
WO2014015937A1 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Composés et dispositifs electroluminescents organiques
WO2014015938A1 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Dérivés de 2-diarylaminofluorène et composés électroniques organiques les contenant
WO2014015935A2 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Composés et dispositifs electroniques organiques
WO2014023377A2 (fr) 2012-08-07 2014-02-13 Merck Patent Gmbh Complexes métalliques
WO2014037077A1 (fr) 2012-09-04 2014-03-13 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2014072017A1 (fr) 2012-11-12 2014-05-15 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2014094961A1 (fr) 2012-12-21 2014-06-26 Merck Patent Gmbh Complexes métalliques
WO2014094960A1 (fr) 2012-12-21 2014-06-26 Merck Patent Gmbh Complexes métalliques
WO2014106522A1 (fr) 2013-01-03 2014-07-10 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2015022051A1 (fr) 2013-08-15 2015-02-19 Merck Patent Gmbh Matériaux destinés à des dispositifs électroniques
WO2015036074A1 (fr) 2013-09-11 2015-03-19 Merck Patent Gmbh Complexes métalliques
WO2014111269A2 (fr) 2013-10-14 2014-07-24 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2015082056A1 (fr) 2013-12-06 2015-06-11 Merck Patent Gmbh Composés et dispositifs électroniques organiques
WO2015086108A1 (fr) 2013-12-12 2015-06-18 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2015104045A1 (fr) 2014-01-13 2015-07-16 Merck Patent Gmbh Complexes métalliques
WO2015117718A1 (fr) 2014-02-05 2015-08-13 Merck Patent Gmbh Complexes métalliques
WO2015102118A1 (fr) 2014-02-18 2015-07-09 学校法人関西学院 Composé aromatique polycyclique
WO2015131976A1 (fr) 2014-03-07 2015-09-11 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015158411A1 (fr) 2014-04-14 2015-10-22 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015158409A1 (fr) 2014-04-16 2015-10-22 Merck Patent Gmbh Matières pour dispositifs électroniques
WO2015169412A1 (fr) 2014-05-05 2015-11-12 Merck Patent Gmbh Matières pour des dispositifs organiques électroluminescents
WO2016015815A1 (fr) 2014-07-28 2016-02-04 Merck Patent Gmbh Complexes métalliques
WO2016015810A1 (fr) 2014-07-29 2016-02-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016023608A1 (fr) 2014-08-13 2016-02-18 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016078738A1 (fr) 2014-11-18 2016-05-26 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2016087017A1 (fr) 2014-12-01 2016-06-09 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2016102048A1 (fr) 2014-12-22 2016-06-30 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2016124304A1 (fr) 2015-02-03 2016-08-11 Merck Patent Gmbh Complexes métalliques
WO2016131521A1 (fr) 2015-02-16 2016-08-25 Merck Patent Gmbh Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques
WO2016150544A1 (fr) 2015-03-25 2016-09-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016152418A1 (fr) 2015-03-25 2016-09-29 学校法人関西学院 Composé aromatique polycyclique et composition de formation de couche d'émission de lumière
WO2017025165A1 (fr) 2015-08-12 2017-02-16 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2017028940A1 (fr) 2015-08-14 2017-02-23 Merck Patent Gmbh Dérivés de phénoxazine pour dispositifs électroluminescents organiques
WO2017028941A1 (fr) 2015-08-14 2017-02-23 Merck Patent Gmbh Dérivés de phénoxazine pour dispositifs électroluminescents organiques
WO2017032439A1 (fr) 2015-08-25 2017-03-02 Merck Patent Gmbh Complexes métalliques
WO2017036574A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Dérivés de 6,9,15,18-tétrahydro-s-indacéno[1,2-b:5,6-b']difluorène et leur utilisation dans des dispositifs électroniques
WO2017036573A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2017148564A1 (fr) 2016-03-03 2017-09-08 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2017148565A1 (fr) 2016-03-03 2017-09-08 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018011186A1 (fr) 2016-07-14 2018-01-18 Merck Patent Gmbh Complexes métalliques
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
WO2018095397A1 (fr) 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Composé organique contenant du bore et ses utilisations, mélange organique et dispositif électronique organique
WO2018178001A1 (fr) 2017-03-29 2018-10-04 Merck Patent Gmbh Complexes métalliques
WO2019004248A1 (fr) 2017-06-30 2019-01-03 住友化学株式会社 Composé macromoléculaire, et élément luminescent mettant en œuvre celui-ci
WO2019020538A1 (fr) 2017-07-25 2019-01-31 Merck Patent Gmbh Complexes métalliques
WO2019115423A1 (fr) 2017-12-13 2019-06-20 Merck Patent Gmbh Complexes métalliques
WO2019132040A1 (fr) 2017-12-28 2019-07-04 出光興産株式会社 Nouveau composé et élément électroluminescent organique
WO2019158453A1 (fr) 2018-02-13 2019-08-22 Merck Patent Gmbh Complexes métalliques
WO2020067143A1 (fr) * 2018-09-25 2020-04-02 国立大学法人京都大学 Composé, matériau luminescent, substance à fluorescence retardée, élément luminescent organique, capteur d'oxygène, et procédé et programme de conception d'une molécule
US20200161552A1 (en) 2018-11-21 2020-05-21 Sfc Co., Ltd. Indolocarbazole derivatives and organic electroluminescent devices using the same
WO2020208051A1 (fr) 2019-04-11 2020-10-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2021089450A1 (fr) 2019-11-04 2021-05-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20210100352A (ko) * 2020-02-06 2021-08-17 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Y. IMAZAKI ET AL., J. AM. CHEM. SOC., vol. 134, 2012, pages 14760
Y. IMAZAKI ET AL.: "Suzuki-Kupplung, unter Einführung eines Aryl-Triazins, gefolgt von einem Ruthenium-katalysierten Triflat-Bromid-Austausch nach", J. AM. CHEM. SOC., vol. 134, 2012, pages 14760
Y. SHIROTA ET AL., CHEM. REV., vol. 107, no. 4, 2007, pages 953 - 1010

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