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EP3928360A1 - Composition pour dispositifs électroniques organiques - Google Patents

Composition pour dispositifs électroniques organiques

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Publication number
EP3928360A1
EP3928360A1 EP19827743.6A EP19827743A EP3928360A1 EP 3928360 A1 EP3928360 A1 EP 3928360A1 EP 19827743 A EP19827743 A EP 19827743A EP 3928360 A1 EP3928360 A1 EP 3928360A1
Authority
EP
European Patent Office
Prior art keywords
aromatic
organic
substituted
group
occurrence
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19827743.6A
Other languages
German (de)
English (en)
Inventor
Amir Parham
Jonas Kroeber
Jens ENGELHART
Christian Ehrenreich
Christian EICKHOFF
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP3928360A1 publication Critical patent/EP3928360A1/fr
Pending legal-status Critical Current

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Classifications

    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/486—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising two or more active layers, e.g. forming pn heterojunctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to a composition which comprises an electron-transporting host and a hole-transporting host, their use in electronic devices and electronic devices containing this composition.
  • the electron-transporting host is particularly preferably selected from the class of the triazine-dibenzofuran-carbazole systems or the class of the triazine-dibenzothiophene-carbazole systems.
  • the hole-transporting host is preferably selected from the class of the biscarbazoles.
  • organic electroluminescent devices e.g. OLEDs - organic light emitting diodes or OLECs - organic light emitting electro-chemical cells
  • OLEDs organic light emitting diodes
  • OLECs organic light emitting electro-chemical cells
  • organometallic complexes used the phosphorescence instead
  • organometallic compounds as phosphorescence emitters, an up to fourfold increase in energy and power efficiency is possible.
  • OLEDs in particular also with OLEDs, the
  • organic electroluminescent devices are not only determined by the emitters used.
  • the other materials used such as host and matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials are of particular importance here, and of these in particular the host or matrix materials. Improvements in these materials can lead to significant improvements in electroluminescent devices.
  • matrix material is also often used when a host material for phosphorescent emitters is meant. This use of the term also applies to the present invention. Meanwhile, a variety of host materials have been used for both fluorescent and
  • Another possibility of improving the performance data of electronic devices consists in using combinations of two or more materials, in particular host materials or matrix materials.
  • No. 6,392,250 B1 discloses the use of a mixture consisting of an electron transport material, a hole transport material and a fluorescent emitter in the emission layer of an OLED. With the help of this mixture, the service life of the OLED could be improved compared to the prior art.
  • No. 6,803,720 B1 discloses the use of a mixture containing a phosphorescent emitter and also a hole and an electron transport material in the emission layer of an OLED. Both the hole and electron transport materials are small organic molecules.
  • triazine-dibenzofuran-carbazole derivatives and triazine-dibenzothiophene-carbazole derivatives can also be used in a mixture.
  • the carbazole derivative is not bound to the dibenzofuran or dibenzothiophene base via the N atom of the carbazole. So will For example, the production of the OLED with identification E34 is described, which contains the host materials EG1, IC6 and the phosphorescent emitter TEG1 in the light-emitting layer. The structures of the compounds used are listed below:
  • triazine-dibenzofuran-carbazole derivatives and triazine-dibenzothiophene-carbazole derivatives can also be used in a mixture.
  • Carbazole derivatives also include compounds such as indenocarbazole and indolocarbazole. The connection of the carbazole derivative to the dibenzofuran or
  • Dibenzothiophene basic body takes place according to the description via the N atom of the carbazole at position 8 of the dibenzofuran / dibenzothiophene.
  • the triazine substituent is in the 4-position of the directly or via a linker
  • Dibenzofuran / dibenzothiophene bound Dibenzofuran / dibenzothiophene bound.
  • the production of the OLED with the E9 label is described, the host materials EG9, IC3 and the host materials in the light-emitting layer
  • triazine-dibenzofuran-carbazole derivatives for example, triazine-dibenzothiophene-carbazole derivatives can be used as host material in a light-emitting layer.
  • Triazine substituent is directly or via a linker in the 1 position
  • Dibenzofurans / Dibenzothiophens bound The carbazole derivative is bound directly or via a linker in the 6-position of the dibenzofuran / dibenzothiophene. It is further reported that these materials can be mixed with a biscarbazole H2 in a ratio of 10:90 to 90:10.
  • KR20160046077 describes special triazine-dibenzofuran-carbazole and triazine-dibenzothiophene-carbazole derivatives in a light-emitting layer together with a further host material.
  • US9771373 describes an organic light-emitting device with a light-emitting layer containing two host materials, the host materials each being made up of special groups of
  • Dibenzofurans / Dibenzothiophens is bound.
  • compounds can be used in a mixture with another matrix material.
  • KR2018010149 describes similar compounds as in WO
  • WO 2018/174678 and WO 2018/174679 disclose devices containing a mixture of carbazole-dibenzofuran derivatives with biscarbazoles in an organic layer, the
  • Linking of the carbazole unit to the dibenzofuran structure is possible at any position of the dibenzofuran, but is preferably in the 6- or 7-position.
  • the disclosure EP3415512 describes, among other things
  • Pyrimidine or triazine substituent can be attached directly or via a linker in position 1 of the dibenzofuran and at least two identical substituents L2-Ar3 must be attached in the 6- and 8-position of the dibenzofuran.
  • Ar3 can be a carbazole bonded via N. In the examples, such compounds are used in combination with a specific biscarbazole.
  • the object of the present invention is therefore to provide materials which are suitable for use in an organic compound
  • Electroluminescent devices and in particular in one
  • Phosphorescent OLED are suitable and have good device properties, in particular with regard to improved current efficiency, improved Operating voltage and / or improved service life, lead, as well as the provision of the corresponding electronic device.
  • compositions solve this problem and eliminate the disadvantages of the prior art.
  • Such compositions lead to very good properties of organic electronic devices, in particular organic electroluminescent devices, in particular with regard to current efficiency, operating voltage and / or service life and in particular also in the presence of a light-emitting device
  • Component in the emission layer in particular in combination with emitters of the formula (3), at concentrations between 2 and 25% by weight.
  • the devices according to the invention show, in particular, very good current efficiency.
  • a first aspect of the present invention is therefore one
  • Composition comprising at least one compound of the formula (1) and at least one compound of the formula (2),
  • Xi is on each occurrence, identically or differently, CR ° or N, with the proviso that at least one group Xi stands for N;
  • X is on each occurrence, identically or differently, C or N, where two adjacent X can be bonded to a ring system of the formula A,
  • Y 1 is selected from NAr-i, C (R * ) 2, 0 or S;
  • Y is selected from 0 or S
  • L is, identically or differently, a simple at each occurrence
  • aromatic ring atoms which can be substituted by one or more radicals R 5 ;
  • n and m are independently 0, 1, 2 or 3 on each occurrence
  • o, p and q are independently 0, 1, 2, 3 or 4 on each occurrence;
  • An is on each occurrence, independently of one another, an aryl or heteroaryl group with 5 to 40 aromatic ring atoms which can be substituted by one or more radicals R 3 ;
  • RA is H, -I_3-Ar4, or -Li-N (Ar) 2;
  • RB is Ar3 or -l_2-N (Ar) 2; Li , l_ 2, are identical or different on each occurrence
  • _3 is a single bond or an aromatic
  • Ring atoms which can be substituted by one or more radicals R 3 , where a substituent R 3 can form a ring with a substituent R 2 on the carbazole;
  • Ar3 is an aromatic ring system with 6 to 40 aromatic rings
  • Ar4 is on each occurrence, identically or differently, an unsubstituted or substituted 9-aryl-carbazolyl or unsubstituted or substituted carbazol-9-yl, which can be substituted by one or more radicals R 4 and where, independently of one another, one or more radicals in each case 4 or a radical R 4 together with a radical R 2 can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl denotes an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms which can be substituted by R 3 ;
  • R * is on each occurrence, identically or differently, a straight-chain alkyl group with 1 to 10 carbon atoms or an aryl group with 6 to
  • R °, R, R 1 'R 2 are identical or different on each occurrence
  • aromatic ring atoms each of which can be substituted with one or more radicals R 3 , an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms which can be substituted with one or more radicals R 3 , or an aralkyl or heteroaralkyl group with 5 to 40 aromatic ring atoms which can be substituted by one or more radicals R 3 ; optionally two substituents R ° and / or R and / or R 1 and / or R 2 which are bonded to the same carbon atom or to adjacent carbon atoms can be monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic
  • Form ring system which can be substituted with one or more radicals R 3 ;
  • R 3 is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, N (Ar) 2 , an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms in which one or more Fl atoms can be replaced by D, F, CI, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; this can be two or more adjacent
  • R 3 substituents form a mono- or polycyclic, aliphatic ring system with one another;
  • R 4 is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which a or several Fl atoms through D, F, CI, Br,
  • Carbon atoms or CN can be replaced; two or more adjacent substituents R 4 here can form a mono- or polycyclic ring system with one another;
  • R 5 is selected identically or differently on each occurrence from the group consisting of D, F, CN and an aryl group with 6 to 18 carbon atoms, two or more adjacent substituents R 5 can be a mono- or polycyclic, aliphatic Form ring system;
  • Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted by one or more non-aromatic radicals R 3 ; two radicals Ar, which bond to the same N atom, P atom or B atom, can also be formed by a single bond or a bridge selected from N (R 3 ), C (R 3 ) 2 , O or S, with one another be bridged and
  • r is independently 0, 1, 2 or 3 on each occurrence
  • s means 0, 1, 2, 3 or 4 independently of one another on each occurrence.
  • compositions contain that use this
  • compositions in an organic electronic device organic electronic devices preferred
  • Electroluminescent devices incorporating such compositions contain, and thereby preferably contain the composition in one layer, as well as methods for producing such devices.
  • the corresponding preferred embodiments, as described below, are also the subject of the present invention. The surprising and beneficial effects are due to specific
  • the layer comprising the composition comprising at least one
  • Compound of the formula (1) and at least one compound of the formula (2), as described above or preferably described below, is in particular a light-emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) and / or a hole blocking layer (HBL).
  • EML light-emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • HBL hole blocking layer
  • a light-emitting layer If it is a light-emitting layer, then it is preferably a phosphorescent layer, which is characterized in that, in addition to the composition, it comprises the
  • Matrix materials of formula (1) and formula (2), as described above, contains a phosphorescent emitter.
  • Adjacent carbon atoms in the context of the present invention are carbon atoms that are directly linked to one another. Under the wording that two or more radicals unite with one another
  • Can form ring is to be understood in the context of the present description, inter alia, that the two radicals are linked to one another by a chemical bond with formal elimination of two hydrogen atoms. This is illustrated by the following scheme. However, the above formulation should also include
  • an aryl group contains 6 to 40 aromatic ring atoms, preferably carbon atoms.
  • a fleteroaryl group contains 5 to 40 aromatic ring atoms, the ring atoms comprising C atoms and at least one fletero atom, with the proviso that the sum of C atoms and fletero atoms is at least 5.
  • the fleteroatoms are preferably selected from N, O and / or S.
  • An aryl group or fleteroaryl group is either a simple aromatic cycle, that is phenyl, derived from benzene, or a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene , or a condensed aryl or fleteroaryl group, for example derived from naphthalene, anthracene, phenanthrene,
  • An aryl group with 6 to 18 carbon atoms is therefore preferably phenyl, naphthyl, phenanthryl or
  • Triphenylenyl whereby the attachment of the aryl group as a substituent is not restricted.
  • An arylene group with 6 to 18 carbon atoms is therefore preferably phenylene, naphthylene, phenanthrylene or triphenylenylene, the arylene group not being linked as a linker
  • An aromatic ring system for the purposes of this invention contains 6 to 40 carbon atoms in the ring system and can be substituted by one or more radicals R 3 , where R 3 has a meaning described below.
  • An aromatic ring system also contains aryl groups as previously described.
  • An aromatic ring system with 6 to 18 carbon atoms is preferably composed of phenylene, biphenylene, naphthylene, phenanthrenylene and
  • Triphenylenylene selected, it being possible for the particular aromatic ring system to be substituted by one or more radicals R 5 .
  • a heteroaromatic ring system for the purposes of this invention contains 5 to 40 ring atoms and at least one heteroatom and can be substituted by one or more radicals R 3 , R 3 being one below
  • Ring system has 10 to 40 ring atoms and at least one heteroatom and can be substituted by one or more radicals R 3 , where R 3 has a meaning described below.
  • R 3 has a meaning described below.
  • Ring system also contains heteroaryl groups as previously described.
  • the heteroatoms in the heteroaromatic ring system are preferably selected from N, O and / or S.
  • aromatic or heteroaromatic ring system in the context of this invention is understood to mean a system which does not necessarily contain only aryl or heteroaryl groups, but also in which several aryl or heteroaryl groups are formed by a non-aromatic unit
  • atoms other than H e.g. B. a C, N or O atom or a carbonyl group
  • a C, N or O atom or a carbonyl group can be interrupted.
  • systems such as 9,9‘-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. should also be used as aromatic or
  • heteroaromatic ring systems are understood in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl group or by a silyl group are interrupted. Furthermore, systems in which two or more aryl or heteroaryl groups are bonded directly to one another, such as. B. biphenyl, terphenyl, quaterphenyl or bipyridine, also included in the definition of the aromatic or heteroaromatic ring system.
  • R 3 can be substituted and which can be linked via any positions on the aromatic or heteroaromatic, examples are understood as groups that are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, Benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cisenzoindenofluorene, truenzoindenofluorene, or trans-dibenzoindenofluorene
  • Anthroxazole phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline,
  • Ar is, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 on each occurrence
  • aromatic ring atoms that do not have one or more
  • aromatic radicals R 3 can be substituted; two radicals Ar, which bond to the same N atom, P atom or B atom, can also be formed by a single bond or a bridge selected from N (R 3 ), C (R 3 ) 2, O or S, with one another be bridged.
  • the substituent R 3 has been described above or is preferably described below.
  • cyclic alkyl, alkoxy or thioalkyl group in the context of this invention is a monocyclic, a bicyclic or a
  • a C1 to C20 alkyl group in which individual H atoms or Chh groups can also be substituted by the groups mentioned above, for example the radicals methyl, ethyl, n-propyl, i-propyl, Cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1 -methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-
  • An alkenyl group includes, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl,
  • Cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl understood.
  • alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
  • a C1 to C2o alkoxy group is understood as meaning, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • a Ci- to C20-thioalkyl group includes, for example, S-
  • Understood alkyl groups for example thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n-propoyl, 1-thio-i-butyl, 1-thio-n-butyl or 1-thio-t-butyl.
  • Ring atoms means O-aryl or O-heteroaryl and means that the aryl or heteroaryl group is bonded via an oxygen atom.
  • Ring atoms means that an alkyl group, as described above, is substituted with an aryl group or heteroaryl group.
  • a phosphorescent emitter within the meaning of the present invention is a compound which shows luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • a spin state> 1 in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides are intended be regarded as phosphorescent emitters. A more precise definition is given below.
  • composition comprises at least one compound of the formula (1), as described above or as preferred below
  • At least one compound of the formula (2), as described above or described below, is used as matrix material for a phosphorescent emitter, it is preferred if its triplet energy is not significantly smaller than the triplet energy of the phosphorescent emitter.
  • the triplet level Ti (emitter) - Ti (matrix) ⁇ 0.2 eV, particularly preferably ⁇ 0.15 eV, very particularly preferably ⁇ 0.1 eV applies.
  • Ti (matrix) is the triplet level of the matrix material in the emission layer, this condition applying to each of the two matrix materials, and T-i (emitter) is the triplet level of the phosphorescent emitter. If the emission layer contains more than two matrix materials, the above-mentioned relationship preferably also applies to any further matrix material.
  • Composition and / or device are contained, for example as electron-transporting floes.
  • composition of the invention contains at least one
  • Y is selected from O or S.
  • compounds of the formula (1) in which Y is S are selected.
  • the symbol Xi stands at least once for N, preferably twice for N and once for CR ° or three times for N.
  • R ° is on each occurrence, identically or differently, preferably selected from the group consisting of H, D, F or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms. R ° is particularly preferably H.
  • At least one compound of the formula (1 a) is particularly preferably selected for the composition, with substituents which are described above, preferably described or preferably described below.
  • Another object of the invention is accordingly a
  • composition as described above, where the compound of the formula (1) corresponds to the compound of the formula (1 a), preferably when the symbol Y corresponds to 0.
  • Another object of the invention is accordingly a
  • composition as described above, wherein the compound of formula (1) corresponds to the compound of formula (1 a), preferably when the symbol Y corresponds to S.
  • substituent R is preferably selected identically or differently on each occurrence from the Group consisting of D, F, one
  • the heteroaromatic ring system with 5 to 40 aromatic ring atoms is in this case preferably derived from dibenzofuran or for R
  • the aromatic ring system with 6 to 40 aromatic ring atoms is in this case for R preferably phenyl, biphenyl or terphenyl, particularly preferably phenyl or [1, 1 ', 2', 1 "] -terphenyl-5'-yl.
  • the alkyl group with 1 to 40 carbon atoms for R is preferably a linear or branched alkyl group with 1 to 4 carbon atoms, particularly preferably methyl, ethyl, n-propyl or n-butyl, very particularly preferably methyl.
  • n and m are preferably 0.
  • Preferred compounds of the formulas (1) or (1 a) in which n and m denote 0 and the symbols X have a meaning, as preferably described above, are accordingly compounds of the formulas (1 b), (1 c), (1 d),
  • the substituents R 1 are preferably selected independently of one another from group H, D or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which can in each case be substituted by one or more radicals R 3 , where R 3 has a meaning given above or below and where two substituents R 1 are adjacent carbon atoms form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted by one or more radicals R 3 .
  • the substituents R 1 are in
  • the carbazole in the compounds of the formulas (1), (1a) and (1b) preferably bears a substituent R 1 that is different from Fl and one
  • aromatic ring system with 5 to 40 aromatic ring atoms
  • R 3 is one given above or given below
  • the carbazole in the compounds of the formulas (1), (1 a) and (1 b) preferably bears a substituent R 1 , which is different from H and corresponds to a heteroaromatic ring system with 5 to 40 aromatic ring atoms.
  • compounds described by formulas (1), (1 a) (h 1) to the substituents R 1 are each independently preferably selected from the group Fl or unsubstituted or mono- or polysubstituted by R 3 substituted phenyl, 1, 2-biphenyl , 1,3-biphenyl, 1,4-biphenyl, triphenylenyl, 1-naphthyl, 2-naphthyl, carbazol-9-yl or 9-aryl-carbazolyl, where aryl is an aromatic or heteroaromatic
  • Ring system with 5 to 30 aromatic ring atoms means which can be substituted in each case by one or more radicals R 3 .
  • Dibenzothiophenyl group is not restricted here.
  • At least one An stands for An-1 and the other aromatic substituent An stands for an aryl group with 6 to 40 C-
  • Atoms which can be substituted by one or more radicals R 3 or for a dibenzofuranyl or a dibenzothiophenyl group preferably selected from An-1 to An-12.
  • Particularly preferably at least one An stands for phenyl and the other aromatic substituent stands for a phenyl group which can be substituted by one or more radicals R 3 or for dibenzofuranyl or dibenzothiophenyl.
  • Both groups An are very particularly preferably the same. Both groups An are very particularly preferably phenyl. Both groups An are preferably each, independently of one another, An-5, An-6, An-7 or An-11, particularly preferably both groups An are An-6.
  • Occurring identically or differently preferably selected from the group consisting of D, F or an aromatic or heteroaromatic Ring system with 5 to 40 aromatic ring atoms.
  • the heteroaromatic ring system with 5 to 40 aromatic ring atoms is in this case for R 3 preferably derived from dibenzofuran or dibenzothiophene.
  • the aromatic ring system with 6 to 40 aromatic ring atoms is in this case for R 3 preferably phenyl, biphenyl or terphenyl, particularly preferably phenyl.
  • the aryl group or fleteroaryl group in An is preferably each independently substituted once with R 3 .
  • the aryl group or fleteroaryl group in An is particularly preferably substituted once by R 3 .
  • the substituent R 3 on dibenzofuranyl or dibenzothiophenyl is preferably Fl.
  • the substituent R 3 on the aryl group with 6 to 40 carbon atoms is preferably phenyl or F1 when it occurs.
  • the aryl group or fleteroaryl group are very particularly preferably unsubstituted in An.
  • Y 1 means NAn, C (R *) 2, O or S, where An is given a meaning given above or is preferred has given meaning.
  • NAn preferably has the meaning N-phenyl.
  • Y 1 preferably denotes NAn or C (R * ) 2.
  • Formulas (1), (1 a), (1 d) and (1 e) are preferred in which Y 1 has a previously or in which Y 1 denotes NAn and 0, particularly preferably NAn denotes.
  • the substituent R * is on each occurrence, identically or differently, a straight-chain alkyl group with 1 to 10 carbon atoms or an aryl group with 6 up to 12 carbon atoms, where the two substituents R * can together form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted by one or more substituents R 5 .
  • R * is preferably the same on each occurrence or two substituents R * together form a monocyclic or polycyclic,
  • R * is particularly preferably selected from methyl, ethyl or phenyl. Particularly preferably, two substituents R * together with the carbon atom to which they are attached form a ring system selected from
  • Substituents R 5 can be substituted.
  • the ring system formed by two substituents R * particularly preferably corresponds to a spirobifluorene.
  • Y 1 is particularly preferably selected from N-phenyl, C (methyl) 2, O or S. Y 1 is very particularly preferably C (methyl) 2.
  • Y 1 is very particularly preferably C (methyl) 2.
  • (1a), (1 b), (1 c), (1 d), (1 e), (1 f), (1g) or (1 h) or in preferred compounds of the formulas (1), (1 a), (1 b), (1 c), (1 d), (1 e), (1 f), (1 g) or (1 h) is L at each occurrence identically or differently a single bond or an aromatic ring system with 6 to 30 aromatic ring atoms which can be substituted by one or more radicals R 5 , where R 5 has a meaning as described above.
  • R 5 is preferably selected from the group consisting of D or phenyl.
  • L is preferably a single bond or aromatic ring system with 6 to 18 carbon atoms, preferably for phenylene, biphenylene, naphthylene, phenanthrenylene or triphenylenylene, the attachment to the other substituents not being restricted.
  • Phenylene can be linked to the dibenzofuran / dibenzothiophene unit in the ortho, meta or para position, for example.
  • L can therefore preferably be selected from the following linkers L-1 to L-20, which are unsubstituted or can be substituted by R 5 , as described above:
  • the linkers L-1 to L-20 are preferably unsubstituted.
  • the linkers L-1 to L-7 are particularly preferably used.
  • L is preferably a single bond or a linker selected from the group L-1 to L7 or L-2 and L-3.
  • L is particularly preferably a
  • Particularly preferred compounds of the formula (1) correspond to the formulas (1 b) and (1 c), as described above.
  • Y is preferably 0, Y 1 is preferably C (R *) 2, An is independently preferably phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl-N- for each occurrence. phenylenyl,
  • Y is preferably 0, Y 1 is preferably C (R *) 2, An is independently preferably phenyl, dibenzofuranyl, dibenzothiophenyl and biphenyl on each occurrence, as before and L is a single bond.
  • Y is preferably S, Y 1 is preferably C (R *) 2, An is independently preferably phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl-N- for each occurrence phenylenyl,
  • Y is preferably S
  • Y 1 is preferably C (R *) 2
  • An is independently preferably phenyl, dibenzofuranyl, carbazolyl-N-phenylenyl and each occurrence 1,3-biphenyl as previously described and L is a single bond.
  • the preparation of the compounds of the formula (1) or the preferred compounds of the formulas (1a) to (1h) and of the compounds 1 to 36 and 67 to 81 is known to the person skilled in the art.
  • the compounds can be prepared by synthesis steps known to the person skilled in the art, such as halogenation, preferably bromination, and a subsequent organometallic coupling reaction, eg Suzuki coupling, Heck coupling or Hartwig-Buchwald coupling.
  • the preparation of the compounds of the formula (1) or the preferred compounds of the formulas (1 a) to (1 h) and the compounds 1 to 36 and 67 to 81 can be derived in particular from WO 2016/015810, in particular page 35 and the
  • the compounds of the formulas (1) to (1h) can be prepared according to the following scheme 1, where L, Xi, Y, R, R 1 , An, n, m, o, p has one of the meanings given above.
  • composition according to the invention contains at least one compound of the formula (2),
  • RA is H, -L3-Ar4, or -Li-N (Ar) 2;
  • RB is Ar3 or -l_2-N (Ar) 2; Li , ⁇ -2, are on each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 3 ;
  • l_3 is a single bond or an aromatic
  • Ring atoms which can be substituted by one or more radicals R 3 , where a substituent R 3 can form a ring with a substituent R 2 on the carbazole;
  • Ar3 is an aromatic ring system with 6 to 40 aromatic rings
  • Ar4 is on each occurrence, identically or differently, an unsubstituted or substituted 9-aryl-carbazolyl or unsubstituted or substituted carbazol-9-yl, which can be substituted by one or more radicals R 4 and where, independently of one another, one or more radicals in each case 4 or a radical R 4 together with a radical R 2 can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl denotes an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms which can be substituted by R 3 ;
  • Carbon atoms are bonded to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 3 ;
  • R 3 is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, N (Ar) 2, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms in which one or more Fl atoms can be replaced by D, F, CI, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; two or more adjacent substituents R 3 here can form a mono- or polycyclic, aliphatic ring system with one another;
  • R 4 is on each occurrence, identically or differently, selected from the group consisting of Fl, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which a or several Fl atoms through D, F, CI, Br, I, a straight-chain or branched alkyl group with 1 to 4
  • Carbon atoms or CN can be replaced; two can or more adjacent substituents R 4 with one another form a mono- or polycyclic ring system;
  • Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted by one or more non-aromatic radicals R 3 ; two radicals Ar, which bond to the same N atom, P atom or B atom, can also be formed by a single bond or a bridge selected from N (R 3 ), C (R 3 ) 2 , O or S, with one another be bridged and
  • r is independently 0, 1, 2 or 3 on each occurrence; s means, independently of one another, on each occurrence 0, 1, 2, 3 or
  • compounds of the formula (2) are selected as described above, those with compounds of the formulas
  • Li, l_2, L3, Ar, Ar3, Ar4, R 2 , r and s have a meaning mentioned above or below.
  • Preferred compounds of the formula (2) or (2a) are compounds of the formulas (2e), (2f), (2g), (2h) and (2i),
  • aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms means that with one or more radicals R 3 can be substituted, where a substituent R 2 on the carbazole can form a ring with a substituent R 3 , Z is C (R 3 ) 2, N-Ar, 0 or S and t is 0 or 1.
  • Preferred compounds of the formula (2) or (2c) in which at least r is 1 are compounds of the formulas (2j), (2k), (2I),
  • R 3 in the compounds of the formulas (2j), (2k) and (2I) is preferably Fl or an aromatic or heteroaromatic ring system with 5 to 40
  • R 3 in the compounds of the formulas (2j), (2k) and (2I) is preferably phenyl.
  • an index u, v or w stands for 1.
  • U, v and w 0 are particularly preferred.
  • H is excluded from the definition of the substituents R 2 if r and / or s is / are greater than 1.
  • Another object of the invention is accordingly a
  • a substituent R 2 and a substituent R 4 form a ring, for example also defined in formula (2f) by [Z] t , the following rings Z-1 to Z-7 preferably being formed and the dashed lines each representing the bond to the carbazoles:
  • two substituents R 2 can form a ring together one or more times or two substituents R 4 , if present, can form a ring together once or more times, this ring being independently of one another preferably composed of the following structures (S1) to ( S9) is selected, where # and # represent the respective point of attachment with the carbon atoms and the structures can each be substituted with one or more substituents R 3 :
  • R 3 in the substructures (S1) to (S9) is preferably H or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be substituted by R 5 , preferably H or phenyl.
  • Single bonds are each independently selected from the linkers L-2.1 to L-2.33,
  • the linkers L-2.1 to L-2.33 can be substituted by one or more radicals R 3 and the dashed lines indicate the connection to which mean carbazoles.
  • a radical R 3 on one of the linkers L-2.1 to L-2.33 can form a ring with a radical R 2 of the carbazole.
  • the linkers L-2.1 to L-2.33 are preferably unsubstituted or substituted by a phenyl.
  • Preferred linkers for Li are selected from the structures L-2.1 to L-2.33, in which W has the meaning S or 0, particularly preferably the meaning 0.
  • Preferred linkers for L3 are selected from the structures L-2.1 to L-2.33, in which W has the meaning 0, S or N-Ar, particularly preferably 0 or N-Ar.
  • W has the meaning 0, S or N-Ar, particularly preferably 0 or N-Ar.
  • the compounds of the formulas (2), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (2h) and (2i) are the two Carbazoles linked to one another in the 3-position.
  • r is preferably 0, 1 or 2, where R 2 is a previously given
  • r 0 or 1 has meaning or a meaning given below. Particularly preferred is r 0 or 1. Very particular preferred is r 0.
  • Occurrence identically or differently preferably selected from the group consisting of D, F, an alkyl group with 1 to 40 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 40
  • aromatic ring atoms which can be substituted by one or more radicals R 3 .
  • Ring system with 5 to 40 aromatic ring atoms in this R 2 is preferably derived from benzene, dibenzofuran, dibenzothiophene, 9-phenyl-carbazole, indolo [3,2,1-y / c] carbazole, biphenyl and terphenyl, which with one or more R 3 radicals can be substituted.
  • the preferred position of the substituent (s) [R 2 ] r is position 1, 2, 3 or 4 or the
  • s is in each case, independently of one another, on each occurrence, preferably 0, 1 or 2, where R 2 and R 4 have a meaning given above or a meaning given below. Particularly preferably s is 0 or 1 independently of one another in each occurrence, and s is very particularly preferably 0 in each occurrence.
  • substituent R 4 is preferably selected on each occurrence, identically or differently, from the group consisting of D, F, an alkyl group with 1 to 20 carbon atoms or one aromatic or heteroaromatic ring system with 5 to 30
  • Carbon atoms or CN can be replaced.
  • Two or more adjacent substituents R 4 can form a monocyclic or polycyclic ring system with one another.
  • the aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms in this R 4 is preferably derived from benzene, dibenzofuran, dibenzothiophene, 9-phenyl-carbazole, biphenyl, terphenyl and triphenylene.
  • the preferred position of the substituent ( s ) [R 4 ] s is position 1, 2 or 3, particularly preferably 3, where R 4 has one of the preferred meanings given above and s is greater than 0.
  • Ar in N (Ar) 2 is preferably derived from benzene, dibenzofuran, fluorene, spirobiflurene, dibenzothiophene, 9-phenyl-carbazole, biphenyl and
  • Terphenyl which can be substituted with one or more substituents R 3 .
  • Ar is preferably unsubstituted here.
  • Ring system preferably selected and derived from the group benzene, carbazole, 9-phenyl-carbazole, dibenzofuran, dibenzothiophene, fluorene, terphenyl or spirobifluorene, very particularly preferably derived from a dibenzofuran.
  • the substituent R 2 is, on each occurrence, identically or differently preferably selected from the group consisting of D, F, an alkyl group with 1 to 40 C atoms or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 3 .
  • the preferred position of the substituent ( s ) [R 2 ] s is position 1, 3 and 4, particularly preferably 3, where R 2 has one of the meanings given above.
  • s is 0 or 1. If in compounds of the formulas (2j), (2k) and (2I) s is 1, R 2 in [R 2 ] s is preferably phenyl.
  • Ar3 is each independent from each other an aromatic ring system with 6 to 40 aromatic ring atoms or a heteroaromatic ring system with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 3 .
  • Ar3 and aryl are preferably derived from benzene, dibenzofuran, fluorene, spirobiflurene, dibenzothiophene, 9-phenyl-carbazole, naphthalene,
  • Ring system optionally substituted by R 3 preferably contains only one N atom in its entirety or the ring system optionally substituted by R 3 contains one or more O and / or S atoms in its entirety.
  • aryl and Ar3 are preferably selected independently of one another on each occurrence from the aromatic or heteroaromatic ring systems Ar-1 to Ar-24,
  • Y 3 denotes, identically or differently, 0, NR # , S or C (R # ) 2 on each occurrence, where the radical R # which is bonded to N is not equal to H. and R 3 has the meaning mentioned above or a preferred meaning below and the dashed bond represents the bond to the N atom.
  • Y 3 is preferably O, S or C (CH3) 2. Y 3 is very particularly preferably O.
  • the substituent R 3 is selected identically or differently on each occurrence from the group consisting of Fl, D,
  • F, CN an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more F1 atoms are replaced by D, F, CI, Br, I or CN can be replaced and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; two or more adjacent substituents R 3 here can form a mono- or polycyclic, aliphatic ring system with one another.
  • the substituent R 3 is preferred for each
  • the substituent R 3 is preferably selected identically or differently on each occurrence from the group consisting of Fl or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, as described above, but preferably dibenzofuran ,
  • the substituent R 3 is particularly preferably Fl on each occurrence.
  • the preparation of the compounds of the formula (2) or the preferred compounds of the formulas (2), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (2h) , (2i), (2j), (2k) and (21), and the compounds of Table 2 and 37 to 66a are known to the person skilled in the art.
  • the compounds can be prepared by synthesis steps known to the person skilled in the art, such as halogenation, preferably bromination, and a subsequent organometallic coupling reaction, eg Suzuki coupling, Heck coupling or Hartwig-Buchwald coupling.
  • Some of the compounds of the formula (2) are commercially available.
  • Connections 37 to 66a are combined.
  • composition or organic electronic according to the invention is obtained by combining compounds 1 to 36 and 67 to 81 with the compounds in Table 2.
  • the concentration of the electron-transporting host material of the formula (1), as described above or preferably described, in the composition or mixture according to the invention or in the light-emitting layer of the device according to the invention is in
  • % even more preferably in the range from 30% by weight to 80% by weight, very particularly preferably in the range from 20% by weight to 60% by weight and most preferably in the range from 30% by weight to 50% by weight, based on the total composition / mixture or based on the total composition of the light-emitting layer.
  • the concentration of the hole-transporting host material of the formula (2), as previously described or described as preferred, in the The composition or mixture or the light-emitting layer of the device according to the invention is in the range from 10% by weight to 95% by weight, preferably in the range from 15% by weight to 90% by weight, more preferably in the range from 15% by weight. -% to 80% by weight, even more preferably in the range from 20% by weight to 70% by weight, very particularly preferably in the range from 40% by weight to 80% by weight and most preferably in the range from 50% by weight to 70% by weight based on the total
  • composition / mixture or based on the whole
  • composition of the light-emitting layer is Composition of the light-emitting layer.
  • the composition according to the invention can contain at least one compound of the formula (1), as described above or as described as preferred, and at least one compound of the formula (2), as described above or as described as preferred, also further compounds, in particular organic functional materials.
  • the composition according to the invention is a physical mixture of the at least one compound of the formula (1), the at least one compound of the formula (2) and optionally further organic functional materials as
  • the present invention therefore also relates to a composition which, in addition to the materials mentioned above, contains at least one further compound selected from the group consisting of hole injection materials, hole transport materials, hole blocking materials, wide band gap materials, fluorescent emitters, phosphorescent emitters , Host materials,
  • Electron blocking materials are Electron blocking materials, electron transport materials, and
  • Electron injection materials n-dopants and p-dopants.
  • the person skilled in the art has no difficulty in selecting these from a large number of materials known to him.
  • n-dopants are understood to mean reducing agents, ie electron donors.
  • p-dopants are understood to mean oxidizing agents, ie electron acceptors.
  • Wide-band-gap-material is understood here to mean a material within the meaning of the disclosure of US Pat. No. 7,294,849, which is characterized by a band gap of at least 3.5 eV, the band gap being understood to mean the distance between the HOMO and LUMO energy of a material .
  • composition according to the invention comprising at least one hole-transporting host of the formula (2) and at least one electron-transporting host of the formula (1), as described above or preferably described, additionally contains at least one light-emitting compound or an emitter, with phosphorescent emitters are particularly preferred.
  • the present invention also relates to a composition / mixture which, in addition to the aforementioned host materials 1 and 2, as previously described or preferably described, in particular mixtures M1 to M1597, also contains at least one phosphorescent emitter.
  • the present invention also relates to an organic one
  • electroluminescent device as described above or below or preferably described, wherein the light-emitting layer in addition to the host materials 1 and 2 mentioned above, as described above or preferably described, in particular the
  • phosphorescent emitter typically encompasses compounds in which the light emission is prohibited by a spin
  • Transition from an excited state with higher spin multiplicity that is to say a spin state> 1, takes place, for example, through a transition from a triplet state or a state with an even higher one
  • Spin quantum number for example a quintet state.
  • a transition from a triplet state is preferably understood here.
  • Preferred phosphorescence emitters are compounds that contain copper, molybdenum, tungsten, rhenium,
  • 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 2011/032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/117718, WO 2016/015815, WO 2016/124304, WO 2017/032439, WO 2015/036074, WO 2015/117718 and WO 2016/015815.
  • Preferred phosphorescent emitters contain a dibenzofuran or an azadibenzofuran structure in at least one ligand.
  • Preferred phosphorescent emitters correspond to the formula (3),
  • X is N or CR
  • R is H, D, a branched or linear alkyl group with 1 to 10 carbon atoms or a partially or fully deuterated branched or linear alkyl group with 1 to 10 carbon atoms or a cycloalkyl group with 4 to 7 carbon atoms, partially or completely can be substituted with deuterium.
  • n is preferably 1 and m is preferably 2.
  • one X is preferably selected from N and the other X are CR.
  • emitters of the formula (3) at least one R is preferably different from H.
  • two, three or four R are preferably different from H and have one of the meanings otherwise given above for the emitters of the formula (3).
  • Preferred examples of phosphorescent emitters are listed in Table 4 below.
  • each mixture M1 to M1597 is preferably combined with a compound of the formula (3) or a compound from Table 4 or 5.
  • the composition according to the invention preferably consists of at least one compound of the formula (1), at least one compound of the formula (2) and one or two emitters selected from
  • the light-emitting layer in the organic electroluminescent device containing a composition as previously described or preferably described and at least one phosphorescent emitter is preferably an infra-red emitting, yellow, orange, red, green, blue or ultra-violet emitting layer, particularly preferably a yellow or green emitting layer and very particularly preferably a green emitting layer containing at least one phosphorescent emitter preferably forms an infra-red emitting, yellow, orange, red, green, blue or ultra-violet emitting layer, particularly preferably a yellow or green emitting layer and very particularly preferably a green-emitting layer.
  • a yellow-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 540 to 570 nm.
  • An orange-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 570 to 600 nm.
  • a red-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 600 to 750 nm.
  • a green-emitting layer is understood to mean a layer whose
  • Photoluminescence maximum is in the range from 490 to 540 nm.
  • a blue-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 440 to 490 nm.
  • the photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, the layer having the composition according to the invention, ie containing emitter and matrix.
  • the photoluminescence spectrum of the layer is recorded, for example, with a commercially available photoluminescence spectrometer.
  • the photoluminescence spectrum of the selected emitter is usually measured in an oxygen-free solution, 10-5 molar, the measurement being made at room temperature and any solvent in which the selected emitter dissolves in the stated concentration is suitable.
  • Particularly suitable solvents are usually toluene or 2-methyl-THF, but also
  • Preferred phosphorescent emitters are therefore infra-red emitters, preferably of the formula (3) or from Table 4 or 5, their
  • Triplet energy Ti is preferably from ⁇ 1.9 eV to ⁇ 1.0 eV.
  • Preferred phosphorescent emitters are therefore red emitters, preferably of the formula (3) or from Table 4 or 5, their
  • Triplet energy Ti is preferably ⁇ 2.1 eV to ⁇ 1.9 eV.
  • Preferred phosphorescent emitters are therefore yellow emitters, preferably of the formula (3) or from Table 4 or 5, their
  • Triplet energy Ti is preferably ⁇ 2.3 eV to ⁇ 2.1 eV.
  • Preferred phosphorescent emitters are accordingly green emitters, preferably of the formula (3) or from Table 4 or 5, their
  • Triplet energy Ti is preferably from ⁇ 2.5 eV to ⁇ 2.3 eV.
  • Preferred phosphorescent emitters are therefore blue emitters, preferably of the formula (3) or from Table 4 or 5, their
  • Triplet energy Ti is preferably ⁇ 3.1 eV to ⁇ 2.5 eV.
  • Preferred phosphorescent emitters are therefore ultra-violet emitters, of the formula (3) or from Table 4 or 5, whose triplet energy Ti is preferably from ⁇ 4.0 eV to ⁇ 3.1 eV.
  • particularly preferred phosphorescent emitters are green or yellow emitters, preferably of the formula (3) or from Table 4 or 5, as described above.
  • very particularly preferred phosphorescent emitters are green emitters, preferably of the formula (3) or from Table 4 or 5, whose triplet energy Ti is preferably from ⁇ 2.5 eV to ⁇ 2.3 eV.
  • Green emitters are very particularly preferred, preferably the
  • Preferred fluorescent emitters are selected from the class of the arylamines.
  • an arylamine or an aromatic amine is understood to mean a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a condensed ring system, particularly 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
  • An aromatic anthracenamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to one anthracene group, preferably in the 9,10 position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysendiamines are defined analogously thereto, the diarylamino groups on the pyrene preferably being bonded in the 1-position or in the 1,6-position.
  • fluorescent emitters are indenofluorenamines or diamines, for example according to WO 2006/108497 or WO 2006/122630, benzoindenofluorenamines or diamines, for example according to WO 2008/006449, and dibenzoindenofluorenamines or diamines, for example according to WO 2007 / 140847, as well as the indenofluorene derivatives with condensed aryl groups disclosed in WO 2010/012328.
  • the composition according to the invention is used as a component of mixed matrix systems.
  • the mixed matrix systems preferably comprise three or four different matrix materials, particularly preferably three different matrix materials (that is, a further matrix component in addition to the one according to the invention
  • composition compositions
  • Particularly suitable matrix materials which in combination with the composition according to the invention as
  • Matrix components of a mixed matrix system that can be used are selected from wide-band-gap materials,
  • ETM Electron Transport Materials
  • HTM Hole Transport Materials
  • Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. More detailed information on mixed matrix systems is contained, inter alia, in the application WO 2010/108579. Particularly suitable matrix materials which can be used in combination with the composition according to the invention as matrix components of a mixed matrix system in phosphorescent or fluorescent organic electroluminescent devices are selected from the preferred matrix materials for phosphorescent emitters given below or the preferred matrix materials for fluorescent emitters, as the case may be what type of emitter is used.
  • the mixed matrix system is preferably optimized for an emitter of the formula (3) or from table 4 or 5.
  • oligoarylenes e.g. 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or
  • the condensed aromatic groups e.g. DPVBi or Spiro-DPVBi according to EP 676461
  • the polypodal metal complexes e.g. according to WO 2004/0810157
  • the hole-conducting compounds e.g. according to WO 2004/058911
  • the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides, etc. (e.g. according to
  • Particularly preferred floss materials are selected from the classes of oligoarylenes containing 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, containing anthracene, benzanthracene,
  • an oligoarylene is to be understood as a compound in which at least three aryl or arylene groups are bonded to one another.
  • composition according to the invention preferably for phosphorescent emitters, in addition to the composition according to the invention, come as before described, particularly preferably comprising a mixture
  • Preferred further matrix materials are selected from the classes of aromatic amines, especially triarylamines, e.g. B. according to US 2005/0069729, carbazole derivatives (e.g. CBP, N, N-
  • EP 1617711, EP 1731584, JP 2005/347160 indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746, ketones, e.g. B. according to WO 2004/093207 or WO 2010/006680, phosphine oxides, sulfoxides and sulfones, e.g. B. according to WO 2005/003253, Oligophenylenes, bipolar
  • Matrix materials e.g. B. according to WO 2007/137725, silanes, e.g. B. according to WO 2005/111172, azaboroles or boronic esters, e.g. B. according to WO 2006/117052, triazine derivatives, e.g. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, e.g. B. according to EP 652273 or
  • Tetraazasilol derivatives e.g. B. according to WO 2010/054729
  • diazaphosphole derivatives e.g. B. according to WO 2010/054730
  • aluminum complexes e.g. B. BAIQ.
  • the composition contains in addition to the ingredients
  • electron-transporting host and hole-transporting host do not have any further components, i.e. functional materials.
  • material mixtures which are used as such for producing the organic layer, preferably the emitting layer.
  • These systems are also known as premix systems, which are used as the only material source for vapor deposition and which have a constant mixing ratio for the Have vapor deposition. This enables the vapor deposition of a layer with a uniform distribution of the components to be achieved in a simple and fast manner, without the need for precise control of a large number of material sources.
  • Another object of the invention is accordingly a
  • Composition consisting of a compound of the formula (1), (1a) to (1h) or a compound selected from 1 to 36 and 67 to 81 and a compound of the formula (2), (2a) to (2I) or a compound selected from 37 to 66a.
  • composition according to the invention is suitable for use in a
  • Organic electronic device understood a device which contains at least one layer that contains at least one organic compound.
  • the device can also be inorganic
  • the invention accordingly also relates to the use of a composition as described above or preferably described, in particular a mixture selected from M1 to M1597, in an organic electronic device.
  • compositions can be processed by vapor deposition or from solution. If the compositions are applied from solution, are
  • Formulations of the composition according to the invention containing at least one further solvent are required. These formulations can be, for example, solutions, dispersions or emulsions. It It may be preferred to use mixtures of two or more solvents for this purpose.
  • the present invention therefore also provides a formulation comprising a composition according to the invention and at least one solvent.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-) -Fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4 - dimethyl anisole, 3,5-dimethyl anisole, acetophenone, a-terpineol,
  • the formulation can also contain at least one further organic or inorganic compound which is also in the
  • Electronic device is used, in particular an emitting compound, in particular a phosphorescent emitter and / or a further matrix material. Suitable emitting compounds and further matrix materials have already been listed above.
  • the present invention also relates to the use of the composition according to the invention in an organic
  • the organic electronic device is preferably selected from the organic integrated circuits (OlCs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photo receptors, wherein the organic electroluminescent devices are particularly preferred.
  • Organic electroluminescent devices containing at least one compound of the formula (1) and at least one compound of the formula (2), as previously described or described as preferred, are organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O lasers) and organic light-emitting diodes (OLEDs), OLECs and OLEDs are particularly preferred and OLEDs are most preferred.
  • OLETs organic light-emitting transistors
  • OFQDs organic field quench devices
  • OLEDs organic light-emitting electrochemical cells
  • O lasers organic laser diodes
  • OLEDs organic light-emitting diodes
  • the composition according to the invention is preferably used, as described above or described as preferred, in an electronic device in a layer with an electron-transporting function.
  • the layer is preferably an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL) and / or an emission layer (EML), particularly preferably an ETL, EIL and / or an EML.
  • EML electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • EML emission layer
  • the composition according to the invention is very particularly preferably used in an EML,
  • Another object of the present invention is therefore an organic electronic device which is selected in particular from one of the electronic devices mentioned above and which contains the summary according to the invention, as previously described or preferably described, preferably in an emission layer (EML), in an electron transport layer (ETL), in one
  • a phosphorescent layer which is characterized in that, in addition to the composition, as previously described or preferably described, a
  • the electronic device is therefore an organic electroluminescent device, very particularly preferably an organic light-emitting diode (OLED), which contains the composition according to the invention, as described above or preferably described, together with a phosphorescent emitter
  • OLED organic light-emitting diode
  • EML emission layer
  • Electroluminescent device comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, the at least one light-emitting layer at least one compound of formula (1) as host material 1 and contains at least one compound of the formula (2) as host material 2, the compounds of the formulas (1) and (2) having structures as described above or preferably described or described in combination as a special composition or mixture.
  • electroluminescent device comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, the at least one light-emitting layer
  • Layer contains at least one compound of formula (1) as floss material 1 and at least one compound of formula (2) as host material 2, the compounds of formulas (1) and (2) having structures as described above or preferably described or in combination described as a special composition or mixture, and wherein the at least one emission layer contains a phosphorescent emitter.
  • the light-emitting layer in the device according to the invention preferably contains between 99.9 and 1% by volume, more preferably between 99 and 10% by volume, particularly preferably between 98 and 60% by volume, very particularly preferably between 97 and 80% by volume of matrix material composed of at least one compound of the formula (1) and at least one compound of the formula (2), as above
  • the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99% by volume, more preferably between 1 and 90% by volume, particularly preferably between 2 and 40% by volume, very particularly preferably between 3 and 20 Vol .-% of the emitter based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, instead of the above specified amounts in% by volume, preferably the corresponding amounts in% by weight are used.
  • the light-emitting layer in the device according to the invention preferably contains the matrix material of the formula (1) and the matrix material of the formula (2) in a volume percentage ratio between 3: 1 and 1: 3, preferably between 1: 2.5 and 1: 1 , particularly preferably between 1: 2 and 1: 1. If the compounds are processed from solution, the corresponding ratio in% by weight is preferably used instead of the ratio in% by volume given above.
  • an electronic device can also contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers,
  • Hole blocking layers light emitting layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers (interlayers),
  • the sequence of the layers in an organic electroluminescent device is preferably the following:
  • An organic electroluminescent device can contain a plurality of light-emitting layers.
  • at least one of the light-emitting layers contains the combination of compounds of the formula (1) and compounds of the formula (2), as previously described.
  • these emission layers particularly preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, i.e. H. in the light-emitting layers are different emitting
  • Three-layer systems are particularly preferred, that is to say systems with three light-emitting layers, the three layers showing blue, green and orange or red emission (for the basic structure, see, for example, WO 2005/011013). It should be noted that for the
  • a single emitter connection which is used and which emits in a broad wavelength range can also be suitable.
  • Suitable charge transport materials such as those in the hole injection or hole transport layer or electron blocking layer or in the electron transport layer of the organic electro according to the invention
  • Luminescent devices can be used, for example, those disclosed in Y. Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010
  • Aluminum complexes for example Alq3, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, are particularly suitable,
  • Lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives Lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.
  • WO 2004/028217, WO 2004/080975 and WO 2010/072300 are disclosed.
  • Particularly preferred hole transport materials are materials which can be used in a hole transport, hole injection or electron blocking layer, such as indenofluorenamine derivatives (e.g. according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, Hexaazatriphenylene derivatives (e.g. according to WO 01/049806), amine derivatives with condensed aromatics (e.g. according to US Pat. No. 5,061,569), the amine derivatives disclosed in WO 95/09147, monobenzoindenofluorenamines (e.g. according to WO 08/006449) , Dibenzoindenofluorenamines (e.g.
  • spirobifluorenamines e.g. according to WO 2012/034627 or the as yet unpublished EP 12000929.5
  • fluorene amines e.g. according to WO 2014/015937, WO 2014/015938 and WO 2014/015935
  • spiro-dibenzopyran amines e.g. according to WO 2013/083216
  • dihydroacridine derivatives e.g. WO 2012/150001.
  • alkaline earth metals such as alkaline earth metals
  • Alkali metals main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
  • alloys made of an alkali or alkaline earth metal and silver such as an alloy of
  • Magnesium and silver In the case of multi-layer structures, in addition to the metals mentioned, other metals can be used that have a relatively high work function, such as. B. Ag or Al, in which case combinations of metals such as Ca / Ag, Mg / Ag or Ba / Ag are then usually used. It can also be preferred to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. For example, alkali metal or
  • Alkaline earth metal fluorides but also the corresponding oxides or
  • LiF, L12O, BaF2, MgO, NaF, CsF, CS2CO3, etc. Lithium quinolinate (LiQ) can also be used for this.
  • the layer thickness of this layer is preferably between 0.5 and 5 nm.
  • Materials with a high work function are preferred as the anode.
  • the anode preferably has a work function greater than 4.5 eV vs. Vacuum on.
  • metals with a high redox potential are suitable for this, such as Ag, Pt or Au.
  • metal / metal oxide electrodes for example Al / Ni / NiO x , Al / PtO x
  • at least one of the electrodes must be transparent or
  • anode materials are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • ITO Indium tin oxide
  • IZO indium zinc oxide
  • the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • the organic electronic device containing the composition according to the invention is characterized in that one or more organic layers containing the composition according to the invention are coated using a sublimation process.
  • the materials are vapor-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 that the initial pressure is 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 with the OVPD (Organic Vapor Phase Deposition) process or with the aid of a carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and structured in this way (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
  • an organic electroluminescent device characterized in that one or more organic layers containing the composition according to the invention from solution, such as. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing) can be produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink-jet printing
  • Processing from solution has the advantage that the layer containing the
  • composition according to the invention can be applied very easily and inexpensively. This technique is particularly suitable for mass production of organic electronic devices.
  • Hybrid processes are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited.
  • Another object of the invention is therefore a method for
  • OVPD Organic Vapor Phase Deposition
  • an organic layer which is intended to contain the composition according to the invention and which can comprise several different constituents can be applied or vapor-deposited on any substrate.
  • the materials used can each be in a
  • the invention accordingly further provides a method, characterized in that the at least one compound of the formula (1), as described above or described as preferred, and the at least one compound of the formula (2), as described above or described as preferred , successively or simultaneously from at least two material sources, optionally with further materials, as described above or preferably described, are deposited from the gas phase and form the organic layer.
  • the at least one organic layer is applied by means of gas phase deposition, the constituents of the composition being premixed and evaporated from a single material source.
  • Embodiments are in particular the mixtures M4 (1 +40), M5 (1 +41), M24 (2 + 37), M26 (2 + 39), M33 (2 + 46), M44 (2 + 57), M48 (3 +38), M50 (3 + 40), M70 (4 + 37), M72 (4 + 39), M81 (4 + 48), M100 (5 + 44), M101 (5 + 45), M117 (6+ 38), M130 (6 + 51), M146 (7 + 44), M165 (8 + 40), M166
  • the invention accordingly also relates to a method, characterized in that the composition according to the invention, as described above or preferably described, is used as a material source for the gas phase deposition of the host system, and
  • Another object of the invention is a method for producing an organic electronic device containing a
  • composition according to the invention as described above or preferably described, characterized in that the
  • formulation according to the invention as described above, is used to apply the organic layer.
  • compositions according to the invention or the
  • compositions according to the invention in organic electronic devices, in particular in an organic electroluminescent device, and in particular in an OLED or OLEC, leads to significant increases in current efficiency with a comparable or improved service life of the devices.
  • Example 1 As can be seen in Example 1 given below, by using compounds according to the prior art, for example the compound SoA1, at low emitter concentrations in the EML of 8% in Example V1, a good voltage, but a relatively low one
  • Emitter concentrations of 2 to 25 percent by volume preferably at emitter concentrations of 5 to 15 percent by volume, particularly preferably at emitter concentrations of 7, 8 and 12 percent by volume, in the
  • Emission layer can be achieved.
  • Volume percent preferably at emitter concentrations of 5 to 15 volume percent, particularly preferably at emitter concentrations of 7, 8 and 12 volume percent, can be achieved in the emission layer.
  • Compound 4 to compounds of the prior art, such as SoA1, is in the 8-position in the connection to the dibenzofuran.
  • compositions according to the invention are very suitable for use in an emission layer and show improved performance data, in particular for service life, operating voltage and / or Current efficiency versus prior art compounds as previously described.
  • compositions according to the invention can easily be processed and are therefore very suitable for mass production in commercial use.
  • compositions according to the invention can be premixed and vapor-deposited from a single material source, so that an organic layer with an even distribution of the components used can be produced in a simple and rapid manner.
  • organometallic compounds designated with the "M-org.” method
  • the geometry is optimized using the Hartree-Fock method and the LanL2MB basic set (Gaussian input line "# HF / LanL2MB opt") (charge 0,
  • Cyclic voltammetry measurements calibrated HOMO and LUMO values in electron volts are determined as follows:
  • HOMO (eV) (HEh * 27.212) * 0.8308-1.118;
  • the triplet level T1 of a material is defined as its relative
  • Excitation energy (in eV) of the triplet state with the lowest energy which results from the quantum chemical energy calculation.
  • the singlet level S1 of a material is defined as its relative
  • Excitation energy (in eV) of the singlet state with the second lowest energy which results from the quantum chemical energy calculation.
  • the energetically lowest singlet state is called SO.
  • Pretreatment for examples V1 to E55 glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm, are first treated with an oxygen plasma, followed by an argon plasma, before coating. These plasma-treated glass plates form the substrates on which the OLEDs are applied.
  • the OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electrons
  • EBL emission layer
  • EML emission layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • cathode is formed by a 100 nm thick aluminum layer.
  • Table 6 The exact structure of the OLEDs is shown in Table 6.
  • the materials required to produce the OLEDs are shown in Table 8.
  • the device data of the OLEDs are listed in Table 7.
  • Examples V1, V2, V3, V10 and V11 are comparative examples with an electron-transporting host according to the prior art CN107973786.
  • Examples C4, C5, C6 and C7 are comparative examples with the host according to the prior art WO 2015/014435.
  • the examples V8 and V9 are
  • Examples E1 to E55 show data from
  • the emission layer always consists of at least two
  • Matrix materials and an emitting dopant which is added to the matrix material or the matrix materials by co-vaporization in a certain volume proportion.
  • a specification such as SoA1: 40: TEG3 (32%: 60%: 8%) means that the material SoA1 in a volume proportion of 32%, the connection 40 as co-host in a proportion of 60% and TEG3 in a proportion of 8% is present in the layer.
  • the electron transport layer can also consist of a mixture of two materials.
  • the OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and the current efficiency (SE, measured in cd / A) as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a
  • the electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and the CIE 1931 x and y color coordinates are calculated therefrom.
  • the specification U 10 in Table 7 denotes the voltage that is required for a current density of 10 mA / cm 2 .
  • SE10 denotes the current efficiency which is achieved at 10mA / cm 2 .
  • the service life LT is defined as the time after which the luminance drops to a certain proportion L1 during operation with the same starting brightness L0.
  • Emission layer can be used in phosphorescent green OLEDs.
  • the reaction mixture is refluxed for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The yield is 79.1 g (151 mmol; 72% of theory).
  • Tris (dibenzylideneacetone) dipalladium [CAS 51364-51-3] was added and the reaction mixture was refluxed for 16 h.
  • the reaction mixture is cooled to room temperature and the solvent is removed under reduced pressure.
  • the solid obtained is washed with 300 ml of ethanol and recrystallized several times from a mixture of heptane and xylene. After hot filtration through Alox and subsequent sublimation in a high vacuum, the purified product is obtained as a colorless solid 21.1 g (29.5 mmol; 69%).

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Abstract

La présente invention concerne une composition qui comprend un hôte transporteur d'électrons et un hôte transporteur de trous, son utilisation dans des dispositifs électroniques, ainsi que des dispositifs électroniques contenant cette composition. L'hôte transporteur d'électrons est choisi tout particulièrement dans la classe des systèmes triazine-dibenzofuranne-carbazole ou dans la classe des systèmes triazine-dibenzotiophène-carbazole. L'hôte transporteur de trous est choisi de préférence dans la classe des biscarbazoles.
EP19827743.6A 2019-02-18 2019-12-20 Composition pour dispositifs électroniques organiques Pending EP3928360A1 (fr)

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WO2023125498A1 (fr) * 2021-12-27 2023-07-06 浙江光昊光电科技有限公司 Composé organique, mélange et composition le comprenant, dispositif électronique organique et utilisations du composé
KR20230103742A (ko) * 2021-12-31 2023-07-07 엘지디스플레이 주식회사 발광 소자 및 이를 이용한 발광 표시 장치
CN118235543A (zh) 2022-06-24 2024-06-21 默克专利有限公司 用于有机电子器件的组合物
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WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
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