WO2013185871A1 - Composés pour dispositifs électroniques - Google Patents

Composés pour dispositifs électroniques Download PDF

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Publication number
WO2013185871A1
WO2013185871A1 PCT/EP2013/001374 EP2013001374W WO2013185871A1 WO 2013185871 A1 WO2013185871 A1 WO 2013185871A1 EP 2013001374 W EP2013001374 W EP 2013001374W WO 2013185871 A1 WO2013185871 A1 WO 2013185871A1
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organic
compounds
identically
differently
occurrence
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PCT/EP2013/001374
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English (en)
Inventor
Arne Buesing
Teresa Mujica-Fernaud
Irina Martynova
Anja Gerhard
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Merck Patent Gmbh
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Priority to DE112013002910.3T priority Critical patent/DE112013002910T5/de
Publication of WO2013185871A1 publication Critical patent/WO2013185871A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/001—Pyrene dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention describes novel compounds and the use thereof in electronic devices.
  • the operating voltage is high, especially in the case of fluorescent OLEDs, and should therefore be reduced further in order to improve the power efficiency.
  • the present invention therefore relates to these compounds and to the use thereof especially in OLEDs.
  • the invention therefore relates to compounds of the formula (1)
  • Ar is at each occurrence, identically or differently, an aromatic or
  • heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 , wherein two Ar may be connected to each other by means of E;
  • E is at each occurrence, identically or differently, a single bond, N(R 1 ), O, S, C(R 1 ) 2 , C(R 1 ) 2 -C(R 1 ) 2 or Si(R ) 2 ;
  • W is at each occurrence, identically or differently, CR 1 or N in the case where W has no substituent X or Y; and W is C in the case where W has a substituent X or Y;
  • H atoms may be replaced by F, CI Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more non- aromatic radicals R 1 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 1 , or a combination of these systems; two or more substituents R 1 here may also form a mono- or polycyclic ring system with one another; R 2 is at each occurrence, identically or differently, H, D, F, or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms; n is at each occurrence, identically or differently, 0 or 1.
  • An electron donating group according to this invention is a monovalent group which is connected via an electron rich heteroatom.
  • an electron donating group according to the invention is a group which has a positive mesomeric effect (+M-effect).
  • electron donating groups according to the invention are -N(Ar) 2l -P(Ar) 2 , -OAr or -SAr.
  • an electron donating group is -N(Ar) 2 , or -P(Ar) 2 .
  • an aryl group or heteroaryl group is taken to mean an aromatic group or heteroaromatic group respectively having a common aromatic electron system, where an aryl group contains 6 to 24 C atoms and a heteroaryl group contains 2 to 24 C atoms and a total of at least 5 aromatic ring atoms.
  • the heteroatoms are preferably selected from N, O and/or S.
  • this can be a single homo- or heterocyclic ring, for example benzene, pyridine, thiophene, etc., or it can be a condensed aromatic ring system in which at least two aromatic or heteroaromatic rings, for example benzene rings, are fused to one another, i.e.
  • aryl or heteroaryl group may be substituted or unsubstituted; any substituents present may likewise form further ring systems.
  • systems such as naphthalene, anthracene, phenanthrene, pyrene, etc., are to be regarded as aryl groups for the purposes of this invention and quinoline, acridine, dibenzothiophene, dibenzofuran, carbazole, etc., are to be regarded as heteroaryl groups for the purposes of this invention, while, for example, biphenyl, fluorene, spirobifluorene, etc., are not aryl groups since separate aromatic electron systems are present here.
  • an aromatic ring system contains 6 to 40 C atoms in the ring system.
  • a hetero- aromatic ring system contains 2 to 40 C atoms and at least one heteroatom in the ring system, with the proviso that the total number of C atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • heteroaromatic ring system is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which, in addition, a plurality of aryl or heteroaryl groups may be interrupted by a short, non-aromatic unit (less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H), such as, for example, a C, N or O atom.
  • a short, non-aromatic unit less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H
  • systems such as 9,9'-spiro- bifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc., are also to be regarded as aromatic ring systems for the purposes of this invention.
  • a Ci- to C 4 o-alkyl group a C 2 - to C 4 o-alkenyl or a C 2 - to C 4 o-alkynyl group, in which individual H atoms or CH 2 groups may also be substituted by the above-mentioned groups, to be the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, tert-pentyl, 2-pentyl, cyclopentyl, n-hexyl, s-hexyl, tert-hexyl, 2-hexyl, 3- hexyl, cyclohexyl, 2-methylpentyl, n-heptyl, 2-hept
  • Ci- to C 40 -alkoxy group is particularly preferably taken to mean methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • a C2- C24-aryl or -heteroaryl group which can be monovalent or divalent depending on the use, may in each case also be substituted by the above-mentioned radicals R 1 and may be linked to the aromatic or heteroaromatic ring system via any desired positions, is taken to mean, in particular, groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, tetra- cene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, di- benzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothio- phene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquino- line,
  • aromatic and heteroaromatic ring systems are taken to mean, in particular, biphenylene, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrene or cis- or trans-indenofluorene, in addition to the above-mentioned aryl and heteroaryl groups.
  • the group W stands for CH the case where W has no substituent Y or X; and W stands for C in the case where W has a substituent Y or X.
  • Preferred embodiments of the invention are the compounds of one of formulae (2) to (3),
  • an aromatic or heteroaromatic ring system is selected from benzene, ortho-, meta- or para-biphenyl, fluorene, naphthalene, anthracene, phenanthrene, benzanthracene, pyridine, pyrene, thiophene, triphenylamine, diphenyl-1 -naphthylamine, diphenyl-2- naphthylamine, phenyldi(1-naphthyl)amine and phenyldi(2-naphthyl)amine, each of which may be substituted by R 1 .
  • the symbol Ar is very particularly preferable for the symbol Ar to be, identically or differently at each occurrence, phenyl, 1- naphthyl or 2-naphthyl, each of which may be substituted by one or two radicals R 1 .
  • R 1 particularly preferably stands for H, F, CN, methyl, tert-butyl, or a monovalent aryl or heteroaryl group having 5 to 14 C atoms, which may be substituted by one or more non-aromatic radicals R 1 , where two aromatic radicals R 1 may form a ring system with one another.
  • Preferred structures of the formula (2) and (3) are the structures of the formulae (4) to (7) depicted below.
  • Preference is furthermore given to compounds of the formulae (1) to (7) in which the symbol X is at each occurrence, identically or differently, selected from the group consisting of F, CI, -P( O)(Ar)2, -SC ⁇ Ar, -SOAr and CN as the electron withdrawing group.
  • X is, identically or differently at each occurrence, F or CN;
  • Y is N(Ar) 2 ; is, identically or differently at each occurrence, an aryl or a heteroaryl group having 5 to 14 C atoms, which may be substituted by one or more radicals R 1 ; and
  • R 1 is defined as above.
  • Examples of preferred compounds of one of the formula (1) to the formula (7) are structures (1) to (50) depicted below.
  • the compounds according to the invention can be prepared by synthetic steps known to the person skilled in the art, such as, for example, bromination, Suzuki coupling, Hartwig-Buchwald coupling, etc.
  • the compounds of the formula (1) to formula (7) can be prepared as shown in Synthesis Schemes 1 and 2.
  • the 1 ,6- and 1 ,8-diaminopyrene derivatives (Scheme 1) can be
  • the 2,7-diaminopyrene derivatives (Scheme 2) can be synthesized according to the following reactions. Pyren-2,7-bis(boronate)ester is obtained in one-step synthesis via an iridium-based catalyst. The bromination of pyren-2,7-bis(boronate)ester using a catalyst, for example CuBr 2 affords 2,7-dibromopyrene. The following Buchwald-Hartwig amination leads to diamino derivatives. The end products are obtained by subsequent bromination, optional separation of isomers and cyanation of the diamino derivatives.
  • the present invention thus further concerns a method of preparing a compound according to the invention, where the method comprises a) performing a bromination of a pyrene derivative,
  • the present invention further concerns a method of preparing a compound according to the invention, where the method comprises
  • the present invention likewise relates to the use of the compounds according to the invention in the corresponding devices and to these devices themselves.
  • the compounds of the formula (1) according to the invention are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs, PLEDs).
  • OLEDs organic electroluminescent devices
  • PLEDs organic electroluminescent devices
  • the compounds are employed in various functions and layers.
  • the invention still furthermore relates to organic electronic devices com- prising at least one compound of the formula (1), in particular organic electroluminescent devices comprising an anode, cathode and at least one emitting layer, characterised in that at least one organic layer, which may be an emitting layer or an another layer, comprises at least one compound of the formula (1).
  • the layer comprising the at least one compound according to the formula (1) is an emitting layer.
  • the organic electroluminescent device may also comprise further layers. These are selected, for example, from in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, electron-blocking layers, exciton-blocking layers, charge-generation layers (IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and/or organic or inorganic p/n transitions.
  • each of these layers does not necessarily have to be present, and the choice of the layers always depends on the compounds used and in particular also on whether it is a fluorescent or phosphorescent electroluminescent device.
  • the organic electroluminescent device may also comprise a plurality of emitting layers, where at least one organic layer comprises at least one compound of the formula (1).
  • These emission layers particularly preferably have in total a plurality of emission maxima between 380 nm and 750 nm, resulting overall in white emission, i.e. various emitting compounds which are able to fluoresce or phosphoresce and emit blue and yellow, orange or red light are used in the emitting layers.
  • Particular preference is given to three-layer systems, i.e. systems having three emitting layers, where at least one of these layers comprises at least one compound of the formula (1) and where the three layers exhibit blue, green and orange or red emis- sion (for the basic structure, see, for example, WO 05/011013).
  • Emitters which have broad-band emission bands and thus exhibit white emission are likewise suitable for white emission.
  • the compounds of the formula (1) prefferably be em- ployed as emitter compounds, preferably in an emitting layer.
  • an emitting layer is a layer which can emit light. If the compounds of the formula (1) are used as emitter, it may be preferred for them to be used in combination with one or more host materials.
  • host material preferably a material having a larger energy gap between HOMO level and LUMO level than the energy gap of the compounds of formula (1) is used.
  • Preferred host materials are selected from the classes of the oligoarylenes (for example 2,2',7,7'-tetraphenylspirobifluorene in accordance with
  • EP 676461 or dinaphthylanthracene
  • the oligoarylenes containing condensed aromatic groups for example DPVBi or spiro-DPVBi in accordance with EP 676461
  • the polypodal metal complexes for example in accordance with
  • the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides, etc. (for example in accordance with WO 05/084081 and WO 05/084082), the atropisomers (for example in accordance with WO 06/048268), the boronic acid derivatives (for example in accordance with WO 06/117052) or the benzanthracenes (for example in accordance with WO 08/145239).
  • Particularly preferred matrix materials are selected from the classes of the oligoarylenes, comprising naphthalene, anthracene, benzanthracene and/or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides.
  • Very particularly preferred matrix materials are selected from the classes of the oligoarylenes, comprising anthracene, benzanthracene, benzophenanthrene and/or pyrene or atropisomers of these compounds, such as anthracenes disclosed in
  • An oligoarylene in the sense of this invention is intended to be taken to mean a compound in which at least three aryl or arylene groups are bonded to one another.
  • the proportion of the emitter of the formula (1) in the emitting layer is between 0.01 vol% and 100%, preferably between 0.1 % and 50 % by volume. It is particularly preferable for the proportion to be between 0.5 % to 20% by volume, very particularly, between 1 % to 10% by volume is preferable.
  • an organic electroluminescent device characterised in that one or more layers are coated by a sublimation process.
  • the materials are vapour-deposited in vacuum sublimation units at an initial pressure of usually below 10 ⁇ 5 mbar, preferably below 10 "6 mbar.
  • the initial pressure it is also possible for the initial pressure to be even lower, for example below 10 ⁇ 7 mbar.
  • an organic electroluminescent device characterised in that one or more layers are coated by the OVPD (organic vapour phase deposition) process or with the aid of carrier-gas sublimation.
  • the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
  • OVJP organic vapour jet printing
  • the materials are applied directly through a nozzle and are thus structured (for example M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
  • an organic electroluminescent device characterised in that one or more layers are produced from solution, such as, for example, by spin coating, or by means of any desired printing proc- ess, such as, for example, screen printing, flexographic printing or offset printing, but particularly preferably LITI (light-induced thermal imaging, thermal transfer printing) or ink-jet printing.
  • Soluble compounds of the formula (1) are necessary for this purpose. High solubility can be achieved by a suitable substitution of the compounds, for example with long-chain alkyl groups or oligophenyl groups such as quaterphenyl groups.
  • the processing of the compounds according to the invention from the liquid phase requires formulations of the compounds according to the invention.
  • These formulations can be, for example, solutions, dispersions or mini-emulsions. It may be preferred to use mixtures of two or more solvents for this purpose.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p- xylene, methyl benzoate, dimethylanisole, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, or mixtures of these solvents.
  • the present invention therefore furthermore relates to a formulation, in particular a solution or dispersion, comprising at least one compound of the formula (1) or the preferred embodiments indicated above and at least one solvent, in particular an organic solvent.
  • a formulation in particular a solution or dispersion
  • solvent in particular an organic solvent.
  • the compounds according to the invention used as emitters in the emission layer exhibit a longer operational lifetime than compounds according to prior art.
  • the starting materials were - unless mentioned otherwise - purchased from ALDRICH or ABCR.
  • the starting point can be, for example, 1 ,6-, 2,7- or 1 ,8-dibromopyrene, Journal of the American Chemical Society, 2004, 126(14), 4540; Angew. Chem. Int. Ed. 2008, 47, 10175, Chemical Reviews DOI: 10.1021/cr100428a, Chem. Comm. 2005, 2172.
  • the intermediate compounds can be prepared as follows. (Intermediates 1 to 19 )
  • the following syntheses are carried out, unless indicated otherwise, in dried solvents under a protective-gas atmosphere.
  • the starting materials can be purchased from ALDRICH.
  • the solid obtained is recrystallised 5x from dioxane/toluene and sublimed in vacuo (10 "5 mbar, 340°C), giving 5.2 g (37%) of 2,7-dicyano- N ) N,N',N'-tetrakis-(2,4-dimethylphenyl)pyrene-1 ,6-diamine as a colourless solid. Purity > 99.9%.
  • the solid obtained is recrystallised 5x from dioxane/toluene and sublimed in vacuo (10 ⁇ 5 mbar, 360°C), giving 5.2 g (37%) of N,N,N ⁇ N'-tetrakis(2,4- dimethylphenyl)-2,7-difluoropyrene-1 ,6-diamine as a colourless solid.
  • Vacuum-evaporated OLEDs according to the invention and OLEDs in accordance with the prior art are produced by a general process in accordance with WO 2004/058911 , which is adapted to the circumstances described here (layer-thickness variation, materials used).
  • the OLEDs have in principle the following layer structure: substrate / optional hole-injection layer (HIL) / hole-transport layer (HTL) / optional interlayer (IL) / electron-blocking layer (EBL) / emission layer (EML) / optional hole-blocking layer (HBL) / electron- transport layer (ETL) / optional electron-injection layer (EIL) and finally a cathode.
  • the cathode is formed by an aluminium layer with a thickness of 100 nm.
  • Table 1 The precise structure of the OLEDs is shown in Table 1.
  • Table 3 The materials required for the production of the OLEDs are shown in Table 3.
  • the materials are applied by thermal vapour deposition in a vacuum chamber.
  • the emission layer here always consists of at least one matrix material (host material) and an emitting dopant (emitter), which is admixed to the matrix material or materials in a certain proportion by volume by co- evaporation.
  • An expression such as H1(95%):SEBV1(5%) here means that the material SEBV1 is present in the layer in a proportion by volume of 5%, H1 is present in a proportion by volume of 95%.
  • the electron- transport layer may also consist of a mixture of two materials.
  • the materials according to the invention can be applied also from solution and lead to OLEDs with a good device performance having a simpler device structure versus vacuum processed devices, c. f. examples Esol vs. Vsol.
  • PLEDs polymer light emitting devices
  • the configuration consists of Substrate /ITO/PEDOT (80 nm) / Interlayer/ Emissionlayer (50nm) / ETL / cathode. Hole injection is done via the Interlayer; in this case HIL-012 (HILsol) of Merck was used.
  • HIL-012 HILsol
  • the dopant according to the invention to be used in the emission layer is dissolved along with the matrix in toluene.
  • Hsol(92%):SEBV1(8%) here means that the material SEBV1 is present in the layer in a proportion by weight of 8%, and Hsol is present in a proportion by weight of 92%.
  • the typical concentration of these solutions is in the range between 16 and 25 g/L, if, like in this case a layer thickness of 50 nm is required via spincoating.
  • the emission layer is spincoated in an inert atmosphere, here argon, and dried for 10 min at a temperature of 120 °C.
  • the aforementioned layers HBL and ETL can be evaporated on top of the EML; the interlayer can be substituted by one or several layers likewise, under the prerequisite that the processing from solution of the downstreaming layers like the EML does not dissolve the interlayer which has been applied before.
  • the OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in per cent) as a function of luminous density, calculated from current-voltage-luminous density characteristic lines (IUL characteristic lines), and the lifetime are determined.
  • the electroluminescence spectra are recorded at a brightness of 1000 cd/m 2 and from it the CIE 1931 x and y colour coordinates are calculated.
  • the lifetime is defined as the time after which the luminous density has dropped from a certain initial luminous density to a certain proportion.
  • the expression LD70 @ 50 mA means that the lifetime given is the time at which the luminous density has dropped to 70% of the initial luminous density when the device is driven at constant current of 50 mA/cm 2 , c.f. table.
  • the values for the lifetime can be converted into a figure for other initial luminous densities with the aid of conversion formulae known to the person skilled in the art.
  • Example V1 to Esol The data for the various OLEDs (examples V1 to Esol) are summarised in Table 2.
  • Examples V1 and Vsol are comparative examples in accordance with the prior art,
  • Examples E1 - Esol show data for OLEDs in which materials according to the invention are employed.
  • SEBV1 shows a shorter lifetime when comparing with compounds according to this invention with similar CIE coordinates, e.g. V1 compared to E3.
  • the emitters of this invention show a narrow emission spectrum, are efficient and show long lifetime. Furthermore they can be used in low doping concentration.
  • inventive devices show deeper blue color coordinates at similar lifetime compared to the reference example V1 (E1 , E2, E4, E5).
  • inventive examples E6 and E7 show green emission at long lifetimes (180 h and 220 h).
  • the inventive emitter When processing from solution, the inventive emitter shows a good lifetime in combination with deep blue colour (Esol).

Abstract

La présente invention concerne des dispositifs électroluminescents organiques comprenant des composés de formule (1), en particulier en tant que matériaux émetteurs de lumière bleue à l'état singulet dans une couche électroluminescente.
PCT/EP2013/001374 2012-06-12 2013-05-08 Composés pour dispositifs électroniques WO2013185871A1 (fr)

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DE112013002910.3T DE112013002910T5 (de) 2012-06-12 2013-05-08 Verbindungen für elektronische Vorrichtungen

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EP12004426.8 2012-06-12
EP12004426 2012-06-12

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