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EP2923391A1 - Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques - Google Patents

Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques

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Publication number
EP2923391A1
EP2923391A1 EP13783858.7A EP13783858A EP2923391A1 EP 2923391 A1 EP2923391 A1 EP 2923391A1 EP 13783858 A EP13783858 A EP 13783858A EP 2923391 A1 EP2923391 A1 EP 2923391A1
Authority
EP
European Patent Office
Prior art keywords
organic
materials
formulation according
solvent
formulation
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.)
Ceased
Application number
EP13783858.7A
Other languages
German (de)
English (en)
Inventor
Herwig Buchholz
Thomas Eberle
Junyou Pan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to EP13783858.7A priority Critical patent/EP2923391A1/fr
Publication of EP2923391A1 publication Critical patent/EP2923391A1/fr
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
    • 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
    • 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
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
    • 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 relates to a formulation capable of producing electronic devices with improved performance in terms of operating voltage, efficiency and life. Likewise, the present invention relates to a process for the preparation of a formulation according to the invention, and to a process for the production of electronic devices using the formulation according to the invention. Furthermore, the present invention also relates to an electronic device which has been produced by the method according to the invention.
  • OLEDs organic photovoltaic cells
  • OLEDs organic thin film transistors
  • TFTs organic thin film transistors
  • Formulation or solution containing the organic functional compounds or organic semiconductor materials comprise at least one solvent.
  • the formulation and also the subsequently printed layer are exposed to the ambient atmosphere for a short time window (t1).
  • This time window depends on the printing method and may vary for a few minutes.
  • oxygen and / or ozone may diffuse from the environment into the formulation or into the layer, which is detrimental to the organic functional materials and thus detrimental to the electronic device. It is therefore desirable to delay or even prevent the diffusion of oxygen and / or ozone into the formulation or into the layer.
  • HTM hole transport materials
  • HIM hole injection materials
  • ETM electron transport materials
  • Electron injection materials EIM
  • HBM electron-blocking materials
  • EBM electron-blocking materials
  • ExBM exciton-blocking materials
  • light-emitting materials host materials, organic metal complexes, organic dyes, and combinations thereof;
  • a "nanocrystal” is understood to mean a substance whose size is in the nanometer range, ie a nanoparticle having a largely crystalline structure
  • the size of the nanocrystals is preferably in the range from 1 to 300 nm.
  • the nanocrystals are preferably semiconducting nanocrystals Suitable semiconductor materials for the nanocrystal are selected from
  • Group II-VI elements such as CdSe, CdS, CdTe, ZnSe, ZnO, ZnS, ZnTe, HgS, HgSe, HgTe, and alloys thereof, e.g. CdZnSe; Group III-V, such as InAs, InP, GaAs, GaP, InN, GaN, InSb, GaSb, AIP, AlAs, AlSb, and alloys thereof, such as InAsP, CdSeTe, ZnCdSe, InGaAs, Group IV-VI, such as PbSe, PbTe, and PbS and
  • Group II-VI such as InSe, InTe, InS, GaSe and
  • Alloys thereof such as InGaSe, InSeS; Group IV semiconductors such as Si and Ge alloys thereof, and combinations thereof.
  • the nanocrystal is a
  • Quantum dot Quantum dot
  • QDs quantum dots
  • a nanoscopic structure made of a semiconductor material such as InGaAs, CdSe, ZnO or GalnP / InP their mobility in all three spatial directions are so limited that their energy can no longer be continuous, but only discrete values.
  • Quantum dots behave in a similar way to atoms, but their shape, size, or number of electrons can be affected. Typically, their own atomic order is about 10 4 atoms. Due to the limited size of the QDs, especially the core-shell QDs, they show unique optical properties compared to the corresponding bulk materials.
  • the emission spectrum is defined by a simple Gaussian peak corresponding to the band edge transition. The location of the emission peak is determined by the particle size as a direct result of the quantum confinement effect. Other electronic and optical properties are used by Al. L. Efros and M. Rosen in Annu. Rev. Mater. Be. 2000. 30: 475-521.
  • the QD of the invention has a "core / shell” or core / shell structure as reported by X. Peng, et al., J. Am. Chem. Soc., Voll 19: 7019-7029 (1997).
  • quantum dots are substantially mono-disperse in size.
  • a QD has at least one region or characteristic dimension with a dimension of less than about 300 nm and greater than about 1 nm.
  • the term mono-dispersive means that the size distribution is within +/- 10% of the stated value. So is z.
  • the QD comprises semiconducting materials selected from the group II-VI semiconductors, their alloys, and core / shell structures thereof.
  • Embodiments are group II-VI semiconductors CdSe, CdS, CdTe, ZnSe, ZnS, ZnTe, alloys thereof, combinations thereof and core / shell, core multi-layered layer structures thereof.
  • nanorods in the present invention a lengthened particle having a size in the range of
  • Nanometers The ratio of the length to the width of the particle is preferably in the range from 2 to 20.
  • nanorods are colloidal.
  • the nanocrystals comprise the ligands that are conjugated, cooperated or associated on their surface.
  • Suitable ligands for this are well known in the art. Examples thereof are disclosed, for example, in US 10 / 656,910 and US 60 / 578,236. The use of such ligands increases the solubility or miscibility of the QDs in various solvents and matrix materials. Further preferred
  • Ligands are those with a "head-body-tail” structure, as in US 2007/0034833 A1 discloses, wherein further preferably the "body” has an electron or hole transport function, as in
  • these aryiamines and heterocycles lead to a HOMO in the polymer of greater than -5.8 eV (at vacuum level), more preferably greater than -5.5 eV.
  • ETMs and EIMs are materials that have electron-transporting or electron-injecting properties.
  • HBMs are materials that block the formation of holes or prevent their transport. HBMs are often included in devices with phosphorescent emitters between the light emitting layer and the electron transport layer.
  • Irppz (Ir (ppz) 3 fac-Tris (1-phenylpyrazolato-N, C 2 ) iridium (III)) is also used for this purpose.
  • Suitable HBMs are still available
  • WO 00/70655 A2 WO 01/41512 and WO 01/93642 A1.
  • triazine derivatives spiro-oligophenylenes and ketones or phosphine oxides.
  • EBMs are materials that block or block the transport of electrons.
  • ExBMs are materials that prevent or block the transport or formation of excitons.
  • transition metal complexes such as Ir (ppz) 3 (US 2003-0175553) and AIQ 3 are advantageously used.
  • Carbazole compounds e.g., TCTA
  • heterocycles e.g., BCP
  • tetraazasilane derivatives e.g., TCTA
  • a light-emitting material is a material that preferably emits light in the visible region.
  • the light-emitting material preferably has an emission maximum between 380 nm and 750 nm.
  • the light-emitting material is preferably a phosphorescent or fluorescent emitter compound.
  • a fluorescent emitter compound in the sense of this invention is a compound which exhibits luminescence from an excited singlet state at room temperature.
  • all luminescent compounds which have no Heavy atoms, ie no atoms with an atomic number greater than 36, are considered to be fluorescent compounds.
  • Preferred emitter emitter compounds are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines.
  • a monostyrylamine is meant a compound containing a substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
  • a distyrylamine is understood as meaning a compound which contains two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tristyrylamine is understood to mean a compound which has three
  • tetrastyrylamine is meant a compound which is four substituted or unsubstituted
  • the styryl groups are particularly preferred stilbenes, which may also be further substituted.
  • Corresponding phosphines and ethers are defined in analogy to the amines.
  • An arylamine or an aromatic amine in the context of this invention is understood as meaning 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 fused ring system, preferably having at least 14 aromatic ring atoms.
  • Preferred examples of these are aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic
  • aromatic anthracenamine is understood as meaning a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • aromatic anthracenediamine is meant a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 2,6 or 9,10 position.
  • Aromatic Pyrenamine, Pyrendiamine, Chrysenamine 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 emitter compounds are selected from indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines.
  • emitter emitter compounds are selected from derivatives of naphthalene, anthracene, tetracene, benzanthracene, benzphenanthrene, fluorene, fluoranthene, periflanthene, indenoperylene, phenanthrene, perylene, pyrene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene , Spirofluorene, rubrene, coumarin, pyran, oxazole, benzoxazole, benzothiazole, benzimidazole,
  • Position substituted anthracenes such as e.g. 9,10-diphenylanthracene and 9, 0-bis (phenylethynyl) anthracene.
  • 1,4-bis (9'-ethynylanthracenyl) benzene is a preferred dopant.
  • derivatives of rubrene, coumarin, rhodamine, quinacridone, e.g. DMQA ( ⁇ , ⁇ '-dimethylquinacridone), dicyano-methylene pyran, e.g.
  • DCM 4- (dicyanoethylene) -6- (4-dimethyl-aminostyryl-2-methyl) -4H-pyran), thiopyran, polymethine, pyrylium and thiapyrylium salts, periflanthene and indenoperylene.
  • Blue fluorescence emitters are preferably polyaromatics, e.g. 9,10-di (2-naphthylanthracene) and other anthracene derivatives, derivatives of
  • Tetracene, xanthene, perylene e.g. 2,5,8,11-tetra-f-butyl-perylene,
  • Phenylene e.g. 4,4 '- (bis (9-ethyl-3-carbazovinylene) -1, 1'-biphenyl, fluorene, fluoranthene, arylpyrene, arylenevinylene, bis (azinyl) imine-boron
  • a phosphorescent emitter compound is generally understood to mean a compound which exhibits luminescence from an excited state with a higher spin multiplicity, ie a spin state> 1, for example from an excited triplet state (triplet emitter), from an MLCT mixed state or a quintet Condition (quintet emitter).
  • Particularly suitable as phosphorescent emitter compounds are compounds which emit light, preferably in the visible range, with suitable excitation and also contain at least one atom of atomic numbers> 38 and ⁇ 84, particularly preferably> 56 and ⁇ 80.
  • phosphorescence emitter compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium, platinum or copper.
  • Examples of the emitters described above can be found in the applications WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244.
  • organic metal complexes metal-ligand coordination compounds wherein the ligand is an organic compound.
  • metal complexes includes all compounds which are known to a person skilled in the art in organic electronic compounds
  • Particularly preferred organic electronic devices contain as phosphorescent emitter compounds at least one metal complex of the formulas (1) to (4), 013 003269
  • DCy is the same or different at each occurrence, a cyclic one
  • CCy is the same or different at each occurrence a cyclic
  • A is the same or different at each occurrence as a mononionic, bidentate chelating ligand, preferably a diketonate ligand;
  • R 1 is the same or different at each occurrence
  • Examples of the emitters described above can be found in applications WO 2000/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244,
  • WO 2010/102709 are taken.
  • all phosphorescent complexes used in the prior art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art may use other phosphorescent complexes without inventive step.
  • a host material is preferably a material used as a matrix for a light-emitting compound.
  • Suitable host materials for fluorescent emitters are materials of various substance classes.
  • Particularly preferred host materials for fluorescent emitters are selected from the classes of oligoarylenes containing anthracene, benzanthracene and / or pyrene or atropisomers of these compounds.
  • an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.
  • Other preferred compounds are
  • TNB 4,4'-bis [N- (1-naphthyl) -N- (2-naphthyl) - , amino] biphenyl.
  • Metal oxinoid complexes such as LiQ or AlQ 3 can be used as co-hosts.
  • CBP ⁇ , ⁇ -biscarbazolylbiphenyl
  • carbazole derivatives azacarbazoles, ketones, phosphine oxides, sulfoxides and sulfones, oligophenylenes, aromatic amines, bipolar matrix materials, silanes, 9,9- Diarylfluorene derivatives, azaboroles or boronic esters, triazine derivatives, indolocarbazole derivatives, indenocarbazole derivatives, diazaphospholene derivatives, triazole derivatives, oxazoles and oxazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, distyrylpyrazine derivatives, thiopyranedioxide derivatives Derivatives, phenylenediamine derivatives, tertiary aromatic amines, sty
  • Formulation are ketones, phosphine oxides, sulfoxides and sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B. CBP (N, N-bis-carbazolylbiphenyl), m-CBP or in WO 2005/039246,
  • bipolar matrix materials e.g. B. according to
  • WO 2010/054730 triazine derivatives, z. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, for. B. according to EP 652273 or WO 2009/062578, Dibenzofuranderivate, z. B. according to WO 2009/148015, or bridged carbazole derivatives, for. B. according to
  • a plurality of different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material.
  • a preferred combination is, for example, the use of an aromatic ketone, a triazine derivative or a phosphine oxide derivative with a triarylamine derivative or a carbazole derivative or a fluorene derivative as a mixed matrix for the invention
  • Metal complex Also preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material, which is not or not significantly involved in charge transport, such. As described in WO 2010/108579.
  • “Dyes” are compounds that absorb part of the visible white light, and color absorption is usually based on many conjugated double bonds and aromatic bases in the dyeing process Energy again and indeed either by radiation of a different wavelength, through
  • the preferred metal complex dye is a polypyridyl complex of transition metals, preferably ruthenium, osmium and copper.
  • the metal complex dye will have the general structure ML 2 (X) 2 wherein L is preferably selected from a 2,2'-bipyridyl-4,4'-dicarboxylic acid, M is a transition metal preferably from Ru, Os, Fe, V and Cu are selected, and X is selected from the groups comprising a halide, cyanide, thiocyanate, acetylacetonate, thiacarbamate or water
  • Substituent is selected.
  • metal complex dyes are disclosed, for example, in J. Phys. Chem. C (2009), 113, 2966-2973, US 2009/000658, WO 2009/107100, WO 2009/098643, US 6245988, WO 2010/055471, JP 2010084003, EP 1622178, WO 9850393,
  • the functional organic material in the formulation of the invention is a hole transporting material, a light emitting material, a host material, an electron transporting material, or a combination thereof. Particularly preferred is a combination of a light-emitting material and a host material.
  • the formulation of the invention may be in the form of a solution, emulsion or dispersion.
  • An emulsion is a finely divided mixture of two normally immiscible liquids without visible segregation.
  • the emulsion may also be a mini- or nano-emulsion, which is understood to mean emulsions that are thermodynamically stable. These emulsions are optically transparent and form without the otherwise required for the production of emulsions high energy input.
  • co-surfactants or co-solvents are used to prepare a microemulsion or nanoemulsion.
  • Emulsions of two Solvents are used in particular when the substances to be dissolved have a better solubility therein.
  • a dispersion is understood to mean a heterogeneous mixture of at least two substances which do not dissolve or barely dissolve or chemically bond with one another. As a rule, these are colloids.
  • the nanocrystal or the functional organic material (dispersed phase) is distributed as finely as possible in the solvent (dispersion medium).
  • the inert gas used to supersaturate the solvent of the formulation of the invention is preferably N 2) a noble gas, CO 2 or a combination thereof.
  • noble gas is preferably
  • the content of inorganic nonmetallic impurities in the solvent is less than 500 ppm, more preferably 300 ppm, even more preferably 200 ppm, and most preferably 100 ppm.
  • Inorganic, non-metallic impurities are understood as meaning all inorganic compounds which contain no metals. This means in particular halogens or halides according to the invention.
  • the content of metallic impurities in the solvent is preferably less than 500 ppm, more preferably 300 ppm, even more preferably 200 ppm, and most preferably 100 ppm, wherein a metal atom is to be counted as one particle.
  • the content of O 2 and H 2 O taken together in the solvent is preferably less than 500 ppm, more preferably less than 300 ppm, even more preferably less than 100 ppm, more preferably less than 50 ppm, and most preferably less than 20 ppm.
  • the purity of the solvent is preferably at least 99.8% by weight, more preferably 99.9% by weight.
  • the purity of the solvent can be determined by HPLC-MS analysis.
  • the at least one solvent used in the formulation according to the invention is preferably from the group
  • aromatic or heteroaromatic hydrocarbon compounds selected from optionally substituted aromatic or heteroaromatic hydrocarbon compounds, dialkylformamides, aliphatic linear, branched or heteroaliphatic cyclic hydrocarbons and mixtures thereof.
  • Suitable organic solvents may be dichloromethane, trichloromethane, monochlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, mesitylene, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 1, 1, 1-trichloroethane, 1, 1, 2,2-tetrachloroethane, ethyl acetate, n butyl acetate, dimethylacetamide, tetralin, decalin, indane, cyclohexanone, dimethylformamide (DMF), dimethylsulfoxide (DMSO), propylene carbonate, dichloromethane (DCM), tetrahydrofuran (THF), ethyl acetate, acetone,
  • the optionally substituted aromatic or heteroaromatic hydrocarbon compound is preferably selected from the group consisting of toluene, xylene, anisole and other phenol ethers, pyridine, pyrazine, N, N-di-Gi-2-alkylaniline, chlorobenzene, dichlorobenzene, trichlorobenzene, and derivatives thereof consists.
  • Dialkylformamides are compounds which are substituted on the amide nitrogen with two alkyl groups, methyl and ethyl being preferred as alkyl groups. Examples are dimethylformamide (DMF), N-methylpyrrolidone (NMP), dimethylacetamide (DMAC) and their
  • aliphatic linear, branched or cyclic hydrocarbons the following are preferred: cyclohexanone, propylene carbonate, dichloromethane (DCM), tetrahydrofuran (THF), ethyl acetate, acetone, acetonitrile, formic acid, n-butanol, isopropanol, n-propano, Acetic acid, ethanol, methanol, pyrrolidones and their derivatives.
  • the solvent used in the formulation according to the invention is preferably freed from impurities as far as possible before use. This can be done by recrystallization at low
  • the liberation of the solvent from dissolved gaseous molecules such as oxygen or water is preferably conducted by passing inert gas through the solvent. In this way, it also leads to saturation or supersaturation of the solvent with the inert gas.
  • the inert gases mentioned above are preferably used.
  • “supersaturated” is understood to mean that at least 90% of the dissolved gases, more preferably at least 95%, and most preferably at least 99%, are inert gases in the solvent, and preferably also at least 95% of the gas uptake capacity of inert gas in the solvent. more preferably at least 99% is exhausted.
  • the saturated or supersaturated solvents or formulation can be produced under inert gas atmosphere with high pressure, such as by pressing.
  • HS-GC headspace gas chromatography
  • GC gas chromatography
  • the sample is here optionally vaporized via an injector and applied to a chromatographic separation column.
  • a chromatographic separation column For the direct introduction of the sample into the gas chromatograph, slight volatility and, at the temperatures prevailing in the GC, stability of the sample components
  • the chromatographic column represents the so-called.
  • the mobile phase is provided by an inert gas flowing through the column.
  • the output of the column is connected to a suitable detector which registers the substances and, via calibration with appropriate standards
  • Quantification of the analytes in the sample allows.
  • An easy way to separate volatile components from the non-volatile or difficult-to-volatile matrix is the so-called headspace or steam room technique.
  • the sample is in an analysis vessel which is closed by a septum.
  • a volatiles equilibrium is established between the gas space and the sample, which depends on the type and concentration of the analytes.
  • a gas-tight syringe becomes an aliquot of the vapor space above the sample
  • Calibration standards can be achieved by saturating the sample with the gas to be determined and by completely degassing the sample Produce solutions under controlled conditions. The knowledge of the solubility under given conditions must be given in this approach.
  • the signal obtained for the sample to be analyzed is compared with the signals of the calibration standards described above. Another possibility arises when it is assumed that at elevated temperatures, the solubility of the gases in the liquid to be analyzed approaches zero. In this case the sample is brought into thermal equilibrium at elevated temperatures (eg 80-120 ° C) and the gas space is analyzed.
  • the signal obtained can be compared with the signal of a known gas mixture. Ideally, here is a mixture of the analyte gas in for those expected in the sample
  • the present invention also relates to a process for the preparation of a formulation according to the invention in which, in a first step, the nanocrystal or the functional organic material is dissolved in a solvent and degassed in a second step with the inert gas. Between these steps is preferably stirred until a clear solution, mini- or nano-emulsion is obtained. In order to free the solution of any undissolved impurities, it can be filtered through a filter before or after the fumigation.
  • the present invention also relates to a process for producing an organic electronic device using a formulation of the invention.
  • Formulations are preferably used to thin
  • Layers for example by surface coating method (eg spin-coating) or by printing processes (eg ink jet printing).
  • the formulation according to the invention are particularly suitable for the production of films or coatings, in particular for the production of structured coatings, for example by thermal or light-induced crosslinking of crosslinkable groups.
  • the present invention also relates to an organic electronic device produced by the method of the invention.
  • the organic electronic device is preferably made of
  • OLED organic or polymeric organic electroluminescent devices
  • OFET organic field effect transistors
  • OIC organic integrated circuits
  • OFT organic thin film transistors
  • OLET organic light emitting transistors
  • OSC organic solar cells
  • O-lasers organic laser diodes
  • OFQD organic field quench devices
  • LECs organic plasmon-emitting devices
  • OCV organic photovoltaic
  • OPC organic photoreceptor
  • the electronic device may have further layers, for example an intermediate layer between the anode and a light-emitting layer.
  • the electronic device according to the invention preferably contains an anode and a cathode in addition to the layer which has been produced from the formulation according to the invention.
  • the cathode may be composed of various materials as used in the prior art. Examples of particularly suitable cathode materials are generally low work function metals, followed by a layer of aluminum or a layer of silver. Examples include cesium, barium, calcium, ytterbium and samarium, each followed by a layer of aluminum or silver. Also suitable is an alloy of magnesium and silver.
  • the anode high workfunction materials are preferred.
  • the anode has a potential greater than 4.5 eV. Vacuum up.
  • metals with high redox potential are suitable, such as Ag, Pt or Au.
  • metal / metal oxide electrons z. B. AI / Ni / ⁇ , AI / PtO x
  • at least one of the electrodes must be transparent to either the
  • Irradiation of the organic material or the extraction of light (OLED / PLED, O-LASER) to allow.
  • a preferred construction uses a transparent anode.
  • Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive doped polymers.
  • Embodiments of the present invention are to be considered. For these features, independent protection may be desired in addition to or as an alternative to any presently claimed invention.
  • the teaching on technical action disclosed with the present invention can be abstracted and combined with other examples. The invention is explained in more detail by the following examples without wishing to restrict them thereby.
  • H1 and H2 are host materials and were synthesized according to WO 2009/124627 and DE 102008064200.2.
  • TR1 is a red-phosphorescent emitter, which was synthesized according to DE 102009041414.2.
  • EML Emit Layers
  • compositions are dissolved in 10 mL of toluene (purity 99.90%), using toluene of purity 99.50% for solution 6 and stirring until the solution is clear.
  • the solution is filtered using a filter Millipore Millex LS, hydrophobicity PTFE 5.0 ⁇ .
  • the solutions are then degassed with various noble gas.
  • the resulting OLEDs are characterized according to standard methods. The following properties are measured: UIL characteristic, electroluminescence spectrum, color coordinates, efficiency, operating T EP2013 / 003269
  • the organic electroluminescent devices with formulations according to the invention show markedly improved performance in terms of operating voltage, efficiency and service life.
  • OLEDs 2 to 4 also show a comparable performance with OLED 5, in which the EML was applied in the glove box. It may be because the noble gas in the solvent of the formulation used prevents the diffusion of oxygen into the EML.
  • OLED 6 and OLED 7 show that a further improvement in performance can be achieved by using a higher purity solvent.
  • Residence time in air or the use of other co-matrices or other emitters in the same or a different concentration can be achieved.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une formulation permettant de fabriquer des dispositifs électroniques présentant un meilleur rendement en ce qui concerne la tension d'utilisation, l'efficacité et la durée de vie. La présente invention concerne également un procédé pour la préparation d'une formulation selon l'invention et un procédé pour la fabrication de dispositifs électroniques à l'aide de la formulation selon l'invention. De plus, la présente invention concerne également un dispositif électronique qui a été fabriqué selon le procédé selon l'invention.
EP13783858.7A 2012-11-20 2013-10-30 Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques Ceased EP2923391A1 (fr)

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EP12007813 2012-11-20
PCT/EP2013/003269 WO2014079532A1 (fr) 2012-11-20 2013-10-30 Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques
EP13783858.7A EP2923391A1 (fr) 2012-11-20 2013-10-30 Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques

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JP6407877B2 (ja) 2018-10-17
US9695354B2 (en) 2017-07-04
CN104756273B (zh) 2017-10-24
CN104756273A (zh) 2015-07-01
JP2016501430A (ja) 2016-01-18
US20150299562A1 (en) 2015-10-22
KR102105810B1 (ko) 2020-04-29
KR20150087378A (ko) 2015-07-29
WO2014079532A1 (fr) 2014-05-30

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