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WO2025032039A1 - Procédé de préparation d'un dispositif électronique - Google Patents

Procédé de préparation d'un dispositif électronique Download PDF

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Publication number
WO2025032039A1
WO2025032039A1 PCT/EP2024/072131 EP2024072131W WO2025032039A1 WO 2025032039 A1 WO2025032039 A1 WO 2025032039A1 EP 2024072131 W EP2024072131 W EP 2024072131W WO 2025032039 A1 WO2025032039 A1 WO 2025032039A1
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Prior art keywords
organic
process according
organic solvent
layer
materials
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PCT/EP2024/072131
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English (en)
Inventor
Manuel HAMBURGER
Hsin-Rong Tseng
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Merck Patent Gmbh
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Publication date
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Publication of WO2025032039A1 publication Critical patent/WO2025032039A1/fr

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Classifications

    • 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
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
    • 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
    • H10K50/15—Hole transporting layers
    • 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
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • 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

Definitions

  • the present invention relates to a process for the preparation of an electronic device such as an organic electroluminescent device (OLED), wherein two adjacent functional layers having an interface are formed from solution in a kinetically controlled manner.
  • OLED organic electroluminescent device
  • the process is particularly suitable for a fast and efficient production of electronic devices by printing or coating processes.
  • the present invention furthermore relates to an electronic device which is obtainable by said process.
  • OLEDs have been fabricated by vacuum deposition for small molecule materials, and by spin-coating or dip coating for polymeric materials. More recently, other techniques such as inkjet printing have been used to directly deposit organic thin film layers in the fabrication of OLEDs. Such techniques were found to be cost efficient and suitable for scale-up.
  • One of the main challenges in multi-layer printing is to identify and adjust the respective printing parameters in order to obtain a homogeneous deposition of inks on the substrate thereby creating well-defined and uniform functional layers which give good device performance. In multilayer printing processes, there is always the risk of a detachment, partial dissolution, redissolution or other impairment of the existing functional layers on the substrate on which a new functional layer is printed.
  • Liaptsis et al. describe solution processed organic double light-emitting layer diodes which are based on cross-linkable small molecular systems (Angew. Chem. Int. Ed. 2013, 52, 9563-9567). The synthesis and characterization of new-crosslinkable green-emitting lr IH complexes and spirobifluorene as host materials are described herein.
  • an OLED is formed from small molecule organic semiconductor materials which are deposited from liquid compositions (inkjet fluids) by inkjet printing to from functional layers which may be cross-linked.
  • N-methylpyrrolidone (NMP), ethyl benzoate, benzyl acetate and 1-tetralone are used as solvents in the inkjet fluids.
  • NMP N-methylpyrrolidone
  • ethyl benzoate ethyl benzoate
  • benzyl acetate and 1-tetralone are used as solvents in the inkjet fluids.
  • the OLED manufacturing process in US 2012/0205637 A1 is as follows: an hole injection layer (HIL) is made by inkjet printing an HIL inkjet fluid onto a substrate, followed by vacuum drying for 10 minutes at room temperature.
  • HIL hole injection layer
  • a hole transport layer is made by inkjet printing an HTL inkjet fluid onto the cross-linked HIL, followed by vacuum drying for 10 minutes at room temperature.
  • the resulting organic layer is then subjected to hot plate baking at 200°C for 30 minutes to remove more solvent and to cross-link the HTL material.
  • An emissive layer is made by inkjet printing of an EML inkjet fluid onto the cross-linked HTL, followed by vacuum drying for 10 minutes at room temperature and then followed by baking at 100°C for 60 minutes.
  • a hole blocking layer HBL
  • ETL electron transport layer
  • electron injection layer containing LiF and an aluminum electrode (cathode) were sequentially vacuum deposited in a conventional fashion.
  • multi-layer printing techniques were developed which rely on the so-called orthogonal solvent concept.
  • a first organic compound is deposited from solution containing a first solvent.
  • a second organic compound is deposited from solution containing a second solvent on the first organic compound layer and the dried.
  • the first organic compound is soluble in the first solvent and the second organic compound is soluble in the second solvent.
  • the second solvent is selected such that the first organic compound is not soluble therein.
  • US 2005/0191927 A1 relates to a process for forming an organic electronic device comprising at least two organic layers, wherein said process comprises (a) applying a first organic layer comprising a first organic material by a method selected from vapor deposition and liquid deposition from a first organic liquid medium; and (b) applying a second organic layer comprising a photoactive compound directly over at least a portion of the first organic layer by liquid deposition from a second organic liquid medium, wherein the first organic material is sparingly soluble in the second organic liquid medium.
  • A.M. Gaikwad et al. describe how orthogonal solvents may be determined for solution processed organic semiconductors used in organic field effect transistors (OFETs) (Org. Electr. 2016, 30, 18-29).
  • orthogonal solvents to prepare successive solution-processed layers in electronic devices is usually achieved by choosing a solvent pair which has a strong difference in polarity (e.g. a non-polar organic solvent and an aqueous solvent) or chemical composition (e.g. a hydrocarbon solvent and a highly fluorinated solvent).
  • polarity e.g. a non-polar organic solvent and an aqueous solvent
  • chemical composition e.g. a hydrocarbon solvent and a highly fluorinated solvent.
  • This approach necessitates a suitable functionalization of the material which is solution-processed to form the layer, in the first case by attaching polar substituents for the material to be processed from the polar solvent, in the latter case a substantial amount of fluorinated side chains need to be included.
  • One object of the present invention is to provide a process for the preparation of an electronic device which allows an efficient and controlled deposition of organic functional materials to form uniform functional layers having good layer properties and performance. It is one object of the present invention to prevent detachment, partial dissolution, redissolution or other impairment of a first functional layer on which a second functional layer is printed on top.
  • a further object of the present invention is to provide a process for the preparation of an electronic device which contains fewer process steps as compared to the prior art and is therefore easier, faster and more cost efficient.
  • Another benefit is the reduction of restraints to material design and synthesis: For the material forming the first layer, no chemical means to reduce its solubility after film formation needs to be included in its molecular structure. Therefore, the scope of potentially useful materials becomes wider.
  • the present invention relates to a process for the preparation of an electronic device comprising a first functional layer A and a second functional layer B which form an interface, wheren the process comprises the following steps: a1 ) depositing a first solution containing at least an organic functional material A and at least a first organic solvent on a support; a2) drying said first solution and optionally annealing said organic functional material A to obtain a first functional layer A; b) depositing a second solution containing at least a second organic solvent on the first functional layer A; c1 ) depositing a third solution containing at least an organic functional material B and at least a third organic solvent into the second solution; and c2) drying said second and third solution and optionally annealing said organic functional material B to obtain a second functional layer B; wherein the absolute solubility of the organic functional material A in the second organic solvent is in the range from 0.1 to 200 g/L, preferably from 5.0 to 200 g/L, and more preferably from 5.1 to 200 g/L,
  • the inventors have surprisingly found that the above-mentioned process for the preparation of an electronic device allows an efficient and controlled deposition of organic functional materials to form uniform functional layers having good layer properties and performance.
  • the preparation process according to the present invention allows the formation of well- defined and uniform interfaces without defects between two adjacent functional layers. This is due to a kinetic control which prevents detachment, partial dissolution, redissolution or other impairment of the first functional layer on which the second functional layer is printed on top.
  • the above-mentioned process for the preparation of an electronic device contains fewer process steps as compared to the prior art and is therefore easier, faster and more cost efficient. Beyond that, OLEDs which are produced by said preparation process show improved device performance such as improved lifetime. In addition there is no need for a cross-linking of the first organic functional material or other treatment to prevent solubility of the first functional layer on which the second organic functional material is deposited to form the second functional layer.
  • Figure 1 shows the print pattern as used in the layer damage test of the working examples.
  • Figure 2 shows a picture of a resulting drop achieved in the layer damage test.
  • Figure 3 is a schematic view, which describes how the picture in Figure 2 is taken.
  • Figure 4 shows the surface profile of the resulting layer in the layer damage test before solvent exposure and after exposure with the solvent 1 -ethylnaphthalene (ENA) and Menthyl isovalerate (Menthoval), respectively.
  • the present invention relates to a process for the preparation of an electronic device comprising a first functional layer A and a second functional layer B which form an interface, wherein the process comprises the following steps: a1 ) depositing a first solution containing at least an organic functional material A and at least a first organic solvent on a support; a2) drying said first solution and optionally annealing said organic functional material A to obtain a first functional layer A; b) depositing a second solution containing at least a second organic solvent on the first functional layer A; c1 ) depositing a third solution containing at least an organic functional material B and at least a third organic solvent into the second solution; and c2) drying said second and third solution and optionally annealing said organic functional material B to obtain a second functional layer B; wherein the absolute solubility of the organic functional material A in the second organic solvent is in the range from 0.1 to 200 g/L, preferably from 5.0 to 200 g/L, and more preferably from 5.1 to 200 g/L, at
  • the absolute solubility of the organic functional material B in the third organic solvent is > 5.0 g/L, preferably > 5.1 g/L, more preferably > 5.2 g/L, still more preferably > 5.3 g/L, still more preferably > 5.4 g/L, still more preferably > 5.5 g/L, and most preferably > 6.0 g/L, at 25°C.
  • the absolute solubility of the organic functional material B in the second organic solvent is ⁇ 1 ,0 g/l, preferably ⁇ 0.1 g/l, and more preferably ⁇ 0.01 g/l.
  • the absolute solubility of the organic functional material B in the third solvent is determined according to the following procedure which corresponds to ISO 7579:2009.
  • the test solution shall follow the Beer-Lambert law and shall be stable enough to allow repeatable measurements. If the maximum of the absorption peak is not stable during several repeated measurements, another, more stable, peak shall be selected for the calculation or an assessment of the whole spectrum shall be considered.
  • the calibration solution shall follow the Beer-Lambert law. If a 2 cm spectrophotometer cell is used, a concentration of about 0.15 g/l for yellow dyestuffs (low absorption) and about 0.02 g/l for blue dyestuffs (high absorption) is normally suitable. Weigh exactly 100.0 mg of dyestuff into a weighing bottle and transfer it to a 100 ml volumetric flask taking care that none is lost. Add 60 ml of solvent and dissolve the dyestuff in an ultrasonic bath Cool down, if necessary, to room temperature, make up to the mark with solvent and shake well. The dyestuff concentration in the solution thus prepared is exactly 1 .0 g/l and it now has to be diluted so that it follows the Beer-Lambert law (e.g. to 0.2 g/l or 0.02 g/l).
  • test solutions as specified and dilute each to a concentration comparable to that of the calibration solution. For example, to obtain a concentration of 0.02 g/l, two dilution steps are required: a) 1 g/l; b) 0.02 g/l. The amount weighed out shall therefore be over 1 g. The use of a 10 mm cell can reduce the number of dilution steps necessary.
  • D is the relative amount of dyestuff in the test solution
  • c c is the concentration of the dyestuff in the calibration solution, in g/l
  • Ac is the absorbance of the calibration solution at the peak maximum chosen
  • c s is the final concentration of the supernatant liquid in the diluted test solution in g/l.
  • the present invention furthermore relates to an OLED which is obtainable by said process for preparation.
  • the dissolution rate of the organic functional material A in the second organic solvent is ⁇ 0.116 g/(L min) at 25°C.
  • the dissolution rate of the organic functional material A in the second organic solvent is determined according to the following procedure:
  • the organic functional material A is weighed into a transparent glass flask.
  • the second organic solvent is then added to the solid mixture at once, the amount is calculated to reach a final concentration of 7 g/l.
  • the mixture is stirred at 600 rpm using a magnetic stirrer at room temperature (25°C) until complete dissolution, which is judged by visual inspection of the mixture.
  • Towards the end of the dissolution test the mixture is additionally be examined under illumination perpendicular to the line of sight to help identify undissolved particles.
  • the “dissolution time” toiss is measured using a chronometer, and quantifies the time between addition of the solvent and beginning of stirring until to the disappearance of the last pieces of material into solution.
  • the dissolution rate is determined by dividing 7 g/l by the time until full dissolution was obtained (the “dissolution time”).
  • the second organic solvent has a layer damage rate (LDR) with respect to the first functional layer of less than 0.066 nm/sec at 25°C.
  • the layer damage rate (LDR) of the second organic solvent with respect to the first functional layer is determined according to the following procedure:
  • the stability of the first functional layer is tested against the second organic solvent.
  • This second organic solvent is filled into a solvent stable 10 pl single-use-cartridge of the printer (any drop-on-demand inkjet printer/printhead can be used).
  • the cartridge size determines the droplet volume. In this case a ten picoliter cartridge is used.
  • the printer should be operated in a vibration-free environment and should be levelled.
  • the correct adjustment of printing conditions would be a droplet speed of 4 meters per second.
  • the printing is at best done using a single nozzle only.
  • the substrate with the first functional layer is now placed onto the substrate holder of the printer.
  • the print-pattern is programmed to a have a specific drop volume.
  • the drop on the surface consists of nine small single droplets which are positioned very close together in a 3 x 3 matrix. After printing the single droplets merge to form a single drop of ninety picoliter drop volume (the volume needs to be kept constant over one set of experiments).
  • the substrate After typically three hundred seconds soaking time the substrate is placed into a vacuum drying chamber to remove the solvent and dry the layer completely. The pressure reaches T10’ 4 mbar after 60 seconds of pumping. The substrate is fully dried for at least 10 minutes. After drying the substrate is removed and the damage to the surface is quantified. To quantify the damage to the layer, a tactile measurement such as Profilometry or AFM (Atomic force microscopy) can be done. The difference between lowest and highest point across the profile measurement is determined. The value has the unit nanometer. To determine the layer damage rate, this difference is divided by the soaking time. The unit for the layer damage rate is here nanometer per second [nm/sec]. In general, the soaking time should be in the range of a typical solution processing step.
  • the second organic solvent dissolves the organic functional material A very slowly when compared to the time period which is required to perform process steps b and c1 .
  • tDiss(materialA/solvent2) > 2 ⁇ t(b and c1 ), wherein tDiss(materialA/solvent2) is the dissolution time [sec] which is required to dissolve 7.00 g of the organic functional material A in 1 .00 I of the second organic solvent at 25°C; and t(b and c1 ) is the time period [sec] in which process steps b and c1 are carried out.
  • the dissolution time tDiss(materialA/solvent2) is determined as described above in the procedure for determining the dissolution rate of the organic functional material A in the second organic solvent.
  • the third organic solvent has a layer damage rate (LDR) with respect to the first functional layer of higher than 0.116 nm/sec at 25°C.
  • LDR layer damage rate
  • the layer damage rate (LDR) of the third organic solvent with respect to the first functional layer is determined in the same manner as described above with respect to the second solvent.
  • the organic functional material A is a non-crosslinkable polymer. It is more preferred that the organic functional material A is a non-crosslinkable polymer which is a holetransporting material.
  • Preferred polymeric hole-transporting materials are selected from polysilanes, aniline copolymers, thiophene oligomers, polythiophenes, poly(N-vinyl)carbazole, polypyrroles, polyanilines, polytriarylamines and mixtures thereof.
  • the polymeric hole-transporting material preferably has a molecular weight M w of > 10.000 g/mol.
  • the organic functional material A is a light-emitting material.
  • Preferred light emitting materials are fluorescent or phosphorescent emitters selected from the list consisting of stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene, pyrene and phosphorescent metal complexes, preferably containing Ir, Ru, Pd, Pt, Os or Re, and mixtures thereof. Two, three or more of the aforementioned preferred light emitting materials may be used in combination to form mixtures.
  • the light-emitting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • process step c1 is carried out in a time period of less than 600 sec, more preferably in a time period of less than 300 seconds.
  • process step c1 ) is carried out at a temperature in the range from 5 to 50°C, more preferably in the range from 10 to 35°C.
  • process step c1 is carried out by a printing process or a coating process. More preferably, process step c1 ) is carried out by an inkjet printing process.
  • the first organic solvent consists of one, two or more organic solvents.
  • the second organic solvent to be used in the process according to the present invention can be freely chosen so that the absolute solubility of the organic functional material A in the second organic solvent is in the range from 0.1 to 200 g/l at 25°C and in that the absolute solubility of the organic functional material B in the second organic solvent is in the range from 0.1 to 200 g/l at 25°C.
  • the absolute solubility of the organic functional material A in the second organic solvent is in the range from 5.0 to 200 g/l at 25°C, and more preferably from 5.1 to 200 g/l at 25°C
  • the absolute solubility of the organic functional material B in the second organic solvent is in the range from 5.0 to 200 g/l at 25°C, and more preferably from 5.1 to 200 g/l at 25°C.
  • the absolute solubility of the organic functional material A in the second organic solvent is in the range from 5.1 to 150 g/l at 25°C and the absolute solubility of the organic functional material B in the second organic solvent is in the range from 5.1 to 150 g/l at 25°C.
  • the absolute solubility as used in the present application is determined according to the standard procedure ISO 7579:2009.
  • ISO 7579:2009 specifies two methods for determining the solubility of dyestuffs in organic solvents. They are applicable to dyestuffs that do not change chemically under the influence of the solvent and are stable and nonvolatile under the specified drying conditions. For volatile solvents (boiling point ⁇ 120°C), the gravimetric procedure is recommended and, for less volatile solvents (boiling point > 120°C), the photometric procedure is recommended.
  • the second organic solvent may be a single solvent or two or more solvents. In a preferred embodiment the second organic solvent consists of one, two or more organic solvents.
  • the second organic solvent is an organic solvent having 8 to 14 carbon atoms and 1 to 3 oxygen and/or nitrogen atoms which contains one aromatic six-membered carbocyclic ring system or one or two aliphatic five- or six-membered carbocyclic ring systems.
  • the second organic solvent is an organic solvent having a boiling point in the range from 195 to 350°C, more preferably in the range from 210 to 300°C and most preferably in the range from 220 to 290°C, at 760 mm Hg.
  • the third organic solvent to be used in the process according to the present invention is not particularly limited.
  • third organic solvent any organic solvent may be used which allows sufficient solubility of the organic functional material B.
  • the third organic solvent may be a single solvent or two or more solvents.
  • the third organic solvent contains, one, two or more organic solvents.
  • Suitable solvents which may be used as third organic solvent are organic solvents such as ketones, substituted and non-substituted aromatic, alicyclic or linear ethers, esters, amides (e.g. di-Ci-2-alkylformamides), aromatic amines, sulfur compounds, nitro compounds, hydrocarbons, halogenated hydrocarbons (e.g.
  • the third organic solvent consists of one, two or more organic solvents.
  • the first organic solvent and the third organic solvent are the same.
  • the first organic solvent, the second organic solvent and the third organic solvent are liquids at 25°C and 760 mm Hg.
  • the organic electroluminescent device which is prepared according to the process of the present invention comprises a layered stack structure with two or more functional layers, wherein a first functional layer and a second functional layer are adjacent and together form an interface.
  • the first functional layer and the second functional layer are selected independently from an electron-injection layer, electron-transport layer, electron-blocking layer, hole-injection layer, hole-transport layer, hole-blocking layer and light emitting layer.
  • the first functional layer and the second functional layer are not identical which means that they have either a different function or they contain different organic functional materials.
  • Such organic functional materials are e.g.
  • a functional layer may contain one or more of the aforementioned organic functional materials.
  • the organic functional material A is a non- crosslinkable polymer. More preferably, the organic functional material A is a non-crosslinkable polymer which is a hole-transporting material.
  • Preferred polymeric hole-transporting materials are selected from the list consisting of polysilanes, aniline copolymers, thiophene oligomers, polythiophenes, poly(N-vinyl)carbazole, polypyrroles, polyanilines, polytriarylamines and mixtures thereof.
  • the polymeric hole-transporting material preferably has a molecular weight M w of > 10.000 g/mol.
  • the organic functional material B is a light-emitting material.
  • Preferred light emitting materials are fluorescent or phosphorescent emitters selected from the list consisting of stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene, pyrene and phosphorescent metal complexes, preferably containing Ir, Ru, Pd, Pt, Os or Re, and mixtures thereof. Two, three or more of the aforementioned preferred light emitting materials may be used in combination to form mixtures.
  • the light-emitting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • the organic functional material A is a light-emitting material.
  • Preferred light emitting materials are fluorescent or phosphores-cent emitters selected from the list consisting of stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene, pyrene and phosphorescent metal complexes, preferably containing Ir, Ru, Pd, Pt, Os or Re, and mixtures thereof. Two, three or more of the aforementioned preferred light emitting materials may be used in combination to form mixtures.
  • the light-emitting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • the organic functional material B is a hole-blocking or electron-transporting material.
  • Preferred hole-blocking and electron-transporting materials are selected from the group consisting of pyridines, pyrimidines, pyridazines, pyrazines, oxadiazoles, quinolines, quinoxalines, anthracenes, benzanthracenes, pyrenes, perylenes, benzimidazoles, triazines, ketones, phosphine oxides and phenazine derivatives, but also triarylboranes and further O-, S- or N-containing heterocycles having a low LIIMO.
  • the hole-blocking and electrontransporting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • a first solution containing at least an organic functional material A and at least a first organic solvent is deposited on a support.
  • the support on which the first solution is deposited may be any substrate which may be used for an OLED. Beyond that, the support may be an electrode (e.g. an anode or cathode) or any functional layer to be used in an OLED such as an electron-injection layer, electron-transport layer, electron- blocking layer, hole-injection layer, hole-transport layer, hole-blocking layer or light emitting layer.
  • the support forms the basis on which the first solution is deposited in process step a1 ).
  • process step a2) the first solution which is deposited on the support in process step a1 ) is dried and optionally annealed.
  • the drying is carried out in order to remove the solvent from the first solution which is deposited on the support in process step a1 ).
  • the drying in process step a2) is preferably carried out at relatively low temperature such as room temperature (25°C) and over a relatively long period in order to avoid bubble formation and to obtain a uniform functional layer.
  • relatively low temperature such as room temperature (25°C) and over a relatively long period in order to avoid bubble formation and to obtain a uniform functional layer.
  • the drying in process step a2) is preferably carried out under reduced pressure, more preferably at a pressure in the range from 10’ 6 mbar to 1 bar, particularly preferably in the range from 10’ 6 mbar to 100 mbar and most preferably in the range from 10’ 6 mbar to 10 mbar.
  • the duration of the drying in process step a2) depends on the degree of drying to be achieved.
  • the drying in process step a2) is preferably carried out within a time period of 1 to 60 minutes, more preferably within a time period of 1 to 30 minutes.
  • the drying in process step a2) may be optionally followed by an annealing.
  • the optional annealing in process step a2) is preferably carried out at an elevated temperature in the range from 80 to 300°C, more preferably at a temperature in the range from 150 to 250°C and most preferably at a temperature in the range from 160 to 220°C.
  • the optional annealing in process step a2) is preferably carried out under reduced pressure, more preferably at a pressure in the range from 1 to 1013 mbar.
  • the optional annealing in process step a2) is preferably carried out within a time period of 1 to 60 minutes, more preferably within a time period of 10 to 60 minutes.
  • the drying and annealing are combined and performed as a single step in process step a2).
  • the drying and annealing conditions are identical.
  • the temperature, pressure and time conditions, which are disclosed for drying are used for drying and annealing.
  • the temperature, pressure and time conditions, which are disclosed for annealing are used for drying and annealing.
  • drying and optional annealing in process step a2) is carried out within a total time period of 1 to 90 minutes, more preferably within a total time period of 1 to 60 minutes. This shall apply to all cases, regardless of whether the drying and optional annealing are performed at identical or different conditions.
  • process step b) a second solution containing at least a second organic solvent is deposited on the first functional layer obtained in process step a2). It is preferred that process step b) is carried out at a temperature in the range from 5 to 50°C, more preferably at a temperature in the range from 10 to 35°C. It is preferred that process step b) is carried out in a time period of less than 10 minutes, more preferably in a time period of less than 5 minutes.
  • process step c1 a third solution containing at least an organic functional material B and at least a third organic solvent is deposited into the second solution deposited in process step b). It is preferred that process step c1 ) is carried out at a temperature in the range from 5 to 50°C, more preferably at a temperature in the range from 10 to 35°C. It is preferred that process step c1 ) is carried out in a time period of less than 10 minutes, more preferably in a time period of less than 5 minutes.
  • process step c2) the second and third solution which are deposited on the first functional layer in process steps b) and c1 ) are dried and optionally annealed.
  • the drying in process step c2) is preferably carried out at relatively low temperature such as room temperature (25°C) and over a relatively long period in order to avoid bubble formation and to obtain a uniform functional layer.
  • relatively low temperature such as room temperature (25°C)
  • elevated temperature preferably in the range from 25 to 100°C, more preferably in the range from 25 to 60°C.
  • the drying in process step c2) is preferably carried out under reduced pressure, more preferably at a pressure in the range from 10’ 6 mbar to 1 bar, particularly preferably in the range from 10’ 6 mbar to 100 mbar and most preferably in the range from 10’ 6 mbar to 10 mbar.
  • the duration of the drying in process step c2) depends on the degree of drying to be achieved.
  • the drying in process step c2) is preferably carried out within a time period of 1 to 60 minutes, more preferably within a time period of 1 to 30 minutes.
  • the drying in process step c2) may be optionally followed by an annealing.
  • the optional annealing in process step c2) is preferably carried out at an elevated temperature in the range from 80 to 300°C, more preferably at a temperature in the range from 150 to 250°C and most preferably at a temperature in the range from 160 to 220°C.
  • the optional annealing in process step c2) is preferably carried out under reduced pressure, more preferably at a pressure in the range from 1 to 1013 mbar.
  • the optional annealing in process step c2) is preferably carried out within a time period of 1 to 60 minutes, more preferably within a time period of 10 to 60 minutes.
  • the drying and annealing are combined and performed as a single step in process step c2).
  • the drying and annealing conditions are identical.
  • the temperature, pressure and time conditions which are disclosed for drying are used for drying and annealing.
  • the temperature, pressure and time conditions which are disclosed for annealing are used for drying and annealing.
  • the drying and optional annealing in process step c2) is carried out within a total time period of 1 to 90 minutes, more preferably within a total time period of 1 to 60 minutes. This shall apply to all cases, regardless of whether the drying and optional annealing are performed at identical or different conditions.
  • the first, second and third solution may be deposited as liquid compositions using any suitable solution processing techniques known in the art.
  • the solution can be deposited using a printing process, such as e.g. inkjet printing, nozzle printing, offset printing, transfer printing, relief printing, gravure printing, rotary printing, flexographic printing or screen printing; or for example, using a coating process, such as e.g. spray coating, spin coating, slot coating, curtain coating, flood coating, roller coating or dip coating.
  • the depositions in process steps a1 ), b) and c1 ) are carried out by the same solution processing technique, more preferably by a printing process or a coating process and most preferably by an inkjet printing process.
  • Table 1 Examples of the most preferred second organic solvents, their boiling points (BP) and physical state at room temperature are shown in Table 1 below.
  • Table 1 Most preferred solvents to be used as second solvent, their boiling points (BP) and their physical state at room temperature (25°C).
  • the second solvent is liquid at room temperature (25°C) and standard pressure (760 mm Hg) which means that it has a melting point of 25°C or below at 760 mm Hg.
  • the second solvent is an organic solvent having a boiling point in the range from 195 to 350°C, more preferably in the range from 210 to 300°C and most preferably in the range from 220 to 290°C, wherein the boiling point is given at 760 mm Hg.
  • the first, the second as well as the third solution has a surface tension in the range from 1 to 70 mN/m, preferably in the range from 10 to 50 mN/m and more preferably in the range from 20 to 40 mN/m.
  • the surface tension of the solutions used in the present invention is measured by pendant drop characterization which is an optical method.
  • This measurement technique dispenses a drop from a needle in a bulk gaseous phase.
  • the shape of the drop results from the relationship between the surface tension, gravity and density differences.
  • the surface tension is calculated from the shadow image of a pendant drop using drops shape analysis.
  • a commonly used and commercially available high precision drop shape analysis tool namely the DSA100 from Kruss GmbH, was used to perform all surface tension measurements.
  • the surface tension is determined by the software “DSA4” in accordance with DIN 55660-1 . All measurements were performed at ambient temperature which is in the range between 22°C and 24°C.
  • the standard operating procedure includes the determination of the surface tension of each formulation using a fresh disposable drop dispensing system (syringe and needle). Each drop is measured over the duration of one minute with sixty measurements which are later on averaged. For each formulation three drops are measured. The final value is averaged over said measurements.
  • the tool is regularly cross-checked against various liquids having well known surface tension.
  • the first, the second as well as the third solution has a viscosity in the range from 0.8 to 50 mPas, more preferably in the range from 1 to 40 mPas, more preferably in the range from 2 to 20 mPas and most preferably in the range from 2 to 15 mPas.
  • the viscosity of the solutions used in the present invention is measured with a 1 ° cone-plate rotational rheometer of the type Haake MARS III Rheometer (Thermo Scientific).
  • the equipment allows a precise control of the temperature and sheer rate.
  • the measurement of the viscosity is carried out at a temperature of 23.4°C (+/- 0.2°C) and a sheer rate of 500 s’ 1 . Each sample is measured three times and the obtained measured values are averaged.
  • the measurement and processing of data is carried out using the software “Haake RheoWin Job Manager” according to DIN 1342-2.
  • the Haake MARS III Rheometer is regularly calibrated by Thermo Scientific and the tool received a certified standard factory calibration before first use.
  • the first as well as the third solvent is selected from the group consisting of substituted and non-substituted aromatic or non-aromatic, cyclic or linear esters such as ethyl benzoate, butyl benzoate; substituted and non-substituted aromatic or linear ethers such as 3-phenoxytoluene or anisole derivatives; substituted or non-substituted arene derivatives such as xylene; indane derivatives such as hexamethylindane; substituted and nonsubstituted aromatic or linear ketones; substituted and non-substituted heterocycles such as pyrrolidinones, pyridines; fluorinated or chlorinated hydrocarbons; and linear or cyclic siloxanes.
  • Particularly preferred first as well as third solvents are selected from
  • the content of the organic functional material A in the first solution as well as the content of the organic functional material B in the third solution is preferably in the range from 0.001 to 20 weight-%, more preferably in the range from 0.01 to 10 weight-% and most preferably in the range from 0.1 to 5 weight-%, based on the total weight of the first solution.
  • Such organic functional materials are e.g. electron-injection materials, electron-transport materials, electron-blocking materials, hole-injection materials, hole-transport materials, hole-blocking materials, light emitting materials such as fluorescent emitters or phosphorescent emitters, host materials, matrix materials, exciton-blocking materials, n-dopants, p- dopants and wide-band-gap materials.
  • a functional layer may contain one or more of the aforementioned organic functional materials.
  • the organic functional material A is a non- crosslinkable polymer. More preferably, the organic functional material A is a non-crosslinkable polymer which is a hole-transporting material.
  • Preferred hole-transporting materials are selected from the list consisting of polysilanes, aniline copolymers, thiophene oligomers, polythiophenes, poly(N-vinyl)carbazole, polypyrroles, polyanilines, polytriarylamines and mixtures thereof.
  • the polymeric hole-transporting material preferably has a molecular weight M w of > 10.000 g/mol.
  • the organic functional material B is a light-emitting material.
  • Preferred light emitting materials are fluorescent or phosphorescent emitters selected from the list consisting of stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene, pyrene and phosphorescent metal complexes, preferably containing Ir, Ru, Pd, Pt, Os or Re, and mixtures thereof.
  • the light-emitting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • the organic functional material A is a light-emitting material.
  • Preferred light emitting materials are fluorescent or phosphores-cent emitters selected from the list consisting of stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene, pyrene and phosphorescent metal complexes, preferably containing Ir, Ru, Pd, Pt, Os or Re, and mixtures thereof. Two, three or more of the aforementioned preferred light emitting materials may be used in combination to form mixtures.
  • the light-emitting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • the organic functional material B is a hole-blocking or electron-transporting material.
  • Preferred hole-blocking and electron-transporting materials are selected from the group consisting of pyridines, pyrimidines, pyridazines, pyrazines, oxadiazoles, quinolines, quinoxalines, anthracenes, benzanthracenes, pyrenes, perylenes, benzimidazoles, triazines, ketones, phosphine oxides and phenazine derivatives, but also triarylboranes and further O-, S- or N-containing heterocycles having a low LIIMO.
  • the hole-blocking and electrontransporting material is preferably a low molecular weight material having a molecular weight of ⁇ 3.000 g/mol.
  • the solutions used as first or third solution in the present invention comprise at least one organic functional material which can be employed for the production of functional layers of electronic devices such as e.g. organic electroluminescent devices (OLEDs).
  • Organic functional materials are generally the organic materials which are introduced between the anode and the cathode of an electronic device.
  • the organic functional material is preferably selected from organic conductors, organic semiconductors, organic fluorescent compounds, organic phosphorescent compounds, organic light-absorbent compounds, organic light-sensitive compounds, organic photosensitisation agents and other organic photoactive compounds, selected from organometallic complexes of transition metals, rare earths, lanthanides and actinides.
  • Particularly preferred organic functional materials are e.g.
  • electron-injection materials electron-transport materials, electron-blocking materials, hole-injection materials, hole-transport materials, hole-blocking materials, light emitting materials such as fluorescent emitters or phosphorescent emitters, host materials, matrix materials, exciton-blocking materials, n-dopants, p- dopants and wide-band-gap materials.
  • the organic functional material can be a compound having a low molecular weight, a polymer, an oligomer or a dendrimer, where the organic functional material may also be in the form of a mixture.
  • the first solution comprises two or more different organic functional materials as organic functional material A.
  • Such two or more different organic functional materials, which make up the organic functional material A may be either low molecular weight molecules or polymers or a mixture of at least one low molecular weight molecule and at least one polymer.
  • the first solution comprises two different organic functional materials having a low molecular weight, one organic functional material having a low molecular weight and one organic functional material being a polymer or two organic functional materials being polymers as organic functional material A.
  • the third solution comprises two or more different organic functional materials as organic functional material B.
  • Such two or more organic functional materials, which make up the organic functional material B may be either low molecular weight molecules or polymers or a mixture of at least one low molecular weight molecule and at least one polymer.
  • the third solution comprises two different organic functional materials having a low molecular weight, one organic functional material having a low molecular weight and one organic functional material being a polymer or two organic functional materials being polymers as organic functional material B.
  • organic functional materials having a low molecular weight have a molecular weight M w of ⁇ 3,000 g/mol, more preferably ⁇ 2,000 g/mol and most preferably ⁇ 1 ,800 g/mol.
  • organic functional materials being a polymer have a molecular weight Mw of > 10,000 g/mol, more preferably > 20,000 g/mol and most preferably > 50,000 g/mol.
  • the molecular weight Mw of the polymers here is preferably in the range from 10,000 to 2,000,000 g/mol, more preferably in the range from 20,000 to 1 ,000,000 g/mol and most preferably in the range from 50,000 to 300,000 g/mol.
  • Organic functional materials are frequently described by the properties of their frontier orbitals, which are described in greater detail below.
  • Molecular orbitals in particular also the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LIIMO), their energy levels and the energy of the lowest triplet state Ti or of the lowest excited singlet state Si of the materials are determined via quantum-chemical calculations.
  • HOMO highest occupied molecular orbital
  • LIIMO lowest unoccupied molecular orbital
  • their energy levels and the energy of the lowest triplet state Ti or of the lowest excited singlet state Si of the materials are determined via quantum-chemical calculations.
  • a geometry optimisation is carried out using the "Ground State/Semi-empirical/Default Spin/AM1/Charge O/Spin Singlet" method.
  • An energy calculation is subsequently carried out on the basis of the optimised geometry.
  • the "TD-SCF/ DFT/Default Spin/B3PW91" method with the "6-31 G(d)" base set (charge 0, spin singlet) is used here.
  • the geometry is optimised via the "Ground State/ Hartree-Fock/Default Spin/LanL2MBZ Charge 0/Spin Singlet” method.
  • the energy calculation is carried out analogously to the above-described method for the organic substances, with the difference that the "LanL2DZ" base set is used for the metal atom and the "6-31 G(d)" base set is used for the ligands.
  • the energy calculation gives the HOMO energy level HEh or LIIMO energy level LEh in hartree units.
  • the HOMO and LIIMO energy levels in electron volts calibrated with reference to cyclic voltammetry measurements are determined therefrom as follows:
  • these values are to be regarded as HOMO and LIIMO energy levels respectively of the materials.
  • the lowest triplet state Ti is defined as the energy of the triplet state having the lowest energy which arises from the quantum-chemical calculation described.
  • the lowest excited singlet state Si is defined as the energy of the excited singlet state having the lowest energy which arises from the quantumchemical calculation described.
  • hole-injection materials Materials having hole-injection properties, also called hole-injection materials herein, simplify or facilitate the transfer of holes, i.e. positive charges, from the anode into an organic layer.
  • a hole-injection material has an HOMO level which is in the region of or above the Fermi level of the anode.
  • hole-transport materials are capable of transporting holes, i.e. positive charges, which are generally injected from the anode or an adjacent layer, for example a hole-injection layer.
  • a hole-transport material generally has a high HOMO level of preferably at least -5.4 eV.
  • Polymers such as PEDOT:PSS can also be used as compounds with hole-injection and/or hole-transport properties.
  • phenylenediamine derivatives (US 3615404), arylamine derivatives (US 3567450), amino-substituted chaicone derivatives (US 3526501 ), styrylanthracene derivatives (JP-A-56- 46234), polycyclic aromatic compounds (EP 1009041 ), polyarylalkane derivatives (US 3615402), fluorenone derivatives (JP-A-54-110837), hydrazone derivatives (US 3717462), acylhydrazones, stilbene derivatives (JP-A- 61 -210363), silazane derivatives (US 4950950), polysilanes (JP-A-2- 204996), aniline copolymers (J P-A-2 -282263), thiophene oligomers
  • arylamine dendrimers JP Heisei 8 (1996) 193191
  • monomeric triarylamines US 3180730
  • triarylamines containing one or more vinyl radicals and/or at least one functional group containing active hydrogen US 3567450 and US 3658520
  • tetraaryldiamines the two tertiary amine units are connected via an aryl group.
  • More triarylamino groups may also be present in the molecule.
  • Phthalocyanine derivatives, naphthalocyanine derivatives, butadiene derivatives and quinoline derivatives, such as, for example, dipyrazino[2,3-f:2’,3’-h]quinoxalinehexacarbo- nitrile, are also suitable.
  • Preference is likewise given to hexa- azatriphenylene compounds in accordance with US 2007/0092755 A1 and phthalocyanine derivatives (for example H2PC, CuPc ( copper phthalocyanine), CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, CIAIPc, CIGaPc, CllnPc, CISnPc, CI 2 SiPc, (HO)AIPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPc-O- GaPc).
  • triarylamine compounds of the formulae (TA-1 ) to (TA-12) which are disclosed in the documents EP 1162193 B1 , EP 650 955 B1 , Synth. Metals 1997, 91 (1 -3), 209, DE 19646119 A1 , WO 2006/122630 A1 , EP 1 860 097 A1 , EP 1834945 A1 , JP 08053397 A, US 6251531 B1 , US 2005/0221124, JP 08292586 A, US 7399537 B2, US 2006/0061265 A1 , EP 1 661 888 and WO 2009/041635.
  • the said compounds of the formulae (TA-1 ) to (TA-12) may also be substituted: formula TA-2
  • arylamines and heterocycles which are generally employed as holeinjection and/or hole-transport materials preferably result in an HOMO in the polymer of greater than -5.8 eV (vs. vacuum level), particularly preferably greater than -5.5 eV.
  • LUMO lowest unoccupied molecular orbital
  • Particularly suitable compounds for electron-transporting and electroninjecting layers are metal chelates of 8-hydroxyquinoline (for example LiQ, AIQ3, GaQs, MgQ2, ZnQ2, InQs, ZrC ), BAIQ, Ga oxinoid complexes, 4-azaphenanthren-5-ol-Be complexes (US 5529853 A, cf. formula ET-1 ), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), benzimidazole derivatives (US 2007/0273272 A1 ), such as, for example, TPBI (US 5766779, of.
  • 8-hydroxyquinoline for example LiQ, AIQ3, GaQs, MgQ2, ZnQ2, InQs, ZrC
  • BAIQ Ga oxinoid complexes
  • 4-azaphenanthren-5-ol-Be complexes US 5529853 A, cf. formula ET-1
  • butadiene derivatives (US 4356429
  • 1 ,3,5-triazines for example spirobifluorenyltriazine derivatives (for example in accordance with DE 102008064200), pyrenes, anthracenes, tetracenes, fluorenes, spirofluorenes, dendrimers, tetracenes (for example rubrene derivatives), 1 ,10- phenanthroline derivatives (JP 2003-115387, JP 2004-311184, JP-2001- 267080, WO 02/043449), silacyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives, such as, for example, tri- arylborane derivatives containing Si (US 2007/0087219 A1 , cf.
  • spirobifluorenyltriazine derivatives for example in accordance with DE 102008064200
  • pyrenes for example in accordance with DE 10200
  • formula ET- 3 formula ET- 3
  • pyridine derivatives JP 2004-200162
  • phenanthrolines especially 1 ,10- phenanthroline derivatives, such as, for example, BCP and Bphen, also several phenanthrolines connected via biphenyl or other aromatic groups (US-2007-0252517 A1 ) or phenanthrolines connected to anthracene (US 2007-0122656 A1 , cf. formulae ET-4 and ET-5).
  • heterocyclic organic compounds such as, for example, thiopyran dioxides, oxazoles, triazoles, imidazoles or oxadiazoles.
  • heterocyclic organic compounds such as, for example, thiopyran dioxides, oxazoles, triazoles, imidazoles or oxadiazoles.
  • five-membered rings containing N such as, for example, oxazoles, preferably 1 ,3,4-oxadiazoles, for example compounds of the formulae ET-6, ET-7, ET-8 and ET-9, which are disclose, inter alia, in US 2007/0273272 A1 ; thiazoles, oxadiazoles, thiadiazoles, triazoles, inter alia, see US 2008/0102311 A1 and Y.A. Levin, M.S.
  • n-Dopants herein are taken to mean reducing agents, i.e. electron donors.
  • WO 2012/031735 A1 free radicals and diradicals (e.g. EP 1837926 A1 , WO 2007/107306 A1 ), pyridines (e.g. EP 2452946 A1 , EP 2463927 A1 ), N-heterocyclic compounds (e.g. WO 2009/000237 A1 ) and acridines as well as phenazines (e.g. US 2007/145355 A1 ).
  • the formulations may comprise emitters.
  • emitter denotes a material which, after excitation, which can take place by transfer of any type of energy, allows a radiative transition into a ground state with emission of light.
  • two classes of emitter are known, namely fluorescent and phosphorescent emitters.
  • fluorescent emitter denotes materials or compounds in which a radiative transition from an excited singlet state into the ground state takes place.
  • phosphorescent emitter preferably denotes luminescent materials or compounds which contain transition metals.
  • Emitters are frequently also called dopants if the dopants cause the properties described above in a system.
  • a dopant in a system comprising a matrix material and a dopant is taken to mean the component whose proportion in the mixture is the smaller.
  • a matrix material in a system comprising a matrix material and a dopant is taken to mean the component whose proportion in the mixture is the greater.
  • the term phosphorescent emitter can also be taken to mean, for example, phosphorescent dopants.
  • Compounds which are able to emit light include, inter alia, fluorescent emitters and phosphorescent emitters. These include, inter alia, compounds containing stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene and/or pyrene structures. Particular preference is given to compounds which are able to emit light from the triplet state with high efficiency, even at room temperature, i.e. exhibit electrophosphorescence instead of electrofluorescence, which frequently causes an increase in the energy efficiency.
  • Suitable for this purpose are firstly compounds which contain heavy atoms having an atomic number of greater than 36. Preference is given to compounds which contain d- or f-transition metals which satisfy the above- mentioned condition. Particular preference is given here to corresponding compounds which contain elements from group 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt).
  • Suitable functional compounds here are, for example, various complexes, as described, for example, in WO 02/068435 A1 , WO 02/081488 A1 , EP 1239526 A2 and WO 2004/026886 A2.
  • Preferred compounds which can serve as fluorescent emitters are described by way of example below.
  • Preferred fluorescent emitters are selected from the class of the monostyrylamines, the distyrylamines, the tristyrylamines, the tetrastyrylamines, the styrylphosphines, the styryl ethers and the arylamines.
  • a monostyrylamine is taken to mean a compound which contains one substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
  • a distyrylamine is taken to mean a compound which contains two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tristyrylamine is taken to mean a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tetrastyrylamine is taken to mean a compound which contains four substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • the styryl groups are particularly preferably stilbenes, which may also be further substituted.
  • Corresponding phosphines and ethers are defined analogously to the amines.
  • An arylamine or an aromatic amine in the sense of the present invention is taken 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, preferably having at least 14 aromatic ring atoms.
  • aromatic anthracenamines are taken to mean a compound in which one diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • aromatic anthracenediamine is taken to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 2,6- or 9,10-position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, where the diarylamino groups are preferably bonded to the pyrene in the 1 -position or in the 1 ,6-position.
  • fluorescent emitters are selected from indenofluoren- amines or indenofluorenediamines, which are described, inter alia, in WO 2006/122630; benzoindenofluorenamines or benzoindenofluorenedi- amines, which are described, inter alia, in WO 2008/006449; and dibenzo- indenofluorenamines or dibenzoindenofluorenediamines, which are described, inter alia, in WO 2007/140847.
  • Examples of compounds from the class of the styrylamines which can be employed as fluorescent emitters are substituted or unsubstituted tristilben- amines or the dopants described in WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549 and WO 2007/115610.
  • Distyrylbenzene and distyrylbiphenyl derivatives are described in US 5121029. Further styrylamines can be found in US 2007/0122656 A1 .
  • Particularly preferred styrylamine compounds are the compounds of the formula EM-1 described in US 7250532 B2 and the compounds of the formula EM-2 described in DE 10 2005 058557 A1 : formula EM-1 formula EM-2
  • triarylamine compounds are compounds of the formulae EM-3 to EM-15 disclosed in CN 1583691 A, JP 08/053397 A and US 6251531 B1 , EP 1957606 A1 , US 2008/0113101 A1 , US 2006/210830 A , WO 2008/006449 and DE 102008035413 and derivatives thereof: formula EM-3 formula EM-4 formula EM-9 formula EM-10 formula EM-15
  • Further preferred compounds which can be employed as fluorescent emitters are selected from derivatives of naphthalene, anthracene, tetracene, benzanthracene, benzophenanthrene (DE 10 2009 005746), fluorene, fluoranthene, periflanthene, indenoperylene, phenanthrene, perylene (US 2007/0252517 A1 ), pyrene, chrysene, decacyclene, coronene, tetra- phenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene, rubrene, coumarine (US 4769292, US 6020078, US 2007/ 0252517 A1 ), pyran, oxazole, benzoxazole, benzothiazole, benzimidazole, pyrazine, cinnamic acid esters, diketopyrrolopyrrol
  • 9,10- substituted anthracenes such as, for example, 9,10-diphenylanthracene and 9,10-bis(phenylethynyl)anthracene.
  • 1,4-Bis(9’-ethynylanthracenyl)- benzene is also a preferred dopant.
  • DMQA N,N’-dimethylquinacri- done
  • thiopyran poly- methine, pyrylium and thiapyrylium salts, periflanthen
  • Blue fluorescent emitters are preferably polyaromatic compounds, such as, for example, 9,10-di(2-naphthylanthracene) and other anthracene derivatives, derivatives of tetracene, xanthene, perylene, such as, for example, 2,5,8, 11 -tetra-f-butylperylene, phenylene, for example 4,4’-bis(9-ethyl-3- carbazovinylene)-1 ,1 ’-biphenyl, fluorene, fluoranthene, arylpyrenes
  • polyaromatic compounds such as, for example, 9,10-di(2-naphthylanthracene) and other anthracene derivatives, derivatives of tetracene, xanthene, perylene, such as, for example, 2,5,8, 11 -tetra-f-butylperylene, phenylene, for example 4,4’-bis(9-e
  • blue-fluorescent emitters are the hydrocarbons disclosed in WO 2010/012328 A1 , WO 2014/111269 A2 and PCT/EP2017/066712. Preferred compounds which can serve as phosphorescent emitters are described below by way of example.
  • Examples of phosphorescent emitters are revealed by WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614 and WO 2005/033244.
  • all phosphorescent complexes as are used in accordance with the prior art for phosphorescent OLEDs and as are known to the person skilled in the art in the area of organic electroluminescence are suitable, and the person skilled in the art will be able to use further phosphorescent complexes without inventive step.
  • Phosphorescent metal complexes preferably contain Ir, Ru, Pd, Pt, Os or Re.
  • Preferred ligands are 2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2-(2-thienyl)pyridine derivatives, 2-(1-naphthyl)pyridine derivatives, 1 -phenylisoquinoline derivatives, 3-phenylisoquinoline derivatives or 2-phenylquinoline derivatives. All these compounds may be substituted, for example by fluoro, cyano and/or trifluoromethyl substituents for blue.
  • Auxiliary ligands are preferably acetylacetonate or picolinic acid.
  • Particularly preferred compounds which are used as phosphorescent dopants are, inter alia, the compounds of the formula EM-17 described, inter alia, in US 2001/0053462 A1 and Inorg. Chem. 2001 , 40(7), 1704- 1711 , JACS 2001 , 123(18), 4304-4312, and derivatives thereof.
  • formula EM-17 Derivatives are described in US 7378162 B2, US 6835469 B2 and
  • Quantum dots can likewise be employed as emitters, these materials being disclosed in detail in WO 2011 /076314 A1 .
  • Compounds which are employed as host materials, in particular together with emitting compounds, include materials from various classes of substance. Host materials gereally have larger band gaps between HOMO and LIIMO than the emitter materials employed. In addition, preferred host materials exhibit properties of either a hole- or electron-transport material. Furthermore, host materials can have both electron- and hole-transport properties.
  • Host materials are in some cases also called matrix material, in particular if the host material is employed in combination with a phosphorescent emitter in an OLED.
  • Particularly preferred compounds which can serve as host materials or cohost materials are selected from the classes of the oligoarylenes, comprising anthracene, benzanthracene and/or pyrene, or atropisomers of these compounds.
  • An oligoarylene in the sense of the present invention is intended to be taken to mean a compound in which at least three aryl or arylene groups are bonded to one another.
  • Preferred host materials are selected, in particular, from compounds of the formula (H-1 ),
  • the group Ar 5 particularly preferably stands for anthracene, and the groups Ar 4 and Ar 6 are bonded in the 9- and 10-position, where these groups may optionally be substituted.
  • at least one of the groups Ar 4 and/or Ar 6 is a condensed aryl group selected from 1 - or 2-naphthyl, 2-, 3- or 9-phenanthrenyl or 2-, 3-, 4-, 5-, 6- or 7-benzanthracenyl.
  • Anthracene-based compounds are described in US 2007/0092753 A1 and US 2007/0252517 A1 , for example 2-(4-methylphenyl)-9, 10-di-(2-naphthyl)anthracene, 9-(2-naphthyl)-10-(1 , 1 biphenyl)anthracene and 9, 10-bis[4-(2,2-diphenylethenyl)phenyl]anthra- cene, 9,10-diphenylanthracene, 9,10-bis(phenylethynyl)anthracene and 1 ,4-bis(9’-ethynylanthracenyl)benzene.
  • Further preferred compounds are derivatives of arylamine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarine, oxadiazole, bisbenzoxazoline, oxazole, pyridine, pyrazine, imine, benzothiazole, benzoxazole, benzimidazole (US 2007/0092753 A1 ), for example 2,2’,2”-(1 ,3,5-phenylene)tris[1 -phenyl-1 H-benzimidazole], aldazine, stilbene, styrylarylene derivatives, for example 9,10-bis[4-(2,2-diphenyl- ethenyl)phenyl]anthracene, and distyrylarylene derivatives (US 5121029)
  • TNB 4,4’-bis[N-(1 -naphthyl)-N-(2-naphthyl)amino]biphenyl.
  • Metal-oxinoid complexes such as LiQ or AIQ3, can be used as co-hosts.
  • Preferred compounds with oligoarylene as matrix are disclosed in US 2003/ 0027016 A1 , US 7326371 B2, US 2006/043858 A, WO 2007/114358, WO 2008/145239, JP 3148176 B2, EP 1009044, US 2004/018383, WO 2005/061656 A1 , EP 0681019B1 , WO 2004/013073A1 , US 5077142, WO 2007/065678 and DE 102009005746, where particularly preferred compounds are described by the formulae H-2 to H-8.
  • compounds which can be employed as host or matrix include materials which are employed together with phosphorescent emitters.
  • CBP N,N-biscarbazolylbiphenyl
  • carbazole derivatives for example in accordance with WO 2005/039246, US 2005/0069729, JP 2004/288381 , EP 1205527 or WO 2008/086851
  • azacarbazoles for example in accordance with EP 1617710, EP 1617711 , EP 1731584 or JP 2005/347160
  • ketones for example in accordance with WO 2004/ 093207 or in accordance with DE 102008033943
  • phosphine oxides, sulfoxides and sulfones for example in accordance with WO 2005/003253
  • oligophenylenes for example in accordance with US 2005/0069729)
  • bipolar matrix materials for example in accordance with WO 2007/137725
  • silanes for example in accordance with WO 2005/ 111172
  • Preferred tetraaryl-Si compounds are disclosed, for example, in US 2004/ 0209115, US 2004/0209116, US 2007/0087219 A1 and in H. Gilman, E.A. Zuech, Chemistry & Industry (London, United Kingdom), 1960, 120.
  • Particularly preferred compounds from group 4 for the preparation of the matrix for phosphorescent dopants are disclosed, inter alia, in
  • a plurality of different matrix materials as a mixture, in particular at least one electron-transporting matrix material and at least one hole-transporting matrix material.
  • formulations may comprise a wide-band-gap material as functional material.
  • Wide-band-gap material is taken to mean a material in the sense of the disclosure content of US 7,294,849. These systems exhibit particularly advantageous performance data in electroluminescent devices.
  • the compound employed as wide-band-gap material can preferably have a band gap of 2.5 eV or more, preferably 3.0 eV or more, particularly preferably 3.5 eV or more.
  • the band gap can be calculated, inter alia, by means of the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).
  • the formulations may comprise a hole-blocking material (HBM) as functional material.
  • HBM hole-blocking material
  • a hole-blocking material denotes a material which prevents or minimises the transmission of holes (positive charges) in a multilayer system, in particular if this material is arranged in the form of a layer adjacent to an emission layer or a hole-transporting layer.
  • a hole-blocking material has a lower HOMO level than the hole-transport material in the adjacent layer.
  • Hole-blocking layers are frequently arranged between the light-emitting layer and the electron-transport layer in OLEDs.
  • advantageous hole-blocking materials are metal complexes (US 2003/0068528), such as, for example, bis(2-methyl-8-quinolinolato)(4- phenylphenolato)aluminium(lll) (BAIQ). Fac-tris(1 -phenylpyrazolato-N,C2)- iridium(lll) (Ir(ppz)s) is likewise employed for this purpose (US 2003/ 0175553 A1 ). Phenanthroline derivatives, such as, for example, BCP, or phthalimides, such as, for example, TMPP, can likewise be employed.
  • the formulations may comprise an electron-blocking material (EBM) as functional material.
  • EBM electron-blocking material
  • An electron-blocking material denotes a material which prevents or minimises the transmission of electrons in a multilayer system, in particular if this material is arranged in the form of a layer adjacent to an emission layer or an electron-transporting layer.
  • an electron-blocking material has a higher LUMO level than the electron-transport material in the adjacent layer.
  • advantageous electron-blocking materials are transition-metal complexes, such as, for example, lr(ppz)3 (US 2003/ 0175553).
  • the electron-blocking material can preferably be selected from amines, tri- arylamines and derivatives thereof.
  • the functional compounds which can be employed as organic functional materials in the formulations preferably have, if they are low- molecular-weight compounds, a molecular weight of ⁇ 3,000 g/mol, particularly preferably ⁇ 2,000 g/mol and especially preferably ⁇ 1 ,800 g/mol.
  • particularly preferred functional compounds which can be employed as organic functional material in the formulations are those which have a glasstransition temperature of > 70°C, preferably > 100°C, particularly preferably > 125°C and especially preferably > 150°C, determined in accordance with DIN 51005.
  • the formulations may also comprise polymers as organic functional materials.
  • the compounds described above as organic functional materials which frequently have a relatively low molecular weight, can also be mixed with a polymer. It is likewise possible to incorporate these compounds covalently into a polymer. This is possible, in particular, with compounds which are substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid ester, or by reactive, polymerisable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers or polymers.
  • the oligomerisation or polymerisation here preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerisable group. It is furthermore possible to crosslink the polymers via groups of this type.
  • the compounds and polymers according to the invention can be employed as crosslinked or uncrosslinked layer.
  • Polymers which can be employed as organic functional materials frequently contain units or structural elements which have been described in the context of the compounds described above, inter alia those as disclosed and extensively listed in WO 02/077060 A1 , in WO 2005/014689 A2 and in WO 2011/076314 A1 . These are incorporated into the present application by way of reference.
  • the functional materials can originate, for example, from the following classes:
  • Group 1 structural elements which are able to generate hole-injection and/or hole-transport properties
  • Group 2 structural elements which are able to generate electroninjection and/or electron-transport properties
  • Group 3 structural elements which combine the properties described in relation to groups 1 and 2;
  • Group 4 structural elements which have light-emitting properties, in particular phosphorescent groups
  • Group 5 structural elements which improve the transition from the so-called singlet state to the triplet state
  • Group 6 structural elements which influence the morphology or also the emission colour of the resultant polymers
  • Group 7 structural elements which are typically used as backbone.
  • the structural elements here may also have various functions, so that a clear assignment need not be advantageous.
  • a structural element of group 1 may likewise serve as backbone.
  • the polymer having hole-transport or hole-injection properties employed as organic functional material, containing structural elements from group 1 may preferably contain units which correspond to the hole-transport or holeinjection materials described above.
  • group 1 is, for example, triaryl- amine, benzidine, tetraaryl-para-phenylenediamine, carbazole, azulene, thiophene, pyrrole and furan derivatives and further O-, S- or N-containing heterocycles having a high HOMO.
  • arylamines and heterocycles preferably have an HOMO of above -5.8 eV (against vacuum level), particularly preferably above -5.5 eV.
  • HTP-1 in which the symbols have the following meaning:
  • Ar 1 is, in each case identically or differently for different recurring units, a single bond or a monocyclic or polycyclic aryl group, which may optionally be substituted;
  • Ar 2 is, in each case identically or differently for different recurring units, a monocyclic or polycyclic aryl group, which may optionally be substituted;
  • Ar 3 is, in each case identically or differently for different recurring units, a monocyclic or polycyclic aryl group, which may optionally be substituted; m is 1 , 2 or 3.
  • HTP-1 which are selected from the group consisting of units of the formulae HTP-1 A to HTP-1 C:
  • R a is on each occurrence, identically or differently, H, a substituted or unsubstituted aromatic or heteroaromatic group, an alkyl, cycloalkyl, alkoxy, aralkyl, aryloxy, arylthio, alkoxycarbonyl, silyl or carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; r is 0, 1 , 2, 3 or 4, and s is 0, 1 , 2, 3, 4 or 5.
  • T 1 and T 2 are selected independently from thiophene, selenophene, thieno- [2,3-b]thiophene, thieno[3,2-b]thiophene, dithienothiophene, pyrrole and aniline, where these groups may be substituted by one or more radicals R b ;
  • Ar 7 and Ar 8 represent, independently of one another, a monocyclic or polycyclic aryl or heteroaryl group, which may optionally be substituted and may optionally be bonded to the 2,3-position of one or both adjacent thiophene or selenophene groups; c and e are, independently of one another, 0, 1 , 2, 3 or 4, where 1 ⁇ c + e ⁇ 6; d and f are, independently of one another, 0, 1 , 2, 3 or 4.
  • Preferred examples of polymers having hole-transport or hole-injection properties are described, inter alia, in WO 2007/131582 A1 and WO 2008/009343 A1 .
  • the polymer having electron-injection and/or electron-transport properties employed as organic functional material, containing structural elements from group 2, may preferably contain units which correspond to the electron-injection and/or electron-transport materials described above.
  • group 2 which have electroninjection and/or electron-transport properties are derived, for example, from pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline and phenazine groups, but also triarylborane groups or further O-, S- or N-containing heterocycles having a low LIIMO level.
  • These structural elements of group 2 preferably have an LIIMO of below -2.7 eV (against vacuum level), particularly preferably below -2.8 eV.
  • the organic functional material can preferably be a polymer which contains structural elements from group 3, where structural elements which improve the hole and electron mobility (i.e. structural elements from groups 1 and 2) are connected directly to one another.
  • Some of these structural elements can serve as emitters here, where the emission colours may be shifted, for example, into the green, red or yellow. Their use is therefore advantageous, for example, for the generation of other emission colours or a broad-band emission by polymers which originally emit in blue.
  • the polymer having light-emitting properties employed as organic functional material, containing structural elements from group 4 may preferably contain units which correspond to the emitter materials described above. Preference is given here to polymers containing phosphorescent groups, in particular the emitting metal complexes described above which contain corresponding units containing elements from groups 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt).
  • the polymer employed as organic functional material containing units of group 5 which improve the transition from the so-called singlet state to the triplet state can preferably be employed in support of phosphorescent compounds, preferably the polymers containing structural elements of group 4 described above.
  • a polymeric triplet matrix can be used here.
  • Suitable for this purpose are, in particular, carbazole and connected carbazole dimer units, as described, for example, in DE 10304819 A1 and DE 10328627 A1 . Also suitable for this purpose are ketone, phosphine oxide, sulfoxide, sulfone and silane derivatives and similar compounds, as described, for example, in DE 10349033 A1. Furthermore, preferred structural units can be derived from compounds which have been described above in connection with the matrix materials employed together with phosphorescent compounds.
  • the further organic functional material is preferably a polymer containing units of group 6 which influence the morphology and/or the emission colour of the polymers.
  • these are those which have at least one further aromatic or another conjugated structure which do not count amongst the above-mentioned groups. These groups accordingly have only little or no effect on the charge-carrier mobilities, the non-organometallic complexes or the singlet-triplet transition.
  • the polymers may also include cross-linkable groups such as styrene, benzocyclobutene, epoxide and oxetane moieties.
  • Structural units of this type are able to influence the morphology and/or the emission colour of the resultant polymers. Depending on the structural unit, these polymers can therefore also be used as emitters.
  • aromatic structural elements having 6 to 40 C atoms or also tolan, stilbene or bis- styrylarylene derivative units, each of which may be substituted by one or more radicals.
  • Particular preference is given here to the use of groups derived from 1 ,4-phenylene, 1 ,4-naphthylene, 1 ,4- or 9,10-anthrylene, 1 ,6- 2,7- or 4,9-pyrenylene, 3,9- or 3,10-perylenylene, 4,4'-biphenylene, 4,4"- terphenylylene, 4,4'-bi-1 ,1'-naphthylylene, 4,4‘-tolanylene, 4,4'-stilbenylene or 4,4"-bisstyrylarylene derivatives.
  • the polymer employed as organic functional material preferably contains units of group 7, which preferably contain aromatic structures having 6 to 40 C atoms which are frequently used as backbone.
  • 4,5-dihydropyrene derivatives 4,5,9, 10-tetra- hydropyrene derivatives, fluorene derivatives, which are disclosed, for example, in US 5962631 , WO 2006/052457 A2 and WO 2006/118345A1 , 9,9-spirobifluorene derivatives, which are disclosed, for example, in WO 2003/020790 A1 , 9,10-phenanthrene derivatives, which are disclosed, for example, in WO 2005/104264 A1 , 9, 10-dihydrophenanthrene derivatives, which are disclosed, for example, in WO 2005/014689 A2, 5,7-dihydrodibenzoxepine derivatives and cis- and trans-indenofluorene derivatives, which are disclosed, for example, in WO 2004/041901 A1 and WO 2004/113412 A2, and binaphthylene derivatives, which are disclosed, for example, in WO 2006/063852
  • group 7 which are selected from fluorene derivatives, which are disclosed, for example, in US 5,962,631 , WO 2006/052457 A2 and WO 2006/118345 A1 , spiro- bifluorene derivatives, which are disclosed, for example, in WO 2003/ 020790 A1 , benzofluorene, dibenzofluorene, benzothiophene and dibenzofluorene groups and derivatives thereof, which are disclosed, for example, in WO 2005/056633 A1 , EP 1344788 A1 and WO 2007/043495 A1 .
  • X is halogen
  • R° and R 00 are each, independently, H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 carbon atoms, which may optionally be substituted and may optionally contain one or more heteroatoms;
  • g is in each case, independently, 0 or 1 and h is in each case, independently, 0 or 1 , where the sum of g and h in a sub-unit is preferably 1 ;
  • m is an integer > 1 ;
  • Ar 1 and Ar 2 represent, independently of one another, a monocyclic or polycyclic aryl or heteroaryl group, which may optionally be substituted and may optionally be bonded to the 7,8-position or the 8,9-position of an indeno- fluorene group; a and b are, independently of one another, 0 or 1 . If the groups R c and R d form a spiro group with the fluorene group to which these groups are bonded, this group preferably represents a spiro- bifluorene.
  • recurring units of the formula PB-1 which are selected from the group consisting of units of the formulae PB-1 A to PB-1 E: formula PB-1 C where R c has the meaning described above for formula PB-1 , r is 0, 1 , 2, 3 or 4, and R e has the same meaning as the radical R c .
  • recurring units of the formula PB-1 which are selected from the group consisting of units of the formulae PB-1 F to PB-11: formula PB-11 in which the symbols have the following meaning: L is H, halogen or an optionally fluorinated, linear or branched alkyl or alkoxy group having 1 to 12 C atoms and preferably stands for H, F, methyl, i-propy I , t-butyl, n-pentoxy or trifluoromethyl; and
  • L' is an optionally fluorinated, linear or branched alkyl or alkoxy group having 1 to 12 C atoms and preferably stands for n-octyl or n-octyloxy.
  • polymers which contain more than one of the structural elements of groups 1 to 7 described above. It may furthermore be provided that the polymers preferably contain more than one of the structural elements from one group described above, i.e. comprise mixtures of structural elements selected from one group.
  • polymers which, besides at least one structural element which has light-emitting properties (group 4), preferably at least one phosphorescent group, additionally contain at least one further structural element of groups 1 to 3, 5 or 6 described above, where these are preferably selected from groups 1 to 3.
  • the proportion of the various classes of groups, if present in the polymer can be in broad ranges, where these are known to the person skilled in the art. Surprising advantages can be achieved if the proportion of one class present in a polymer, which is in each case selected from the structural elements of groups 1 to 7 described above, is preferably in each case > 5 mol%, particularly preferably in each case > 10 mol%.
  • the polymers may contain corresponding groups. It may preferably be provided that the polymers contain substituents, so that on average at least 2 non-aromatic carbon atoms, particularly preferably at least 4 and especially preferably at least 8 non-aromatic carbon atoms are present per recurring unit, where the average relates to the number average. Individual carbon atoms here may be replaced, for example, by 0 or S. However, it is possible for a certain proportion, optionally all recurring units, to contain no substituents which contain non-aromatic carbon atoms.
  • the substituents preferably contain at most 12 carbon atoms, preferably at most 8 carbon atoms and particularly preferably at most 6 carbon atoms in a linear chain.
  • the polymer employed in accordance with the invention as organic functional material can be a random, alternating or regioregular copolymer, a block copolymer or a combination of these copolymer forms.
  • the polymer employed as organic functional material can be a non-conjugated polymer having side chains, where this embodiment is particularly important for phosphorescent OLEDs based on polymers.
  • phosphorescent polymers can be obtained by free- radical copolymerisation of vinyl compounds, where these vinyl compounds contain at least one unit having a phosphorescent emitter and/or at least one charge-transport unit, as is disclosed, inter alia, in US 7250226 B2. Further phosphorescent polymers are described, inter alia, in JP 2007/ 211243 A2, JP 2007/197574 A2, US 7250226 B2 and JP 2007/059939 A.
  • the non-conjugated polymers contain backbone units, which are connected to one another by spacer units.
  • Examples of such triplet emitters which are based on non-conjugated polymers based on backbone units are disclosed, for example, in DE 102009023154.
  • the non-conjugated polymer can be designed as fluorescent emitter.
  • Preferred fluorescent emitters which are based on non-conjugated polymers having side chains contain anthracene or benzanthracene groups or derivatives of these groups in the side chain, where these polymers are disclosed, for example, in JP 2005/108556, JP 2005/285661 and JP 2003/338375.
  • These polymers can frequently be employed as electron- or hole-transport materials, where these polymers are preferably designed as non-conjugated polymers.
  • the functional compounds employed as organic functional materials in the solutions used in the present invention preferably have, in the case of polymeric compounds, a molecular weight M w of > 10,000 g/mol, particularly preferably > 20,000 g/mol and especially preferably > 50,000 g/mol.
  • the molecular weight Mw of the polymers here is preferably in the range from 10,000 to 2,000,000 g/mol, particularly preferably in the range from 20,000 to 1 ,000,000 g/mol and very particularly preferably in the range from 50,000 to 300,000 g/mol.
  • the solutions used in the invention may comprise all organic functional materials which are necessary for the production of the respective functional layer of the electronic device. If, for example, a hole-transport, hole-injection, electron-transport or electron-injection layer is built up precisely from one functional compound, the solution comprises precisely this compound as organic functional material. If an emission layer comprises, for example, an emitter in combination with a matrix or host material, the solution comprises, as organic functional material, precisely the mixture of emitter and matrix or host material, as described in greater detail elsewhere in the present application.
  • the solutions used in the invention may comprise further additives and processing assistants.
  • additives and processing assistants include, inter alia, surface-active substances (surfactants), lubricants and greases, additives which modify the viscosity, additives which increase the conductivity, dispersants, hydrophobicising agents, adhesion promoters, flow improvers, antifoams, deaerating agents, diluents, which may be reactive or unreactive, fillers, assistants, processing assistants, dyes, pigments, stabilisers, sensitisers, nanoparticles and inhibitors.
  • surfactants surface-active substances
  • lubricants and greases additives which modify the viscosity
  • additives which increase the conductivity additives which increase the conductivity
  • dispersants hydrophobicising agents
  • adhesion promoters adhesion promoters
  • flow improvers antifoams
  • deaerating agents deaerating agents
  • diluents which may be reactive or unreactive
  • the present invention furthermore relates to an electronic device which is obtainable by the inventive process.
  • the electronic device has at least two adjacent functional layers which are prepared by the above-mentioned inventive process for the production of an electronic device.
  • a solution used in the process of the present invention can be employed for the production of a layer or multilayered structure in which the organic functional materials are present in layers, as are required for the production of preferred electronic or opto-electronic components, such as OLEDs.
  • the solution used in the present invention can preferably be employed for the formation of functional layers on a substrate or one of the layers applied to the substrate.
  • An electronic device is taken to mean a device comprising two electrodes and at least two functional layers in between, where the functional layers comprise at least one organic or organometallic compound.
  • the electronic device is preferably an organic electronic device such as e.g. an organic electroluminescent device (OLED), a polymeric electroluminescent device (PLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic, light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic, optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), an organic electrical sensor, a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser).
  • OLED organic electroluminescent device
  • PLED polymeric electroluminescent device
  • O-IC organic integrated circuit
  • O-FET organic field-effect transistor
  • OF-TFT organic thin-film transistor
  • Active components are generally the organic or inorganic materials which are introduced between the anode and the cathode, where these active components effect, maintain and/or improve the properties of the electronic device, for example its performance and/or its lifetime, for example chargeinjection, charge-transport or charge-blocking materials, but in particular emission materials and matrix materials.
  • the organic functional material which can be employed for the production of functional layers of electronic devices accordingly preferably comprises an active component of the electronic device.
  • OLEDs Organic electroluminescent devices
  • the OLED comprises a cathode, an anode and at least two functional layers, wherein one functional layer is an emitting layer.
  • triplet emitter having the shorter-wave emission spectrum serves as co-matrix here for the triplet emitter having the longer-wave emission spectrum.
  • the proportion of the matrix material in the emitting layer in this case is preferably between 50 and 99.9% by volume, particularly preferably between 80 and 99.5% by volume and especially preferably between 92 and 99.5% by volume for fluorescent emitting layers and between 70 and 97% by volume for phosphorescent emitting layers.
  • the proportion of the dopant is preferably between 0.1 and 50% by volume, particularly preferably between 0.5 and 20% by volume and especially preferably between 0.5 and 8% by volume for fluorescent emitting layers and between 3 and 15% by volume for phosphorescent emitting layers.
  • An emitting layer of an organic electroluminescent device may also encompass systems which comprise a plurality of matrix materials (mixed-matrix systems) and/or a plurality of dopants.
  • the dopants are generally the materials whose proportion in the system is the smaller and the matrix materials are the materials whose proportion in the system is the greater.
  • the proportion of an individual matrix material in the system may be smaller than the proportion of an individual dopant.
  • the mixed-matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials.
  • One of the two materials here is preferably a material having hole-transporting properties or a wide-band-gap material and the other material is a material having electron-transporting properties.
  • the desired electron-transporting and hole-transporting properties of the mixed-matrix components may also be combined principally or completely in a single mixed-matrix component, where the further mixed-matrix component(s) fulfil(s) other functions.
  • the two different matrix materials may be present here in a ratio of 1 :50 to 1 :1 , preferably 1 :20 to 1 : 1 , particularly preferably 1 : 10 to 1 : 1 and especially preferably 1 :4 to 1 : 1.
  • an organic electroluminescent device may also comprise further layers, for example in each case one or more holeinjection layers, hole-transport layers, hole-blocking layers, electrontransport layers, electron-injection layers, exciton-blocking layers, electronblocking 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 junctions It is possible here for one or more hole-transport layers to be p-doped, for example with metal oxides, such as MoOs or WO3, or with (per)fluorinated electron-deficient aromatic compounds, and/or for one or more electron-transport layers to be n-doped. It is likewise possible for interlayers, which have, for example, an excitonblocking function and/or control the charge balance in the electroluminescent device, to be introduced between two emitting layers. However, it should be pointed out that each of these layers does not necessarily have to be present.
  • the thickness of the functional layers can preferably be in the range from 1 to 500 nm, particularly preferably in the range from 2 to 200 nm.
  • the electronic device comprises more than two functional layers.
  • the process according to the invention can preferably be employed here for the production of several pairs of adjacent functional layers.
  • the electronic device may furthermore comprise functional layers built up from further low-molecular-weight compounds or polymers which have not been applied by the process according to the present invention. These can also be produced by evaporation of low-molecular-weight compounds in a high vacuum. It may additionally be preferred to use the organic functional materials not as the pure substances, but instead as a mixture (blend) together with further polymeric, oligomeric, dendritic or low-molecular-weight substances of any desired type. These may, for example, improve the electronic or emission properties of the functional layer.
  • the organic electroluminescent device here may comprise two or more emitting layers. If a plurality of emitting layers are present, these preferably have 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 fluorescent or phosphorescent are used in the emitting layers. Very particular preference is given to three-layer systems, where the three layers exhibit blue, green and orange or red emission (for the basic structure see, for example, WO 2005/011013).
  • White-emitting devices are suitable, for example, as backlighting of LCD displays or for general lighting applications.
  • the final organic layer on the light-exit side in OLEDs can, for example, also be in the form of a nanofoam, resulting in a reduction in the proportion of total reflection.
  • OVPD organic vapour phase deposition
  • one or more layers of an electronic device according to the invention are produced from solution, such as, for example, by spin coating, or by means of any desired printing process, such as, for example, screen printing, flexographic printing or offset printing, but particularly preferably LITI (light induced thermal imaging, thermal transfer printing) or inkjet printing.
  • LITI light induced thermal imaging, thermal transfer printing
  • These layers may also be applied by a process which is different from the claimed process.
  • an orthogonal solvent can preferably be used here, which, although dissolving the functional material of a layer to be applied, does not dissolve the layer to which the functional material is applied.
  • the electronic device usually comprises a cathode and an anode (electrodes).
  • the electrodes are selected for the purposes of the present invention in such a way that their band energies correspond as closely as possible to those of the adjacent, organic layers in order to ensure highly efficient electron or hole injection.
  • the cathode preferably comprises metal complexes, metals having a low work function, metal alloys or multilayered structures comprising various metals, such as, for example, alkaline-earth metals, alkali metals, main- group metals or lanthanoids (for example Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
  • metals such as, for example, alkaline-earth metals, alkali metals, main- group metals or lanthanoids (for example Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
  • further metals which have a relatively high work function such as, for example, Ag
  • combinations of the metals such as, for example, Ca/Ag or Ba/Ag, are generally used.
  • a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor may also be preferred.
  • Suitable for this purpose are, for example, alkali-metal or alkaline-earth metal fluorides, but also the corresponding oxides (for example LiF, l_i2O, BaF2, MgO, NaF, etc.).
  • the layer thickness of this layer is preferably between 0.1 and 10 nm, particularly preferably between 0.2 and 8 nm, especially preferably between 0.5 and 5 nm.
  • the anode preferably comprises materials having a high work function.
  • the anode preferably has a potential greater than 4.5 eV vs. vacuum. Suitable for this purpose are on the one hand metals having a high redox potential, such as, for example, Ag, Pt or Au.
  • metal/metal oxide electrodes for example AI/Ni/NiOx, Al/PtOx
  • at least one of the electrodes must be transparent in order to facilitate either irradiation of the organic material (O-SCs) or the coupling-out of light (OLEDs/PLEDs, O-lasers).
  • a preferred structure uses a transparent anode.
  • Preferred anode materials here are conductive, mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive, doped polymers, such as, for example, poly(ethylenedioxythiophene) (PEDOT) and polyaniline (PANI) or derivatives of these polymers. It is furthermore preferred for a p-doped hole-transport material to be applied as hole-injection layer to the anode, where suitable p-dopants are metal oxides, for example MoOs or WO3, or (per)fluorinated electron-deficient aromatic compounds.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • conductive, doped organic materials in particular conductive, doped polymers, such as, for example, poly(ethylenedioxythiophene) (PEDOT) and polyaniline (PANI) or derivatives of these polymers. It is furthermore preferred for
  • HAT-CN hexacyanohexaazatriphenylene
  • NPD9 the compound NPD9 from Novaled.
  • a layer of this type simplifies hole injection in materials having a low HOMO energy, i.e. an HOMO energy with a large negative value.
  • all materials which are used for the functional layers in accordance with the prior art can be used in the further functional layers of the electronic device.
  • the electronic device is correspondingly structured in a manner known per se, depending on the application, provided with contacts and finally hermetically sealed, since the lifetime of such devices is drastically shortened in the presence of water and/or air.
  • the electronic devices obtainable by the process according to the invention exhibit very high stability and a very long lifetime compared with electronic devices obtained by conventional processes.
  • the functional layers obtainable using the process of the present invention exhibit excellent quality, in particular with respect to the uniformity of the functional layer. 5.
  • the functional material in the first layer does not need to include crosslinkable groups. These groups are known to reduce the lifetime of devices.
  • the first layer does not need to undergo an hard-baking or thermal crosslinking step, lower process temperatures can be employed. This reduces thermal degradation in the material which improves the device performance.
  • the determination of the solubility of a material in a solvent can be performed following ISO norm 7579:2009, which describes solubility determination by photometric or gravimetric methods.
  • ISO norm 7579:2009 describes solubility determination by photometric or gravimetric methods.
  • the photometric technique is recommended here, since the boiling points of the solvents considered are higher than 120°C.
  • Dissolution tests as described in the following were performed to identify suitable solvents that can be used as second solvent in the process of the present application.
  • the experiment was designed with particular focus on ease of reproducibility.
  • the material(s) to be analyzed (which are used to form the first functional layer) were weighed into a transparent glass flask.
  • a solvent (or a preformed solvent mixture) belonging to the list established in Table 3 was then added to the solid mixture at once, calculated to reach a final concentration of 7 g/L.
  • the mixture was stirred at 600 rpm using a magnetic stirrer and at room temperature (25°C) until complete dissolution, which was judged by visual inspection of the mixture.
  • the mixture can additionally be examined under illumination perpendicular to the line of sight to help identify undissolved particles.
  • “Time of dissolution”, also sometimes referred to as “dissolution time” tDiss mentioned in this invention was measured using a chronometer, and quantifies the time between addition of the solvent and beginning of stirring until the disappearance of the last pieces of material into solution. The dissolution rate is determined by dividing 7 g/L by the time until full dissolution was obtained (the “dissolution time”).
  • the holetransport material (HTL) polymer (polymer P1 ) as described in WO 2016/107668 A1 is spin-coated from solution.
  • the solution contains between five and fifty grams of material per liter of solvent.
  • the solvent for these formulations was toluene.
  • the formulation is prepared by weighing the solid material into the solvent.
  • the formulation is dissolved which can be facilitated by stirring the mixture for one to six hours at room temperature by using a magnetic stirrer at room temperature. If necessary temperature can be applied to assist dissolution. After full dissolution, the formulation is transferred into the glovebox and filtered under inert conditions using a 0.2 micron PTFE filter.
  • the formulation is used to spincoat a 30 nm thick layer on top of the glass slide.
  • the thickness is measured using an Alpha-step D-500 stylus-type profilometer.
  • the surface of a layer prepared using this preparation procedure is very flat and smooth. Average surface roughness (RMS) is below 1 nm.
  • the layer is annealed by placing the substrate for up to 1 hour on a hot-plate at a certain temperature, preferably more than 140°C, more preferably 140°C to 230°C. In this case, a temperature of 220°C for 30 minutes was used.
  • the stability of the deposited material layer is tested against a solvent A.
  • This solvent A is filled into a solvent stable 10 pl single-use-cartridge of the printer (Dimatix DMP-2831 , any similar drop-on-demand inkjet printer/printhead can be used).
  • the cartridge size determines the droplet volume. In this case a ten picoliter cartridge is used.
  • the printer should be operated in a vibration-free environment and should be levelled. The correct adjustment of printing conditions (detailed procedure please see Dimatix user manual) would be a droplet speed of 4 meters per second. The printing was done using a single nozzle only.
  • the substrate which was prepared according to the procedure in 1 ) is now placed onto the substrate holder of the printer.
  • the print-pattern ( Figure 1 ) is programmed to a have a specific drop volume.
  • the drop on the surface consists of nine small single droplets which are positioned very close together in a 3 x 3 matrix.
  • After printing the resulting drop looks like in Figure 2 - all the single droplets merge to form a single drop of ninety picoliter drop volume (other drop volumes can be used, but need to be kept constant over one set of experiments).
  • the image in Figure 2 can be observed using the fiducial camera of the printer. It is looking down from the top onto the substrate (schematic view, see Figure 3) parallel to the jetting direction.
  • a foto is taken using the fiducial camera ( Figure 2) and a timer is started. After five minutes soaking time the substrate is placed into a vacuum drying chamber to remove the solvent and dry the layer completely. The pressure reaches T10’ 4 mbar after sixty seconds of pumping. The substrate is fully dried for at least ten minutes. After drying the substrate is removed and the damage to the surface is quantified. There is another foto being taken using the fiducial camera of the printer again where you can already clearly identify damages to the layer. In addition, to quantify the damage to the layer, for example a tactile measurement such as Profilometry (see Figure 4) or AFM (Atomic force microscopy) can be done.
  • Profilometry see Figure 4
  • AFM Atomic force microscopy
  • KPI key performance indicator
  • Compound D1 was weighed into a glass vial to allow the preparation of an ink with 40 g/l concentration.
  • ENA and Menthoval were purged with inert gas (Nitrogen) for 20 minutes.
  • ENA was added to the solid using a glass pipette.
  • the solution was stirred with a magnetic stir bar at room temperature until complete dissolution of the solid to yield solution 1 .
  • An aliquot of solution 1 was separated into another glass vial and Menthoval was added to give solution 2 of concentration of 13.33 g/l and a solvent ratio of Menthoval/ENA of 2/1 (V/V).
  • Solution 2 and solution 3 became turbid after 4 hours and most of the solid material had precipitated within 20 hours.
  • solution 1 is long-term stable, solution 2 and 3 cannot be stored for extended periods of time.
  • Compound D1 was weighed into a glass vial to allow the preparation of an ink with 40 g/l concentration.
  • ENA and Menthoval were purged with inert gas (Nitrogen) for 20 minutes.
  • ENA was added to the solid using a glass pipette. The solution was stirred with a magnetic stir bar at room temperature until complete dissolution of the solid.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un dispositif électronique tel qu'un dispositif électroluminescent organique (OLED), deux couches fonctionnelles adjacentes présentant une interface étant formées à partir d'une solution de manière cinétiquement contrôlée. Le procédé est particulièrement adapté à la production rapide et efficace de dispositifs électroniques selon des procédés d'impression ou de revêtement. L'invention concerne en outre un dispositif électronique pouvant être obtenu selon ledit procédé.
PCT/EP2024/072131 2023-08-07 2024-08-05 Procédé de préparation d'un dispositif électronique WO2025032039A1 (fr)

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