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Definitions

• compositions for electronic devices are provided.
• the present invention relates to a composition, as well as a formulation and device containing the composition.
• organic electroluminescent devices for example OLEDs - organic light-emitting diodes or OLECs-organic light-emitting electrochemical cells
• organic semiconductors for example, in US Pat. No. 4,539,507.
• organometallic complexes which exhibit phosphorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6).
• organometallic complexes which exhibit phosphorescence
• organic electroluminescent devices are not determined solely by the emitters used.
• the other materials used such as host materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials are of particular importance. Improvements to these materials can lead to significant improvements in electroluminescent
• matrix material is also often used in the prior art if a host material for phosphorescent dopants is meant. Meanwhile, a variety of host materials have been developed for both fluorescent and phosphorescent electronic devices.
• fluorescent OLEDs according to the prior art, especially condensed aromatics, in particular anthracene derivatives, are used as host materials, in particular for blue-emitting electroluminescent devices, eg. B. 9,10-bis (2-naphthyl) anthracene
• WO 03/095445 and CN 1362464 disclose 9,10-bis (1-naphthyl) anthracene derivatives for use in OLEDs. Further anthracene derivatives are disclosed in WO 01/076323, in WO 01/021729, in WO 2004/013073, in WO 2004/018588, in WO 2003/087023 or in WO 2004/018587. Host materials based on aryl-substituted pyrenes and chrysenes are disclosed in WO 2004/016575. Host materials based on benzanthracene derivatives are disclosed in WO 2008/145239. It is desirable for high quality applications to have improved host materials available.
• ketones eg.
• phosphine oxides are used as host materials for phosphorescent emitters.
• Other host materials according to the prior art represent triazines (for example WO 2008/056746, US Pat.
• WO 2012/074210 discloses the use of fluorenes and spirobifluorenes as host materials.
• WO 2009/069442 discloses tricyclics, such as carbazole, dibenzofuran or dibenzothiophene, which are highly substituted with electron-deficient heteroaromatics (e.g., pyridine, pyrimidine or triazine). With hole-conducting groups, i. electron-rich groups, the tricycles are unsubstituted.
• JP 2009-21336 discloses substituted dibenzofurans which are substituted in position 2 with carbazole and in position with a triazine.
• WO 2011/057706 discloses occasionally substituted dibenzothiophenes and dibenzofurans as host materials, which compounds are specifically substituted with an electron-conducting and a hole-conducting group.
• Another way to improve the performance of electronic devices, particularly electroluminescent devices, is to use combinations of materials.
• US 6,392,250 B1 discloses the use of a mixture consisting of an electron transport material, a hole transport material and a fluorescent emitter in the emission layer of an OLED. With the help of this mixture, the life of the OLED over the prior art could be improved.
• US Pat. No. 6,803,720 B1 discloses the use of a mixture comprising a phosphorescent emitter and a hole and an electron transport material in the emission layer of an OLED. Both the hole and the electron transport material are small organic molecules. Furthermore, US Pat. No. 7,294,849 B2 discloses the use of a mixture containing a host material, a hole or an electron transport material and a phosphorescent emitter in the emission layer of an OLED. If a hole transport material is used in the mixture, the energy of the HOMO (highest occupied molecular orbital) of the host material must be lower than that of the hole transport material. Furthermore, then the LUMO energy (lowest unoccupied molecular orbital) of the host material must be higher than that of the phosphorescent emitter.
• HOMO highest occupied molecular orbital
• the energy of the HOMO (highest occupied molecular orbital) of the host material must be lower than that of the phosphorescent emitter. Furthermore, the LUMO energy (lowest unoccupied molecular orbital) of the host material must then be higher than that of the electron transport material.
• the host material is a wide band gap material that is characterized by a bandgap of at least 3.5 eV, where below
• compositions which are suitable for use in a fluorescent or phosphorescent OLED, and which lead to good device properties when used in an OLED, as well as the provision of the corresponding electronic device.
• compositions described in more detail below solve these objects and eliminate the disadvantages of the prior art.
• the compositions lead to very good properties of organic electronic devices, in particular organic electroluminescent devices, in particular with regard to the lifetime, the efficiency and the operating voltage.
• Electronic devices, in particular organic electroluminescent devices which contain such compositions, and the corresponding preferred embodiments are therefore the subject of the present invention.
• the surprising effects are achieved by a very specific selection of known materials.
• the present invention relates to a composition
• a composition comprising a bipolar host, a neutral co-host and a light-emitting dopant.
• Both the bipolar host and the neutral co-host are organic compounds, while the light-emitting dopant may be organic, organometallic or inorganic compounds.
• the individual connections are well known to those skilled in the art so that they can select from a variety of available connections.
• composition according to the invention is particularly suitable for use in organic electronic devices.
• Organic electroluminescent devices containing these compositions have very good efficiencies, operating voltages and significantly increased lifetimes.
• the concentration of the light-emitting dopant in the composition is preferably in the range of 0.1% by weight and 50% by weight, more preferably in the range of 1% by weight and 30% by weight and most preferably in the range of 5% by weight .-% and 20 wt .-% based on the total composition.
• the concentration of the neutral co-host in the composition is preferably in the range of 5% by weight to 70% by weight, more preferably in the range of 20% to 60% by weight, and most preferably in the range of 30 wt .-% and 60 wt .-% based on the total
• the concentration of the bipolar host in the composition is preferably in the range of 5% by weight and 70% by weight, more preferably in the range of 10% by weight and 60% by weight, and most preferably in the range of 20% by weight .-% and 50 wt .-% based on the total
• Preferred for the purposes of the present invention is when the dopant of the composition is a phosphorescent emitter.
• phosphorescent dopants or emitters typically includes compounds in which the light emission takes place by a spin-forbidden transition, for example by a transition from a triplet state or a state with an even higher spin quantum number, for example a quintet state.
• a transition from a triplet state is preferably understood.
• Particularly suitable as phosphorescent dopants or emitters are compounds which emit light, preferably in the visible range, with suitable excitation and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80.
• phosphorescent dopants compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used, in particular compounds containing iridium, platinum or copper.
• Preferred phosphorescent dopants are organic compounds and organic metal complexes, with organic metal complexes being quite preferred. Examples of the emitters described above can be found in the applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244,
• Composition meet the following conditions:
• HOMO (C) stands for the HOMO energy of the neutral co-host
• HOMO (B) and HOMO (D) correspondingly represents the HOMO energy of the bipolar host or the dopant
• the energy values given here refer to isolated compounds, and are determined as set out below.
• the highest occupied molecular orbital (HOMO) and LUMO (lowest unoccupied molecular orbital) energies as well as the triplet level of the materials are determined by quantum-chemical calculations.
• the program package "Gaussian09, Revision D.01"
• the triplet level Ti of a material is defined as the relative excitation energy (in eV) of the triplet state with the lowest energy resulting from the quantum chemical energy calculation.
• composition which is characterized in that at least one of the following two
• the composition comprises a bipolar host, a neutral co-host, and a light-emitting dopant, which is preferably a phosphorescent emitter, more preferably an organic phosphorescent emitter, characterized in that the following conditions are satisfied max ⁇
• composition according to the aforementioned further embodiment which is characterized in that at least one of the following two conditions is satisfied max ⁇
• bipolar host is one which contributes significantly to both the electron transport and the hole transport in the mixture used in the component used.
• this is achieved in that a material is selected, (a) in that due to its energy level positions in
• One skilled in the art can use a large number of known hosts to select suitable bipolar hosts and combine them with similarly known emitters with matching energy level gauges.
• Hybrid systems are characterized by having both at least one electron transporting group and at least contain a hole-transporting group, which are generally groups that achieve by their electron richness or their electron poverty a suitable for hole injection HOMO or a suitable for electron injection LUMO.
• Bipolarity is not a property of a single material, but is achieved by appropriate properties relative to other materials present in the mixture. In the examples, it will be shown later that a material may once be a bipolar host and once a neutral co-host, depending on the other materials of the composition (compound 13t).
• Preferred bipolar hosts are selected from the group of pyridines, pyrimidines, triazines, benzimidazoles, carbazoles, indenocarbazoles, indolocarbazoles, 1, 10-phenanthrolines, 1, 3,4-oxadiazoles, phosphine oxides, phenylsulfonyls, ketones, lactams and triarylamines, wherein the triazines , Pyrimidines, benzimidazoles, carbazoles, indenocarbazoles, indolocarbazoles, ketones, lactams and triarylamines are quite preferred.
• bipolar hosts are selected from the group of triazines, benzimidazoles, carbazoles, indenocarbazoles, lactams and triarylamines, the triazines, carbazoles, indenocarbazoles and lactams being particularly preferred.
• the relative locations of the frontier orbitals are critical to the beneficial technical effects.
• the components specified here are therefore exemplary in nature.
• Pyridines which are useful as bipolar hosts are, for example, disclosed in Adv. Mater., 2011, 23, 3876-3895.
• the pyridines disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Pyrimidines which are suitable as bipolar hosts are, for example, in WO 20 1/057706 A2, in WO2011 / 132684A1 or in EP 12008332.4 disclosed.
• the pyrimidines disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Triazines which are useful as bipolar hosts are, for example, disclosed in WO 2011/057706 A2, EP 12008332.4 or in Adv. Mater., 2011, 23, 3876-3895.
• the triazines disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Benzimidazoles useful as bipolar hosts are, for example, disclosed in Adv. Mater., 2011, 23, 3876-3895 or WO2010 / 107244 A2. 0
• the benzimidazoles disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Carbazoles which are useful as bipolar hosts are, for example, disclosed in WO 2011/057706 A2, EP 12008332.4 or in Adv. Mater., ⁇ 2011, 23, 3876-3895.
• the carbazoles disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Indenocarbazoles useful as bipolar hosts are, for example, disclosed in EP 12008332.4 or in WO 2011/000455. The one in it
• Indenocarbazoles disclosed also represent very preferred bipolar hosts within the meaning of the present invention.
• Indolocarbazoles useful as bipolar hosts are, for example, disclosed in WO 2008/056746 A1.
• the indolocarbazoles disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• 10-phenanthrolines useful as bipolar hosts are, for example, disclosed in Adv. Mater., 2011, 23, 3876-3895.
• the 1,10-phenanthrolines disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Phosphine oxides useful as bipolar hosts are, for example, disclosed in Adv. Mater., 2011, 23, 3876-3895.
• the phosphine oxides disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Phenylsulfonyls which are useful as bipolar hosts are, for example, disclosed in Adv. Mater., 20 1, 23, 3876-3895.
• the phenylsulfonyls disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Ketones which are suitable as bipolar hosts are disclosed, for example, in WO 2007/137725 A1 or in WO 2010/136109 A1.
• the ketones disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Lactams suitable as bipolar hosts are disclosed, for example, in WO 2013/064206.
• the lactams disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Triarylamines useful as bipolar hosts are disclosed in, for example, WO2007 / 137725 A1, WO 2011/000455 or Adv. Mater., 2011, 23, 3876-3895.
• the triarylamines disclosed therein also represent very preferred bipolar hosts within the meaning of the present invention.
• Hybrid systems are characterized by containing both at least one electron transporting group (ET) and at least one hole transporting group (HT).
• the bipolar host of the composition according to the invention is therefore in a further preferred embodiment of the present invention, a hybrid system containing both at least one electron-transporting group (ET) and at least one hole-transporting Group (HT).
• ET electron-transporting group
• HT hole-transporting Group
• the bipolar host is a hybrid system which is selected from the group consisting of the HT / N-containing heterocycle hybrid systems, HT / benzimidazole hybrid system, HT / 1, 10-phenanthroline. Hybrid systems, HT / 1, 3,4-oxadiazole hybrid systems, HT / phosphine oxide hybrid systems, HT / phenylsulfonyl hybrid systems, HT / ketone hybrid systems and HT / lactam hybrid systems.
• the notation HT / benzimidazole is intended to mean that the bipolar host contains at least one hole-transporting group (HT) and at least one electron-transporting group, one of the electron-transporting groups being a benzimidazole.
• Preferred N-containing heterocycles are the pyridines, pyrimidines and triazines, the triazines being very preferred groups.
• hybrid systems for bipolar hosts are HT / pyridine hybrid systems, HT / pyrimidine hybrid systems, HT / triazine hybrid systems, HT / benzimidazole hybrid systems, most preferred
• HT / triazine hybrid systems or HT / benzimidazole hybrid systems, and particularly preferred are HT / triazine hybrid systems.
• bipolar hosts are carbazole / ET hybrid systems, indenocarbazole / ET hybrid systems, indolocarbazole / ET hybrid systems, carbazole-carbazole / ET hybrid systems, indenocarbazole-carbazole / ET hybrid systems and amine / ET hybrid systems wherein the carbazole / ET - Hybrid systems are very preferred.
• Very particularly preferred hybrid systems are the carbazole / triazine hybrid systems, indenocarbazole / triazine hybrid systems, indolocarbazole / triazine hybrid systems, carbazole-carbazole / triazine hybrid systems, indenocarbazole-carbazole / triazine hybrid systems and amine / triazine hybrid systems ,
• the neutral co-host of the composition of the present invention like the other two components (bipolar host and light-emitting dopant), is also by the relative locations of its frontier orbitals
• neutral neutrals should also be noted that neutrality is not a property of a single material, but is achieved by appropriate properties relative to other materials present in the mixture (see Compound 13t in the Examples).
• Examples of preferred neutral co-hosts are, for example, disclosed in WO 2010/108579, EP 12008584.0, and WO 2009/021126 A9,.
• the neutral co-hosts are preferably aromatic or heteroaromatic hydrocarbons, the number of heteroaromatic rings in the neutral co-host being smaller than the number of aromatic rings. Most preferred is when the number of heteroaromatic rings in the neutral co-host is at most 2. It is particularly preferred if at most one ring of the neutral co-host is a heteroaromatic ring.
• a benzimidazole for example, contains an aromatic ring
• Benzene and a heteroaromatic ring (imidazole).
• a carbazole contains two aromatic rings (two benzenes) and one heteroaromatic ring (pyrrole).
• a spirobifluorene contains 4 aromatic rings (4 benzenes).
• the neutral co-host preferably contains 6 or less, more preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, most preferably 2 or less, still more preferably 1 or less, most preferably none at all
• preferred neutral hosts may also be those which in other combinations are charge transporting, e.g. used as electron-transporting hosts.
• charge transporting e.g. used as electron-transporting hosts.
• These include, for example, lactams (e.g., WO 2013/064206), pyrimidines (e.g., WO 2010/136109 A1), triazines (e.g., WO 2010/136109 A1), and benzimidazoles (e.g., Optical Materials 35 (2013) 2201-2207).
• Some exemplary, more preferred neutral co-hosts are those of the folloWing overview.
• the composition of the present invention may contain other organic functional materials in addition to said materials, bipolar host, neutral co-host, and light-emitting dopants.
• the present invention therefore also relates to a composition which, in addition to the three components mentioned above, contains further organic functional materials which are preferably selected from the group of hole injection materials, hole transport materials, hole blocking materials, host materials, emitter materials, electron blocking materials, electron transport materials and electron injection materials. It does not give the expert any difficulty to select from a variety of materials known to him.
• composition is another
• functional material contains another host material.
• the further host material is another bipolar host material within the meaning of this application. In a further preferred embodiment, the further host material is another neutral host material within the meaning of this application.
• the further host material is a hole-transporting host material. In a further preferred embodiment, the further host material is a
• Preferred other host materials are aromatic amines,
• triarylamines in particular triarylamines, e.g.
• carbazole derivatives e.g CBP, ⁇ , ⁇ -biscarbazolylbiphenyl
• WO 2005/039246 e.g. WO 2005/039246
• US 2005/0069729 JP 2004/288381
• EP 1205527 WO 2008/086851
• bridged carbazole derivatives e.g. B. according to
• WO 2011/088877 and WO 2011/128017 indenocarbazole derivatives, e.g. B. according to WO 2010/136109 and WO 2011/000455, Azacarbazolderivate, z. B. according to EP 1617710, EP 16177, EP 1731584, JP 2005/347160, Indolocarbazolderivate, z. B. according to WO 2007/063754 or
• WO 2010/006680 phosphine oxides, sulfoxides and sulfones, z. B. according to WO 2005/003253, oligophenylenes, bipolar host materials, eg. B. according to WO 2007/137725, silanes, z. B. according to WO 2005/111172, azaborole or boronic esters, z. B. according to WO 2006/117052, triazine derivatives, z. According to WO 20/015156, WO 2007/063754 or WO 2008/056746,
• Zinc complexes e.g. B. according to EP 652273 or WO 2009/062578,
• Aluminum complexes e.g. B. BAIq, diazasilol and tetraazasilol derivatives, z. B. according to WO 2010/054729, diazaphosphole derivatives, z. B. according to
• WO 2010/054730 and aluminum complexes, for. B. BAIQ.
• the concentration of the further host material in the composition is preferably in the range of 10% by weight and 50% by weight, more preferably in the range of 10% by weight and 30% by weight, and most preferably in the range of 10 wt .-% and 20 wt .-% based on the total composition.
• the composition according to the invention contains one or more further light-emitting dopants, which are phosphorescent emitters.
• the composition contains one or two further light-emitting dopants, wherein it is particularly preferred if the composition contains a further light-emitting dopant.
• the above-mentioned phosphorescent dopants are suitable.
• a dopant then has a shorter wavelength emission spectrum when its peak emission in the electroluminescence spectrum is shifted to a shorter wavelength compared to the peak emission in the
• blue (400-500 nm) or green (501-560 nm) emitting, phosphorescent dopants can be used as co-hosts for red-emitting, phosphorescent dopants.
• blue-emitting, phosphorescent dopants can be used as co-hosts for green-emitting, phosphorescent dopants. This is advantageous for life, efficiency and operating voltage of the corresponding organic
• Electroluminescent devices are Electroluminescent devices.
• compositions are used in which the predominant portion of the emission in electroluminescence emanates from the longer-wavelength phosphorescent dopant.
• the proportion of emission in the electroluminescence of a dopant predominates when at least 70%, preferably at least 80% and most preferably at least 90% of the area under the electroluminescence emission spectrum is due to this dopant of the composition.
• Very particular preference is given here to compositions in which only the longer-wavelength, phosphorescent dopant contributes to the emission into electroluminescence.
• the term "exclusive" means that at least 99% of the area under the electroluminescent emission spectrum is due to that dopant of the composition.
• a high proportion of emission from the longer-wavelength, phosphorescent dopant can be achieved, for example, by a high relative concentration of this emitter and / or low steric Shielding of both emitters involved and / or suitable energy level positions leading to preferential exciton formation on the longer wavelength, phosphorescent dopant.
• the concentration of the shorter-wavelength light-emitting phosphorescent dopant in the composition is preferably in the range of 1 wt% and 40 wt%, more preferably in the range of 3 wt% and 30 wt%, and all more preferably in the range of 5 wt .-% and 20 wt .-% based on the total composition.
• longer wavelength light-emitting phosphorescent dopants in the composition preferably in the range of 1 wt .-% and 30 wt .-%, more preferably in the range of 5 wt .-% and 20 wt .-% based on the total composition.
• composition of two light-emitting, phosphorescent dopants is used in which both dopants significantly to the emission in
• a dopant contributes significantly to the emission in electroluminescence if its contribution to the emission in the electroluminescence is at least 10%, preferably at least 20% and more preferably at least 30% of the area under the electroluminescent emission spectrum is on said dopant of the composition.
• a significant proportion of emission from the shorter-wavelength phosphorescent dopant can be achieved, for example, by a low to very low relative concentration of the longer-wavelength phosphorescent dopant and / or or high steric shielding of both involved emitters and / or suitable energy level positions leading to preferential exciton formation on the shorter wavelength, phosphorescent dopant.
• the concentration of the shorter wavelength further light-emitting dopant in the composition is preferably in the range of 1 wt% and 40 wt%, more preferably in the range of 5 wt% and 30 wt%, and most particularly preferably in the range of 8 wt .-% and 20 wt .-% based on the total composition.
• the concentration of the longer wavelength light-emitting dopant in the composition is preferably in the range of 0.1% by weight and 10% by weight, more preferably in the range of 0.1% by weight and 3% by weight based on the whole Composition.
• these dopants preferably have several total
• Emission maxima between 380 nm and 750 nm, so that total white emission results.
• Particularly preferred is a combination of blue, green and orange or red emission.
• the concentration of the shortest wavelength light-emitting dopant in the composition is preferably in the range of 1 wt% and 40 wt%, more preferably in the range of 5 wt% and 30 wt%, and most preferably in the range of 8 wt .-% and 20 wt .-% based on the total composition.
• the concentration of the light emitting dopant having the next higher emission wavelength in the composition is preferably in the range of 0.1 wt% to 10 wt%, more preferably in the range of 0.5 wt% to 3 wt% on the entire composition.
• the concentration of the longest-wavelength light-emitting dopant in the composition is preferably in the range of 0.01% by weight and 5% by weight, more preferably in the range of 0.1% by weight and 1% by weight based on the total
• the composition in addition to the bipolar host, the neutral co-host and the light-emitting dopant, the composition does not contain any organic functional materials, it being particularly preferred that the composition of the invention be composed only of the bipolar host, the neutral co-host and the light-emitting dopant and contains no other organic or inorganic constituents.
• present invention contains the composition in addition to the bipolar host, the neutral co-host, the light-emitting dopant and the other host material none of the above-mentioned organic functional materials, wherein it is particularly preferred that the composition according to the invention only from the bipolar host, the neutral co-host, the light-emitting dopant and the other host material and contains no other organic or inorganic constituents.
• the composition does not contain any of the above-mentioned organic functional materials, with the composition according to the invention being particularly preferred consists only of the bipolar host, the neutral co-host, the light-emitting dopant and the further light-emitting dopant and no further
• compositions according to the invention can be used in electronic devices, in particular in organic electroluminescent devices.
• the components of the compositions can be processed by vapor deposition or from solution. If the compositions are applied from solution, at least one additional solvent is required.
• the processing from solution has the advantage that the layer containing the composition according to the invention can be applied very simply and inexpensively. This technique is particularly suitable for the mass production of organic electronic devices.
• the present invention therefore also relates to a formulation comprising a composition according to the invention and at least one
• Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) Fenchone, 1,2,3,5-tetramethylbenzene, 1, 2,4,5-tetra- methylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3 , 4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin,
• the present invention therefore relates to the use of a formulation according to the invention for producing an electronic device, in particular an organic electroluminescent device, characterized in that the formulation is used to obtain an emission layer of the device from solution
• the present invention also relates to the use of the inventive compositions in an organic solvent
• the present invention also relates to an organic compound
• OICs organic integrated circuits
• OFETs organic field effect transistors
• OTFTs organic thin film transistors
• O electroluminescent devices organic solar cells (OSCs)
• OSCs organic solar cells
• organic optical detectors organic photoreceptors, and the organic electroluminescent device are most preferred.
• OLETs organic light-emitting transistors
• OFQDs organic field quench devices
• OLEDs organic light-emitting electrochemical cells
• O-lasers organic laser diodes
• OLEDs organic light-emitting Diodes
• the organic electroluminescent device may contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, emitting layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, interlayers, charge generation layers (IDMC 2003, Taiwan; OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or Organic or Inorganic P / n transitions. It should be noted, however, that not necessarily each of these layers must be present.
• the sequence of layers of organic electroluminescent devices is preferably the following:
• the organic electroluminescent device according to the invention may contain a plurality of emitting layers.
• these emission layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie, in the emitting layers
• emissive compounds that can fluoresce or phosphoresce and that emit blue or yellow or orange or red light. Particularly preferred
• Three-layer systems ie systems with three emitting layers, the three layers showing blue, green and orange or red emission (for the basic structure, see, for example, WO 2005/011013). It should be noted that for the production of white light, instead of a plurality of color-emitting emitter compounds, a single emitter compound which can be used in a broad range may also be suitable
• Wavelength range emitted Wavelength range emitted.
• composition according to the invention is also suitable in particular for use in organic electroluminescent devices, as described, for example, in US Pat.
• an additional blue emission layer is vapor-deposited over all pixels, even those with a different color from blue. It is surprisingly found that the inventive
• compositions when used for the red and / or green pixel, together with the vapor-deposited blue
• Suitable charge transport materials as used in the hole injection or hole transport layer or in the electron blocking layer or in the
• Electron transport layer of the organic electroluminescent device according to the invention can be used, for example, those disclosed in Y. Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010
• Compounds or other materials, as used in the prior art in these layers are suitable as materials for the electron transport layer.
• materials for the electron transport layer it is possible to use all materials as used in the prior art as electron transport materials in the electron transport layer.
• aluminum complexes, for example Alq3, are suitable.
• Zirconium complexes for example Zrq-t, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.
• WO 2004/028217, WO 2004/080975 and WO 2010/072300 are disclosed.
• hole transport materials are materials which can be used in a hole transport, hole injection or electron blocking layer, indenofluorenamine derivatives (for example according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (for example according to WO 01/049806), amine-fused aromatics (for example according to US Pat. No.
• the cathode of the electronic device are low workfunction metals, metal alloys or multilayer structures of various metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (eg Ca, Ba, Mg, Al, In, Mg, Yb, Sm, Etc.). Also suitable are alloys of an alkali or alkaline earth metal and silver, for example an alloy of magnesium and silver. In multilayer structures can also be added to the metals mentioned other metals are used which have a relatively high work function, such as. As Ag or Al, which then usually combinations of metals, such as Ca / Ag, Mg / Ag or Ba / Ag are used. It may also be preferred to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. For example, alkali metal or
• Alkaline earth metal fluorides but also the corresponding oxides or
• Carbonates in question eg LiF, L12O, BaF2, MgO, NaF, CsF, CS2CO3, etc.
• lithium quinolinate LiQ
• the layer thickness of this layer is preferably between 0.5 and 5 nm.
• the anode high workfunction materials are preferred.
• the anode has a work function greater than 4.5 eV. Vacuum up.
• metals with a high redox potential such as Ag, Pt or Au, are suitable for this purpose.
• metal / metal oxide electrodes eg Al / Ni / NiOx, Al / PtOx
• at least one of the electrodes must be transparent or
• anode materials are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive doped polymers.
• the anode can also consist of several layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide,
• Molybdenum oxide or vanadium oxide are examples of Molybdenum oxide or vanadium oxide.
• the electronic device is structured according to the application (depending on the application), contacted and finally sealed, since the life of the devices according to the invention at
• the electronic device according to the invention is characterized in that one or several layers are coated with a sublimation process.
• the materials in vacuum sublimation are evaporated at an initial pressure less than 10 -5 mbar, preferably less than 10 "6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 7 mbar.
• an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
• the materials are applied at a pressure between 10 -5 mbar and 1 bar.
• OVJP Organic Vapor Jet Printing
• the materials are applied directly through a nozzle and thus structured (for example, BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
• an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
• any printing process such as screen printing, flexographic printing, Nozzle Printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing), are produced.
• LITI Light Induced Thermal Imaging, thermal transfer printing
• ink-jet printing ink jet printing
• the invention thus further provides a method for producing the inventive electronic device, characterized
• the devices according to the invention can be used in a very versatile manner.
• the electroluminescent devices can be used in displays for televisions, mobile phones, computers and cameras.
• the devices can also be used in lighting applications.
• electroluminescent devices, for. B. in OLEDs or OLECs, containing at least one of the composition according to the invention in medicine or cosmetics are used for phototherapy.
• diseases psoriasis, atopic dermatitis, inflammation, acne, skin cancer, etc.
• the light-emitting devices may be used to keep beverages, foods, or foods fresh, or to sterilize devices (eg, medical devices).
• the present invention also provides a device comprising at least one organic electronic device according to the invention, preferably an organic electroluminescent device, wherein the device is preferably a television, a mobile phone or a smartphone, a computer (eg desktop computer, tablet, notebook) or a photo camera is acting.
• the device is preferably a television, a mobile phone or a smartphone, a computer (eg desktop computer, tablet, notebook) or a photo camera is acting.
• the present invention furthermore relates to an organic electroluminescent device, preferably an OLED or OLEC, and very particularly preferably an OLED containing a composition according to the invention for use in medicine for phototherapy.
• a further preferred subject of the present invention relates to an electronic device, preferably an organic electroluminescent device according to the invention, very preferably an OLED or OLEC and very particularly preferably an OLED for use in the phototherapeutic treatment of skin diseases.
• Another very preferred object of the present invention relates to an electronic device according to the invention, preferably an organic electroluminescent device according to the invention, entirely preferably an OLED or OLEC and very particularly preferably an OLED for use for the phototherapeutic treatment of
• Psoriasis atopic dermatitis
• inflammatory diseases vitiligo
• wound healing atopic dermatitis
• skin cancer atopic dermatitis
• the present invention also relates to the use of the organic electroluminescent devices according to the invention, very preferably an OLED or OLEC and very particularly preferably an OLED in cosmetics, preferably for the treatment of acne, aging skin, and cellulites.
• composition according to the invention in the
• organic electroluminescent devices often contain further layers in addition to an anode, cathode and an emission layer. These further layers may contain organic and / or inorganic constituents.
• HTL hole transport layer
• HTM hole transport materials
• HTL hole transport layer
• HTM all hole transport materials which are familiar to the person skilled in the art can be used for this purpose.
• Hole transport materials which are typically used for this purpose and which are also preferred hole transport materials in the context of the present invention are selected from the group of the triarylamines, carbazoles, indenocarbazoles, indolocarbazoles and the aromatic silylamines.
• Emission layer and the cathode is directly adjacent to the emission layer electron transport layer (ETL) is present.
• ETL emission layer electron transport layer
• ETM electron transport materials
• Electron transport materials which are typically used for this purpose and which are also preferred electron-transport materials in the context of the present invention are selected from the group of pyridines, pyrimidines, triazines, benzimidazoles, metal hydroxyquinolines,
• LUMO (ETM) represent the absolute magnitudes of the LUMO energies of the bipolar host in the emission layer and those of the electron transport material in the adjacent ETL.
• compositions according to the invention or the
• compositions according to the invention are very suitable for use in an emission layer and show improved
• compositions of the invention in electronic devices leads to significant increases in the lifetimes of the devices. 3.
• the compositions can be easily processed and are therefore very well suited for mass production in commercial application.
• Embodiments of the present invention are to be considered. For these features, independent protection may be desired in addition to or as an alternative to any presently claimed invention.
• Step 1
• 1, 1'-bis (diphenylphosphino) ferrocene are placed in 1300 ml of toluene and heated for 5 hours under reflux. After cooling to
• Reaction mixture is cooled to 0 ° C and added in portions over 30 minutes with 35.6 g (200 mmol) / V-bromosuccinimide. The cooling is removed, the mixture stirred for 16 hours and then concentrated to about 250 ml. With vigorous stirring 1000 ml of water are added, the solid formed is filtered off with suction and boiled twice with 800 ml of ethanol. After drying in vacuo remain 47.1 g (130 mmol, 65% of theory) of the product as a colorless solid with a purity of about 98% by 1 H-NMR.
• the following compounds can be prepared:
• Example 3a 17.9 g (114 mmol) of bromobenzene, 30.5 g (317 mmol) of sodium ferf-butylate, 0.5 g (2.2 mmol) of palladium (II) acetate and 4.2 ml of tri-feri-butyl-phosphine solution ( 1M in toluene) are placed in 1500 ml of p-xylene and heated for 16 hours under reflux. After cooling to room temperature, the organic phase is separated from solid components, washed three times with 200 ml of water and then freed from the solvent on a rotary evaporator. The residue is mixed with about 300 ml
• Step 1
• Step 1
• Lithium acetate are heated with 4800 hours of 100% acetic acid to 135 ° C with exclusion of light.
• the acetic acid is removed in vacuo, the residue with 200 ml of ethanol and dispersed.
• the solid is filtered off, washed with water and ethanol, dried in vacuo and then hot-extracted twice over silica gel with dichloromethane.
• the residue is recrystallized in DMF, dried in vacuo and fractionated at 5 * 10 5 mbar and fractionated at 360 ° C. There are obtained 11.3 g (14 mmol) of a yellow powder in 99.8% purity by HPLC.
• compositions according to the invention are provided.
• compositions according to the invention A selection of compositions according to the invention and
• Blend components can take on different roles (bipolar host, electron-transporting host, neutral co-host, etc.).
• solution-based and vacuum-based deposited layers within an OLED are combined so that the processing up to and including the emission layer from solution and in the subsequent layers (hole blocking layer and electron transport layer) takes place from the vacuum.
• the general methods described above are adapted and combined as follows to the conditions described here (layer thickness variation, materials) and combined:
• the structure is as follows:
• HTL hole transport layer
• EML emission layer
• HBL hole blocking layer
• ETL Electron Transport Layer
• the substrate used is glass flakes coated with structured ITO (indium tin oxide) 50 nm thick.
• structured ITO indium tin oxide
• PEDOT PSS (poly (3,4-ethylenedioxy-2,5-thiophene): polystyrene sulfonate, obtained from Heraeus Precious Metals GmbH & Co. KG, Germany).
• PEDOTPSS is spun in air from water and subsequently heated in air at 180 ° C for 10 minutes to remove residual water. On this coated
• the hole transport layer used is crosslinkable.
• the hole transport polymer is dissolved in toluene.
• the typical solids content of such solutions is about 5 g / l, if, as here, the typical for a device layer thickness of 20 nm is to be achieved by spin coating.
• the layers are spin-coated in an inert gas atmosphere, in this case argon, and baked at 180 ° C. for 60 minutes.
• the emission layer is always composed of the host material (s) and an emitting dopant (dopant, emitter).
• TMM-A (92%): Dotand (8%) here means that the material TMM-A is present in a weight fraction of 92% and dopant in a weight fraction of 8% in the emission layer.
• Emission layer is dissolved in toluene or optionally chlorobenzene.
• the typical solids content of such solutions is about 18 g / l, if, as here, the typical for a device layer thickness of 60 nm is to be achieved by spin coating.
• the layers are spin-coated in an inert gas atmosphere, in the present case argon, and baked at 160 ° C. for 10 minutes.
• the materials for the hole blocking layer and electron transport layer are thermally evaporated in a vacuum chamber.
• the electron transport layer consist of more than one material, the other by co-evaporation in a certain volume fraction be mixed.
• An indication such as ETM1: ETM2 (50%: 50%) here means that the materials ETM1 and ETM2 are present in a volume fraction of 50% each in the layer.
• the materials used in the present case are shown in Table 4.
• the cathode becomes 100 nm due to the thermal evaporation
• the OLEDs are characterized by default.
• the electroluminescence spectra, current-voltage-luminance characteristics are determined assuming a lambertian radiation characteristic and the (operating) life. Key figures are determined from the IUL characteristics such as the operating voltage (in V) and the external quantum efficiency (in%) at a specific brightness.
• LD80 @ 8000 cd / m 2 is the lifetime until the OLED has dropped to 80% of the initial intensity, ie 6400 cd / m 2 , at a starting brightness of 8000 cd / m 2 . Accordingly LD80 @ 10,000 cd / m 2, the durability to the OLED is dropped at an initial luminance of 10,000 cd / m 2 to 80% of the initial intensity, so to 8000 cd / m 2.
• OLED materials can be vacuum evaporated. In the examples discussed below, only vacuum-based applied layers were used. The above-described general methods are adapted to the circumstances described here (layer thickness variation, materials).
• the OLEDs have in principle the following layer structure: substrate / hole transport layer (HTL) / optional intermediate layer (IL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) and finally a cathode.
• the cathode is formed by a 100 nm thick aluminum layer.
• Table 7 The exact structure of the OLEDs and the resulting results are shown in Table 7.
• the auxiliary materials needed to make the OLEDs are shown in Table 6; used
• compositions are shown in Table 3.

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