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  • H10K71/10—Deposition of organic active material
  • H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
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  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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  • H10K71/10—Deposition of organic active material
  • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
  • H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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  • H10K85/30—Coordination compounds
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  • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
  • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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  • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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  • H10K2101/10—Triplet emission
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  • H10K71/851—Division of substrate

Definitions

• the present invention relates to a method for
• the present invention further relates to a radiation-emitting organic-electronic device that can be produced by this method.
• the losses are reduced by at least one of said loss channels.
• the method comprises
• Molecular structure and a matrix material are provided; B) a first electrode layer is deposited on a substrate
• thermodynamic control is an anisotropic alignment of the molecules of the phosphorescent emitter
• the used Molecules form not a substantially spherical molecular structure, but a rather elongated molecular structure.
• the phosphorescent emitters in particular have at least two different different ligands (in particular ligands which differ with respect to their atoms coordinating with the central atom) or have a square-planar environment of the central atom.
• a first layer which is arranged or applied "on" a second layer may mean that the first layer is arranged or applied directly in direct mechanical and / or electrical contact with the second layer be designated indirect contact, in which further layers between the first layer and the second layer are arranged.
• thermodynamic control is understood to mean that during the deposition of the emitter molecules and the molecules of the matrix material no arbitrary alignment of the deposited molecules takes place, but rather that the alignment takes place at least partially in a preferred direction. This is accompanied by the fact that the transition dipole moments of the emitter molecules as a whole also have an anisotropic distribution within the matrix
• thermodynamic control thus requires that unlike the kinetic Do not control an emitter molecule automatically in the
• Position is "frozen” in the first time in which it interacts with the surface on which it is deposited, but rather that during the deposition or in a later step, a reorientation can take place, in which an alignment of adjacent molecules takes place, with a thermodynamically more favorable configuration can be taken.
• Emitter molecules are particularly possible if both for the emitter and for the matrix material
• the emitter layers can be produced by the output ⁇ materials having an anisotropic molecular structure in which the individual emitter molecules, and thus the transition dipole moments of the emitting molecules have a preferred orientation.
• the emitter molecules are substantially parallel
• Preferred orientation of the emitter molecules which are preferably aligned parallel to the substrate surface, can only to a limited extent an interaction of the in the
• Electromagnetic field with the plasmon of the metal layer is Electromagnetic field with the plasmon of the metal layer.
• a plasmon is understood to mean a charge carrier density oscillation in the metal layer of the first electrode.
• an electromagnetic field generated by a recombinant exciton can excite free charge carriers, in particular electrons, in the metal layer of an electrode to charge carrier density oscillations.
• this may be the recombination of an exciton
• Recombination energy can at least partially pass to the plasmon.
• plasmons (more precisely:
• Extension plane of a surface of the metal layer of an electrode occur on this surface.
• thermodynamic control is carried out in step C) by selecting a growth rate which is less than or equal to 0.5 nm / s.
• the growth rate may be less than 0.2 nm / s and is often less than 0.1 nm / s. Often the growth rate is less than 0.05 nm / s; she can
• the deposition time for a 10 nm thick emitter layer is then about 200 s.
• the rate of growth is to be understood as the rate at which the first electrode layer is used in step C)
• Emitter layer is deposited.
• the amount of substance deposited in this case is essentially identical to the amount of substance evaporated from a receiver, for example.
• a particularly slow growth rate can be selected, for example, if the materials for the emitter layer do not allow an increased temperature of the substrate to be coated (compare the following embodiment).
• thermodynamic control in step C) is achieved in that after and / or during the deposition step (step C)) the deposited layer (in particular before the
• Depositing further layers is subjected to a temperature treatment.
• the emitter layer is brought to a temperature which is elevated in relation to room temperature or kept at such a temperature. On the deposited layer can thus either during the
• the layer is thus brought into a state in which a reorientation, in particular the
• Emitter molecules is possible, so that alignment of the emitter molecules can take place. This aligned state can then be frozen by cooling subsequently.
• the temperature treatment can be carried out in particular by the emitter layer or the layer adjacent to the substrate (for example via a heated layer)
• Substrate is heated.
• the emitter layer can thereby
• the selection of the matrix molecules and of the emitter molecules can therefore in particular be such that no reorientation of the emitter molecules takes place at room temperature
• thermodynamic control can also be done by both a slow rate of growth (as above
• the phosphorescent emitter having an anisotropic molecular structure is selected from iridium complexes, platinum complexes and
• Palladium complexes or mixtures thereof Palladium complexes or mixtures thereof.
• the iridium complexes provide very good quantum yields when used as emitter molecules in organic
• platinum and palladium complexes also give very good results since, because of the predominantly square-planar coordination in the presence of a corresponding matrix material, these very easily align themselves substantially parallel to one another and to the substrate surface
• the phosphorescent emitters are not limited to these metal complexes; Rather, there are others as well
• Metal complexes such as lanthanide complexes (e.g.
• Europium complexes or else gold, rhenium, rhodium, ruthenium, osmium or zinc complexes.
• complexes of the following formula are selected as the iridium complexes according to the application:
• CnN is an at least bidentate ligand which forms a metallacyclic ring with the metal atom.
• the term "CnN” further stands for a ligand in which the iridium atom is coordinated on the one hand by a carbon atom and on the other hand by a nitrogen atom. Both the carbon atom and the nitrogen atom are usually in an aromatic
• the ring coordinated via the nitrogen atom to the iridium atom is usually a heterocyclic ring which, in addition to the nitrogen atom, contains no further or only one further heteroatom (in particular a further nitrogen atom or an oxygen atom) ,
• the two CnN ligands can together also form a tetradentate ligand; it is also possible to bridge the other ligand (an acetylacetonate derivative) with one or both of the CnN ligands.
• the radicals R 1, R 2 and R 3 independently of one another are branched, unbranched condensed and / or
• ring-shaped alkyl radicals and / or aryl radicals it may be in particular the acetylacetonate itself.
• Both the aryl radicals and the alkyl radicals can be completely or partially functionalized (for example ether groups (for example metoxy, ethoxy or propoxy groups), ester groups, amide groups or else carbonate groups)
• the radical R2 can also be hydrogen or Be fluorine. Frequently, the radicals R 1 and R 2 are methyl, ethyl or propyl and optionally also phenyl. R2 will often be hydrogen or fluorine.
• the said ethyl, methyl, propyl and phenyl groups are either unsubstituted or have one or more fluorine substituents. The latter compounds are synthetically easy to obtain or commercially available. The introduction of fluorine substituents usually facilitates the
• the ligand CnN with the iridium atom forms a five-membered or six-membered metallacyclic ring.
• the ligand CnN may be phenylpyridine, phenylimigazole, phenyloxazole, benzylpyridine, benzylimidazole or benzyloxazole, or a ligand having one of said compounds as a backbone, thus containing the corresponding heterocyclic backbone, but with additional substituents, bridging or annelated rings available.
• substituents in particular fluorine atoms come into consideration, since by substitution with one or more
• Aryl radicals and functional groups for example, ether groups (such as metoxy, ethoxy or propoxy groups), ester groups, amide groups or carbonate groups) may be contained.
• ether groups such as metoxy, ethoxy or propoxy groups
• ester groups such as metoxy, ethoxy or propoxy groups
• amide groups or carbonate groups may be contained.
• the ligand CnN has at least three at least partially fused aromatic
• At least partially condensed here means that one or more condensed ring systems can be present in the ligand CnN.
• the ligand may be formed by three fused aromatic rings to which a phenyl group or a benzyl group is attached.
• the fused aromatic ring can be attached to both the
• Aromatics may be condensed or to both rings
• II iridium
• Ir (mppy) 2 (acac) (bis [2- (p-tolyl) pyridine] acetylacetonate) iridium (III)), bis [1- (9,9-dimethyl-9H-fluorene) 2-yl) -isoquinoline] (acetylacetonate) iridium (III),
• iridium (111), (Piq) 2 Ir (dpm) bis (phenylisoquinoline) (2,2,6,6-tetramethylheptane-3, 5-dionate) iridium (III) and iridium (III) bis (4-phenylthieno [3 , 2-c] pyridinato-N, C2 ') acetylacetonate and mixtures of the abovementioned substances.
• CnN a ligand in which the iridium atom is coordinated by a carbene carbon atom and a nitrogen atom.
• Phosphorescent metal complex and the Matixmaterial have an anisotropic molecular structure.
• Matrix materials may have an anisotropic orientation
• Phosphorescent metal complexes are additionally supported. According to the anisotropic phosphorescent
• Anisotropic molecular structure that here in particular no substantially symmetrically substituted linking points such as one in one, three and five
• a matrix material with anisotropic molecular structure is understood as meaning a material in which, starting from a central branching point, in particular a central atom or a central ring, there are no three, four or more substituents having the same or substantially the same structure (only substituents being taken into account that are not hydrogen).
• a similar structure means that the substituents are identical;
• a substantially similar structure further means that although the at least three substituents differ in the molecular weight attributed thereto, none of the substituents of the branching site has a molecular weight which is at least 50% lower than any of the other substituents (only Note substituents that are not hydrogen). Accordingly, molecules with anisotropic molecular structure are none
• Substituents or they have at branch points with three or more substituents (eg., Branching points such as tertiary amine nitrogen atoms or at least triply substituted benzene rings) very different
• the branching point defined above is in particular the branching point which corresponds to the molecular center of gravity on the
• the matrix material in step A) is selected from compounds of the type A-K-B.
• the structural element K stands for a structure Arl-X-Ar2, which is in particular like a chain.
• Ar 1 and Ar 2 stand for identical or different aromatic rings and X stands for a single bond, a further aromatic group or for a linkage (of Ar 1 and Ar 2) by means of a fused (or condensed) ring, ie a ring, with both Ar 1 and Ar 2 are condensed together.
• structural elements A and B are identical or different and each comprise at least one aromatic ring, in particular an aromatic ring, attached to the
• Structural element K is bound directly or indirectly (i.e. linked via further atoms or groups).
• the groups Ar 1, Ar 2 and X may be unsubstituted or arbitrarily substituted aromatic compounds, in particular
• the aromatic rings Ar 1, Ar 2 and X will therefore not have any substituents whose carbon atoms do not necessarily lie in the plane which is spanned by the aromatic ring, and usually also no substituents which are at least partially (spatially and / or temporally) are not in the plane defined by the aromatics plane. The same applies to
• Substituents of the structural element X if it is a non-aromatic bridge of the aromatic ring Arl and Ar2.
• any alkylene linkage (as it is present for example in a fluorene group described by the structure Arl-X-Ar2) may also be arbitrarily substituted.
• the substituents will often only be sterically less demanding substituents, such as methyl, ethyl or propyl groups, or cyclic or spiro-cyclic alkylene groups, or groups which have a steric need for space, that of the groups mentioned is equal to or less (for example, metoxy groups).
• substituents such as methyl, ethyl or propyl groups, or cyclic or spiro-cyclic alkylene groups, or groups which have a steric need for space, that of the groups mentioned is equal to or less (for example, metoxy groups).
• a phenyl group may also be bonded to such an alkylene (for example methylene) group.
• Arl-X-Ar2 is in particular like a chain
• Structural elements A and B are bonded to each other such that the groups A and X (or A and Ar2 in the case where X represents a bond or a ring fused to Arl and Ar2) are arranged in para position to each other. the same
• inventive method is suitable. It is essential here that the linking of the structural elements A, K and B
• Structural element K no spirocyclic group having more than five carbon atoms, in particular no such
• the groups Arl and Ar2 of the structural member K are each a nitrogen containing heterocycle ⁇ and can, for example, a biphenyl, a phenanthroline, a pyridine, a bipyridine and / or a pyrimidine derivative include.
• both the structural element A and the structural element B of the matrix material AKB can be an aromatic-substituted one
• Amine group include, in particular, an aromatic amino radical
• the matrix material in this case may comprise a benzidine derivative.
• such matrix materials have a rather planar central segment in the form of the benzidine group or the
• Structure elements A and B of the matrix material are formed so that a particularly anisotropic molecular structure
• the structural elements A and B can therefore comprise, for example, a substituted aromatic which carries a tertiary alkyl group (in particular in the para position). If the structural elements A and B each contain a nitrogen atom which is bonded directly to structural element K, then only one of the two terminal atoms can
• Substituents of the nitrogen atom or both terminal substituents carry such a substituted aromatic group. Instead of one with a tertiary alkyl group
• substituted aromatic group may also be a
• the matrix material can be hole-transporting and / or electron-transporting
• an electron-transporting matrix material is frequently chosen, because this is usually more favorable due to the location of the triplet levels of the matrix material and the emitter material.
• the matrix material can be selected from one or more of the following compounds or at least one of the abovementioned compounds
• Compounds include:
• PBD (2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole
• BCP (2,9-dimethyl-4,7-diphenyl-1,1 O-phenanthroline), BPhen (4,7-diphenyl-l, 1-O-phenanthroline)
• TAZ (3- (4-biphenylyl) -4-phenyl-5-tert-butylphenyl-1,2,2-triazole
• Bpy-OXD (1,3-bis [2- (2,2'-bipyrid-6-yl) -1,3,4-oxadiazol-5-yl] benzene
• PADN (2-phenyl-9
• hole-transporting materials are NPB ( ⁇ , ⁇ '-bis (naphth-1-yl) - ⁇ , ⁇ '-bis (phenyl) -benzidine, ⁇ -NPB ( ⁇ , ⁇ '-bis (naphth-2-yl) - ⁇ , ⁇ '-bis (phenyl) benzidine), TPD (N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl) benzidine), N, N'-bis (naphthenic acid) 1-yl) - ⁇ , ⁇ '-bis (phenyl) -2,2-dimethylbenzidine, DMFL-TPD ( ⁇ , ⁇ '-bis (3-methylphenyl) -N, N'-bis (phenyl) -9, 9 dimethylfluorene, DMFL-NPB ( ⁇ , ⁇ '-bis (naphth-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9,9-
• BMPyP 1,4-di (1,10-phenanthrolin-3-yl) benzene
• BBCP 2,5-di (pyridin-4-yl) pyrimidine
• DBPy 2,5-di (pyridin-4-yl) pyrimidine
• BBPyP 1, 4-bis (2- (pyridin-4-yl) pyrimidin-5-yl) benzene
• GBPy 2, 2 ', 6, 6' -tetraphenyl-4,4'-bipyridine
• PBAPA 2, 3, 5, 6-tetraphenyl-4,4'-bipyridine
• TPPyPy 1,4-bis (2,3,5,6-tetraphenylpyridin-4-yl ) benzene
• BDPyPyP 1,4-bis (2,6-tetrapyridinylpyridin-4-yl) benzene
• the present invention further relates to a
• the radiation-emitting organic-electronic device obtainable by the method described above.
• the device is characterized in particular by the fact that, compared to the prior art, increased quantum efficiencies can be observed, since the alignment of the emitter molecules in the matrix material causes the loss channel of the
• Energy extraction can be blocked by plasmons. According to a further disclosed embodiment are between the
• the layer thickness is in particular 50 to 200 nm, for example 80 to 120 nm.
• the tendency is for a distance of at least 50 nm to have the effect that the decoupling via plasmons is additionally reduced; is the layer thickness of between
• Figures 1 and 2 are each a schematic representation of a radiation-emitting device according to a
• FIGS. 3A and B each show a measurement of the radiation intensity as a function of the polarization of the laser light used for the excitation and of the emission angle.
• the same, similar and equally acting elements are provided in the figures with the same reference numerals.
• FIG. 1 shows the schematic structure of a
• the following layer structure is realized from bottom to top in FIG. 1: At the bottom is the substrate 1.
• the radiation-transmissive substrate is a glass substrate, for example, borofolate glass, or a
• Plastic (film) substrate e.g. made of PMMA
• anode layer 2 which consists for example of a transparent conductive oxide
• Transparent conductive oxides are transparent, conductive materials, usually metal oxides, such as zinc oxide, tin oxide, cadmium oxide, titanium oxide, indium oxide or indium tin oxide (ITO), in addition to binary metal oxygen compounds, such as
• ZnO, SnO 2 or In 2 O 3 also include ternary metal oxygen compounds such as Zn 2 SnO 4, Cd SnO 3, Zn SnO 3, Mgln 204, GalnO 3, Zn 2 In 2 O 5 or In 4 Sn 3 O 12, or mixtures of different transparent conductive oxides into the group of TCOs.
• the TCOs do not necessarily correspond to a stoichiometric composition and may also be p- or n-doped.
• a transparent anode layer 2 may be present, which consists of a thin metal layer (such as silver) or one
• Alloy (such as AgMg) containing such a metal or alloy.
• a hole transport layer 4 which consists of a material or contains this, which may for example be selected from tertiary amines, carbazole derivatives, polyaniline or
• Polyethylenedioxythiophene By way of example, mention may be made of NPB, TAPC or other of the above anisotropic hole transport forming materials. However, non-anisotropic materials are also suitable for the hole transport layer 4. On the
• Hole transport layer follows the active layer in the case of an OLED, for example, an organic emitter layer 6.
• This emitter layer comprises the anisotropic matrix material and the anisotropic phosphorescent emitter or consists thereof.
• a cathode 10 on the emitter layer is finally a cathode 10, in particular a metal cathode, but optionally also a cathode, which is also made of a transparent conductive oxide (resulting in a top / bottom emitter) arranged.
• the cathode may consist of silver, aluminum, cadmium, barium, indium, magnesium, calcium, lithium or gold, or may comprise one or more of these metals.
• the cathode can also be designed as a multilayer.
• the OLED When a voltage is applied between the anode and cathode, current flows through the component and photons are released in the organically active layer, which in the form of light via the transparent anode and the substrate or in the case of a top / bottom emitter via the transparent cathode Leave component.
• the OLED emits white light; in this case contains the emitter layer either several different colors (for example blue and yellow or blue, green and red) emitting
• the emitter layer may also be composed of a plurality of sub-layers, in each of which one of said colors is emitted, wherein
• Primary emission also be arranged a converter material which at least partially absorbs the primary radiation and emits a secondary radiation of different wavelength, so that results from a (not yet white) primary radiation by the combination of primary and secondary radiation, a white color impression.
• the component 1 is preferably for illumination
• the component in particular for general lighting, expediently designed to generate visible radiation.
• the component can be used, for example, for interior lighting, for exterior lighting or in a signal light.
• Figure 2 shows an OLED, which is designed as a top emitter; If the cathode 10 is transparent, then it is a top / bottom emitter.
• a cathode 10 is arranged (which is formed for example of a metal or - in particular if a transparent electrode is desired - from a TCO
• Electron in etations slaughter 9 arranged, on which there is an electron transport layer 8.
• On the Electron transport layer 8 is a
• Emitter layer 6 is arranged. This emitter layer can be designed as described for FIG.
• On the emitter layer is a
• Hole transport layer 5 for example, TPBi (2, 2 ', 2' '- (1, 3, 5-benz-triyl) tris (1-phenyl-l-H-benzimidazole)) or one of the above anisotropic
• Lochin etechnischstik 4 is anode, which is formed for example from a TCO.
• the organic layers can be vapor deposited
• the substrate to be coated with electrode or electrode and dielectric layer is introduced into a recipient, who the
• the emitter layer used a source with anisotropic matrix material and a source with the phosphorescent anisotropic emitter. Accordingly, the
• Emitter layer the other organic layers are applied by evaporation possible.
• the illustration of an encapsulation for the organic layers has been omitted for reasons of clarity. Likewise, for reasons of clarity, it has been dispensed with to represent an optionally contained radiation-decoupling layer.
• An encapsulation encapsulates the organic
• the encapsulation may e.g. be designed as a roof construction. Also on one
• Electron blocking layer a 10 nm thick emitter layer of 92% -NPD and 8 wt .-% to iridium (III) - bis (dibenzo [f, h] -quinoxaline) (acetylacetonate) deposited.
• iridium (III) - bis (dibenzo [f, h] -quinoxaline) (acetylacetonate) deposited To adjust thermodynamic conditions, the
• Electron transport layer deposited For the measurement of the emitter orientation, an OLED stack produced in this way was produced used without cathode; for the measurement of the efficiency, a 200 nm thick silver cathode was used.
• TM-polarized P-polarized light
• TE-polarized s-polarized light
• the cw laser has substantially linearly polarized light.
• the angle-dependent photoluminescence spectra are measured by means of a calibrated fiber optic spectrometer and a polarizer to distinguish between TE and TM polarized
• the measured intensities are normalized to the measured values at low angles, since the emission in this range exclusively from parallel
• FIG. 3A shows the detected relative intensity as a function of the emission angle for p-polarized light of the wavelength 610 nm.
• the simulated relative ones are shown
• Figure 3B shows the corresponding results when instead of P-polarized radiation s-polarized radiation of a
• Wavelength of 610 nm is measured. Again, there is a good match of the simulated graph 13 and the actual measured curve 14.
• Orientation 2/3 of the dipoles lie in the plane formed by the OLED layers and 1/3 is oriented orthogonally to calculate that (the fraction of arbitrary
• the proportion of the respective loss channels was determined. After that is the

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