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Definitions

• the present invention relates to an organic semiconductive material comprising at least one matrix material and at least one doping material, an organic component comprising such an organic semiconductive material, and a mixture comprising at least one matrix material and at least one doping material for producing a doped semiconductor layer.
• the doping material serves to change the electrical properties of the matrix material.
• organic semiconductors can be constructed from either compounds with good electron donating properties or from compounds having good electron acceptor properties.
• HT electron donating materials
• strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyne (F4TCNQ) have become known (US7074500). These generate by electron transfer processes in electron donor-like base materials (hole transport materials) so-called. Holes, the number and mobility of which changes the conductivity of the base material more or less significantly.
• Suitable matrix materials with hole transport properties are, for example, ⁇ , ⁇ '-perarylated benzidines (TPD) or ⁇ , ⁇ ', ⁇ "perarylated starburst compounds, such as the substance TDATA, or else certain metal phthalocyanines, in particular zinc phthalocyanine ZnPc.
• the compounds described so far have disadvantages in the production of doped semiconductive organic layers or of corresponding electronic components with such doped layers for a technical application, since the manufacturing processes in large-scale production plants or those on a pilot plant scale can not always be controlled with sufficient precision, resulting in high control and control effort within the processes to achieve a desired product quality, or to undesirable tolerances of the products. Furthermore, there are disadvantages in the use of previously known organic dopants with regard to the electronic component structures, such as light-emitting diodes (OLEDs), field-effect transistors (FET) or solar cells, since the mentioned production difficulties in handling the dopants to unwanted irregularities in the electronic components or
• CONFIRMATION COPY can cause unwanted aging effects of the electronic components.
• the dopants to be used have extremely high electron affinities (reduction potentials) and other properties suitable for the application, since, for example, the dopants also determine the conductivity or other electrical properties of the organic semiconducting layer under given conditions. Decisive for the doping effect are the energetic layers of the HOMO of the matrix material and the LUMO of the dopant.
• OLEDs Electronic devices with doped layers are i.a. OLEDs and solar cells.
• OLEDs are e.g. from US7355197 or from US2009051271.
• Solar cells are e.g. from US2007090371 and US2009235971 known.
• the p-doped HTM is doped with the dopants according to the invention.
• EML is the "emission layer" of an OLED, OAS stands for "optical absorption layer of a solar cell” (typically a D-A heterojunction).
• the layer sequences (i) - (iv) are final layer sequences.
• doped hole transport layers or materials for forming these transport layers are based either on the properties of the dopant or on the properties of the hole transport material.
• the other component is described in general reference to the prior art. In fact they are For components with a doped hole transport layer usually better results to achieve than for a device with the same structure without dopants in the hole transport layer. In this limited view, however, it is overlooked that in order to fully optimize the overall properties of the device as the next step, the targeted adaptation of hole transport material and dopant to each other has to be made.
• the most suitable hole transport material for a doped layer is not necessarily the one that functions best as undoped hole transport material. Rather, Dotand and Matrix form a system that must be considered in its entirety.
• a central parameter for a hole transport material in an undoped layer is the so-called charge carrier mobility for holes. This determines how much voltage drops across this layer when a certain current density flows through this layer. Ideally, the charge carrier mobility is so high that the voltage drop across the single layer is negligible compared to the voltage drop across the entire device. In this' case, this layer is no longer limiting the current flow, and the carrier mobility may be sufficient to be considered optimized.
• this level has not yet been reached.
• a significant voltage for driving the current flow through hole transport layers is needed.
• the thickness of this layer should not only be chosen to be minimal, but must have a certain minimum layer thickness (> 50 nm), for example for reasons of process technology or for reasons of component stability.
• the selection of a good hole transport material for this layer must first orients itself to a maximum charge carrier mobility in order to limit the negative consequences on the performance parameters of the device.
• Other parameters that describe the material such as glass transition temperature (Tg), processing properties, cost of producing the material, take a back seat.
• -NPD N'-bis-aphthalene-ly-N ⁇ '- bis-f-d-benzylbenzidine
• ⁇ -NPD is also used commercially to make OLED products, although the low glass transition temperature was recognized as a disadvantage of this solution, but must be accepted.
• the situation is different for a hole transport layer doped with 3-radial connections.
• the inventors have found that a minimal voltage drop across the doped hole transport layer can be achieved for a larger number of hole transport materials.
• the doping effect of the 3-radial compounds makes the layer conductive.
• the conductivities are for a large number of hole transporting materials above the threshold value of 10 "5 S / cm. Fall For this conductivity at a comparatively high current density of 100 mA / cm 2 over a comparatively large layer thickness of 100 nm only 0.1 V ab.
• the inventors have found hole transporting materials which have the best possible performance in a doped hole transporting layer, taking into account those materials that were not considered in the conventional approach.
• each Ri is independently selected from aryl and heteroaryl, wherein aryl and heteroaryl are at least partially, preferably completely, substituted with electron-deficient groups (acceptor groups).
• Aryl is preferably phenyl, biphenyl, ⁇ -naphthyl, ⁇ -naphthyl, phenantryl or anthracyl.
• Heteroaryl is preferably pyridyl, pyrimidyl, triazyl or quinoxalinyl.
• Acceptor groups are electron withdrawing groups, preferably selected from fluoro, chloro, bromo, CN, trifluoromethyl or nitro.
• suitable dopants are described for organic semiconductive materials, such as hole transport materials HT, which are commonly used in OLEDs or organic solar cells.
• the semiconductive materials are preferably intrinsically hole-conducting. It has been found that the following materials are suitable matrix materials and can be doped with the 3-radial compounds.
• Ri to Ri 8 are each independently selected from H and alkyl (C1-C9, branched and unbranched).
• Ri to Ri 3 H and alkyl (C1-C9, branched and unbranched)
• Ri to R 14 are H and alkyl (C1-C9, branched and unbranched)
• the materials of the formulas (3), (4), (5), and (6) are particularly preferred.
• the matrix material of the formula (3) is particularly preferred.
• HTM of formula 3 HTM of formula 4
• HTM of formula 5 HTM of formula 6, wherein HTM of formula 6 is the best material.
• matrix materials selected from the formula (3), wherein at least one H of the formula (3) is replaced by aromatics and / or heteroaromatics and / or C1-C20 alkyl.
• doped HTL hole transport layer
• the matrix material is a material of the HTM of the formula 4, HTM of the formula 5, HTM of the formula 6 and the dopant 2,2 ', 2 "- (cyclopropane-l, 2,3- triylidene) tris (2- (p-cyanotetrafluorophenyl) acetonitrile).
• a doped HTL wherein the matrix material is HTM of formula 3 and the dopant is 2,2 ', 2 "- (cyclopropane-l, 2,3-triylidene) tris (2- (p-cyanotetrafluorohexyl) acetonitrile) ,
• the present invention results in doped HTL that have lower absorption, better conductivity and / or better temperature stability. Overall, improved overall performance is achieved compared to ⁇ -NPD.
• Fig. La Schematic representation of a doped hole transport layer (12) on a
• Substrate (1 1) wherein the hole transport layer (12) of two electrodes (13) and (14) is electrically contacted.
• a planar structure is e.g. used as resistor, routing path, etc.
• Fig. Lb Schematic representation of a doped hole transport layer (17) between two electrodes (16) and (17) on a substrate (15). Other layers (18) may be present. Such a stacked layer construction is e.g. used in OLEDs, organic solar cells, etc.
• the dopants can be used for the production of organic light-emitting diodes (OLED), organic solar cells, organic diodes, in particular those with a high rectification ratio such as 10 3 -10 7, preferably 10 4 -10 7 or 10 5 -10 7 or organic field effect transistors become.
• the dopants according to the invention can be used to improve the conductivity of the doped layers and / or to improve the charge carrier injection of contacts into the doped layer.
• the component may have a pin structure or an inverted structure, without being limited thereto.
• the use of the dopants according to the invention is not limited to the above-mentioned advantageous embodiments.
• Preference is given to OLEDs which are ITO (indium tin oxide) free.
• OLEDs with at least one organic electrode are conductive layers containing the following materials as main components: PEDOT-PSS, polyaniline, carbon nanotubes, graphite.
• ITO Indium tin oxide
• FTO Braz J. Phys., V. 35 no.4 pp.1016-1019 (2005)
• light-emitting layer or system of several light-emitting layers e.g. CBP (carbazole derivatives) with emitter addition (e.g., phosphorescent triplet emitter iridium-tris-phenylpyridine Ir (ppy) 3) or Alq3 (tris quinolinato-aluminum) mixed with emitter molecules (e.g., fluorescent singlet emitter Qoumarin),
• CBP carbazo derivatives
• emitter addition e.g., phosphorescent triplet emitter iridium-tris-phenylpyridine Ir (ppy) 3
• Alq3 tris quinolinato-aluminum
• emitter molecules e.g., fluorescent singlet emitter Qoumarin
• Electron Transport Layer e.g. BPhen, Alq3 (Tris-quinolinato-aluminum), 10th electrode, usually a metal with low work function, electron-injecting
• layers may be omitted or a layer (or material) may take on several properties, e.g. For example, layers 3-5 and layers 7 and 8 can be combined. Other layers can be used. Stacked OLEDs are also provided and included.
• This design describes the non-inverted (anode on the substrate), substrate-emitting (bottom-emission) structure of an OLED.
• There are various concepts to describe emitting OLEDs away from the substrate see references in DE10215210.1), all in common that then the substrate side electrode (in the non-inverted case, the anode) is reflective (or transparent to a transparent OLED) and the Cover electrode (semi-) is transparent.
• the order of the layers is inverted (Cathode on substrate) one speaks of inverted OLEDs (see references in DE101 35 513.0).
• performance losses can be expected without special measures.
• a preferred design of the structure of an OLED according to the invention is the inverted structure (where the cathode is on the substrate) and wherein the light is emitted through the substrate. Furthermore, it is preferred that the OLED is top emitting.
• the typical structure of an organic solar cell can look like this:
• Anode preferably transparent, e.g. Indium Tin Oxide (ITO)
• hole-side intermediate layer preferably block layer, in order to prevent exciton diffusion from the absorption layer (optical active layer, also called emission layer) and to prevent charge carrier leakage from the emission layer,
• Optical active layer typically a strongly light-absorbing layer of a heterojunction (two or more layers or mixed layer) e.g. Mixed layer of C60 and ZnPc,
• Cathode e.g. Aluminum.
• layers can be omitted or a layer can take on several properties. Other layers can be used. Stacked (tandem) solar cells are provided and included. Variants such as transparent solar cells, inverted structure or m-i-p solar cells are also possible.
• a preferred configuration of the structure of a solar cell is the inverted structure (with the cathode on the substrate) and where the light is incident through the substrate.
• Another preferred configuration of the structure of a solar cell is the inverted structure (where the cathode is on the substrate) and where the light is incident through the anode.
• aryl cyanoacetic ester (f-j) was refluxed in 84 ml of acetic acid (50%) along with 4.15 ml of concentrated sulfuric acid for 16 h. After cooling, the entire amount was added to 120 ml of ice water and stirred for 30 min. The phases were separated and the aqueous phase extracted with 100 ml of chloroform. The combined organic phases were washed with 100 ml of water and then with 100 ml of saturated sodium bicarbonate solution. After drying with magnesium sulfate and removal of the solvent, after distillation in vacuo, colorless oils (k-o) were obtained.
• the aqueous solution was extracted by shaking three times with 500 ml of ethyl acetate each time and the combined organic phases were washed first with saturated brine, then with water, then with sodium bicarbonate solution and finally with water again. It was dried with magnesium sulfate and the solvent removed in vacuo. The remaining dark brown oil was used without further purification in the next synthesis.
• the material was dissolved in 1.4 1 of glacial acetic acid and treated dropwise with stirring with a previously prepared mixture of 360 ml of hydrobromic acid (48%) and 120 ml of nitric acid (65%). It was stirred for 1.5 h and then filtered. The red solid was washed with water, dried in vacuo and then purified by gradient sublimation (pt).
• the conductivity of a thin-film sample is measured by the 2-point method.
• a substrate contacts made of a conductive material, such as gold or indium-tin oxide.
• the thin film to be examined is applied over a large area to the substrate, so that the contacts are covered by the thin film.
• the current then flowing is measured. From the geometry of the contacts and the layer thickness of the sample results from the thus determined resistance, the conductivity of the thin-film material.
• the 2-point method is permissible if the resistance of the thin film is significantly greater than the resistance of the leads or the contact resistance. Experimentally, this is ensured by a sufficiently high contact distance, and thereby the linearity of the current-voltage characteristic can be checked.
• the temperature stability can be determined by the same method or the same structure by the (undoped or doped) layer heated gradually and after a rest period, the conductivity is measured. The maximum temperature that the layer can endure without losing the desired semiconductor property is then the temperature just before the conductivity breaks down.
• a doped layer may be heated on a substrate with two adjacent electrodes as described above in 1 ° C increments, with 10 seconds left after each step. Then the conductivity is measured. The conductivity changes with the temperature and abruptly breaks down at a certain temperature. The temperature stability therefore indicates the temperature up to which the conductivity does not abruptly break.
• the dopant is present in a doping concentration of ⁇ 1: 1 to the matrix molecule or the monomeric unit of a polymeric matrix molecule, preferably in a doping concentration of 1: 2 or smaller, more preferably from 1: 5 or less or 1: 10 or smaller ,
• the doping concentration may be limited in the range of 1: 5 to 1: 10,000.
• the doping of the respective matrix material with the p-dopants to be used according to the invention can be produced by one or a combination of the following processes: a) mixed evaporation in vacuo with a source of the matrix material and one for the dopant.
• a 50 nm thick layer of HTM of formula 3 was doped with compound (p).
• the doped layer was prepared by mixed evaporation of the HTM of formula 3 and the dopant (p) under high vacuum.
• the concentration of dopant in the matrix was 3 mol%.
• the evaporation temperature of the dopant was 372 ° C.
• the doped layer showed a high conductivity of 6T0 "4 S / cm.
• the temperature stability of the layer was 133 ° C.
• Example 1 Components: Example 1:
• a layer of HTM of formula 3 was doped with compound (p).
• the doped layer was deposited on a ITO coated glass substrate by coevaporation of the HTM of Formula 3 and the dopant (p) under high vacuum.
• the concentration of dopant in the matrix was 1.5; 3.0; 4.5 wt%.
• an a-NPD layer doped with 3 wt% of compound (p) was also deposited on the same substrate. Subsequently, without interruption of the vacuum, a layer of ⁇ -NPD, a fluorescent blue emitter layer, an undoped ETL and block layer was n: doped
• Electron transport layer and an aluminum cathode deposited were Electron transport layer and an aluminum cathode deposited. Subsequently, the thus processed components were encapsulated against water with a lidded glass - a corresponding getter was previously introduced.
• the operating voltage is improved when using HTM of formula 3 relative to ⁇ -NPD.
• This lower initial voltage then also leads to better efficiencies.
• the power efficiency improves from 10.18 for the reference to 10.72 lm / W using HTM of Formula 2, both of which, HTM of Formula 3 and ⁇ -NPD, have been doped with 3 wt% (p) , The improvement in efficiency is thus over 5%.
• Another important performance parameter of OLED devices is the lifetime defined as the time that the initial brightness has dropped to half at a given current density. As can be seen from the table, one does not have to accept any losses here when using HTM of formula 3 relative to ⁇ -NPD. On the contrary, in the above example with 3 wt% electrical doping, the lifetime at 30 mA / cm 2 improves from 476 to 556h, or more than 15%.
• a layer of HTM of formula 3 was doped with compound (p).
• the doped layer was deposited on a ITO coated glass substrate by coevaporation of the HTM of Formula 2 and the dopant (p) under high vacuum.
• the concentration of dopant in the matrix was 3.0 wt%.
• an a-NPD layer doped with 3 wt% of compound (p) was also deposited on the same substrate.
• either a layer of ⁇ -NPD or a layer of HTM of formula 3 was deposited without interruption of the vacuum.
• the device was completed by a fluorescent red emitter layer, an undoped ETL and block layer, a doped electron transport layer and an aluminum cathode.
• the thus processed components were encapsulated against water with a lidded glass - a corresponding animal was previously introduced. This results in the glass substrate emitting red OLEDs whose characteristics are summarized in the table below.
• the efficiency of the red OLED significantly improves when using HTM of formula 3 as doped and as undoped layer relative to a reference OLED, where both of these layers consist of the standard ⁇ -NPD material.
• the power efficiency improves e.g. from 7.8 to 8.4 lm / W, ie by about 8%.
• Another component example is intended to represent the superior temperature stability of the doped semiconductor layers.
• a 30 nm thick layer HTM of formula 4, HTM of formula 5 and HTM of formula 6 were processed on ITO Glass.
• a reference layer of 30 nm ⁇ -NPD All of these materials were electrically doped with (p) 3% by co-evaporation.
• a uniform, 50 nm thick layer of a highly stable hole transporting material TBRb (TertButylRubrene) was evaporated on all these layers.
• the hole-transporting devices were terminated with a common, 100 nm thick aluminum electrode.
• the characteristics can be roughly subdivided into desired forward currents for voltages greater than 1 V and parasitic leakage currents for voltages of less than 1 V.
• 1V in this case is the turn-on voltage of the device.
• the ⁇ -NPD component already after processing significantly higher leakage currents relative to the materials according to the invention, HTM of formula 3, HTM of formula 4, HTM of formula 5 and HTM of formula 6.
• the difference, for example at -5 V, is about 2 orders of magnitude.
• the problem of parasitic leakage increases even further for ⁇ -NPD after heating.
• the leakage currents at -5 V reach almost 10 mA / cm 2 .
• components which use hole transport layers in the context of the invention behave much more tolerant of increasing temperature, and are at -5 V lower than the reference value of ⁇ -NPD at about 0.0001 mA / cm 2 by more than five orders of magnitude.
• the example demonstrates that it is possible to realize significantly more temperature-stable organic components with hole transport materials in the sense of the invention than with the standard hole transport material a-NPD.
• HTM high vacuum
• the doped layers were deposited by co-evaporation with the dopant (p) in a high vacuum on an ITO coated glass substrate.
• concentration of dopant in the matrix was 3.0 wt% in each of the four cases.
• an ⁇ -NPD layer doped with 3 wt% of compound (p) was also deposited on the same substrate.
• a layer of a-NPD, a red, a yellow, a blue and a green-emitting layer, an undoped ETL and blocking layer, an n-doped electron transport layer and an aluminum cathode were deposited without interruption of the vacuum.
• the initial efficiency of the components when using a hole transport layer in the sense of the invention is somewhat better, in part slightly worse, relative to the standard hole transport material ⁇ -NPD.

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