EP2837046A1 - Organisch elektronische bauelemente mit organischen superdonoren mit mindestens zwei gekoppelten carben-gruppen und deren verwendung als n-dotierstoffe - Google Patents

Organisch elektronische bauelemente mit organischen superdonoren mit mindestens zwei gekoppelten carben-gruppen und deren verwendung als n-dotierstoffe

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Publication number
EP2837046A1
EP2837046A1 EP13717462.9A EP13717462A EP2837046A1 EP 2837046 A1 EP2837046 A1 EP 2837046A1 EP 13717462 A EP13717462 A EP 13717462A EP 2837046 A1 EP2837046 A1 EP 2837046A1
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EP
European Patent Office
Prior art keywords
organic
dopant
carbene
electron
groups
Prior art date
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EP13717462.9A
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German (de)
English (en)
French (fr)
Inventor
Günter Schmid
Andreas Kanitz
Sébastien PECQUEUR
Jan Hauke WEMKEN
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Siemens AG
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Siemens AG
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Publication of EP2837046A1 publication Critical patent/EP2837046A1/de
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/611—Charge transfer complexes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to a novel material for n-doping of electron transport layers, the use of these compounds for the construction of organic electronic Bauelemen- te, transistors, organic light-emitting diodes, light-emitting electrochemical cells, organic solar cells, photodiodes and electronic components enthal ⁇ tend these compounds.
  • Organic electrical components consist at least partially stabilized, organic materials or compounds, which may have in addition to the well known insulating properties and electrically conductive or semiconductive characteristics. The quality and functionality of organic electrical components such as organic solar cells, transistors, light-emitting components and photodiodes depends essentially on the design of the components used.
  • Organic electrical components typically have transport layers with p (hole) or n (electron) conductivity, the efficiency of the layers for many
  • Components is highly influenced by the achievable conductivity.
  • the electron mobility and the number of moving / free charge carriers thereby determine generally the transport-conductivity and thus also the injection and / or transport ⁇ properties of the layers.
  • the efficiency of organic solar cells increases when the least possible voltage drops across the transport layers with p or n conductivity.
  • the clock Kon ⁇ resistors which effectively measured mobility of the semiconductor is a function of the clock Kon ⁇ resistors. If these contact resistances are minimized, higher switching frequencies can generally be realized in the circuit. be siert.
  • Equally significant impact has the Ausgestal ⁇ processing of the transport layers in bi-polar transistor devices, as described for example in detail in DE102010041331.
  • the luminescence, efficiency and service life depend strongly on the exciton density of the light-emitting layer and is limited, inter alia, by this.
  • an improvement in the properties of electron transport layers can be achieved by doping the matrix material.
  • the doping is significantly more difficult than in the p-doping since doping substances whose HOMO (Highest Occupied Molecular Orbital) is higher than the LUMO (Lowest Unoccupied Molecular Orbital) of the electron transporter must be found. Only in this way an effective electric ⁇ nenschreibtrag can take place from the dopant to the electron transporter. In general, this is due to materials with extremely low work functions or ionization energies reached (alkali and alkaline earth metals, as well as the Lanthanoi- the).
  • tetrathiafulvalenes have been described as doping substances in combination with strong electron acceptors from the class of the tetracyanoquinodimethanes as the first charge transfer salts which have metallic conductivity (Ferraris, J. et al., J. Am. Chem. Soc. 1973 , 95, 948; Coleman, LB, et al., Solid State Municipal. 1973, 12, 1125.).
  • WO 2007 107306 A1 describes the use of heterocyclic radicals or diradicals whose dimers, oligomers,
  • EP 1837926 AI EP
  • 1837926 Bl, US 2007 0252140-A1, EP 1837927 Al, WO 2007 107306 are also heterocyclic radicals or diradicals, their dimers, oligomers, polymers, dispiro compounds and poly ⁇ cyclen and rials their use as organic semi-conductive Mate ⁇ and electronic and optoelectronic devices disclosed ,
  • US 2008 029 7035 A1 describes the use of donor carbene intermediates for improving electron injection and electron transport in organic electronic components such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs) and organic photovoltaic components, in particular organic solar cells .
  • donor carbene intermediates are disclosed for injection purposes in electron transport layers, it is characteristic of the classes of compounds presented that they have (several) amine substituents on the donor carbene body, which after the donation of an electron to the electron transport layer stabilize the dopant as a quinoidal system. This can be exemplified by the reaction mechanism of a connec ⁇ tion
  • the object of the present invention is to eliminate the disadvantages occurring in the prior art and to provide an organic electronic device with an organic electron donor compound or an electron donor compound, which is used for doping electron transport ⁇ layers and the effectiveness organic increased electrical components.
  • the electron donor compound consists of at least two carbene groups Qi and Q 2 (generally Q x ), which are coupled to each other via a bridge (B).
  • the bridge (B) consists of at least one double bond.
  • a single bond is not inventive as these Bin ⁇ dung dissociated in case of electronic excitation.
  • the bridge (B) but also quinoid ring systems with and without heteroatom included. Two quinoid ring systems are shown below by way of example, which may also be part of more complex inventory ⁇ , fused-systems.
  • the lone pair of electrons of the carbon is over the
  • the bis-carbene is made up of two individual carbene groups.
  • the bridge (B) in the product in this case consists of the double bond between the two carbene groups.
  • the substance class having a double bond in the bridge referred to as bis-carbene compound having the above Darge ⁇ presented structure, as this is purely formal composed of two carbenes. Since the bis-carbenes no Carbene properties, they are hereinafter referred to as "super-electron donors" (SED), as well as in modern literature, since they are capable of acting as reducing ⁇ onsmittel.As super-donor substances be - which have a quinoidal structure in their neutral form, and which become completely or partially aromatic by electron donation.
  • systems for the doping of electron transport layers consist of two quinoid units which are linked to one another via a double bond or to a bridge analogous thereto.
  • Such a system is in equilibrium with its diradical without the need to break the binding framework of the molecule as indicated in the prior art.
  • the biscarbene can donate an electron.
  • the result is a radical cation.
  • the driving force for the reac ⁇ tion is the re-flavoring of the radical cation. Since formally "only" electrons are transferred and no bonds broken, this process is reversible, meaning that the equilibrium between the donor, the radical cation, and the (radical) acceptor anion sets in.
  • the radical anions are the most unstable species in the system, they can In the organic component, the functionality can be set as follows:
  • the donor strength of the organic electron donor compound should be adapted so that only a few radicals are on the acceptor in the quiescent state of the device. This can extend the service life of the component.
  • Electron transport materials are weak electron acceptors.
  • a general example of an electron acceptor is, for example, BPhen (4,7-di (phenyl) -1,10-phenanthroline).
  • the electron acceptors take up, at least temporarily, an electron of the biscarbene.
  • the driving force for the release of the electron is the re-aromatization of the electron-donating cyclic organic
  • Electron donor connection It creates a radical cation. The reaction is reversible, since in the electron donor compound no binding scaffolds are cleaved. There is only a partial charge exchange.
  • a bis-carbene comprises 2 analogue 6-membered ring systems and another example verdeut ⁇ light electron transfer of an analog 5-membered ring system.
  • Both bis-carbene compounds are capable of reversibly releasing an electron to an organic electron transporter (in this case exemplified by BPhen).
  • the respective radical anion / cation pair are formed.
  • the present invention provides an organic electronic device comprising at least two electrodes and an organic electron transport layer comprising one or ⁇ ganischen n-dopants available, which is characterized in that the n-dopant at least two via a bridge (B) connected contains cyclic carbene groups (Q x ), which do not dissociate upon electronic excitation of the compound and aromatized at least one carbene base body and the carbene groups are not directly connected to each other via a Me ⁇ tall ligands.
  • organic electronic component and polymer electronic components are understood here as organic light emitting diodes, organic Solarzel ⁇ len, light-emitting electrochemical cells, photo diodes and organic field effect transistors.
  • the organic electron-donor compound is from constructed or may contain at least two verbun via a covalent bridge ⁇ dene carbene groups.
  • the combination of two carbene groups forms a so-called bis-carbene.
  • Carbene groups are understood to mean electrically neutral, unstable electron deficient compounds which have a divalent carbon atom with an electron septum at one point of their skeleton. Carbenes thus formally have a free electron pair on a carbon, which is not involved in a covalent bond.
  • the carbene groups may consist of cyclic hydrocarbons. More preferably, the carbenes may consist of cyclic hydrocarbons which are partially unsaturated and allow for resonance stabilization of the free carbene electron pair.
  • This Resonanzsta ⁇ bilmaschine can additionally also free, ie non bonding electron pairs of heteroatoms (eg oxygen, sulfur, selenium or tellurium, nitrogen, phosphorus or arsenic, etc.) take place, which can be incorporated within the cyclic skeleton of the carbene groups. Preference is given to the incorporation of nitrogen as a heteroatom.
  • the carbene groups can have a quinoid structure.
  • a quinone is a benzene derivative in which the substituents are replaced by double-bond oxygen, thus eliminating the aromaticity of the ring on two carbon atoms
  • the chemical compound, i. Coupling of the two carbene groups may preferably lead to an organic electron donor compound which is electrically neutral in its entirety and preferably has a quinoid structure. Since within this bis-carbene structure the carbene groups no longer possess any carbene properties, this type of compound is also referred to in modern literature as the "super-electron donor" (SED).
  • SED super-electron donor
  • the SEDs can have substituted or unsubstituted homocycles or hetero cycles at each bondable site of the main body.
  • the substituents may preferably be selected from substituted and unsubstituted heterocycles, such as, for example, furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothazole, pyrazole, pyridine, pyrazine, pyrimidine, 1,3,6-triazine, pyrylium, alpha- Pyrone, gamma-pyrone, benzofuran, benzothiophene, indole 2H-isoindole, benzothiazole, 2-benzothiophene, 1H-benzimidazole, ⁇ -benzotriazole, 1, 3-benzoxazole, 2-benzofuran, 7H-purine, quinoline, iso-quinoline , Quinazolines, quinoxalines, phthal
  • alkyl radicals may generally contain ether groups (ethoxy, methoxy, etc.), ester, amide, amines, carbonate groups, etc., or else halogens, in particular CN and F.
  • ether groups ethoxy, methoxy, etc.
  • ester ethoxy, methoxy, etc.
  • amide ethoxy, etc.
  • amines ethoxy, etc.
  • carbonate groups e.g., benzyl
  • F halogens
  • substituent R is not limited to saturated systems, but may also include substituted or unsubstituted aromatics such as phenyl, diphenyl, naphthyl, phenanthryl or benzyl, etc. All substituents R of the compound main body can be chosen independently of one another.
  • the SEDs can generally act as a reducing agent.
  • the compound In the case of electronic stimulation e.g. by light, thermal radiation or the application of a voltage or by self-activation, the compound is capable of donating an electron while retaining its binding skeleton to an acceptor. The compound can then form a resonance-stabilized cation. It can commonly form salts with electron acceptors.
  • the electron transport layers may include electron transport materials, electron acceptors, and organic electron donor compounds.
  • 2, 2 ', 2 "- (1,3,5-triethylene triyl) tris (1-phenyl-1H-benzimidazoles), 2- (4-electron) can be preferably selected as electron transporting materials for the absorption of electrons.
  • Electron acceptors for the purposes of the present invention 2,3,5, 6-tetrafluoro-7, 7,8, 8-tetracyano-quinodimethane, pyrazino [2, 3-f] [1, 10] phenanthroline-2, 3-dicarbonitrile and Dipyrazino [2,3-f: 2 ', 3'-h] quinoxaline-2, 3, 6, 7, 10, 11-hexacarbonitrile.
  • the organic electron donor compounds may be applied to a layer together with an electron acceptor (s).
  • the compounds can be processed both in the gas phase, as well as the liquid phase.
  • both the dopant and the matrix material are vaporized together, preferably from different sources in a high vacuum, and deposited as a layer.
  • the finished layer is obtained by evaporation of the solvent. It can be adjusted by the different mass ratios of organic electron donor compound to the electron acceptor any doping ratios.
  • the two carbenes are not directly connected or bridged via a metal ligand.
  • this does not exclude that one or both carbene groups may have a metal Li ⁇ ligands within their binding scaffold.
  • the organic electron donor compounds according to the invention may contain, by way of example but not limitation, ferrocenyl, cyclopentadienyl dicarbonyl iron or phthalocyanines and porphyrins.
  • the organic electronic component is characterized in that the carbene groups of the organic n-dopant are directly connected to one another by a double bond.
  • the binding skeleton of the organic electron donor compound is not cleaved. That is, the two carbenes are still connected by a single bond in the electronically excited state and the molecule does not dissociate.
  • compounds of the following type are considered to be particularly inventive:
  • the organic electronic component is characterized in that the bridge (B) of the n-dopant contains at least one quinoid ring system.
  • the quinoid ring systems can either be based purely on carbon or contain heteroatoms.
  • the bridging quinoid units may be part of complex fused systems.
  • the number of quinoid units in the bridge can be between 0 and 20 units. If there is no quinoid unit between the carbene groups, then the two carbenes are bound together directly by a double bond.
  • a further particular embodiment of the invention constitutes the organic electronic device characterized labeled in ⁇ characterized in that at least one of the carbene groups of the organic ⁇ rule n-type dopant includes a 5- or 6-ring, which min- has at least 1 heteroatom.
  • a cyclic carbene compound of the invention in the following diagram is shown which consists of a 5-membered ring and contain other compounds, which ei ⁇ NEN cyclic 5-ring.
  • the structure with the letter (A) designates a fused aromatic Sys tem ⁇ (compound 27 + 28 + 29).
  • the 5-ring of the organic n-dopant can be connected to the second carbene group by an additional bridge (dashed line Verbindun ⁇ gen 28 + 29).
  • the carbene group can be connected via two additional compounds of the ring system with the other carbene group (compound 29).
  • Y denotes either O, S or N-R, the derivatives N-R being particularly preferred according to the invention.
  • the substituents R mentioned in the above example can be selected to be equivalent to the substituents already listed of the bondable sites of the main body.
  • organic electronic device of the organic n-type dopant is characterized labeled in ⁇ characterized in that the carbene groups from the same 5-rings are sawn, which have at least 1 heteroatom in the skeleton. Excluded from this class, however, are the Tetrathialfulvalene and their derivatives.
  • the organic n-dopant is thereby in that at least one of the carbene groups contains a 6-membered ring. Examples of these special execution ⁇ forms are given in the following drawing:
  • the first two structural formulas show a cyclic carbene group derived from a heteroaromatic compound.
  • the heteroatom Y stands at not conjugated with a double bond position.
  • the Z - positions (Z i to Z 4 ) denote atoms, which by a
  • Double bond bound and as C-H, C-D, C-R (the definition is equivalent to the definition of R of the substituted 5-rings) or N can be executed.
  • positions Z ⁇ there is the possibility that neighboring Zs (Z ⁇ and Z ⁇ + i) may be assembled into higher-annealed systems (naphthalene, anthracene, etc., or their hetero analogues).
  • the dashed arcs indicate those positions where bridging to other carbene groups is possible.
  • the bridge is located on the non-aromatic atom or, secondly, on one of the Z-formed CRs or, thirdly, on a combination of the different Z-positions (i and i, ii and ii, i and ii .).
  • both carbene groups can be of identical construction and each contain at least one 5- or 6-membered ring.
  • the bis-carbene would then be mirror-symmetrical in this particular case.
  • the organic n-dopant is characterized in that at least one of the carbene groups contains a tetrazine iodide.
  • the Tetrazinodihetarene were synthesized in 1986 by Eichenberger and Balli (Eichenberger, T. and Balli H., Helv. Chim Acta 1986, 69, 1521-1530.).
  • This class of compounds is formally constituted by an s-tetrazine at the oxidation state of a 1,4-dihydro-1,2,3,5-tetrazine and fused heterocyclic ring systems such as e.g. Pyridine, quinoline and isoquinoline.
  • planar nitrogen atoms on the bridgehead of the tetrazine ring participate in the ⁇ system with two electrons, thus leading to an overcompensation of the acceptor character of the pyridine-type nitrogen atoms.
  • This substance class can also be classified as a "Weitz type" donor.
  • the organic n-type dopant may be ge ⁇ is characterized in that it contains or consists of a bis-pyran a bis-pyran.
  • the synthesis of bis-pyrans was elaborated by A. Kanitz, among others.
  • the disclosure content of patent application WO2007 / 028738 may be added here.
  • the organic electronic device of the organic n-type dopant is characterized in that it comprises a 2.2 ⁇ , 6.6 ⁇ - contains tetraphenyl-4, 4 ⁇ -dipyran or from a 2.2 ⁇ , 6 , 6 ⁇ - tetraphenyl-4, 4 ⁇ -dipyran.
  • a further preferred embodiment of the organic electronic component is characterized in that the carbene groups of the organic n-dopant are additionally connected to one another via at least one second bridge.
  • Some non-limiting examples of multiple bridged super donors are given above (for example, compounds 1, 3, 5, 6, 7, 9, 15).
  • principle additional bridging possibilities for 5- or 6-atom cyclic compounds are given above (for example compound fertilize 28, 29 or compounds 32, 33).
  • Organic electron transport also According to the invention ⁇ layers containing an organic n-dopant, characterized in that the n-dopant at least two via a bridge (B) connected, cyclic carbene groups (QX), which do not dissociate upon electronic excitation of the connection and at least one carbene base body is aromatized and the carbene groups are not connected directly to one another via a metal ligand.
  • the individual or combinations of the properties and configurations of the n-dopants of the electron transport layers according to the invention correspond to those which are described above in the context of the description of the n-dopants of the organic electronic components according to the invention.
  • an organic electron transport layer an n-dopant, characterized in that the n-dopant at least two via a bridge (B) connected, cyclic carbene groups (QX), which do not dissociate in electronic ⁇ shear excitation of the connection and at least one carbene-flavored base body case and the Car ⁇ ben-groups are not directly connected together via a metal ligand.
  • a bridge B
  • QX cyclic carbene groups
  • the organically electronic components according to the invention can be used for the production of polymer-electronic components.
  • the synthesis of the GBP is two-tiered.
  • Sed1 The synthesis of Sed1 occurs in two stages according to a modi fied ⁇ provision JA Murphy, J. Garnier, SR Park, F. Schoenebeck, S. Zhou, A.. Turner, Org. Lett. 2008, 10, 1227.
  • IC-1) Preparation of Organic Electrically Conductive Layers Containing GBP On an ITO (indium-tin-oxide) electrode, a 200 nm thick layer of the electron conductor BCP (2, 9-dimethyl-4, 7 -diphenyl-1,10-phenanthroline).
  • the counterelectrode used is a 150 nm thick aluminum layer.
  • the GBP produced under I.A. is doped in concentrations of 2%, 5%, 15% and 25% relative to the rate of evaporation of the BCP.
  • Prefabricated ITO glass substrates are treated for 10 minutes using an oxygen plasma and quickly transferred into egg ⁇ NEN evaporator, which is filled glove box within an argon will be ⁇ having a water content less than 2 ppm.
  • the thermal evaporation is carried out at a base pressure klei ⁇ ner than 2xl0 ⁇ 6 mbar, which evaporation step is maintained during the entire Bedamp-.
  • the electron conductor and the dopant are simultaneously heated to a temperature just below their evaporation point on ⁇ . Then, the dopant is further heated while ⁇ until a constant vaporization rate is achieved.
  • the same procedure is followed with the electron conductor and with constant evaporation rates on both sides, the slide of the evaporator is opened.
  • the rate of electron transport is estimated at 1 ⁇ / s and the set Dotandenrate is selected in dependence on the concentration tandemich Verdampfungsra ⁇ te of the electron transport material and the desired Do-.
  • both sources are cooled down to below 40 ° C after evaporation.
  • the counter electrode is by means of thermal vapor deposition ist ⁇ eliminated and consists of a stack of a 10 nm thick calcium and a 150 nm thick aluminum layer.
  • the deposition is started at a rate of 0.5A / s by opening the gate and then slowly increasing the deposition rate to 5A / s.
  • the electrodes thus produced are subjected to a physical characterization.
  • GBP doping concentrations in the range between 5 and 15%.
  • the horizontal areas of the characteristic curves do not represent a current limit of the component, but are due to the safety-related current limits for the component. In general, the smaller the voltage at which the component reaches the maximum current density, the better the Dotieref ⁇ fect.
  • the symmetrical behavior of the current-voltage characteristic shows for the undoped BCP layer and the layers with the different GBP doping concentrations that the electron injection is independent of the work function of the metal electrodes and works equally well for aluminum and ITO electrodes. This is a desirable property for good dopants.
  • the conductivities as a function of the different GBP doping concentrations are illustrated once again in FIG. The course found does not correspond to the results of the IV characteristics.
  • the conductivity is small for the conductivity substrate with undoped GCP layer and increases with higher GBP doping concentration.
  • the measured conductivities, even at the highest measured GBP doping concentrations, are not in the range that would be expected from a good dopant (1E-5 to 1E-3 S / m).
  • the absorption spectra (see FIG. 3) of the layers with different GBP doping concentrations show that the absorption increases strongly with increasing GBP doping concentrations in the visible range of 400-700 nm. This increase is particularly evident in the blue-green range of 400-550 nm, which means that the layer has a distinctly red effect on the human eye.
  • the increase in absorption with increasing GBP doping concentration may be due, on the one hand, to the formation of charge-transfer complexes and, on the other hand, to the reddish base color of the GBP.
  • the quartz glass sheets produced in II.C were examined by photoluminescence spectroscopy. The results are shown in FIG.
  • the comparison of PL-spectra of pure BCP layers with GBP-doped BCP layers shows that the emission maximum shifts from 396 nm to 383 nm.
  • a marked second peak is formed for the GPB-doped layers at 480-540 nm, which becomes more pronounced as the GBP doping concentration increases.
  • the shift of the emission maximum on the formation of charge-transfer complexes is Komple ⁇ Without being bound by theory returned, while the second peak is attributable to the GBP.
  • the high emission can affect organic photodetectors and solar cells in particular posi ⁇ tively.
  • the quartz glass sheets produced in II.C were examined by reflection spectroscopy.
  • the results of Reflection spectra are shown in FIG. Comparing the reflection spectra of pure BCP layers with GBP-doped BCP layers reveals a GBP concentration-dependent decrease in blue-green wavelength reflection (420-550nm), whereas red-reflectance is GBP concentration-independent. From a purely optical point of view, this is also evident in the layers, whose hue is becoming darker and redder with increasing GBP concentration for the human eye.
  • the measurement data are obtained on components manufactured according to IC-2.
  • Layer can be determined depending on the dopant concentration, a higher output current, both positive and negative voltage curve relative to the ITO electrode.
  • the good effectiveness of the dopant can be derived for both dopant concentrations also from the symmetrical course of the current density / voltage curve.
  • the layer with the 10% doping shows a slightly better course than the layer with the 5% dopant content due to the higher current densities achieved.
  • FIG. 9 shows the current / voltage characteristics of components with a pure Alq3-, an Alq3-doped with 5% SED1 and a Component having a Alq3- doped with 5% Sed1 and a zusharm ⁇ union 15 nm thick SEDL-layer which was to cathode and doped electron transport layer till ⁇ eliminated between the calcium.
  • the individual doped layers differ only insignificantly in their current / voltage curves.
  • FIG 10 shows the current / voltage characteristics of a 4mm 2 large component with a 200 nm thick ETM-036 layer (ETM 036 is an electron transporting material of Fa. Merck OLED Mate ⁇ rials GmbH respectively Merck KGaA) with and without Sed1 as Do ⁇ tanden.
  • ETM 036 is an electron transporting material of Fa. Merck OLED Mate ⁇ rials GmbH respectively Merck KGaA
  • Sed1 Do ⁇ tanden
  • FIG. 12 shows the current / voltage characteristics of a 4 mm 2 large component with a 200 nm thick TMM-004 layer (TMM-004 is a triplet host and an electron transport material from Merck OLED Materials GmbH or Merck KGaA) with and without SED1 as dopants.
  • TMM-004 is a triplet host and an electron transport material from Merck OLED Materials GmbH or Merck KGaA
  • SED1 as dopants.
  • a higher output current can be detected for the layer doped with 5% SED1, both in the case of a positive and a negative voltage curve relative to the ITO electrode.
  • FIG. 14 shows the absorption properties of a ⁇ ETM-03- and one with 5% Sed1 doped ETM-03 layer. Both layers show an absorption maximum around 354 nm, with a lower absolute absorption of the doped ETM-03 layer. The decrease in absorption correlates with the concentration of ETM-03, which suggests that the absorption at these wavelengths is mainly determined by the electron transport material.
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