WO2011131185A1 - Mélange pour la fabrication d'une couche semi-conductrice dopée - Google Patents

Mélange pour la fabrication d'une couche semi-conductrice dopée Download PDF

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WO2011131185A1
WO2011131185A1 PCT/DE2011/075083 DE2011075083W WO2011131185A1 WO 2011131185 A1 WO2011131185 A1 WO 2011131185A1 DE 2011075083 W DE2011075083 W DE 2011075083W WO 2011131185 A1 WO2011131185 A1 WO 2011131185A1
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formula
layer
acetonitrile
cyclopropane
tris
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PCT/DE2011/075083
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German (de)
English (en)
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Michael Felicetti
Volker Lischewski
Mirko Tschunarjew
Carsten Rothe
Sascha Dorok
Ansgar Werner
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Novaled Ag
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/30—Doping active layers, e.g. 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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 present invention relates to the use of 3-radial compounds as an organic dopant for doping an organic semiconducting matrix material for changing the electrical properties thereof. Also, the invention relates to organic semiconducting materials and electronic components in which the 3-radial compounds are used.
  • 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 ⁇ , ⁇ '-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 leads to a desired Product quality or unwanted tolerances of the products. Furthermore, there are disadvantages in the use of previously known organic dopant end with respect to the electronic component structures, such as light-emitting diodes (OLEDs), field effect transistor (FET) or solar cells themselves, since the mentioned production difficulties in handling the dopants to unwanted irregularities in the electronic components or unwanted aging effects of the electronic Can lead components.
  • OLEDs light-emitting diodes
  • FET field effect transistor
  • 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 semiconductive 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 known, for example, from US Pat. No. 7,355,197 or US 2009/051271.
  • Solar cells are known, for example, from US 2007/090371 and US 2009/235971.
  • a preferred alternative of the invention provides that the following layer sequences are present in the component: (i) anode / dopant / HTM; (ii) anode / dopant: HTM. Also preferred is: (iii) dopant / HTM / EML or dopant / HTM / OAS; (iv) p-doped HTM / EML or dopant: HTM / OAS.
  • the p-doped HTM is mixed with the invention Dot doped.
  • EML is the "emission layer" of an OLED, OAS stands for "optical absorption layer of a solar cell” (typically a DA hetero-junction).
  • 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.
  • doped hole transport layer generally better results are achieved than for a device having the same structure but without the dopant in the hole transport layer. Due to this limited approach, however, it is overlooked that in order to fully optimize the overall properties of the component, the targeted adaptation of hole transport material and dopant to one another must take place as the next step.
  • 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 charge carrier mobility can be considered to be sufficiently optimized. In practice, this level has not yet been reached. Especially for colorless (in the visible non-absorbing) hole transport materials 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 process-technical reasons 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.
  • Tg glass transition temperature
  • a-NPD with its very high charge carrier mobility is considered to be one of the best hole transport materials, despite its comparatively low glass transition temperature of only 96 ° C.
  • a-NPD is also used commercially for the production of 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 3 -radio-doped hole transport layer.
  • 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. In particular, for This value is not very significant for OLED devices with a typical operating voltage of at least 3 V.
  • each Rl is independently selected from aryl and heteroaryl, wherein aryl and heteroaryl are at least partially, preferably fully substituted with electron-deficient compound (acceptor groups).
  • Aryl is preferably phenyl, biphenyl, a-naphthyl, b-naphthyl, phenanthryl, anthracyl, heteroaryl is preferably pyridyl, pyrimidyl, triazyl, quinoxalinyl
  • Electron-withdrawing groups preferably selected from are fluorine, chlorine, bromine, CN, trifluoromethyl, 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.
  • X methyl or tert-butyl
  • Y is selected from: substituted or unsubstituted tetraphenylmethane, or substituted or unsubstituted phenantherene.
  • Y is selected from:
  • the broken bond indicates the binding site of the substituents.
  • HTM of Formula 2 HTM of Formula 3
  • HTM of Formula 4 HTM of Formula 5
  • HTM of Formula 5 where HTM of Formula 2 is the best material.
  • H of formula (2) is substituted by aromatics and / or heteroaromatic and / or C1-C20 alkyl.
  • doped HTL hole transport layer
  • the matrix material is a material of the HTM of formula 3, HTM of formula 4, HTM of formula 5 and the dopant 2,2 ', 2 "- (cyclopropane-1, 2,3-triylidene ) tris (2- (p-cyanotetrafluorophenyl) acetonitrile).
  • HTM matrix material
  • dopant is 2,2 ', 2 "- (cyclopropane-l, 2,3-triylidene) tris (2- (p-cyanotetrafluorophenyl) acetonitrile).
  • FIG. 1a Schematic representation of a doped hole transport layer (12) on a substrate (11), wherein the hole transport layer (12) is electrically contacted between two electrodes (13) and (14).
  • 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). Additional layers may be present. Such a stacked layer construction is e.g. used in OLEDs, organic solar cells, etc.
  • organic compounds according to the invention for producing doped organic semiconducting materials which may be arranged in particular in the form of layers or electrical conduction paths, a multiplicity of electronic components or devices containing them can be produced.
  • Rectification ratio as 10 -10 'preferably 10 -10 or 10 -10 or organic field effect transistors are used.
  • 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 that are ITO free. Also preferred are OLEDs with at least one organic electrode.
  • Preferred organic electrode (s) are conductive layers containing as main components the following materials: PEDOT-PSS, polyaniline, carbon nanotubes, graphite.
  • the typical structure of a standard OLED may be as follows: 1. Support, substrate, e.g. Glass
  • ITO Indium tin oxide
  • FTO FTO
  • light-emitting layer or system of several light-emitting layers e.g. Emitter admixed CBP (carbazole derivatives) (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),
  • Electron Transport Layer e.g. BPhen, Alq3 (tris-quinolinato-aluminum),
  • layers can be left out or a layer (or material) can 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.
  • 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-) transparent. If the order of the layers is inverted (cathode on substrate) one speaks of inverted OLEDs (see references in DE101 35 513.0). Again, without special measures to be expected performance losses.
  • 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 Top is 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 eg aluminum.
  • layers can be left out or a layer can take over several properties. Other layers can be used.
  • Stacked (tandem) solar cells are provided. Variants such as transparent solar cells, inverted structure or mip solar cells are also possible.
  • a preferred configuration of the structure of a solar cell is the inverted structure (where the cathode is on the substrate) and wherein the light is incident through the substrate.
  • aryl cyanoacetic ester (fj) 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 United 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 was obtained after distillation in vacuo colorless oils (ko).
  • 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 (p-t).
  • the conductivity of a thin-film sample is measured by the 2-point method.
  • contacts made of a conductive material are applied to a substrate, e.g. 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 withstand without losing the desired semiconductor property, then the temperature is 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 less, 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 methods: a) mixed evaporation in vacuo with a source for the matrix material and one for the dopant. b) doping of a matrix layer by a solution of p-dopants with subsequent evaporation of the solvent, in particular by thermal
  • Doped Semiconductor Layer - Example 1 A 50 nm thick layer of HTM of Formula 2 was doped with compound (p). The doped layer was prepared by mixed evaporation of the HTM of formula 2 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 6-10 "4 S / cm. The temperature stability of the layer was 133 ° C.
  • Example 1 Components: Example 1:
  • a layer of HTM of formula 2 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 1.5; 3.0; 4.5 wt%.
  • a layer of a-NPD, a fluorescent blue emitter layer, an undoped ETL and block layer, an n: doped electron transport layer and an aluminum cathode were deposited without interruption of the vacuum.
  • the thus processed components were encapsulated against water with a lidded glass - a corresponding getter was previously introduced.
  • HTL Voltage / Current Efficiency Power Quantum Effi Lifetime Lifetime Density Efficiency ciency / h / h g with (p) [at 10 (cd / A) / (lm / W) /% [at [at)
  • the operating voltage is improved when using HTM of formula 2 relative to a-NPD.
  • This lower initial voltage then 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 2 and a-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 when using HTM of formula 2 relative to a-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 2 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 a-NPD or a layer of HTM of formula 2 was deposited without interruption of the vacuum.
  • the device was completed by a fluorescent red emitter layer, an undoped ETL and block layer, an n: doped electron transport layer and an aluminum cathode.
  • the thus processed components were encapsulated against water with a lidded glass - a corresponding getter was previously introduced.
  • the efficiency of the red OLED improves markedly when using HTM of formula 2 as doped and as undoped layer relative to a reference OLED where both of these layers consist of the standard material a-NPD.
  • the power efficiency improves, for example, from 7.8 to 8.4 lm / W, ie by about 8%.
  • Example 3 Another component example is intended to represent the superior temperature stability of the doped semiconductor layers.
  • a 30 nm thick layer HTM of formula 3, HTM of formula 4 and HTM of formula 5 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 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. Subsequently, the thus processed components were encapsulated against water with a lidded glass - a corresponding getter was previously introduced.
  • 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 a-NPD device already after processing significantly higher leakage currents relative to the materials according to the invention, HTM of formula 2, HTM of formula 3, HTM of formula 4 and HTM of formula 5.
  • the difference, for example at -5 V, is about 2 orders of magnitude.
  • the problem of parasitic leakage increases further for a-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 by more than five Orders of magnitude lower than the reference value of a-NPD at about 0.0001 mA / cm 2 .
  • the example demonstrates that it is possible to realize significantly temperature-stable organic components with hole transport materials in the context of the invention than with the standard hole transport material a-NPD.
  • HTM 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 a-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 block layer, an n-doped electron transport layer and an aluminum cathode were deposited.
  • the thus processed components were encapsulated against water with a lidded glass - a corresponding getter was previously introduced.
  • the processed OLED emits warm white light with color coordinates of (0.39, 0.40).
  • the corresponding characteristics are summarized in the following table.
  • HTL doping voltage power efficiency Quantum efficiency lifetime with 3wt% (p) / V / (lm / W) /% at 85 ° C
  • 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 a-NPD.

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Abstract

L'invention concerne une couche semi-conductrice organique comprenant au moins un matériau de matrice et au moins un matériau de dopage, caractérisée en ce que le matériau de dopage est sélectionné parmi des composés de formule (1), R1 étant indépendamment sélectionné parmi les aryles et les hétéroaryles, les aryles et les hétéroaryles étant substitués par au moins un substituant pauvre en électrons, de préférence complètement substitués, et en ce que le matériau de matrice est sélectionné parmi des composés de formule (2) ou des composés de formule (2) dans lesquels au moins un H de la formule (2) est substitué par des cycles aromatiques et/ou hétéroaromatiques et/ou des alkyles en C1-C20. L'invention concerne en outre un mélange comprenant au moins un matériau de matrice et au moins un matériau de dopage pour la fabrication d'une couche semi-conductrice dopée.
PCT/DE2011/075083 2010-04-21 2011-04-20 Mélange pour la fabrication d'une couche semi-conductrice dopée WO2011131185A1 (fr)

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EP2684932A1 (fr) * 2012-07-09 2014-01-15 Novaled AG Matériau de matrice dopé avec une composé mesomeric radialène
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US20180114916A1 (en) * 2015-04-10 2018-04-26 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
EP3345984A1 (fr) 2013-12-06 2018-07-11 Merck Patent GmbH Raccordements et dispositifs électro-organiques
WO2018189134A1 (fr) 2017-04-13 2018-10-18 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
EP3291323A4 (fr) * 2015-04-27 2018-12-19 Hodogaya Chemical Co., Ltd. Élément électroluminescent organique
WO2019002198A1 (fr) 2017-06-26 2019-01-03 Merck Patent Gmbh Mélanges homogènes
WO2019007866A1 (fr) 2017-07-05 2019-01-10 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
WO2019007867A1 (fr) 2017-07-05 2019-01-10 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
WO2019096717A2 (fr) 2017-11-14 2019-05-23 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
WO2019229011A1 (fr) 2018-05-30 2019-12-05 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
US20200013958A1 (en) * 2017-03-28 2020-01-09 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
WO2020178230A1 (fr) 2019-03-04 2020-09-10 Merck Patent Gmbh Ligands pour matériaux nanométriques

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