EP4256632A1 - Système stratifié pour composant électronique organique - Google Patents

Système stratifié pour composant électronique organique

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Publication number
EP4256632A1
EP4256632A1 EP21827587.3A EP21827587A EP4256632A1 EP 4256632 A1 EP4256632 A1 EP 4256632A1 EP 21827587 A EP21827587 A EP 21827587A EP 4256632 A1 EP4256632 A1 EP 4256632A1
Authority
EP
European Patent Office
Prior art keywords
layer
groups
group
stabilizer additive
polyphenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21827587.3A
Other languages
German (de)
English (en)
Inventor
Karsten Walzer
Marieta Levichkova
Ivan Ramirez
Bernhard SIEGMUND
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Heliatek GmbH
Original Assignee
Heliatek GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Heliatek GmbH filed Critical Heliatek GmbH
Publication of EP4256632A1 publication Critical patent/EP4256632A1/fr
Pending legal-status Critical Current

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Classifications

    • 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
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • 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
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • 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 potential barriers
    • 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
    • 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
    • H10K30/50—Photovoltaic [PV] devices
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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 layer system for an organic electronic component, having a first electrode, a second electrode, and at least one photoactive layer and/or at least one fullerene layer, the at least one photoactive layer and/or the at least one fullerene layer between the first electrode and the second electrode is arranged, wherein the at least one photoactive layer has at least one stabilizer additive, an organic electronic component with such a layer system, and a use of such a layer system in an organic electronic component.
  • Known solar cells preferably have active layers made of amorphous silicon (a-Si) or GIGS (Cu(In,Ga)(S,Se) 2 ). Also known are solar cells with organic photoactive layers.
  • the organic photoactive layers can be made up of polymers or small molecules. While polymers are characterized by the fact that they cannot be vaporized and can therefore only be applied from solutions, small molecules can be vaporized.
  • Organic semiconductors based on small molecules or polymeric compounds are increasingly being used in many areas of the electronics industry.
  • Organic semiconductors are used, for example, in electronic components such as organic field effect transistors (OFETs), organic light-emitting diodes (OLEDs), organic photovoltaic elements (OPVs) and photodetectors.
  • OFETs organic field effect transistors
  • OLEDs organic light-emitting diodes
  • OCVs organic photovoltaic elements
  • photodetectors Is the organic electronic component an organic optoelectronic component, such as a solar cell or a photodetector, then the device is capable of converting light energy into electrical energy, the opposite conversion of electrical energy into light emission having a detrimental effect on efficiency.
  • OLEDs convert electrical power or Voltage signals or electrical energy into light emission.
  • Organic photovoltaic components in particular organic solar cells, usually consist of a series of thin layers between two electrodes, which are preferably vacuum-deposited or processed from a solution.
  • the electrical contact can be made by metal layers, transparent conductive oxides (TCOs) and/or transparent conductive polymers (PEDOT-PSS, PANI).
  • TCOs transparent conductive oxides
  • PEDOT-PSS transparent conductive polymers
  • the vacuum evaporation of the organic layers is advantageous in the production of tandem, triple or multiple solar cells.
  • tandem or multiple solar cells the individual cells are stacked, with each cell containing at least one absorber layer, arranged between two electrodes and usually connected in series, so that the cell producing the lowest current limits the entire system.
  • the photoactive compounds are typically employed in a mixed layer or two adjacent layers to form donor-acceptor heterojunctions within a cell in which at least one donor and/or one acceptor is the light absorbing component.
  • donor and/or one acceptor is the light absorbing component.
  • organic solar cells free charge carriers are not directly generated by the light. Instead, excitons are initially formed, i.e. externally electrically neutral excitation states, in particular bonded electron-hole pairs. These excitons are separated into charge carriers at the donor-acceptor boundary layer in transitions between two adjacent layers or within a photoactive mixed layer, which migrate and thus contribute to the electric current flow.
  • the efficiency ( PCE ) of organic solar cells decreases over time as a result of degradation processes caused by the effects of light , heat , oxygen and/or water on the organic electronic materials are caused .
  • Radical scavengers and/or antioxidants are widely used additives in polymers and other organic systems to protect them from degradation.
  • Xu et al. discloses vitamin C (ascorbic acid) in perovskite cells, with vitamin C being used to stabilize Pb/Sn-based perovskite solar cells, to stabilize methylammonium (MA) or f ormamidinium (FA) used ascorbic acid as an effective antioxidant additive to increase the efficiency and stability of Pb/Sn-based perovskite solar cells.
  • Ascorbic acid delays the oxidation of Sn and modulates the crystallization of perovskite through the formation of intermediate complexes.
  • US20150228925A1 discloses the use of vitamin C as an oxygen-absorbing compound in an OLED display, with vitamin C being used in a transport layer.
  • the invention is therefore based on the object of providing a layer system for an organic electronic component, an organic electronic component with such a layer system, and a use of such a layer system in an organic electronic component, the disadvantages mentioned above not occurring, and in particular one improved stability and/or an increased service life of such a layer system is provided. It is particular The object of the present invention is to slow down the degradation of a layer system by slowing down the degradation of the layer system by adding one or more additives, referred to here as stabilizer additives, into the electrically active organic layer system.
  • the object is achieved in particular by providing a layer system for an organic electronic component, having a first electrode, a second electrode, and at least one photoactive layer and/or at least one fullerene layer, the at least one photoactive layer and/or the at least one fullerene layer is arranged between the first electrode and the second electrode, the at least one photoactive layer and/or the at least one fullerene layer having at least one stabilizer additive, the at least one stabilizer additive being selected from the group consisting of : with at least one RI , R2 , and/or R3 a polyphenol having at least two OH groups, or with at least one RI , R2 , and/or R3 a polyphenol having at least two OH groups and at least one RI , R2 , and/or R3 is a sterically hindered phenol having at least one steric alkyl group, the steric alkyl group being branched at the alpha position, and R4 independently selected from the group consisting of H, OH
  • Proportion of the at least one stabilizer additive in the at least one photoactive layer and/or the at least one fullerene layer is 0.001% by weight to 20% by weight, preferably 0.001% by weight to 10% by weight, preferably 0.001% by weight % to 5% by weight, preferably 0.001% by weight to 2% by weight, preferably 0.01% by weight to 10% by weight, preferably 0.01% by weight to 5% by weight.
  • -% preferably 0.01% by weight to 2% by weight, preferably 0.1% by weight to 30% by weight, preferably 0.1% by weight to 20% by weight, preferably 0.1% by weight.
  • -% to 10% by weight preferably 0.1% by weight to 5% by weight, preferably 0.1% by weight to 3% by weight, preferably 0.1% by weight to 2% by weight %, preferably 0.1% to 1% by weight, preferably 1% to 10% by weight, or preferably 1% to 2% by weight.
  • the at least one stabilizer additive is mixed into the at least one photoactive layer and/or the at least one fullerene layer.
  • the at least one stabilizer additive is at least largely homogeneously distributed as a further component in the at least one photoactive layer and/or the at least one fullerene layer, in particular homogeneously in an absorber material or a mixed layer of a donor-acceptor System.
  • the at least one stabilizer additive is at least largely homogeneously distributed in the at least one photoactive layer.
  • the layer system according to the invention has advantages compared to the prior art. Admixture of specific additives, in particular stabilizer additives, advantageously leads to an increase in the stability of a layer system, and thus also to an increase in an organic electronic component having this layer system, in particular an organic photovoltaic element.
  • the efficiency of the photovoltaic element is not significantly reduced in the process.
  • the efficiency of the photovoltaic element with such a layer system with at least one stabilizer additive is reduced to a lesser extent over time compared to a layer system without at least one stabilizer additive.
  • the addition of at least one stabilizer additive in particular increases the stability of the layer system with respect to moisture, oxygen and/or UV light.
  • the at least one stabilizer additive advantageously stabilizes absorbers in a photoactive layer.
  • the at least one stabilizer additive stabilizes a fullerene layer (Ceo) •
  • the stabilizer additives can be used at temperatures of up to 150° C., which corresponds to the use and process range of organic solar cells.
  • a steric alkyl group is understood to mean, in particular, an alkyl group with a branch in the alpha position of the alkyl group.
  • the steric alkyl group is an alkyl group with a branch in the alpha position, preferably an isopropyl group, an isobutyl group or a tert-butyl group.
  • At least one photoactive layer in particular an absorber layer, has at least one stabilizer additive.
  • at least one absorber layer and at least one HTL layer (hole conducting layer) and/or at least one ETL layer (electron conducting layer) has the at least one stabilizer additive.
  • photoactive means in particular a conversion of light energy into electrical energy.
  • absorber materials in photoactive layers have a large absorption coefficient, at least for a specific wavelength range.
  • Photoactive is preferably understood to mean that absorber materials, in particular at least one donor and/or at least one acceptor, change their charge state and/or their polarization state when exposed to light.
  • a photoactive layer is understood in particular a layer of an electronic component that contributes to Absorption of radiation and/or emission of radiation provides, in particular the photoactive layer absorbs radiation.
  • homogeneous is understood to mean in particular an at least largely equal distribution of the at least one stabilizer additive over the entire extent of the at least one photoactive layer and/or the at least one fullerene layer.
  • the at least one photoactive layer has an absorber material.
  • the at least one photoactive layer has a donor-acceptor system as absorber material.
  • a stabilizer additive is understood to mean, in particular, an antioxidant, a free-radical scavenger and/or a UV stabilizer.
  • the layer system has at least one photoactive layer with small molecules as the absorber material and the at least one stabilizer additive.
  • the layer system has at least one photoactive layer with small molecules as at least one donor, small molecules as at least one acceptor and the at least one stabilizer additive, the at least one donor and the at least one acceptor being a donor-acceptor system form .
  • small molecules are understood as meaning non-polymeric organic molecules with monodisperse molar masses between 100 and 2000 g/mol, which are present in the solid phase under standard pressure (air pressure of the atmosphere surrounding us) and at room temperature.
  • the small molecules are photoactive.
  • the at least one stabilizer additive has a molar mass between 100 and 1000 g/mol to .
  • the at least one stabilizer additive is introduced at the same time as a further component in addition to an absorber material or a donor-acceptor system during vacuum processing by co-evaporation.
  • the at least one stabilizer additive can be vaporized in vacuo, preferably processed in vacuo, with the at least one stabilizer additive not decomposing or at least largely not decomposing.
  • the at least one stabilizer additive is not polymerized in the at least one photoactive layer, preferably molecules of the stabilizer additive are not polymerized with one another in the at least one photoactive layer and/or molecules of the stabilizer additive are in the at least one photoactive layer is not polymerized with an absorber material.
  • the layer system according to the invention with at least one stabilizer additive has advantages compared to the prior art.
  • the stability and/or the service life of a layer system with at least one photoactive layer and/or at least one fullerene layer is advantageously increased with the at least one stabilizer additive.
  • Improved stability and/or an increased service life of organic electronic components, in particular of organic solar cells, is advantageously obtained with such a layer system.
  • the at least one stabilizer additive exhibits no or at least largely no absorption of light in the visible range of the electromagnetic spectrum, as a result of which no or at least largely no parasitic absorption takes place.
  • the stabilizer additives can be handled in a vacuum and can be sublimed at least largely non-destructively.
  • the stabilizer additives advantageously improve the service life of organic solar cells.
  • the at least one stabilizer additive can advantageously be a photoactive one Mix layer of a layer system without their electrical and optical and / or optoelectrical function is impaired.
  • the at least one photoactive layer and/or the at least one fullerene layer has a mixture of at least two, preferably at least three, preferably at least four, or preferably a large number of stabilizer additives.
  • At least one polyphenol of the groups RI, R2, R3 and/or R5 has at least one steric alkyl group, and/or at least one sterically hindered phenol of the groups RI, R2 and/or R3 has at least two steric alkyl groups and/or the stabilizer additive A15 to A18 R5 has an aromatic homocyclic or heterocyclic 5-ring or 6-ring with at least one OH group, preferably at least two OH groups, with one OH group in the beta position the carbonyl group is arranged from A15 to A18 R5, the stabilizer additive A15 to A18 R5 preferably contains a phenol, particularly preferably a polyphenol.
  • At least two RI, R2, and/or R3 of the stabilizer additive A1 to A14 are polyphenols, and/or at least two RI, R2, and/or R3 of the stabilizer additive A1 to A14 are steric Hindered phenols are, preferably at least three, and/or at least one OH group of a polyphenol of the groups RI, R2, R3 and/or R5 in the beta position or gamma position to a carbonyl group, and/or at least one polyphenol or a sterically hindered phenol of the groups RI, R2 and/or R3 of the stabilizer additive is bridged with another polyphenol or sterically hindered phenol by an alkyl group.
  • the at least one stabilizer additive is selected from the group consisting of: with at least two RI, R2 and/or R3 a polyphenol with at least two OH groups, or at least one polyphenol with at least two OH groups and at least one sterically hindered phenol with at least one, preferably at least two steric alkyl groups, and with R4 independently of one another selected from H and an alkyl group; (A4) with at least two RI, R2 and/or R3, a polyphenol with at least two OH groups, or at least two sterically hindered phenols with at least one steric alkyl group, preferably each with at least two steric alkyl groups, or at least one polyphenol with at least two OH groups and at least one sterically hindered phenol having at least one, preferably at least two, steric alkyl groups, and with R4 independently selected from H and an alkyl group; (All) with at least two RI, R2 and/or R3 a polyphenol with at
  • alkyl groups (A14) with at least one RI, R2 and/or R3, a polyphenol with at least two OH groups and at least one RI, R2 and/or R3 with a substituted or unsubstituted phenyl group, preferably with at least one phenyl group with at least an alkyl group, preferably with at least two alkyl groups, wherein preferably at least one alkyl group is a steric alkyl group, preferably with a RI, R2 and / or R3 a polyphenol with at least two OH groups and two RI, R2 and / or R3 a substituted or not -substituted phenyl group; with R5 selected from the group consisting of alkyl, O-alkyl, and a substituted or unsubstituted aromatic homocyclic or heterocyclic 5-ring or 6-ring having at least one OH group, preferably having an OH group in the beta position to the carbonyl group ; and vitamin C .
  • At least one RI, R2 or R3 in A12, A13 and/or A14 is a polyphenol having at least two OH groups and at least one RI, R2 or R3 is one substituted or unsubstituted phenyl group, preferably a phenyl group with at least one alkyl group, preferably with at least two alkyl groups.
  • at least one RI, R2 or R3 in A12, A13 and/or A14 is a polyphenol having at least two OH groups and two RI, R2 or R3 are a substituted or unsubstituted phenyl group.
  • the sterically hindered phenol has at least two steric alkyl groups, the sterically hindered phenol preferably being selected from the group consisting of CH2-DTB), where * represents the link to one of the structures A1 to A14.
  • the at least one stabilizer additive is selected from the group consisting of:
  • the at least one photoactive layer is an absorber layer, with the at least one photoactive layer preferably being formed as a mixed layer or of two adjacent layers with at least one donor and at least one acceptor, and the at least one donor and the at least one acceptor form a donor-acceptor system.
  • the at least one donor is an ADA oligomer and/or a BODIPY
  • the at least one acceptor is an ADA oligomer and/or a fullerene
  • the at least one stabilizer additive has an energy level at which the amount of the LUMO is less than the amount of the LUMO of the acceptor, preferably at least 0.1 eV less than the amount of the LUMO of the acceptor, preferably at least 0.2 eV smaller, or preferably at least 0.3 eV smaller, and the absolute value of the HOMO is greater than the absolute value of the HOMO of the donor, preferably at least 0.1 eV greater than the absolute value of the HOMO of the donor, preferably at least 0.2 eV greater , or preferably at least 0.3 eV greater .
  • a BODIPY compound is understood to mean in particular a compound of the general formula C9H7BN2F2, ie a compound with a boron difluoride group with a dipyrromethene group, in particular a compound 4,4-Difluoro-4-bora-3a,4a-diaza -s- Indacene .
  • An ADA oligomer is in particular a conjugated acceptor-donor-acceptor oligomer (AD-A'-oligomer) with an acceptor unit (A) and a further acceptor unit (A'), each attached to a donor unit (D) bound are understood.
  • At least one stabilizer additive is contained exclusively in the at least one photoactive layer.
  • the layer system has at least one transport layer, preferably at least two transport layers, which is arranged between the first electrode and the second electrode, the at least one transport layer being a hole conduction layer and/or an electron conduction layer, and where the at least one photoactive layer and at least one transport layer have at least one stabilizer additive.
  • the donor-acceptor system and/or the at least one stabilizer additive of at least one photoactive layer is processed in vacuo, ie applied to a layer of the layer system in vacuo.
  • the HOMO of the additive is at least 0.1 eV lower than the minimum of the HOMO of the donor relative to vacuum energy.
  • the LUMO of the additive is at least 0.1 eV higher than the minimum of the LUMO of the acceptor relative to vacuum energy.
  • the object of the present invention is also achieved by providing an organic electronic component with a layer system with at least one stabilizer additive according to the invention, in particular according to one of the exemplary embodiments described above, the at least one stabilizer additive preferably being present homogeneously in the photoactive layer and/or or the fullerene layer of the layer system is distributed.
  • the advantages that have already been explained in connection with the layer system result in particular for the organic electronic component.
  • the organic electronic component is an organic photovoltaic element, an OFET, or an organic photodetector.
  • the layer system has further layers, such as charge carrier transport layers, also called transport layers, between the electrodes, which make no or only a small contribution to absorption compared to a photoactive layer.
  • At least one charge transport layer is arranged between the first electrode and the at least one photoactive layer and/or the second electrode and the at least one photoactive layer. In a preferred embodiment of the invention, the at least one photoactive layer is adjacent to at least one charge transport layer.
  • the layer system has at least two, preferably at least three, or preferably at least four photoactive layers. This is particularly advantageous since the incident light passes through a number of photoactive layers within the layer system.
  • the layer system is designed as a tandem cell, triple cell or multiple cell.
  • the object of the present invention is also achieved by providing a use of a layer system according to the invention with at least one stabilizer additive in an organic electronic component, preferably an organic photovoltaic element, an OFET, or an organic photodetector, in particular according to one of those described above Examples .
  • a layer system according to the invention with at least one stabilizer additive in an organic electronic component, preferably an organic photovoltaic element, an OFET, or an organic photodetector, in particular according to one of those described above Examples .
  • the use of the layer system with at least one stabilizer additive in an organic electronic component results in particular in the advantages that have already been explained in connection with the layer system and the organic electronic component.
  • Fig. 1 shows a schematic representation of a layer system of an organic electronic component in one exemplary embodiment
  • Fig. 2 in one embodiment, the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system with a donor-acceptor system made of absorber: Ceo without stabilizer additive, and each with the stabilizer additives EA59, EA 61 and EA62 in a photoactive layer of the layer system;
  • the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system with a donor-acceptor system made of absorber: Ceo without stabilizer additive, and with the stabilizer additive EA50 in a photoactive layer of the shift system ;
  • the short-circuit current density, the fill factor, the no-load voltage and the efficiency of organic electronic components with a layer system with a donor-acceptor system made of absorber! Ceo without stabilizer additive and with the stabilizer additive EA55 in a photoactive layer of a layer system;
  • the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system with a donor-acceptor system made of absorber: Ceo without stabilizer additive, with the stabilizer additive EA55 in a photoactive layer, and with the stabilizer additive EA55 in a photoactive
  • the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system with a donor-acceptor system of Absorber3 Ceo without stabilizer additive, with the stabilizer additive EA55 in a photoactive layer, and with the stabilizer additive EA55 in a fullerene layer of a layer system;
  • Fig. 9 in one embodiment, the conductivity of a transport layer with different proportions of a stabilizer additive.
  • FIG. 1 shows a schematic representation of a layer system 1 of an electronic component.
  • the layer system for an organic electronic component has a first electrode, a second electrode, and at least one photoactive layer and/or at least one fullerene layer, with the at least one photoactive layer and/or the at least one fullerene layer between the first electrode and the second electrode is arranged.
  • the at least one photoactive layer and/or the at least one fullerene layer has at least one stabilizer additive, the at least one stabilizer additive being selected from the group consisting of: with at least one RI , R2 , and/or R3 a polyphenol having at least two OH groups, or with at least one RI , R2 , and/or R3 a polyphenol having at least two OH groups and at least one RI , R2 , and/or R3 is a sterically hindered phenol having at least one steric alkyl group, the steric alkyl group being branched at the alpha position, and R4 independently selected from the group consisting of H, OH, alkyl, and alkoxy; with at least one RI , R2 and/or R3 a polyphenol having at least two OH groups, and/or at least one RI , R2 and/or R3 a sterically hindered phenol having at least one steric alkyl group, the steric
  • At least one polyphenol of groups RI, R2, R3 and/or R5 has at least one steric alkyl group and/or at least one sterically hindered phenol of groups RI, R2 and/or R3 has at least two steric alkyl groups.
  • the stabilizer additive A15 to A18 R5 has an aromatic homocyclic or heterocyclic 5-membered ring or 6-membered ring with at least one OH group, preferably at least two OH groups, with one OH group in the beta position of the carbonyl group is arranged from A15 to A18 R5, the stabilizer additive A15 to A18 R5 preferably contains a phenol, particularly preferably a polyphenol.
  • the layer system 1 for an organic electronic component has a substrate 2, a first electrode 3, a second electrode 7, at least one photoactive layer 5, and alternatively a supplementary fullerene layer 6, the at least one photoactive layer 5 and the at least one fullerene layer 6 between the first electrode 3 and the second Electrode 7 are arranged.
  • the at least one photoactive layer 5 has at least one stabilizer additive.
  • the at least one stabilizer additive is at least largely homogeneously distributed in the at least one photoactive layer 5 .
  • the fullerene layer 6 alternatively or additionally has at least one stabilizer additive.
  • the at least one stabilizer additive is at least largely homogeneously distributed in the at least one fullerene layer 6 .
  • At least two RI, R2, and/or R3 of the stabilizer additive A1 to A14 are polyphenols, and/or at least two RI, R2, and/or R3 of the stabilizer additive A1 to A14 are sterically hindered phenols , preferably at least three .
  • At least one OH group of a polyphenol of the groups R1, R2, R3 and/or R5 is in the beta position or gamma position to a carbonyl group.
  • At least one polyphenol or a sterically hindered phenol from the groups R1, R2 and/or R3 of the stabilizer additive is bridged with another polyphenol or sterically hindered phenol by an alkyl group.
  • the at least one stabilizer additive is selected from the group consisting of: with at least two RI, R2 and/or R3 with a polyphenol having at least two OH groups, or with at least one polyphenol at least two OH groups and at least one sterically hindered phenol having at least one, preferably at least two, steric alkyl groups, and with R4 independently selected from H and an alkyl group; with at least two RI, R2 and/or R3, a polyphenol having at least two OH groups, or at least two sterically hindered phenols having at least one steric alkyl group, preferably each having at least two steric alkyl groups, or at least one polyphenol having at least two OH groups and at least one sterically hindered phenol having at least one, preferably at least two, steric alkyl groups, and with R4 independently selected from H and an alkyl group; (All) with at least two RI, R2 and/or R3, a polyphenol having at least two OH
  • alkyl groups with at least one RI, R2 and/or R3, a polyphenol with at least two OH groups and at least one RI, R2 and/or R3 with a substituted or unsubstituted phenyl group, preferably with at least one phenyl group with at least one alkyl group, preferably with at least two alkyl groups, with preferably at least one alkyl group being a steric alkyl group, preferably with one RI, R2 and/or R3 of a polyphenol having at least two OH groups and two RI, R2 and/or R3 of a substituted or unsubstituted phenyl -Group ; with R5 selected from the group consisting of alkyl, O-alkyl, and a substituted or unsubstituted aromatic homocyclic or heterocyclic 5-ring or 6-ring having at least one OH group, preferably having an OH group in the beta position to the carbonyl group ; and
  • the sterically hindered phenol has at least two steric alkyl groups, the sterically hindered phenol preferably being selected from the group consisting of tert-butylphenol (DTB) , and tert-butyl-4-methyl-phenol (CH2-DTB), where * represents the link to one of the structures A1 to A14.
  • DTB tert-butylphenol
  • CH2-DTB tert-butyl-4-methyl-phenol
  • the at least one stabilizer additive is selected from the group consisting of: , on the n.
  • the at least one photoactive layer is an absorber layer, with the at least one photoactive layer preferably being formed as a mixed layer or of two adjacent layers with at least one donor and at least one acceptor, and the at least one donor and the at least one acceptor form a donor-acceptor system.
  • the at least one donor is an ADA oligomer and/or a BODIPY
  • the at least one acceptor is an ADA oligomer and/or a fullerene
  • the at least one stabilizer additive has an energy level at which the magnitude of the LUMO is smaller than the magnitude of the LUMO of the acceptor, preferably at least 0.3 eV smaller than the magnitude of the LUMO of the acceptor, and the magnitude of the HOMO is greater than the magnitude of the HOMO of the donor, preferably at least 0.3 eV greater than the magnitude of the HOMO of the donor.
  • the at least one stabilizer additive is exclusively in the at least one contain photoactive layer.
  • the layer system has at least one transport layer, preferably at least two transport layers, which is arranged between the first electrode and the second electrode, the at least one transport layer being a hole conduction layer and/or an electron conduction layer.
  • the layer system has at least one transport layer, preferably at least two transport layers, which is arranged between the first electrode and the second electrode, the at least one transport layer being a hole conduction layer and/or an electron conduction layer, and the at least one Photoactive layer and at least one transport layer have at least one stabilizer additive.
  • the organic electronic component with a layer system according to the invention has at least one stabilizer additive, the at least one stabilizer additive preferably being distributed homogeneously in the photoactive layer and/or the fullerene layer of the layer system.
  • the organic electronic component is preferably an organic photovoltaic element, an OFET, or an organic photodetector.
  • the layer system according to the invention is used with at least one stabilizer additive in an organic electronic component, preferably an organic photovoltaic element, an OFET, or an organic photodetector.
  • an organic electronic component preferably an organic photovoltaic element, an OFET, or an organic photodetector.
  • the stabilizer additives according to the invention can therefore be used in vacuum-processed organic photovoltaic elements.
  • the layer system 1 with at least one stabilizer additive is in particular for use in an organic electronic component, preferably in an organic photovoltaic element, an OFET, or an organic photodetector.
  • the organic electronic component with the layer system 1 according to the invention with at least one stabilizer additive is in particular an organic photovoltaic element, in particular a organic solar cell, an OFET, or an organic photodetector.
  • the electronic component with the layer system 1 is an organic solar cell.
  • the layer system 1 is arranged on a transparent substrate 2 which is preferably designed to be flexible, in particular as a film.
  • a first electrode 3 is arranged on the substrate 2 and is made, for example, of metal, a conductive oxide, in particular ITO, ZnO:Al or another transparent, conductive oxide or polymer, such as PEDOT:PSS or PANI.
  • a charge carrier transport layer 4 is arranged on the first electrode 3 and is in the form of an electron or hole transport layer, for example.
  • the photoactive layer 5, which comprises at least one donor and one acceptor material, which together form a donor-acceptor system, is arranged on the charge carrier transport layer 4.
  • the photoactive layer 5 can also consist of more than one layer, in particular of a donor and acceptor layer, so that a planar, photoactive donor-acceptor transition is formed.
  • the photoactive layer includes a stabilizer additive in a proportion of 0.1 wt. -% up to 10 wt. -% .
  • a further charge carrier transport layer 6 is arranged on the photoactive layer 5 .
  • This charge carrier transport layer 6 is also designed as an electron or hole transport layer.
  • the second electrode 7 is arranged on the charge carrier transport layer 6 and is formed, for example, from a metal such as Al, but also from an optically transparent one electrical conductor layer can exist.
  • Vacuum co-evaporation with OPV materials selected from three functional classes was used to produce the layer system : co-evaporation with 1 ) absorber materials, 2 ) hole conductors, and 3 ) electron conductors ( Ceo ) • Numerous cells were processed in vacuum systems MIP and Lesker cells prepared and characterized. An improvement in service life could be shown for the use of the stabilizer additives according to the invention in a photoactive layer and/or a fullerene layer.
  • Exemplary embodiments of layer systems 1 with stabilizer additives in photoactive layers 5 are shown below using MIP cells. For this purpose, numerous cells were manufactured in MIP systems and Lesker, and their efficiency and service life were characterized.
  • Fig. 2 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system 1 with a donor-acceptor system made of absorber: Ceo without stabilizer additive (reference), and each with the stabilizer Additives EA59, EA 61 and EA62 in a photoactive layer (A) 5 of the layer system 1 .
  • the organic electronic component is a photovoltaic element.
  • the short-circuit current density, the filling factor, the no-load voltage and the efficiency were each determined over a period of 100 h.
  • Layer system 1 differs only in the addition of the stabilizer additive.
  • the layer system of a MIP cell with volume heterojunction (bulk heterojunction) with a photoactive layer with the absorber and a stabilizer additive mixed into the absorber has the following structure for samples without stabilizer additive:
  • ITO Indium Tin Oxide
  • NDP9 commercial p-dopant from Novaled GmbH
  • the organics and the gold layer are deposited in a high vacuum on a substrate pre-coated with ITO.
  • the photoactive area defined by the overlap of ITO and gold is 6.4 mm 2 .
  • the samples are exposed in ambient air, without encapsulation, to radiation from the sun for 120 hours, simulated by xenon daylight lamps (1000 W/m 2 ).
  • the samples reach a temperature of 75 °C.
  • the illuminant irradiates the sample in such a way that the gold layer is turned away from the light.
  • the optoelectronic characterization of the samples is also carried out in air.
  • the efficiency of the photovoltaic element after aging for 120 h is summarized in Table 1 for the layer systems without stabilizer additive (reference) and with the stabilizer additives EA59, EA61 and EA62, each with the absorber in the photoactive layer.
  • Fig. 3 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system 1 with a donor-acceptor system made of absorber: Ceo without stabilizer additive (reference), and with the stabilizer additive EA50 in a photoactive layer (A) of the layer system 1 .
  • the layer system 1 differs only in the admixture of the stabilizer additive EA50 .
  • the layer system 1 of a MIP cell with volume heterojunction (bulk heterojunction) with a photoactive layer with the absorber and a stabilizer additive mixed into the absorber has the following structure for samples without stabilizer additive: and samples with stabilizer additive :
  • ITO Indium Tin Oxide
  • NDP9 commercial p-dopant from Novaled GmbH
  • NHT49 commercial hole conductor from Novaled GmbH Absorber :
  • the organics and the aluminum layer are deposited in a high vacuum on a substrate pre-coated with ITO.
  • the photoactive area, defined by the overlap of ITO and aluminum, is 6.4 mm 2 .
  • the samples are exposed, without encapsulation, to radiation from a sun for 1000 hours, simulated by xenon daylight lamps (1000W/m 2 ).
  • the samples reach a temperature of 75 °C.
  • the illuminant irradiates the sample in such a way that the gold layer is turned away from the light.
  • the optoelectronic characterization of the samples is also carried out in air.
  • the efficiency of the photovoltaic element after aging for 1000 hours is summarized in Table 2 for the layer systems without stabilizer additive (reference) and with the stabilizer additives EA50, each with the absorber in the photoactive layer.
  • Fig. 4 shows the in one embodiment
  • the layer system 1 of a MIP solar cell with volume heterojunction (bulk heterojunction) with a photoactive layer with the absorber and a stabilizer additive mixed into the absorber has the following structure for samples without stabilizer additive: and samples with stabilizer additive EA050 or EA052:
  • the organics and the gold layer are deposited in a high vacuum on a substrate pre-coated with ITO.
  • the photoactive area defined by the overlap of ITO and gold is 6.4 mm 2 .
  • the samples are initially stored in ambient air, without encapsulation, for 24 h and then exposed to radiation from the sun for a further 24 hours, simulated by halogen lamps (1000 W/m 2 ).
  • the illuminant irradiates the sample in such a way that the gold layer is turned away from the light.
  • the optoelectronic characterization of the samples is also carried out in air.
  • Fig. 5 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system 1 with a donor-acceptor system made of absorber! : Ceo without stabilizer additive (reference), and with the stabilizer additive EA55 in a photoactive layer (A) 5 of a layer system 1 .
  • the organic electronic component is a photovoltaic element.
  • the short-circuit current density, the filling factor, the no-load voltage and the efficiency was determined in each case in a temporal aging over 1000 h.
  • Layer system 1 differs only in the addition of the stabilizer additive.
  • the added stabilizer additive has the following structure for samples without stabilizer additive: and samples with stabilizer additive :
  • NDP9 commercial p-dopant from Novaled GmbH
  • NDN45 commercial n-dopant from Novaled GmbH
  • NHT49 commercial hole conductor from Novaled GmbH
  • the organics and the aluminum layer are deposited in a high vacuum on a substrate pre-coated with ITO.
  • the photoactive area defined by the overlap of ITO and aluminum, is 6.4 mm 2 .
  • the samples are exposed, without encapsulation, to radiation from a sun for 1120 hours, simulated by xenon daylight lamps (1000W/m 2 ).
  • the samples reach a temperature of 75 °C.
  • the illuminant irradiates the sample in such a way that the gold layer is turned away from the light.
  • the optoelectronic characterization of the samples is also carried out in air.
  • the efficiency of the photovoltaic element after aging for 1120 h is summarized in Table 3 for the layer systems without stabilizer additive (reference) and with the stabilizer additive EA55, each with the absorber! in the photoactive layer.
  • EA55 ascorbic acid, vitamin C
  • vitamin C is particularly suitable as a stabilizer additive for increasing the service life of an organic photovoltaic element.
  • ascorbic acid also leads to improved initial efficiency. Although a loss of initial efficiency was observed in a few cases, this is overcompensated over time by a reduced loss of efficiency over the course of the period of use of the photovoltaic element.
  • Fig. 6 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system 1 with a donor-acceptor system of absorber: Ceo without stabilizer additive (reference), with the stabilizer additive EA55 in a photoactive layer (A) 5, and with the stabilizer additive EA55 in a photoactive layer (A) and a transport layer (T) 4 of the layer system 1.
  • the organic electronic component is a photovoltaic element.
  • the short-circuit current density, the fill factor, the no-load voltage and the efficiency were each determined over a period of 1000 h.
  • Layer system 1 differs only in the addition of the stabilizer additive.
  • Absorberl was used as the absorber.
  • EA55 L-Ascorbic Acid, Vitamin C
  • a stabilizer additive mixed into a fullerene layer (Ceo ) 6 has the following structure for samples without stabilizer additive: with stabilizer additive in the photoactive layer: with stabilizer additive in the photoactive layer and the
  • NDP9 commercial p-dopant from Novaled GmbH
  • NDN45 commercial n-dopant from Novaled GmbH
  • NHT49 commercial hole conductor from Novaled GmbH Absorber :
  • the efficiency of the photovoltaic element after aging for 1160 h is summarized in Table 4 for the layer systems without stabilizer additive (reference) and with the stabilizer additive EA55, each with the absorber in the photoactive layer.
  • the stabilizer additive EA55 is either only in the photoactive layer (A) or both in the photoactive layer (A) and in the electron
  • Transport layer (T).
  • the admixture of the stabilizer additive EA055 in the absorber layer or in the electron conduction layer (ETL layer) Ceo leads to a significant improvement in the efficiency of the photovoltaic element after aging.
  • Fig. 7 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a donor-acceptor system with a layer system 1 of Absorber4: Ceo without stabilizer additive (reference), and with the stabilizer additive EA55 in a photoactive layer (A) 5 one Layer system 1 (A) .
  • the organic electronic component is a photovoltaic element.
  • the short-circuit current density, the fill factor, the no-load voltage and the efficiency were each determined over a period of 1000 h.
  • Layer system 1 differs only in the addition of the stabilizer additive.
  • the structure of the layer system 1 corresponds to the structure according to FIG. 6 , absorber 4 being used instead of absorber 1 .
  • the admixture of the stabilizer additive EA055 in the absorber layer (A) leads to a significant improvement in the efficiency of the photovoltaic element after aging.
  • Fig. 8 shows in one embodiment the short-circuit current density, the fill factor, the open-circuit voltage and the efficiency of organic electronic components with a layer system 1 with a donor-acceptor system of absorber3: Ceo without stabilizer additive (reference), with the stabilizer additive EA55 in a photoactive layer (A), and with the stabilizer additive EA55 in a fullerene layer (T) of a layer system 1.
  • the organic electronic component is a photovoltaic element.
  • the short-circuit current density, the fill factor, the no-load voltage and the efficiency were each determined over a period of 200 h.
  • Layer system 1 differs only in the addition of the stabilizer additive.
  • the structure of the layer system 1 corresponds to the structure according to Fig.
  • the conductivity of Ceo layers with 5%, 10% or 20% of the commercial n-dopant NDN45 from Novaled GmbH was measured with and without the stabilizer additive EA55 (L-Ascorbic Acid, Vitamin C) in a proportion of 5% by weight % measured.
  • EA55 L-Ascorbic Acid, Vitamin C
  • An n-doping with 5% by weight, 10% by weight and 20% by weight with NDN45 and with an additional stabilizer additive EA055 of less than 5% by weight showed no significant difference to corresponding layers without the stabilizer -Additive EA055.
  • the conductivity increases linearly depending on the proportion of n-doping with the dopant NDN45. This shows that adding the stabilizer additive to stabilize an n-layer does not negatively affect the conductivity of this layer.

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Abstract

L'invention concerne un système stratifié pour un composant électronique organique, comprenant une première électrode (3), une seconde électrode (7) et au moins une couche photoactive (5) et/ou au moins une couche de fullerène (6). Ladite couche photoactive et/ou ladite couche de fullerène sont placées entre la première électrode et la seconde électrode; et ladite couche photoactive et/ou ladite couche de fullerène ont au moins un additif stabilisant. L'invention concerne également un composant électronique comportant ce système stratifié avec au moins un additif stabilisant, ainsi que l'utilisation de ce système stratifié avec au moins un additif stabilisant dans un composant électronique organique.
EP21827587.3A 2020-12-01 2021-11-30 Système stratifié pour composant électronique organique Pending EP4256632A1 (fr)

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