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WO2010139782A1 - Élément de construction organique absorbant la lumière - Google Patents

Élément de construction organique absorbant la lumière Download PDF

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Publication number
WO2010139782A1
WO2010139782A1 PCT/EP2010/057825 EP2010057825W WO2010139782A1 WO 2010139782 A1 WO2010139782 A1 WO 2010139782A1 EP 2010057825 W EP2010057825 W EP 2010057825W WO 2010139782 A1 WO2010139782 A1 WO 2010139782A1
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oligomer
component according
monomers
monomer
conjugated
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German (de)
English (en)
Inventor
Karsten Walzer
Christian Uhrich
Martin Pfeiffer
Dirk Hildebrandt
Marion Bohnert
Gunter Mattersteig
Olga Tsaryova
Steve Zaubitzer
Serge Vetter
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Heliatek GmbH
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Heliatek GmbH
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • 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
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • H10K30/211—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions comprising multiple junctions, e.g. double heterojunctions
    • 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
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/40—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising a p-i-n structure, e.g. having a perovskite absorber between p-type and n-type charge transport layers
    • 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
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • 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 light-absorbing organic component, in particular an organic photovoltaic solar cell having a contact and a mating contact and a region of organic material or organic materials, which is electrically connected to the contact and the mating contact, wherein in the organic region, a photoactive region with a photoactive heterojunction is formed between a hole-conducting organic material and an electron-conducting organic material.
  • Organic solar cells consist of a sequence of thinner ones
  • Layers (which are typically each one to one micron thick) of organic materials, which are preferably vapor-deposited in vacuum or spin-coated from a solution.
  • the electrical contacting can be achieved by metal layers, transparent conductive oxides (TCOs) and / or transparent conductive polymers (PEDOT-PSS, PANI) take place.
  • a solar cell converts light energy into electrical energy.
  • photoactive is understood here, namely the conversion of light energy into electrical energy.
  • solar cells do not directly generate free charge carriers by light, but excitons are first formed, ie electrically neutral excitation states (bound electron-hole pairs). Only in a second step, these excitons are separated into free charge carriers, which then contribute to the electric current flow.
  • organic-based devices over conventional inorganic-based devices (semiconductors such as silicon, gallium arsenide) is the sometimes extremely high optical absorption coefficients (up to 2 ⁇ 10 5 cm -1 ), which allow efficient absorber layers of just a few nanometers Thickness produce, so that offers the opportunity to produce very thin solar cells with low material and energy costs.
  • Further technological aspects are the low costs, the organic semiconductor materials used being very cost-effective when produced in large quantities; the possibility of producing flexible large-area components on plastic films, and the almost unlimited possibilities of variation and the unlimited availability of organic chemistry.
  • organic solar cells Since no high temperatures are required in the production process (substrate temperatures of a maximum of 110 ° C. are not exceeded), it is possible to produce organic solar cells as components both flexibly and over a large area on inexpensive substrates, eg metal foil, plastic foil or synthetic fabric. This opens new Fields of application that remain closed to conventional solar cells. Due to the almost unlimited number of different organic compounds, the materials can be tailored to their specific task.
  • n or p denotes an n- or p-type doping, which leads to an increase in the density of free electrons or holes in the thermal equilibrium state.
  • i-layer designates an undoped layer (intrinsic layer).
  • One or more i-layer (s) may in this case consist of layers of a material as well as a mixture of two materials (so-called interpenetrating networks). in the
  • the pairs of charge carriers in organic semiconductors are not free after absorption, but because of the less pronounced attenuation of the mutual attraction they form a quasiparticle, a so-called exciton.
  • organic solar cells do not have sufficiently high fields to separate the excitons, the exciton separation at photoactive interfaces is completed.
  • the photoactive interface can be used as an organic donor-acceptor interface [CW. Tang, Appl. Phys. Lett. 48 (1986) 183] or an interface to an inorganic semiconductor [B. O'Regan, M. Grätzel, Nature 1991, 353, 737])].
  • the excitons pass through diffusion to such an active interface, where electrons and holes are separated. This can lie between the p (n) layer and the i-layer or between two i-layers.
  • the electrons are now transported to the n-area and the holes to the p-area.
  • the transport layers are transparent or largely transparent materials with a wide band gap (wide-gap).
  • wide-gap materials here materials are referred to, the absorption maximum in the wavelength range ⁇ 450 nm, preferably at ⁇ 400 nm.
  • phase separation The advantage of mixed layers is that the generated excitons only travel a very short distance until they reach a domain boundary where they are separated. The removal of the electrons or holes is carried out separately in the respective materials. Since in the mixed layer the materials are in contact with each other everywhere, it is crucial in this concept that the separate charges have a long service life on the respective material and that there are closed percolation paths for each type of charge to the respective contact from each location. These closed percolation paths are usually realized by a certain phase separation in the mixed layer, ie the two components are not completely mixed, but there are (preferably crystalline) nanoparticles of one material in the mixed layer. This partial segregation is referred to as phase separation.
  • the low-recombination diffusion of excitons to the active interface therefore plays a critical role in organic solar cells.
  • the exciton diffusion length In order to make a contribution to the photocurrent, therefore, in a good organic solar cell, the exciton diffusion length must at least be of the order of magnitude of the typical penetration depth of the light, so that the greater part of the light can be used.
  • the already mentioned possible high absorption coefficients are particularly advantageous for the production especially thin organic solar cells.
  • this Nah instrument the molecules serves both the low-loss transport of excitons and after their separation into free charge carriers the transport of electrons or holes.
  • a high mobility for charge carriers in these organic absorber layers is therefore another prerequisite for their usability.
  • one of the components in an organic mixed layer of two different organic components is preferably electronically conductive and the other component is preferably conductive holes.
  • WO 00/33396 discloses the formation of a so-called interpenetrating network of two organic materials. alien in the absorber layer: A layer contains a colloidally dissolved substance which is distributed in such a way that two networks form in the bulk material, each having closed charge carrier paths, so that each type of charge carrier (holes and electrons) lies on closed conduction paths of each material with very little loss to the external contacts (percolation mechanism).
  • the task of light absorption takes over in such a network either only one of the components or both.
  • the advantage of this mixed layer is that the generated excitons only have to travel a very short distance until they reach a domain boundary where they are separated. The removal of the electrons or holes is carried out separately.
  • One contact metal has a large and the other a small work function, so that a Schottky barrier is formed with the organic layer [US 4127738].
  • the active layer consists of an organic semiconductor in a gel or binder [US 03844843, US 03900945, US 04175981 and US 04175982].
  • a layer contains two or more kinds of organic pigments having different spectral characteristics [JP 04024970].
  • a layer contains a pigment which generates the charge carriers, and additionally a material which removes the charge carriers [JP 07142751].
  • Tandem cells can be further improved by using p-i-n structures with doped transport layers of large band gap [DE 10 2004 014046 A1].
  • P3AT Poly (3-alkylthiophene) (P3AT).
  • the evidence of network formation was obtained in this work by X-ray diffraction and transmission electron microscopy.
  • P3HT: PCBM polymer blend the group of Yang Yang (Nature Materials 4 (2005) 864) showed that even through the choice of suitable growth rates, formation of preferred molecular orders can be made which allow solar cell efficiencies of up to 3.6%.
  • the successfully used polymer P3HT is a poly-thiophene with a hexyl chain attached to the 3rd carbon atom. That is, a six C-atom side chain is used.
  • OFETs organic field effect transistors
  • the difference between solar cells and OFETs is as follows: OFETs should have a preferred charge carrier transport parallel to the substrate. Solar cells, on the other hand, are intended to deliver their charge carriers perpendicular to the substrate as quickly as possible and with little loss to the outer electrodes, which are generally flat, and in a frequently used arrangement charge transport layers are incorporated between the absorbent layer (s) and the electrodes. From this it can be deduced that the molecular structures in solar cells should be different from those in OFETs.
  • P3ATs Poly-3-alkyl-thiophene
  • Another aspect is the substitution pattern according to which the side chains are attached to the monomer. Consistent studies by various groups show that polymers in which each ring of the backbone carries a side group show better phase separation to PCBM than those that also contain side chain rings. For example, Koppe [Advanced Functional Materials 17 (2007) 1371] reports a comparison of P3HT: PCBM with C6TT-PCBM, in which the polymers differ only in that C6TT is a poly-thiophene with hexyl side groups, in which every third Thiophene is unsubstituted, whereas P3HT has a hexyl side group on each thiophene. In C6TT, sufficient phase separation to PCBM is no longer achieved, which leads to significantly poorer solar cell properties than with P3HT: PCBM. This is another indication that the molecular neighborhood in the active layer plays a crucial role in the efficiency of an organic solar cell.
  • the invention is thus based on the object of specifying a photoactive component which has improved efficiency.
  • a substrate electrode or other organic layer / layers
  • charge transport perpendicular to the substrate plane is preferred in that the pi-electron systems of adjacent molecules overlap and in that the pi-electron systems are parallel to the substrate, which allows preferential charge transport perpendicular to the substrate.
  • Oligomers in the context of the invention are substances which are formed from at least one organic material which has a precisely defined molecular structure
  • monomers Number, but at least two and typically no more than twenty designated as monomers repeating units of at least four atoms from the group C, N, S, Si, Se, and P, wherein at least two of these repeating units are identical.
  • the monomers are preferably pronounced as cyclic compounds with delocalized pi-electron system.
  • a monomer in the context of the present invention is an organic molecular substructure with a common pi-electron system formed from at least four atoms from the group C, N, S, Si, Se, P.
  • Another aspect is the light absorption. This becomes maximum when the longitudinal axes of the preferred as a rod-shaped pronounced oligomer molecules are orthogonal to the direction of light incidence. If one assumes perpendicular incidence of light on the substrate, it turns out that it is particularly advantageous for high light absorption when the molecules as shown in Fig. Ia) and Fig. Ib) are on the substrate, whereas standing molecules, as in Fig. Ic) outlined, absorb less light.
  • a molecular arrangement as outlined in FIG. 1 b is particularly advantageous for organic light-absorbing components, in particular solar cells.
  • the oligomer is characterized by at least two, but preferably four to six non-conjugated side chains wherein the backbone of at least two of these side chains comprises exactly three atoms from the group consisting of C, Si, O, S, Se, N, P in linear sequence ,
  • Another essential aspect of this invention is that the molecular proximity of the oligomers produces a nanocrystalline structure which is designed so that preferential electrical charge transport is perpendicular to the substrate, resulting in higher device efficiency due to lower contact resistances.
  • a molecular arrangement according to FIG. Ib) is particularly advantageous.
  • At least one of the monomers is a heterocycle.
  • the monomer is extended by at least one and at most eight further fused cycles.
  • the monomer has one of the following basic structures, wherein X and Y are independently selected from a group consisting of O, S, Se, CR3R4, N-R3:
  • the monomers in any selected order form an oligomer, wherein the oligomer carries a total of at least two side chains.
  • the monomers in the oligomer have, in addition to the direct bond via C-C, a further bridge C-S-C, C-CR3R4-C, C-NR3-C or C-O-C and have the following basic structure
  • Z is selected from the group consisting of S, CR3R4, NR3, or O.
  • the monomers in the oligomer have a further bridging via a benzene ring and one of the following basic structures
  • the oligomer carries one or more further side chains which, however, each comprise only n ⁇ 3 atoms from the group consisting of C, Si, O, S, Se, N, P in linear sequence.
  • the oligomer is an acceptor-donor-acceptor or donor-acceptor-donor molecule, as disclosed in WO 002006092134 A1.
  • the oligomer is a molecule which has four or more carries six side chains and has mirror and / or point symmetry.
  • the oligomer is a molecule comprising a monorange sequence of 5 consecutive conjugated monomers, wherein the 1st, 2nd, 4th and 5th monomer each carry a non-conjugated side chain ,
  • the oligomer is a molecule which comprises a monomer sequence of 5 consecutive conjugated monomers, and the second and fourth monomers each have one side chain and the first and fifth monomers each have two Carries side chains.
  • the oligomer is a molecule comprising a monomer sequence of 5 consecutive conjugated monomers, wherein in each case the 1st and 5th or the 2nd and 4th monomer are each two non-conjugated monomers Carry side chains.
  • the oligomer is a molecule which comprises a monomer sequence of 6 consecutive conjugated monomers, where in each case the 1st, 2nd, 5th and 6th monomer or the 1st, 3rd ., 4th and 6th monomer each carries a non-conjugated side chain.
  • the oligomer is a molecule comprising a monomer sequence of 6 consecutive conjugated monomers, wherein the 1st and 6th monomers, or the 2nd and 5th monomers each have two non-conjugated side chains wear.
  • the oligomer is a molecule which is at least includes two n-propyl groups as a side chain.
  • the oligomer is a molecule with the following monomer sequence:
  • the oligomer is a molecule which is referred to as
  • MeDCV with the structure or one of the following acceptor-like monomers with or without additional peripheral substituents: cyano-bicyano or tricyano-vinylene, bridged dithiophene unit with electron-withdrawing bridge, benzothiadiazole, oxadiazole, Triazole, benzimidazole, quinolines, quinoxalines, pyrazolines, naphthalene-dicarboxylic acid anhydrides, naphthalenedicarboxylic acid imides, naphthalenedicarboxylic acid imidazoles, halogenated homo- and heterocycles, di- or triarylboryl, dioxaborine derivatives, quinoid structures, aryls with ketone or dicyanomethane substituents.
  • 1 is a schematic representation of the orientation of the molecule longitudinal axis to the substrate, in
  • Fig. 2 is an illustration of the current-voltage characteristics in various absorber materials and in
  • organic solar cells of the following layer sequence were produced:
  • Support material glass / ground electrode indium tin oxide (ITO) / hole transport layer (HTL) / undoped HTL / absorber 1 oligomer DCV5T-X4 with variable side chain lengths x ethyl (Et), propyl (Pr), or Butyl (Bu) / absorber 2 fullerene C60 / electron transport layer (ETL) / cover electrode aluminum.
  • the molecular structure of the oligomeric material DCV5T-X4 is as follows:
  • the cause of the lower stress in ethyl is a more red-absorbing absorption of ethyl based on lower propyl formation. This can be seen from the absorption spectra of the three absorber materials discussed in FIG.
  • short side chain oligomers are generally advantageous for solar cells because they meet various organic solar cell requirements:
  • both the monomers having such side chains and the oligomers formed therefrom are up to a typical oligomer length of about 7 or 8 repeat units (Mono - Meren) soluble in common solvents and thus manageable.
  • the formation of a molecular order of proximity is possible. This allows the desired formation of nanocrystalline phases, which are a prerequisite for the formation of interpenetrating networks.
  • intermolecular charge transport across the longitudinal axis of the rod-shaped oligomers is possible as a result of the short-chain side chains by means of tunneling processes.
  • the molecules are small enough that they can be vacuum deposited by thermal sublimation. Alternatively, their deposition from carrier gases or from solution is possible, which is e.g. can be done by printing, spraying, pouring or spin coating.
  • Oligomers consisting of monomers with different lateral chains are composed, are a further advantageous possibility for structure formation. It may be particularly advantageous to use such different side chains, which show mutually preferred interactions. In this way, a preferred proximity of the molecules can be achieved, which can be used for a low-loss charge transport of the oligomer layer.
  • triatomic side chains are attached to oligomers of five or six heterocycles.
  • the molecules are selected so that they follow the structure described in WO 2006-092134 Al: At least one end, better at both ends of the oligomer chain each an acceptor group (in the present example, a Dicyanovinyl unit) attached, the electronic Properties of the substance.
  • acceptor group in the present example, a Dicyanovinyl unit
  • oligothiophenes having side chains of 3 non-H atoms in linear sequence other than alkane chains, e.g.
  • Oligomers which are not oligothiophenes, eg f) oligomers containing different monomers, eg

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  • Chemical & Material Sciences (AREA)
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Abstract

L'invention concerne un élément de construction organique absorbant la lumière, en particulier une cellule solaire photovoltaïque organique comportant un contact et un contact complémentaire, ainsi qu'une zone comportant une ou plusieurs matières organiques, qui est reliée électriquement avec le contact et le contact complémentaire. Dans la zone de matière organique est formée une zone photoactive pourvue d'une hétérojonction photoactive entre une matière organique de transport de trous et une matière organique de transport d'électrons.
PCT/EP2010/057825 2009-06-05 2010-06-04 Élément de construction organique absorbant la lumière Ceased WO2010139782A1 (fr)

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DE102009024299.6 2009-06-05
DE102009024299 2009-06-05
DE102009036110.3 2009-08-05
DE102009036110A DE102009036110A1 (de) 2009-06-05 2009-08-05 Licht absorbierendes organisches Bauelement

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2014128281A1 (fr) * 2013-02-21 2014-08-28 Heliatek Gmbh Matériau organique photoactif pour composants optoélectroniques
CN111057390A (zh) * 2019-12-12 2020-04-24 安徽师范大学 线性共轭异吲哚多吡咯色素及其制备方法

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Publication number Priority date Publication date Assignee Title
KR101860084B1 (ko) * 2012-07-06 2018-05-23 삼성전자주식회사 유기 광전 재료, 상기 유기 광전 재료를 포함하는 유기 광전 소자 및 이미지 센서
DE102013101713B4 (de) * 2013-02-21 2020-10-01 Heliatek Gmbh Photoaktives, organisches Material für optoelektronische Bauelemente

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