EP4008028A1 - Composé semiconducteur organique avec un groupe indol, composant optoélectronique organique comprenant ledit composé et utilisation dudit composé - Google Patents

Composé semiconducteur organique avec un groupe indol, composant optoélectronique organique comprenant ledit composé et utilisation dudit composé

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Publication number
EP4008028A1
EP4008028A1 EP20760757.3A EP20760757A EP4008028A1 EP 4008028 A1 EP4008028 A1 EP 4008028A1 EP 20760757 A EP20760757 A EP 20760757A EP 4008028 A1 EP4008028 A1 EP 4008028A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
group
compound
alkoxy
aryl
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
EP20760757.3A
Other languages
German (de)
English (en)
Inventor
Ludovic Coutable
Olga Gerdes
Dirk Hildebrandt
Martin PFEIFFER-JACOB
Nina SCHAEFFELER
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 EP4008028A1 publication Critical patent/EP4008028A1/fr
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • H10K85/657—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
    • 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
    • H10K30/50—Photovoltaic [PV] devices
    • 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

  • Organic semiconducting compound with an indole group organic optoelectronic component with one
  • the present invention relates to a compound of the general formula I, optoelectronic components having such a compound
  • connection as well as the use of such a connection in optoelectronic components.
  • Organic optoelectronic components can be displays, data memories or transistors, for example. These components also include organic optoelectronic components, in particular organic photoactive components, in particular solar cells and photodetectors, which have a photoactive layer in which charge carriers, when electromagnetic radiation is incident,
  • Photoactive optoelectronic components enable the conversion of electromagnetic radiation using the
  • Optoelectronic components comprise at least two electrodes, one electrode being applied to a substrate and the other functioning as a counter electrode. At least one photoactive layer, preferably one, is located between the electrodes
  • organic photoactive layer organic photoactive layer.
  • further layers for example charge carrier transport layers, can be placed between the
  • the international patent application WO2017114937A1 discloses an organic compound, the organic compound being characterized by high absorption in the short-wave spectral range of visible light.
  • the use of this compound for an organic electronic component and a method for producing the connection are also disclosed.
  • absorber materials disclosed in the prior art are indeed suitable for photoactive layers in organic solar cells, but the efficiency of the needs to be improved
  • the invention is therefore based on the object, organic
  • an optoelectronic component with at least one such connection and the use of such compounds in an optoelectronic component, the disadvantages mentioned not occurring, and in particular the absorption of electromagnetic Radiation is improved and / or the efficiency of organic solar cells is increased.
  • RI is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl;
  • R4 is selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl and alkenyl, and an electron-withdrawing alkyl group with at least one CC- Double bond, where H can be substituted by CN or F; at least one Al, A2, A3 or A4 each independently of one another the group Ia where * denotes the linkage to the compound of the general formula I;
  • Z is selected from the group consisting of O, S, Se, and N-R8, where R8 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl;
  • Y3 is N or C-R9, where R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted;
  • Y4 is N or C-R10, where RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted; where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure; and
  • R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H may be substituted by CN or F;
  • A1, A2, A3 or A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and amino; and A5 is selected from the group consisting of H, alkyl, alkoxy and group Ib
  • X is selected from the group consisting of O, S, Se, and N-R7, where R7 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl;
  • Y1 is N or C-R5, where R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted;
  • Y2 is N or C-R6, where R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted;
  • R5 and R6 can be homocyclically or heterocyclically linked to one another in the form of a ring structure
  • R2 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F.
  • the present invention relates in particular to A-D-A dyes of the compound of general formula I, the central
  • Structural unit is an indole unit. Due to the presence in particular of a furan or a thiophene group on the indole unit and at least one double bond on the furan or thiophene group, which are preferably arranged adjacent to at least one of the electron-withdrawing groups, the
  • group Ia and / or group Ib has at least one electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, particularly preferably group Ia and group Ib at least one electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F.
  • R9 and RIO are not linked to one another homocyclically or heterocyclically in the form of a ring structure.
  • R5 and R6 are not homocyclically or heterocyclically linked to one another in the form of a ring structure.
  • the central indole unit in particular the pyrrole ring of the indole unit, has no further condensed aromatic system.
  • the pyrrole rings are condensed units which contain furan, in particular benzofurans.
  • substitution is understood to mean, in particular, the replacement of H by a substituent.
  • a substituent includes, in particular, all atoms and groups of atoms except hydrogen
  • halogen an alkyl group
  • the alkyl group can be linear or branched, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, an aryl group, or a heteroaryl -Group.
  • a halogen is understood in particular to be F, Ci or Br, preferably F.
  • none of the C of an alkyl group has been replaced by a heteroatom.
  • R2 and R3 are not an H atom.
  • either Al or A4 is an H atom.
  • Al and A4 are an H atom.
  • a heteroatom in particular a heteroatom in general formula I, is understood in particular to mean an atom selected from the group consisting of O, S, Se, Si, B, N or P, preferably selected from the group consisting of O, S, Se or N.
  • the central indole unit in particular the pyrrole ring of the indole unit, has at least one condensed homocyclic or heterocyclic ring structure.
  • the one formed between R5 and R6 and / or between R9 and RIO is formed between R5 and R6 and / or between R9 and RIO
  • Ring structure has at least one double bond, preferably an aromatic system.
  • the compound according to the invention relates in particular to so-called “small molecules”.
  • Small molecules are understood to mean, in particular, non-polymeric organic molecules with monodisperse molar masses between 100 and 2000 g / mol, which are under normal pressure
  • the small molecules are photoactive, photoactive being understood to mean that the
  • Molecules change their state of charge and / or their polarization state when exposed to light.
  • the photoactive molecules show in particular an absorption of electromagnetic radiation in a certain wavelength range, with absorbed electromagnetic radiation, that is to say photons, being converted into excitons.
  • Yl, Y2, Y3, and Y4 are each independently selected from the group consisting of N, CH, CF, C-CH 3 , C-CF 3 , CC 2 H 5 , CC 3 H 8 , C-OCH 3 , C-OC 2 H 5 , C-SCH 3 , C-SC 2 H 5 .
  • cyclic or open-chain alkyl groups of the compounds according to the invention linear or branched, the alkyl groups being C1-C5-alkyl groups.
  • at least one of the positions Y1, Y2, 3 and Y4 is N
  • at least one position Y1 and Y2 is preferably N
  • / or at least one position Y3 and Y4 N is particularly lowers the highest position with electrons occupied molecular orbital (HOMO) achieved, the absorption spectrum of the compound according to the invention shifting towards shorter wavelengths.
  • HOMO electrons occupied molecular orbital
  • Y1, Y2, Y3 and Y4 are each CH.
  • the two five rings are each further substituted or unsubstituted furan rings.
  • Spectral range of approx. 500 - 700 nm can be determined.
  • absorber materials with improved absorption in a wavelength range of the blue / green range of visible light are provided.
  • the central structural element of the compound according to the invention namely the central indole unit, is eminently suitable for obtaining compounds with the desired absorption properties.
  • the compounds according to the invention advantageously have sufficient thermal, chemical and electrochemical properties
  • the compounds according to the invention advantageously have charge carrier transport properties which make them suitable for use in organic optoelectronic components, in particular in organic
  • the Connection has very good transport properties, especially with particularly suitable energy levels.
  • the compounds according to the invention due to the central structural element of the indole unit, absorb electromagnetic radiation, in particular light in the visible spectral range, particularly well. In particular, this increases the efficiency of organic optoelectronic components and / or increases the charge carrier mobility in photoactive layers.
  • the compounds according to the invention advantageously show a high absorption coefficient.
  • the compounds according to the invention advantageously show a high absorption coefficient.
  • Idle oltage S Voc over 0.9 V, preferably about 0.94 V, more preferably greater than 0.95 V.
  • the compound is a compound of the general formula II
  • RI is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, iso-butyl and s-butyl;
  • R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy and alkyl;
  • X and Z are each independently O or S.
  • the compound is a compound of the general formula VII
  • RI is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, iso-butyl and s-butyl;
  • R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy and alkyl; and wherein Z is 0 or S; and where preferably Al or A4 is an H atom.
  • At least two Al, A2, A3 or A4 are each independently group Ia where the remaining Al, A2, A3 or A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and amino.
  • At least one Al, A2, A3 or A4 each independently of one another
  • R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, preferably R3 is an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F;
  • R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted;
  • RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted; and where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure.
  • At least two of the groups A1, A2, A3 or A4 are each independently one
  • R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, R3 is preferably an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F;
  • R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, and aryl, where H can in each case be substituted;
  • RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted; and where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure.
  • the compound is a compound of the general formulas III and / or IV, where RI is H or alkyl;
  • X and Z are each independently O or S;
  • Al, A3 and A4, or Al, A2 and A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl;
  • R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, R3 is preferred an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F; and
  • R4 is H
  • R5 and R6 are H.
  • X and Z are each independently O or S;
  • A2, A3 and A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl;
  • R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, R3 is preferred an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F; and
  • R4 is H
  • R5 and R6 are H.
  • A3 and A4 are each H.
  • X and Z are each independently O or S;
  • Al, A2 and A3 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, and partially fluorinated alkyl;
  • R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F, R3 is preferred an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F; and
  • R4 is H
  • R5 and R6 are H.
  • Compound of general formula I has an N at position Y1 and / or Y2 of formula Ia and at position Y3 and / or Y4 of formula Ha
  • the optical properties obtained are in particular in particular the absorption of light, more favorable than with comparable compounds with an atom other than 0.
  • X and Z are each independently O or S, with R5 and R6 preferably being H. This is how the
  • the compound is a compound of the general formula VIII and / or IX,
  • RI is H or alkyl
  • X and Z are each independently O or S;
  • R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted;
  • RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can each be substituted, and where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure ;
  • R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted;
  • R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted, and where R5 and R6 can be homocyclically or heterocyclically linked to one another in the form of a ring structure ; and
  • R5 and R6 are preferably H and R9 and RIO are H.
  • RI is H or alkyl
  • X and Z are each independently O or S;
  • R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted;
  • RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can each be substituted, and where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure ;
  • R5 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted;
  • R6 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted, and where R5 and R6 can be homocyclically or heterocyclically linked to one another in the form of a ring structure ; and
  • R5 and R6 are preferably H and R9 and RIO are H.
  • R3 is selected from the group consisting of H, alkyl, fluorinated alkyl, partially fluorinated alkyl, alkoxy, amino, aryl, and one
  • R3 is an electron-withdrawing alkyl group with at least a CC double bond
  • R2 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond
  • H can be substituted by CN or F
  • R2 is preferably an electron-withdrawing alkyl group with at least one CC double bond.
  • X and / or Z is O, in particular it is a substituted furan ring.
  • the absorption by the compound is preferably increased by at least one furan ring from groups Al, A2, A3, A4 or A5 on the central indole unit.
  • the groups A5 and at least one of the groups A1, A2, A3 and A4 are identical.
  • R4 is H, methyl, propyl or isopropyl, where X and Z are O, R4 is H, and R5 and R6 are H.
  • R2 of group Ib is an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F
  • R3 of group Ia is an electron-withdrawing alkyl group with at least one CC -Double bond, where H can be substituted by CN or F.
  • R2 and / or R3 has at least two C-C double bonds.
  • R2 and R3 are each independent of one another
  • Rll, R12 and R13 are each independently selected from the group consisting of H, halogen, CN, COO-alkyl, alkenyl,
  • R2 and / or R3 are each independent of one another
  • R11, R12, R13, R14, R15 and R16 are each independently selected from the group consisting of H, halogen, CN, COO-alkyl, alkenyl, alkynyl, alkoxy, cyclic or open-chain alkyl, and cyclic or open-chain alkenyl, where H may in each case be substituted by halogen or CN, with the proviso that R1 and R2 are not both H, with R1 and R2 preferably being CN.
  • a particularly good acceptor effect of the groups R2 and / or R3 can be achieved through a large number of CN groups.
  • R2 and R3 are each selected independently of one another from the group consisting of:
  • connection is selected from the group consisting of:
  • connection is F7 and / or F16
  • X is Z
  • R2 is R3
  • R5 is R9
  • R6 is RIO
  • Compound of the general formula I additionally has a five-ring or six-ring formed by R5 and R6 and / or R9 and RIO, the five-ring or six-ring can be in further positions
  • Organic single or tandem cells are known from the prior art.
  • the laid-open specification DE102004014046A1 discloses a photoactive component, in particular a solar cell, consisting of organic layers of one or more one on top of the other
  • Patent application WO201116108A1 discloses a photoactive component with an electrode and a counter electrode, with at least one organic layer system being arranged between the electrodes, with at least two photoactive layer systems and at least two different between the photoactive layer systems
  • Transport layer systems of the same charge carrier type characterized in that one transport layer system is energetically adapted to one of the two photoactive layer systems and the other transport layer system is transparent.
  • the object of the present invention is also achieved by providing an optoelectronic component with at least one inventive connection, in particular according to one of the exemplary embodiments described above. This results in particular for the optoelectronic component that has already been explained in connection with the connection according to the invention.
  • the optoelectronic component comprises a first electrode, a second electrode and a layer system, the layer system being between the first electrode and the second
  • Electrode is arranged, characterized in that at least one layer of the layer system has at least one compound according to the invention.
  • the efficiency of an organic optoelectronic component depends, among other things, on the absorption behavior of the connection, i.e. the absorber material. High absorption and absorption in a broad range of the available spectrum of electromagnetic radiation are particularly advantageous here, since photons of different wavelengths can thus be used to generate electrical current.
  • An optoelectronic component in particular an organic optoelectronic component, is in particular a Understood component having organic conductive or semiconducting materials, in particular a transistor
  • Solar cells with at least one compound according to the invention enable particularly efficient use of the short-wave spectrum of visible light.
  • An organic photovoltaic element is understood to mean in particular a photovoltaic element with at least one organic photoactive layer, the organic photoactive layer having at least one compound according to the invention.
  • a photoactive organic optoelectronic component enables electromagnetic radiation, for example in the wavelength range of visible light, to be converted into electrical current using the photoelectric effect.
  • Organic semiconductor materials that show sufficiently good absorption properties are required for the conversion.
  • the optoelectronic component is a solar cell, an FET, an LED or a photodetector, preferably an organic solar cell (OPV), an OFET, an OLED or an organic photodetector.
  • OLED organic solar cell
  • the organic electronic component has, in particular, an electrode and a counter electrode, an organic photoactive layer being arranged between the electrodes.
  • This organic photoactive layer has one for the
  • Optoelectronic component has an important function, in particular a charge carrier transport function, such as the transport of holes (p-conductive) or the transport of electrons (n-conductive).
  • a charge carrier transport function such as the transport of holes (p-conductive) or the transport of electrons (n-conductive).
  • the organic photoactive layer is
  • a photoactive layer in which excitons (electron-hole pairs) are formed by radiation from visible light, UV radiation and / or IR radiation.
  • the organic materials are printed, glued, coated, vapor-deposited or in the form of thin films or small volumes on the foils
  • the layer system has at least one photoactive layer
  • the photoactive layer which has at least one compound according to the invention.
  • the photoactive layer is arranged between the first electrode and the second electrode.
  • the layer system has at least two photoactive layers, preferably at least three photoactive layers, or preferably at least four photoactive layers, preferably absorber layers.
  • the organic solar cell has a photoactive layer which has at least one organic donor material in contact with at least one organic acceptor material, the donor material and the acceptor material having a donor-acceptor heterojunction, in particular also a so-called bulk heterojunction (BHJ),
  • BHJ bulk heterojunction
  • the photoactive layer has at least one compound according to the invention.
  • the optoelectronic component has at least one further layer, preferably at least one charge transport layer, in particular an electron transport layer and / or a hole transport layer.
  • the at least one charge transport layer in particular at least one electron transport layer and / or at least one
  • a tandem cell is understood in particular to mean that two functional cells are spatially stacked on top of one another and connected in series, preferably between a first electrode and a second electrode, with one or more intermediate layers being able to be arranged between the cells.
  • a multiple cell or multijunction cell is accordingly understood to mean that more than two functional cells are spatially stacked one on top of the other and connected in series, it being possible for an intermediate layer to be arranged between the cells.
  • the optoelectronic component has a substrate
  • Electrode is arranged on the substrate, in particular one of the electrodes of the optoelectronic component can be applied directly to the substrate.
  • the photoactive layer is a mixed layer of the at least one compound according to the invention and at least one further
  • Connections is formed, wherein the connections are preferably absorber materials.
  • optoelectronic component as a nip, ni, ip, pnip, pni, pip, nipn, nin, ipn, pnipn, or pipn cell or a combination of nip, ni, ip, pnip, pni, pip, nipn, nin, ipn, pnipn, or pipn cells that contain at least one i-layer are formed.
  • An i-layer is understood to mean in particular an intrinsic undoped layer.
  • One or more i-layers can consist of one material (planar heterojunctions, PHJ) or a mixture of two or more materials, so-called bulk heterojunctions (BHJ), which form an interpenetrating network
  • Gas phase deposition or solvent processing can be deposited, particularly preferably by means of vacuum processing.
  • the object of the present invention is also achieved by the use of a compound according to the invention in a
  • optoelectronic component preferably an organic one
  • optoelectronic component is provided, in particular according to one of the embodiments described above.
  • the use of the connection according to the invention in an optoelectronic component results in particular in the advantages that are already in connection with the connection according to the invention and the optoelectronic component with the at least one
  • Table 1 shows an overview of the melting points and absorption maxima (in nm and eV in the solvent (LM)) of these compounds according to the invention.
  • the associated absorption spectra of the compounds listed in Table 1 are shown in FIGS. 3 to 15.
  • the spectral data refer to a thickness of 30 nm
  • the optical properties were determined experimentally.
  • the absorption maxima Amax was determined with a dilute solution in a cuvette in dichloromethane using a photometer.
  • the measured absorption maxima of all the compounds described are between 530 and 610 nm.
  • the compounds according to the invention are distinguished by a
  • the compounds according to the invention thus make it possible to absorb photons over a relatively broad spectral range, which comprises a large proportion of the short-wave visible sunlight, and convert them into electrical energy.
  • “Integral” is understood to mean the area below a curve in the absorption spectrum, which is an important characteristic for the suitability of the material as a photoactive material.
  • the photovoltaic parameters idle oltage S Voc, short-circuit current Jsc and fill factor FF are each based on the same structure of a solar cell.
  • the compounds according to the invention ie their use as absorber materials in organic optoelectronic components, the current-voltage curve in a BHJ cell with the structure: glass with ITO / C60 (15 nm) / compound according to the invention was used
  • a transparent cover contact made of ITO (indium tin oxide) is applied to a glass substrate. ITO serves as an electrode, and that
  • Electron acceptor material and the respective compound according to the invention as hole acceptor material (donor material), followed by BPAPF (9, 9-bis [4- (N, N-bis-biphenyl-4-yl-amino) phenyl] -9H-fluorene) as hole transport layer ( HTL) and BPAPF doped with NDP9 (Novaled AG), followed by an electrode made of aluminum (see FIG. 2).
  • an H a methyl, ethyl, propyl or butyl group, in particular an isopropyl, isobutyl or s-butyl group, on the N of the pyrrole ring of the central indole unit is advantageous.
  • Further five rings (Ia, Ha) are preferably linked in the 2 'and 6' positions of the central indole unit.
  • the two outer five-rings (Ia, Ha) preferably each have a dicyanovinyl and / or a butadienyldicyano group.
  • FIG. 2 shows a schematic illustration of an embodiment of an optoelectronic component in cross section
  • FIG. 3 shows a graphic representation of the absorption spectrum of compound F1 and the current-voltage curve, a spectral external quantum yield and the fill factor of a BHJ cell with compound F1 measured on an organic optoelectronic component in the form of an organic solar cell;
  • FIG. 6 shows a graphic representation of the absorption spectrum of compound F4 and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with compound F4 measured on an organic optoelectronic Component in the form of an organic solar cell;
  • FIG. 11 shows a graphic representation of the absorption spectrum of compound F9 and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with compound F9 measured on an organic optoelectronic component in the form of an organic solar cell;
  • 13 shows a graphic representation of the absorption spectrum of compound F1 and the current-voltage curve, a spectral external quantum yield and the fill factor of a BHJ cell with compound F1, measured on an organic optoelectronic component in the form of an organic solar cell
  • 14 shows a graphic representation of the absorption spectrum of compound F12 and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with compound F12, measured on an organic optoelectronic component in the form of an organic solar cell
  • FIG. 1 shows an embodiment of a synthesis scheme for the synthesis of compounds according to the invention.
  • the compounds F1, F7, F13 and F16 are prepared according to a synthesis disclosed in the international applications WO2017114937A1 and WO2017114938A1.
  • the positions of the linkage of substituents (Ia, Ha) on the central indole unit are summarized in Table 3.
  • RI is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl
  • R4 is selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl and alkenyl; at least one Al, A2, A3 or A4 each independently of one another the group Ia
  • Z is selected from the group consisting of O, S, Se, and N-R8, where R8 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and aryl;
  • Y3 is N or C-R9, where R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl and aryl, where H can in each case be substituted;
  • Y4 is N or C-R10, where RIO is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl and aryl, where H can in each case be substituted; and where R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure; and R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F; the remaining A1, A2, A3 or A4 are each independently selected from the group consisting of H, halogen, CN, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, and amino;
  • connection is a
  • RI is preferably selected from the group consisting of H and alkyl
  • R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy and alkyl
  • X and Z are preferably each O or S, independently of one another.
  • the compound is a compound of the general formula VII where RI is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, iso-butyl and s-butyl; R4 is preferably selected from the group consisting of H, halogen, CN, alkoxy and alkyl; and where Z is O or S.
  • At least one Al, A2, A3 or A4 is each independently of one another
  • R3 is selected from the group consisting of H, alkoxy, alkyl, fluorinated alkyl, partially fluorinated alkyl, branched or linear, cyclic or open-chain alkyl, amino, aryl, alkenyl, and an electron-withdrawing alkyl group with at least one CC double bond, where H can be substituted by CN or F;
  • R9 is selected from the group consisting of H, halogen, alkoxy, branched or linear, cyclic or open-chain alkyl, alkenyl, aryl, where H can in each case be substituted;
  • R9 and RIO can be homocyclically or heterocyclically linked to one another in the form of a ring structure.
  • the compound is a compound of the general formulas III and / or IV, where RI is selected from the group consisting of H methyl,
  • R4 is H
  • R5 and R6 are H.
  • Al, A3 and A4 are H (formula V) in formula III, and Al, A2 and A4 H (formula VI) in formula IV,
  • X and Z are each independently 0 or S;
  • R5 and R6 are preferably H.
  • the compound is a compound of the general formula VIII and / or IX,
  • Ring structure can be linked homocyclically or heterocyclically; where R5 and R6 are preferably H and R9 and RIO are H.
  • R2 and R3 are each independent of one another
  • R11, R12 and R13 are each independently selected from the group consisting of H, halogen, CN, COO-alkyl, alkenyl, alkynyl, alkoxy, cyclic or open-chain alkyl, cyclic or open-chain alkenyl, where H is each substituted by halogen or CN can, with the proviso that Rll and R12 are not both H, with Rll and R12 preferably being CN.
  • R2 and R3 are each independently selected from the group consisting of:
  • the compound is selected from the group consisting of:
  • connection is F7 and / or F16
  • Fig. 2 shows a schematic representation of a
  • the optoelectronic component comprises a first electrode 1, a second electrode 2 and a layer system 7, the Layer system 7 is arranged between the first electrode 1 and the second electrode 2. At least one layer of the layer system 7 has at least one compound according to the invention.
  • the optoelectronic component is an organic solar cell, an OFET, an OLED or an organic photodetector.
  • a structure of an organic solar cell known from the prior art consists of a pin or nip diode (Martin Pfeiffer, "Controlled doping of organic vacuum deposited dye layers: basics and applications", PhD thesis TU-Dresden, 1999, and
  • a pin solar cell consists of one
  • a nip solar cell consists of a substrate attached to it
  • n-layer (s), i-layer (s), p-layer (s) and a cover contact subsequent mostly transparent ground contact, n-layer (s), i-layer (s), p-layer (s) and a cover contact.
  • the optoelectronic component is a solar cell.
  • the solar cell has a substrate 1, e.g. B. made of glass, on which there is an electrode 2, the z. B. ITO includes.
  • Arranged thereon are an electron-transporting layer 3 (ETL) and a photoactive layer 4 with at least one
  • ETL electron-transporting layer 3
  • a p-type donor material e.g. B. C60 fullerene
  • an n-type acceptor material e.g. B. C60 fullerene
  • a flat heterojunction or as a volume heterojunction.
  • a p-doped hole transport layer 5 HTL
  • the electrode 6 made of aluminum.
  • Layer system 7 has at least one photoactive layer 4, preferably an absorber layer, the at least one photoactive layer 4 having the at least one compound according to the invention.
  • Layer system 7 has at least two photoactive layers, preferably at least three photoactive layers, or preferably at least four photoactive layers.
  • the photoactive layer is a mixed layer of the at least one compound according to the invention and at least one further compound, or as a
  • Compounds are preferably absorber materials.
  • FIG 3 shows a graphic representation of the absorption spectrum of the compound Fl (A), and the current-voltage curve, a spectral external quantum yield and the fill factor of a BHJ cell with the compound Fl measured on an organic optoelectronic component in the form of an organic solar cell (B. ).
  • the absorption spectra (optical density over wavelength in nm) were measured for 30 nm thick vacuum-deposited layers of the respective compounds F1 to F13 on quartz glass.
  • the current-voltage curve contains key figures that characterize the organic solar cell. Financial Highlights here are the fill factor FF, the idle S oltage Voc and the short-circuit current Jsc.
  • the BHJ cell has a layer of C60 with a thickness of 15 nm on the ITO layer. Compound Fl together with C60 was applied to this layer in a thickness of 30 nm.
  • This layer is followed by a layer of BPAPF with a thickness of 10 nm, on top of which there is another layer comprising BPAPF and NDP9 with a thickness of 30 nm.
  • the proportion of BPAPF in this layer is 10 percent by weight, based on the entire layer.
  • NDP9 with a thickness of 1 nm, followed by an aluminum layer with a thickness of 100 nm.
  • the compound F1 also shows particularly good vaporizability at temperatures of 240 ° C to 255 ° C final temperature.
  • FIG. 4 shows a graphic representation of the absorption spectrum of the compound F2 (A), and the current-voltage curve, a spectral external quantum yield and the fill factor of a BHJ cell with the compound F2 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F2: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 61.7%
  • the idle oltage S Voc 1.02 V the idle oltage S Voc 1.02 V
  • FIG. 5 shows a graphic representation of the absorption spectrum of the compound F3 (A), and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with the compound F3 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • heteroj unction - BHJ is.
  • the fill factor FF is 73.8%
  • the idle oltage S Voc 0.98 V the short-circuit current Jsc of 11.5 mA / cm2.
  • F3 shows particularly good transport properties with a high fill factor FF.
  • FIG. 6 shows a graphic representation of the absorption spectrum of the compound F4 (A), and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with the compound F4 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F4: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 72.1%
  • the idle oltage S Voc 0.94 V is 72.1%
  • the cell efficiency of such an optoelectronic component, in particular a solar cell, with the connection F4 is 8.07%.
  • FIG. 7 shows a graphic representation of the absorption spectrum of the compound F5 (A), and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with the compound F5 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F5: C60 (30 nm, 3: 2, 50 ° C) / BPAPF (10 nm) / BPAPF: NDP9 (30 nm, 10% wt NDP9) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 62.3%
  • FIG 8 shows a graphic representation of the absorption spectrum of the compound F6 (A), and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with the compound F6 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • NDP9 (30nm, 10% wt NDP9) / NDP9 (lnm) / Al (100nm) was determined, the photoactive layer being a
  • BHJ Volume heterojunction
  • FIG. 9 shows a graphic representation of the absorption spectrum of the compound F7 (A), and the current-voltage curve, a spectral external quantum yield and the filling factor of a BHJ cell with the compound F7 measured on an organic optoelectronic component in the form of an organic solar cell (B ).
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F7: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF 63, 6% is the fill factor FF 63, 6%, the idle oltage S Voc 1.0 V and short circuit current Jsc 9.8 mA / cm2.
  • the cell efficiency of such an optoelectronic component, in particular a solar cell, with the connection F1 is 6.23%.
  • Fig. 10 is a graph showing the absorption spectrum of Compound F8 (A), and the current-voltage curve, a
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F8: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 67.9%
  • the idle oltage S Voc 0.98 V the idle oltage S Voc 0.98 V
  • the short-circuit current Jsc 12.8 mA / cm2.
  • connection F8 shows a particularly stable behavior at
  • Fig. 11 is a graph showing the absorption spectrum of the compound F9 (A), and the current-voltage curve, a
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F9: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 70.3%
  • the idle oltage S Voc 0.98 V is 70.3%
  • Fig. 12 is a graph showing the absorption spectrum of Compound F10 (A), and the current-voltage curve, a
  • heteroj unction - BHJ is.
  • the fill factor FF is 56.5%
  • Component in particular a solar cell, with the connection Fl is 6.73%.
  • Fig. 13 shows a graph of the absorption spectrum of the compound Fll (A), and the current-voltage curve, a
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / Fll: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • Component in particular a solar cell, with the connection Fll is 6.28%.
  • Fig. 14 is a graph showing the absorption spectrum of Compound F12 (A), and the current-voltage curve, a
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F12: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ is.
  • the fill factor FF is 50.7%
  • the fill factor FF is 50.7%
  • Compound F13 measured on an organic optoelectronic component in the form of an organic solar cell.
  • the current-voltage curve of a BHJ cell with the structure: ITO / C60 (15 nm) / F13: C60 (30nm, 3: 2, 50 ° C) / BPAPF (10nm) / BPAPF: NDP9 (30nm, 10% wt NDP9 ) / NDP9 (lnm) / Al (100 nm) was determined, the photoactive layer having a volume heterojunction (bulk
  • heteroj unction - BHJ heteroj unction - BHJ
  • Components are very suitable and in particular a

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Abstract

L'invention concerne un composé de formule générale I, un composant optoélectronique contenant ce type de composé, et l'utilisation d'un tel composé dans un composant optoélectronique.
EP20760757.3A 2019-07-29 2020-07-24 Composé semiconducteur organique avec un groupe indol, composant optoélectronique organique comprenant ledit composé et utilisation dudit composé Pending EP4008028A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102019120457.7A DE102019120457A1 (de) 2019-07-29 2019-07-29 Organische halbleitende Verbindung mit einer Indolgruppe, organisches optoelektronisches Bauelement mit einer solchen Verbindung, und Verwendung einer solchen Verbindung
PCT/DE2020/100662 WO2021018351A1 (fr) 2019-07-29 2020-07-24 Composé semiconducteur organique avec un groupe indol, composant optoélectronique organique comprenant ledit composé et utilisation dudit composé

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EP (1) EP4008028A1 (fr)
JP (1) JP2022542600A (fr)
KR (1) KR20220041178A (fr)
CN (1) CN114286821A (fr)
AU (1) AU2020321177A1 (fr)
BR (1) BR112022001610A2 (fr)
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CN1774823B (zh) 2003-03-19 2010-09-08 赫里亚泰克有限责任公司 带有有机层的光活性组件
BRPI0909457A2 (pt) 2009-08-03 2015-12-22 Mitsubishi Heavy Ind Ltd gerador de turbina eólica, e, método de montagem do mesmo.
DK2398056T3 (en) 2010-06-21 2016-05-30 Heliatek Gmbh Organic solar cell with multiple transportlagsystemer
EP3187496A1 (fr) * 2015-12-30 2017-07-05 Heliatek GmbH Liaison pour elements de construction electroniques organiques photo-actifs et element de construction electronique organique photo-actif comprenant la liaison
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DE102019120457A1 (de) 2021-02-04
AU2020321177A1 (en) 2022-03-17
KR20220041178A (ko) 2022-03-31
CN114286821A (zh) 2022-04-05
WO2021018351A1 (fr) 2021-02-04
JP2022542600A (ja) 2022-10-05
BR112022001610A2 (pt) 2022-05-24

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