WO2017085078A1 - Composant électronique organique, utilisation d'un dopant p pour un matériau matriciel - Google Patents

Composant électronique organique, utilisation d'un dopant p pour un matériau matriciel Download PDF

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Publication number
WO2017085078A1
WO2017085078A1 PCT/EP2016/077767 EP2016077767W WO2017085078A1 WO 2017085078 A1 WO2017085078 A1 WO 2017085078A1 EP 2016077767 W EP2016077767 W EP 2016077767W WO 2017085078 A1 WO2017085078 A1 WO 2017085078A1
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radicals
matrix material
organic
radical
component according
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Florian Kessler
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Osram Oled Gmbh
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/30—Doping active layers, e.g. electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K10/486—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising two or more active layers, e.g. forming pn 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
    • H10K30/40—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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 electronic device using a p-type dopant for a matrix material
  • the disclosure is hereby incorporated by reference. It is an organic electronic device and a use of a p-type dopant for a matrix material specified.
  • organic electronic components such as organic electronic components
  • organic transistors organic transistors
  • organic light-emitters organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-emitters, organic light-
  • organic matrix materials used are often doped with additional compounds that improve charge transport.
  • hole transport layers are often mixed with metals or metal complexes as so-called p-dopants.
  • p-dopants Especially in organic light-emitting diodes, the luminescence, the efficiency and the
  • Electrode-hole pair density in the light-emitting layer, so that efficient electron and hole transport of the electrodes are needed in the light-emitting layer.
  • At least one object of certain embodiments is to provide an efficient organic electronic device. Another object is to provide a use of an efficient p-type dopant for a matrix material.
  • the device comprises a matrix material and a p-type dopant.
  • p-type dopant includes or means in particular materials which, with regard to the matrix material, have a Lewis acidity
  • the p-type dopant is an organic phosphine.
  • An organic phosphine is a compound having a central phosphorus atom with a lone pair of electrons to which three organic radicals are attached. Phosphorus is one of the non - metals, so phosphines are not included in the definition of
  • organic phosphines show a p-doping effect, so that the hole transport of a
  • Matrix material that is doped with an organic phosphine can be significantly increased in the operation of an organic electronic device.
  • the organic phosphine is substituted with at least one halogen atom.
  • the halogen atom is selected from the group consisting of: F, Cl and Br.
  • the halogen atom is F or Cl, more preferably F.
  • Halogens such as fluorine, possess due to their high
  • Electronegativity a strong electron-withdrawing effect. This is important for the adaptation of the electronic properties of organic phosphine.
  • the electron-withdrawing groups allow for an enhancement of the Lewis acidity of the organic phosphine and thus its action as a p-type dopant.
  • organic phosphines in particular organic phosphines, which are substituted with F, Cl or Br, as p-type dopants, would be rather assume that the phosphines due to the lone pair of electrons on the phosphorus
  • the p-type dopant acts
  • Matrix material creates a positive charge or a positive partial charge. It is also possible that forms by the proximity of the phosphine and the matrix material, a charge-transfer complex. By the reduced
  • Electron density in the matrix material and the thus increased number of positive charge carriers (holes) will increase its ability to drive holes in the device
  • the phosphane has the following
  • R 1 , R 2 and X are independently selected from a group of radicals comprising CN, aryl, heteroaryl,
  • the radicals R 1 , R 2 and X are bonded via a carbon atom to the phosphorus atom. These are in particular covalent bonds.
  • At least one of R 1 , R 2 or X is substituted with at least one halogen atom.
  • the halogen atom is selected from the group consisting of: F, Cl and Br.
  • the halogen atom is F or Cl, more preferably F.
  • the doping effect of the organic phosphine can be significantly increased, which leads to an improvement in the hole conductivity of the matrix material.
  • the organic phosphine has a lone pair of electrons and thus a sterically poorly screened side of the molecule. Thus it is possible that the phosphine with the little
  • Electron transport it is possible in particular in organic light-emitting diodes, the number itself forming excitons needed for the emission of light in the light-emitting layer. So are the luminescence, the efficiency and also the
  • R 1 , R 2 and X are independently
  • aryl selected from the group consisting of aryl, heteroaryl, alkyl, heteroalkyl, cycloalkyl,
  • Alkyl radical linear and branched C 1 -C 20 -alkyl radicals.
  • Alkyl radicals may be substituted or unsubstituted.
  • alkyl radicals with F, Cl and / or Br may be monosubstituted or polysubstituted.
  • the alkyl radical may be substituted by a heteroaryl radical and then be an alkylheteroaryl radical:
  • Heteroaryl may be selected from those defined below
  • Heteroaryl be selected.
  • Alkenyl C2-C10 alkenyl radicals, which may be branched or linear.
  • the alkenyl radicals may be substituted or unsubstituted.
  • the alkenyl radicals may be mono- or polysubstituted with F, Cl and / or Br.
  • Alkynyl radical C 2 -C 10 -alkynyl radicals, which may be branched or linear.
  • the alkynyl radicals may be substituted or unsubstituted.
  • the alkynyl radical may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Cycloalkyl radical C3-C25-cycloalkyl radicals.
  • the cycloalkyl radicals may be substituted or unsubstituted.
  • the cycloalkyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Aryl radical selected from phenyl and naphthyl radical.
  • Aryl radicals may be substituted or unsubstituted.
  • aryl radicals may be mono- or polysubstituted with F, Cl and / or Br.
  • Heteroaryl radical selected from the group comprising:
  • Heteroaryl radicals may be substituted or unsubstituted.
  • the heteroaryl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Heterocycloalkyl radicals selected from the group comprising: piperidine, 1,4-piperazine, pyrrolidine, morpholine,
  • heterocycloalkyl radicals may be substituted or unsubstituted.
  • the heterocycloalkyl radicals may be mono- or polysubstituted with F, Cl and / or Br.
  • the Etherrest can be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Der Thioether may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the ester radical may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • N- (R ') 2 is a cyclic amine.
  • N- (R ') 2 is a cyclic amine
  • the amide residue can be replaced with F, Cl and / or Br may be monosubstituted or polysubstituted.
  • Acrylic radical may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Ketorest: - (CH 2 ) i C (O) - (CH 2 ) i CH 3 , where 1 "' 0, 1, 2,
  • Ketorest can be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the aryl radical can be selected from the above-defined aryl radicals
  • the aryl radical may be selected from the aryl radicals defined above.
  • Heteroalkylaryl may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Cycloalkenyl radical C3-C10-cycloalkenyl radicals.
  • Cycloalkenyl radicals may be substituted or unsubstituted.
  • the cycloalkenyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Heterocycloalkenyl radical non-aromatic, heterocyclic or heteroatom-substituted carbocyclic alkenyl radical.
  • Alkyl radical linear and branched C 1 -C 5 -alkyl radicals.
  • Alkyl radicals may be substituted or unsubstituted.
  • the alkyl radicals may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • alkyl radical may be substituted by a heteroaryl radical and then be an alkylheteroaryl radical:
  • the heteroaryl radical may be selected from the preferred heteroaryl radicals defined above.
  • Alkenyl allyl, vinyl and butenyl. The allyl vinyl and butenyl radicals may be substituted or
  • allyl, vinyl and butenyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Alkynyl ethynyl, propynyl, butynyl.
  • the ethynyl, propynyl, butinyl radicals may be substituted or
  • alkynyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the alkynyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the alkynyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the alkynyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Cycloalkyl radical C3-C6-cycloalkyl radicals.
  • the cycloalkyl radicals may be substituted or unsubstituted.
  • the cycloalkyl radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Aryl radical phenyl radical.
  • the phenyl radical may be substituted or unsubstituted.
  • the phenyl radical may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Heteroaryl radical selected from the group comprising:
  • Pyridine and pyrimidine residues Pyridine and pyrimidine residues. Pyridine and pyrimidine residues electron-withdrawing radicals, which is why a very good p-doping effect is observed.
  • Pyrimidine residues may be substituted or unsubstituted.
  • the pyridine and pyrimidine radicals may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Heterocycloalkyl radicals selected from the group comprising: piperidine and pyrrolidine radical.
  • the piperidine and pyrrolidine radical selected from the group comprising: piperidine and pyrrolidine radical.
  • Pyrrolidine radicals may be substituted or unsubstituted.
  • the piperidine and pyrrolidine radicals may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the ether residue can be replaced by F, Cl and / or Br may be monosubstituted or polysubstituted.
  • the thioether radical can be substituted by F, Cl and / or Br may be monosubstituted or polysubstituted.
  • the ester radical can be monosubstituted or with F, Cl and / or Br
  • the amide radical may be monosubstituted or polysubstituted with F, Cl and / or Br.
  • the acrylic radical may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Ketorest: - (CH 2 ) i C (O) - (CH 2 ) i CH 3 , where 1 "' 0 and
  • Ketorest can be monosubstituted or polysubstituted with F, Cl and / or Br.
  • Aryl may be selected from the preferred aryl radicals defined above.
  • the alkylaryl radical may be monosubstituted or polysubstituted by F, Cl and / or Br. For example, it is -CH 2 -C 6 F 5 .
  • the aryl radical may be selected from the preferred aryl radicals defined above.
  • the heteroalkylaryl radical may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Cycloalkenyl radical C5-C8-cycloalkenyl radicals.
  • Cycloalkenyl radical can be monosubstituted or polysubstituted by F, Cl and / or Br. For example, it is cyclooctadiene.
  • Heterocycloalkenyl radical cyclic, non-aromatic amine having a double bond.
  • the cycloalkenyl radical may be monosubstituted or polysubstituted by F, Cl and / or Br.
  • Alkyl radical methyl, ethyl, propyl, butyl radicals. These radicals may be substituted or unsubstituted. Especially the radicals can be monosubstituted or polysubstituted by F.
  • Alkenyl radical allyl and vinyl radicals. The remains can
  • Alkynyl ethynyl.
  • the ethynyl radical may be substituted or unsubstituted.
  • the ethynyl radical is monosubstituted or polysubstituted by F.
  • Cycloalkyl radical cyclohexyl radical.
  • the cyclohexyl radical may be substituted or unsubstituted.
  • the cyclohexyl radical is monosubstituted or polysubstituted by F.
  • Aryl radical phenyl radical.
  • the phenyl radical may be substituted or unsubstituted.
  • the phenyl radical is monosubstituted or polysubstituted by F.
  • Heteroaryl radical selected from the group comprising:
  • the pyridine radical can be substituted or
  • pyridine radical is monosubstituted or polysubstituted by F.
  • heterocycloalkyl radicals piperidine radical.
  • the piperidine residue may be substituted or unsubstituted.
  • the piperidine radical is monosubstituted or polysubstituted by F.
  • the ether radical is in particular mono- or polysubstituted by F.
  • the thioether radical is in particular mono- or polysubstituted by F.
  • Ester residue is in particular monosubstituted or polysubstituted by F.
  • the acrylic radical is in particular monosubstituted or polysubstituted by F.
  • Ketorest: - (CH 2 ) i C (O) - (CH 2 ) i CH 3 , where 1 "' 0 and
  • keto radical is in particular monosubstituted or substituted by one or more times.
  • Aryl may be selected from the above-defined particularly preferred aryl radicals. For example, it is -CH 2 -CeF 5 .
  • the aryl radical can be the above
  • heteroalkylaryl radical is: -CH 2 OC 6 F 5 .
  • Cycloalkenyl radical C6-C8-cycloalkenyl radicals.
  • Cycloalkenyl radical is in particular monosubstituted or polysubstituted by F.
  • Heterocycloalkenyl radical cyclic, non-aromatic amine having a double bond.
  • the cycloalkenyl radical is in particular monosubstituted or polysubstituted by F.
  • R 1 , R 2 are independently selected from a group of radicals which are aryl,
  • Heterocycloalkylreste comprises. Preference is given to R 1 , R 2
  • radicals R 1, R 2 may independently have the following formula:
  • A independently of one another are H, D, F, Cl and / or Br, preferably H and / or F. is the bond to the phosphorus atom of the phosphine.
  • R 1 , R 2 this results in one of the following radicals for R 1 , R 2 :
  • At least one of the radicals R or R 2 is at least one halogen atom, preferably with at least one chlorine or fluorine atom, more preferably substituted with a fluorine atom.
  • X is selected from a group of radicals comprising aryl, heteroaryl, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, and alkynyl radicals.
  • n 1.
  • X is preferably an aryl radical.
  • X can have the following formula:
  • A independently of one another are H, D, F, Cl and / or Br, preferably H and / or F. is the bond to the phosphorus atom of the phosphine. For example, this results in one of the following radicals:
  • n 1 and the phosphine has the following formula I i
  • n 2.
  • X is preferably selected from a group of radicals comprising aryl, alkyl, alkenyl, and alkynyl radicals.
  • X may have one of the following formulas
  • T independently of one another are H, D, F, Cl and / or Br, preferably H and / or F.
  • A is independently H, D, CN, F, Cl and / or Br, preferably H, CN and / or F.
  • ⁇ ⁇ is 1, 2, 3, 4, or 5. is the bond to one the two phosphorus atoms of the phosphine. For example, this gives one of the following radicals for X:
  • n 2 and the phosphane has one of the following formulas:
  • n 3.
  • X is preferably an alkyl radical.
  • X CH.
  • n 3 and the phosphane has the following formula I3
  • the phosphines described are easy to prepare and require no complicated manufacturing processes and are partially commercially available, so that only one
  • the organic phosphines are available via Grignard reactions.
  • the starting materials are the commercially available compounds pentafluorophenylmagnesium bromide and
  • bromopentafluorobenzene is lithiated with n-butyllithium by halogen-metal exchange and subsequently with the corresponding chlorodiphosphane
  • This synthesis route is also on use partially fluorinated or other halogen substituted aromatic Grignard reagents.
  • the matrix material may interact with the phosphane as follows:
  • NPB N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) benzidine
  • n 1
  • phosphine coordinates to the nitrogen of the matrix material and thereby at least partially absorbs electrons from the matrix material. This results in the nitrogen of the
  • Matrix material a positive partial charge when a covalent bond is formed between the nitrogen and the phosphor. If the nitrogen coordinates to the phosphorus, at least one positive partial charge is formed on the nitrogen. The electron density becomes stronger on the phosphane
  • Electron acceptor acts. This causes a lower
  • Conductance paths for example, through chemical bonds between several molecules of the matrix material, can be helpful for hole transport, but is due to the
  • the doping effect may be explained based on the HOMO and LUMO layers of the matrix material and the p-type dopant.
  • the highest unoccupied molecular orbital (LUMO) of the phosphane should be as low in energy (against vacuum level) as possible, ie as stable as possible, but at least close to the highest
  • HOMO occupied molecular orbital
  • Transfer of electrons of the HOMO of the matrix material into the LUMO of the phosphane can take place completely or partially, in particular if the LUMO of the phosphine is lower in energy than the HOMO of the
  • this doping mechanism may be present, for example, if the matrix material is not an amine
  • the doping effect takes place via the HOMO and LUMO layers as well as via the "hopping" mechanism.
  • the phosphine is a triarylphosphane and the matrix material is a Triarylamine. Due to the structural
  • Similarity of the p-type dopant and the matrix material enables a particularly efficient doping effect.
  • Both the p-dopant and the matrix material have a free electron pair and thus a sterically little screened molecular side.
  • the phosphine with the less screened molecular side coordinates to the less screened side of the nitrogen of the matrix material, thereby subtracting electron density from the matrix material by the phosphane.
  • both the p-type dopant and the matrix material are common, preferably from different sources in the
  • the p-type dopant and the matrix material are dissolved in a solvent and deposited by means of printing techniques, spin coating, knife coating, slot coating and the like.
  • the finished layer is through
  • PEDOT poly (3, 4-
  • matrix materials which are referred to as "small molecules” can be processed with particular preference by means of a solvent process.
  • spiro-TAD (2, 2 ', 7, 7' tetrakis (N, N-diphenylamino) -9,9'-spirobifluorene) and spiro-TTB (2,2 ', 7,7'-tetrakis) ( ⁇ , ⁇ '-di-p-methylphenylamino) -9, 9'-spirobifluorene and other materials, as listed in this application as matrix materials.
  • the matrix material of the organic electronic component comprises one or more of the following materials, for example, in one
  • Hole transporting layer can be used:
  • NPB N, '-Bis (naphthalen-1-yl) -N,' -bis (phenyl) -benzidine
  • ⁇ -NPB N, '-Bis (naphthalen-2-yl) -N,' -bis ( phenyl) benzidine
  • TPD N, '- bis (3-methylphenyl) -N,' - bis (phenyl) benzidine
  • spiro-TPD N, '- bis (3-methylphenyl) -N,' - bis (phenyl) benzidine
  • DMFL-NPB ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9,9-dimethyl-fluorene
  • DPFL-NPB ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9, 9-diphenyl-fluorene
  • Spiro-TAD (2, 2 ', 7, 7' tetrakis (N, N-diphenylamino) -9,9'-spirobifluorene)
  • PAPB N '-bis (phenanthrene-9-yl) -N,' -bis (phenyl) -benzidine
  • NHT51, EL-301, EL-22T are particularly well suited. But also comparable commercially available materials can be used. These materials have proven to be matrix materials in
  • the matrix material and the p-type dopant form a hole-transporting layer in the
  • hole-transporting layer may comprise or consist of the p-type dopant and the matrix material. During operation of the device, only a very small voltage drop is observed across the hole transporting layer, which contributes to an increase in the efficiency of the device.
  • Layer has a layer thickness between 1 nm and 1000 nm
  • nm preferably between 30 nm and 300 nm, for example 200 nm.
  • the doping level is in
  • volume percent of the p-type dopant based on the volume of the matrix material between 1% and 50%. This has proven to be useful, especially for a hole transporting
  • the degree of doping is between 5% and 30%, more preferably between 10% and 20%, for example 15%.
  • the degree of doping can be adapted to the charge transport required for the component. In the case of devices, especially organic light emitting diodes, balanced charge transport is important, that is, there must be a balance between electrons and holes. For generating light in one
  • light-emitting diode is, for example, an exciton formed by a hole and an electron, necessary for the emission of light, so that as many as possible
  • Electrons and holes should be present in the light-emitting layer to obtain an efficient device. Also, the lifetime of the device can be improved by a good charge balance, since excess
  • Charge carriers e.g., holes
  • Oxidation for degradation, for example, by oxidation, which may result in materials.
  • the device comprises a
  • the hole injecting layer may include the p-type impurity or the p-type impurity and the
  • matrix material As matrix materials, the matrix materials mentioned can be used for a hole-transporting and electron-blocking layer.
  • the degree of doping in volume percent of the p-type dopant based on the volume of the matrix material is between 70% and 100%.
  • the hole-injecting layer consists of the p-type dopant.
  • the organic electronic component is selected from a group that includes organic
  • Solar cells and organic photodetectors includes.
  • the organic transistor is a field-effect transistor or a
  • Bipolar transistors are bipolar transistors
  • the organic electronic device is an organic light emitting diode. In one embodiment, the organic comprises
  • the matrix material and the p-type dopant form an electron-blocking layer in the organic electronic device.
  • Electron-blocking layer may comprise or consist of the p-type dopant and the matrix material.
  • the matrix material is one
  • electron-blocking layer at least partially
  • Typical matrix materials of an electron-blocking layer are:
  • the organic electronic device comprises a cathode, an anode and a
  • hole-transporting layer comprising or consisting of the matrix material and the p-type dopant.
  • the hole transporting layer is disposed between the anode and the cathode.
  • the organic electronic device comprises a light-emitting layer.
  • the light-emitting layer is configured to generate light in an operating state of an organic light-emitting diode.
  • Suitable materials for the light-emitting layer are materials that emit radiation due to
  • fluorescence or phosphorescence for example, polyfluorene, polythiophene or polyphenylene or derivatives, compounds, mixtures or copolymers thereof.
  • phosphorescent materials are, for example, iridium and platinum complexes.
  • the organic light emitting diode may also have a plurality of light emitting
  • the organic electronic device comprises a cathode, an anode, and a hole injecting layer comprising the matrix material and the p-type dopant or comprises the p-type dopant or these materials
  • the hole injecting layer is disposed between the anode and the cathode.
  • the hole-injecting layer has a direct mechanical and / or electrical contact with the anode.
  • the hole-injecting layer is between the light-emitting layer and the anode
  • the organic electronic device comprises a cathode, an anode and a
  • Electron-blocking layer comprising the matrix material and the p-type dopant or from these materials
  • the electron-blocking layer has a direct mechanical and / or electrical contact with the light-emitting layer.
  • the device comprises an anode, a hole transporting layer, and a hole injecting one Layer.
  • the hole-injecting layer is disposed between the hole-transporting layer and the anode.
  • the hole transporting layer comprises or consists of the matrix material and the p-type dopant and / or the
  • hole-injecting layer comprises or consists of the p-type dopant or the matrix material and the p-type dopant.
  • the hole-injecting layer comprises or consists of the p-type dopant or the matrix material and the p-type dopant.
  • the device comprises an anode, a hole transporting layer, a hole injecting layer and an electron blocking layer.
  • hole injecting layer is between the
  • the hole transporting layer comprises or consists of the matrix material and the p-type dopant and / or the
  • Electron-blocking layer comprises or consists of the matrix material and the p-type dopant and / or the
  • hole-injecting layer comprises or consists of the p-type dopant or the matrix material and the p-type dopant.
  • the hole-injecting layer comprises or consists of the p-type dopant or the matrix material and the p-type dopant.
  • hole-injecting layer between the hole-injecting layer and the hole-transporting layer, and between the hole-transporting layer and the hole-injecting layer
  • a light-emitting layer is present, it is preferably in direct
  • the organic light-emitting diode may include layers of organic polymers, organic oligomers, organic monomers, organic small non-polymeric molecules ("small molecules") or combinations thereof.
  • the organic light-emitting diode may, for example, in addition to the layers mentioned electron-injecting layers, electron-transporting layers and / or
  • the organic light-emitting diode has a substrate on which the anode and the cathode are applied.
  • the substrate can be any suitable substrate on which the anode and the cathode are applied.
  • one or more materials in the form of a layer, a plate, a film or a laminate which are selected from glass, quartz, plastic, metal, silicon wafer.
  • the anode is disposed above the substrate and is preferably in direct alignment therewith
  • An encapsulation arrangement can be arranged above the anode and the cathode, preferably above the cathode, which protects the electrodes and the further layers from harmful external influences such as moisture, oxygen,
  • Hydrogen sulfide or other substances can protect.
  • the encapsulation arrangement is in direct
  • WO 2010/066245 AI in particular with regard to the structure, the layer composition and the materials of the substrate, the anode and the cathode and the
  • FIG. 1 shows a schematic side view of a
  • Figure 2 shows a schematic side view of a
  • FIGS. 3A to 3F show schematic side views of FIG.
  • FIG. 4 shows the current-voltage characteristic of a
  • identical, identical or identically acting elements can each be provided with the same reference numerals.
  • the illustrated Elements and their proportions with each other are not to be regarded as true to scale, but individual elements, such as layers, components, components and areas, for better presentation and / or better understanding may be exaggerated.
  • FIG. 1 shows an exemplary embodiment of an organic light-emitting diode 10.
  • Light emitting diode 10 comprises a substrate 1,
  • anode 2 formed of indium tin oxide, a transparent conductive oxide (TCO). Above the anode are a hole injecting layer 3, a hole transporting layer 4 and a
  • the light-emitting layer 5 is arranged.
  • hole transporting layer 4 consists of a
  • the p-type dopant is present at 15% by volume based on the volume of the matrix material.
  • the hole-transporting layer 4 has a layer thickness of 200 nm.
  • Above the light-emitting layer 5 is a hole-blocking
  • the light emitting layer 5 may include an electron and / or hole transporting material and one or more phosphorescent or fluorescent emitters.
  • Materials for the electron-transporting layer 7, the electron-injecting layer 8, and the hole-injecting layer 3 are known to those skilled in the art.
  • the electron-transporting layer 7 is formed from 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1, 3, 4-oxadiazole with an n-dopant NDN-1 or Ca, which
  • Electronically injecting layer 8 is formed from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP) and the
  • an electron-blocking layer may be arranged (not shown here).
  • Materials for the electron-blocking layer are known to those skilled in the art.
  • bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum can be used.
  • the electron-blocking layer can also be composed of the matrix material HTM-014 and the p-type dopant 1,2-
  • Bis (bis (pentafluorophenyl) phosphino) ethane be formed.
  • the hole-injecting layer 3 may be formed of the matrix material HTM-014 and the p-type dopant 1,2-bis (bis (pentafluorophenyl) phosphino) ethane.
  • the p-type dopant is present in this layer at 85 percent by volume based on the volume of the matrix material.
  • Figure 2 is an embodiment of an organic compound
  • the solar cell 20 comprises or consists of an anode of indium tin oxide 22,
  • the hole-transporting layer 23 consists of a matrix material NPB (N, N'-bis (naphthalen-1-yl) -N, '-bis ( phenyl) benzidine) and the p-type dopant P (CeF 5 ) 3 and has a layer thickness of 150 nm.
  • the p-type dopant is 15% by volume based on the volume of the
  • the absorption layer 24 In the absorption layer 24, light is absorbed from the environment. By absorbing the light, a molecule of the absorption layer 24 is in the excited state and it comes to a
  • Hole transporting layer 23 with the organic phosphine according to the invention as p-dopant has a positive effect on the charge extraction and thus on the efficiency of organic solar cells.
  • FIGS. 3A to 3F Exemplary embodiments of organic field-effect transistors 30 are shown in FIGS. 3A to 3F.
  • a gate electrode 32, a gate dielectric 33, a source and drain contact (34 and 35), and an organic semiconductor layer 36 are deposited.
  • hatched areas 37 show the hole-transporting layer and thus the locations where the matrix material of the organic semiconductor layer 36 is doped with the p-type dopant.
  • the matrix material is DPFL-NPB ( ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9, 9-diphenyl-fluorene) and the p-dopant P (C 6 F 5 ) 2 (C 6 H 5 ).
  • the current-voltage characteristic for the matrix material is DPFL-NPB ( ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9, 9-diphenyl-fluorene) and the p-dopant P (C 6 F 5 ) 2 (C 6 H 5 ).
  • the current-voltage characteristic for the matrix material is DPFL-NPB ( ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇
  • the undoped matrix material HTM014, Merck KGaA (reference I) and for the doped with the p-type dopant 1,2-bis (bis (pentafluorophenyl) phosphino) ethane doped HTM014 (reference II).
  • the voltage in volts is plotted on the x-axis and the current density in milliamps per cm 2 on the y-axis.
  • the measurements are based on the following components:
  • the component according to the invention consists of a glass substrate and arranged above it an anode made of ITO. Above the anode is the hole transporting layer
  • hole transporting layer is 85% by volume.
  • the hole transporting layer has a layer thickness of 200 nm.
  • Above the hole transporting layer is a
  • the reference component is constructed like the device according to the invention, with the
  • 1, 2-bis (bis (pentafluorophenyl) phosphino) ethane is commercially available from Sigma-Aldrich. Before the p-type impurity was used, it was purified as follows. There were 888 mg of the solid is weighed and dried in vacuo at a pressure of about 5 ⁇ 10 "6 mbar and at a temperature of 143 ° to 145 ° C sublimated. The weight of the solid obtained was 814 mg. The 814 mg of the solid obtained were again sublimed in vacuo at a pressure of about 5 ⁇ 10 "6 mbar and a temperature of 143 to 145 ° C. The product

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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composant électronique organique. Ce composant comprend un matériau matriciel qui contient un phosphane organique comme dopant p. Ce phosphane organique est substitué avec au moins un atome d'halogène.
PCT/EP2016/077767 2015-11-16 2016-11-15 Composant électronique organique, utilisation d'un dopant p pour un matériau matriciel WO2017085078A1 (fr)

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