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WO2004025748A1 - Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene - Google Patents

Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene Download PDF

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Publication number
WO2004025748A1
WO2004025748A1 PCT/EP2002/010120 EP0210120W WO2004025748A1 WO 2004025748 A1 WO2004025748 A1 WO 2004025748A1 EP 0210120 W EP0210120 W EP 0210120W WO 2004025748 A1 WO2004025748 A1 WO 2004025748A1
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WO
WIPO (PCT)
Prior art keywords
tris
aminophenyl
photovoltaic device
group
benzene compound
Prior art date
Application number
PCT/EP2002/010120
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English (en)
Inventor
Hieronymus Andriessen
Joop Van Deelen
Martijn Wienk
Jan Kroon
Original Assignee
Agfa-Gevaert
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 Agfa-Gevaert filed Critical Agfa-Gevaert
Priority to JP2004535032A priority Critical patent/JP2005538557A/ja
Priority to AU2002333816A priority patent/AU2002333816A1/en
Priority to EP02807793A priority patent/EP1543570A1/fr
Priority to PCT/EP2002/010120 priority patent/WO2004025748A1/fr
Priority to US10/657,894 priority patent/US20040094197A1/en
Publication of WO2004025748A1 publication Critical patent/WO2004025748A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • 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]
    • H10K2102/102—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising tin oxides, e.g. fluorine-doped SnO2
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • 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
    • H10K85/652—Cyanine dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a photovoltaic device comprising a 1,3,5-tris-aminophenyl-benzene compound optionally in a cationic form.
  • the first type is the regenerative cell which converts light to electrical power leaving no net chemical change behind. Photons of energy exceeding that of the band gap generate electron- hole pairs, which are separated by the electrical field present in the space-charge layer. The negative charge carriers move through the bulk of the semiconductor to the current collector and the external circuit. The positive holes are driven to the surface where they are scavenged by the reduced form of the redox relay molecular (R) , oxidizing it: h + R —» 0, the oxidized form. 0 is reduced back to R by the electrons that re-enter the cell from the external circuit.
  • R redox relay molecular
  • photosynthetic cells operate on a similar principle except that there are two redox systems: one reacting with the holes at the surface of the semiconductor electrode and the second reacting with the electrons entering the counter-electrode.
  • water is typically oxidized to oxygen at the semiconductor photoanode and reduced to hydrogen at the cathode. Titanium dioxide has been the favoured semiconductor for these studies.
  • EP-A 1 176 646 discloses a solid state p-n heterojunction comprising an electron conductor and a hole conductor, characterized in that it further comprises a sensitizing semiconductor, said sensitizing semiconductor being located at an interface between said electron conductor and said hole conductor; and its application in a solid state sensitized photovoltaic cell.
  • thermally stable organic hole-conducting compounds capable of forming stable transparent layers and being compatible with solid state photovoltaic cell configurations .
  • EP 0 349 034 discloses a chemical compound corresponding to. the following general formula:
  • R represents a -NR R group, wherein R and R , same or different, represents a C -C o alkyl groyp including said alkyl groups in substituted form, a benzyl group, a cycloalkyl group, or
  • a photovoltaic device comprising a n-type semiconductor with a band-gap of greater than 2.9 eV and a 1,3,5-tris-aminophenyl-benzene compound represented by formula (I) :
  • R 1 represents a -NR3R4 group, wherein R3 and R4 , same or different, represents a C 2 -C ⁇ o alkyl group including the alkyl groups in substituted form, a benzyl group, a cycloalkyl group, or
  • a process for preparing the above-mentioned photovoltaic device with at least one transparent electrode comprising the steps of: providing a support with a conductive layer as one electrode; coating the conductive layer on the support with a layer comprising the n-type semiconductor with a bandgap of greater than 2.9 eV; coating the n- type semiconductor-containing layer with a solution or dispersion comprising the 1,3,5-tris-aminophenyl-benzene compound, or cation thereof, to provide after drying a layer comprising the 1,3,5-tris- aminophenyl-benzene compound; and applying a conductive layer to the layer comprising the 1,3,5-tris-aminophenyl-benzene compound
  • chalcogenide means a binary compound containing a chalcogen and a more electropositive element or radical.
  • a chalcogen is an element from group IV of the periodic table including oxygen, sulphur, selenium, tellurium and polonium.
  • support means a “self-supporting material” so as to distinguish it from a “layer” which may be coated on a support, but which is itself not self-supporting. It also includes any treatment necessary for, or layer applied to aid, adhesion to the support.
  • continuous layer refers to a layer in a single plane covering the whole area of the support and not necessarily in direct contact with the support.
  • non-continuous layer refers to a layer in a single plane not covering the whole area of the support and not necessarily in direct contact with the support.
  • coating is used as a generic term including all means of applying a layer including all techniques for producing continuous layers, such as curtain coating and doctor-blade coating, and all techniques for producing non-continuous layers such as screen printing, ink jet printing, flexographic printing.
  • PEDOT represents poly (3 , 4-ethylenedioxy- thiophene) .
  • PSS poly (styrenesulphonic acid) or poly (styrenesulphonate) .
  • a photovoltaic device comprising a n-type semiconductor with a band-gap of greater than 2.9 eV and a 1,3,5-tris-aminophenyl-benzene compound represented by formula (I) : wherein R 1 represents a -NR3R4 group, wherein R3 and R4 , same or different, represents a C 2 -C 10 alkyl group including the alkyl groups in substituted form, a benzyl group, a cycloalkyl group, or
  • R represents hydrogen, an alkyl group including a substituted alkyl group or halogen; and the 1,3,5-tris- aminophenyl-benzene compound is optionally in a cationic form.
  • Photovoltaic devices can be of two types: the regenerative type which converts light into electrical power leaving no net chemical change behind in which current-carrying electrons are transported to the anode and the external circuit and the holes are transported to the cathode where they are oxidized by the electrons from the external circuit and the photosynthetic type in which there are two redox systems one reacting with the holes at the surface of the semiconductor electrode and one reacting with the electrons entering the counter- electrode, for example, water is oxidized to oxygen at the semiconductor photoanode and reduced to hydrogen at the cathode.
  • the charge transporting process can be ionic or electronic.
  • Such regenerative photovoltaic devices can have a variety of internal structures in conformity with the end use. Conceivable forms are roughly divided into two types: structures which receive light from both sides and those which receive light from one side.
  • An example of the former is a structure made up of a transparently conductive layer e.g. an ITO-layer or a 'PEDOT/PSS-containing layer and a transparent counter electrode electrically conductive layer e.g. an ITO-layer or a PEDOT/PSS-containing layer having interposed therebetween a photosensitive layer and a charge transporting layer.
  • Such devices preferably have their sides sealed with a polymer or an adhesive to prevent deterioration or volatilization of the inside substances.
  • the external circuit connected to the electrically-conductive substrate and the counter electrode via the respective leads is well-known.
  • the photovoltaic device comprises a single layer system.
  • the photovoltaic device comprises a configuration in which the n-type semiconductor with a band-gap of greater than 2.9.eV is contiguous with the 1,3,5-tris- aminophenyl-benzene compound according to formula (I) or in which a spectral sensitizer is sandwiched between the n-type semiconductor with a band-gap of greater than 2.9 eV and the 1,3,5-tris- aminophenyl-benzene compound according to formula (I) .
  • a photovoltaic device comprising a n-type semiconductor with a band-gap of greater than 2.9 eV and a 1,3,5-tris-aminophenyl- benzene compound represented by formula (I) :
  • R 1 represents a -NR3R4 group wherein R 3 and R4 , same or different, represents a C -C 10 alkyl group including the alkyl groups in substituted form, a benzyl group, a cycloalkyl group, or
  • R represents hydrogen, an alkyl group including a substituted alkyl group or halogen; and the 1,3,5-tris- aminophenyl-benzene compound is optionally in a cationic form.
  • the 1,3,5-tris-aminophenyl- benzene compound represented by formula (I) is selected from the group consisting of:
  • Suitable 1, 3 , 5-Tris-aminophenyl-benzene (TAPB) compounds include:
  • TAPB01 has a glass transition temperature of 107°C.
  • Cations of 1,3,5-tris-aminophenyl-benzene compounds according to formula (I) can be prepared by oxidation of the particular 1,3,5-tris-aminophenyl-benzene compound with an oxidizing agent such as N(p-C6HBr) 3 SbCl 6 .
  • an oxidizing agent such as N(p-C6HBr) 3 SbCl 6 .
  • the n-type semiconductor has a bandgap of less than 6.0 eV.
  • the n-type semiconductor is selected from the group consisting of titanium oxides, tin oxides, niobium oxides, tantalum oxides, tungsten oxides and zinc oxides.
  • the n-type semiconductor may be porous or non-porous, although nonporous n-type semiconductors are preferred.
  • the n-type semiconductor is titanium dioxide.
  • the photovoltaic device further contains at least one spectral sensitizer.
  • the photovoltaic device further contains at least one spectral sensitizer selected from the group consisting of metal chalcogenide nano-particles with a band-gap of less than 2.9 eV and greater than 1.5 eV, organic dyes and metallo- organic dyes .
  • the photovoltaic device further contains at least one spectral sensitizer selected from the group consisting metal oxides, metal sulphides and metal selenides.
  • the photovoltaic device further contains one or more metal sulphides nano-particles with a band-gap of less than 2.9 eV and greater than 1.5 eV.
  • the photovoltaic device further contains one or more metal chalcogenide nano-particles selected from the group consisting of lead sulphide, bismuth sulphide, cadmium sulphide, silver sulphide, antimony sulphide, indium sulphide, copper sulphide, cadmium selenide, copper selenide, indium selenide and cadmium telluride.
  • EP-A 1 176 646, herein incorporated by reference, discloses a solid state p-n heterojunction comprising an electron conductor and a hole conductor, characterized in that it further comprises a sensitizing semiconductor, said sensitizing semiconductor being located at an interface between said electron conductor and said hole conductor; and its application in a solid state sensitized photovolaic cell.
  • the sensitizing semiconductor is in the form of particles adsorbed at the surface of said electron conductor and in a further preferred embodiment the sensitizing semiconductor is in the form of quantum dots, which according to a particularly preferred embodiment are particles consisting of PbS, CdS, Bi S 3 , Sb 2 S 3 , Ag 2 S, InAs, CdTe, CdSe or HgTe or solid solutions of HgTe/CdTe or HgSe/CdSe.
  • Suitable spectrally sensitizing organic dyes (SSOD) include cyanine, erocyanine and anionic dyes, such as:
  • Suitable spectrally sensitizing metallo-organic dyes allowing for broad absorption of the solar spectrum include: chemical name
  • Ruthenium 470 a ruthenium tris (2,2'bipyridyl-4, 4' dicarboxylato) dye from Solaronix ruthenium (II) dichloride
  • Ruthenium 505 a ruthenium cis-bis (isocyanato) (2,2 'bipyridyl-4, 4' dye from Solaronix dicarboxylato) ruthenium (II)
  • Ruthenium 535 previously cis-bis (isothiocyanato)bis (2, 2 '-bipyridyl- known as SRS-HQ, N3 ) , a 4,4' -dicarboxylato) -ruthenium(II) ruthenium dye from Solaronix
  • Ruthenium 620 Black Dye, (anion only) tris (isothiocyanato) - a ruthenium dye from ruthenium(II) -2, 2' :6' , 2 "-terpyridine-4, 4' ,4"- Solaronix tricarboxylic acid
  • aspects of the present invention are realized by a process for preparing a photovoltaic device, according to the present invention, with at least one transparent electrode comprising the steps of: providing a support with a conductive layer as one electrode; coating the conductive layer on the support with a layer comprising the n-type semiconductor with a bandgap of greater than 2.9 eV; coating the n-type semiconductor-containing layer with a solution or dispersion comprising the 1,3,5-tris-aminophenyl- benzene compound, or cation thereof, to provide after drying a layer comprising the 1,3,5-tris-aminophenyl-benzene compound; and applying a conductive layer to the layer comprising the 1,3,5-tris- aminophenyl-benzene compound thereby providing a second electrode.
  • the solution or dispersion of the 1,3,5- tris-aminophenyl-benzene compound according to formula (I) or cation thereof further contains a binder.
  • the solution or dispersion of the 1,3,5- tris-aminophenyl-benzene compound according to formula (I) or cation thereof further contains an electrolyte.
  • Suitable electrolytes include Li [ (CF S0 2 ) 2 N] and lithium trifluoromethanesulphonate (lithium triflate) .
  • the process further comprises the step of applying a solution or dispersion of a spectral sensitizer directly to the n-type semiconductor layer.
  • Supports for use according to the present invention include polymeric films, silicon, ceramics, oxides, glass, polymeric film reinforced glass, glass/plastic laminates, metal/plastic laminates, paper and laminated paper, optionally treated, provided with a subbing layer or other adhesion promoting means to aid adhesion to the layer configuration, according to the present invention.
  • Suitable polymeric films are poly (ethylene terephthalate) , poly(ethylene naphthalate) , polystyrene, polyethersulphone, polycarbonate, polyacrylate, polyamide, polyimides, cellulose triacetate, polyolefins and poly(vinylchloride) , optionally treated by corona discharge or glow discharge or provided with a subbing layer.
  • Layers of nano-porous metal oxide semiconductors with a band- gap of greater than 2.9 eV prepared according the process, according to the present invention, can be used in both regenerative and photosynthetic photovoltaic devices.
  • Photovoltaic devices with solid state organic hole conductor and high temperature sintered nano-porous Ti0 2 are described.
  • Photovoltaic devices 1 to 3 were prepared by the following procedure:
  • a glass plate (2 x 7 cm ) coated with conductive Sn ⁇ 2 :F (Pilkington TEC15/3) with a surface conductivity of ca. 15 Ohm/square was ultrasonically cleaned in isopropanol for 5 minutes and then dried.
  • a small strip of Sn ⁇ 2 :F was removed to prevent short circuit.
  • the glass electrode was partially covered with glass on the long side and a dense non-porous hole blocking titanium dioxide layer applied by spray pyrolysis of an ethanolic solution of di- isopropoxy titanium-bis (acetylacetone) in aerosol form as described by Kavan L. et al. In Electrochim. Acta (1995), 40(5), 643-52, herein incorporated by reference.
  • Triton X-100 Triton X-100.
  • the resulting titanium dioxide colloidal dispersion was cooled in ice and ultrasonically treated for 5 minutes. This dispersion was then doctor-blade coated onto the middle (0.7 x 4.5
  • Nano-sized titanium dioxide dispersion-coated glass electrodes were ' heated at 450°C for 30 minutes then cooled to 150°C on a hot plate at 150 °C for 10 minutes thereby yielding a nano-porous Ti ⁇ 2 layer thickness of 2 ⁇ m. After cooling to 150°C, the nano-porous Ti0 2 layer-coated glass electrode was immediately immersed in a 2 x 10 -4 M solution of the Ruthenium
  • N(p-C 6 H 4 Br) 3 SbCl 6 oxidized the charge transport compound to its cationic salt, Li [ (CF 3 S ⁇ 2 ) 2 N] acting as an electrolyte.
  • Sufficient N(p-C 6 H 4 Br) 3 S Cl 6 was present to ensure that the oxidation process went to completion as determined spectrophotometrically by 40 monitoring, in the case of TABPOl, the 397 nm, 695 nm and 772 nm peaks of the cationic state in analogy to the absorption spectrum reported in 1994 by Bonvoisin et al. in Journal of Physical Chemistry, volume 98, pages 5052-5057. Bonvoisin et al. reported that cyclic voltammetry and coulometry on TABPOl showed a unique, reversible, oxidation wave corresponding to a three-electron process, which was accompanied by the appearance of three bands at
  • TABPOl and TAPB03 appear to be oxidizable to their tri-cations i.e. all three nitrogens in the molecule are oxidizable, whereas in the case of Spiro-OMeTAD only two of the four nitrogens apppear to be oxidizable.
  • the front electrode coated with the charge transport compound was then dried in the dark under Argon at 25°C for 30 minutes 0 followed by drying in a vacuum exicator for a further 30 minutes in dark. Finally a gold electrode was evaporated on top.
  • the photovoltaic device configuration is shown in Figure 1. 0
  • the cell was irradiated with a Steuernagel Solar Constant 575 solar simulator with a metal halide 1 AM light source. The simulator was adjusted to about 1 sunequivalent .
  • the electricity generated was recorded with a Type 2400 SMU Keithley electrometer in the voltage range -1 to +1 volt. 5
  • Table 1 lists the short circuit current (Isc) and open circuit voltage (Voc) for the devices.
  • the acti .ve area was 0.14 cm2.
  • Table 1 Table 1 :
  • Photovoltaic devices 4 to 6 were prepared by the following procedure:
  • Photovoltaic devices 4 to 6 were prepared as described for Photovoltaic devices 1 to 3 , except that nano-titanium dioxide dispersion-coated glass electrode was first dried at 110°C for 5 minutes, then, after cooling to room temperature, a pressure of 500 bars was applied for 5 seconds. This pressure sintered coating was then heated to 150°C, immediately immersed m a 2 x 10 -4 M solution of the Ruthenium 535 bis-TBA dye and then washed and dried as described for Photovoltaic devices 1 to 3.
  • Photovoltaic device 7 was prepared by the following procedure
  • a 2 x 7 cm piece of ITO-coated (from 1ST) with a surface resistivity of 70 Ohm/square was cleaned by rinsing in ethanol and ozone treatment.
  • the electrode was partially covered with adhesive tape and put in an electron-beam apparatus. It was placed overnight in a vacuum with continuous pumping and the non-porous Ti ⁇ 2 was applied locally to the substrate. After the deposition, the vacuum was released and the sample was ready to use. 5 g of DEGUSSA P25 titanium dioxide nano-particles was added to
  • the coated PET electrode with the nano titanium dioxide dispersion was first dried at 110°C for 5 minutes, then, after cooling to room temperature, a pressure of 500 bars was applied for
  • Table 2 lists the results for the different hole transporting materials with pressure sintered Ti ⁇ 2 on a glass electrode and on an ITO-PET electrode.
  • Photovoltaic devices 5 and 6 with 1,3,5-tris-aminophenyl-benzene compounds TAPB01 and TAPB03 in a tri-cationic form and pressure sintered titanium dioxide exhibit photovoltaic effects, which are much closer to the performance of the reference photovoltaic device with Spiro-OMeTAD than for photovoltaic devices with heat sintered titanium dioxide.
  • the present invention may include any feature or combination of features disclosed herein either implicitly or explicitly or any generalisation thereof irrespective of whether it relates to the presently claimed invention.

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Abstract

L'invention concerne un dispositif photovoltaïque comprenant un semi-conducteur de type n d'une largeur de bande interdite supérieure à 2,9 eV, un sensibilisateur spectral et un composé 1,3,5-tris-aminophényl-benzène représenté par la formule (I), dans laquelle R1 représente un groupe -NR3R4, où R3 et R4, égaux ou différents, représentent un groupe alkyle C2-C10 notamment les groupes alkyle sous forme substituée, un groupe benzyle, un groupe cycloalkyle, ou un groupe aryle, et R2 représente hydrogène, un groupe alkyle notamment un groupe alkyle substitué ou halogène. Le composé 1,3,5-tris-aminophényl-benzène est éventuellement en forme cationique. L'invention concerne également un procédé de préparation du dispositif photovoltaïque susmentionné comprenant au moins une électrode transparente. Ce procédé consiste: à obtenir un support comportant une couche conductrice telles qu'une électrode; à revêtir cette couche conductrice située sur le support avec une couche comprenant le semiconducteur de type n ayant une largeur de bande interdite supérieure à 2,9 eV ; à revêtir la couche contenant un semiconducteur de type n avec une solution ou une dispersion comprenant le composé 1,3,5-tris-aminophényl-benzène, ou un cation de ce composé, afin d'obtenir après séchage une couche comprenant le composé 1,3,5-tris-aminophényl-benzène; et à appliquer une couche conductrice à la couche comprenant le composé 1,3,5-tris-aminophényl-benzène de manière à obtenir une seconde électrode.
PCT/EP2002/010120 2002-09-10 2002-09-10 Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene WO2004025748A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2004535032A JP2005538557A (ja) 2002-09-10 2002-09-10 １，３，５−トリス−アミノフェニル−ベンゼン化合物を含んでなる光電池装置
AU2002333816A AU2002333816A1 (en) 2002-09-10 2002-09-10 Photovoltaic device comprising a 1,3,5-tris-aminophenyl-benzene compound
EP02807793A EP1543570A1 (fr) 2002-09-10 2002-09-10 Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene
PCT/EP2002/010120 WO2004025748A1 (fr) 2002-09-10 2002-09-10 Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene
US10/657,894 US20040094197A1 (en) 2002-09-10 2003-09-09 Photovoltaic device comprising a 1,3,5-tris-aminophenyl-benzene compound

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PCT/EP2002/010120 WO2004025748A1 (fr) 2002-09-10 2002-09-10 Dispositif photovoltaique comprenant un compose 1,3,5-tris-aminophenyl-benzene

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EP1837929A1 (fr) * 2006-03-23 2007-09-26 Ecole Polytechnique Fédérale de Lausanne (EPFL) Matériau de transport de charge liquide
EP1979915A2 (fr) * 2005-12-28 2008-10-15 E.I. Du Pont De Nemours And Company Compositions comprenant de nouveaux composes et dispositifs electroniques produits au moyen de ces compositions
US8440324B2 (en) 2005-12-27 2013-05-14 E I Du Pont De Nemours And Company Compositions comprising novel copolymers and electronic devices made with such compositions
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
US8648333B2 (en) 2009-10-19 2014-02-11 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US8937300B2 (en) 2009-10-19 2015-01-20 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
CN114292643A (zh) * 2021-12-31 2022-04-08 湖南智享未来生物科技有限公司 一种苯三胺碳点、制备方法以及在细胞核染色中的应用

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EP1979915A2 (fr) * 2005-12-28 2008-10-15 E.I. Du Pont De Nemours And Company Compositions comprenant de nouveaux composes et dispositifs electroniques produits au moyen de ces compositions
EP1979915A4 (fr) * 2005-12-28 2009-08-05 Du Pont Compositions comprenant de nouveaux composes et dispositifs electroniques produits au moyen de ces compositions
EP2412699A1 (fr) * 2005-12-28 2012-02-01 E.I. Du Pont De Nemours And Company Compositions comportant des nouveaux composés et des dispositifs électroniques fabriqués avec ces composés
EP1837929A1 (fr) * 2006-03-23 2007-09-26 Ecole Polytechnique Fédérale de Lausanne (EPFL) Matériau de transport de charge liquide
WO2007107961A1 (fr) * 2006-03-23 2007-09-27 Ecole Polytechnique Federale De Lausanne (Epfl) Matière de transport de charges liquide
JP2009530791A (ja) * 2006-03-23 2009-08-27 エコール ポリテクニーク フェデラル ドゥ ローザンヌ（エーペーエフエル） 液体電荷輸送材料
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US8648333B2 (en) 2009-10-19 2014-02-11 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US8937300B2 (en) 2009-10-19 2015-01-20 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
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