[go: up one dir, main page]

WO2004030029A2 - Guidage de dispositifs polymeres pour interconvertir de la lumiere et de l'electricite - Google Patents

Guidage de dispositifs polymeres pour interconvertir de la lumiere et de l'electricite Download PDF

Info

Publication number
WO2004030029A2
WO2004030029A2 PCT/EP2003/010258 EP0310258W WO2004030029A2 WO 2004030029 A2 WO2004030029 A2 WO 2004030029A2 EP 0310258 W EP0310258 W EP 0310258W WO 2004030029 A2 WO2004030029 A2 WO 2004030029A2
Authority
WO
WIPO (PCT)
Prior art keywords
electrode
polymer
cell
poly
type
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.)
Ceased
Application number
PCT/EP2003/010258
Other languages
English (en)
Other versions
WO2004030029A3 (fr
Inventor
Frederik C. Krebs
Mikkel JØRGENSEN
Kristoffer Almdal
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.)
Riso National Laboratory
Original Assignee
Riso National Laboratory
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 Riso National Laboratory filed Critical Riso National Laboratory
Priority to AU2003282015A priority Critical patent/AU2003282015A1/en
Publication of WO2004030029A2 publication Critical patent/WO2004030029A2/fr
Publication of WO2004030029A3 publication Critical patent/WO2004030029A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/701—Organic molecular electronic devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • 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
    • 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
    • H10K85/701—Langmuir Blodgett films
    • 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 devices for inter- converting light and electricity, including both photovoltaic cells and electroluminescent cells, based on conducting polymers .
  • Yoshino et al, IEEE Trans. Electron Devices 1997, 44, 1315-1324 describes devices based on the effect of light on conjugated polymers such as poly (p-phenylene vinylene) (PPV) and its derivatives.
  • PV poly (p-phenylene vinylene)
  • Devices of this kind operate generally as follows. In an electroluminescent device, electrons and holes injected at opposed electrodes reach one another by conduction through conductive organic molecules and recombine to produce light. In photovoltaic devices, photons are absorbed and the energy of the photon forms an exiton consisting of an electron and a hole which initially are bound together. These can be separated and caused to migrate towards electrodes by an electric field, suitably produced by electrodes of differing work functions.
  • Yoshino et al proposed the use of a donor polymer D (a p-type semiconducting polymer in which conduction of holes occurs) and an acceptor material A, specifically C 6 o fullerene molecules. These are good electron acceptors. They further proposed the use of a middle layer M of a material which is a light absorbing material such as octaethylporphine (OEP) . Thin films of OEP and C 6 o were deposited onto a D polymer film by organic molecular beam deposition. The photocurrent intensity of the D-M-A photocell is enhanced by over 100 times with respect to a cell with only the M layer and about twice that of a similar D-A cell.
  • D a p-type semiconducting polymer in which conduction of holes occurs
  • acceptor material A specifically C 6 o fullerene molecules. These are good electron acceptors.
  • a middle layer M of a material which is a light absorbing material such as octa
  • the M layer produces both photocurrent enhancement and broader spectral sensitivity.
  • the M material is present in the middle of the device and the D and A materials are both polymers that form an interpenetrating network extending to either side so that there is a large D-A junction area throughout the device. A separate dopant is incorporated from each side of the device.
  • US-A-5670791 describes a photovoltaic cell in which first and second semi-conductive polymers are arranged between ITO and Al electrode ' s. The two polymers form distinct phases in a phase separated blend.
  • US-A-6007928 describes an electroluminescent cell comprising ITO and aluminium electrodes separated by a block copolymer having a first block of poly-N-carbazole (hole conducting) and a second block of poly-2- ⁇ -naphthyl-5- (4- vinylphenyl) -oxadiazole (electron conductor). How the polymer blocks arrange themselves in the layer of block copolymer is not disclosed. 0' Regan, B et al, Letters to Nature, Nature, vol 353, 24
  • US-A-5665857 discloses electroluminescent devices having a conductive polymer layer sandwiched between a hole conducting layer and an electron conducting layer, each of unspecified nature.
  • the polymer layer conducts both electrons and holes and has dye molecules incorporated into its structure.
  • US-A-4360703 proposes a photovoltaic cell having ⁇ a molecular p-n junction' formed by an organic compound having a monomeric electron donor portion and a monomeric electron acceptor portion linked via a linkage portion. The compound forms a self-ordered mono-molecular film in which the donor and acceptor portions of the molecules self aggregate as upper and lower layers.
  • US-A-5201961 describes photovoltaic cells having between electrodes three organic layers, where a first layer is a monomeric electron acceptor compound, a middle layer is a monomeric dye compound (such as chloroaluminumphthalocyanine) and the last layer is a conductive polymer (polyaniline or poly-3-hexylthiophene) . A similar disclosure is found in US- A-5350459.
  • W094/15368 discloses a tuneable light emitting diode comprising a three block copolymer having two non- ⁇ - conjugated polymer blocks, one being hole conducting and the other being electron conducting together with a ⁇ -conjugated block, the length of which mainly determines the frequency of the emitted light.
  • all three blocks may be ⁇ conjugated, but there is a large difference in band gaps between the outer and middle blocks resulting in no ⁇ conjugation between the blocks.
  • the ability of the polymers to self assemble into microphase separated ordered structures is mentioned.
  • US-A-5454880 discloses photovoltaic devices in which a p-n junction is formed between an electron donor conductive polymer and an electron accepting polymer comprising fullerenes mixed into or bound in the electron accepting polymer.
  • the present invention now provides a photovoltaic cell or electroluminescent cell comprising a first electrode and a second electrode separated by a dye linked block polymer material, the molecules of which comprise in electrical connection with said first electrode an n-type semiconductor polymer block linked via a light absorbing monomeric dye moiety to a p-type semiconductor polymer block in electrical connection with said second electrode, the two polymer blocks being phase separated into distinct layers.
  • the n-type semiconductor polymer block and the p-type semiconductor polymer block are each independently formed from selected polymers formed from terphenylene- vinylene, polyaniline, polythiopene, poly (2-vinylpyridine) , poly (N-vinylcarbazole) , poly-acetylene, poly (p-phenyl- enevinylene) , poly-m-phenylene, poly-p-phenylene, poly-2,6- pyridine, or polypyrrole monomer, said polymers being substituted with electron withdrawing substituents in the case of the n-type polymer block and with electron donating substituents in the case of the p-type polymer block.
  • the backbone polymer of the n- and p-type blocks may be the same or different.
  • the dye moiety is a phenanthroimidazole, trioxatriangulene, azadioxatriangulene, diazaoxatriangulene, triazatriangulene, perylene, porphyrin, or phthalocyanine.
  • the dye moiety may be linked to one or both of the polymer blocks by covalent bonding, by ionic interaction, or by hydrogen bonding:
  • the dye moiety is a monomeric compound rather than a conjugated polymer. It should strongly absorb light in the wavelength range 300-1000 nm.
  • the anode and/or the cathode are covalently bonded to the n-type or p-type polymer blocks respectively.
  • n-type polymer blocks and the p-type polymer blocks of the diblock polymer material preferably each self assemble into mono-layers separated by said dye moiety.
  • each electrode is preferably matched to the work function of the polymer in contact with that electrode so that carrier transfer between each polymer and its respective electrode is obtained with substantially no barrier energy.
  • the barrier energy is preferably below 0.5 eV more preferably below 0.2 eV.
  • the first electrode has a relatively low work function as compared to the second electrode and suitably the work function of the first electrode is from 2.5 to 3.8 eV and the work function of the second electrode is from 4.0 to 5.7 eV.
  • the first electrode may be of calcium, aluminium, scandium, neodynium, yttrium, samarium, europium, magnesium or magnesium-indium, alloy and the second electrode may be of gold, silver, nickel, platinium, tungsten, chromium, or indum-tin-oxide (ITO) .
  • ITO indum-tin-oxide
  • Said molecules of the dye linked block polymer material may comprise multiple units of n-type semiconductor polymer block - dye moiety - p-type semiconductor polymer block joined head to tail and extending between said electrodes.
  • the p-type block, the monomeric dye and the n-type block all form a covalently bonded system.
  • Figure 1 shows a schematic drawing of a dye-linked block polymer photovoltaic cell (left) with a more detailed illustration of the molecular structure of the dye-linked block polymer (right) ;
  • Figure 2 shows two alternative structures for dye-linked block polymers for use in the invention
  • Figure 3 shows a scheme for assembling photovoltaic cells according to the invention
  • Figure 4 shows a second scheme for assembling photovoltaic cells according to the invention.
  • the polymers may be disperse or mono- disperse and they may be of small or large molecular weight.
  • Figure 2 shows at (a) a dye-linked diblock copolymer, where one block is mainly electron conducting and the other block is mainly hole conducting.
  • a schematic representation of the diblock copolymer is shown in which the zig-zag line represents a block of the type of polymer conducting preferentially one type of carriers i.e. holes.
  • This polymer region is linked covalently to a dye molecule represented by the square block which in turn is covalently linked to the other type of polymer (straight solid black line) which conducts with preference the other type of carrier i.e. electrons.
  • the absorption coefficient of the dye region or molecule is very high and serves the purpose of absorbing the light and generating charge carriers (holes and electrons) .
  • the absorption coefficient of the polymer blocks may both be high, one may be high and the other low or both may be low.
  • the absorption or transmission of light may be in the same span of wavelengths or in different spans for all three regions, n-block, p-block and dye.
  • a schematic representation of a second type of dye- linked block polymer material is shown at (b) .
  • the zig-zag line represents one type of polymer conducting preferentially one type of carrier i.e. holes.
  • This polymer region is linked covalently linked to a dye molecule (dark grey square) .
  • the dye molecule is functionalised by being covalently linked to a complex forming molecule (donor, acceptor, receptor or ligand) which may or may not absorb light (illustrated as a rightward facing cup) .
  • the other polymer block (straight solid black line) conducts with preference the other type of carrier i.e.
  • the absorption coefficient of the dye region or molecule is very high and serves the purpose of absorbing the light and generating charge carriers (holes and electrons) .
  • the absorption coefficient of the polymer blocks may both be high, one may be high and the other low or both may be low.
  • the absorption or transmission of light may be in the same span of wavelengths or in different spans for all three regions, n-block, p-block and dye.
  • the absorption of light is either in the dye-complex region alone (by charge transfer or simple bandgap) , or in the polymer regions and the complex region.
  • the complex can be of at least three types: donor-acceptor, metal-ligand, receptor-analyte type.
  • the bonding between the two parts of the complex forming moiety may be by hydrogen bonding or other Van der Waals bonding or by ionic interaction.
  • one or both ends of the molecules maybe end functionalised for the purpose of assembly of the cell and this process of end functionalisation may take place before, during or after the synthesis of the polymer systems or subsystems themselves.
  • the synthetic procedures leading to these polymers may be condensation type polymerisations, block build up polymerisations and controlled termination polymerisations.
  • the assembly process may be one of the overall types described below.
  • the illustrated processes always start at one electrode.
  • the types of process described are simple self assembly directly onto to the surface of one electrode, multiple steps of assembly onto the electrode, assembly in solution followed by assembly onto the surface, surface activation followed by assembly or polymerisation or assembly by chemical linkage to the surface.
  • the application of the polymers may be performed by, spin-coating, dip-coating, casting, in-situ pyrolysis, in-situ polymerisation, or complexation.
  • self-assembly directly onto the electrode surface is obtained by treating the cleaned electrode surface with a solution of the polymer system.
  • the illustration shows how the polymer systems have been end functionalised so that the molecules adsorb onto the surface. Both examples of the polymer types described with reference to Figure 2 are shown.
  • the surface electrode is shown as a thick black horizontal line.
  • several isolated processes are possible, i.e. first adsorption of one block followed by a separated process with complex formation or in-situ adsorption and complex formation.
  • the horse-shoe shaped objects illustrate a suitable end-functionalisation with a large specificity for the surface.
  • Preparation of the electrode surface may be carried out in which a polymerisation initiator or complexer is first chemically bound to the surface of interest as shown in step (a) . In some cases this step may be omitted and the affinity of the polymer may be for the electrode surface as such.
  • step (a) shows in step (a) how a suitable linker is connected to the cleaned electrode surface.
  • the reaction is performed from solution or gas phase and modifies the surface chemically so that adsorption of polymer systems can be made by covalent-, ionic- or complex bond formation.
  • the polymer systems are attached to the surface in step (b) following on from surface preparation.
  • the bond between the surface groups and the polymer may be of the covalent-, ionic- or complex formation type.
  • the chemically prepared surface is used as an initiator for a sequential polymerisa- tion process which can be in solution or by heating a pre- polymer which has been coated on to the surface.
  • a sequential polymerisa- tion process which can be in solution or by heating a pre- polymer which has been coated on to the surface.
  • the process can be continued by attaching a dye molecule that then serves as an initiator for polymerisation of a new type of polymer.
  • the polymer can be terminated with a complex molecule so that assembly can be achieved with another polymer system.
  • the first electrode on which the polymer assembly takes place as described above may be transparent (metal oxide, polymer type, metallic) or it may be non-transparent
  • the second electrode is applied by an evaporation, sputtering, coating or ablation technique.
  • the iodo-porphyrin-aldehyde compound 1 prepared according to Rao et al. J. Org. Chem. 2000, 65, 7327-7244) .
  • Compound 2 was used as a macro-initiator in an atom transfer radical polymerisation (ATRP) polymerisation with N- vinyl-carbazole.
  • ATRP atom transfer radical polymerisation
  • the macroinitiator (2) was mixed with equimolar amounts of copper (I) chloride, 2, 2 ' -bipyridine N-vinyl-carbazole (10 molar equivalents) in toluene.
  • the reaction mixture was degassed and heated to reflux. After the polymerisation reaction the mixture was cooled and diluted with tetrahydrofuran and filtered through a layer of alumina to remove the copper salts.
  • the solvents were removed in vacuum and the product was repeatedly precipitated from a chloroform solution with a large excess of methanol.
  • Iodo-porphyrin-polyvinylcarbazole 3 (5.3 g) was mixed with 4-carboxy-phenylboronic acid (1 g, excess) in a mixture of toluene (100 mL) and 2 M sodium carbonate. The reaction mixture was degassed with argon and the catalyst PdCl 2 (PPh 3 ) 2 (100 mg) was added. The reaction was heated to reflux overnight to complete the coupling. The cooled reaction mixture was separated and the organic phase was evaporated to dryness. The product was precipitated repeatedly from a chloroform solution by addition of a large excess of methanol.
  • the photovoltaic molecule was dissolved in chloroform at a concentration of 7 mg mL -1 . Careful addition of this onto a water surface using standard LB-techniques and compressing to a surface pressure of 20 N ⁇ f 1 allowed for a good film to be obtained that could be transferred onto a ITO substrate or ITO with a thin semitransparent chromium linked gold film. Evaporation of Ca, Al, Mg, Y, Nd, S , Eu, Sc, Ag, V, Nb, Cr, Fe or Cu on top (using an optional LiF tunnel barrier for the very low work function metals, deposited by sputtering or evaporation) . Subsequent measurement of the photovoltaic response in vacuum gave efficiencies in the range 1-100% at current densities of 1-10 9 pA cm 2 .
  • Compound A and compound B forms a charge transfer complex upon mixing.
  • the assembly A was prepared as described below
  • N,N' -Dibenzyl-naphthalene-1, 5-diamine (7) Naphthalene- 1,5-diamine (100 g) and benzaldehyde (74 g) were mixed neat with a little acetic acid to prepare the imide. THF (1L) was added together with acetic acid (180 mL) . The mixture was cooled on an ice-bath and stirred vigorously while NaBH 4 (56g) was added in small portions (Caution! the reaction is exothermic and hydrogen is evolved) . After 1 hr water was added (2L) slowly to avoid excessive foaming. Separation of the raw product by filtration followed by recrystalization from toluene (5 L) gave the product 3 as a white powder. Yield: -375g.
  • N,N' -Dibenzyl-1, 5-Bis-chlorocarbonylamino-naphthalene (8) 1, 5-Dibenzylaminonaphthalene (7) (34g) was placed in a flask containing chloroform / toluene (1:1) (200mL) and triethyl amine (40mL) . Phosgene (150mL, 20% in toluene) was added. The mixture becomes warm and the colour changes to a deeper yellow. A precipitate of the triethyl ammonium hydrochloride forms. After lh the mixture was washed with water and dried (MgS0 4 ) .
  • the assembly B was prepared as described below
  • the disulfide of compound A was dissolved in chloroform at a concentration of 0.1 mg mL -1 .

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Mathematical Physics (AREA)
  • Theoretical Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Graft Or Block Polymers (AREA)
  • Photovoltaic Devices (AREA)

Abstract

L'invention concerne une cellule photovoltaïque électroluminescente comprenant une première électrode et une seconde électrode séparée par une molécule de polymère séquencé liée par un colorant, laquelle molécule contient un polymère séquencé semi-conducteur de type n lié par l'intermédiaire d'un fragment de colorant monomère photoabsorbant à un polymère séquencé semi-conducteur de type p; les deux polymères séquencés étant séparés en phases en deux couches distinctes. Le polymère séquencé semi-conducteur de type n et le polymère séquencé semi-conducteur de type p sont, indépendamment l'un de l'autre, constitués de polymères formés à partir de terphénylènevinylène, de polyaniline, de polythiopène, de poly (2-vinyl-pyridine), de poly(N-vinylcarbazole), de poly-acétylène, de poly (p-phénylènevinylène), de poly-m-phénylène, de poly-p-phénylène, de poly-2,6-pyridine, ou d'un monomère de polypyrrole. Ces polymères sont substitués avec des substituants attracteurs d'électrons dans le cas du polymère séquencé de type n et avec des substituants donneurs d'électrons dans le cas du polymère séquencé de type p.
PCT/EP2003/010258 2002-09-27 2003-09-16 Guidage de dispositifs polymeres pour interconvertir de la lumiere et de l'electricite Ceased WO2004030029A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003282015A AU2003282015A1 (en) 2002-09-27 2003-09-16 Conducting polymer devices for inter-converting light and electricity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0222510.0 2002-09-27
GBGB0222510.0A GB0222510D0 (en) 2002-09-27 2002-09-27 Conducting polymer devices for inter-converting light and electricity

Publications (2)

Publication Number Publication Date
WO2004030029A2 true WO2004030029A2 (fr) 2004-04-08
WO2004030029A3 WO2004030029A3 (fr) 2004-05-27

Family

ID=9944913

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/010258 Ceased WO2004030029A2 (fr) 2002-09-27 2003-09-16 Guidage de dispositifs polymeres pour interconvertir de la lumiere et de l'electricite

Country Status (3)

Country Link
AU (1) AU2003282015A1 (fr)
GB (1) GB0222510D0 (fr)
WO (1) WO2004030029A2 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006060017A1 (fr) * 2004-12-02 2006-06-08 The Trustees Of Princeton University Dispositifs photosensibles semi-conducteurs employant des complexes photosynthétiques isolés
WO2006097419A1 (fr) * 2005-03-14 2006-09-21 Ciba Specialty Chemicals Holding Inc. Nouveaux polymeres
GB2434485A (en) * 2006-01-19 2007-07-25 Riso Nat Lab Solar cell
WO2007101820A1 (fr) * 2006-03-08 2007-09-13 Ciba Holding Inc. Réaction de polymérisation catalysée au palladium
WO2008006743A1 (fr) * 2006-07-14 2008-01-17 Ciba Holding Inc Nouveaux polymères électroluminescents pour applications éléctroniques
WO2007095171A3 (fr) * 2006-02-14 2008-04-17 Massachusetts Inst Technology Film absorbant
US7557433B2 (en) 2004-10-25 2009-07-07 Mccain Joseph H Microelectronic device with integrated energy source
US7592539B2 (en) 2003-11-07 2009-09-22 The Trustees Of Princeton University Solid state photosensitive devices which employ isolated photosynthetic complexes
US8048542B2 (en) * 2009-04-02 2011-11-01 National Tsing Hua University Bis-phenanthroimidazolyl compound and electroluminescent device using the same
CN102344549A (zh) * 2010-07-30 2012-02-08 海洋王照明科技股份有限公司 含咔唑卟啉-吡咯并吡咯共聚物及其制备方法和应用
US8138303B2 (en) * 2006-02-10 2012-03-20 Basf Se Polymers
EP2514736A1 (fr) 2006-07-28 2012-10-24 Basf Se Produits intermédiaires de polymères

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5201961A (en) * 1990-05-23 1993-04-13 Ricoh Company, Ltd. Photovoltaic device containing organic material layers and having high conversion efficiency
JPH1160660A (ja) * 1997-08-11 1999-03-02 Jsr Corp ブロック共重合体およびその製造方法

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9099410B2 (en) 2003-10-13 2015-08-04 Joseph H. McCain Microelectronic device with integrated energy source
US7592539B2 (en) 2003-11-07 2009-09-22 The Trustees Of Princeton University Solid state photosensitive devices which employ isolated photosynthetic complexes
US7557433B2 (en) 2004-10-25 2009-07-07 Mccain Joseph H Microelectronic device with integrated energy source
WO2006060017A1 (fr) * 2004-12-02 2006-06-08 The Trustees Of Princeton University Dispositifs photosensibles semi-conducteurs employant des complexes photosynthétiques isolés
WO2006097419A1 (fr) * 2005-03-14 2006-09-21 Ciba Specialty Chemicals Holding Inc. Nouveaux polymeres
US8445630B2 (en) 2005-03-14 2013-05-21 Basf Se Polymers
GB2434485A (en) * 2006-01-19 2007-07-25 Riso Nat Lab Solar cell
US8138303B2 (en) * 2006-02-10 2012-03-20 Basf Se Polymers
US8809876B2 (en) 2006-02-14 2014-08-19 Massachusetts Institute Of Technology Absorbing film
WO2007095171A3 (fr) * 2006-02-14 2008-04-17 Massachusetts Inst Technology Film absorbant
WO2007101820A1 (fr) * 2006-03-08 2007-09-13 Ciba Holding Inc. Réaction de polymérisation catalysée au palladium
WO2008006743A1 (fr) * 2006-07-14 2008-01-17 Ciba Holding Inc Nouveaux polymères électroluminescents pour applications éléctroniques
US8221906B2 (en) 2006-07-14 2012-07-17 Basf Se Electroluminescent polymers for electronic applications
CN101490125B (zh) * 2006-07-14 2012-11-14 西巴控股有限公司 用于电子应用的新型电致发光聚合物
EP2514736A1 (fr) 2006-07-28 2012-10-24 Basf Se Produits intermédiaires de polymères
US8048542B2 (en) * 2009-04-02 2011-11-01 National Tsing Hua University Bis-phenanthroimidazolyl compound and electroluminescent device using the same
CN102344549A (zh) * 2010-07-30 2012-02-08 海洋王照明科技股份有限公司 含咔唑卟啉-吡咯并吡咯共聚物及其制备方法和应用

Also Published As

Publication number Publication date
AU2003282015A1 (en) 2004-04-19
GB0222510D0 (en) 2002-11-06
WO2004030029A3 (fr) 2004-05-27
AU2003282015A8 (en) 2004-04-19

Similar Documents

Publication Publication Date Title
Sonar et al. High mobility organic thin film transistor and efficient photovoltaic devices using versatile donor–acceptor polymer semiconductor by molecular design
Wong Luminescent organometallic poly (aryleneethynylene) s: functional properties towards implications in molecular optoelectronics
EP3044817B9 (fr) Cellule solaire inversée et son procédé de fabrication
JP5548933B2 (ja) 光電変換素子およびその素子を用いた太陽電池
EP2463929A1 (fr) Élément de conversion photoélectrique et cellule solaire utilisant celui-ci
JP6737798B2 (ja) 光電子及び光電気化学デバイスのための小分子ホール輸送材料
CN115322121B (zh) 一种有机空穴传输材料及其制备得到的钙钛矿太阳能电池
JP2017505995A (ja) 固体太陽電池セル用の正孔輸送性かつ光吸収性の材料
JP2017505995A5 (fr)
US8389696B2 (en) Polymerizable diazonium salts, process for the preparation thereof and uses thereof
WO2004030029A2 (fr) Guidage de dispositifs polymeres pour interconvertir de la lumiere et de l'electricite
TW200844096A (en) Noble ruthenium-type sensitizer and method of preparing the same
KR102611766B1 (ko) 페로브스카이트 태양전지용 정공전달물질 및 이를 포함하는 페로브스카이트 태양전지
JP5531241B2 (ja) フラーレン誘導体、半導体材料、光電変換素子及び太陽電池
JP2013055322A (ja) 光電変換素子、太陽電池及び太陽電池モジュール
WO2013176156A1 (fr) Matière organique donneuse d'électrons, matière pour élément de puissance photovoltaïque utilisant celle-ci et élément de puissance photovoltaïque utilisant celle-ci
CN103635482B (zh) 钴配合物在制备光伏电池中的活性层中的用途以及相应的光伏电池
Man et al. Fabrication of photovoltaic cells using rhenium diimine complex containing polyelectrolytes by the layer-by-layer electrostatic self-assembly method
Marqués et al. Synthesis, characterization and use of a POSS-arylamine based push–pull octamer
JP6230051B2 (ja) 配位高分子薄膜およびそれを備えた薄膜太陽電池の製造方法
GRIGORAS CONDUCTIVE POLYMERS: FROM SYNTHESIS TO PROPERTIES AND APPLICATIONS
Aydın SYNTHESIS OF F AND Cl CONTAINING NOVEL QUINOXALINE-BASED CONJUGATED POLYMERS FOR ORGANIC SOLAR CELL
CN121318974A (zh) 具有二氮杂三聚茚衍生物的化合物及包含其的光电转换元件、钙钛矿太阳能电池、电子设备及电子元件
CN118812587A (zh) 一种四环芳烃膦酸衍生物、制备方法及其在钙钛矿基太阳能电池中的应用
Fischer Functionalized dendritic oligothiophenes-applications in organic solar cells

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP