EP1476881A2 - Materiau semi-conducteur organique dope et son procede de production - Google Patents

Materiau semi-conducteur organique dope et son procede de production

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Publication number
EP1476881A2
EP1476881A2 EP03722191A EP03722191A EP1476881A2 EP 1476881 A2 EP1476881 A2 EP 1476881A2 EP 03722191 A EP03722191 A EP 03722191A EP 03722191 A EP03722191 A EP 03722191A EP 1476881 A2 EP1476881 A2 EP 1476881A2
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EP
European Patent Office
Prior art keywords
semiconductor material
organic semiconductor
material according
doped organic
carbon atoms
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Ceased
Application number
EP03722191A
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German (de)
English (en)
Inventor
Ansgar Werner
Martin Pfeiffer
Torsten Fritz
Karl Leo
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NovaLED GmbH
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NovaLED GmbH
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Publication of EP1476881A2 publication Critical patent/EP1476881A2/fr
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B15/00—Acridine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B17/00—Azine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B19/00—Oxazine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B21/00—Thiazine dyes
    • 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 a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • 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
    • 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
    • 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]
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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
    • H10K85/111—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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • 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
    • 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
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the invention relates to doped organic semiconductor material with increased charge carrier density and effective charge carrier mobility according to claim 1, a method for producing the doped organic semiconductor material according to claim 48 and the use of the semiconductor material.
  • organic light-emitting diodes and solar cells Since the demonstration of organic light-emitting diodes and solar cells in 1989 [C.W. Tang et al., Appl. Phys. Lett. 51 (12), 913 (1987)] are components of organic thin films which are the subject of intensive research. Such layers have advantageous properties for the applications mentioned, such as efficient electroluminescence for organic light-emitting diodes, high absorption coefficients in the range of visible light for organic solar cells, inexpensive manufacture of materials and manufacture of components for the simplest electronic circuits, among others The use of organic light-emitting diodes for display applications is already of commercial importance.
  • the performance characteristics of (opto) electronic multilayer components are determined, among other things, by the ability of the layers to transport the charge carriers.
  • the ohmic losses in the charge transport layers during operation are related to the conductivity, which on the one hand has a direct influence on the required operating voltage, but on the other hand also determines the thermal load on the component.
  • the charge carrier concentration of the organic layers there is a band bending in the vicinity of a metal contact, which facilitates the injection of charge carriers and can thus reduce the contact resistance. Similar considerations for organic solar cells lead to the conclusion that their efficiency is also determined by the transport properties for charge carriers.
  • Doped organic charge transport layers have already been successfully used to improve organic light-emitting diodes.
  • the hole transport layer By doping the hole transport layer with the acceptor material F4TCNQ, the operating voltage of the light-emitting diode is drastically reduced (X. Zhou et al, Appl. Phys. Lett., 78 (4), 410 (2001).).
  • a similar success can be achieved by doping the electron-transporting layer with Cs or Li (J. Kido et al., Appl. Phys. Lett., 73 (20), 2866 (1998); J.-S. Huang et al. , Appl. Phys. Lett., 80, 139 (2002)).
  • the electrical doping with inorganic materials suffers from the lack that the atoms or molecules used are easy in the component due to their small size can diffuse and thus complicate a defined production, for example, sharp transitions from p-doped to n-doped regions. In contrast, diffusion plays a subordinate role when large organic molecules are used as dopants. However, their use is impaired by the fact that potential doping molecules must be characterized by extreme values of the electron affinity for the p-doping or the ionization potential for the n-doping. This is accompanied by a decreasing chemical stability of the molecules.
  • the object of the invention is now to provide a solution for overcoming the chemical instability of efficient doping molecules mentioned and the production of layers doped therewith.
  • organic molecules are used which, although unstable in the neutral state, are stable as a charged cation or anion or in connection with a covalent connecting partner.
  • These charged molecules are made in situ from a precursor compound that is converted into the desired charged molecule before, during, or after the vapor deposition process.
  • a connection may e.g. an organic salt or a metal complex.
  • the unstable dopant can also be generated in situ from a stable precursor.
  • the doping molecule used has been introduced into the layer to be doped in the neutral state, in order to then be present as an anion or cation after a charge transfer to the matrix.
  • the use of the neutral molecule is therefore only an intermediate step in bringing about the charge transfer.
  • the associated stability problems already described can be avoided according to the invention by using an already ionized, stable molecule as dopant.
  • An advantageous solution according to the invention is, for example, the use of a laser for the evaporation of rhodamine B chloride, which leads to the predominant production of rhodamine B cations.
  • the purpose of the invention can also be achieved if a neutral radical is first generated from the compound according to claim 1, which is sufficiently stable in situ to be able to Layer to be installed, and this in the layer is subject to a transfer of the radical electron to the matrix or a recording of another electron from the matrix.
  • No. 5,811,833 describes an electron transport layer consisting of free radicals, in particular pentaphenylcyclopentadienyl, for use in organic light-emitting diodes.
  • US Pat. No. 5,922,396 shows that such a layer can be produced from organometallic compounds, in particular from decaphenylgermanocen or decaphenylplumbocen (see also M. L Heeg, J. Organometallic Chem., 346, 321 (1988)).
  • 5,922,396 lead to layers with increased microscopic charge carrier mobility (or the transfer rates in the hopping process), since a negatively charged pentaphenylcylclopentadienyl molecule has an aromatic character, and thus the electron transfer to an adjacent neutral pentaphenylcyclopentadienyl molecule due to the electron overlap of the pi orbitals the phenyl groups of the molecules involved is improved.
  • the increase in conductivity is achieved by increasing the microscopic mobility of the charge carriers (or the transfer rates in the hopping process).
  • the equilibrium charge carrier density is increased according to the invention in order to increase the conductivity. Discrimination is possible, for example, through time-of-flight (measurement of charge carrier mobility), the Seebeck effect or the field effect (measurement of charge carrier density).
  • the invention further relates to the use of the doping molecules in mixed layers which additionally contain materials in order to achieve a further purpose.
  • These purposes can, for example, change the layer growth, the production of interpenetrating Networks (CJ Brabec et al., Adv. Mater., 11 (1), 15 (2001)), or in organic light-emitting diodes to improve the quantum efficiency of light emission or change the color of the emitted light by adding a luminescent dye substance.
  • cationic dyes such as rhodamine B often have a high luminescence quantum yield, which enables use as luminescence dyes in organic LEDs.
  • this invention also encompasses the use of molecules from claim 1 for doping polymer layers.
  • Such layers are typically produced by a spin coating process by deposition from the solution.
  • the present invention enables the polymer layers to be doped with large, non-mobile molecules.
  • An exemplary embodiment to illustrate the invention consists in the use of the dye molecule rhodamine B chloride as dopant. If a mixed layer of naphthalene tetracarboxylic acid dianhydride (NTCDA) and rhodamine B in the ratio (150: 1) is produced, the conductivity is le-5 S / cm at room temperature, which corresponds to an increase of 4 orders of magnitude compared to a pure NTCDA layer.
  • NTCDA naphthalene tetracarboxylic acid dianhydride
  • Rhodamine B chloride molecules disintegrate into positively charged Rhodamine B molecules and negatively charged chloride ions during heating in the cuvette. The charged rhodamine B molecules are built into the mixed layer.
  • the electrons required to maintain the charge neutrality of the entire layer remain on the NTCDA molecules, since the electron affinity of NTCDA is higher than that of rhodamine B (3.2 eV, H. Meier, "Organic Semiconductors", Verlag Chemie Weinheim, 1974, p. These electrons fill the lowest unoccupied orbitals of the NTCDA and thus increase the conductivity.
  • the increased density of the charge carriers can be determined, for example, by measurements of the Seebeck coefficient and the field effect. Field effect measurements on a sample made of NTCDA doped with pyronin B (50: 1 ) confirms the presence of electrons as majority carriers with a concentration of 10 17 cm "3 .
  • rhodamine B The doping effect of rhodamine B was also used for matrices made of MePTCDI (perylene-3,4,9,10-tetracarboxylic acid-N, N'-dimethyl-diimide) and PTCDA (3,4,9,10-
  • TTF tetrathiafulvalene
  • SCE oxidation potential
  • Stronger donors i.e. Dopants with a lower oxidation potential are unstable in air (GC Papavassiliou, A. Terzis, P. Delhaes, in: HS Nalwa (Ed.) Handbook of conductive molecules and polymers, Vol. 1: charge-transfer salts, fillers and photoconductors, John Wiley & Sons, Chichester, 1997).
  • Rhodamine B has a reduction potential of -0.545 V versus NHE (M. S. Chan, J. R.
  • the reduction potential of the organic salt rhodamine B is determined by the reduction potential of the rhodamine B cation. This value is equal to the oxidation potential of the neutral Rhodamine B radical.
  • the rhodamine B radical is a stronger donor than TTF.
  • this strong donor rhodamine B is stable. So far it has been possible to use donors with an oxidation potential greater than +0.35 V against SCE, but the invention described here allows doping with donors whose oxidation potential is less than +0.35 V against SCE.
  • Chemically stable compounds within the meaning of claim 1 are, for example, ionic dyes. These are used in photography to sensitize AgBr, for example.
  • the electron affinity of AgBr is 3.5eV.
  • Dyes which can sensitize AgBr by electron transfer are also suitable as chemically stable compounds for use in doping organic semiconductor materials within the meaning of claim 1.
  • a subclass of the ionic dyes are the di- and triphenylmethane dyes and their known analogues of the general structure T 2 and T 2
  • X CR 4 , SiR 4 , GeR 4 , SnR 4 , PbR 4 , N, P and Rl, R2, R3 and R 4 are suitable, known substituents, for example in each case one or more: hydrogen; Oxygen; Halogens, for example fluorine, chlorine, bromine or iodine; hydroxyl; Aminyl, for example diphenylaminyl, diethylaminyl; Aliphatics with 1 to 20 carbon atoms, for example methyl, ethyl, carboxyl; Alkoxyl, for example: methoxy; cyano; nitro; Sulfonic acid and its salts; Aryl having 3 to 25 carbon atoms, for example phenyl, pyridyl or naphthyl or those atoms which form a condensed ring. One or more p-position substitutions of the phenyl groups can often be found (M 3 to M 6).
  • X CR8, SiR8, GeR8, SnR8, PbR8, N, P and Rl to R7 and R8 are suitable known substituents, e.g. one or more each: hydrogen; Oxygen; Halogens, e.g. Fluorine, chlorine, bromine or iodine; hydroxyl; Aminyl, e.g. Diphenylaminyl, diethylaminyl; Aliphates with 1 to 20 carbon atoms, e.g. Methyl, ethyl, carboxyl; Alkoxyl e.g. methoxy; cyano; nitro; Sulfonic acid and its salts; Aryl of 3 to 25 carbon atoms, e.g.
  • diphenylmethane dyes are Auramin O (CI 655) or Auramin G (CI 656).
  • triphenylmethane dyes are malachite green (CI 657), turquoise blue (CI 661), fluorescein (CI 45350) or patent blue V (CI 712).
  • the representative of the triphenylmethane dyes malachite green chloride produces a conductivity of 4-10 "4 S / cm in an NTCDA matrix with a doping ratio of 1: 122.
  • Malachite green is therefore a compound in the sense of claim 11 and in particular in the sense of subclaims 12 to 22 This property is brought about by the valence structure of the central carbon atom (main group 4), and other known compounds of this type of structure with atoms of the main group 4 as central atom (triarylsilyl, germyl, stannyl, plumbyl) are accordingly likewise suitable as a compound in the sense of claims 1, 12 to 22.
  • Compounds in which there is a direct bond between 2 carbon atoms of each phenyl ring of the di- or triphenylamine are contained in claims 23 to 25.
  • Rhodamine B base has a doping effect on a PTCDA matrix, for example a conductivity of 7 * 10-5 S / cm for a 1:70 doping.
  • xanthene dyes Another group of ionic dyes are the xanthene dyes.
  • the Rhodamine B listed above is a representative of this class. Pyronin B, Rhodamine 110 and Rhodamine 3B as further representatives of this class of materials also have a doping effect.
  • the xanthene dyes are similar the pyran, thiopyran, indamine, acridine, azine, oxazine and thiazine dyes, which differ in substitutions in the multinuclear heterocycle. Because of the otherwise identical structure, these dye classes (T 9) are also suitable compounds in the sense of claims 1, 23 to 26.
  • N, N'-diethyl-cyanine and N.N'-diethyl-thiacarbocyanine increase the conductivity to 3-10 "5 S / cm (1:11 doping ratio) or 5-10 " 5 S / cm (1:47 doping ratio).
  • These two dyes are each a representative of the polymethm dyes with a specific choice of X and Z.
  • the leuco bases of ionic dyes are also suitable compounds in the sense of claims 1, 12 to 26.
  • rhodamine B base in NTCDA gives a conductivity of 3-10 "5 S / cm (1:70 doping ratio).
  • Organic salts are often based on suitable heterocycles (e.g. pyridinium, pyrrolium, pyrylium, thiazolium , Diazininium, thininium, diazolium, thiadiazolium or dithiolium etc. individually or as part of a multinuclear heterocycle) or suitable groups (eg ammonium, sulfonium, phosphonium, iodonium etc.).
  • suitable heterocycles e.g. pyridinium, pyrrolium, pyrylium, thiazolium , Diazininium, thininium, diazolium, thiadiazolium or dithiolium etc. individually or as part of a multinuclear heterocycle
  • suitable groups eg ammonium, sulfonium, phosphonium, iodonium etc.
  • the vaporized substance is oxidized under the influence of oxygen. This process also takes place in a mixed layer of matrix and dopant. Evaporation mixed layers of pyronine B chloride and tetracyanoquinodimethane are immediately colored red, and the presence of tetracyanoquinodimethane anions can be detected by UV / VIS and FTIR spectroscopy.

Abstract

L'invention concerne un matériau semi-conducteur organique dopé présentant une densité accrue des porteurs de charge et une mobilité réelle des porteurs de charge et obtenu par dopage d'un matériau semi-conducteur organique avec un composé chimique constitué d'un ou de plusieurs groupes moléculaires organiques A et d'au moins un autre constituant B. L'effet de dopage désiré est obtenu après séparation d'au moins un groupe moléculaire organique A du composé chimique au moyen d'au moins un groupe moléculaire organique A ou du produit d'une réaction d'au moins un groupe moléculaire A avec un autre atome ou une autre molécule. L'invention concerne également un procédé pour la production de ce matériau semi-conducteur organique dopé.
EP03722191A 2002-02-20 2003-02-20 Materiau semi-conducteur organique dope et son procede de production Ceased EP1476881A2 (fr)

Applications Claiming Priority (3)

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DE10207859A DE10207859A1 (de) 2002-02-20 2002-02-20 Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung
DE10207859 2002-02-20
PCT/DE2003/000558 WO2003070822A2 (fr) 2002-02-20 2003-02-20 Materiau semi-conducteur organique dope et son procede de production

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US (1) US7858967B2 (fr)
EP (1) EP1476881A2 (fr)
JP (1) JP2005525696A (fr)
KR (1) KR100679384B1 (fr)
CN (1) CN1698137B (fr)
AU (1) AU2003229476A1 (fr)
CA (1) CA2463377C (fr)
DE (2) DE10207859A1 (fr)
WO (1) WO2003070822A2 (fr)

Cited By (53)

* Cited by examiner, † Cited by third party
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WO2007022845A1 (fr) 2005-08-26 2007-03-01 Merck Patent Gmbh Nouvelles matieres pour des dispositifs electroluminescents organiques
WO2008006449A1 (fr) 2006-07-11 2008-01-17 Merck Patent Gmbh Nouveaux matériaux destinés à des dispositifs électroluminescents organiques
DE102007002714A1 (de) 2007-01-18 2008-07-31 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102007024850A1 (de) 2007-05-29 2008-12-04 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008017591A1 (de) 2008-04-07 2009-10-08 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
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WO2003070822A2 (fr) 2003-08-28
CN1698137A (zh) 2005-11-16
AU2003229476A8 (en) 2003-09-09
AU2003229476A1 (en) 2003-09-09
DE10307125B4 (de) 2017-06-22
CA2463377A1 (fr) 2003-08-28
US7858967B2 (en) 2010-12-28
DE10307125A1 (de) 2004-01-08
CA2463377C (fr) 2015-01-06
KR20050004768A (ko) 2005-01-12
CN1698137B (zh) 2012-09-05
KR100679384B1 (ko) 2007-02-05
DE10207859A1 (de) 2003-09-04
JP2005525696A (ja) 2005-08-25
WO2003070822A3 (fr) 2004-06-10
US20050040390A1 (en) 2005-02-24

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