WO2006081780A1 - Dopants pour semi-conducteurs organiques - Google Patents

Dopants pour semi-conducteurs organiques Download PDF

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Publication number
WO2006081780A1
WO2006081780A1 PCT/DE2005/000189 DE2005000189W WO2006081780A1 WO 2006081780 A1 WO2006081780 A1 WO 2006081780A1 DE 2005000189 W DE2005000189 W DE 2005000189W WO 2006081780 A1 WO2006081780 A1 WO 2006081780A1
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WO
WIPO (PCT)
Prior art keywords
aryl
perfluoroalkyl
heteroaryl
organic
dopant
Prior art date
Application number
PCT/DE2005/000189
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German (de)
English (en)
Inventor
Olaf Zeika
Horst Hartmann
Tatjana Wahl
Original Assignee
Novaled Ag
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.)
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Publication date
Application filed by Novaled Ag filed Critical Novaled Ag
Priority to JP2007553446A priority Critical patent/JP2008530773A/ja
Priority to PCT/DE2005/000189 priority patent/WO2006081780A1/fr
Publication of WO2006081780A1 publication Critical patent/WO2006081780A1/fr

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Classifications

    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/611—Charge transfer complexes
    • 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
    • H10K85/311—Phthalocyanine
    • 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

Definitions

  • the invention relates to a dopant for doping an organic semiconductive matrix material for changing the electrical properties thereof, the use of the dopant, a doped semiconductive matrix material and an electronic component made therefrom.
  • organic semiconductors can also be strongly influenced by doping with regard to their electrical conductivity.
  • Such organic semiconducting matrix materials can be constructed from either compounds with good electron donating properties or from compounds having good electron accepting properties.
  • strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyne (F4TCNQ) have become known.
  • TCNQ tetracyanoquinonedimethane
  • F4TCNQ 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyne
  • the compounds examined so far have disadvantages for the production of doped semiconducting organic layers or of corresponding electronic components with such doped layers, since the production processes in large-scale production plants or those on a pilot plant scale can not always be controlled sufficiently precisely, leading to high control and control effort within the processes leads to achieve a desired product quality, or undesirable tolerances of the products.
  • organic donors with respect to the electronic component structures such as light-emitting diodes (OLEDs), field effect transistor (FET) or solar cells themselves, since the mentioned production difficulties in handling the dopants to unwanted irregularities in the electronic components or unwanted aging effects of the electronic components being able to lead.
  • the dopants to be used have suitable electron affinities and other properties suitable for the application, since, for example, the dopants also determine the conductivity or other electrical properties of the organic semiconductive layer under given conditions.
  • the invention is therefore based on the object of providing organic dopants for doping organic semiconductors which are easier to handle in the production process and which lead to electronic components whose organic semiconducting materials can be produced in a reproducible manner.
  • this object is achieved by a dopant according to claim 1, wherein preferred embodiments result from the subclaims.
  • the dopants according to the invention exhibit an extremely high electron affinity, thermal stability, sublimability and diffusion resistance in semiconductor layers, whereby the combination of these properties could not be expected.
  • the volatility can be used as the under the same conditions (for example, a pressure of 2 x 10 "4 Pa and a predetermined evaporation temperature, for example 150 ° C) measured evaporation rate or rate of vapor deposition of a substrate measured as a layer thickness growth per unit time (nm / s) under otherwise identical conditions
  • the volatility of the compounds according to the invention is preferably ⁇ 0.95 or 0.9 times, particularly preferably ⁇ 0.8 times, more preferably ⁇ 0.5 times, particularly preferably ⁇ 0.1 -fold or ⁇ 0.05-fold or ⁇ 0.01-fold of F4TCNQ or less.
  • the evaporation rate of the substrate with the compounds according to the invention can be determined, for example, using a quartz thickness monitor, as is commonly used, for example, in the production of OLEDs.
  • the ratio of the occlusion rates of matrix materials and dopants can be measured by independent measurements using the same, using two separate quartz thickness monitors to adjust the doping ratio.
  • the volatility relative to that of F4TCNQ may refer respectively to that of the pure compound or to the volatility from a given matrix material, for example ZnPc.
  • the compounds of the invention are preferably such that they evaporate more or less or virtually undecomposed.
  • precursors as dopant source in a targeted manner which release the compounds used according to the invention, for example acid addition salts.
  • the dopant is selected such that under otherwise identical conditions such as in particular doping concentration (molar ratio of dopant: matrix, layer thickness, current strength) for a given matrix material (for example, zinc phthalocyanine or another matrix material mentioned below) generates a precisely as high or preferably a higher conductivity as F4TCNQ, for example, a conductivity (S / cm) of greater than or equal to 1.1 times, 1.2 times or greater / equal to 1.5 times or twice that of F4TCNQ as dopant.
  • the dopant used in the invention is selected such that the doped with this semiconducting organic matrix material after a temperature change of 100 ° C to room temperature (20 ° C) still> 20%, preferably> 30%, more preferably> 50% or 60% of Conductivity (S / cm) of the value at 100 ° C.
  • the dopants according to the invention have a high vaporization temperature or a low volatility, so that production processes for doping organic semiconducting materials can be better controlled and thus can be carried out with little effort and reproducibly.
  • the quinone derivative compounds which are proposed as dopants according to the present invention allow sufficient electrical conductivity of the organic semiconducting matrix with favorable electron affinity of the dopants, while at the same time providing low diffusion coefficients in the respective components which ensure component structures which are identical over time.
  • the charge carrier injection of contacts into the doped layer can be improved by the dopants according to the invention.
  • the doped organic semiconductor material or the resulting electronic component have improved long-term stability due to the compounds used in the invention. This concerns, for example, a reduction of the dopant concentration with time.
  • this relates to the stability of the doped layer disposed adjacent to undoped layers of an electro-optical device so that electro-optical devices having increased long-term stability of the electro-optical characteristics present the light output at a given wavelength, efficiency of a solar cell or the like.
  • dihydroquinone derivatives as synthetic precursors of the quinoid structures 40-48, which have the following structures:
  • Substituent S 12 is particularly suitable for structures 47a and 48a.
  • 1,4-quinones are best isolated by oxidation of the corresponding hydroquinones (WT Sumerford, DN Dalton, J. Am. Chem Soc 1944, 66, 1330, J. Miller, C. Vasquez, 1991 US506836, K. Koch J. Vitz, J. Prakt. Chem. 2000, 342/8 825-7) or the fluorinated and / or chlorinated aromatics. 1974, 107, 558-65, OIOsina, VD Steingarz, Zh. Org. Chim., 1974, 10, 329; VD Steingarz at al Zh. Org. Chim., 1970, 6 / 4, 833).
  • N, N'-dicyano-1,4-quinonediimines are prepared either by the action of N 5 N'-bistrimethylsilylcarbodiimide on 1,4-quinone compounds (A. Aumüller, S. Hünig, Liebigs Ann. Chem., 1986, 142 64,) or by oxidation of corresponding N, N'-dicyano-1,4-diamine compounds (GD Adreetti, S. Bradamante, PC Pizzarri, GA Pagani, Mol. Cryst. Liq. Cryst.
  • N, N'-dicyano-l, 4-diamine compounds can be obtained by cyanation of phenylene-l, 4-diamine with cyanogen halides or by desulfurization of corresponding thiourea derivatives.
  • Simple tetracyanoquinonedimethanes can be prepared via 1,4-cyclohexanedione by condensation in benzene with ammonium acetate buffer on a water separator and subsequent oxidation by bromine (DS Acker, WR Hertier, J. Am. Chem. Soc. 1962, 84, 3370).
  • Hertier and co-workers have also shown that these compounds can be synthesized via 1,4-xylene and its analogues by side chain bromination, substitution by cyanide, condensation with diethyl carbonate, conversion of the carboxylic acid methyl ester groups into cyanide groups and subsequent oxidation (J. Org. Chem. 1963, 28, 2719).
  • Acceptor-substituted tetracyanoquinonedimethanes can be prepared from the sodium salt of t-butyl malononitrile and acceptor-substituted 1,4-dihaloaromatic (R.C. Wheland, E.L. Martin, J. Org. Chem., 1975, 40, 3101).
  • Pyrazino-TCNQ compounds can be prepared via 5,8-diiodoquinoxa-line palladium-catalyzed with the sodium salt of malononitrile. (T. Miyashi et al, J. Org. Chem. 1992, 57, 6749-55)
  • Pyrazino-TCNQ compounds and other hetero-isolated derivatives can be prepared in various ways (Y. Yamashita et al. Chemistry Letters, 1986, 715-8, F. Wudl al., J. Org. Chem. 1977, 421666-7).
  • Annealed DCNQI compounds can be synthesized via the corresponding quinones according to Hünig (Tsunetsugu, J., et al., Chemistry Letters, 2002, 1004-5).
  • Hetero-annealed DCNQI compounds can be synthesized via the corresponding quinones according to Hünig (T. Suzuki et al., J. Org. Chem. 2001, 66, 216-24; N. Martin at al, J. Org. Chem. 1996, 61, Kobayashy et al., Chemistry Letters, 1991, 1033-6; K. Kobayashy, K. Takahashi, J. Org. Chem. 2000, 65, 2577-9).
  • Heterocyclic quinoid derivatives can be prepared according to N.F. Haley, J.C.S. Chem. Coirnn. 1979, 1031, F. Weydand, K. Henkel Chem. B. 1943, 76, 818; H.J. Knackmuss Angew. Chem. 1973, 85, 16; K.Fickentscher, Chem. B. 1969, 102, 2378-83, D.E. Burton et al J. Chem. Soc. (C) 1968, 1268-73.
  • Tetraacetylquinone methane compounds or their reduced forms are available via 1,4-benzoquinone and acetylacetone (J. Jenik, Chemicky prumysl 1985 35/60 1547, RJ Wikholm J. Org. Chem., 1985, 50, 382-4, E. Bernatek , S. Ramstad Acta Chem. Scand. 1953, 7, 1351-6).
  • Ditrifluoroacetamides can be prepared by means of trifluoroacetic acid via aromatic 1,4-diamines (R. Adams, J.M. Stewart J.A.C.S. 1952,20, 3660-4). By oxidation with Pb (rV) acetate, the diimine can be obtained.
  • suitable dopants are described for organic semiconductive materials, such as hole transport materials HT, which are commonly used in OLEDs or organic solar cells.
  • the semiconductive materials are preferably intrinsically hole-conducting.
  • the matrix material may be partially (> 10 or> 25 wt%) or substantially (> 50 wt% or> 75 wt%) or entirely composed of a metal phthalocyanine complex, a porphyrin complex, especially a metal porphyrin complex , an oligothiophene, oligophenyl, oligophenylenevinylene or oligofluorene compound, wherein the oligomer preferably comprises 2-500 or more, preferably 2-100 or 2-50 or 2-10 monomeric units.
  • the oligomer may also comprise>4,> 6 or> 10 or more monomeric units, in particular also for the ranges indicated above, ie for example 4 or 6-10 monomeric units, 6 or 10-100 monomeric units or 10-500 monomeric units ,
  • the monomers or oligomers may be substituted or unsubstituted, wherein block or copolymers may be present from said oligomers, a compound having a triarylamine unit or a spiro-bifluorene compound.
  • the matrix materials mentioned can also be present in combination with one another, if appropriate also in combination with other matrix materials.
  • the matrix materials may have electron donating substituents such as alkyl or alkoxy moieties which have reduced ionization energy or reduce the ionization energy of the matrix material.
  • the metal phthalocyanine complexes or porphyrin complexes used as the matrix material may have a main group metal atom or a subgroup metal atom.
  • the phthalocyanine complex or porphyrin complex may each be partially hydrogenated, but preferably the mesomeric ring system is not disturbed.
  • the same or different metal atoms or oxometal atoms may be present in the case of porphyrin complexes.
  • such dopable hole transport materials can be HT arylated benzidines, for example N, N'-perarylated benzidines or other diamines such as TPD (where one, more or all of the aryl groups may have aromatic heteroatoms), suitable arylated starburst compounds such as N, N ', N "-perarylated starburst compounds such as the compound TDATA (wherein one, more or all of the aryl groups may have aromatic heteroatoms)
  • the aryl radicals may in particular comprise phenyl, naphthyl, pyridine, quinoline, isoquinoline, peridazine, pyrimidine, pyrazine, pyrazole, imidazole, oxazole, furan, pyrrole, hidol or the like, for each of the abovementioned compounds
  • the phenyl groups of the respective compounds may be represented by thiophene groups partially or completely replaced.
  • the matrix material used consists entirely of a metal phthalocyanine complex, a porphyrin complex, a compound having a triarylamine unit or a spiro-bifluorene compound.
  • the doping may in particular be such that the molar ratio of matrix molecule to dopant or, in the case of oligomeric matrix materials, the ratio of matrix monomer number to dopant 1: 100000, preferably 1: 1 to 1: 10000, particularly preferably 1: 5 to 1: 1000, for example 1:10 to 1: 100, for example, about 1:50 to 1: 100 or even 1:25 to 1:50.
  • the doping of the respective matrix material (here preferably indicated as hole-conducting matrix material HT) with the dopants to be used according to the invention can be produced by one or a combination of the following processes:
  • the doping can be carried out in such a way that the dopant is evaporated out of a precursor compound which releases the dopant on heating and / or irradiation.
  • the Irradiation can be carried out by means of electromagnetic radiation, in particular visible light, UV light or IR light, for example, in each case laser light, or else by other types of radiation.
  • the irradiation can essentially provide the heat necessary for the evaporation, it can also be irradiated deliberately into specific bands of the compounds to be vaporized or precursors or compound complexes such as charge-transfer complexes in order, for example, to convert the compounds into excited states to facilitate by dissociation of the complexes. It is understood that the evaporation conditions described below are directed to those without irradiation and for comparison purposes uniform evaporation conditions are used.
  • Precursor compounds which can be used are, for example: a) mixtures or stoichiometric or mixed-crystalline compounds of the dopant and an inert, non-volatile substance, e.g. a polymer, molecular sieve, alumina, silica gel, oligomers or any other organic or inorganic substance having a high vaporization temperature, wherein the dopant is bound to this substance predominantly by van der Waals forces and / or hydrogen bonding.
  • an inert, non-volatile substance e.g. a polymer, molecular sieve, alumina, silica gel, oligomers or any other organic or inorganic substance having a high vaporization temperature, wherein the dopant is bound to this substance predominantly by van der Waals forces and / or hydrogen bonding.
  • the dopants according to the invention can be used for the production of organic light-emitting diodes (OLED), organic solar cells, organic diodes, in particular those with a high rectification ratio such as 10 3 -10 7 , preferably 10 4 -10 7 or 10 5 -10 7 or organic field effect transistors ,
  • OLED organic light-emitting diodes
  • the dopants according to the invention make it possible to improve the conductivity of the doped layers and / or to improve the charge carrier injection of contacts into the doped layer.
  • the component may have a pin structure or an inverse structure, without being limited thereto.
  • the use of the dopants according to the invention is not limited to the above-mentioned advantageous embodiments.

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  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne des dopants servant à doper un matériau matriciel semi-conducteur organique, une utilisation de ces dopants, un procédé de production desdits dopants, ainsi qu'un matériau matriciel semi-conducteur dopé, et un composant électronique produit au moyen dudit matériau matriciel semi-conducteur dopé.
PCT/DE2005/000189 2005-02-04 2005-02-04 Dopants pour semi-conducteurs organiques WO2006081780A1 (fr)

Priority Applications (2)

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JP2007553446A JP2008530773A (ja) 2005-02-04 2005-02-04 有機半導体への添加物
PCT/DE2005/000189 WO2006081780A1 (fr) 2005-02-04 2005-02-04 Dopants pour semi-conducteurs organiques

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EP4079743A1 (fr) 2021-04-23 2022-10-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
WO2023274452A1 (fr) 2021-06-30 2023-01-05 Heliatek Gmbh Procédé de fabrication d'au moins une couche de transport de charge dopée d'un système de couches d'un composant électronique organique
DE102021116886A1 (de) 2021-06-30 2023-01-05 Heliatek Gmbh Verfahren zur Herstellung mindestens einer dotierten Ladungstransportschicht eines Schichtsystems eines organischen elektronischen Bauelements
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4231804A2 (fr) 2022-02-16 2023-08-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362631A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4369898A1 (fr) 2022-10-27 2024-05-15 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4376583A2 (fr) 2022-10-27 2024-05-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362630A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362645A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4386065A1 (fr) 2022-12-14 2024-06-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

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