WO2006081780A1

WO2006081780A1 - Dopants for organic semiconductors

Info

Publication number: WO2006081780A1
Application number: PCT/DE2005/000189
Authority: WO
Inventors: Olaf Zeika; Horst Hartmann; Tatjana Wahl
Original assignee: Novaled Ag
Priority date: 2005-02-04
Filing date: 2005-02-04
Publication date: 2006-08-10
Also published as: JP2008530773A

Abstract

The invention relates to dopants for doping a semiconductor organic matrix material, to the use thereof, to a method for producing said dopants and an electronic component produced by means of said doped semiconductor organic matrix material.

Description

DOTANDEN FOR ORGANISM HOLDITER

description

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.

For some decades doping of silicon semiconductors has been state of the art. Thereafter, an increase in the initially low conductivity and, depending on the type of dopant used, a change in the Fermi level of the semiconductor is achieved by generating charge carriers in the material.

For some years now it has become known that 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. For doping electron donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyne (F4TCNQ) have become known. M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett, 73 (22), 3202-3204 (1998). and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998). These generate by electron transfer processes in electron donor-like base materials (hole transport materials) so-called. Holes, the number and mobility of which changes the conductivity of the base material more or less significantly. Examples of matrix materials with hole transport properties are N, N'-perarylated Benzidine TPD or N, N ', N "-perarylated starburst compounds, such as the substance TDATA, or else certain metal phthalocyanines, in particular zinc phthalocyanine ZnPc known.

However, 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. Furthermore, there are disadvantages in the use of previously known 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. At the same time, however, it should be noted that 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.

According to the invention, this object is achieved by a dopant according to claim 1, wherein preferred embodiments result from the subclaims. Surprisingly, 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. In particular, 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.

It is understood that the compounds of the invention are preferably such that they evaporate more or less or virtually undecomposed. However, under certain circumstances, it is also possible to use precursors as dopant source in a targeted manner which release the compounds used according to the invention, for example acid addition salts. for example, a volatile or nonvolatile inorganic or organic acid, or charge-transfer complexes thereof, wherein the acids or electron donors are preferably not or only slightly volatile or the charge-transfer complex itself acts as a dopant.

Preferably, 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.

Preferably, 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. Furthermore, the charge carrier injection of contacts into the doped layer can be improved by the dopants according to the invention. Furthermore, 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. Further, 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.

Representation of the dopants

Of essential importance for the preparation of the dopants according to the invention are the dihydroquinone derivatives as synthetic precursors of the quinoid structures 40-48, which have the following structures:

47a 48a The substituents A, B, C and D may have the following meaning:

N

NC ^ CN NCT ^ CF ₃ N OH O

S1 S14 S11 S12a S12

Substituent S 12 is particularly suitable for structures 47a and 48a.

Representation possibilities of the dopants on the basis of quinone derivatives are as follows:

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).

1,3-indandione compounds were synthesized by V. Khodorkovsky at al ^ V. Khodorkovsky at al Tetrahedron Lett. 1999, 40, 4851-4)

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. 1985, 120, 309-14 ), wherein the 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). Furthermore, 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).

It was also possible from 1,4-dihalogenated Pd-catalyzed malodinitrile anion and subsequent oxidation Tetracyanochinondimethane represent (S. Takahashi al., Tetrahedron Letters, 1985, 26, 1553).

Chinoids 1,4-polyphenylenes E.A. Shalom, J.Y. Becker, I., Agranat, Nouveau Journal de Chimie 1979, 3, 643-5.

Heteroannelated quinones were synthesized via a multistep synthetic route. Bib, P. Dickmann, HF Herrmann, Z. Naturforsch., 1991, 46b, 326-8, J. Druey, P. Schmidt, (B. HeIv. Chim. Acta 1950, 140, 1080-7)

Bridged quinoidal compounds are presented by M. Matsuoka, H. Oka, T. Kitao, Chemistry Letters, 1990, 2061-4; J. Dieckmann, WR Hertier, RE Benson, JACS 1963, 28, 2719-24; K. Takahashi, S. Tarutani, JCS Chem. Comm. 1994, 519-20; NN Voroshzov, WA Barchash, Dokady Akad. SSSR 1966, 166/3, 598. Annealed TCNQ compounds are presented by M. Matsuoka, H. Oka, T. Kitao, Chemistry Letters, 1990, 2061-4; BS Ong, B. Koeshkerian, J. Org. Chem. 1984, 495002-3.

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.

Chinoids Structures with different X, Y residues have been synthesized in various circles (T. Itoh, N. Tanaka, S. Iwatsuki, Macromolecules 1995, 28, 421-4; JA Hyatt, J. Org. Chem. 1983, 48 129-31 1992, 57, 1690-6; A. Schoenberg, E. Singer, Chem. Ber. 1970, 103, 3871-4, S. Iwatsuki, T. Itoh, H., J. Org. Chem. Itoh Chemistry Letters, 1988, 1187-90; T. Itoh, K. Fujikawa, M. Kubo, J. Org. Chem. 1996, 61, 8329-31; Iwatsuki, T. Itoh, T. Sato, T. Higuchi, Macromolecules, 1987, 20, 2651-4; T. Itoh et al. Macromolecule 2000, 33, 269-77; BS Ong, B. Koeshkerian, J. Org. Chem. 1984, 495002-3; H. Junek, H. Hamböck, B. Hornischer, Mh.Chem.1967, 98, 315-23; PW Pastors et al Doldady Akad. SSSR 1972, 204, 874-5; AR Katritzky et al Heterocyclic Chem. 1989, 26, 1541-5; NN Vorozhtsov, VA Barkash, SA Anichkina, Doldady Akad. SSSR 1966, 166, 598).

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.

Other diimide or amide structures were prepared by B.C. McKusick et al., J.A.C.S., 1958, 80, 2806-15.

matrix materials

In the present invention, 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. Optionally, 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 metal atom Me may in each case be coordinated 4-, 5- or 6-fold, for example in the form of oxo (Me = O), dioxo (O = Me = O), imine, diimine, hydroxo, dihydroxy. , Amino or diamino complexes, without being limited thereto. The phthalocyanine complex or porphyrin complex may each be partially hydrogenated, but preferably the mesomeric ring system is not disturbed. The phthalocyanine complexes may contain, for example, magnesium, zinc, iron, nickel, cobalt, magnesium, copper or vanadyl (= VO) as the central atom. The same or different metal atoms or oxometal atoms may be present in the case of porphyrin complexes.

In particular, 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.

TPD TDATA ZnPc

Preferably, 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.

It is understood that suitable other organic matrix materials, in particular hole-conducting materials can be used which have semiconducting properties.

endowment 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.

Evaporation of the dopants

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:

a) Mixed evaporation in vacuo with a source of HT and one for the dopant.

b) Sequential deposition of HT and dopant with subsequent diffusion of the dopant by thermal treatment

c) doping of an HT layer by a solution of dopants with subsequent evaporation of the solvent by thermal treatment

d) Surface doping of an HT layer by a superficially applied layer of dopants

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.

b) Mixture or stoichiometric or mixed crystalline compound of the dopant and a more or less Elelctronendonor-like, non-volatile compound V, wherein a more or less complete charge transfer between the dopant and the compound V occurs, as in charge-transfer complexes with more or less electron-rich polyaromatic or heteroaromatic or other organic or inorganic high-vapor-phase substance.

c) mixture or stoichiometric or mixed crystalline compound of the dopant and a substance which evaporates together with the dopant and has an ionization energy equal to or higher than the substance to be doped HT, so that the substance in the organic matrix material does not form a trap for holes. This may be the substance According to the invention also be identical to the matrix material, for example, represent a metal phthalocyanine or benzidine derivative. Other suitable volatile co-substances, such as hydroquinones, 1,4-phenylenediamines or 1-amino-4-hydroxybenze or other compounds form quinhydrones or other charge-transfer complexes.

Electronic component

Using the organic compounds according to the invention for producing doped organic semiconducting materials, which may be arranged in particular in the form of layers or electrical conduction paths, a multiplicity of electronic components or devices containing them can be produced. In particular, 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 , 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. Particularly in the case of OLEDs, the component may have a pin structure or an inverse structure, without being limited thereto. However, the use of the dopants according to the invention is not limited to the above-mentioned advantageous embodiments.

The features of the invention disclosed in the foregoing description and in the claims may be essential both individually and in any combination for the realization of the invention in its various embodiments.

Claims

claims

1. dopant for doping an organic semiconductive matrix material, characterized in that the dopant is selected from the group of organic, quinoid, mesomeric compounds having one of the following basic skeletons:

40 41 42 43

47 48 wherein in backbone (40) R] -R _{4 is} independently Cl, CN, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen, wherein A and B are selected off

N

I l

NC ^ CN NC ^ CF ₃ N

S1 S14 S11

wherein in structure _t (41) R - R ₈ is independently Cl, F, CN, _NO2, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl one or ¹ more substituents selected from CN, NO _2, NO, perfluoroalkyl, SO ₃ R and / or halogen have;

wherein in structure (42) R ₁ -R _{6 is} independently Cl, F, CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen, wherein A and B are selected from the group consisting of

N

I l

NC ^ CN NC ^ CF ₃ N

S1 S14 S11

wherein in structure (43) R, -R _{8 is} independently Cl, F, perfluoroalkyl, CN, NO ₂ , NO, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen, wherein A and B are selected from the group consisting of N

NCΓ CN NC XF ₃ N

S1 S14 S11

wherein in structure (44) R 1 -R _{6 is} independently Cl, F, CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and or halogen;

wherein in structure (45) R 1 -R _{4 is} independently Cl, F, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or Have halogen;

wherein in structure (46) R ₁ -R _{6 is} independently Cl, F, CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen;

wherein in structure (47) R] -Ri _{2 is} independently Cl, F, CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen; or wherein Ri, R ₃ , R ₉ and R] _{2 are} hydrogen and R ₂ , R ₄ - R ₈ , R ₁ and R n are independently Cl, F, CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and Heteroaryl one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or halogen;

wherein in structure (48) Ri-Ri _{2 is} independently Cl, F ₅ CN, NO ₂ , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from CN, NO ₂ , perfluoroalkyl, SO ₃ R and / or have halogen, wherein the dopant under the same evaporation conditions has a lower volatility than tetrafluorotetracyanoquinone dimefan (F ₄ TCNQ).

2. Dotand according to claim 1, characterized in that the substituents A, B, C and D in structures (41) and (43) to (48) are the same or different and are selected from the group consisting of:

N

NC CN NC ^ CF ₃ NO

S1 S14 S11 S12

3. Dotand according to claim 1 or 2, characterized in that perfluoroalkyl CF ₃ and halogen is fluorine or chlorine.

4. Dotand according to one of the preceding claims, characterized in that the dopant represents a quinoid system with a quinoid ring and one, two or three fused aromatic rings.

5. Dotand according to claim 4, characterized in that the aromatic rings have one or more heteroatom (s).

6. Use of a dopant according to any one of claims 1 to 5 for the doping of an organic semiconductive matrix material for changing the electrical properties thereof.

7: Use according to claim 6, characterized in that the matrix material is hole-conducting.

8. Use according to claim 6 or 7, characterized in that the matrix material consists partially or completely of a metal phthalocyanine complex, a Poiphyrin complex, an oligothiophene compound, Oligophenylverbindung, Oligophenylenlvinylenverbindung, Oligofluoren- connection, a Pentazenverbindung, a compound with a triarylamine Unit and / or a spiro-bifluorene compound.

9. Use according to one of claims 6 to 8, characterized in that the molar doping ratio of dopant to matrix molecule or monomeric unit of a polymeric matrix molecule between 1: 1 and 1: 10,000.

10. An organic semiconductive material containing an organic matrix molecule and an organic dopant according to any one of claims 1 to 5.

11. Organic semiconductive material according to claim 10, characterized in that the molar doping ratio of dopant to matrix molecule or monomeric unit of a polymeric matrix molecule between 1: 1 and 1: 10,000.

12. Electronic component with an organic semiconducting material, which is doped with an organic dopant for changing the electronic property of the semiconducting matrix material according to one of claims' 1 to 5.

13. Electronic component after! Claim 12 in the form of an organic light-emitting diode (OLED), a photovoltaic cell, a. organic

Solar cell, an organic diode or an organic field effect transistor.