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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/06—Phosphorus compounds without P—C bonds
  • C07F9/062—Organo-phosphoranes without P-C bonds
  • C07F9/065—Phosphoranes containing the structure P=N-
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
  • C07F9/572—Five-membered rings
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
  • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
  • C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
  • C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
  • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
  • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
  • C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
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  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/24—Electrically-conducting paints
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  • 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
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  • H10K71/30—Doping active layers, e.g. electron transporting layers
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  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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  • 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
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• • 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

Definitions

• the present invention relates to an n-dopant for doping organic electron transport materials, wherein the n-dopant at least one aminophosphazene group according to formula 1
• suitable electrically conducting organic materials has thereby enforced in the art that additional substances are ⁇ introduced into the layers, which cause the intrinsic Leitfä ⁇ ability of these materials is increased.
• additional substances are ⁇ introduced into the layers, which cause the intrinsic Leitfä ⁇ ability of these materials is increased.
• p- or n-dopants which are each because the p- or n-conductivity of transport / contact layers improves.
• the number of available n-dopants for these organic electronic devices is very limited, the design possibilities and current technical performance of organic devices limi ⁇ advantage. Therefore, in addition to the use of suitable dopants in OLEDs, the use of these in field effect transistors as a contact doping, especially in complementary circuits or in bipolar devices of great importance.
• a light-emitting layer composed of at least ei ⁇ nem matrix material and at least one emitter material where ⁇ at the at least one matrix material, at least one cyclic see phosphazene compound, the use of cyclic phosphazene compounds in organic light emitting diodes and a device selected from the group consisting of stationary screens, mobile screens and lighting units containing at least one organic light emitting diode according to the invention and selected cyclic phosphazene ⁇ compounds and processes for their preparation.
• A B , or B 3 in which - Ar is a C 6 -C 18 -arylene which may be mononuclear or polynuclear and may optionally be substituted by one or more C 1 -C 10 -alkyl or C 3 -C 10 -cycloalkyl groups, - Ar 2 is a C 6 -C 18 arene skeleton, which is optionally substituted with elektronenab ⁇ emitting groups R 4 - B 1 and B 2 are independently selected from B and Ar 2, B 3 is independently selected from the same group as B, - R 1, R 2 , R 3 are independently selected from alkyl, arylalkyl, cycloalkyl, aryl, dialkylamino, -X is selected from 0, 1, 2 and 3, where for x> 1 each Ar 1 may be different, - y is a non-zero whole Number up to the total number of valence sites on the arene skeleton, z an integer from zero to the total number of
• it is the object of this invention ⁇ provide a method by which are n-transport layers are available which have an improved conductivity, and the provision of electrical components comprising organic these transport layers.
• the n-type dopant is characterized for doping organic ⁇ shear electron transport materials in that the n-dopant at least one aminophosphazene group according to formula 1
• Formula 1 are able to increase the Elektronenleitfä ⁇ ability of organic electron transport materials significantly. This effect is not recirculate to the trinsische in ⁇ conductivity of the n-type dopant to-the invention, but is due to the interaction of the n-dopants according to the invention with an electron-transfer material port. This significant increase in conductivity can be obtained both with substances which, as functional units have only aminophosphazene groups as well as with substances in which the aminophosphazene group represents only one part of the functional groups of the molecule.
• Ronen transport material ETM
• ETM Ronen transport material
• structure A This includes new frontier orbitals (HOMO or SOMO and LUMO) whose ener ⁇ Getic layers hopping good interaction (for example, an electron from the "Charge -Transfer complex "on a matrix molecule ⁇ molecule) with undoped matrix molecules allows, whereby an increased conductivity is achieved.
• HOMO or SOMO and LUMO new frontier orbitals
• ener ⁇ Getic layers hopping good interaction for example, an electron from the "Charge -Transfer complex "on a matrix molecule ⁇ molecule
• undoped matrix molecules allows, whereby an increased conductivity is achieved.
• structure B by transferring an entire charge from the dopant to the matrix, an increase in their electron density and thus also their conductivity can occur.
• the ETM molecule can also dissociate again from the dopant, whereby a radical anion of the matrix and a radical cation of the phosphazene dopant form (structure C). Due to the special structure of the aminophosphazene group, a resonance-stabilized compound is obtained, which can be responsible for the fast kinetics and good doping.
• aminophosphazene group in the context of the invention is understood as meaning a compound which has at least one
• Aminophosphazene group according to the formula 1 in the molecule This may be an uncharged molecule or else a salt compound which has ions, where at least one ion comprises an aminophosphazene group.
• Sig nificantly ⁇ for aminophosphazene group is the connection of 4 nitrogens on the central phosphorus atom.
• This central unit can be repeated in the dopant and, in addition, several amino phosphazene groups can be linked to one another in a linear or cyclic manner.
• the dopant according to the invention in addition to the aminophosphazene units also has other functional groups.
• the substances having at least one aminophosphazene group are used as n-dopant.
• This loading indicated in particular that it is not according to the invention, that these substances are used alone within a layer or in a ⁇ ganisch electronic component. This is not because the basic conductivity of this class of se for effective organic electronic components is unzurei ⁇ accordingly.
• This dopant is thus intended to interact with an electron transport material.
• apparently the HOMO level of the ER inventive n-dopants are formed so that the ⁇ se effective port materials with the LUMO level of the electron-transfer standard can interact.
• Dopant in this context is thus understood to mean a substance which is deposited together with the electron transport material, in accordance with a production process known to those skilled in the art.
• the molar fraction of the n-dopant in the layer is not above the molar fraction of the electron-transporting material.
• the concentration of the n-dopant according to the invention in a layer is significantly lower than that of the electron-transport material.
• modern ⁇ n-type dopant also shows as a single substance in a layer deposited lien a significantly lower electrical conductivity than layers of Elektronentransportmateria-.
• n-dopant results from the fact that the n-dopants according to the invention act as blocking material in p-type layers. This also in contrast to electron transport materials.
• n-dopant may correspond to the following formula 2,
• R 1 to R 4 are independently selected from the group of R comprising a bond, H, D, C 1 -C 60 saturated or unsaturated alkyl, cycloalkyl, heteroalkyl, heteroalkyl, cycloalkyl; C1-C60 aryl, alkylaryl, heteroaryl; and
• N-type dopants with the above substitution pattern have been found to be particularly suitable for the doping of electron transport materials. Without being bound by theory, this can be attributed to the fact that the specified substituents significantly increase the basicity of the compound, resulting in improved doping in connection with electron transport materials.
• the given results of the aminophosphazene ⁇ substitution group to the fact that a sterically suitable molecule is obtained, which both can be processed well in wet and dry processes, and subsequently in conjunction with the electron transport material ⁇ lien little tendency to crystallize.
• these annular structures can contribute to the fact that charges occurring in the context of doping can be distributed over the entire inner rings. This can contribute to a particularly stable and effective doping.
• the substituents R 1 -R 4 may be selected independently from the group R x comprising a bond, C 1 -C 20 -substituted or unsubstituted alkyl, cycloalkyl;
• the molar concentration of n-dopant can be 25%, preferably 1% ⁇ and ⁇ is 20% in a layer ⁇ ⁇ 0.1%.
• the quantitative determination of the mo ⁇ laren proportions of substances within a layer is known in the art.
• the layers can dissolved and by means of common quantitative Festungsme ⁇ methods, such as HPLC, are determined.
• the number of aminophosphazene groups in the dopant may be ⁇ 2 and -S 7. Because of the basicity of the invention insertion ⁇ cash aminophosphazene groups and based thereon interaction with the electron transport material, it may be advantageous that the dopant used carries a higher number of aminophosphazene groups. Without being bound by theory, the dopant is thereby able to interact with several molecules of the matrix material or, if necessary to transmit multiple charges to the matrix mate rial ⁇ . This can contribute to an increase in the conductivity of the layer. Furthermore, it can be achieved by the interactions with several matrix molecules that the crystallization tendency of the layer decreases. This may contribute to extended shelf life of devices having these layers.
• the dopant may be a compound having non-cyclic aminophosphazene backbone.
• the linear dopants which Minim ⁇ least have a aminophosphazene-group have been found suitable for doping of organic electron transporting materials to be particularly suitable. Without being bound by theory, this can most likely be attributed to the fact that the steric properties of this substance class allow a particularly close approximation to the electron transport materials, which can then subsequently lead to a very fast and efficient charge transfer.
• the linear geometry of the n-dopants can lead to an increased lifetime of organic components containing this class of substance being achieved due to the reduced tendency to crystallize.
• the dopant may comprise at least one compound of the following formulas 3-28:
• the compounds of the formulas 3-28 are particularly suitable for the doping of conventional electron transport materials.
• the substituent pattern of doping is to provide materials capable of compounds that work over both wet and dry processes also read ⁇ sen.
• the spatial properties of the chosen substituents also seem to be very suitable to form layers together with organic electron transport materials, which are characterized by particularly low crystallization tendency. This can lead to a longer lifetime of organic electronic components.
• an n-dopant wherein ⁇ 1 and -S 4 substituents of R 1 - R 4 and R 6 tert-butyl
• Substituents are.
• the Aminophosphazen- compounds in which tertiary-butyl groups are bonded to the nitrogen are characterized by a particularly good doping effect. Without being bound by theory, this may be due to the fact that the tertiposed- butyl groups have both appropriate inductive properties as well as an appropriate steric configuration which is capable of both the basicity of the compound to be raised stabili ⁇ hen as well as a simple Access of matrix materials to allow the dopant. A higher number of tertiae ⁇ ren butyl groups may be less advantageous, as in this case, an entry of the matrix material can be difficult.
• the dopant may have a cyclic structure having two to four ver ⁇ knüpften aminophosphazene units.
• the cyclic structures of the aminophosphazenes may be able to achieve a particularly effective doping of electron transport materials. This is most likely due to the fact that the basicity of the compound is increased by cyclic arrangement. Furthermore, the charges occurring after the doping can be distributed effectively over the entire ring system.
• a 4-membered ring is formed when linking 2 units, a 6-membered ring when linking 3 units, and an 8-membered ring when 4 units are linked. This ring size also allows a good processing of the compounds both in wet processes as well as in the vacuum deposition.
• larger ring skeletons may be disadvantageous, since in these cases effective evaporation of the substances may be hindered.
• At least one of the substituents on each ring can not a nitrogen via a carbon-linked C1-C60 alkyl, cycloalkyl, aryl or heteroaryl to be, with the individual Substi ⁇ tuenten may be joined together.
• the substitution of the non-ring nitrogens by the above substitution pattern has made possible a particularly suitable increase in the basicity of the aminophosphazene compounds without causing a negative impact on the kinetics of a later reaction with electron transport materials. For this reason, it is therefore advantageous that at least a sub ⁇ substituents is open to the non-ring nitrogens with a substituent of the above.
• each of the substituents on each non-ring nitrogen may be a C1-C30 alkyl, cycloalkyl, aryl, or heteroaryl group attached via a carbon, wherein the individual substituents may be linked together.
• substituents due to the electronic properties of the abovementioned substituents arise, probably due to the inductive effects, particularly effective n-type dopants.
• the short- to medium-chain alkyl and aryl compounds appear to be particularly suitable for this purpose. These compounds can be easily processed in both wet and vacuum processes and provide long-term stable doped layers.
• the dopant can 29-35 hold at least one of the following formulas to ⁇ :
• the cyclic compounds of the formulas 29-35 appear to be particularly suitable for the n-doping of electron transport layers owing to their steric configuration and the electrical properties predetermined by the substituent pattern.
• the molecular mass of these compounds it ⁇ enables also a good processing in vacuum processes.
• a method for producing n-type organic electrical layers wherein the organic n-type dopant is deposited together with an organic electron transport material within a layer and the n-type dopant and the electron transport material are brought to Re ⁇ action.
• this can bring about the reaction according to the reaction mechanism specified above. It can therefore only an electrostatic interaction of the OF INVENTION ⁇ n-dopants to the invention with the electron transport material take place, which subsequently a transfer of
• Electrons can lead to the electron transport material. This can bring about the reaction due to a suitable reaction kinetics automatically by the simultaneous deposition in a layer. Depending on the electron transport material and inserted n-dopant which bring to re ⁇ action can also be done through a subsequent thermal excitation.
• the common electron transport materials can be used, which are familiar to those skilled in the field of organic electronics. The deposition of both materials can be achieved both from the wet phase as well as by a vacuum process.
• Aminophosphazene acts as an n-dopant and can exhibit its doping effect either by coevaporation with an electron transport material or by mixing an aminophosphazene with an ETM and subsequent liquid processing (e.g., spin coating, inkjet printing, slot coating, etc.). Due to the good solubility even in very non-polar solvents, the aminophosphazene bases are very well suited for liquid processing.
• the larger molecules e.g., a P4 base
• the organic electron transport material may be selected from the group comprising 2, 2 ', 2 "- (1, 3, 5-benzene triyl) tris (1-phenyl-1H-benzimidazoles), 2- (4- Biphenylyl) -5- (4-tert-butylphenyl) -1, 3, 4-oxadiazoles; 2, 9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 8-hydroxyquinolinolato-lithium; 4- (Naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazoles; 1,3-bis [2- (2,2'-bipyridine-6-yl) -1,3,4 -oxadiazo-5-yl] -benzenes; 4,7-diphenyl-1,10-phenanthroline (BPhen); 3- (4-biphenylyl) -4-phenyl-5-tert-butylphenyl-1,
• these electron transport materials can be reacted well with the aminophosphazene dopants according to the invention.
• the additional doping of the aminophosphazenes in particular, significantly increases the conductivity of the electron transport materials.
• an n-type organic electrical layer which was prepared by the process according to the invention.
• the above-presented procedural ⁇ ren particularly homogeneous layers can be obtained which are suitable for use in devices of organic electronics.
• insbesonde ⁇ re suitable Aminophosphazene the invention to be processed using the standard procedures of organic electronics.
• the layers produced in this way are characterized in that they have a low crystallization tendency , which contributes to a longer service life of organic components containing these layers.
• the increased conductivity of the electron transport layers also leads to a higher efficiency of the layers.
• an organically electric Bauele ⁇ element wherein the device comprises an n-type organic layer electric invention.
• the n-dopants according to the invention and the method according to the invention for producing doped electron-transport layers can be used particularly well for the production of organic electrical components. This way, durable, efficient components will be preserved.
• the organic electrical components may include the standard components of the organic electrical ⁇ nik, namely organic photodiodes, solar cells, Bipolar and field effect transistors and organic light-emitting diodes.
• the LED is constructed of a
• FIG. 2 shows schematically the structure of an organic solar cell with PIN structure (20), which converts light (21) in electric ⁇ electric current.
• the solar cell consists of a layer of indium tin oxide (22); a p-doped layer (23); an absorption layer (24); an n-doped layer (25) and a metal layer (26);
• Substrate (31) is a gate electrode (32), a Ga ⁇ te dielectric (33), a source and drain contact (34 + 35) and an organic semiconductor (36) applied.
• the hatched areas show the places where a contact doping is helpful.
• FIG. 4 shows an IV characteristic of an electron-conducting matrix material (ETM036, Merck) which has been doped with an n-dopant (P4-tBu) according to the invention.
• ETM036, Merck electron-conducting matrix material
• P4-tBu n-dopant
• FIG. 5 shows an IV characteristic of a further electron-conducting matrix material (ETM019, Merck) which has been doped with an n-dopant (P4-tBu) according to the invention.
• ETM019, Merck electron-conducting matrix material
• P4-tBu n-dopant
• FIG. 6 shows an IV characteristic of a further electron-conducting matrix material (TMM004, Merck) which has been doped with an n-dopant (P4-tBu) according to the invention. The characteristics are discussed in the examples.
• 7 shows an IV characteristic of a further electron-conducting matrix material (Alq3, aluminum tris (8-hydroxyquinoline)), which is provided with a erfindungsge- n-dopants (P4-tBu) was doped.
• the characteristic ⁇ lines are discussed in the examples.
• n-dopants are shown by the doping of different organic electron conductors.
• the n-dopant is the aminophosphazene base P4 ⁇ t Bu
• the phosphazene base P 4 - Bu is available commercially from Sigma-Aldrich as a 0.8 M solution in n-hexane.
• the solution (1 mL) was placed in a glove box to a Schlenk tube and concentrated with ⁇ means of vacuum to dryness.
• the white residue was then sublimed three times at 105 ° C. in a high vacuum (3-4 ⁇ 10 ⁇ 6 mbar).
• the product was obtained in 73% yield as a white, partially crystalline solid.
• ITO indium tin oxide
• the layer thickness fraction (volume%) of dopant in cases 1 to 3 is 18%, whereas in the doping of Alq3 17% dopant was used.
• FIGS. 4-7 The comparison of the doped electron-conducting matrix materials with the undoped matrix materials is shown in FIGS. 4-7.
• FIG. 4 shows the current-voltage characteristic curve for the doping of ETM-036,
• FIG. 5 shows the doping of ETM-019,
• FIG. 06 shows the doping of TMM-004 and
• FIG. 7 shows the doping of Alq3 in each case with P 4 -t Bu ,

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