ELECTRONIC DEVICES

Description

[0001] The present application relates to an electronic device comprising an anode, a cathode, at least one emitting layer between the anode and the cathode, at least one p-doped layer A containing a mono-triarylamine as a host, and at least one layer B containing a mono-triarylamine, and a p-doped layer A' containing a triarylamine, wherein the following layer structure is present between the anode and the light-emitting layer, and wherein the layers are directly adjacent to one another: Anode Layer A' Layer A Layer B Emitting layer, and wherein the monotriarylamine is selected as defined below in the claims. In particular, the invention relates to an organic electroluminescent device (OLED) comprising the above-mentioned layer structure.

[0002] Electronic devices containing organic layers are currently the subject of intensive research. Of particular interest are organic electroluminescent devices, which are used, for example, in displays of mobile electronic devices or as lighting elements.

[0003] Known in the prior art, e.g. in EP 1463130 A2 and DE 102007031220 A1, are electronic devices comprising one or more p-doped layers containing a dopant and a host material, wherein the host material may be an organic nitrogen compound.

[0004] Furthermore, it is known, for example from US 5093698 A, that by doping hole or electron transport layers in electronic devices, their conductivity can be significantly increased.

[0005] Also known in the prior art are electronic devices containing mono-triarylamines as materials for the hole-transporting or emitting layer, for example from EP 1885008 A1 and JP 1995053955 A.

[0006] Furthermore, electronic devices containing both p-doped hole transport layers and undoped hole transport layers are known from EP 2365555 A2.

[0007] Of utmost importance in the development of new electronic devices are the long-term stability of the devices and their performance characteristics, particularly operating voltage and efficiency. Although progress has been made, there is still room for improvement in all of these areas compared to the prior art designs.

[0008] The technical object of the present invention is to provide an electronic device which has better properties in one or more of the above-mentioned points of long-term stability and performance data than the devices known in the prior art.

[0009] The technical problem is solved by the following objects of the invention.

[0010] A p-doped layer is defined as a layer in which free holes have been created, thereby increasing its conductivity. A comprehensive discussion of doped transport layers in OLEDs or organic solar cells can be found in Chem. Rev. 2007, 107, 1233.

[0011] A monotriarylamine is a compound containing a single triarylamine group. A triarylamine group is a group in which three aryl or heteroaryl groups are bonded to a nitrogen atom. The monotriarylamine preferably contains no further arylamino group. The monotriarylamine particularly preferably contains no further amino group.

[0012] Furthermore, layer A, layer B and the emitting layer preferably represent organic layers, ie layers which essentially consist of one or more organic compounds.

[0013] <h2 style=";text-align:left;direction:ltr">In In an embodiment not according to the claims, there is a device which has the following layer sequence between the anode and the emitting layer, the layers being directly adjacent to one another: Anode layer A layer B emitting layer.

[0014] This embodiment not according to the invention corresponds to the<h2 style=";text-align:left;direction:ltr"> Fig. 1 depicted structure of the electronic device (1), wherein anode (2), layer A (3), layer B (4), emitting layer (5), electron transport layer (6) and cathode (7) follow one another and are directly adjacent to one another.

[0015] Preferably, an electron injection layer (6a) is further provided between the electron transport layer (6) and the cathode (7), as in <h2 style=";text-align:left;direction:ltr"> Fig. 2 , also not according to the claim.

[0016] <h2 style=";text-align:left;direction:ltr"> In In a further embodiment of the invention not according to the claims, a further layer C is present between layer B and the emitting layer. A possible layer arrangement of the electronic device (1) according to this embodiment is shown in <h2 style=";text-align:left;direction:ltr"> Fig. 3 shown, with layer C (4a).

[0017] Layer C preferably contains an organic amine, more preferably a triarylamine, and most preferably a mono-triarylamine, as defined above.

[0018] Preferably, layer C directly adjoins the emitting layer.

[0019] According to the claim, layer B, which contains a mono-triarylamine, is directly adjacent to the emitting layer.

[0020] According to the claim, between the anode and the p-doped layer A, which contains a mono-triarylamine, there is a p-doped layer A', which contains a triarylamine, so that the following layer structure results between

[0021] Anode and emitting layer, with the layers directly adjacent to each other: Anode Layer A' Layer A Layer B emitting layer, and wherein the mono-triarylamine is selected as defined below in the claim.

[0022] A possible layer arrangement of the electronic device (1) according to this embodiment of the invention is shown in <h2 style=";text-align:left;direction:ltr"> Fig. 4 shown, with layer A' (2a).

[0023] Layer A' contains a triarylamine, for example a mono-triarylamine, a bis-triarylamine, or a compound with more than two triarylamine groups. Layer A' is p-doped. It preferably contains an organic electron-accepting compound as a dopant. Preferred embodiments of such dopants are listed in a following section.

[0024] In general, the electronic device may also contain further layers, for example, additional hole-transport layers, electron-transport layers, coupling-out layers, interlayers, hole-blocking layers, electron-blocking layers, exciton-blocking layers, charge-generation layers, and / or organic or inorganic p / n junctions. The preferred arrangement, function, and combination of such layers is known to those skilled in the art.

[0025] It is generally preferred that the layers between the anode and the emitting layer all contain at least one monotriarylamine. More preferably, they contain no triarylamine compounds other than monotriarylamines. Most preferably, one or more monotriarylamines are present identically in all layers between the anode and the emitting layer.

[0026] The p-doped layer A preferably has a thickness of 1 to 500 nm, particularly preferably of 5 to 300 nm and most preferably of 8 to 250 nm.

[0027] The p-doped layer A preferably contains a dopant that is an electron acceptor compound. Particularly preferably, the dopant is capable of oxidizing the monotriarylamine, i.e., it has a sufficiently high redox potential, in particular a higher redox potential than the monotriarylamine.

[0028] According to a preferred embodiment, the dopant has a LUMO that is no higher than 0.3 eV above the HOMO of the mono-triarylamine, preferably no higher than 0.2 eV, and more preferably no higher than 0.1 eV. Most preferably, the dopant has a LUMO that is equal to or lower than the HOMO of the mono-triarylamine.

[0029] In the present application, HOMO and LUMO positions are determined by quantum chemical calculations with "Gaussian03W" (Gaussian Inc.), as explicitly stated in the working examples.

[0030] Preferably, the dopant has a LUMO that is less than -4.6 eV, more preferably less than -4.8 eV, and most preferably less than -5.0 eV. Most preferably, the dopant has a LUMO that is less than -5.1 eV.

[0031] In principle, all compounds that are electron-accepting compounds and can increase the conductivity of the organic layer by oxidizing the host are suitable as dopants. A person skilled in the art can identify suitable compounds without great effort within the scope of their general technical knowledge.

[0032] Particularly suitable as dopants are those described in WO 2011 / 073149, Compounds disclosed in EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO 2009 / 003455, WO 2010 / 094378, WO 2011 / 120709, US 2010 / 0096600 and WO 2012 / 095143.

[0033] The dopant of the p-doped layer A is preferably selected from quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I 2 , metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of the 3rd main group, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as a binding site.

[0034] Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re 2 O 7 , MoOs, WO 3 and ReO 3 .

[0035] Furthermore, organic compounds with electron acceptor properties are preferred as dopants, in particular the following compounds: (D-1) (D-2) (D-3) (D-4) (D-5) (D-6) (D-7) (D-8) (D-9) (D-10) (D-11) (D-12)

[0036] The dopant is preferably present in layer A in a concentration of 0.1 to 20 vol%, preferably 0.5 to 12 vol%, particularly preferably 1 to 8 vol% and very particularly preferably 2 to 6 vol%.

[0037] In addition to the dopant and the mono-triarylamine, the p-doped layer A may contain further compounds, for example further dopants and / or further compounds with hole-transporting properties.

[0038] According to a preferred embodiment, the p-doped layer has a conductivity of more than 10 -8< S / cm, more preferably more than 10 -7< S / cm, most preferably more than 10 -6< S / cm and most preferably more than 10 -5< S / cm.

[0039] The conductivity of thin films can be measured using the two-point method. Contacts made of a conductive material, such as gold or indium tin oxide, are applied to a substrate. The thin film to be examined is then applied over a large area of ​​the substrate so that the contacts are covered by the film. After a voltage is applied to the contacts, the current flowing is measured. The conductivity of the film is determined from the resistance determined from the geometry of the contacts and the film thickness of the sample. Such measurements on doped organic films are described, for example, in EP 1786050 A1. Alternatively, the four-point method can be used to determine conductivity, as described in van der Pauw et al., Philips Technical Review, 1959 / 1960, Vol. 20, 220 and van der Pauw et al., Philips Research Reports 1958, Vol. 13, 1.

[0040] According to a preferred embodiment, the same mono-triarylamine is present in layer A and in layer B.

[0041] According to a further embodiment not according to the invention, the same mono-triarylamine is present in layer B and in layer C.

[0042] According to a further embodiment not according to the invention, the same mono-triarylamine is present in layer A and in layer C.

[0043] According to a further embodiment not according to the invention, the same mono-triarylamine is present in layer A, in layer B and in layer C.

[0044] A mono-triarylamine not according to the invention is a compound of formula (I) where: Ar 1< is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; R 1< is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, C(=O)R 2< , P(=O)(R 2< ) 2 , S(=O)R 2< , S(=O) 2 R 2< , CR 2< =CR 2< R 2< , CN, NO 2 , Si(R 2< ) 3 , OSO 2 R 2< , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is substituted by one or more radicals R 2< may be substituted, where one or more non-adjacent CH 2 groups are substituted by R 2< C=CR 2< , C≡C , Si(R 2< ) 2 , Ge(R 2< ) 2 , Sn(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , P(=O)(R 2< ), SO, SO 2 , NR 2< , O,S or CONR 2< and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or a combination of these systems; two or more adjacent substituents R 1< can also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and R 2< is, on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which H atoms can also be replaced by D or F; two or more adjacent substituents R 2< can also form a mono- or polycyclic,form an aliphatic or aromatic ring system. According to the claim, the mono-triarylamine contained in layer A and layer B is selected from compounds of formula (I) where: Ar 1< is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; and R 1< is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, C(=O)R 2< , P(=O)(R 2< ) 2 , S(=O)R 2< , S(=O) 2 R 2< , CR 2< =CR 2< R 2< , CN, NO 2 , Si(R 2< ) 3 , OSO 2 R 2< , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is substituted by one or more radicals R 2< may be substituted, where one or more non-adjacent CH 2 groups are substituted by R 2< C=CR 2< , C=C , Si(R 2< ) 2 , Ge(R 2< ) 2 , Sn(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , P(=O)(R 2< ), SO, SO 2 , NR 2< , O,S or CONR 2< and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or a combination of these systems; two or more adjacent substituents R 1< can also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R 2< is, on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which H atoms can also be replaced by D or F; two or more adjacent substituents R 2< can also form a mono- or polycyclic,form an aliphatic or aromatic ring system; where at least one of the groups Ar 1 is an aromatic ring system having 12 to 30 aromatic ring atoms selected from spirobifluorene and fluorene, each of which is substituted by one or more radicals R 1 can be substituted.

[0045] An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is to be understood as a system which does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be connected by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as, for example, an sp 3< -hybridized C, Si, N or O atom, an sp 2< -hybridized C or N atom or an sp-hybridized C atom. For example, systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.are understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a linear or cyclic alkyl, alkenyl, or alkynyl group, or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are linked to one another via single bonds are also understood as aromatic or heteroaromatic ring systems within the meaning of this invention, for example systems such as biphenyl, terphenyl, or diphenyltriazine.

[0046] An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, which can each be substituted by radicals as defined above and which can be linked to the aromatic or heteroaromatic ring via any position, is understood to mean in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, Isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine,Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Kombinationen dieser Gruppen.,

[0047] In the context of the present invention, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, in which individual H atoms or CH 2 groups can also be substituted by the groups mentioned above in the definition of the radicals, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, Trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl or octynyl.Unter einer Alkoxy- oder Thioalkylgruppe mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy, 2,2,2-Trifluorethoxy, Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n-Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluormethylthio, Pentafluorethylthio, 2,2,2-Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio verstanden.

[0048] Preferably, the further group Ar 1< which is not spirobifluorene or fluorene is an aromatic or heteroaromatic ring system having 6 to 40 aromatic ring atoms, particularly preferably an aromatic ring system having 6 to 30 aromatic ring atoms, very particularly preferably an aromatic ring system having 12 to 30 aromatic ring atoms, selected from biphenyl, terphenyl, quaterphenyl, spirobifluorene, fluorene and indenofluorene, each of which may be substituted by one or more radicals R 1<.

[0049] In general, R 1< is preferably, identically or differently on each occurrence, H, D, F, CN, Si(R 2< ) 3 , N(R 2< ) 2 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, where the abovementioned groups may each be substituted by one or more radicals R 2< and where in the abovementioned groups one or more CH 2 groups may be replaced by -C≡C-, -R 2< C=CR 2< -, Si(R 2< ) 2 , C=O, C=NR 2< , -NR 2< -, -O-, -S-, -C(=O)O- or -C(=O)NR 2< -, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, where two or more radicals R 1< may be linked together to form a ring.

[0050] Preferably, the mono-triarylamine contained in layer A and layer B corresponds to one of the formulas (III) or (IV) where: Z is, identically or differently on each occurrence, N or CR 1< , where Z is C when a substituent is bonded; Ar 2< is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1<; Ar 3< is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; R 1< is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, C(=O)R 2< , P(=O)(R 2< ) 2 , S(=O)R 2< , S(=O) 2 R 2< , CR 2< =CR 2< R 2< , CN, NO 2 , Si(R 2< ) 3 , OSO 2 R 2< , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms,which may each be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups may be replaced by R 2<, C=CR 2<, C=C, Si(R 2<) 2, Ge(R 2<) 2, Sn(R 2<) 2, C=O, C=S, C=Se, C=NR 2<, P(=O)(R 2<), SO, SO 2, NR 2<, O, S or CONR 2< and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic Ring atoms, which may be substituted by one or more radicals R 2<, or a combination of these systems; two or more adjacent substituents R 1< may also form a mono- or polycyclic, aliphatic or aromatic ring system with each other; R 2< is, identically or differently on each occurrence, H, D, CN or an aliphatic,aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which H atoms may also be replaced by D or F; two or more adjacent substituents R 2< may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and n is 0 or 1. ,

[0051] Preferably, in formulas (III) and (IV), no more than three Z groups per aromatic ring are equal to N. Particularly preferably, 0, 1 or 2 Z groups per aromatic ring are equal to N. Very particularly preferably, all Z groups are equal to CR 1< or, if a substituent is attached, equal to C.

[0052] Preferably, Ar 2< in formulas (III) and (IV) is an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system having 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 1<.

[0053] Examples of mono-triarylamines for use in the devices according to the invention are listed below (non-inventive compounds 18 - 28, 30, 33 - 35, 76, 83 - 92, 94, 95, 97 - 99, 163 - 255 are marked with #): (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19)# (20)# (21)# (22)# (23)# (24)# (25)# (26)# (27)# (28)# (29) (30)# (31) (32) (33)# (34)# (35)# (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76)# (77) (78) (79) (80) (81) (82) (83) (84) (85)# (86)# (87)# (88)# (89)# (90)# (91)# (92)# (93) (94)# (95)# (96) (97)# (98)# (99)# (100) (101) (102) (103) (104) (105) (106) (107) (108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118) (119) (120) (121) (122) (123) (124) (125) (126) (127) (128) (129) (130) (131) (132) (133) (134) (135) (136) (137) (138) (139) (140) (141) (142) (143) (144) (145) (146) (147) (148) (149) (150) (151) (152) (153) (154) (155) (156) (157) (158) (159) (160) (161) (162) (163)# (164)# (165)# (166)# (167)# (168)# (169)# (170)# (171)# (172)# (173)# (174)# (175)# (176)# (177)# (178)# (179)# (180)# (181)# (182)# (183)# (184)# (185)# (186)# (187)# (188)# (189)# (190)# (191)# (192)# (193)# (194)# (195)# (196)# (197)# (198)# (199)# (200)# (201)# (202)# (203)# (204)# (205)# (206)# (207)# (208)# (209)# (210)# (211)# (212)# (213)# (214)# (215)# (216)# (217)# (218)# (219)# (220)# (221)# (222)# (223)# (224)# (225)# (226)# (227)# (228)# (229)# (230)# (231)# (232)# (233)# (234)# (235)# (236)# (237)# (238)# (239)# (240)# (241)# (242)# (243)# (244)# (245)# (246)# (247)# (248)# (249)# (250)# (251)# (252)# (253)# (254)# (255)#

[0054] The electronic device according to the invention is preferably selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers), and organic electroluminescent devices (OLEDs). The electronic device is particularly preferably an organic electroluminescent device.

[0055] The emitting layer of the electronic device may be a fluorescent or phosphorescent emitting layer. One or more emitting layers may be present in the device.

[0056] The electronic device according to the invention can contain a plurality of emitting layers. In this case, these emitting layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce and that emit blue, yellow, orange, or red light are used in the emitting layers. Particular preference is given to three-layer systems, i.e., systems with three emitting layers, wherein the three layers exhibit blue, green, and orange or red emission (for the basic structure, see, for example, WO 2005 / 011013). It should be noted that, instead of a plurality of color-emitting emitter compounds, a single emitter compound that emits in a broad wavelength range may also be suitable for generating white light.

[0057] The emitting layer(s) each contain one or more emitter compounds, which may be phosphorescent or fluorescent.

[0058] The term phosphorescent emitters typically includes compounds in which light emission occurs through a spin-forbidden transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, for example a quintet state.

[0059] Particularly suitable phosphorescent emitters are compounds which, upon suitable excitation, emit light, preferably in the visible range, and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80. Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescent dopants, in particular compounds containing iridium, platinum, or copper.

[0060] For the purposes of the present invention, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds.

[0061] Examples of phosphorescent emitters can be found in applications WO 2000 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 2005 / 033244, WO 2005 / 019373, and US 2005 / 0258742. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices according to the invention. The skilled person can also use other phosphorescent complexes in combination with the compounds according to the invention in OLEDs without inventive step.

[0062] Concrete examples of phosphorescent emitters that can be used in the electronic device according to the invention are listed below.

[0063] Preferred fluorescent emitters are selected from the class of arylamines. An arylamine or an aromatic amine within the meaning of this invention is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, particularly preferably having at least 14 aromatic ring atoms. Preferred examples thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.An aromatic anthracenediamine is understood to be a compound in which two diarylamino groups are directly bonded to an anthracene group, preferably in the 9,10-position. Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, with the diarylamino groups on the pyrene preferably bonded in the 1-position or 1,6-position, respectively.

[0064] The emitting layer preferably contains, in addition to one or more emitting compounds, one or more matrix materials.

[0065] Materials from various classes of substances can be considered as matrix materials, preferably for fluorescent emitters. Preferred matrix materials are selected from the classes of oligoarylenes (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing condensed aromatic groups, oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g. according to WO 2004 / 081017), hole-conducting compounds (e.g. according to WO 2004 / 058911), electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (e.g. according to WO 2005 / 084081 and WO 2005 / 084082), atropisomers (e.g. according to WO 2006 / 048268), boronic acid derivatives (e.g. according to WO 2006 / 117052) or benzanthracenes (e.g. according to WO 2008 / 145239).Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene, or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene, and / or pyrene, or atropisomers of these compounds. An oligoarylene, within the meaning of this invention, is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.

[0066] Preferred matrix materials for phosphorescent emitters are aromatic amines, in particular triarylamines, e.g. according to US 2005 / 0069729, carbazole derivatives (e.g. CBP, N,N-biscarbazolylbiphenyl) or compounds according to WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527 or WO 2008 / 086851, bridged carbazole derivatives, e.g. according to WO 2011 / 088877 and WO 2011 / 128017, indenocarbazole derivatives, e.g. according to WO 2010 / 136109 and WO 2011 / 000455, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, ketones, e.g. according to WO 2004 / 093207 or WO 2010 / 006680, phosphine oxides, sulfoxides and sulfones, e.g. according to WO 2005 / 003253, oligophenylenes, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. B. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746, zinc complexes, e.g.according to EP 652273 or WO 2009 / 062578, aluminum complexes, e.g. BAlq, diazasilole and tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730 and aluminum complexes, e.g. BAIQ.

[0067] Suitable charge transport materials which can be used in the hole injection or hole transport layer or electron blocking layer or in the electron transport layer of the electronic device according to the invention are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010 or other materials which are used in these layers according to the prior art.

[0068] All materials known in the art for electron-transport materials in electron-transport layers can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, for example Alq 3 , zirconium complexes, for example Zrq 4 , benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives. Further suitable materials are derivatives of the above-mentioned compounds, as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0069] Generally preferred hole transport materials which can be used in a hole transport, hole injection or electron blocking layer in the electroluminescent device according to the invention are indenofluorenamine derivatives (e.g. according to WO 06 / 122630 or WO 06 / 100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (e.g. according to WO 01 / 049806), amine derivatives with condensed aromatics (e.g. according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorenamines (e.g. according to WO 08 / 006449), dibenzoindenofluorenamines (e.g. according to WO 07 / 140847), spirobifluorenamines (e.g. according to WO 2012 / 034627 or the not yet published EP 12000929.5), fluorene amines (e.g. according to the not yet published applications EP 12005369.9, EP 12005370.7 and EP 12005371.5), spiro-dibenzopyran amines (e.g. according to the not yet published application EP 11009127.9) and dihydroacridine derivatives (e.g. according to the not yet published EP 11007067.9).

[0070] Metals with a low work function, metal alloys, or multilayer structures made of different metals are preferred as the cathode of the electronic device, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function, such as Ag or Al, can also be used. Combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are then generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.). Lithium quinolinate (LiQ) can also be used. The thickness of this layer is preferably between 0.5 and 5 nm.

[0071] Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x ) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers.

[0072] The electronic device is preferably manufactured by producing one or more layers by sublimation. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, it is also possible for the initial pressure to be even lower, for example, less than 10 -7 mbar.

[0073] In particular, the p-doped layer A is preferably produced by co-sublimation of dopant and monotriarylamine. One method for this is described, for example, in Solar Energy Materials & Solar Cells, 2000, 63, 83-99.

[0074] It is also preferred that one or more layers be coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g., BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0075] It is further preferred that one or more layers be produced from solution, for example, by spin coating, or by any printing process, such as screen printing, flexographic printing, nozzle printing, or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. Soluble compounds are required for this. Sufficient solubility can be achieved by suitable substitution of the compounds.

[0076] It is further preferred that, for the production of the electronic device according to the invention, one or more layers are produced from solution and one or more layers are produced by a sublimation process.

[0077] During manufacture (depending on the application), the device is structured, contacted and finally sealed, since the lifetime of the devices according to the invention is shortened in the presence of water and / or air.

[0078] The following figures explain the present invention: <h2 style=";text-align:left;direction:ltr"> Fig. 1 (not according to the claim) shows an electronic device (1) comprising anode (2), layer A (3), layer B (4), emitting layer (5), electron transport layer (6) and cathode (7). <h2 style=";text-align:left;direction:ltr"> Fig. 2 (not according to the claim) shows an electronic device (1) comprising anode (2), layer A (3), layer B (4), emitting layer (5), electron transport layer (6), electron injection layer (6a) and cathode (7). <h2 style=";text-align:left;direction:ltr"> Fig. 3 (not according to the claim) shows an electronic device (1) comprising anode (2), layer A (3), layer B (4), layer C (4a), emitting layer (5), electron transport layer (6), electron injection layer (6a) and cathode (7). <h2 style=";text-align:left;direction:ltr"> Fig. 4shows an example of an electronic device (1) according to the invention, comprising anode (2), layer A' (2a), layer A (3), layer B (4), emitting layer (5), electron transport layer (6), electron injection layer (6a) and cathode (7). <h2 style=";text-align:left;direction:ltr"> demonstration game <h2 style=";text-align:left;direction:ltr"> A) Best immune system for HOMO / LUMO-Lagen von Verbindungen

[0079] The HOMO and LUMO positions of the materials are determined using quantum chemical calculations. The Gaussian03W program package (Gaussian Inc.) is used for this purpose. For organic compounds without metals, a geometry optimization is first performed using the "Ground State / Semi-Empirical / Default Spin / AM1 / Charge 0 / Spin Singlet" method. Subsequently, an energy calculation is performed based on the optimized geometry. The "TD-SFC / DFT / Default Spin / B3PW91" method with the "6-31G(d)" basis set is used (Charge 0, Spin Singlet). For organometallic compounds, the geometry is optimized using the "Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet" method. The energy calculation is performed analogously to the organic substances described above, with the difference that the basis set "LanL2DZ" is used for the metal atom and the basis set "6-31G(d)" for the ligands. From the energy calculation, the HOMO HEh andLUMO LEh in Hartree units. From this, the HOMO and LUMO values ​​in electronvolts, calibrated using cyclic voltammetry measurements, are determined as follows: HOMO eV = HEh * 27.212 − 0.9899 / 1.1206 LUMO eV = LEh * 27.212 − 2.0041 / 1.385

[0080] For the purposes of this application, these values ​​are to be considered the HOMO and LUMO of the materials, respectively. The values ​​for the materials used in the examples are summarized in Table 1. Table 1: HOMO / LUMO values ​​of the materials <h2 style=";text-align:left;direction:ltr"> Material <h2 style=";text-align:left;direction:ltr"> HOMO (eV) <h2 style=";text-align:left;direction:ltr"> LUMO (eV) <h2 style=";text-align:left;direction:ltr"> CbzA1 -5.18 --- <h2 style=";text-align:left;direction:ltr"> SpA1 -4.85 --- <h2 style=";text-align:left;direction:ltr"> F4TCNQ --- -5.21 <h2 style=";text-align:left;direction:ltr"> MA1 -5.26 --- <h2 style=";text-align:left;direction:ltr"> MA2 -5.25 --- <h2 style=";text-align:left;direction:ltr"> TIFA1 -5.01 --- <h2 style=";text-align:left;direction:ltr"> NPB -5.19 --- <h2 style=";text-align:left;direction:ltr"> MA3 -5.40 --- <h2 style=";text-align:left;direction:ltr"> MA4 -5.41 --- <h2 style=";text-align:left;direction:ltr"> MA5 -5.35 --- <h2 style=";text-align:left;direction:ltr"> MA6 -5.27 --- <h2 style=";text-align:left;direction:ltr"> MA7 -5.31 --- <h2 style=";text-align:left;direction:ltr"> MA8 -5.46 --- <h2 style=";text-align:left;direction:ltr"> MA9 -5.35 --- <h2 style=";text-align:left;direction:ltr"> MA10 -5.42 --- <h2 style=";text-align:left;direction:ltr"> MA11 -5.18 --- <h2 style=";text-align:left;direction:ltr"> MA12 -5.32 --- <h2 style=";text-align:left;direction:ltr"> MA13 -5.32 --- <h2 style=";text-align:left;direction:ltr"> MA14 -5.27 --- <h2 style=";text-align:left;direction:ltr"> MA15 -5.19 --- <h2 style=";text-align:left;direction:ltr"> MA16 -5.23 --- <h2 style=";text-align:left;direction:ltr"> MA17 -5.23 --- <h2 style=";text-align:left;direction:ltr"> MA18 -5.20 --- <h2 style=";text-align:left;direction:ltr"> MA19 -5.43 --- <h2 style=";text-align:left;direction:ltr"> MA20 -5.20 --- <h2 style=";text-align:left;direction:ltr"> MA21 -5.20 --- <h2 style=";text-align:left;direction:ltr"> MA24 -5.38 --- <h2 style=";text-align:left;direction:ltr"> MA25 -5.14 --- <h2 style=";text-align:left;direction:ltr"> MA26 -5.14 --- <h2 style=";text-align:left;direction:ltr"> MA27 -5.12 --- <h2 style=";text-align:left;direction:ltr"> MA28 -5.32 --- <h2 style=";text-align:left;direction:ltr"> MA29 -5.24 --- <h2 style=";text-align:left;direction:ltr"> B) Herstellung der Verbindungen

[0081] The compounds used can be prepared according to common technical knowledge. The preparation of MA1 is disclosed, for example, in JP 1995-053955. Processes for the preparation of MA2, MA6, MA7, MA11, MA20, MA25, and MA27 are disclosed, for example, in WO 2012 / 034627. <h2 style=";text-align:left;direction:ltr"> C) OLED manufacturing

[0082] OLEDs that do not meet the requirements are marked with # below.

[0083] The production of OLEDs according to the invention and OLEDs according to the prior art is carried out according to a general process according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials).

[0084] The following examples V1 to E46 (see Tables 2 and 3) present the data for various OLEDs. Glass plates coated with 50 nm thick patterned ITO (indium tin oxide) serve as the substrates for the OLEDs. The substrates are wet-cleaned (dishwasher, Merck Extran cleaner), then baked for 15 minutes at 250°C and treated with an oxygen plasma before coating.

[0085] Various layers are applied to the pretreated substrates: first hole transport layer (HTL1) / optional second hole transport layer (HTL2) / hole transport layer directly adjacent to the EML (HTL3) / emission layer (EML) / electron transport layer (ETL) / optional electron injection layer (EIL) and finally a 100 nm thick aluminum cathode. The exact structure of the OLEDs can be found in Table 2. The materials required for the production of the OLEDs are shown in Table 4.

[0086] In the examples (not according to the claims) E16, E44, a 10nm thick layer of the material IC1 is additionally included between EML and ETL.

[0087] In examples E42, E43 (not according to the claims), an additional 10nm thick layer of the material IC2 is included between EML and ETL.

[0088] In examples E15 and E16 (not according to the claims), a 20 nm thick layer of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), obtained as CLEVIOS ™< P VP AI 4083 from Heraeus Precious Metals GmbH Germany, spin-coated from aqueous solution) is additionally included between ITO and HTL1.

[0089] The additional materials are thermally evaporated in a vacuum chamber. The emission layer always consists of at least one matrix material (host material) and one emitting dopant (emitter), which is mixed with the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as M1:D1 (95%:5%) means that the M1 material is present in the layer at a volume fraction of 95% and the D1 material at a volume fraction of 5%. Similarly, the electron-transport layer can also consist of a mixture of two materials.

[0090] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in λm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance (IUL) curves assuming a Lambertian radiation pattern, as well as the lifetime. The electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from them. The U1000 value in Table 3 refers to the voltage required for a luminance of 1000 cd / m². SE1000 and LE1000 refer to the current and power efficiencies achieved at 1000 cd / m². Finally, EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd / m 2< .The lifetime LD is defined as the time after which the luminance drops from the starting luminance to a certain fraction A when operated at a constant current density (given in Table 3 in column "j LD ").

[0091] The data for the various OLEDs are summarized in Table 3. Examples V1-V16 are comparative examples according to the prior art; examples E1-E13 and E15-E46 are not according to the invention. E14 shows data for an OLED according to the invention.

[0092] Some of the examples are explained in more detail below to illustrate the advantages of the OLEDs according to the invention. However, it should be noted that this represents only a selection of the data shown in Table 3.

[0093] Compared to an OLED with p-doped monoamine as HTL1 and the diamine NPB as HTL3 adjacent to the EML, an OLED with the same HTL1 and the monoamine MA2 as HTL3 shows significantly better efficiency and lifetime as well as slightly better voltage (examples V1 and E9, not according to claims).

[0094] The examples with the blue-fluorescent dopant D2 (V2-V7, V10, E5-E11 (not claimed), E14) show that the combination of a p-doped monoamine as HTL1 and a monoamine adjacent to the EML yields the best results. When diamines, amine carbazoles, or tetraamines are used according to the state of the art as HTL1, HTL2, or directly adjacent to the EML as HTL3, the performance data are less good. Using a p-doped layer of the monoamine MA2 in combination with the p-doped tetraamine SpA1 and MA2 directly adjacent to the EML also yields very good performance data (Example E14).

[0095] Using the carbazole amine CbzA1 in the HTL3 (i.e., in direct contact with the EML) and the p-doped monoamine MA1 in combination with the blue dopant D1 results in higher voltages and poorer efficiency and lifetimes than using the monoamines MA1 or MA2 in the HTL3 (examples E1, E2, and E12, not claimed). The same applies if the phosphorescent green dopant TEG1 is used instead of the blue fluorescent dopant D1 (examples E3, E4, and E13, not claimed).

[0096] Particularly good lifetimes are obtained if the monoamine, which is p-doped, is also used in the other hole transport layers (compare examples E1 and E2 as well as E3 and E4, not according to the claims).

[0097] With very good electron injection, the use of the purely phenyl-substituted monoamine MA1 is also advantageous over the monoamine MA2 (compare examples E10 and E11, not according to the claims). Although the OLEDs shown exhibit shorter lifetimes, they also exhibit lower voltages than comparable OLEDs with lower electron injection, which may be advantageous for some applications.

[0098] Examples E18 to E46 (not according to the claims) demonstrate that a variety of different compounds can be used as monotriarylamines according to the present invention without altering the fundamental technical advantage of the invention. Compounds MA1 to MA29 include, among others, fluorenyl monotriarylamines, xanthene monotriarylamines, spirobifluorene monotriarylamines, indenofluorene monotriarylamines, and other substance classes. Table 2: Structure of the OLEDs <h2 style=";text-align:left;direction:ltr"> Bsp <h2 style=";text-align:left;direction:ltr"> HTL1 Dicke <h2 style=";text-align:left;direction:ltr"> HTL2 Dicke <h2 style=";text-align:left;direction:ltr"> HTL3 Dicke <h2 style=";text-align:left;direction:ltr"> EML Dicke <h2 style=";text-align:left;direction:ltr"> ETL Dicke <h2 style=";text-align:left;direction:ltr"> EIL Dicke V1 <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (97%:3%) 140nm --- <h2 style=";text-align:left;direction:ltr"> NPB 20nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm --- V2 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 10nm --- <h2 style=";text-align:left;direction:ltr"> NPB 170nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V3 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 10nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 170nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V4 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 10nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 170nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 3nm V5 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 10nm <h2 style=";text-align:left;direction:ltr"> SpA1 140nm <h2 style=";text-align:left;direction:ltr"> MA2 30nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V6 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V7 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 3nm V8 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 160nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr">ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V9 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> CbzA1 70nm <h2 style=";text-align:left;direction:ltr"> IC1:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 40nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V10 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 10nm <h2 style=";text-align:left;direction:ltr"> SpA1 140nm <h2 style=";text-align:left;direction:ltr"> MA2 30nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V11 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA2 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V12 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA6 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V13 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA7 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V14 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA8 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V15 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA4 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm V16 <h2 style=";text-align:left;direction:ltr"> CbzA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> CbzA1 175nm <h2 style=";text-align:left;direction:ltr"> MA5 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E1# <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA1 160nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E2# <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 160nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E3# <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA1 220nm <h2 style=";text-align:left;direction:ltr"> IC1:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr">LiQ 1nm E4# <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA1 150nm <h2 style=";text-align:left;direction:ltr"> MA2 70nm <h2 style=";text-align:left;direction:ltr"> IC1:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E5# <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 10nm --- <h2 style=";text-align:left;direction:ltr"> MA2 170nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E6# <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 10nm --- <h2 style=";text-align:left;direction:ltr"> MA2 170nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 3nm E7# <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> MA1 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E8# <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> MA2 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E9# <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (97%:3%) 140nm --- <h2 style=";text-align:left;direction:ltr"> MA2 20nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm --- E10 # <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> MA1 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 3nm E11 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 170nm --- <h2 style=";text-align:left;direction:ltr"> MA2 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 3nm E12 # <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA1 140nm <h2 style=";text-align:left;direction:ltr"> CbzA1 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E13 # <h2 style=";text-align:left;direction:ltr"> MA1:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA1 150nm <h2 style=";text-align:left;direction:ltr"> CbzA1 70nm <h2 style=";text-align:left;direction:ltr"> IC1:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 40nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E14 <h2 style=";text-align:left;direction:ltr"> SpA1:F4TCNQ (96%:4%) 150nm <h2 style=";text-align:left;direction:ltr"> MA2:F4TCN Q (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 10nm <h2 style=";text-align:left;direction:ltr"> M1:D2 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E15 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA2 40nm <h2 style=";text-align:left;direction:ltr"> IC1:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 40nm --- E16 # <h2 style=";text-align:left;direction:ltr">MA2:F4TCNQ (96%:4%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA2 40nm <h2 style=";text-align:left;direction:ltr"> IC1:Cbz1:TEG1 (60%:30%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> IC1 10nm --- <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm E17 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA2 195nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E18 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA21 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E19 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA20 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E20 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA19 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E21 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA18 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E22 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA17 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E23 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA16 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E24 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA15 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E25 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA14 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E26 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA13 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E27 # <h2 style=";text-align:left;direction:ltr">MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA12 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E28 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA11 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E29 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA10 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E30 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA9 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E31 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA8 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E32 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA7 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E33 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA6 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E34 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA5 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E35 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA4 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E36 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 20nm <h2 style=";text-align:left;direction:ltr"> MA2 175nm <h2 style=";text-align:left;direction:ltr"> MA3 20nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E37 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 5nm <h2 style=";text-align:left;direction:ltr"> MA2 165nm <h2 style=";text-align:left;direction:ltr"> MA24 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E38 # <h2 style=";text-align:left;direction:ltr">MA2:F4TCNQ (96%:4%) 5nm <h2 style=";text-align:left;direction:ltr"> MA25 165nm <h2 style=";text-align:left;direction:ltr"> MA24 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E39 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 5nm <h2 style=";text-align:left;direction:ltr"> MA26 165nm <h2 style=";text-align:left;direction:ltr"> MA24 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E40 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 5nm <h2 style=";text-align:left;direction:ltr"> MA27 165nm <h2 style=";text-align:left;direction:ltr"> MA24 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E41 # <h2 style=";text-align:left;direction:ltr"> MA9:F4TCNQ (94%:6%) 20nm <h2 style=";text-align:left;direction:ltr"> MA9 190nm <h2 style=";text-align:left;direction:ltr"> MA24 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E42 # <h2 style=";text-align:left;direction:ltr"> MA9:F4TCNQ (94%:6%) 20nm <h2 style=";text-align:left;direction:ltr"> MA9 190nm <h2 style=";text-align:left;direction:ltr"> MA24 40nm <h2 style=";text-align:left;direction:ltr"> IC2:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> IC2 10nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm E43 # <h2 style=";text-align:left;direction:ltr"> MA29:F4TCNQ (94%:6%) 20nm <h2 style=";text-align:left;direction:ltr"> MA29 190nm <h2 style=";text-align:left;direction:ltr"> MA24 40nm <h2 style=";text-align:left;direction:ltr"> IC2:TEG1 (90%:10%) 30nm <h2 style=";text-align:left;direction:ltr"> IC2 10nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm E44 # <h2 style=";text-align:left;direction:ltr"> MA2:F4TCNQ (96%:4%) 5nm <h2 style=";text-align:left;direction:ltr"> MA2 240nm <h2 style=";text-align:left;direction:ltr"> MA24 20nm <h2 style=";text-align:left;direction:ltr"> IC3:TEG2:TEY1 (84.6%:15%:0.4%) 20nm <h2 style=";text-align:left;direction:ltr"> IC1 10nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 50nm E45 # <h2 style=";text-align:left;direction:ltr"> MA28:F4TCNQ (94%:6%) 20nm <h2 style=";text-align:left;direction:ltr"> MA28 190nm <h2 style=";text-align:left;direction:ltr"> MA9 10nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm E46 # <h2 style=";text-align:left;direction:ltr"> MA28:F4TCNQ (94%:6%) 20nm --- <h2 style=";text-align:left;direction:ltr"> MA9 200nm <h2 style=";text-align:left;direction:ltr"> M1:D1 (95%:5%) 20nm <h2 style=";text-align:left;direction:ltr"> ST1:LiQ (50%:50%) 30nm <h2 style=";text-align:left;direction:ltr"> LiQ 1nm Table 3: OLED data <h2 style=";text-align:left;direction:ltr"> Bsp. <h2 style=";text-align:left;direction:ltr"> U1000 (V) <h2 style=";text-align:left;direction:ltr"> SE1000 (cd / A) <h2 style=";text-align:left;direction:ltr"> LE1000 (Im / W) <h2 style=";text-align:left;direction:ltr"> EQE 1000 <h2 style=";text-align:left;direction:ltr"> CIE x / y bei 1000 cd / 2< <h2 style=";text-align:left;direction:ltr"> j LD A <h2 style=";text-align:left;direction:ltr"> LD (h) V1 4.4 7.3 5.2 5.2% 0.14 / 0.19 <h2 style=";text-align:left;direction:ltr"> 80mA / cm2< 80% 135 V2 4.8 7.2 4.7 4.8% 0.14 / 0.20 <h2 style=";text-align:left;direction:ltr"> 80 mA / cm2< 70% 220 V3 4.1 9.7 7.4 6.9% 0.13 / 0.19 <h2 style=";text-align:left;direction:ltr"> 80 mA / cm2< 70% 260 V4 3.8 10.0 8.4 6.8% 0.13 / 0.20 <h2 style=";text-align:left;direction:ltr"> 80 mA / cm2< 70% 195 V5 4.9 7.2 4.6 5.0% 0.14 / 0.19 <h2 style=";text-align:left;direction:ltr"> 80 mA / cm2< 70% 100 V6 3.7 8.4 7.1 5.8% 0.14 / 0.19 <h2 style=";text-align:left;direction:ltr"> 80 mA / cm2< 70% 315 V7 3.4 8.3 7.7 5.8% 0.14 / 0.19 80 mA / cm 2< 80% 85 V8 4.4 7.2 5.2 6.6% 0.14 / 0.13 60 mA / cm 2< 70% 230 V9 3.3 64 59 17.3% 0.34 / 0.63 20 mA / cm 2< 70% 145 V10 4.9 7.1 4.5 4.9% 0.14 / 0.19 80 mA / cm 2< 70% 95 V11 4.3 8.0 5.9 7.4% 0.14 / 0.14 60 mA / cm 2< 70% 145 V12 4.5 8.7 6.1 8.1% 0.14 / 0.14 60mA / cm 2< 70% 100 V13 4.4 8.7 6.3 8.1% 0.14 / 0.13 60mA / cm 2< 70% 160 V14 5.0 7.9 4.8 7.3% 0.14 / 0.14 60mA / cm 2< 70% 105 V15 4.8 9.2 6.0 8.5% 0.14 / 0.14 60mA / cm 2< 70% 160 V16 4.7 8.7 5.7 8.0% 0.14 / 0.13 60mA / cm 2< 70% 215 E1# 4.0 8.2 6.4 7.4% 0.14 / 0.13 60 mA / cm 2< 70% 460 E2# 3.9 8.7 7.0 8.0% 0.14 / 0.13 60 mA / cm 2< 70% 435 E3# 30 78 82 21.1% 0.34 / 0.63 20 mA / cm 2< 70% 215 E4# 3.2 70 70 19.4% 0.33 / 0.63 20 mA / cm 2< 70% 205 E5# 4.1 10.4 7.9 7.3% 0.13 / 0.19 80 mA / cm 2< 70% 435 E6# 3.5 10.2 9.2 7.2% 0.14 / 0.19 80 mA / cm 2< 70% 280 E7# 3.7 9.0 7.7 5.9% 0.14 / 0.20 80 mA / cm 2< 70% 425 E8# 3.9 8.7 7.0 6.2% 0.14 / 0.19 80 mA / cm 2< 70% 520 E9# 4.2 10.1 7.6 7.2% 0.14 / 0.19 80 mA / cm 2< 80% 260 E10# 3.5 9.0 8.0 6.3% 0.13 / 0.20 80 mA / cm 2< 80% 140 E11# 3.4 8.9 8.3 6.0% 0.14 / 0.20 80 mA / cm 2< 80% 105 E12# 4.1 8.0 6.3 7.3% 0.14 / 0.13 60 mA / cm 2< 70% 310 E13# 3.1 65 65 17.7% 0.34 / 0.63 20 mA / cm 2< 70% 190 E14 3.7 7.0 8.2 5.6% 0.14 / 0.19 80mA / cm 2< 70% 430 E15# 3.1 76 78 20.7% 0.34 / 0.62 20mA / cm 2< 70% 295 E16# 3.3 69 67 18.9% 0.35 / 0.61 20mA / cm 2< 80% 450 E17# 4.0 8.3 6.6 7.9% 0.14 / 0.13 60mA / cm 2< 70% 440 E18# 4.0 8.5 6.6 8.1% 0.14 / 0.13 60mA / cm 2< 70% 450 E19# 4.1 8.1 6.2 7.7% 0.14 / 0.13 60mA / cm 2< 70% 455 E20# 4.2 9.7 7.3 9.2% 0.14 / 0.13 60mA / cm 2< 70% 540 E21# 4.0 7.7 6.0 7.3% 0.14 / 0.13 60mA / cm 2< 70% 490 E22# 4.4 8.1 5.8 7.7% 0.14 / 0.13 60mA / cm 2< 70% 525 E23# 4.1 9.0 7.0 8.6% 0.14 / 0.12 60mA / cm 2< 70% 350 E24# 4.1 8.7 6.7 8.3% 0.14 / 0.12 60mA / cm 2< 70% 485 E25# 4.0 8.3 6.6 7.9% 0.14 / 0.12 60mA / cm 2< 70% 440 E26# 4.2 9.8 7.4 9.3% 0.14 / 0.13 60mA / cm 2< 70% 355 E27# 3.9 9.5 7.6 9.1% 0.14 / 0.13 60mA / cm 2< 70% 430 E28# 4.2 9.5 7.1 9.0% 0.14 / 0.12 60mA / cm 2< 70% 315 E29# 4.0 9.9 7.8 9.4% 0.14 / 0.12 60mA / cm 2< 70% 495 E30# 4.3 9.5 6.9 9.0% 0.14 / 0.12 60mA / cm 2< 70% 430 E31# 4.5 10.1 7.1 9.6% 0.14 / 0.12 60mA / cm 2< 70% 290 E32# 4.0 9.0 7.0 8.6% 0.14 / 0.12 60mA / cm 2< 70% 450 E33# 4.3 9.1 6.7 8.7% 0.14 / 0.14 60mA / cm 2< 70% 320 E34# 4.2 9.0 6.6 8.5% 0.14 / 0.12 60mA / cm 2< 70% 445 E35# 4.4 9.3 6.7 8.8% 0.14 / 0.13 60mA / cm 2< 70% 440 E36# 4.0 9.9 7.9 9.4% 0.14 / 0.12 60mA / cm 2< 70% 330 E37# 4.0 9.6 7.6 9.1% 0.14 / 0.13 50mA / cm 2< 80% 195 E38# 3.9 8.9 7.1 8.3% 0.14 / 0.13 50mA / cm 2< 80% 180 E39# 4.0 8.1 6.4 7.5% 0.14 / 0.13 50mA / cm 2< 80% 185 E40# 3.9 9.6 7.8 9.0% 0.14 / 0.13 50mA / cm 2< 80% 320 E41# 3.9 9.2 7.3 8.0% 0.13 / 0.15 50mA / cm 2< 80% 355 E42# 3.2 71 71 19.0% 0.35 / 0.62 20mA / cm 2< 80% 215 E43# 2.9 69 75 18.9% 0.33 / 0.63 20mA / cm 2< 80% 220 E44# 4.1 51 39 22.0% 0.53 / 0.46 20mA / cm 2< 80% 670 E45# 3.9 9.2 7.3 8.0% 0.14 / 0.15 50mA / cm 2< 80% 370 E46# 3.9 9.1 7.3 8.0% 0.14 / 0.14 50mA / cm 2< 80% 360 Table 4: Structural formulas of the materials for the OLEDs SpA1 M1 D1 D2 IC1 IC2 IC3 Cbz1 ST1 TIFA1 CbzA1 F4TCNQ LiQ TEG1 TEG2 TEY1 MA1 MA2 NPB MA3 MA4 MA5 MA6 MA7 MA8 MA9 MA10 MA11 MA12 MA13 MA14 MA15 MA16 MA17 MA18 MA19 MA20 MA21 MA24 MA25 MA26 MA27 MA28 MA29

Claims

1. Electronic device comprising - anode, - cathode, - at least one emitting layer, which is arranged between anode and cathode, - at least one p-doped layer A, which comprises a monotriarylamine as host, and which is arranged between anode and emitting layer, and - at least one layer B comprising a monotriarylamine, which is arranged between layer A and emitting layer, and - a p-doped layer A', which comprises a triarylamine, where the following layer structure is present between anode and emitting layer, where the layers are directly adjacent to one another: - anode - layer A' - layer A - layer B - emitting layer; where the monotriarylamine of layers A and B is selected, identically or differently, from compounds of the formula (I) where the following applies: Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1; and R1 is on each occurrence, identically or differently, H, D, F, CI, Br, I, CHO, C(=O)R2, P(=O)(R2)2, S(=O)R2, S(=O)2R2, CR2=CR2R2, CN, NO2, Si(R2)3, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more non-adjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms may be replaced by D or F; two or more adjacent substituents R2 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where at least one of the groups Ar1 is an aromatic ring system having 12 to 30 aromatic ring atoms which is selected from spiro-bifluorene and fluorene, which may in each case be substituted by one or more radicals R1.

2. Electronic device according to Claim 1, characterised in that one or more monotriarylamines are present identically in all layers between anode and emitting layer.

3. Electronic device according to Claim 1 or 2, characterised in that the p-doped layer A comprises a dopant which is an electron-acceptor compound.

4. Electronic device according to one or more of Claims 1 to 3, characterised in that the dopant of layer A is selected from compounds whose LUMO is not more than 0.3 eV higher than the HOMO of the monotriarylamine, preferably not more than 0.2 eV higher and particularly preferably not more than 0.1 eV higher.

5. Electronic device according to one or more of Claims 1 to 4, characterised in that the dopant of layer A is selected from quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2, metal halides, preferably transition-metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal from the 3rd main group, and transition-metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as bonding site.

6. Electronic device according to one or more of Claims 1 to 5, characterised in that the dopant of layer A is present in a concentration of 0.1 to 20% by vol., preferably 0.5 to 12% by vol., particularly preferably 1 to 8% by vol. and very particularly preferably 2 to 6% by vol.

7. Electronic device according to one or more of Claims 1 to 6, selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs).

8. Electronic device according to one or more of Claims 1 to 7, characterised in that the emitting layer is a phosphorescent emitting layer.