WO2016034556A2 - Opto-electronic device containing emitter compound with high quantum yield and solubility - Google Patents

Abstract

The invention relates to an opto-electronic device containing an organochemic emitter compound (E) which has a ΔE-distance between the lowest triplet state and the above singlet state of not more than 3000 cm^-1. Said organochemical emitter compound (E) contains at least one non-complexed ionic group. The invention also relates to a method for producing light of a specific wavelength, said method providing the step of providing a claimed opto-electronic device.

Description

 Opto-electronic device containing emitter connection with high

The present invention relates to an opto-electronic device comprising at least one organochemical emitter compound E having a ΔΕ distance between the lowest triplet state and the overlying singlet state of not more than 3000 cm ^-1 , wherein the organochemical emitter compound E contains at least one non-complexed ionic group Furthermore, the present invention comprises a method for producing this compound E and a method for producing light of a specific wavelength, comprising the step of providing an optoelectronic device according to the invention.

Organo-chemical compound based optoelectronic devices, such as light emitting electrochemical cells (LECs), organic light emitting diodes (OLEDs), organic lasers, organic solar cells ( English: "organic solar cells" (OSCs) or optical sensors, are increasingly gaining practical importance, especially LECs and OLEDs are promising components in electronic devices such as screens, but also in the lighting technology in contrast to most inorganic based optoelectronic devices The already available LEC and OLED illuminations show a pleasant light spectrum, OLED screens are characterized by particularly high color brilliance, high contrasts and energy efficiency, and OSCs are in the opposite direction to produce silicon-based solar cells in a particularly energy-efficient way.

The optically active materials used here (emitter or absorber compounds) are introduced into the optically active layer (light-emitting or absorbing layer) of the corresponding optoelectronic device. For several years, emitter compounds have been increasingly used for this purpose, which have a small energy gap (ΔΕ distance) between the lowest triplet state and the overlying singlet state. These However, compounds are usually poorly soluble and do not conduct electricity as desired.

In the prior art (for example, WO 2014/102079, WO 2013/07707, WO 2010/149748, WO 2013/017675, WO 2013/072508 and WO 2013/001086) it is known that polar substituents of emitter compounds their solubility in polar Tend to improve solvents. A polar group may hereinafter be any polar group, in particular also a nonionic polar group, which is not current-conducting, which may optionally participate in a complex formation.

In addition, in the preferred embodiments mentioned in the prior art, non-polar substituents are mentioned, since in many applications migration of the emitter compounds in the electric field is just to be avoided. In addition, substitutions of the emitter connections change the energy gap ΔΕ between the lowest triplet state and the overlying singlet state of the respective emitter connections, so that ΔΕ in many cases lies in a region which is less favorable with regard to the optical properties, such that an energy transfer between the energy states (eg Crossing (ISC), Reversed Intersystem Crossing (RISC)). Therefore, there remains a need to provide improved emitter compounds that are readily soluble and well-conductive in common solvents and yet have good emitter properties.

Surprisingly, it has been found that emitter compounds with a small energetic distance ΔΕ between the lowest triplet state and the overlying singlet state can be provided with ionic groups without the functionality as emitter compound suffers and further in high emitter concentration without the appearance of triplet Triplet annihilation and self-quenching can be used. As a result, good solubility and conductivity of emitter compounds could be achieved.

A first aspect of the invention relates to an optoelectronic device containing an organochemical emitter compound E, which has a ΔΕ distance between the lowest triplet state and the overlying singlet state of not over 3000 cm ^"1 , wherein the organochemical emitter compound E contains at least one non-complexed ionic group.

In this case, an optoelectronic device can be any optoelectronic device, therefore a device that can emit and / or absorb light when current flows. By way of example, the opto-electronic device may be a light-emitting electrochemical cell (LEC), an organic light-emitting diode (OLED), an organic laser, an organic solar cell (OSC) or an optical sensor. Particularly preferred is a light emitting electrochemical cell (LEC).

The optoelectronic device according to the invention is preferably an organochemical optoelectronic device in which the optically active layer, which can emit or absorb light (emitter layer B), consists at least predominantly of organic compounds, i. consists of hydrocarbon compounds, wherein the hydrocarbon compounds may be substituted with heteroatoms such as nitrogen, phosphorus, oxygen and / or halogens. The organochemical emitter compound E may also be a metal complex. An organochemical emitter compound E is in this case in particular any hydrocarbon compound which may optionally be substituted by heteroatoms such as nitrogen, phosphorus, oxygen, sulfur and / or halogens, and which is capable, under certain conditions, in particular the supply of a current flow, To emit light and / or under certain conditions, in particular the supply of light to absorb light and thereby cause a charge separation (or a current flow).

A non-complexed ionic group is a chemical group that undergoes ionic bonding. An ionic bond is preferably present if the electronegativity difference (ΔΕΝ) between the binding partners is greater than 1.7, and / or if, in 1 molar aqueous solution, more than 50 mol% of the bond would be cleaved to form ions. According to the invention, at least one ionic group is present in the emitter compound E which is not complexed, therefore freely present. A non-complexed group can be, for example, SO ₃ ^" , -PO 3 ^" or -COO ^" , or -NH ₃ ⁺ The emitter compound can be one, two, three, four, five, six, seven, eight, nine, ten or more These may give a total charge of the emitter compound E of> 0, of <0 or of 0, thus giving rise to a charged or uncharged emitter compound Preferred is a charged emitter compound E, in particular an emitter compound E having a Total charge of -1, -2, -3, -4, +1, +2, +3 or +4, in particular of -2 or +2.

It will be understood that the emitter compound, when neutrally charged, comprises one or more counterions that are capable of neutralizing the one or more non-complexed ionic group (s). The counterions may also form an ionic bond with one or more non-complexed ionic group (s). Many counterions can also be cleaved under certain circumstances or in certain solvents (for example, in an aqueous environment). According to the invention, the emitter compound E, as shown above, has an energy gap (ΔΕ-distance) between the lowest triplet state and the overlying singlet state of not more than 3000 cm ^-1 The determination of ΔΕ-distances is well known to the expert and can be determined about the wavelength or the wavelength difference of two emissions.

According to a preferred embodiment, the organochemical emitter compound E has a ΔΕ distance of not more than 2000 cm ^-1 , preferably not more than 1000 cm ^-1 . The opto-electronic device may be opaque, semi-transparent or (substantially) transparent. According to a preferred embodiment, the optoelectronic device is a light emitting electrochemical cell (LEC), an organic light emitting diode (OLED), an organic laser, an organic solar cell (OSC) or an optical sensor. An optoelectronic device preferably comprises at least the following layers:

A) an anode layer A, preferably comprising indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene;

B) an emitter layer B according to the present invention; and

 C) a cathode layer C, preferably comprising Al, Ca, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals, preferably in the arrangement A) - B) - C).

An organic solar cell (OSC) may also be referred to as an organochemical photovoltaic device (OPV). Even if the optoelectronic device is an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic solar cell (OSC) or an optical sensor, the optoelectronic device can optionally also be designed as a thin layer, the total not thicker than 5 mm, 2 mm, 1 mm, 0.5 mm, 0.25 mm, 100 μιτι or 10 μιτι is.

The opto-electronic device may also have a thickness in the range of 8-9 μm, 7-8 μm, 6-7 μm, 5-6 μm, 4-5 μm, 3-4 μm, 2-3 μm, 1-2 μιτι or less than 1 μιτι have.

More preferably, the optoelectronic device is a light emitting electrochemical cell (LEC), an organic light emitting diode (OLED), an organic laser, an organic solar cell (OSC) or an optical sensor containing the emitter junction E in the emitter layer B. OLEDs are known to be composed of several layers. Mostly, an anode layer A is on a substrate. The substrate may be made of any material or combination of materials. Glass plates are most commonly used. Alternatively, however, thin metal foils (for example copper, gold, silver or aluminum foils) or plastics can also be used, which allows greater flexibility of the OLED. In anode layer A, transparent materials are often used as anode materials. Since at least one of the electrodes must be transparent in order to be able to decouple the light generated in the OLED, either the anode layer A or the cathode layer C must be largely (preferably) completely transparent to the light to be coupled out.

Anode layer A usually consists to a large part or (almost) completely of one or more (largely) transparent conductive oxides ("transparent conductive oxides", TCOs) Such an anode layer A can be, for example, indium tin oxide, aluminum zinc Oxide, fluorine-tin oxide, indium-zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene. The anode layer A can also consist of one or more of the abovementioned materials, more preferably the anode consists of indium tin oxide (ITO) (usually (lnO ₃ ) o, 9 (SnO ₂ ) o, i).

The roughness of the transparent, conductive oxides used in the anode layer A can be compensated for by the use of an additional hole injection layer (HIL) Furthermore, the hole injection layer can facilitate the injection of positive quasi charge carriers by preventing the transfer of the carrier from the transparent, Poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO ₂ , V ₂ O ₅ or Cul, especially a mixture of PEDOT and PSS, can be used in the hole injection layer can also prevent the diffusion of metals from the anode layer A in the transition in the hole line layer.

On the anode layer A or hole injection layer, a hole transport layer (HTL) is typically arranged, where any hole conductor can be used Heteroaromatics such as triarylamines or carbazoles can be used as a hole conductor. The hole-conducting layer can also fulfill a leveling function and bridge the energy barrier to the emitter layer B ("EEG layer", EML, or "light-emitting layer", LEL). The hole-conducting layer may also be referred to as an electron blocking layer (EBL), Preferably, the hole conductors have high triplet energies For example, the hole-conducting layer may be a star-shaped heterocycle, such as tris (4-carbazoyl-9-ylphenyl). Amine (TCTA) may also be used as electron transporter materials as disclosed in WO 2012/130571.

As a rule, the emitter layer B, which in the context of the present invention has at least one emitter connection E, is applied to the hole-conducting layer. Optionally, the emitter layer B may also consist of the emitter connection (s) E. The composition of an emitter layer B will be described in detail above.

 Finally, an electron transport layer (ETL) can be applied to the emitter layer B. Here, any electron conductor can be used, for example electron-deficient compounds such as benzimidazoles, pyridines, triazoles, oxadiazoles (for example 1, 3,4 For example, the electron conduction layer may contain, as an electron conductor, a star-shaped heterocycle such as 1,3,5-tri (1-phenyl-1H-benzo [d] imidazol-2-yl) phenyl (TPBi) The electron transport layer can serve for energetic leveling between cathode layer C and emitter layer B and on the other hand block holes.

A cathode layer C is typically applied to the electron conduction layer. This can for example consist of a metal or a metal alloy. This may comprise, for example, Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals. For practical reasons, the cathode layer C may consist of largely optically nontransparent metals such as Mg, Ca or Al. In this case, the anode layer A should be as transparent as possible. Alternatively, the cathode layer C can also be made largely of semitransparent materials such as nanoscale Silver wires exist. The cathode layer can be vapor-deposited, for example, in a high vacuum.

As a protective layer and to reduce the injection barrier for electrons, a thin protective layer may optionally be applied between the cathode layer C and the ETL. This may for example contain lithium fluoride, cesium fluoride and / or silver and may optionally be applied by vapor deposition.

For example, OLEDs and LECs can also be produced as luminescent films, as luminous labels in smart packaging or as innovative design elements, and can also be used in cell recognition and analysis.

Preferably, an OLED but also an LEC comprises at least the following layers: A) an anode layer A, preferably comprising indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped Polyaniline, doped polypyrrole and / or doped polythiophene;

 B) an emitter layer B according to the present invention; and

 C) a cathode layer C, preferably comprising Al, Ca, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these

metals,

preferably in the arrangement A) - B) - C).

More preferably, an OLED comprises at least the following layers:

A) an anode layer A, in particular one comprising indium tin oxide; HTL) a hole line layer;

 B) an emitter layer B according to the present invention;

ETL) an electron conduction layer;

 C) a cathode layer C, preferably comprising Al, Ca or Mg.

preferably in the arrangement A) - HTL) - B) - ETL) - C).

Further preferred examples are shown in the experimental example below. In the OLED, the electrons (hence negative charge carriers) migrate in operation from the cathode towards the anode, which provides the holes (hence positive quasi charge carriers).

 The holes and electrons ideally meet in the emitter layer B, which is why it can also be called a recombination layer. Clashing electrons and holes form a bound state (exciton). From an exciton, by energy transfer, an emitter compound E serving as an emitter compound as described herein can be excited. This emitter connection E can relax into the ground state and thereby emit a photon. The color of the emitted light depends on the energy gap ΔΕ between the excited and the ground state and can be selectively varied by varying the emitter connection E.

In contrast to OLEDs, LECs are generally less complex and can be processed well from solution. It could also be used in LEC s oxidation-insensitive materials, such as for the cathode and / or hole injection layers. The excitation of the emitter connection E in the component takes place by injection of positive or negative charges which migrate through the component and preferably form an excited particle in the emitter layer B, a so-called exciton. This can put the emitter connection E in an excited state by energy transfer, from which the absorbed energy can be released again as a quantum of light.

If the optoelectronic device according to the invention is an organic solar cell (OSC), it is preferred that the device comprises the emitter compound E according to the invention as part of an absorber layer S, wherein the proportion of emitter compound E in the absorber layer preferably between 30 and 100 wt .-% is. As with OLEDs and LECs, two electrodes are also provided for OSCs. Between these, the absorber layer is arranged, in which the emitter compound E described in the present application is used. If the opto-electronic device is an OSC, it may be a single-layer or multi-layer OSC. For example, a single-layer OSC can have the following layers:

 A) a first electrode layer in large parts or (almost) completely consisting of one or more (substantially) transparent, conductive

Oxides ("transparent conductive oxides", TCOs), for example indium tin oxide, aluminum zinc oxide, fluorine tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene, in particular indium tin oxide (ITO) (eg (lnO ₃ ) o, 9 (SnO ₂ ) o, i);

 B) contains an absorber layer S (corresponding to the emitter layer B in OLEDs) containing at least one emitter compound E; and

 C) a second electrode layer of a metal or a metal alloy, such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals, carbon nanotubes

(English, "carbon nanotubes", CNTs) and / or nanoscale silver wires, in particular Mg, Ca or Al,

wherein the single-layer OSC is typically applied to one substrate (such as the first electrode layer) and protected on the other outside with a protective layer.

 A multilayer OSC can be constructed according to an OLED, wherein the layer S is referred to as the absorber layer S in the OSC, but otherwise the emitter layer B can correspond to an OLED and thus is also able to emit light under suitable conditions.

An optical sensor may, for example, be an optical sensor which measures the light intensity. Also, the optical sensor may optionally determine the light intensity of light of a particular wavelength range. An optical sensor may also be part of an array of optical sensors (hence an array), as used, for example, as an image sensor in a digital camera.

As already mentioned, the emitter compound E described above can emit light. By molecular variation (in the case of a metal complex of, for example, the ligand (s) L and / or the metal), the ΔΕ distance between the Ground state SO and the overlying first excited singlet and triplet states vary, so that it is possible to vary the wavelength of the emitted light. Accordingly, another aspect of the invention includes a method of producing light of a particular wavelength, comprising the step of providing an optoelectronic device according to the present invention.

An OLED, an LEC and an organic laser can be used as intended to produce light of a particular wavelength.

According to a particularly preferred embodiment, the optoelectronic device is a light emitting electrochemical cell (LEC). The optoelectronic device is particularly preferably a light emitting electrochemical cell (LEC) and contains the emitter connection E in the emitter layer B.

As shown above, the emitter compound E of the present invention has at least one ionic group which is not complexed. According to a preferred embodiment, the ionic group is selected from -SO 3 ^" , -PO 3 ^" , -COO ^" and -NH ₃ ⁺ According to a more preferred embodiment, the ionic group is selected from SO 3 ^" , -PO 3 ^" or -COO ^" .

According to a particularly preferred embodiment, the ionic group is SO3 ^" .

The at least one ionic group may be bonded to any part of the emitter compound E.

According to a preferred embodiment, the ionic group is bonded to an aryl radical of the organochemical emitter compound E. This aryl radical may be substituted or unsubstituted. The aryl radical is preferably substituted.

The counterion of the non-complexed ionic group according to the invention has a van der Waals radius of not more than 900 pm. Preferably, the van der der Waals radius of the counterion not more than 750 μm, more preferably not more than 600 μm, still more preferably not more than 500 μm or not more than 450 μm.

Particularly preferably, in the presence of a negatively charged non-complexed ionic group (exemplified SO3 ^{", -PO3"} or -COO ^") with the respective counter ion is an alkali metal ion or an alkaline earth metal or an ammonium ion. In particular, it is an alkali metal ion or an ammonium ion. by way of example, it is then at the counter ion is a cation selected from the group consisting of Na ^+, K ^+, Li ^+, Mg ^2+, Ca ²⁺ and NR ⁺ _4. particularly preferred is a cation selected from the group consisting of Na ⁺ , K ⁺ and Li ⁺ and NR ⁺ , especially Na ⁺ and NR ⁺ .

It is particularly preferred in the presence of a positively charged non-complexed ionic group (for example, an imidazolium, pyridinium, pyrrolidinium, guanidinium, uronium, thiouronium, piperidinium, morpholinium, ammonium or phosphonium) in the respective Counter ion around a halide ion, an ammonium ion, an isothiocyanate ion, a perchlorate ion, a nitrate ion, a tetrafluoroborate ion, a hexafluorophosphate ion, an n-butyrate, a trifluoromethanesulfonate ion, a trifluoromethanesulfonimidione, an acetate ion, a trifluoroacetate, a tetraphenylboration, a toluenesulfonate ion, a dodecylbenzenesulfonate ion Camphorsulfonation, a picration, a thiocyanate ion, a benzoate or a cyanide ion or mixture thereof. By way of example, the counterion is then an anion selected from the group consisting of CI ^" , Br ^" , F ^" , Γ, CN ^" and SCN ^" , in particular CI ^" .

According to a further alternative embodiment, the emitter compound E may also have two or more (partly) differently charged, spatially separated ionic groups, so that the charges cancel each other out (partially or completely). Spatially separated in this context means that there is a distance of at least 200 pm or at least 400 pm between the charges, so that not only a zwitterion but separate charges are present. For example, there may be a positively charged and a negatively charged ionic group such that the metal complex is amphiphilic / ambipolar. These ionic groups can be attached to the same ligand L or to different ligands L be located. There may be a spacer between the ionic groups, such as a Ci-20-Alkylspacer.

The emitter compound E itself may have any molecular structure. Preferably, the emitter compound E is a small molecule compound having a molecular weight of not more than 10 kDa, more preferably not more than 6 kDa, especially not more than 4 kDa.

Preferably, the emitter compound E allows singlet and / or triplet harvesting. As an electronic excitation state comes, with a few exceptions, either a singlet or a triplet state, consisting of three sub-states, into consideration. Since both states are usually occupied in a ratio of 1: 3 due to the spin statistics, it follows that for an emission from the singlet state, which is referred to as fluorescence, only a maximum of 25% of the excitons produced lead to emission again. In contrast, in a triplet emission, which is referred to as phosphorescence, all excitons are exploited, converted and emitted in light (triplet harvesting), so that in this case the internal quantum yield can reach the value of 100%, provided that excited with energetically above the triplet state singlet state completely relaxed in the triplet state (Intersystem Crossing (ISC)) and non-radiation competitive processes remain meaningless. Also, energy can be transferred from the triplet to the energetically overlying singlet state (reversed intersystem crossing (RISC)).

Since these have good triplet harvesting properties, the emitter compound E may preferably be a metal complex compound, especially wherein the metal is a transition metal. More preferably, the emitter compound E is a metal (I) complex. According to a more preferred embodiment, the organochemical emitter compound E is a metal (I) complex of a metal M selected from the group consisting of Cu, Ag and Au, wherein the metal (I) is preferably further complexed with at least one halogen. The metal M is particularly preferably Cu. The metal M is in the context of the invention usually a metal (l).

The metal complex formed from the one or more metals M and the one or more ligands L can, in principle, be of any conceivable stoichiometry accept. It is preferably a complex having a stoichiometry selected from the group consisting of M ₂ L ₂ , M ₂ L ₃ , M1 L1, MiL ₂ , M1 L3, MiL, M ₂ Li and M ₂ L. More preferably, it is selected from the group consisting of M ₂ L ₂ , M ₂ I_3, M1 L1 and MiL ₂ , in particular M ₂ L ₂ or M ₂ L ₃ . Here, L represents only the organochemical ligands L, which may be similar (homoleptic) or different (heteroleptic) ligands. Any inorganic ions are not included in the aforementioned stoichiometry. A complex containing two metals M (eg M ₂ L ₂ or M ₂ L ₃ ) may have a planar or butterfly structure, or a structure which may change conformation depending on the environment.

For the purposes of the invention, a metal complex is preferably an M (I) complex. More preferably, the M (l) complex has one of the following structures (a), (b) or (c):

 (b) (c) where L '- L "" are each independently of one another:

A) suitable organic ligands L, which may be either the same or different, or

B) Parts of organic ligands L, which may be either the same or different, where two or more of L '- L "' may be covalently linked together, such as L 'with L ^iN , L ^H with L ^Nii , L' with L ^N , L ^iH with L ^Nii , L 'with L ^Nii , L ^H with L ^Ni , L' with L ^H and L ^iN , L 'with L ^H and L ^iv , L' with L ^Ni and L ^iv , L ^N with L ^iN and L ^iv or all ligands Li - L ^iv with each other, in which case the conjugate represents an organic ligand L; and wherein each of X and X 'independently is a suitable anionic ligand, such as an anion selected from the group consisting of CI ^" , Br ^" , I ^" , SCN ^" , CN ^" , RS ^" , RSe ^" , RR'N ^" , RR'P ^" and RC ^ C ^" ,

wherein R and R 'independently of one another are selected from the group consisting of a Ci _-2 o-alkyl radical, adamantyl radical, _C6-i4 aryl radical, C ₂ i 3-heteroaryl radical, C _{2 - 20-} alkenyl radical, C _2-20 -alkynyl radical (-C ^ CR "), -OR", and -NR "R"', and where R ", R '" are defined as R and can also be H.

The terms "alkyl radical", "alkyl group" and the like denote linear or branched alkyl radicals in which optionally one or more hydrogen atoms may be substituted, such as for example by organic groups, functional groups or heteroatoms. Correspondingly, alkylene, alkenyl, alkenylene, alkynyl and alkynylene radicals can also be linear or else branched and optionally substituted. Preferably, the ligands L '- L "" selected from mono- and bidentate phosphine and Arsanlanden and ligands having at least one N-donor atom. The ligands can be either neutral or simply negatively charged. According to the invention contains at least one of the ligands L '- L "" a non-complexed ionic group. The ligands can either be monodentate ligands or be interconnected and form polydentate, especially bidentate, ligands. The structures therefore contain either four monodentate ligands or two bidentate ligands or a bidentate and two monodentate ligands or a tridentate and a monodentate ligand or a tetradentate ligand.

A M ₂ L ₂ complex can thus for example, a Cu2L ₂ complex, a Au ₂ L ₂ - complex or Ag ₂ L be ₂ complex, particularly preferred is a Cu ₂ L ₂ complex. An M ₂ L ₃ complex may be, for example, a Cu ₂ L ₃ complex, an Au ₂ L ₃ complex or an Ag ₂ L ₃ complex, particularly preferred is a Cu ₂ L ₃ complex.

Accordingly, at least one halogen is bonded to the metal (I) which is complexed by the at least one organochemical ligand L, hence iodine, chlorine, bromine, fluorine and / or astatine. The halogen is preferably present here as an anion, therefore as I ^" , Cl ^" , Br ^" , F ^" or At ^" . More preferably, the halogen is selected from the group consisting of I ^" , Cl ^" , and Br ^" . Particularly preferred is the halogen I ^" .

Preferably, the metal (I) complex of the present invention is a Cu (I) complex in which the Cu (I) is also bonded to a halogen selected from the group consisting of iodine, chlorine and bromine. A Cu (I) complex can be prepared from the organochemical ligand L and one or more copper halide (s) (in particular Cul, CuBr, CuCl and / or CuF).

According to a more preferred embodiment, the complexed metal is (1) Cu (1) and the halogen iodine. Even more preferably, the complexed metal is (l) Cu (I), the halogen iodine bound thereto and the counterion of at least one non-complexed ionic group of the metal (I) complex is a cation selected from the group consisting of Na ⁺ , K ⁺ and Li ⁺ , especially Na ⁺ . As stated above, the metal (I) complex according to the invention may have any desired stoichiometry. Preferably, the metal (I) complex is fourfold coordinated, therefore bound to four binding sites. These binding sites can be provided by four, three, two or even one compound. For example, bidentate organochemical ligands L can each provide two binding sites and thus function as chelate complex formers. If there are more than one organochemical ligand L in the metal (I) complex, they may be the same or different.

At least one binding site is occupied by a halogen according to the invention so that one, two or three binding sites of the four-coordinate metal (I) complex of organochemical ligand (s) L can be occupied.

Preferably, two of the four coordination sites are each occupied by a halogen and two of the four coordination sites are occupied by one or two separate organochemical ligands L. When two organochemical ligands L are present in the metal (I) complex, they may be the same or different.

In a highly preferred embodiment, the metal (I) complex is a four-coordinate organic Cu (I) complex.

The metal (I) complex according to the present invention may contain as the only complexed metal M a metal (I) selected from the group consisting of Cu, Ag and Au or may additionally comprise one or more further complexed metal (s) ( e) included. Further complexed metals are in this case preferably metal (I), more preferably metal (I) selected from the group consisting of Cu, Ag and Au. Even more preferably, there are two or more like complexed metals in a metal (I) complex, such as Cu (I), Ag (I) or Au (I). Even more preferably, in a metal (I) complex, only complexed metals of the same type as complexed metals are present, such as Cu (I), Ag (I) or Au (I), in particular Cu (I).

Preferably, the metal (I) complex contains as the only complexed metal M a metal (I) selected from the group consisting of Cu (I), Ag (I) and Au (I) or additionally a further complexed metal. The metal (I) complex particularly preferably contains as further complexed metal (I) selected from the group consisting of Cu (I), Ag (I) and Au (I), the further complexed metal (I) preferably being the same like the first, so that only two similar complexed metals (I) are contained in the metal (I) complex, especially two Cu (I). Accordingly, the metal (I) complex particularly preferably contains two quadruple complexed Cu (I).

According to a more preferred embodiment, the metal (I) complex contains two quadruple complexed Cu (I), wherein the Cu (I) additionally form two complex bonds with iodine.

According to an even more preferred embodiment, the metal (I) complex has a structure according to one of the following formulas (I) or (II):

wobei R¹, R², R³, R⁴, R⁵, R⁶, R⁷ und R⁸ unabhängig voneinander je einen beliebigen organochemischen Rest, bevorzugt einen substituierten oder unsubstituierten Arylrest, einen substituierten oder unsubstituierten Alkylarylrest, einen substituierten oder unsubstituierten Arylalkylrest oder einen substituierten oder unsubstituierten Ci_-2o- Alkylrest, darstellen, wobei mindestens einer der Reste R¹ , R², R³, R⁴, R⁵, R⁶, R⁷ und R⁸ die ionische Gruppe enthält;

where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ independently of one another any desired organochemical radical, preferably a substituted or unsubstituted aryl radical, a substituted or unsubstituted alkylaryl radical, a substituted or unsubstituted arylalkyl radical or a substituted or unsubstituted C _1-2 -alkyl radical, where at least one of the radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 contains} the ionic group;

where M is a metal (I), preferably Cu (I), Ag (I) or Au (I), in particular Cu (I);

wherein Y is any bivalent group, preferably a bivalent group containing at least one π-electron system conjugated with the structure of formulas (I) or (II), preferably a divalent group taken together with the carbon atom and the nitrogen atom of the structure the formula (I) or (II) forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and

wherein in the structure of formula (II) Z is any bivalent group, preferably a bivalent group selected from the group consisting of -R ^a -, -OR ^a -O-, -R ^a - N = N-, -N = NR ^a -, -R ^a -N = NR ^b -, -OR ^a -, -R ^a -O-, -R ^a -OR ^b -, -NR ^d -R ^a -, -R ^a -NR ^d -, -R ^a -NR ^d - R ^a -, -NR ^d -R ^a -NR ^e -, -R ^a -NR ^d -NR ^e -, -R ^a -N = N-, -NR ^e -NR ^d -R ^a -, -N = NR ^a -, -R ^a -N = NR ^b -, - N = CR ^d -NR ^e -, -R ^a -N = CR ^d -NR ^e -, -R ^a -N = CR ^d -NR ^e -R ^b -, -N = CR ^d -NR ^e -R ^a -, -N = CR ^d -R ^a -NH-, -R ^a -N = CR ^d -R ^b -NR ^e -, -N = CR ^d -R ^a -NR ^e -R ^a -, -R ^a -N = CR ^d -R ^b -NR ^e -R ^c -, -NR ^d -CR ^e = N-, -R ^a - NR ^d -CR ^e = N-, -NR ^d -CR ^e = NR ^a -, - R ^a - NR ^d -CR ^e = N - R ^b -, -NR ^d -R ^a -CR ^e = N-, -R ^a -NR ^d -R ^b - CR ^e = N-, -NR ^d -R ^a -CR ^e = NR ^b -, -R ^a -NR ^d -R ^b -CR ^e = NR ^a -, -R ^a -N = C = N-, -N = C = NR ^a -, - N = CR ^d -CR ^e = N-, -R ^a -N = CR ^d -CR ^e = N-, -N = CR ^d -CR ^e = NR ^a -, -R ^a -N = CR ^d -CR ^e = NR ^b -, - N = CR ^d -R ^a -CR ^e = NR ^b -, -R ^a -N = CR ^d -R ^b -CR ^e = N-, -R ^a -N = CR ^d -R ^b -CR ^e = NR ^c -,

-OR ^a -NR ^d -R ^a -OR ^b -NH-, -OR ^a -NR ^d -R ^b -, -R ^a -OR ^b -NR ^d -R ^c -, -NR ^d -R ^a -O- , -R ^a -NR ^d -R ^b -O-, -NR ^d -R ^a -OR ^b -, -R ^a -NR ^d -R ^b -OR ^c -, -R ^a -CO-NR ^d -, - CO-NR ^d -R ^a -, -R ^a -CO-NR ^d -R ^a -, -R ^a - NR ^d -CO-, -NR ^d -CO-R ^a - or -R ^a -NR ^d -CO -R ^a -, SR ^a -S-, -S- -OR ^a, -SR ^a -O-, -SR ^a -, -R ^a - S-, -R ^a -SR ^b -, -SR ^a -NR ^d -, - R ^a -SR ^b -NR ^d -, -SR ^a -NR ^d -R ^b -, -R ^a -SR ^b -NR ^d -R ^c -, -NR ^d -R ^a -S-, - R ^a -NR ^d -R ^b -S-, -NR ^d -R ^a -SR ^b -, -R ^a -NR ^d -R ^b -SR ^c -, -R ^a -CS-NR ^d -, -CS- NR ^d -R ^a -, -R ^a -CS- NR ^d -R ^b -, -R ^a -NR ^d -CS-, -NR ^d -CS-R ^a -, -R ^a -NR ^d -CS-R ^b -, -SO-R ^a -S-, -SO-R ^a -SO-, -SO ₂ - R ^a -SO ₂ -, -SO ₂ -R ^a -SO-, -SO-R ^a -SO ₂ -, -OR ^a -SO-, -OR ^a -SO ₂ -, -SO-R ^a -O-, -SO ₂ -R ^a -O-, - SO-R ^a -, -SO ₂ -R ^a - , -R ^a -SO-, -R ^a -SO ₂ -, -R ^a -SO-R ^b -, -R ^a -SO ₂ -R ^b -, -SO-R ^a -NR ^d -, -SO ₂ -R ^a - NR ^d -, -R ^a -SO-R ^b -NR ^d -, -SO-R ^a -NR ^d -R ^b -, -R ^a -SO-R ^b -NR ^d -R ^c -, -NR ^d -R ^a -SO-, -R ^a -NR ^d -R ^b -SO-, -NR ^d -R ^a -SO-R ^b -, -R ^a -NR ^d -R ^b -SO-R ^c -, -R ^a -SO ₂ -R ^b -NR ^d -, -SO ₂ -R ^a -NR ^d -R ^b - , R ^a - SO ₂ -R ^b -NR ^d -R ^c -, -NR ^d -R ^a -SO ₂ -, -R ^a -NR ^d -R ^b -SO ₂ -, -NR ^d -R ^a - SO ₂ -R ^b - and -R ^a -NR ^d -R ^b - SO ₂ -R ^c -ist, wherein R ^a , R ^b and R ^{c are} each independently selected from the group consisting of substituted or unsubstituted C 1-20 alkylene, substituted or unsubstituted C 2-30 alkenylene, substituted or unsubstituted C 6-30 arylene, substituted or unsubstituted C _7- 32 arylalkylene, substituted or unsubstituted Cs-33 alkylarylene and substituted or unsubstituted Cs-33- alkylarylalkylene, and wherein R ^d and R ^e are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted Ci - 2o alkyl group, a substituted or unsubstituted C2-2o-alkenyl group, a substituted or unsubstituted C6-2o aryl group, a substituted or unsubstituted C _7- 32 arylalkyl group and a substituted or unsubstituted Cs-33- Alkylarylalkylrest, in particular wherein R ^d and R ^{e are} each hydrogen. Preferably, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each comprise not more than 100 carbon atoms, more preferably not more than 50 carbon atoms, even more preferably not more than 40 carbon atoms even more preferably not more than 30 carbon atoms, even more preferably not more than 20 carbon atoms.

As used in the context of the present invention, a C 1-20 -alkylene may be any straight or branched alkylene having from 1 to 20 carbon atoms. The unbranched or branched alkylene may be linear or cyclic. A linear alkylene preferably contains 1 to 10 carbon atoms. A cyclic alkylene preferably contains from 4 to 10 carbon atoms, more preferably 5, 6 or 7 carbon atoms. The C 1 -C 20 -alkylene is preferably a -methylene, -ethylene, -n-propylene, -isopropylene, -n-butylene, -isobutylene, 2-methylpropylene, -pentylene, -hexylene, Heptylen-, -Octylen-, -Nonylen- or -Decylen- or -2,2-Dimethylbutylen-, - Cyclopropylene, -Cyclopentylen-, -Cyclohexylen- or -cycloheptylene radical. In this case, the radical with any of the carbon atoms can be attached to the basic structure according to the invention. Particularly preferably, a terminal carbon atom, therefore an alkylene group, is attached to the basic structure according to the invention. As used in the context of the present invention to provide a Ci may be o- _-2 alkenylene each straight or branched alkenylene having 2 to 20 carbon atoms. The straight or branched alkenylene may be linear or cyclic. A linear alkenylene preferably contains 2 to 10 carbon atoms. A cyclic alkenylene preferably contains from 4 to 10 carbon atoms, more preferably 5, 6 or 7 carbon atoms. Preferably, the Ci-20-alkenylene is an ethenylene, propenylene, isopropenylene, 1-butenylene, 2-butenylene, 2-Methylenpropenylen-, pentenylene, hexenylene, heptenylene, octenylene, Nonenylen or Decenylen-, 2 , 2-Dimethylenbutenylene, cyclopropenylene, cyclopentenylene, cyclohexenylene, cycloheptenylene or cyclohex-2-enylene radical. In this case, the radical with any of the carbon atoms can be attached to the basic structure according to the invention. Particularly preferred is a terminal carbon atom, therefore a -CH ₂ - Akylen- or -CH = CH group, attached to the basic structure according to the invention. The double bond can be located at any position per se.

Substituted may be mentioned in the context of the present invention radicals with any substituents. For example, one or more hydrogen atoms may be substituted by halogens (especially F, Cl, Br or I). The substitution can also be the presence of one or more optional functional groups (for example selected from the group consisting of -COOH, -OH, = O, -NH ₂ , = NH, = N, -C =, -O-C =, - N = C = O, -SH, = S, -CSOH, -SC ^ N, -N = C = S, -OPO ₃ H ₂ ) on the rest.

In the case of the cyclic hydrocarbons, alternatively or additionally, a carbon atom (with the hydrogen atoms bonded thereto) can also be replaced by a heteroatom (in particular oxygen, nitrogen or sulfur, therefore approximately -CH ₂ - by -O-, -NH- or -S- and = CH - by = N-) or a functional group (especially -O-, -CO-O-, -CO-NH-, -CN-O-, -CNR ^d -O-, -S-, -CO-S- , -CS-O-, -CS-NH-, -CN-S-, -CNR ^d -S-, where R ^{d is} as defined above).

More preferably, the metal (I) complex has a structure according to the formula (I) or (II), wherein Y is a divalent group which together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system. Even more preferably, the metal (I) complex has a structure according to the formulas (I), wherein

 Y is a divalent group which, together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II), forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and

Z is -R ^a - wherein R ^{a is} a substituted or unsubstituted C 1-20 alkylene

substituted or unsubstituted C2-2o alkenylene, a substituted or

is unsubstituted C6-2o arylene, a substituted or unsubstituted C _7- 32 arylalkylene, substituted or unsubstituted C8-33-alkylarylalkylene.

Most preferably, the metal (I) complex has a structure according to formula (I) wherein

 Y is a divalent group which, together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II), forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and

Z is -OR ^a -O- wherein R ^{a is} a substituted or unsubstituted C 1-20 alkylene, a substituted or unsubstituted C 2-30 alkenylene, a substituted or

is unsubstituted C6-2o arylene, a substituted or unsubstituted C _7- 32 aralkyl, a substituted or unsubstituted C8-33-alkylarylalkylene.

Most preferably, the metal (I) complex has a structure according to formula (I) or (II) where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently any organochemical radical, preferably a substituted or unsubstituted aryl radical, a substituted or unsubstituted alkylaryl radical, a substituted or unsubstituted arylalkyl radical or a substituted or unsubstituted Ci-2o alkyl radical, wherein at least one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 contains} the ionic group;

wherein M is Cu (I);

wherein Y is a divalent group which together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and

where Z, if present, is -R ^a - or -OR ^a -O-. According to a highly preferred embodiment, the metal (I) complex has a structure according to formula (I) or (II), wherein Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring, pyrazole ring, indazole ring, oxazole ring, benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring , Pyrimidine ring and quinazoline ring, in particular together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) forms a substituted or unsubstituted pyridine, 1, 3,4-oxadiazole, imidazole or benzimidazole ring.

In a highly preferred embodiment, the metal (I) complex has a structure according to formula (I) wherein Z is -R ^a - or -OR ^a -O-.

According to an even more preferred embodiment, Y together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) forms a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring , Triazole, benzimidazole, purine, pyrazole, indazole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, quinoline, isoquinoline, pyrazine, quinoxaline, pyrimidine, and quinazoline ring

in particular together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) forms a substituted or unsubstituted pyridine, 1, 3,4-oxadiazole, imidazole or benzimidazole ring.

According to an even more preferred embodiment, here additionally Z, if present (therefore in the case of a compound of formula (I)) -R ^a - or -OR ^a -O-.

Accordingly, in a highly preferred embodiment, the metal (I) complex has a structure according to formula (I) or (II) wherein

Z if present (therefore in the case of a compound of formula (I)), -R ^a - or - OR ^a -O-; and or Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring, Pyrazole ring, indazole ring, oxazole ring,

Benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and nitrogen atom of the structure of formulas (I) or (II), form a substituted or unsubstituted pyridine; , 3,4-oxadiazole, imidazole or benzimidazole ring forms.

Even more preferably, the metal (I) complex has a structure according to formula (I), wherein

Z is -R ^a - or -OR ^a -O-; and

 Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring, Pyrazole ring, indazole ring, oxazole ring,

Benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and nitrogen atom of the structure of formulas (I) or (II), form a substituted or unsubstituted pyridine; , 3,4-oxadiazole, imidazole or benzimidazole ring forms.

Even more preferably, the metal (I) complex has a structure according to formula (I) or (II)

wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently any organochemical radical, preferably a substituted or unsubstituted aryl radical, a substituted or unsubstituted alkylaryl radical, a substituted or unsubstituted arylalkyl radical or a substituted or unsubstituted Ci-2o Alkyl radical, wherein at least one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 contains} the ionic group;

wherein M is Cu (I);

wherein Y together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) forms a substituted or unsubstituted aromatic ring system selected from the group consisting of a

Pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring, pyrazole ring, indazole ring, oxazole ring, benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) is a substituted or unsubstituted pyridine, 1,4-oxadiazole, imidazole or benzimidazole ring; and wherein Z, if present, is -R ^a - or -OR ^a -O-.

According to a highly preferred embodiment, the metal (I) complex has a structure according to formula (I) or (II), wherein

R ¹ and / or R ^{3 are} independently of each other at least one ionic group substituted aryl radicals, preferably R ¹ and R ^{3 are} each substituted with at least one ionic group aryl radicals; and or

R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals.

More preferably, the metal (I) complex has a structure according to formula (I) or (II), wherein

R ¹ and / or R ^{3 are} independently of each other at least one ionic group substituted aryl radicals, preferably R ¹ and R ^{3 are} each substituted with at least one ionic group aryl radicals; and

R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals. Even more preferably, the metal (I) complex has a structure according to formula (I) or (II), wherein

R ¹ and R ^{3 are} each aryl groups substituted with an ionic group; and

R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals. Preferably, the metal (I) complex has a structure according to formula (I) or (II) wherein R ¹ and R ^{3 are} each aryl radicals substituted with an ionic group;

wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals;

where M is a metal (I), preferably Cu (I), Ag (I) or Au (I), in particular Cu (I);

wherein Y is any bivalent group, preferably a bivalent group containing at least one π-electron system conjugated with the structure of formulas (I) or (II), preferably a divalent group taken together with the carbon atom and the nitrogen atom of the structure the formula (I) or (II) forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and

wherein Z, if present, is any bivalent group, preferably a bivalent group selected from the group consisting of -R ^a -, -OR ^a -O-, -OR ^a -, - R ^a -O-, -NH-R ^{a is} -NH-, -N = R ^a -NH-, -HN-R ^a = N-, -N = R ^a = N-, -OR ^a -NH- or -NH-R ^a -O-, where R ^a is a substituted or unsubstituted Ci-20 alkyl, substituted or unsubstituted C2-2o-alkenyl, a substituted or unsubstituted C6-2o-aryl, substituted or unsubstituted C _7- 32 aralkyl, a substituted or unsubstituted C8-33 Alkylarylalkyl.

Even more preferably, the metal (I) complex has a structure according to formula (I) or (II)

wherein R ¹ and R ^{3 are} each aryl groups substituted with at least one ionic group;

wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals, alkyl radicals, arylalkyl radicals, alkylaryl radicals or alkylarylalkyl radicals;

wherein M is Cu (I);

wherein Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring , Pyrazole ring, indazole ring, oxazole ring, benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and nitrogen atom of the structure of formulas (I) or (II) substituted or unsubstituted pyridine, 1, 3,4-oxadiazole, imidazole or

Benzimidazole ring forms; and

where Z, if present, is -R ^a - or -OR ^a -O-. Even more preferably, the metal (I) complex has a structure according to formula (I) or (II)

wherein R ¹ and R ^{3 are} each aryl groups substituted with an ionic group;

wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals;

wherein M is Cu (I);

wherein Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring , Pyrazole ring, indazole ring, oxazole ring, benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and nitrogen atom of the structure of formulas (I) or (II) substituted or unsubstituted pyridine, 1, 3,4-oxadiazole, imidazole or benzimidazole ring forms; and

where Z, if present, is -R ^a - or -OR ^a -O-.

The metal (I) complex particularly preferably has a structure of the formula (I) or (II)

wherein R ¹ and R ^{3 are} each aryl groups substituted with an ionic group;

wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals;

wherein M is Cu (I);

wherein Y together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) forms a substituted or unsubstituted pyridine or 1,3,4-oxadiazole ring; and

wherein Z, if present, - [Ci-io-alkylene] - is.

The metal (I) complex particularly preferably has a structure of the formula (I) or (II)

wherein R ¹ and R ^{3 are} each aryl groups substituted with an ionic group; wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals;

wherein M is Cu (I);

wherein Y together with the carbon atom and the nitrogen atom of the structure of formulas (I) or (II) forms a substituted or unsubstituted pyridine or 1,3,4-oxadiazole ring; and

wherein Z, if present, is -O- [Ci-io-alkylene] -O-.

As used herein, a substituted pyridine ring may be any substituted pyridine radical substituted with one, two, three, or any four of the same or different substituents. A substituent here is preferably a C 1-20 -alkyl radical, in particular a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a pentyl radical, a hexyl radical, a heptyl radical, an octyl radical, a nonyl radical or a decyl radical. The substituted pyridine ring is preferably monosubstituted or disubstituted, in particular monosubstituted. More preferably, the substituted pyridine ring is substituted in a single substituted position at carbon 4. In particular, the substituted pyridine ring is simply substituted with a Ci-20-alkyl radical at carbon position 4.

As used herein, a substituted 1,3,4-oxadiazole ring may be any substituted 1,3,4-oxadiazole ring substituted with one, two, three, or any four of the same or different substituents. A substituent here is preferably a C 1-20 -alkyl radical, in particular a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a pentyl radical, a hexyl radical, a heptyl radical, an octyl radical, a nonyl radical or a decyl radical. The substituted pyridine ring is preferably monosubstituted or disubstituted, in particular monosubstituted. More preferably, the substituted pyridine ring is substituted in a single substituted position at carbon 4. In particular, the substituted pyridine ring is simply substituted with a Ci-20-alkyl radical at carbon position 4. By way of example, the metal (I) complex may be a Cu (I) complex of a structure of formula (I) or (II) wherein R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} each unsubstituted Aryl radical and Y together with the carbon atom and the nitrogen atom of the structure of the formula (I) is a ring selected from the group consisting of a) an unsubstituted pyhdine ring,

 b) a methyl-substituted pyhdine ring at position 4,

 c) an ethyl-substituted pyridine ring at position 4,

 d) a propyl-substituted pyridine ring at position 4,

 e) a butyl-substituted pyridine ring at position 4,

 f) a pentyl-substituted pyridine ring at position 4,

 g) a hexyl-substituted pyridine ring at position 4,

 h) a position 4 heptyl-substituted pyridine ring,

 i) an octyl-substituted pyridine ring at position 4,

 j) a nonyl-substituted pyridine ring at position 4 and

 j) a position 4 decyl-substituted pyridine ring

 forms and,

 wherein the remaining radicals, if present (therefore Z is present only in a structure according to formula (II)) are defined as:

-PO3- unsubstituiert -R^a-N=N-

-PO3- unsubstituted -R ^a -N = N-

-PO3 ^" unsubstituted -OR ^a -NH-

-PO 3 unsubstituted -NH-R ^a -O-

-COO ^" unsubstituted -R ^a -

-COO ^" unsubstituted -OR ^a -O-

-COO ^" unsubstituted -OR ^a -

-COO ^" unsubstituted -NH-R ^a -NH-

-COO ^" -N = CH-NH- -N = CH-NH-

-COO ^" unsubstituted -HN-CH = N-

-COO ^" unsubstituted -R ^a -N = N-

-COO ^" unsubstituted -OR ^a -NH-

-COO ^" unsubstituted -NH-R ^a -O-

-NH ₃ ⁺ unsubstituted -R ^a -

-NH ₃ ⁺ unsubstituted -OR ^a -O-

-NH ₃ ⁺ unsubstituted -OR ^a -

-NH ₃ ⁺ unsubstituted -NH-R ^a -NH-

-NH ₃ ⁺ unsubstituted -N = CH-NH-

-NH ₃ ⁺ unsubstituted -HN-CH = N-

-NH ₃ ⁺ unsubstituted -R ^a -N = N-

-NH ₃ ⁺ unsubstituted -OR ^a -NH-

-NH ₃ ⁺ unsubstituted -NH-R ^a -O- unsubstituted -SO ₃ ^" -R ^a - unsubstituted -SO ₃ ^" -OR ^a -O- unsubstituted -SO ₃ ^" -OR ^a - unsubstituted -SO ₃ ^" -NH- R ^a -NH- unsubstituted -SO ₃ ^" -N = CH-NH- unsubstituted -SO ₃ ^" -HN-CH = N- unsubstituted -SO ₃ ^" -R ^a -N = N- unsubstituted -SO ₃ ^" -OR ^a -NH- unsubstituted -SO ₃ ^" -NH-R ^a -O-

-SO ₃ ^" -SO ₃ ^" -R ^a -

-SO ₃ ^" -SO ₃ ^" -OR ^a -O-

-COO^" -PO₃ ^" -R^a-N=N--SO ₃ ^" -SO ₃ ^" -OR ^a -

-COO ^" -PO ₃ ^" -R ^a -N = N-

-COO ^" -PO ₃ ^" -OR ^a -NH-

-COO ^" -PO ₃ ^" -NH-R ^a -O-

-NH ₃ ⁺ -PO ₃ ^" -R ^a -

-NH ₃ ⁺ -PO ₃ ^" -OR ^a -O-

-NH ₃ ⁺ -PO ₃ ^" -OR ^a -

-NH ₃ ⁺ -PO ₃ ^" -NH-R ^a -NH-

-NH ₃ ⁺ -PO ₃ ^" -N = CH-NH-

-NH ₃ ⁺ -PO ₃ ^" -HN-CH = N-

-NH ₃ ⁺ -PO ₃ ^" -R ^a -N = N-

-NH ₃ ⁺ -PO ₃ ^" -OR ^a -NH-

-NH ₃ ⁺ -PO ₃ ^" -NH-R ^a -O- unsubstituted -SO ₃ ^" -R ^a - unsubstituted -SO ₃ ^" -OR ^a -O- unsubstituted -SO ₃ ^" -OR ^a - unsubstituted -SO ₃ ^" -NH-R ^a -NH- unsubstituted -SO ₃ ^" -N = CH-NH- unsubstituted -SO ₃ ^" -HN-CH = N- unsubstituted -SO ₃ ^" -R ^a -N = N- unsubstituted -SO ₃ ^" -OR ^a -NH- unsubstituted -SO ₃ ^" -NH-R ^a -O-

-SO ₃ ^" -COO ^" -R ^a -

-SO ₃ ^" -COO ^" -OR ^a -O-

-SO ₃ ^" -COO ^" -or ^a -

-SO ₃ ^" -COO ^" -NH-R ^a -NH-

-SO ₃ ^" -COO ^" -N = CH-NH-

-SO ₃ ^" -COO ^" -HN-CH = N-

-SO ₃ ^" -COO ^" -R ^a -N = N-

-SO ₃ ^" -COO ^" -OR ^a -NH-

-SO ₃ ^" -COO ^" -NH-R ^a -O-

-PO ₃ ^" -COO ^" -R ^a -

-PO ₃ ^" -COO ^" -or ^a -O-

-NH₃ ⁺ -NH₃ ⁺ -R^a-N=N--PO ₃ ^" -COO ^" -or ^a -

-NH ₃ ⁺ -NH ₃ ⁺ -R ^a -N = N-

-NH ₃ ⁺ -NH ₃ ⁺ -OR ^a -NH-

-NH ₃ ⁺ -NH ₃ ⁺ -NH-R ^a -O-

Here, R ^{a is} as defined above, preferably an unsubstituted C _4-7 alkylene, or an --O-Ce-aryl-Ο- in which the -O-groups are in paraposition to each other is, in particular pentylene, hexylene or -OC _ö -aryl-O-, in which the -O-groups are in paraposition to each other.

According to a highly preferred embodiment, the metal (I) complex has a structure according to one of the following formulas (III) or (IV):

wobei Z wie in Anspruch 8 oder 9 definiert ist, insbesondere wobei Z ein unsubstitutierter C₄-C₇-Alkenylenrest oder -O-Aryl-O- ist;

wherein Z is as defined in claim 8 or 9, in particular wherein Z is an unsubstituted C ₄ -C ₇ alkenylene radical or -O-aryl-O-;

wherein R ¹ and R ^{3 are} each aryl radicals substituted with at least one ionic group, preferably wherein the ionic group is selected from -SO ₃ ^" , -PO ₃ ^" , -COO ^" and -NH ₃ ⁺ , in particular wherein the ionic group SO _3; and wherein R ⁹ is any radical, preferably where R is a Ci- ₂₀ alkyl or H, in particular wherein R ⁹ is a Cno alkyl or H.

Preferably, R ¹ and R ^{3 are} each substituted with at least one -SO ₃ ^" group and R ⁹ is a d-io-alkyl. Even more preferably, the metal (I) complex has a structure according to formula (IV),

wherein Z is an unsubstituted C ₄ -C ₇ alkylene radical or -O-aryl-O-;

wherein R ¹ and R ^{3 are} each substituted with at least one -SO 3 ^" group, and wherein R ^{9 is} a C 1-10 alkyl.

Even more preferably, the metal (I) complex has a structure according to formula (IV),

wherein Z is an unsubstituted C ₄ -C ₇ alkylene radical or -O-aryl-O-;

wherein R ¹ and R ^{3 are} each substituted in the meta position with at least one -SO 3 ^" group;

wherein R ^{9 is} a Ci-io-alkyl.

According to a very particularly preferred embodiment, the metal (I) complex has a structure according to the following formula (V):

According to an alternative preferred embodiment, the organochemical emitter compound E contains no transition metal.

Therefore, the emitter compound E is then not a metal complex. Preferably, such an emitter compound E is a TADF emitter compound. This can have one of the following basic structures:

Do-Gr-Ab;

 Do-Gr;

Ak-Gr; or Do-Gr-Gr-Ak-Thurs

In this case, Do represents an electron donor, therefore an electron-donating group which may be present in the emitter compound E one, two or more times. For example, Do may be selected from the group consisting of -O (-), amines (eg primary, secondary or tertiary amines), -OH, methoxyalkylene, esters (of the form -O-CO-), amides, (hetero) aryl radicals, Phenoxazinyl, phenothiazinyl, carbazolyl, and dihydrophenazinyl radicals. In this case, Ak represents an electron acceptor, therefore an electron-withdrawing group which may be present in the emitter compound E one, two or more times. For example, Ak may be selected from the group consisting of halogens, carbonyl groups, carboxylate groups, ester groups (of the form -CO-O-), - (CO) Cl, -CF ₃ , -BF ₂ , -CN, -S (O) ₂ OH, -S (O) ₂ O-alkyl, -S (O) ₂ ^" , -P (O) R ^" , -NH ₃ ⁺ , ammonium groups, -NO ₂ , halogenated alkyl radicals, triazines, and tertiary boranes, wherein R is any organic radical.

In this case, Gr represents the organic skeleton, which typically contains a plurality of conjugated double bonds. For example, Gr can be selected from the group consisting of aromatic, heteroaromatic and / or aliphatic radicals having a plurality of conjugated double bonds. Preferably, Gr has one or more (hetero) aromatic rings of less than 15 ring atoms, preferably not more than 10 ring atoms, in particular not more than 7 ring atoms. One or more of the hetero) aromatic rings may be substituted by aliphatic radicals of not more than 10, preferably not more than 6, in particular not more than 3 atoms in length. Alternatively, Gr can also have nonconjugated double bonds or even no double bonds.

The molecular orbitals of Ak and Gr or of Do and Gr overlap one another.

The basic structures usually give rise to a molecule with a dipole moment> 0.

bei der R¹⁰ eine ionische Gruppe ausgewählt ist aus der Gruppe bestehend aus -SO3^", - PO3^", -COO^" und -NH₃ ⁺, insbesondere wobei die ionische Gruppe eine SO3^" ist; bei der X eine direkte Bindung oder eine divalente organische Verbrückung ausgewählt aus der Gruppe bestehend aus einem Ci-g-Alkylen-, C^-s-Alkenylen-, C^-s-Alkinylen- oder Arylenrest, -CRR', -C=CRR\ -C=NR, -NR-, -O-, -SiRa-, -S-, -S(O)-, and -S(O)₂- und einer Kombination zweier oder mehrerer daraus; bei der Y NR, O oder S darstellt; Preferably, the emitter compound E has a triphenylamine group. According to a highly preferred embodiment, the organochemical emitter compound E has a structure according to one of the following formulas (VI) to (XV):

wherein R ^{10 is} an ionic group selected from the group consisting of -SO 3 ^" , - PO 3 ^" , -COO ^" and -NH ₃ ⁺ , especially where the ionic group is an SO 3 ^" ; X is a direct bond or a divalent organic bridging selected from the group consisting of a Ci-g-alkylene, C ^ -s-alkenylene, C ^ -s-alkynylene or arylene radical, -CRR ', -C = CRR \ -C = NR, -NR-, -O-, -SiRa-, -S-, -S (O) -, and -S (O) ₂ - and a combination of two or more thereof; wherein Y represents NR, O or S;

wherein Ar is a substituted or unsubstituted aryl or heteroaryl radical of from 5 to 24 aromatic ring atoms, which may be optionally substituted with one or more R, preferably wherein Ar is selected from the group consisting of phenyl, benzyl, ortho, meta or para-biphenyl, ortho, meta, para or branched terphenyl, ortho, meta, para or branched quaterphenyl, 1-naphthyl, 2-naphthyl, pyrrole, furanyl, thiophenyl, indolyl, benzofuranyl, benzothiophenyl, carbazolyl, Dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, anthracenyl, phenanthrenyl, pyrenyl, benzanthracenyl, and combinations of any two or more thereof, which may optionally be substituted with one or more R, in particular wherein Ar is a phenyl or benzyl radical; wherein R and R 'are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -NR ^a R ^b , -CN, -CF ₃ , -NO ₂ , - OH, - COOH, -COOR ^a , -CO (NR ^a ) (NR ^b ), -SiR ^a R ^b R ^c , -B (OR ^a ) (OR ^b ), -CO-R ^a , -POR ^a R ^b , -O POR ^a R ^b , -SO-R ^a , -SO ₂ R ^a , -OSO ₂ R ^a , a linear alkyl, alkoxy or thioalkoxy radical of 1 to 40 carbon atoms, a linear alkenyl or alkynyl radical of 2 to 40 carbon atoms a branched or cyclic alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radical of from 3 to 40 carbon atoms, an aromatic ring system of from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy radical of from 5 to 60 carbon atoms, and a diarylamino, diheteroarylamino or Arylheteroarylaminorest of 10 to 40 aromatic ring atoms,

each optionally substituted with one or more R ^a , wherein two or more contiguous CH ₂ groups optionally -R ^a C = CR ^b -, -C ^ C-, -SiR ^a R ^b -, -GeR ^a R ^b -, -SnR ^a R ^b -, -CO-, -CS-, -CSe-, -CNR ^a -, -POR ^a -, -O- (PO) R ^a -O-, -SO-, SO ₂ , NR ^a -, -O-, -S- or -CONR ^a - can be exchanged and wherein one or more hydrogen atoms can be substituted by deuterium, F, Cl, Br, I, CN, CF ₃ or NO ₂ and / or where two or more radicals R can optionally form mono-, bi- or polycyclic aliphatic or aromatic ring systems with one another; wherein R ^a , R ^b and R ^{c are} each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -NR ^d R ^e , -CN, -CF ₃ , - NO ₂ , -OH, -COOH, -COOR ^e , -CO (NR ^d ) (NR ^e ), -SiR ^d R ^e R ^f , -B (OR ^d ) (OR ^e ), -CO-R ^a , POR ^d R ^e , -O- POR ^d R ^e , -SO-R ^d , -SO ₂ R ^d , -OSO ₂ R ^d , a linear alkyl, alkoxy or thioalkoxy radical of 1 to 40 carbon atoms, a linear alkenyl radical or alkynyl of from 2 to 40 carbon atoms, a branched or cyclic alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radical of from 3 to 40 carbon atoms, an aromatic ring system of from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy radical of from 5 to 60 carbon atoms and a diarylamino, diheteroarylamino or aryl heteroarylamino radical of from 10 to 40 aromatic ring atoms,

each optionally optionally substituted with one or more R ^d , wherein two or more contiguous CH ₂ groups optionally -R ^d C = CR ^e -, -C ^ C-, -SiR ^d R ^e -, -Ge R ^d R ^e -, -SnR ^d R ^e -, -CO-, -CS-, -CSe-, -CNR ^d -, -POR ^d -, -O- (PO) R ^d -O-, -SO-, SO ₂ - NR ^d -, -O-, -S- or -CONR ^d - can be exchanged and wherein one or more hydrogen atoms can be substituted by deuterium, F, Cl, Br, I, CN, CF ₃ or NO ₂ ; wherein R ^d , R ^e and R ^{f are} each independently selected from the group and / or heteroaromatic radical of 1 to 20 carbon atoms, optionally one or more hydrogens may be substituted by F or CF 3. The emitter compound E of the present invention, whether or not it is a metal complex, can be used as an optically active compound, therefore, depending on the context, as a light-emitting compound or as a light-absorbing, charge-separating compound. For the purposes of the present invention, such an emitter compound E is to be understood in the broadest sense as any optically active compound which is capable of emitting light in an optoelectronic device under certain conditions. Accordingly, the emitter connection E can actually be used to generate light. But it can also be used differently, such as to absorb light and convert it into electrical energy (charge separation and / or current flow).

The emitter connection E can consequently be used in an emitter layer B. For this, the compound can be used together with other compounds in a composition. For the purposes of the present invention, an emitter layer B is to be understood in the broadest sense as any optically active layer capable of emitting light under certain conditions in an opto-electronic device. Accordingly, the emitter layer B can actually be used to generate light. But it can also be used differently, for example to absorb light and convert it into electrical energy. Under a layer according to the present invention is preferably a largely planar geometry to understand. The emitter layer B is preferably not thicker than 1 mm, more preferably not thicker than 0.1 mm, more preferably not thicker than 10 μιτι, even more preferably not thicker than 1 μιτι, in particular not thicker than 0.1 μιτι. Accordingly, according to a highly preferred embodiment, the organochemical emitter compound E is present in the emitter layer B in composition Z with an ionic liquid, one or more salts and / or one or more polymer (s). For example, the composition Z may additionally contain a salt with ions having a van der Waals radium of not more than 800 μm. For example, the composition NaCl, KCl, MgCl ₂ , CaCl ₂ , LiCl, NH ₃ Cl, NaBr, KBr, MgBr ₂ , CaBr ₂ , LiBr, NH ₃ Br, Nal, Cl, Mgl ₂ , Cal ₂ , NH ₃ I, NaCN, KCN, Mg (CN) ₂ , Ca (CN) ₂ , LiCN, NaSCN, KSCN, Mg (SCN) ₂ , Ca (SCN) ₂ , NH ₃ SCN, Lil, Fluorides, Phosphates, Sulfates, Borates (Perchlorates) , Interhalides such as IBr ₂ ^" , aluminates, tungstates, molybdate, salts of group 12 (eg ZnCl ₂ ), ammonium salts, oxonium salts, and / or phosphonium salts The emitter layer B is preferably an organochemical light-emitting layer consisting predominantly of organic compounds ( hydrocarbon compounds), which may be substituted with heteroatoms such as nitrogen, phosphorus, oxygen, sulfur and / or halogens.

 At least one of the hydrocarbon compounds represents an emitter compound E in the context of the present invention. Optionally, the emitter layer B can also fluorescent polymers (eg Superyellow (SY)), photoluminescent nanoparticles (such as silicon), quantum dots ("quantum dots"), cadmium selenide and / or exciplexes, optionally diluted with host molecules ("hosts"). By way of example, the host molecules W described in WO 2013/007709 or WO 2013/007710 may be used, which may also be present in an uncojugated state. Guanidium compounds as described in WO 2012/130571 and / or polyethylene oxide (PEO) can also be used in particular for the production of LECs.

In most cases, to generate light, the emitter layer B, which is part of an optoelectronic device, is supplied with electrical or chemical energy, in particular with electrical energy. For the supply of energy current can be connected, wherein the current flow through the emitter layer B, the emitter compounds E contained therein so excited that so-called excitons arise that can relax under the emission of light in the ground state.

The construction of possible optoelectronic devices is well known to those skilled in the art and is further exemplified herein. The proportion of emitter compound E in the emitter layer B may be 0.1 to 100 wt .-%. Accordingly, the emitter layer B can consist entirely or substantially of the emitter compound E or contain the emitter compound E only in small or large proportion among other compounds one or more host molecules W (Engl., "Hosts".) In LECs about the proportion of emitter compound E is is preferably 0.1 to 100% by weight in the emitter layer B. In many opto-electronic devices such as LECs, the proportion of emitter compound E in the emitter layer B is preferably more than 30% by weight, more than 40% Wt .-%, more than 50 wt .-%, more than 60 wt .-%, more than 70 wt .-%, more than 80 wt .-% or more than 90 wt .-%.

The emitter layer B may additionally contain a dye F. Any desired dye F or else a dye combination can be used here. The dye F can also be a fluorescent and / or phosphorescent dye F, which can shift the emission and / or absorption spectrum of the emitter layer B. Optionally, diphoton effects can also be used, therefore absorbing two photons with half the energy of the absorption maximum. By a fluorescent and / or phosphorescent dye F usually a bathochromic effect is achieved (for example by heat loss). However, a hypsochromic effect can also be achieved (for example by diphoton effects).

In addition, especially when the optoelectronic device is an LEC, the emitter layer B may contain an ionic liquid or a combination of two or more ionic liquids.

For example, such an ionic liquid or combination of two or more ionic liquids may be selected from the group consisting of:

Methyl imidazolium hexafluorophosphates (eg 1-alkyl-3-methylimidazolium hexafluorophosphates such as, for example, 1-methyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-propyl-3-methylimidazolium hexafluorophosphate, 1-butyl 3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolinium hexafluorophosphate), dimethylimidazolium hexafluorophosphates (eg 1-alkyl-2,3-dimethylimidazolium hexafluorophosphates such as, for example, 1-butyl-2,3-dimethyl- imidazolium hexafluorophosphate), 3-methyl-imidazolinohexafluorophosphates (eg, 1-methyl-methylidazolinohexafluorophosphates such as 1-methyl-3-methylimidazolinohexafluorophosphate, 1-ethyl-3-methyl-innidazolinohexafluorophosphate, 1-propyl-3-methyl-innidazolinohexafluorophosphate, 1 Butyl-3-methylimidazolinohexafluorophosphate, 1-pentyl-3-methyl-innidazolinohexafluorophosphate, 1-hexyl-3-methyl-innidazolinohexafluorophosphate), 1-butyl-1 - (3,3,4,4,5,5,6 , 6,7,7,8,8,8-tridecafluorooctyl) imidazolene hexafluorophosphate, 1-methyl-3- (3,3,4,4,5,5,6,6,7,7,8,8,8 -tridecafluorooctyl) -imidazoliumhexafluorophosphat,

1-Methyl-3-octyl-imidazolinohexafluorophosphate, methylimidazolium tetrafluoroborates (eg 1,3-dimethyl-innidazolene tetrafluoroborate, 1-ethyl-3-methyl-imidazolene tetrafluoroborate, 1-propyl-3-methyl-innidazolene tetrafluoroborate, 1-butyl-3-methyl 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium tetrafluoroborate, methylimidazolium trifluoromethanesulfonates (eg, 1-methyl-3-methylimidazolium trifluoromethanesulfonate , 1-ethyl-3-methylimidazolium trifluoronethanesulfonate, 1-propyl-3-methylimidazolium trifluoronethanesulfonate, 1-butyl-3-methylimidazolium trifluoronethanesulfonate), 1,2,3-tri- methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methyl- innidazoluenebis (pentafluoroethylsulfonyl) imide, 1-butyl-3-methylimidazolinyl-bis (trifluoromethylsulfonyl) imide, 1-butyl-3-methyl-innidazolinoethane-3,4-bisanesulfonate,

Tetrabutyl-ammonium-bis-trifluoromethanesulfonimidat, tetrabutyl ammonium methanesulfonate, tetrabutyl-amnnoniunn nonafluorobutanesulfonate

Tetrabutyl-aminoniunnheptadecafluorooetanesulfonate, tetrahexylammonium

tetrafluoroborate, tetrabutyl amnnoniunntrifluoronnethanesulfonat, tetrabutyl amnnoniunnbenzoate, (eg tetrabutyl amnnoniunnchlond, tetrabutyl amnnoniunnbronnid) tetrabutyl ammonium halides, 1-benzyl-3-methyl imidazoliunntetrafluoroborat, trihexyl-tetradecylphosphoniumhexafluorophosphate, tetrabutyl phosphoniumnnethanesulfonate, tetrabutyl phosphoniumtetrafluoroborate, tetrabutyl phosphonium bromide, 1-Butyl-3-methylpyndinium bis (t-fluoromethylsulfonyl) imide, 1-butyl-4-methylpyridinium hexafluorophosphate, 1-butyl-4-methylpyridinium tetrafluoroborate, sodium tetraphenylborate, tetrabutylaminotetraphenylborate, sodium tetrakis (1-imidazolyl) borate, and cesium tetraphenylborate. Additionally or alternatively, the emitter layer B may contain one or more electrolytes, such as one or a combination of several of the abovementioned salts. For example, KCF3SO3 can be used.

The emitter layer B may optionally be made by applying the emitter compound E or a composition Z containing it to a substrate (hence the surface of a component T of an opto-electronic device). This can be done by any method. The composition for producing an emitter layer B is preferably wet-chemically applied to a substrate (therefore the surface of a component T), for example by spin coating, dropcasting, slot casting, curtain casting, a rolling process or a printing process (eg inkjet printing). Engl, "inkjet printing"), gravure printing or knife coating).

Here, the emitter compound E or the composition Z may be dissolved in a vaporizable organic solvent such as a solvent selected from the group consisting of tetrahydrofuran, dioxane, chlorobenzene, Diethylenglykoldiethylether, diethylene glycol monoethyl ether, gamma-butyrolactone, N-methylpyrollidinone, ethoxyethanol, xylene, toluene , Anisole, phenetole, nitriles (eg acetonitrile), tetrahydrothiophene, benzonitrile, pyridine, trihydrofuran, triarylamine, water, methanol, ethanol, higher alcohols, thioethers, polyethylene glycol, polyethylene oxide, and PGMEA (propylene glycol monoethyl ether acetate). It is also possible to use combinations of two or more solvents.

Optionally, the liquid composition Z to be applied to the surface can be mixed with agents for improving the flow properties. Such agents are well known to those skilled in the art. For example, such an agent may be selected from the group consisting of Polyethyloxiden (polyethylene glycols), polyethylenediamines, polyacrylates (eg polymethylmethacrylate (PMMA), polyacrylic acid and its salts (superabsorbent)), substituted or unsubstituted polystyrenes (eg polyhydroxystyrene), polyvinyl alcohols, polyesters or polyurethanes , Polyvinylcarbazoles, polytriaryamines, polythiophenes and Polyvinylidenphenylenen. Combinations of two or more agents may also be used.

By applying the composition Z in the liquid phase, a wet phase containing the emitter compound (s) E or the composition Z is produced, which can subsequently be dried and / or cured by means of customary processes which are well-known in the art.

According to a particularly highly preferred embodiment, the optoelectronic device is a light emitting electrochemical cell (LEC) comprising the following layers:

 A) an anode layer A, preferably comprising indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene;

B) an emitter layer B containing the organochemical emitter compound E; and C) a cathode layer C, preferably comprising Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals.

An OLED, an LEC and an organic laser can be used as intended to produce light of a particular wavelength.

Accordingly, another aspect of the invention relates to a method of producing light of a particular wavelength, comprising the step of providing an opto-electronic device according to the present invention.

For example, the wavelength of the emitted light can also be adjusted to short-wave emission, so that blue light is emitted. Accordingly, the present invention also includes a method of producing blue, green, yellow, orange or red emission. By way of example, therefore, light in the range of 400-800 nm may be emitted, such as in the range of 400-500 nm, 450-550 nm, 500-600 nm, 550-650 nm, 600-700 nm, 650 -750 nm and / or 700-800 nm.

If the opto-electronic device according to the present invention is an OLED, it can also be used, for example, as a large-area light source, as a luminous wallpaper, luminous window, self-luminous label, self-luminous poster or flexible screen.

If the opto-electronic device according to the present invention is an OSC, it can also be used, for example, as a roll-up solar cell (for mobile applications such as smartphones, laptops, tablets, etc.), as an architectural element (eg wall or roof cladding element) or as Component in the traffic area (eg automotive, aircraft, train, and / or ship area) are used. Such products containing the optoelectronic device according to the invention are the subject of the present invention.

A further aspect of the invention relates to a composition comprising a Cu (I) complex having a structure according to one of the following formulas A or A 'and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic Apparatus and a method for generating light as described herein can be used. Examples of corresponding complexes without non-complexed ionic groups are also given in WO 2013/007707 (see, for example, Examples 1 -6 thereof)

bei der der L, L' und Z umfassende Ligand (L^AL') ein optional neutraler, zweizähniger Ligand ist, der über nicht-ionische Gruppen an das Cu gebunden ist; bei der der D, [B]_n, Z' und N^" umfassende Ligand (D^AN^~) über eine anionische Gruppe an das Cu gebunden ist; bei der D ein Rest ist, der mindestens einen Substituenten D^* ausgewählt aus der Gruppe bestehend aus einem divalenten Carben C^*, N, O, P, S, As und Sb aufweist oder aus D^* besteht, wobei D^* eine Bindung zu Cu eingeht,

wherein the L, L 'and Z-comprising ligand (L ^A L') is an optionally neutral, bidentate ligand bonded to the Cu via non-ionic groups; in which the D, [B] _n , Z 'and N ^" comprehensive ligand (D ^A N ^~ ) is bound via an anionic group to the Cu, wherein D is a radical containing at least one substituent D ^* selected from the group consisting of a divalent carbene C ^* , N, O, P, S, As and Sb or consists of D ^* , where D ^{* forms} a bond to Cu,

wherein D furthermore has a radical having up to 40 carbon atoms selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical, each optionally containing one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl radicals, linear, branched or cyclic heteroalkyl radicals, aryl radicals, heteroaryl radicals, linear, branched or cyclic alkenyl radicals , linear, branched or cyclic alkynyl radicals and other donor and acceptor groups such as amines, phosphines, carboxylates and their esters, and CF ₃ - may be substituted groups, wherein the substituents with each other and / or with the radical D optionally ei can form a cyclized and / or fused structure; wherein N ^{"is an} anionic nitrogen in which Z 'is R ^u -, -R ^U -NR ^U" , -NR ^{U "} -R ^U -, -R ^U -NR ^U" -R ^U -, -R ^u -SiR ^{u "} R ^u" R ^u -, -R ^u -SiR ^{u "} R ^u" -, - SiR ^{u "} R ^u" -, -R ^u -GeR ^{u "} R ^u" R ^u -, -R ^u -GeR ^{u "} R ^u" -, -GeR ^u R ^u -, R ^u -, -R ^u -OR ^u -, -R ^u -CO-R ^u -, - R ^u -CO-OR ^u -, - R ^u -O-CO-OR ^u -, -R ^u -O-CO-R ^u -, -OR ^u -, -R ^-CS-U R ^U -, -R ^u -CO-SR ^u -, -R ^u - S-CO-R ^u -, -R ^u -CO-NH-R ^u -, -R ^u -NH-CO-R ^u -, -R ^u -O-, -R ^u -SR ^u -, - SR ^u -, -R ^u -S-, -R ^u -SO- R ^u -, -SO-R ^u -, -R ^u -SO-, -R ^u -SO ₂ -R ^u -, -SO ₂ - R ^u - or -R ^u -SO ₂ -, wherein R ^u and R ^u are each independently a radical having up to 40 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroarylene radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups, such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ groups, where the substituents with one another and / or with the radical D can optionally form a cyclized and / or fused-on structure, wherein R ^u and R ^u are each independently a moiety of up to 40 carbon atoms, independently selected from the group consisting of hydrogen, halogen, -R ⁴ , -O-C (O), -COOH, -OR ', -NR 'R ^4', -SiR'R "R ', - GeR'R' R ^'", -SR', -SOR ', -SO ₂ R' and other donor and acceptor groups, such as carboxyl and their esters and CF ₃ groups, wherein R ', R * and R ^{r are} independently selected from the group consisting of H, OH, NH ₂ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci -20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2O heteroaryl, C _7- 32 arylalkyl, C6-3i-heteroarylalkyl, C8-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R ', R ^f, R'^", R ^u, R ^{u ',} R ^u" and R ^{u "} optionally lead to fused ring systems;

wherein each B is a divalent organic bridge independently selected from the group consisting of = CR ^Z -, -CR ^z R ^y -, -NR ^Z -, -O-, -SiR ^z R ^y -, -GeR ^z R ^y - , -S-, -S (O) - and -S (O) 2- or is a bond,

wherein R ^z and R ^{y are} independently selected from the group consisting of hydrogen, halo -OR ^x , -OC (O) -R ^x , -NR ^X R ^X , -SiR ^x R ^x R ^{x "} , -GeR ^x R ^x R ^x , -S R ^X , - SOR ^x and -SO ₂ R ^x ,

wherein R ^x , R ^x and R ^{x are} independently selected from H, OH, NH ₂ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, d-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C _7- 32-arylalkyl, C6-3i-heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R ^x, R ^y and R may also result in fused ring ^{systems, for} optionally, wherein by way of example B component of a Phenyl- and / or substituted phenyl units,

where several Bs may be the same or different,

with at least one carbon atom between N ^" and D ^* ,

wherein one or more substituents of D and / or N ^" with B may optionally form cyclic, aliphatic, conjugated, aromatic and / or fused systems in which T is CR ^W or nitrogen,

wherein R ^{w is} a radical selected from the group consisting of hydrogen, halogen, - R ^v , -OC (O) R ^v , -COOH, -OR ^v , -NR ^V R ^V , -SiR ^v R ^v R ^{v "} , -GeR ^v R ^v R ^v , -SR ^V , -SOR ^v , -SO ₂ R ^v and other donor and acceptor groups, such as carboxylates and their esters and CF ₃ groups,

wherein R ^v , R ^v and R ^{v are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^{V '} , NHR ^V R ^{v ""} , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20 alkyl, Ci-2O heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C _7- 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33-AI I ky a ry I a I ky I moiety and a C _7- 32-Heteroalkylarylalkylrest. wherein R ^v and R ^{v are} independently selected from the group consisting of OH, NH ₂ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2- 2o-alkenyl, Ci-io Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2O heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, C8-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest. where two or more of the radicals R ^v , R ^v , R ^v and R ^{w may} optionally also form one or more fused ring systems, where T may optionally form one or more B ring systems with one or more B;

where n is the integers from 1 to 9;

each of L and L 'is independently a substituent attached to the Cu, wherein L contains a substituent L ^* and L' contains a substituent L ' ^* , wherein L ^* and L' ^{* are} independently selected from the group consisting of a divalent carbene C ^* , N, O, P, S, As, and Sb; and L ^* and L ' ^* each form a bond to the Cu, where L contains one or more, preferably three, substituents attached to L ^* and wherein L 'contains one or more, preferably three, substituents which are bonded to L ^* ',

wherein the substituents bonded to L ^* and L ' ^* are each independently a substituent of up to 40 carbon atoms selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroarylene radical , a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ - groups, where the substituents may optionally form a cyclized and / or fused-together structure with one each attached to L ^* Substituent and a substituent attached to L ' ^* can be linked to one another via Z, in particular where the other substituents bonded to L ^* and L' ^{* are} each aryl radicals, wherein Z is -O-, a bond, -R ^ub - -R ^ub -NR ^ub -, -NR ^{ub "-R ub} -, -R ^ub -NR ^ub -R ^ub -, -R ^ub - SiR ^ub" R ^{ub "'} -R ^ub' , -R ^ub -SiR ^ub" R ^{ub "'} , -SiR ^ub" R ^{ub "'} -R ^ub- , -R ^ub -GeR ^ub" R ^{ub "'} -R ^ub' -, -R ^ub - GeR ^{ub "R ub '-,} -GeR ^ub" R ^{ub "-R ub} -, -R -OR ^{ub ub} -, -R ^ub -CO-R ^ub -, -R ^ub -CO- OR ^ub , -R ^ub -O-CO-OR ^ub , ^-Rub -O-CO-R ^ub -, -OR ^{ub '} , -R ^ub -CS-R ^ub -, -R ^ub -CO-SR ^ub , -R ^ub -S-CO- ^Rub- , ^-Rub - CO-NH- ^RUB -, ^-Rub -NH-CO- ^Rub- , ^-Rub -CO-NR ^{v "} -R ^ub -, -R ^ub -NR ^{v "-CO-R ub} -, -R ^ub -O-, -R ^ub - SR ^ub -, -SR ^{ub ',} -R ^ub -S-, -SO- ^ub -R R ^ub -, -SO-R ^{ub '} , -R ^ub -SO-, -R ^ub -SO ₂ -R ^ub -, -SO ₂ ^-Rub or ^-Rub -SO2- or Z is absent and thus none Bond between L and L 'is present, wherein R ^ub and R ^ub are each independently a radical having up to 40 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene est, a heteroarylene radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ groups, where the substituents may optionally form a cyclized and / or fused-together structure with each other, wherein R ^ub and R ^{ub are} independently another each represent a radical having up to 40 carbon atoms are independently selected from the group consisting of hydrogen, halogen, -R ^r, -OC (O) R ^r, -COOH, -OR ^r, -NR * ^{'R' ''} , - SiR '^' R '^"' ^, -GeR '^' R '^"" ^ -SR'^" , -SOR ^r , -SO ₂ R ^r and other donor and acceptor groups, such as Carbox ylates and their esters and CF ₃ groups, wherein R ^r , R ^r and R * are independently selected from the group consisting of H, OH, NH ₂ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci -20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o- Heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, C8-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R ^r, R ^''', R *, R ^ub, R ^{ub '} , R ^{ub "} and R ^ub" can optionally lead to fused ring systems; and wherein at least one of the ligands Ι_ ^Λ Ι_ 'and / or D ^A N ^" (therefore L, L', Z, D and / or [B] _n ) carries at least one non-complexed ionic group, in particular an ionic group selected from the group consisting of the group consisting of -SO 3 ^" , -PO 3 ^" , -COO ^" and -NH ₃ ⁺ , in particular wherein the ionic group is an SO 3 ^" .

Alternatively, two or more Z L and L 'may connect to each other.

 Z may also be absent so that L and L 'are each independently bound to the Cu.

In one embodiment, N ^" together with Z 'of the formula A or A' forms an anion of an unsaturated or aromatic N-heterocyclic moiety having 5 to 14 ring atoms which, after N-deprotonation of a residue selected from the group consisting of purinyl, Pyrryl, indyl, carbazolyl, triazolyl, benzotriazolyl, pyrazolyl, benzopyrazolyl, imidazolyl, benzimidazolyl, and tetrazolyl can be obtained and which may optionally be further substituted.

In one embodiment, the residue D of the D, [B] _n , Z 'and N ^" -composing ligand (N ^{" A} D) of the formula A or A' is selected from the group consisting of (wherein the ligand has not more than 20 carbon atoms ):

(i) a carbene C ^* which is part of a carbene ligand selected from the group consisting of

wobei die zwei Punkte„:" für ein divalentes Carben stehen, das an das Cu-Atom koordiniert, und die Verknüpfung zu B an einer der mit # gekennzeichneten Stellen stattfindet; wobei die andere die andere mit #- gekennzeichnete Bildungsstelle dann mit einem Rest ausgewählt aus der Gruppe bestehend aus Wasserstoff, Deuterium, Halogen -OR^s, -O-C(O)-R^s, -NR^SR^S , -SiR^sR^s R^s", -GeR^sR^s R^s , -SR⁸, -SOR^s und - SO₂R^s verbunden sein kann wobei R jeweils unabhängig ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, Deuterium, Halogen, -R^s -OR^s, -O-C(O)-R^s, -NR^SR^S , -SiR^sR^s R^s",- GeR^sR^s R^s , -SR⁸, -SOR^s und -SO₂R^s, wobei R^s, R^s und R^s unabhängig von einander ausgewählt sind aus Wasserstoff,

wherein the two dots ":" represent a divalent carbene which coordinates to the Cu atom and the linkage to B occurs at one of the # marked sites, the other one then selecting the other # - characterized formation site with a residue from the group consisting of hydrogen, deuterium, halogen, -OR ^s, -OC (O) -R ^s, -NR ^S R ^S, -SiR ^s R ^s R ^{s ",} -GeR ^s R ^s R ^s, -SR ^8, -SOR ^s and - SO ₂ R ^s may be connected wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, -R ^s -OR ^s , -OC (O) -R ^s , -NR ^s R ^s -SiR ^s R ^s R ^{s "} , - GeR ^s R ^s R ^s , -SR ⁸ , -SOR ^s and -SO ₂ R ^s , where R ^s , R ^s and R ^{s are} independently selected from hydrogen,

Deuterium, OH, NH _2, a halogen, a substituted or unsubstituted, linear, branched or cyclic _Ci-2 0 alkyl, _Ci-2 0 heteroalkyl, 0 ₂ - ₂ 0-

Alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R, R ^s , R ^s and R ^s can optionally also lead to fused ring systems; wherein Y is nitrogen or CR ^r , wherein R ^{r is} a radical selected from the group consisting of hydrogen, deuterium, halogen, -R ^q , -OC (O) R ^q , -COOH, -OR ^q , -NR ^q R ^q , -SiR ^q R ^{q q} R ^", - GeR ^q R ^q R ^q", -SR ^{q, q} -SOR, -SO ₂ R ^q and other donor and acceptor groups, such as carboxylates and their esters, and CF ₃ Groups wherein R ^q , R ^q and R ^{q are} independently selected from the group consisting of H, OH, NH ₂ , NR ^s R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20 alkyl, Ci-2O heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C _7- 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein two or more of R ^q, R ^q, R ^q and R ^r also perform optional fused ring systems where z is the integer 1 , 2, 3 or 4; an unsaturated or aromatic N-heterocyclic moiety having 4 to 8 ring atoms, the coordination to the Cu atom taking place via a nitrogen atom of the N-heterocyclic moiety selected from the group consisting of pyridyl, pyrimidyl, pyridazyl, pyrazyl, Pyranyl, coumaryl, pteridyl, thiophenyl, benzothiophenyl, furyl, benzofuryl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, thienothienyl, dithiaindacenyl, quinolyl, isoquinolyl, quinoxalyl, acridyl, azanaphthyl, phenanthrolyl, triazinyl, thienyl, thiadiazolyl, isoxazolyl, isothiazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, 1, 2,4-oxadiazolyl, 1, 2,4-thiadiazolyl, tetrazolyl, 1, 2,3,4-oxatriazolyl and 1,2,3,4- Thiatriazolyl, which optionally continues substituted and / or fused, and an N-heterocyclic selected from the group consisting of:

wobei die Verknüpfung zu B an der mit # gekennzeichneten Stelle stattfindet und * das Atom kennzeichnet, das die Komplexbindung eingeht, wobei Zi , Z₂, Z₃ und Z jeweils unabhängig voneinander ausgewählt CR¹ oder Stickstoff sind, wobei R¹ ein Rest, ausgewählt aus der Gruppe bestehend aus Wasserstoff, Deuterium, Halogen, -R^k, -OC(O)R^k, -COOH, -OR^k, -NR^kR^k , -SiR^kR^k R^k", - GeR^kR^k R^k", -SR^k, -SOR^k, -SO₂R^k und weiteren Donor- und Akzeptor-Gruppen, wie beispielsweise Carboxylaten und deren Estern und CF₃-Gruppen, wobei R^k, R^k und R^k unabhängig von einander ausgewählt sind aus der Gruppe bestehend aus H, OH, NH₂, NR^SR^S , NHR^S, einem Halogen, einem substituierten oder unsubstituierten, linearen, verzweigten oder zyklischen Ci-20-Alkyl-, Ci-2o- Heteroalkyl-, C2-2o-Alkenyl-, Ci-io-Heteroalkenylrest und einem substituierten oder unsubstituierten C6-2o-Aryl-, C_5-2o-Heteroaryl-, C_7-32-Arylalkyl-, C6-31 - Heteroarylalkyl-, Cs-33-Alkylarylalkylrest und einem C_7-32-Heteroalkylarylalkylrest, wobei der/die Reste R^k, R^k , R^k und R¹ optional auch zu anellierten Ringsystemen führen können,

wherein the linkage to B occurs at the position marked # and indicates the atom entering into the complex bond wherein Zi, Z ₂ , Z ₃ and Z are each independently selected from CR ¹ or nitrogen, wherein R ^{1 is} a radical from the group consisting of hydrogen, deuterium, halogen, -R ^k , -OC (O) R ^k , -COOH, -OR ^k , -NR ^k R ^k , -SiR ^k R ^k R ^{k "} , - GeR ^k R ^k R ^{k "} , -SR ^k , -SOR ^k , -SO ₂ R ^k and other donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ^k , R ^k and R ^{k are} independent of each other are selected from the group consisting of H, OH, NH ₂ , NR ^s R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-2o heteroalkyl, C2 -2O-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-31 - heteroarylalkyl, Cs-33- Alkylarylalkylres t and a C _7- 32-Heteroalkylarylalkylrest, the / R ^k, R ^k, R ^k and R ¹ may also result in fused ring systems, optionally,

(iii) a phosphanyl, arsenyl or antimony moiety of the form -ER'R ^J , wherein E is selected from the group consisting of P, As and Sb which coordinate to the Cu atom, where R ¹ and R ^j independently of one another in each case a radical selected from the group consisting of hydrogen, deuterium, halogen, -R ^k , -OC (O) R ^k , - COOH, -OR ^k , -NR ^k R ^k , - SiR ^k R ^k R ^{k ",} -GeR ^k R ^k R ^k", -SR ^{k, k} -SOR, -SO ₂ R ^k and another donor and acceptor groups, such as carboxylates and their esters, and CF ₃ groups , wherein R ^k , R ^k and R ^{k are} independently selected from the group consisting of H, OH, NH ₂ , NR ^s R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-2o heteroalkyl, C ₂ -2o alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C _7- 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, the / R ^h, R ^h, R ^{h '■} R' and R ^j and optionally can lead to fused ring systems,

In one embodiment, the carbene C ^{* of} the D, [B] _n , Z 'and N ^" -composing ligand (N ^{" A} D) of the formula A or A' is part of a structure selected from the group consisting of:

wobei die zwei Punkte „:" für ein divalentes Carben stehen, das an das Cu-Atom koordiniert, und die Struktur mit einer der mit # gekennzeichneten Stellen mit B verknüpft ist; wobei die andere die andere mit # gekennzeichnete Bildungsstelle dann mit einem Rest ausgewählt aus der Gruppe bestehend aus Wasserstoff, Halogen -OR^g, -O-C(O)-R^g, - NR^gR^g , -SiR^gR^g R^{g "},-GeR^gR^g R^{g "}, -SR⁹, -SOR⁹ und -SO₂R⁹, wobei R jeweils unabhängig ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, Deuterium, Halogen, -R⁹, -OR⁹, -O-C(O)-R⁹, -NR⁹R⁹ , -SiR⁹R^9'R^{9 "},-GeR⁹R⁹ R^{9 "}, -SR⁹, - SOR⁹ und -SO₂R⁹, wobei R^g, R^g und R^g unabhängig von einander ausgewählt sind aus H, OH, NH₂, NR^SR^S , NHR^S, einem Halogen, einem substituierten oder unsubstituierten, linearen, verzweigten oder zyklischen Ci-20-Alkyl-, Ci-20-Heteroalkyl-, C2-2o-Alkenyl-, CMO- Heteroalkenylrest und einem substituierten oder unsubstituierten C6-2o-Aryl-, C_5-2o- Heteroaryl-, C_7-32-Arylalkyl-, C6-3i-Heteroarylalkyl-, Cs-33-Alkylarylalkylrest und einem C_7- 32-Heteroalkylarylalkylrest, wobei die Reste R, R^g, R^g und R^g optional auch zu anellierten Ringsystemen führen können; und

wherein the two dots ":" represent a divalent carbene which coordinates to the Cu atom and the structure is linked to one of the sites marked # with B, the other one selecting the other site indicated by #, then with a residue from the group consisting of hydrogen, halogen, -OR ^g, -OC (O) -R ^g, - NR ^g R ^g, -SiR ^g R ^g R ^{g ',} -GeR ^g R ^g R ^g', -SR ^9, - SOR ⁹ and -SO ₂ R ⁹ , wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, -R ⁹ , -OR ⁹ , -OC (O) -R ⁹ , -NR ⁹ R ⁹ , - SiR ⁹ R ^{9 '} R ^{9 "} , -GeR ⁹ R ⁹ R ^9" , -SR ⁹ , - SOR ⁹ and -SO ₂ R ⁹ , wherein R ^g , R ^g and R ^{g are} independently selected from H, OH, NH ₂ , NR ^S R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl-, Ci-20-heteroalkyl, C2-2o-alkenyl, CMO Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2O heteroaryl, C ₇ 32 arylalkyl, heteroarylalkyl C6-3i -, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals may also lead to ^g fused ring systems R, R ^g, R ^g and R optional; and

where Y is nitrogen or CR ^f ,

wherein R ^{f is} a radical selected from the group consisting of hydrogen, deuterium, halogen, -R ^e , -OC (O) R ^e , -COOH, -OR ^e , -NR ^e R ^e , -SiR ^e R ^e R ^{e "-GeR e} R ^e R ^{e ',} -SR ^e, - SOR ^e, -SO 2 R ^e and other donor and acceptor groups, such as carboxylates and their esters, and CF ₃ groups, wherein R ^e, R ^e, and R ^{e are} independently selected from the group consisting of H, OH, NH ₂ , NR ^S R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20 heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, heteroarylalkyl C6-3i- , Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, the / R ^e, R ^e, R ^e and R ^f optionally may also result in fused ring systems,

where z stands for the integers 1, 2, 3 or 4.

In one embodiment, the ligand Ι_ ^Λ Ι_ 'of the formulas A and A' is a bidentate ligand of the form LG-L ', in which G is a substituted or unsubstituted C 1-6 -alkylene, C 2-8 -alkenylene- , C 2-8 alkynylene or arylene, -R ^d -NR ^d -, -NR ^{d "} -R ^d -, -R ^d -NR ^d -R ^d -, -R ^d -SiR ^d" R ^{d "} -R ^d -, -R ^d - SiR ^{d "} R ^d" -, -SiR ^{d "} R ^d" -, -R ^d -GeR ^{d "} R ^d" - R ^d -, -R ^d -GeR ^{d "} R ^d" - , -GeR ^{d "R d"} -, -R ^d, -R -OR ^{d d} -, - R ^d -CO-R ^d -, -R ^d -CO-OR ^d -, -R ^d -O-CO- OR ^d -, -R ^d -O-CO-R ^d -, -OR ^d -, -R ^d -CS-R ^d -, -R ^d - CO-SR ^d -, -R ^d -SCO-R ^d -, -R ^d -CO-NH-R ^d -, -R ^d -NH-CO-R ^d -, -R ^d -O-, - R ^d -SR ^d -, -SR ^d -, - R ^d -S-, -R ^d -SO-R ^d -, -SO-R ^d -, -R ^d -SO-, -R ^d -SO ₂ - R ^d -, -SO ₂ -R ^d -, or -R ^d -SO ₂ -, wherein R ^d and R ^d are each independently a radical having up to 20 carbon atoms selected from the group consisting of a linear, branched or a cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical, each optionally containing one or more of the substituents selected from the group consisting of halogens , Deuterium, linear, branched or cyclic alkyl radicals, linear, branched or cyclic heteroalkyl radicals, aryl radicals, heteroaryl radicals, linear, branched or cyclic alkenyl radicals, linear, branched or cyclic alkynyl radicals and a other donor and acceptor groups such as amines, phosphines, carboxylates and their esters and CF ₃ groups may be substituted, wherein the substituents with each other and / or with one or both of the radicals L and / or L 'optionally a cyclized and / or form anellated structure, wherein R ^d and R ^d are each independently a radical having up to 20 carbon atoms, independently of one another selected from the group consisting of hydrogen, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , -NR ^C R ^C , -SiR ^c R ^c R ^{c "} , -GeR ^c R ^c R ^c" , -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups, such as carboxylates and their esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NR ^s R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci- ₂ o-alkyl, Ci _-2 o-heteroalkyl, C _2-2 o-alkenyl, Ci-i o-Heteroalkenylrest and a substituted or unsubstituted C6-aryl _-2 o, C _5-2 o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 3 ₂ -Heteroalkylarylalkylrest, where the radicals R ^c , R ^{c '} , R ^{c "} , R ^d , R ^d' , R ^d" and R ^{d "may} optionally lead to fused ring systems; wherein L and L 'are substituents which are the same or different and which are independently selected from the group consisting of (wherein the ligand has not more than 20 carbon atoms): the fragment X ^b or an unsaturated or aromatic N-heterocyclic moiety having from 4 to 8 ring atoms selected from the group consisting of pyridyl, pyrimidyl, pyridazyl, pyrazyl, pyranyl, cumaryl, pteridyl, thiophenyl, benzothiophenyl, furyl, benzofuryl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, thienothienyl, dithiaindacenyl, Quinolyl, isoquinolyl, quinoxalyl, acridyl, azanaphthyl, phenanthrolyl, triazinyl, thienyl, thiadiazolyl, isoxazolyl, isothiazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, 1, 2,4-oxadiazolyl, 1, 2, 4-thiadiazolyl, tetrazolyl, 1, 2,3,4-oxatriazolyl and 1,2,3,4-thiatriazolyl, which are optionally further substituted and / or fused,

wherein the coordination to the Cu atom takes place via the nitrogen atom of the fragment X ^b or a nitrogen atom of the N-heterocyclic unit,

wherein the fragment X ^{b is} selected from the group consisting of:

 where the linkage to G takes place at the position marked # and * denotes the atom that undergoes complexation,

wherein Zi, Z ₂ , Z ₃ and Z are each independently CR ^az or nitrogen,

wherein R ^{az is} a radical selected from the group consisting of hydrogen, halogen, -R ^ay , -OC (O) R ^ay , -COOH, -OR ^ay , -NR ^ay R ^{ay '} , -SiR ^ay R ^ay R ^ay - GeR ^ay R ^ay R ^{ay "} , -SR ^ay , -SOR ^ay , -SO ₂ R ^ay and other donor and acceptor groups, such as carboxylates and their esters and CF ₃ groups, wherein R ^ay , R ^ay and R ^{ay are} independently selected from the group consisting of H, OH, NH ₂ , NR ^s R ^s , NHR ^s , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-2o alkyl, 2o-heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, C8-33-Alkylarylalkylrest and a C _7- 32 Heteroalkylarylalkylrest,

where the radicals R ^ay , R ^{ay '} , R ^{ay "} and R ^az can optionally also lead to fused ring systems,

a phosphanyl, arsenyl or antimony moiety of the form -ER'R ^j as defined above; and or

a group D containing the C ^* selected from the group consisting of:

wobei die zwei Punkte„:" für ein divalentes Carben stehen, das an das Cu-Atom koordiniert, und die Struktur mit einer der mit # gekennzeichneten Stellen mit B verknüpft ist;

wherein the two dots ":" represent a divalent carbene which coordinates to the Cu atom and the structure is linked to one of the sites marked # with B;

the other being the other education site indicated by # then having a radical selected from the group consisting of hydrogen, halogen, OR ^g, -OC (O) -R ^g, -NR ⁹ R ^9, -SiR ^g R ^g R ^{g ',} -GeR ^g R ^g R ^g', -SR ^9, -SOR ^9, and -SO ₂ R ⁹ substituted can be,

wherein the radicals R, R ⁹ , R ⁹ , R ⁹ and Y and z are as defined above. Another aspect of the invention relates to a composition comprising a Cu (I) complex having a structure according to the following formula B and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein. Examples of such complexes are also shown in WO 2013/007707 (Formulas I and A thereof) and in WO 2010/031485 (see, for example, Formulas II, IV and VI-IX thereof).

Formula B wherein the L, L 'and Z-comprising ligand (L ^A L') is an optionally neutral, bidentate ligand bonded to the Cu via non-ionic groups; in which the ligand (Ν ^Λ Ν) comprising the ring systems A and A 'and the bridging ligand Z' can optionally be bonded to the Cu via an anionic group, the ligand Ν ^Λ Ν then neutralizing the positive charge of the Cu (I) can;

wherein the ring systems A and A 'have one of the following structures:

wherein Zi, Z ₂ and Z _{3 are} each independently of the other nitrogen or CR, wherein R is independently selected from the group consisting of -H, -D, -F, -Cl, -Br, -I, -CN, -NO ₂ , -SO, -SO ₂ , -OH, -OR ^a , -SH, -SR ^a , -R ^a -NR ¹ R ² , -NR ¹ R ² , -R ^a - C (= O) R ¹ , -C (= O) R ¹ , -R ^a -SiR ¹ R ² R ³ , -SiR ¹ R ² R ³ , -R ^a -GeR ¹ R ² R ³ , -GeR ¹ R ² R ³ , R ^a - SeR ¹ R ² R ³ , -SeR ¹ R ² R ³ , -R ^a -R ¹ C =CR ² R ³ , -R ¹ C =CR ² R ³ , -R ^a -C -CCR ¹ , -C ^ CR ¹ , -R ^a -C = O, -R ^a -C = S, -R ^a -C = Se, -R ^a -C = NR ¹ , -C = O, -C = S, - C = Se, -C = NR ¹ , -R ^a -CN = R ¹ , -CN = R ¹ , - R ^a -POR ¹ R ² R ³ , -R ^a -N = R ⁴ , -CO-NH- R ¹ , -R ^a -CO-NH-R ¹ , -NH-CO-R ¹ , -R ^a -NH-CO-R ¹ , wherein R ¹ , R ² and R ^{3 are} independently selected from the group consisting of H, D, F, I, Br, Cl, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms M can optionally be replaced by D, F, Cl, Br, I or CN, wherein R ^{4 is} selected from the group consisting of an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms optionally by D, F, Cl , Br, I or CN may be substituted and which may optionally be substituted with one or more aromatic or heteroaromatic rings wherein R ^{a is} selected from the group consisting of a substituted or unsubstituted C 1-6 alkylene, C 2-8 alkenylene , C 2-8 -alkynylene or arylene radical, -R ^a -NR ^{a '} -, -NR ^a -R ^a -, -R ^a -NR ^a -R ^a -, -R ^a' -SiR ^{a "} R ^a"" -R ^a" -, -R ^{a '} -SiR ^{a "} R ^a"" -, -SiR ^a" R ^{a ""} - R ^a -, - R ^a' - OR ^{a "} -, -R ^{a '} --CO -R ^{a "} -, -R ^{a '} -CO-OR ^a" -, -R ^a' -O-CO-OR ^{a "} -, -R ^{a '} -O-CO-R ^a" -, -OR ^{a "} , -R ^a -CS-R ^{a "} , -R ^{a '} -CO-SR ^a" -, -R ^a' -S-CO-R ^{a "} -, -R ^{a '} -CO-NH-R ^a" - R ^{a '} -NH-CO-R ^{a "} -, -R ^a' -O-, -R ^{a '} -SR ^a" -, -SR ^{a "} -, -R ^a' -S-, -R ^{a '-SO-R a "-,} -SO-R ^a' -, ^{-Ra '-SO-,} -R ^a' SO ₂ - R ^{a "} -, -SO ₂ -R ^a" - and -R ^{a '} -SO ₂ - is, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups, such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ groups, where the substituents with one another and / or with the radical Z 'can optionally form a cyclized and / or fused-on structure in which R ^a and R ^a are each independently a radical having up to 20 carbon atoms, independently of one another selected from the group consisting of hydrogen, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , -NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups, such as carboxyl and their esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^{a '} , NR ^{a "'} R ^a"" , a Halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-2o heteroalkyl, C2-2o alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, _5- 2o C-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33-AI I ky a ry I a I ky I moiety and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R ^c , R ^c , R ^{c "} , R ^a , R ^a" , R ^{a "} and R ^a"" can optionally also lead to fused ring systems, wherein two or more adjacent substituents may together form a mono-, di-, tri- or polycyclic, aliphatic, aromatic or heteroaromatic ring system; and

wherein Y is O, S or NR, wherein R is as defined above; wherein Z 'is BR ¹ R ² , wherein R ¹ and R ^{2 are} as defined above and B is a boron atom, in particular wherein Z' is selected from the group consisting of H ₂ B, BPh ₂ , B (CH ₃ ) ₂ and B (NR ¹ R ² ) ₂ , wherein Ph is a phenyl radical, wherein R ¹ and R ^{2 are} as defined above and B is a boron atom, in particular wherein Z 'is selected from the group consisting of H ₂ B, BPh ₂ , B (CH ₃ ) ₂ and B (NR ¹ R ² ) ₂ , where Ph is a phenyl radical, where " ^* " denotes the atom that undergoes complex binding and "#" denotes the atom that is linked to the second via Z ' Unit in which L and L 'may be as defined above under formula A, wherein Z may be as defined above under formula A and / or a radical is selected from the group consisting of -R ^ub - -R ^ub -NR ^ub , -NR ^{ub " -Rub-} , ^-Rub -NR ^{ub -Rub-} , ^-Rub - SiR ^ub" R ^{ub " -Rub} -, ^-Rub -SiR ^ub" R ^{ub "} -, -SiR ^{ub "} R ^{ub" -Rub-} , ^-Rub -OR ^ub- , -R ^ub -CO-R ^ub- , -R ^ub -CO- OR ^ub- , -R ^ub -O-CO-OR ^{u b} -, -R ^ub -O-CO-R ^ub -, -OR ^ub -, -R ^ub -CS-R ^ub -, -R ^ub -CO-SR ^ub -, - R ^ub -S-CO-R ^ub -, -R ^ub -CO-NH-R ^ub -, -R ^ub -NH-CO-R ^ub -, -R ^ub -O-, -R ^ub -SR ^ub -, -SR ^ub -, - R ^ub - S-, R- ^{sub- S} O ^-Rub -, -SO- ^Rub- , ^-Rub -SO-, ^-Rub -SO ₂ ^-Rub- , -SO ₂ ^{-Rub '} or ^-Rub - SO ₂ -, wherein R ^ub and R ^ub are each independently a radical having up to 40 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroarylene radical , a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups such as, for example, amines, phosphines, carboxylates and their esters and CF ₃ groups, where the substituents with one another and / or with the radical Z can optionally form a cyclized and / or fused structure, where R ^{ub "} and R ^ub" are each independently a radical of up to 40 carbon atoms, independently selected from the group consisting of hydrogen, halogen, -R ^r , -OC (O) R ^r , -COOH, -OR ^r , -NR * ^' R'^"", - SiR ^'' R ^{'''^ -SR"',} -SOR ^r, -SO ₂ R ^r and other donor and acceptor groups, such as carboxylates and their esters, and CF ₃ groups, where R ^r, R ^r and R * are independently selected from the group consisting of H, OH, NH ₂ , NHR ^{a "} , NR ^a"' R ^{a ""} , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci -20-alkyl, Ci-2o-heteroalkyl, C2-2o alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o- Aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33-AI I ky a ry I a I ky I moiety and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R may also result in fused ring systems, ^r, R ^''', R ^4, R ^{ub, ub R',} R ^{ub "and} R ^ub" optional; and wherein at least one of Z or Z 'is substituted by at least one non-complexed ionic group, preferably substituted by an ammonium group, a carboxyl group, a sulfonate group, a phosphonate group, in particular with --SO 3 ^'' .

wobei Me für einen Methylrest und Ph für einen Phenylrest steht. Ein weiterer Aspekt der Erfindung betrifft eine Zusammensetzung enthaltend einen Metall(l)-Komplex, der eine Struktur gemäß der folgenden Formel C aufweist und in Analogie zu den oben beschriebenen Komplexen, in einer lichtemittierenden Schicht S, in einer opto-elektronischen Vorrichtung und einem Verfahren zur Erzeugung von Licht wie hierin beschrieben verwendet werden kann. Beispiele für derartige Komplexe sind auch in WO 2014/102079 (siehe beispielsweise Formeln A und l-IX hieraus) gezeigt.

The following examples illustrate these ligands Ν ^Λ Ν:

where Me is a methyl radical and Ph is a phenyl radical. Another aspect of the invention relates to a composition comprising a metal (I) complex having a structure according to the following formula C and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein. Examples of such complexes are also shown in WO 2014/102079 (see, for example, Formulas A and I-IX thereof).

Formula C wherein M and M 'are independently selected from the group consisting of Cu, Ag and Au, in particular both are each Cu; wherein X and X 'are independently selected from the group consisting of Cl, Br, I, CN, OCN, SCN, alkynyl and azide; wherein the ligands (EnD) comprising E, Y, Z, Q and D and the ligands (E'nD ') comprising the Ε', Υ ', Ζ', Q 'and D' are each a bidentate ligand, where E and E 'are each independently either RR'E ^* , where E ^{* is} N, P, As or Sb, where N is or is not an imine nitrogen or part of an N-heteroaromatic ring, or E and E each independently is RE ^* , where E ^{* is} a divalent carbene C ^* , O or S, where R and R 'are each independently selected from the group consisting of hydrogen, halogen, deuterium, -R ¹ , -OC (O) R ¹ , -COOH, -OR ¹ , - NR ¹ R ¹ , -SiR ¹ R ¹ R ¹ -SR ¹ , -SOR ¹ , -SO ₂ R ¹ and other donor and acceptor groups, such as Carboxylates and their esters and CF ₃ groups, wherein R ¹ , R ¹ and R ^{1 are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, lin orene, branched or cyclic Ci-20-alkyl, Ci-20-Heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-Heteroaryl- , C _7- 32-arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein R ^x and R ^{y are} independently selected from the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o alkenyl, Ci-io -Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32 -Heteroalkylarylalkylrest, wherein the radicals R ¹ , R ¹ , R ¹ , R and R 'may optionally also lead to fused ring systems; where D and D 'are each independently either R "R"' D *, where D * is N, P, As or Sb, where N is or is not an imine nitrogen or part of an N-heteroaromatic ring, or D and D 'are each independently R "D *, where D * is a divalent carbene C *, O or S, where R" and R'"are each independently selected from the group consisting of hydrogen, halogen, and deuterium , -R ² , -OC (O) R ² , -COOH, -OR ² , - NR ² R ² , -SiR ² R ² R ^{2 "} -SR ² , -SOR ² , -SO ₂ R ² and further donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ² , R ² and R ^{2 are} independently selected from the group consisting of H, OH, NH ₂ , NHR ¹ , NR ¹ R ¹ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2O aryl, _5- 2o C-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, the / R ^2, R ^2, R ² and R "and R '" may optionally also lead to fused ring systems; where D and E are different or similar; wherein Q, Y, Z, Q ', Y' and Z 'independently of one another are each selected from the group consisting of a substituted or unsubstituted Ci-g-alkylene, C2-8- alkenylene, C _2- 8 alkynylene - or arylene radical, -R ^a -NR ^a -, -NR ^{a '} - R ^a -, -R ^a -NR ^a' - R ^a -, -R ^a - SiR ^{a "} R ^a" -R ^a -, -R ^a -SiR ^{a "} R ^{a '} -, -SiR ^a" R ^{a "} - R ^a -, -R ^a -OR ^a -, -R ^a -CO-R ^a -, -R ^a -CO-OR ^a -, -R ^a - O-CO-OR ^a -, -R ^a -O-CO-R ^a -, -OR ^a -, -R ^a -CS-R ^a -, R ^a -CO-SR ^a -, -R ^a -S-CO-R ^a -, -R ^a - CO-NH-R ^a -, -R ^a -NH-CO-R ^a -, -R ^a -O-, -R ^a -SR ^a -, -SR ^a -, -R ^a -S-, -R ^a -SO-R ^a -, -SO-R ^{3 '} -, - R ^a -SO-, -R ^a -SO ₂ -R ^a -, -SO ₂ -R ^a -, or -R ^a -SO ₂ -, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms selected from the A group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical, each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl radicals, linear, ver branched or cyclic heteroalkyl radicals, aryl radicals, heteroaryl radicals, linear, branched or cyclic alkenyl radicals, linear, branched or cyclic alkynyl radicals and other donor and acceptor groups such as amines, phosphines, carboxylates and their esters and CF ₃ groups may be substituted, the Substituents with one another and / or with the radical D can optionally form a cyclized and / or fused structure, where R ^a and R ^a are each independently a radical having up to 20 carbon atoms, independently selected from the group consisting of hydrogen, deuterium, Halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , - NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and others Donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ¹ , NR ¹ R ¹ , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci _-2 o alkyl, Ci _-2 o-heteroalkyl, C _2-2 o alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6 o- _-2 aryl, C _5-2 o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C ₇ 3 ₂ -Heteroalkylarylalkylrest, where the radicals R ^c , R ^{c '} , R ^{c "} , R ^a , R ^a' , R ^a" and R ^{a "} can optionally also lead to fused ring systems, and where at least one of the radicals Q, Z, Y, Q ' , Z 'and / or Y' is substituted with at least one non-complexed ionic group, preferably with an ammonium group, a carboxyl group, a sulfonate group and / or a phosphonate group, in particular with -SO 3 ^" substituted.

Optionally, the two bidentate ligands EnD and E'nD 'can also be linked to one another via a spacer unit S (for example a Ci-io-alkylene group), resulting in a tetradentate ligand.

Optionally, an improvement in the solubility of the metal complex can be achieved by at least one of the ligands EnD and E'nD 'carries a corresponding substituent.

Another aspect of the invention relates to a composition comprising a metal (I) complex having a structure according to the following formula D and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein.

Examples of such complexes are also shown in European Patent Application No. 14164815.

Formula D wherein M and M 'are independently selected from the group consisting of Cu, Ag and Au, especially both are Cu; wherein X and X 'are independently halides, especially selected from the group consisting of Cl, Br, I, or pseudohalides; wherein E 'and E "are independently selected from the group consisting of P, As and Sb, wherein R, R', R" and R '"are independently selected from the group consisting of optionally substituted alkyl groups. , Aryl, heteroaryl and alkoxy radicals each having up to 20 carbon atoms, wherein N is nitrogen, wherein Y and Y 'of the ring systems G1 and G2 are each independently selected from the group consisting of a substituted or unsubstituted C 1-6 Alkylene, C2-8 alkenylene, C2-8 alkynylene or arylene radical, = R ^a -

NR ^{a "} -, = NR ^a -, = R ^a -NR ^a -R ^a -, = R ^a -SiR ^a" R ^{a "} -R ^{a '} -, = R ^a -SiR ^a" R ^{a "} -, = R ^a -OR ^a -, = R ^a -CO-R ^a -,

= R ^a -CO-OR ^a -, = R ^a -O-CO-OR ^a -, = R ^a -O-CO-R ^a -, -OR ^a -, = R ^a -CS-R ^a -, = R ^a -CO-SR ^a -,

= R ^a -S-CO-R ^a -, = R ^a -CO-NH-R ^a -, = R ^a -NH-CO-R ^a -, = R ^a -O-, = R ^a -SR ^a - , = R ^a -S-, = R ^a -SO- R ^a -, = R ^a -SO-, = R ^a -SO ₂ -R ^a - and = R ^a -SO ₂ - is, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical, each optionally containing one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl radicals, linear, branched or cyclic heteroalkyl radicals, aryl radicals, heteroaryl radicals, linear , branched or cyclic alkenyl radicals, linear, branched or cyclic alkynyl radicals, and other donor and acceptor groups such as amines, phosphines, carboxylates and their esters and CF ₃ groups, where the substituents optionally cyclize with one another e and / or fused to form structure, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, independently selected from the group consisting of hydrogen, deuterium, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , - NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups, such as carboxylates and their esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl , C _7- 32-arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein R ^x and R ^y are selected independently of each other a Us the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2O aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, where the radicals R ^c , R ^{c '} , R ^{c "} , R ^a , R ^a' , R ^a" and R ^{a "} can optionally also lead to fused ring systems; in the case of B and B 'each independently of one another bridging a chain length of at least 2 and at most 17 atoms,

wherein the members of -CH ₂ -, -CHR ¹ -, -CR ¹ R ² -, -SiR ¹ R ² -, -GeR ¹ R ² -, -O-, -S-, -Se-, -NR ¹ -, -PR ¹ - and / or -AsR ¹ - may exist,

wherein R ¹ and R ² each independently represent a group selected from the group consisting of alkyl, aryl, heteroaryl, -OR ³ , -SR ³ , -SeR ³ , -H and -D each having up to 20 carbon atoms wherein R ^{3 is} an alkyl, aryl, heteroaryl, each having up to 20 carbon atoms, -H or -D; and

wherein at least one of R-R '''and / or G1 and / or G1 is substituted with at least one non-complexed ionic group, preferably substituted with an ammonium group, a carboxyl group, a sulfonate group, a phosphonate group, especially with -SO 3 ^' ,

The ring systems G1 and G2 are each preferably a five- or six-membered heteroaromatic ring system which is optionally substituted by further radicals such as R, R '; R ", R '", R ^a and / or R ^{a may be} substituted or fused with other aromatic rings.

A further aspect of the invention relates to a composition comprising a metal (I) complex having a structure according to the following formula E and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein. Examples of such complexes are also shown in WO 2013/014066 (see, for example, Formula IV thereof).

Formula E wherein M and M 'are independently selected from the group consisting of Cu, Ag and Au, especially both Cu; wherein X and X 'are independently selected from the group consisting of Cl, Br, I, CN, OCN, SCN, di-alkoxy and azide; the ligands comprising the E, Y, Z and D (EnD) and the ligands (E'nD ') comprising the Ε', Υ ', Z' and D 'are each a bidentate ligand; where E and E 'are each independently either RR'E ^* , where E ^{* is} N, P, As or Sb, where N is or is not an imine nitrogen or part of an N-heteroaromatic ring, or E and E 'are each independently RE ^* , where E ^{* is} a divalent carbene C ^* , O or S, where R and R' are each independently selected from the group consisting of hydrogen, halogen, deuterium, -R ¹ , -OC (O) R ¹ , -COOH, -OR ¹ , - NR ¹ R ¹ , -SiR ¹ R ¹ R ¹ -SR ¹ , -SOR ¹ , -SO ₂ R ¹ and other donor and acceptor groups, such as Carboxylates and their esters and CF ₃ groups,

wherein R ¹ , R ¹ and R ^{1 are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20 -Alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein R ^x and R ^y are independently selected from the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein the / the radicals R ¹ , R ¹ , R ¹ and R and R 'can optionally also lead to fused ring systems; where D and D 'are each independently either R "R"' D ^* , where D ^{* is} N, P, As or Sb, where N is or is not an imine nitrogen or part of an N-heteroaromatic ring, or D and D 'are each independently R "D ^* , where D ^{* is} a divalent carbene C ^* , O or S, wherein R" and R'"are each independently selected from the group consisting of hydrogen, halogen, deuterium , -R ² , -OC (O) R ² , -COOH, -OR ² , - NR ² R ² , -SiR ² R ² R ^{2 "} -SR ² , -SOR ² , -SO ₂ R ² and further donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ² , R ² and R ^{2 are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o- Aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, the / R ^2, R ² , R ² and R "and R '" can optionally also lead to fused ring systems;

where D and E are different or similar;

wherein Y, Z, Y 'and Z' are each independently selected from the group consisting of a substituted or unsubstituted C 1-6 -alkylene, C 2-8 -alkenylene, C _2- 8 alkynylene, or arylene, -R ^a -NR ^a -, -NR ^{a '-R a} -, -R ^a -NR ^a -R ^a -, -R ^a -SiR ^{a "R a"} -R ^a -, - R ^a -SiR ^{a "} R ^{a '} -, -SiR ^a" R ^{a "} - R ^a -, -R ^a -OR ^a -, -R ^a -CO-R ^a -, -R ^a -CO -OR ^a -, -R ^a -O-CO-OR ^a -, - R ^a -O-CO-R ^a -, -OR ^{a '} , -R ^a -CS-R ^a -, -R ^a -CO- SR ^a -, -R ^a -SCO-R ^a -, -R ^a -CO-NH-R ^a -, -R ^a - NH-CO-R ^a -, -R ^a -CO-NR ^x -R ^a -, -R ^a -NR ^x -CO-R ^a -, -R ^a -O-, -R ^a -SR ^a -, -SR ^{a '} , -R ^a -S-, -R ^a - SO-R ^a -, -SO-R ^{3 '} , -R ^a -SO-, -R ^a -SO ₂ -R ^a -, -SO ₂ -R ^a' or -R ^a -SO ₂ -, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical, each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl radicals, linear, branched or cyclic heteroalkyl radicals, aryl radicals, heteroaryl radicals, linear, branched or cyclic alkenyl radicals, linear, branched or cyclic alkynyl radicals and other donor and acceptor groups such as Amines, phosphines, carboxylates and their esters and CF ₃ groups, may be substituted, wherein the substituents with each other and / or with the radical D may optionally form a cyclized and / or fused structure, wherein R ^a and R ^a independently of one another Are radicals having up to 20 carbon atoms, independently selected from the group consisting of hydrogen, deuterium, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , - NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci- ₂ o-alkyl , Ci _-2 o-heteroalkyl, C _2-2 o alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-aryl _-2 o, C _5-2 o-heteroaryl, C _7- 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C ₇ 3 ₂ -Heteroalkylarylalkylrest, where the radicals R ^c , R ^c , R ^{c "} , R ^a , R ^a , R ^a" , R ^a can optionally also lead to fused ring systems; and wherein at least one of Z, Y, Y 'or Z' with at least one non-complexed ionic group is substituted, is preferably substituted with an ammonium group, a carboxyl group, a sulfonate group, a phosphonate group, in particular with -SO3 ^".

Optionally, the two bidentate ligands EnD and E'nD 'can also be linked to one another via a spacer unit S (for example a Ci-io-alkylene group), resulting in a tetradentate ligand.

Optionally, an improvement in the solubility of the metal complex can be achieved by at least one of the ligands EnD and E'nD 'carries a corresponding substituent.

Another aspect of the invention relates to a composition comprising a metal (I) complex having a structure according to the following formula F and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein. Examples of such complexes are also shown in WO 2013/017675 (see, for example, Formula A thereof).

Formula F wherein X and X 'are each independently selected from the group consisting of Cl, Br, I, CN, OCN, SCN, C 1-10 alkynyl and azide; where Z and Z 'independently represent a covalent bridge comprising at least two carbon and / or nitrogen atoms, where P is phosphorus and N is nitrogen; in which the ligand (PnN) comprising P, Z and N and the ligand (ΡηΝ 'comprising P, Z' and N) is in each case an N-heterocycle-substituted phosphine ligand which has a structure according to formula G:

Formula G wherein P is phosphorus and N is nitrogen;

wherein E is a carbon or nitrogen atom;

wherein E 'is a carbon or nitrogen atom which is not bonded to a hydrogen atom; wherein the dotted bond is a single or double bond; wherein R is an optionally substituted, optionally branched Ci-20-alkyl radical, preferably a C6-2o-alkyl radical or an optionally alkylated C6-2o-aryl radical, in particular phenyl, wherein a substitution in this case is a substitution with a or more halogens (eg, F, Cl, Br, and / or I), silane groups, ether groups, or optionally in turn substituted alkyl, alkenyl, and / or alkynyl groups; in which R 'and R "are independently selected from the group consisting of alkyl groups, preferably C6-2o-alkyl groups, which may also be branched or cyclic, or

 Aryl or heteroaryl groups which may be optionally substituted with alkyl groups, halogens (e.g., F, Cl, Br and / or I), silane groups or ether groups,

wherein R 'and R "are each directly attached to the phosphorus atom of the phosphine ligand, wherein R'" is selected from the group consisting of alkyl groups, preferably C6-2o-alkyl groups, which are also branched or cyclic or aryl or heteroaryl groups, which may optionally be substituted by alkyl groups, halogens (eg, F, Cl, Br and / or I), silane groups or ether groups,

wherein R '"with Z can also form a ring system, therefore an aliphatic or aromatic heterocycle, wherein Z, Z' and Z ^x are each independently selected from the group consisting of a substituted or unsubstituted Ci-g-alkylene, C2 -8-alkenylene, C _2- 8 alkynylene, or arylene, -R ^a -NR ^a -, -NR ^{a '-R a} -, -R ^a -NR ^a' -R ^a -, -R ^a -SiR ^{a "} R ^a" -R ^a -, - R ^a -SiR ^{a "} R ^{a '} -, -SiR ^a" R ^{a "} - R ^a -, -R ^a -OR ^a -, -R ^a -CO-R ^a -, R ^a -CO-OR ^a -, -R ^a -O-CO-OR ^a -, - R ^a -O-CO-R ^a -, -OR ^a -, -R ^a -CS-R ^a - , -R ^a -CO-SR ^a -, -R ^a -S-CO-R ^a -, -R ^a -CO-NH-R ^a -, -R ^a - NH-CO-R ^a -, -R ^a -O-, -R ^a -SR ^a -, -SR ^{a '} , -R ^a -S-, -R ^a -SO-R ^a -, -SO-R ^3' -, -R ^a -SO-, - R ^a -SO ₂ - R ^a -, -SO ₂ -R ^{a '} , -R ^a -CO-NR ^a -R ^a -, -R ^a -NR ^a -CO-R ^a -, and -R ^a -SO ₂ - is, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroaryl radical, a linear, branched or cyclic alkenylene radical and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ - groups, where the substituents may optionally form a cyclized and / or fused structure with each other, wherein R ^a and R ^a independently each are each a radical having up to 20 carbon atoms, independently of one another selected from the group consisting of hydrogen, deuterium, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , - NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups such as carboxylates and their Esters and CF ₃ groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear , branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, _7- C 32 arylalkyl, C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein R ^x and R ^y are independently selected from each other from the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-heteroalkenyl and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl , C _7- 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein the radicals R ^c , R ^{c '} , R ^{c "} , R ^a , R ^a' , R ^a" and R ^{a "} can optionally also lead to fused ring systems, and wherein at least one of Z or Z 'with at least one not Complexed ionic group is substituted, preferably with an ammonium group, a carboxyl group, a sulfonate group, a phosphonate group, in particular with - SO3 ^"is substituted. Another aspect of the invention relates to a composition comprising a Cu (I) complex having a structure according to the following formula H and in analogy to the complexes described above, in a light-emitting layer S, in an opto-electronic device and a method for generating light as described herein.

Examples of such complexes are also shown in WO 2013/072508 (see, for example, Formula A thereof), WO 2010/149748 (see, for example, Formula A thereof), and WO 2013/001086 (see, for example, Formula A thereof).

bei der X und X^* jeweils unabhängig von einender ausgewählt sind aus der Gruppe bestehend aus Cl, Br, I, CN, OCN, SCN, Ci.io-Alkinyl und Azid;

wherein X and X ^{* are} each independently selected from the group consisting of Cl, Br, I, CN, OCN, SCN, C 1-10 alkynyl and azide;

in the case of N ^*, a nitrogen atom which bonds with Cu; wherein E is RR'E ^* , where E ^{* is} N, P, As or Sb, where N is or is not an imine nitrogen atom or part of an N-heteroaromatic ring, or E RE ^* , where E ^{* is} a divalent carbene C ^* , O or S, where R and R 'are each independently selected from the group consisting of hydrogen, halogen, deuterium, -R ¹ , -OC (O) R ¹ , -COOH, -OR ¹ , - NR ¹ R ¹ , -SiR ¹ R ¹ R ¹ -SR ¹ , -SOR ¹ , -SO ₂ R ¹ and other donor and acceptor groups such as carboxylates and their esters and CF ₃ groups, wherein R ¹ R ¹ and R ^{1 are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl , Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C6- 3i-heteroarylalkyl, Cs-33 alkylarylalkylr est and a C _7- 32-Heteroalkylarylalkylrest, wherein R ^x and R ^y are selected independently from the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20 alkyl, Ci-20-heteroalkyl C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C 6-31 - heteroarylalkyl, C8 -33-Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest, wherein the / the radicals R ^1, R ^1, R ¹ and R and R may also lead to fused ring systems'optional;

Z is a covalent bridge comprising at least two carbon and / or nitrogen atoms; wherein the ligands L and L 'are each independently any organic ligand of from 1 to 20 carbon atoms, preferably containing one or more groups selected from the group consisting of -OC (O) R ^c , -COOH, -OR ^c , -NR ^C R ^C , -SiR ^c R ^c R ^{c "} -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups such as carboxylates and their esters, CF ₃ groups, phosphorus -, arsenic- or antimony-containing groups, wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^{a "} , NR ^a" R ^{a "} , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20 alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C _7- 32-arylalkyl, C6-3i-heteroarylalkyl, Cs-33- alkylarylalkyl residue and a C _7- 32-Heteroalkylarylalkylrest,

where the radicals R ^c , R ^{c '} , R ^{c "} , R ^d , R ^d' , R ^d" and R ^{d "} can optionally also lead to fused ring systems, where L and L 'are also bonded together and as in formula A above or as defined below according to formula K, in which the N ^* , Z and E-comprising ligand (EnN ^* ) may be a bidentate ligand according to the structure of formula K:

 Formula K wherein Y is a carbon or nitrogen atom;

wherein Y 'is a carbon or nitrogen atom substituted with a hydrogen atom;

wherein E ^{* is} selected from the group consisting of P, N, As, Sb, a divalent carbene C ^* , O and S;

wherein the dotted bond is a single or double bond;

wherein N represents a nitrogen atom incorporated in an imine group, the

Component of a heteroaromatic group comprising N, Y, Y ^' and Z ^x , wherein the heteroaromatic group is preferably selected from the group consisting of pyridyl, pyrimidyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, which may be optionally substituted (for example with one or more of Substituents of the abovementioned group) and / or may be fused to other groups of the complex in which R ^u and R ^{v are} independently selected from the group consisting of alkyl groups, preferably C 6-2o-alkyl groups, which may also be branched or cyclic, or aryl or heteroaryl groups which may be optionally substituted with alkyl groups, halogens (eg, F, Cl, Br and / or I), silane or ether groups;

wherein Z and Z ^x are each independently selected from the group consisting of a substituted or unsubstituted C 1-6 alkylene, C _2-8 alkenylene, C _2-8 alkynylene or arylene radical, -R ^a -NR ^a , -NR ^{a "} -R ^a -, -R ^a -NR ^a -R ^a -, -R ^a -SiR ^a" R ^{a "} -R ^a -, - R ^a -SiR ^a" R ^{a '} -, -SiR ^{a "} R ^a" -R ^a -, -R ^a -OR ^a -, -R ^a -CO-R ^a -, -R ^a -CO-OR ^a -, -R ^a -O-CO-OR ^a -, R ^a -O-CO-R ^a -, -OR ^a -, -R ^a -CS-R ^a -, -R ^a -CO-SR ^a -, -R ^a -S-CO-R ^a - , -R ^a -CO-NH-R ^a -, -R ^a - NH-CO-R ^a -, -R ^a -O-, -R ^a -SR ^a -, -SR ^a -, -R ^a -S -, R ^a -SO-R ^a -, -SO-R ^{3 '} -, -R ^a -SO-, -R ^a -SO ₂ - R ^a -, -SO ₂ -R ^a - and -R ^a - SO ₂ -, wherein R ^a and R ^a are each independently a radical having up to 20 carbon atoms, selected from the group consisting of a linear, branched or cyclic alkylene radical, a linear, branched or cyclic heteroalkylene radical, an arylene radical, a heteroarylene radical , a linear, branched or cyclic alkenyle nrest and a linear, branched or cyclic alkynylene radical,

each optionally with one or more of the substituents selected from the group consisting of halogens, deuterium, linear, branched or cyclic alkyl, linear, branched or cyclic heteroalkyl, aryl, heteroaryl, linear, branched or cyclic alkenyl, linear, branched or cyclic alkynyl and other donor and acceptor groups such as, for example, amines, phosphines, carboxylates and their esters, and CF ₃ - groups, where the substituents may optionally form a cyclized and / or fused structure with each other, wherein R ^a and R ^a independently each are each a radical having up to 20 carbon atoms, independently selected from the group consisting of hydrogen, deuterium, halogen, -R ^c , -OC (O) R ^c , -COOH, -OR ^c , - NR ^C R ^C , -SiR ^c R ^c R ^c -SR ^C , -SOR ^c , -SO ₂ R ^c and other donor and acceptor groups such as carboxylates and their esters and CF ₃ groups,

wherein R ^c , R ^c and R ^{c are} independently selected from the group consisting of H, OH, NH ₂ , NHR ^X , NR ^x R ^y , a halogen, a substituted or unsubstituted, linear, branched or cyclic Ci-20 alkyl, Ci-20-heteroalkyl, C2-2o-alkenyl, Ci-io-Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl , C6-3i-heteroarylalkyl, Cs-33- Alkylarylalkylrest and a C _7- 32-Heteroalkylarylalkylrest,

wherein R ^x and R ^{y are} independently selected from the group consisting of a substituted or unsubstituted, linear, branched or cyclic Ci-20-alkyl, Ci-20-heteroalkyl, C2-2o alkenyl, Ci-io -Heteroalkenylrest and a substituted or unsubstituted C6-2o-aryl, C _5- 2o-heteroaryl, C ₇ 32 arylalkyl, C 6-31 - heteroarylalkyl, Cs-33-Alkylarylalkylrest and a C _7- 32 -Heteroalkylarylalkylrest, where the radicals R ^c , R ^{c '} , R ^{c "} , R ^a , R ^a' , R ^a" and R ^{a "} can optionally also lead to fused ring systems, and

wherein at least one of Z (or Z ^x) is substituted with at least one non-complexed ionic group, preferably having an ammonium group, a carboxyl group, a sulfonate group, a phosphonate group, in particular - is substituted SO3 ^".

Preferably, the heteroaromatic group comprising N, Y, Y ^' and Z ^{x is} selected from the group consisting of pyridyl, pyrimidyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, each of which may optionally be substituted and / or fused to another group of the complex , Preferably, the ligands L and L 'according to formula H are monodentate ligands having up to 42 carbon atoms.

The embodiment and the claims serve to illustrate and explain the invention.

example

Under a protective gas atmosphere, 100 mg of triphenylphosphine-3-sodium sulfonate are dissolved in 5 ml of ethanol and mixed with 47 mg of Cul. Subsequently, the addition of the Diphenyl-2-picolylphopshin (34mg). It is stirred overnight at RT and the yellow solution is treated with diethyl ether. The yellow solid is filtered off and washed with diethyl ether. After drying in vacuo, a yellow solid is obtained.

The emission maximum (E _max ) is 545 nm. The quantum yield at 68%. Thus, a good light output in the desired visible spectrum can be achieved. In addition, an emitter layer B produced from this compound is particularly conductive.

Claims

claims Opto-electronic device comprising an organochemical emitter compound E having a ΔΕ distance between the lowest triplet state and the overlying singlet state of not more than 3000 cm ^-1 , wherein the organochemical emitter compound E contains at least one non-complexed ionic group , Opto-electronic device according to claim 1, in which the organochemical emitter compound E has a ΔΕ distance of not more than 2000 cm ^-1 , preferably not more than 1000 cm ^-1 . Optoelectronic device according to claim 1 or 2, wherein the optoelectronic device is a light emitting electrochemical cell, an organic light emitting diode, an organic laser, an organic solar cell or an optical sensor, in particular a light emitting electrochemical cell. Opto-electronic device according to one of claims 1 to 3, in which the ionic group is selected from -SO 3 ^" , -PO 3 ^" , -COO ^" and -NH ₃ ⁺ , preferably SO ₃ ^" , -PO 3 ^" or -COO ^" , especially SO ₃ ^" . Opto-electronic device according to one of claims 1 to 4, in which the ionic group is bonded to an aryl radical of the organochemical emitter compound E. An opto-electronic device according to any one of claims 1 to 5, wherein the organochemical emitter compound E is a metal (I) complex of a metal M selected from the group consisting of Cu, Ag and Au, wherein the metal (I) is further preferred is complexed with at least one halogen. Opto-electronic device according to claim 6, in which the complexed metal (I) is a Cu (I) and the halogen iodine, preferably wherein the metal (I) complex is a tetracoordinated organic Cu (I) complex, preferably where the metal (I) complex contains two quadruple complexed Cu (I), with the Cu (I) also forming two complex bonds with iodine. Opto-electronic device according to claim 6 or 7, in which the metal (I) complex has a structure according to one of the following formulas (I) or (II):

wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently any organochemical radical, preferably a substituted or unsubstituted aryl radical, a substituted or unsubstituted alkylaryl radical, a substituted or unsubstituted arylalkyl radical or a substituted or unsubstituted C 1-20 -alkyl radical, where at least one of the radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 contains} the ionic group; where M is a metal (I), preferably Cu (I), Ag (I) or Au (I), in particular Cu (I); wherein Y is any bivalent group, preferably a bivalent group containing at least one π-electron system conjugated with the structure of formulas (I) or (II), preferably a divalent group taken together with the carbon atom and the nitrogen atom of the structure the formula (I) or (II) forms a mononuclear or polynuclear, substituted or unsubstituted aromatic ring system; and wherein in the structure of formula (II) Z is any bivalent group, preferably a bivalent group selected from the group consisting of -R ^a -, -OR ^a -O-, -R ^a -N = N-, -N = NR ^a -, -R ^a -N = NR ^b -, -OR ^a -, -R ^a -O-, -R ^a -OR ^b -, -NR ^d - R ^a -, -R ^a -NR ^d -, -R ^a -NR ^d -R ^a -, -NR ^d -R ^a -NR ^e -, -R ^a -NR ^d -NR ^e -, -R ^a -N = N-, -NR ^d -NR ^e - R ^a -, -N = NR ^a -, -R ^a -N = NR ^b -, -N = CR ^d -NR ^e -, -R ^a -N = CR ^d -NR ^e -, -R ^a -N = CR ^d -NR ^e -R ^b - , -N = CR ^d -NR ^e -R ^a -, -N = CR ^d -R ^a -NH-, -R ^a -N = CR ^d -R ^b -NR ^e -, -N = CR ^d -R ^a -NR ^e -R ^a -, - R ^a -N = CR ^d -R ^b -NR ^e R ^c -, -NR ^d -CR ^e = N-, -R ^a -NR ^d -CR ^e = N-, -NR ^d -CR ^e = NR ^a -, -R ^a - NR ^d -CR ^e = NR ^b -, -NR ^d -R ^a -CR ^e = N-, -R ^a -NR ^d -R ^b -CR ^e = N-, -NR ^d -R ^a -CR ^e = NR ^b -, -R ^a - NR ^d -R ^b -CR ^e = NR ^a -, -R ^a -N = C = N-, -N = C = NR ^a -, -N = CR ^{d e} -CR = N-, -R ^a -N = CR ^d - ^e CR = N-, -N = CR ^d -CR ^s = NR ^a -, -R ^a -N = CR ^d -CR ^e = NR ^b -, -N = CR ^d -R ^a -CR ^e = NR ^b -, - R ^a -N = CR ^d -R ^b -CR ^e = N-, -R ^a -N = CR ^d -R ^b -CR ^e = NR ^c -, -OR ^a -NR ^d -R ^a -OR ^b -NH -, -O- R ^a -NR ^d -R ^b -, -R ^a -OR ^b -NR ^d -R ^c -, -NR ^d -R ^a -O-, -R ^a -NR ^d -R ^b -O , -NR ^d -R ^a -OR ^b -, -R ^a - NR ^d -R ^b -OR ^c -, -R ^a -CO-NR ^d -, -CO-NR ^d -R ^a -, -R ^a -CO-NR ^d -R ^a -, -R ^a -NR ^d -CO-, -NR ^d - CO-R ^a - or -R ^a -NR ^d -CO-R ^a -, SR ^a -S-, - OR ^a -S-, -SR ^a -O-, -SR ^a -, -R ^a -S-, -R ^a -S- R ^b -, -SR ^a -NR ^d -, -R ^a -SR ^b - NR ^d , -SR ^a -NR ^d -R ^b -, -R ^a -SR ^b -NR ^d -R ^c -, -NR ^d -R ^a -S-, - R ^a -NR ^d -R ^b -S-, -NR ^d -R ^a -SR ^b -, -R ^a -NR ^d -R ^b -SR ^c -, -R ^a -CS-NR ^d -, -CS- NR ^d -R ^a -, -R ^a - CS-NR ^d -R ^b -, -R ^a -NR ^d -CS-, -NR ^d -CS-R ^a -, -R ^a -NR ^d -CS-R ^b -, -SO-R ^a -S-, -SO-R ^a -SO-, -SO ₂ -R ^a -SO ₂ -, -SO ₂ -R ^a -SO-, -SO-R ^a -SO ₂ -, -OR ^a -SO-, -OR ^a -SO ₂ -, -SO-R ^a - O-, -SO ₂ -R ^a -O-, -SO-R ^a -, -SO ₂ -R ^a - , -R ^a -SO-, -R ^a -SO ₂ -, -R ^a -SO-R ^b -, -R ^a -SO ₂ -R ^b -, -SO-R ^a -NR ^d -, -SO ₂ -R ^a -NR ^d -, -R ^a -SO-R ^b -NR ^d -, -SO-R ^a -NR ^d -R ^b -, -R ^a -SO-R ^b -NR ^d - R ^c -, -NR ^d -R ^a -SO-, -R ^a -NR ^d -R ^b -SO-, -NR ^d -R ^a -SO-R ^b -, -R ^a -NR ^d -R ^b - SO-R ^c -, -R ^a --SO ₂ -R ^b -NR ^d -, -SO ₂ -R ^a -NR ^d -R ^b -, -R ^a -SO ₂ -R ^b -NR ^d -R ^c - , -NR ^d -R ^a -SO ₂ -, -R ^a -NR ^d -R ^b -SO ₂ -, -NR ^d -R ^a -SO ₂ -R ^b - and -R ^a -NR ^d -R ^b - SO ₂ -R ^c -is, wherein R ^a , R ^b and R ^{c are} each independently selected from Group consisting of substituted or unsubstituted Ci _-2 o-alkylene, substituted or unsubstituted C _2-2 o-alkenylene, substituted or unsubstituted C6-arylene, o _-2, substituted or unsubstituted C ₇ 3 ₂ - arylalkylene, substituted or unsubstituted C8 33 alkylarylene and substituted or unsubstituted C8-33-alkylarylalkylene, and wherein R ^d and R ^e are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted Ci _-2 o alkyl group, a substituted or unsubstituted C _2-2 o- Alkenyl group, a substituted or unsubstituted C6-2o aryl group, a substituted or unsubstituted C _7- 32 arylalkyl group and a substituted or unsubstituted Cs-33-Alkylarylalkylrest, in particular wherein R ^d and R ^e are each hydrogen. An opto-electronic device according to claim 8, wherein in formulas (I) or (II): Z is -R ^a - or -OR ^a -O-; and or  Y together with the carbon atom and the nitrogen atom of the structure of the formulas (I) or (II) is a substituted or unsubstituted aromatic ring system selected from the group consisting of a pyridine ring, oxadiazole ring, pyrrole ring, indole ring, isoindole ring, imidazole ring, triazole ring, benzimidazole ring, purine ring, Pyrazole ring, indazole ring, oxazole ring, benzoxazole ring, isoxazole ring, benzisoxazole ring, thiazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, pyrazine ring, quinoxaline ring, pyrimidine ring and quinazoline ring, especially together with the carbon atom and nitrogen atom of the structure of formulas (I) or (II) or unsubstituted pyridine, 1, 3,4-oxadiazole-imidazole or benzimidazole ring forms. 0. Opto-electronic device according to claim 8 or 9, wherein in the formulas (I) or (II) mean: R ¹ and / or R ^{3 are} independently of each other at least one ionic group substituted aryl radicals, preferably R ¹ and R ^{3 are} each substituted with at least one ionic group aryl radicals; and or R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} unsubstituted aryl radicals. 1 . Opto-electronic device according to one of claims 6 to 10, wherein the metal (I) complex has a structure according to one of the following formulas (III) or (IV):

wherein Z is as defined in claim 8 or 9, in particular wherein Z is an unsubstituted C ₄ -C ₇ alkenyl radical or a p-hydroxyphenol radical; wherein R ¹ and R ^{3 are} each aryl groups substituted with at least one ionic group, preferably wherein the ionic group is selected from -SO 3 ^" , -PO 3 ^" , -COO ^" and -NH ₃ ⁺ , in particular wherein the ionic group is SOs and wherein R ^{9 is} any radical, preferably wherein R is a Ci-20-alkyl or H, in particular wherein R is a C1-10-AI alkyl or H, in particular wherein the metal (I) complex has a structure according to of the following formula (V):

12. Opto-electronic device according to one of claims 1 to 5, in which the organochemical emitter compound E contains no transition metal. Opto-electronic device according to one of claims 1 to 5 or 12, in which the organochemical emitter compound E has a structure according to one of the following formulas (VI) to (XV):

wherein R ^{10 is} an ionic group selected from the group consisting of - SO 3 ^" , -PO 3 ^" , -COO ^" and -NH ₃ ⁺ , in particular wherein the ionic group is an SO ₃ ^" ; wherein X is a direct bond or a divalent organic bridging group selected from the group consisting of a Ci-g-alkylene, C2-8-alkenylene, C _2- 8 alkynylene, or arylene, -CRR ', -C = CRR ', -C = NR, -NR-, -O-, -SiRa-, -S-, -S (O) -, and -S (O) 2- and a combination of two or more thereof; wherein Y represents NR, O or S; wherein Ar is a substituted or unsubstituted aryl or heteroaryl radical of from 5 to 24 aromatic ring atoms, which may be optionally substituted with one or more R, preferably wherein Ar is selected from the group consisting of phenyl, benzyl, ortho, meta or para-biphenyl, ortho, meta, para or branched terphenyl, ortho, meta, para or branched quaterphenyl, 1-naphthyl, 2-naphthyl, pyrrole, furanyl, thiophenyl, indolyl, benzofuranyl, benzothiophenyl, carbazolyl, Dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, anthracenyl, phenanthrenyl, pyrenyl, benzanthracenyl, and combinations of any two or more thereof, which may optionally be substituted with one or more R, in particular wherein Ar is a phenyl or benzyl radical; wherein R and R 'are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -NR ^a R ^b , -CN, - CF ₃ , -NO ₂ , - OH, -COOH, -COOR ^a , -CO (NR ^a ) (NR ^b ), -SiR ^a R ^b R ^c , -B (OR ^a ) (OR ^b ), - CO-R ^a , -POR ^a R ^b , -O-POR ^a R ^b , -SO-R ^a , -SO ₂ R ^a , -OSO ₂ R ^a , a linear alkyl, alkoxy or thioalkoxy of 1 to 40 carbon atoms, a linear alkenyl or alkynyl radical of 2 to 40 carbon atoms, a branched or cyclic alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radical of from 3 to 40 carbon atoms, an aromatic ring system of from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy radical of from 5 to 60 carbon atoms, and a diarylamino , Diheteroarylamino- or Arylheteroarylaminorest of 10 to 40 aromatic ring atoms, each optionally optionally substituted with one or more R ^a , wherein two or more contiguous CH ₂ groups are optionally - R ^a C = CR ^b -, -C ^ C-, -SiR ^a R ^b -, -GeR ^a R ^b -, -SnR ^a R ^b -, -CO-, -CS-, -CSe-, -CNR ^a -, - POR ^a -, -O- (PO) R ^a -O-, -SO-, SO ₂ , -NR ^a -, -O-, -S- or -CONR ^a - exchanged wreden can and wherein one or more hydrogen atoms by deuterium, F, Cl, Br, I, CN, CF ₃ or NO ₂ can be substituted and / or where two or more radicals R may optionally form mono-, bi- or polycyclic aliphatic or aromatic ring systems with one another; wherein R ^a , R ^b and R ^{c are} each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -NR ^d R ^e , -CN, -CF ₃ , - NO 2, -OH, -COOH, -COOR ^e , -CO (NR ^d ) (NR ^e ), -SiR ^d R ^e R ^f , -B (OR ^d ) (OR ^e ), - CO-R ^a , -POR ^d R ^e , -O-POR ^d R ^e , -SO-R ^d , -SO ₂ R ^d , -OSO ₂ R ^d , a linear alkyl, alkoxy or thioalkoxy of 1 to 40 carbon atoms, a linear alkenyl or Alkynyl radical of 2 to 40 carbon atoms, a branched or cyclic alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radical of 3 to 40 carbon atoms, an aromatic ring system of 5 to 60 carbon atoms, an aryloxy or heteroaryloxy radical of 5 to 60 carbon atoms, and a diarylamino, diheteroarylamino or arylheteroarylamino radical of from 10 to 40 aromatic ring atoms, each optionally optionally substituted with one or more R ^d , wherein two or more adjacent CH ₂ groups are optionally - R ^d C = CR ^e -, -C ^ C-, -SiR ^d R ^e -, -GeR ^d R ^e -, -SnR ^d R ^e -, -CO-, -CS-, -CSe-, -CNR ^d -, -POR ^d -, -O- (PO) R ^d -O-, -SO-, SO ₂ , -NR ^d -, -O-, -S- or -CONR ^d - exchanged wreden and wherein one or more hydrogen atoms can be substituted by deuterium, F, Cl, Br, I, CN, CF ₃ or NO ₂ ; wherein R ^d , R ^e and R ^{f are} each independently selected from the group and / or heteroaromatic radical of 1 to 20 carbon atoms, optionally one or more hydrogens may be substituted by F or CF 3. Opto-electronic device according to one of claims 1 to 13, in which the organochemical emitter compound E is present in the emitter layer B in composition Z with an ionic liquid, one or more salts and / or one or more polymer (s). Optoelectronic device according to one of claims 1 to 14, in which the optoelectronic device is a light emitting electrochemical cell comprising the following layers: A) an anode layer A, preferably comprising indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene; B) an emitter layer B containing the organochemical emitter compound E; and C) a cathode layer C, preferably comprising Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more thereof. A method of producing light of a particular wavelength, comprising the step of providing an opto-electronic device according to any one of claims 1 to 15.