Metal complex, semiconductor layer comprising a metal complex and organic electronic device

Abstract

The present invention relates to a compound of formula (I) as well as to an organic electronic device comprising a semiconductor layer which comprises a compound of formula (I).

Description

[0001] Invention Title

[0002] Metal complex, semiconductor layer comprising a metal complex and organic electronic device

[0003] Technical Field

[0004] The present invention relates to a metal complex, a semiconductor layer comprising the metal complex and an organic electronic device comprising at least one metal complex thereof.

[0005] Background Art

[0006] Electronic devices, such as organic light-emitting diodes OLEDs, which are self-emitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode layer, a hole injection layer HIL, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode layer, which are sequentially stacked on a substrate. In this regard, the HIL, the HTL, the EML, and the ETL are thin films formed from organic compounds.

[0007] When a voltage is applied to the anode and the cathode, holes injected from the anode move to the EML, via the HIL and HTL, and electrons injected from the cathode move to the EML, via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced, so that an OLED having the above-described structure has low operating voltage, excellent efficiency and / or a long lifetime.

[0008] Performance of an organic light emitting diode may be affected by characteristics of the hole injection layer, and among them, may be affected by characteristics of the hole transport compound and the metal complexes which are contained in the hole injection layer.

[0009] There remains a need to improve performance of a metal complex, suitable for use as semiconductor materials, semiconductor layers, as well as electronic devices thereof, in particular to achieve current efficiency, external quantum efficiency, and / or a good operational voltage, and good stability such as lifetime and / or good rise of the operational voltage over time through improving the characteristics of the metal complex comprised therein. DISCLOSURE

[0010] An aspect of the present invention provides a metal complex of formula (I)

[0011] ZnL2(AL)m(I)

[0012] whereby Zn is in the oxidation state Zn(II),

[0013] L is a ligand of formula (II)

[0014]

[0015] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0016] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0017] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0018] wherein L comprises at least one aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0019] wherein AL is an ancillary ligand which coordinates to the metal M;

[0020] wherein m is an integer selected from 0 to 2,

[0021] According to one embodiment of the present invention, a a ligand of formula (II) from the following table is excluded:

[0022]

[0023] According to one embodiment of the present invention, a metal complex of formula (I) from the following table is excluded:

[0024]

[0025] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0026] ZnL2(AL)m(I) whereby Zn is in the oxidation state Zn(II),

[0027] L is a ligand of formula (II)

[0028]

[0029] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0030] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0031] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0032] wherein L comprises at least one aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; wherein AL is an ancillary ligand which coordinates to the metal M;

[0033] wherein m is an integer selected from 0 to 2; and

[0034] wherein a ligand of formula (II) from the following table is excluded:

[0035]

[0036]

[0037] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0038] ZnL2(AL)m(I)

[0039] whereby Zn is in the oxidation state Zn(II),

[0040] L is a ligand of formula (II)

[0041]

[0042] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl;

[0043] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl;

[0044] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl, CN, or NO2;

[0045] wherein L comprises at least one aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; wherein AL is an ancillary ligand which coordinates to the metal M;

[0046] wherein m is an integer selected from 0 to 2; and wherein a metal complex of formula (I) from the following table is excluded:

[0047]

[0048] Definitions

[0049] It should be noted that throughout the application and the claims that the metal complex or metal complex of formula (I) is also referred to as compound.

[0050] It should be noted that throughout the application and the claims any R1, R2, R3, L and M. always refer independently from each other to the same moieties according to their definition, unless otherwise noted.

[0051] In the present specification, when a definition is not otherwise provided, "substituted" refers to a substituted selected from substituted or unsubstituted C₁ to C₁₂ alkyl, partially or fully fluorinated C₁ to C₁₂ alkyl, substituted or unsubstituted C₆ to C₁₉ aryl, and substituted or unsubstituted C₂ to C₂₀ heteroaryl, wherein the substituents are selected from the substituents of the substituted or unsubstituted C₁ to C₁₂ alkyl, substituted or unsubstituted C₆ to C₁₉ aryl, and substituted or unsubstituted C₂ to C₂₀ heteroaryl are selected are independently selected from halogen, Cl, F, CN, partially or perfluorinated C₁ to C₈ alkyl, partially or perfluorinated C₁ to C₈ alkoxy.

[0052] In the present specification, "aryl group" and “aromatic rings” refers to a hydrocarbyl group which may be created by formal abstraction of one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon which contains at least one aromatic ring or aromatic ring system. Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons fulfilling Huckel’s rule. Examples of aryl groups include monocyclic groups like phenyl or tolyl, polycyclic groups which comprise more aromatic rings linked by single bonds, like biphenyl, and polycyclic groups comprising fused rings, like naphthyl or fluorenyl.

[0053] Analogously, under “heteroaryl” and “heteroaromatic”, it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a heterocyclic aromatic ring in a metal complex comprising at least one such ring.

[0054] The term “non-heterocycle” is understood to mean a ring or ring-system comprising no hetero-atom as a ring member.

[0055] The term “heterocycle” is understood to mean that the heterocycle comprises at least one ring comprising one or more hetero-atoms. A heterocycle comprising more than one ring means that all rings comprising a hetero-atom or at least one ring comprising a hetero atom and at least one ring comprising C-atoms only and no hetero atom. A C2 heteroaryl group means that an heteroaryl ring comprises two C- Atoms and the other atoms are hetero-atoms.

[0056] Under heterocycloalkyl, it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a saturated cycloalkyl ring in a compound comprising at least one such ring.

[0057] The term “aryl” having at least 9 C-atoms may comprise at least one fused aryl ring. The term “heteroaryl” having at least 9 atoms may comprise at least one fused heteroaryl ring fused with a heteroaryl ring or fused with an aryl ring.

[0058] The term “fused aryl rings” or “condensed aryl rings” is understood the way that two aryl rings are considered fused or condensed when they share at least two common sp2-hybridized carbon atoms.

[0059] The term “fused ring system” is understood to mean a ring system wherein two or more rings share at least two atoms.

[0060] The term ”5-, 6- or 7-member ring” is understood to mean a ring comprising 5, 6 or 7 atoms. The atoms may be selected from C and one or more hetero-atoms.

[0061] In the present specification, the single bond refers to a direct bond.

[0062] In the present specification, when a definition is not otherwise provided, "substituted" refers to one substituted with a H, deuterium, halogen, Cl, F, CN, partially or perfluorinated C₁ to C₈ alkyl, partially or perfluorinated C₁ to C₈ alkoxy. In the present specification “substituted aryl” refers for example to a C₆ to C₁₉ aryl or to C₁₈ aryl that is substituted with one or more substituents, wherein the substituent may be substituted with none, one or more substituents, preferably the substituent may be selected from H, deuterium, halogen, Cl, F, CN, partially or perfluorinated C₁ to C₈ alkyl, partially or perfluorinated C₁ to C₈ alkoxy.

[0063] Correspondingly, in the present specification “substituted heteroaryl” refers to a substitution with one or more substituents, which themselves may be substituted with one or more substituents, preferably the substituent may be selected from H, deuterium, halogen, Cl, F, CN, partially or perfluorinated C₁ to C₈ alkyl, partially or perfluorinated C₁ to C₈ alkoxy..

[0064] In the present specification, when a definition is not otherwise provided, a substituted heteroaryl group with at least 2 C-ring atoms may be substituted with one or more substituents. For example, a substituted C2 heteroaryl group may have 1 or 2 substituents.

[0065] A substituted aryl group with at least 6 ring atoms may be substituted with 1, 2, 3, 4 or 5 substituents.

[0066] A substituted heteroaryl group may comprise at least 5 or 6 ring atoms. A substituted heteroaryl group that may comprise at least 5 or 6 ring atoms may be substituted with 1, 2, 3 or 4 substituents, if the heteroaryl group comprises one hetero atom and five C-atoms, or it may be substituted with 1, 2 or 3 substituents, if the heteroaryl group with at least 6 ring atoms comprises two hetero atom and four C-atoms, or may be substituted with 1 or 2 substituents, if the heteroaryl group with at least 6 ring atoms comprises three hetero atoms and three C-atoms, wherein the substituent is bonded to the C-ring atoms only.

[0067] In the present specification, when a definition is not otherwise provided, an "alkyl group" refers to a saturated aliphatic hydrocarbyl group. The alkyl group may be a Ci to C12 alkyl group. More specifically, the alkyl group may be a Ci to C10 alkyl group or a Ci to Ce alkyl group. For example, a Ci to C4 alkyl group includes 1 to 4 carbons in alkyl chain, and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl.

[0068] Specific examples of the alkyl group may be a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a branched pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantly group and the like.

[0069] In the present specification, when a definition is not otherwise provided, a "substituted alkyl group" may refer to a linear, branched or cyclic substituted saturated aliphatic hydrocarbyl group. The substituted alkyl group may be a linear, branched or cyclic Ci to C12 alkyl group. More specifically, the substituted alkyl group may be a linear, branched or cyclic substituted Ci to C10 alkyl group or a linear, branched or cyclic substituted Ci to Ce alkyl group. For example, a linear, branched or cyclic substituted Ci to C4 alkyl group includes 1 to 4 carbons in the alkyl chain, and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl and cyclohexyl. The substituents may be selected from halogen, F, Cl, CN, OCH3, OCF3.

[0070] The term “hetero” is understood the way that at least one carbon atom, in a structure which may be formed by covalently bound carbon atoms, is replaced by another polyvalent atom. Preferably, the heteroatoms are selected from B, Si, N, P, O, S; further preferred from N, P, O, S and most preferred N.

[0071] In the present specification, when a substituent is not named, the substituent may be a H. The term “charge-neutral” means that the group AL is overall electrically neutral.

[0072] In the context of the present invention, “different” means that the metal complexes do not have an identical chemical structure.

[0073] The term “free of’, “does not contain”, “does not comprise” does not exclude impurities which may be present in the metal complex prior to deposition. Impurities have no technical effect with respect to the object achieved by the present invention.

[0074] The term “contacting sandwiched” refers to an arrangement of three layers whereby the layer in the middle is in direct contact with the two adjacent layers.

[0075] The terms “light-absorbing layer” and “light absorption layer” are used synonymously. The terms “light-emitting layer”, “light emission layer” and “emission layer” are used synonymously.

[0076] The terms “OLED”, “organic light-emitting diode” and “organic light-emitting device” are used synonymously.

[0077] The terms anode, anode layer and anode electrode are used synonymously.

[0078] The term "at least two anode sub-layers" is understood to mean two or more anode sublayers, for example two or three anode sub-layers.

[0079] The terms cathode, cathode layer and cathode electrode are used synonymously.

[0080] The term “hole injection layer” is understood to mean a layer which improves charge injection from the anode layer into further layers in the electronic device or from further layers of the electronic device into the anode. The term “hole transport layer” is understood to mean a layer which transports holes between the hole injection layer and further layers arranged between the hole injection layer and the cathode layer.

[0081] The operating voltage U is measured in Volt.

[0082] In the context of the present specification the term “essentially non-emissive” or “non-emissive” means that the contribution of the metal complex of formula (I) or the hole injection layer comprising a metal complex of formula (I), to the visible emission spectrum from an electronic device, such as OLED or display device, is less than 10 %, preferably less than 5 % relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of about > 380 nm to about < 780 nm.

[0083] In the context of the present invention, the term “sublimation" may refer to a transfer from solid state to gas phase or from liquid state to gas phase.

[0084] In the specification, hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.

[0085] In addition, electron characteristics refer to an ability to accept an electron when an electric field is applied and that electrons formed in the cathode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.

[0086] The term “HOMO level” is understood to mean the highest occupied molecular orbital and is determined in eV (electron volt).

[0087] The term “HOMO level further away from vacuum level” is understood to mean that the absolute value of the HOMO level is higher than the absolute value of the HOMO level of the reference compound. For example, the term “further away from vacuum level than the HOMO level of N2, N2, N2', N2', N7, N7, N7', N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine is understood to mean that the absolute value of the HOMO level of the matrix compound of the hole injection layer is higher than the HOMO level of N2, N2, N2', N2', N7, N7, N7', N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine.

[0088] The term “absolute value” is understood to mean the value without the “- “symbol.

[0089] According to one embodiment of the present invention, the HOMO level of the matrix compound of the hole injection layer may be calculated by quantum mechanical methods. Advantageous Effects

[0090] Surprisingly, it was found that the electronic device according to the invention solves the problem underlying the present invention by enabling electronic devices, such as organic lightemitting diodes, in various aspects superior over the electronic devices known in the art, in particular with respect to current efficiency, external quantum efficiency, and / or a good operational voltage, and good stability such as lifetime and / or good rise of the operational voltage over time.

[0091] According to one embodiment, the Zn in the compound of formula (I) has the oxidation state +11 (= Zn(II)).

[0092] According to one embodiment in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl.

[0093] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0094] ZnL2(AL)m(I)

[0095] whereby Zn is in the oxidation state Zn(II),

[0096] L is a ligand of formula (II)

[0097]

[0098] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl; wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0099] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0100] wherein in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0101] wherein AL is an ancillary ligand which coordinates to the metal M;

[0102] wherein m is an integer selected from 0 to 2; and

[0103] wherein a ligand of formula (II) from the following table is excluded:

[0104]

[0105] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0106] ZnL2(AL)m(I)

[0107] whereby Zn is in the oxidation state Zn(II),

[0108] L is a ligand of formula (II)

[0109]

[0110] (II)

[0111] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0112] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0113] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0114] wherein in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0115] wherein AL is an ancillary ligand which coordinates to the metal M;

[0116] wherein m is an integer selected from 0 to 2; and

[0117] wherein a metal complex of formula (I) from the following table is excluded:

[0118]

[0119]

[0120] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0121] ZnL2(AL)m(I)

[0122] whereby Zn is in the oxidation state Zn(II),

[0123] L is a ligand of formula (II)

[0124]

[0125] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl;

[0126] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl;

[0127] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C20 heteroaryl, CN, or NO2;

[0128] wherein in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; wherein AL is an ancillary ligand which coordinates to the metal M;

[0129] wherein m is an integer selected from 0 to 2; and

[0130] wherein a ligand of formula (II)from the following table is excluded:

[0131]

[0132] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0133] ZnL2(AL)m(I)

[0134] whereby Zn is in the oxidation state Zn(II),

[0135] L is a ligand of formula (II)

[0136]

[0137] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl; wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0138] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0139] wherein in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0140] wherein AL is an ancillary ligand which coordinates to the metal M;

[0141] wherein m is an integer selected from 0 to 2; and

[0142] wherein a metal complex of formula (I) from the following table is excluded:

[0143]

[0144] According to one embodiment in Ligand L at least one of R1and R2is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl.

[0145] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0146] ZnL2(AL)m(I) whereby Zn is in the oxidation state Zn(II),

[0147] L is a ligand of formula (II)

[0148]

[0149] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0150] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0151] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0152] wherein in Ligand L at least one of R1and R2is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0153] wherein AL is an ancillary ligand which coordinates to the metal M;

[0154] wherein m is an integer selected from 0 to 2; and

[0155] wherein a ligand of formula (II) from the following table is excluded:

[0156]

[0157]

[0158] Furthermore, an embodiment is directed to a metal complex of formula (I)

[0159] ZnL2(AL)m(I)

[0160] whereby Zn is in the oxidation state Zn(II),

[0161] L is a ligand of formula (II)

[0162]

[0163] wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0164] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0165] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0166] wherein in Ligand L at least one of R1and R2is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;

[0167] wherein AL is an ancillary ligand which coordinates to the metal M; wherein m is an integer selected from 0 to 2; and

[0168] wherein a metal complex of formula (I) from the following table is excluded:

[0169] Name: m Ligand L

[0170] Ex-1 0

[0171] k / F° O

[0172] > M..

[0173] Xs N. J JTVF

[0174] F F

[0175] Ex-2 0 F

[0176] 9 o

[0177] F X / "N' N=Z\ ( / T / V / F

[0178] CF2H | F

[0179] F

[0180]

[0181] According to one embodiment, the molecular mass of L is selected in the range of < 600 Da and > 176 Da, preferably < 550 Da and > 280 Da and most preferred < 550 Da and > 240 Da.

[0182] According to an embodiment, the one or more substituents on R1are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0183] the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and

[0184] the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0185] According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0186] wherein the one or more substituents on R1are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0187] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;herein R3is selected from substituted or unsubstituted Cito C12alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Cito C12alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6to C19aryl, substituted or unsubstituted C2to C20heteroaryl, CN, or NO2;

[0188] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN or NO2,

[0189] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0190] According to an embodiment, the substituted or unsubstituted Ce to C19 aryl, and the substituted or unsubstituted C2 to C20 heteroaryl is selected from formula (III), and (IV)

[0191]

[0192] wherein

[0193] X1is selected from N or CR4;

[0194] X2is selected from N or CR5;

[0195] X3is selected from N or CR6;

[0196] X4is selected from N or CR7;

[0197] X5is selected from N or CR8;

[0198] wherein

[0199] X1'is selected from N or CR9; X2'is selected from N or CR10;

[0200] X3'is selected from N or CR11;

[0201] X4'is selected from N or CR12;

[0202] X5'is selected from N or CR13;

[0203] wherein R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

[0204] According to an embodiment, wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

[0205] According to an embodiment, wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (III), or formula (IV);

[0206] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl,, formula (III), or formula (IV);

[0207] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl,, formula (III), or formula (IV), CN, or NO2; and

[0208] wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

[0209] According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (III), or formula (IV), wherein the one or more substituents on R1are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0210] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (III), or formula (IV), CN, or NO2;

[0211] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;herein R3is selected from substituted or unsubstituted Cito C12alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Cito C12alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6to C19aryl, substituted or unsubstituted C2to C20heteroaryl, CN, or NO2;

[0212] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (III), or formula (IV);

[0213] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and

[0214] wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

[0215] According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV),

[0216] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV);

[0217] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III), or formula (IV). According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV),

[0218] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV);

[0219] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III), or formula (IV); and

[0220] wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

[0221] According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV), with the proviso that R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2,

[0222] wherein the one or more substituents on R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0223] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV),

[0224] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0225] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III), or formula (IV). wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0226] According to an embodiment, R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV), with the proviso that R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2,

[0227] wherein the one or more substituents on R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0228] wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III), or formula (IV),

[0229] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0230] wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III), or formula (IV).

[0231] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and

[0232] wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

[0233] According to an embodiment, R3is selected from CH3, CF3, and CF2H, more preferably from CH3, and CF3, and most preferably from CH3. According to an embodiment, R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2 R1is selected from formula (III) and R2is selected from formula (IV), CH3, CF3, and CF2H

[0234] According to an embodiment, R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2 R1is selected from formula (III) and R2is selected from formula (IV) and CF3.

[0235] According to an embodiment, R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, R1is selected from formula (III) and R2is selected from formula (IV).

[0236] According to an embodiment, R3is selected from CH3, CF3, and CF2H, R1is selected from formula (III) and R2is selected from formula (IV), CH3, CF3, and CF2H.

[0237] According to an embodiment, R3is selected from CH3, CF3, and CF2H, R1is selected from formula (III) and R2is selected from formula (IV) and CF3.

[0238] According to an embodiment, R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0239] According to an embodiment, R2is selected from CH3, CF3, and CF2H; and R3is selected from CH3, CF3, and CF2H. According to an embodiment, wherein R1is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl; R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0240] This above embodiment is in itself of inventive value and may be the basis for a separate invention.

[0241] According to an embodiment, wherein R1is selected from formula (III); R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0242] This above embodiment is in itself of inventive value and may be the basis for a separate invention.

[0243] According to an embodiment, wherein R1is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl; R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0244] This above embodiment is in itself of inventive value and may be the basis for a separate invention.

[0245] According to an embodiment, R1is selected from formula (III), R2is selected from CH3, CF3, and CF2H; and R3is selected from CH3, CF3, and CF2H, CN. This above embodiment is in itself of inventive value and may be the basis for a separate invention.

[0246] According to an embodiment, R3is selected from CH3, CF3, and CF2H.

[0247] According to an embodiment, R3is selected from CH3, CF3, and CF2H, R1is selected from formula (III) and R2is selected from formula (IV).

[0248] According to an embodiment, the one or more substituents on R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0249] According to an embodiment, wherein the substituted or unsubstituted Ce to C19 aryl, and the substituted or unsubstituted C2 to C20 heteroaryl is selected from formula (Illa), and (IVa)

[0250]

[0251] wherein

[0252] X1is selected from N or CR4;

[0253] X2is selected from N or CR5;

[0254] X3is selected from N or CR6;

[0255] X4is selected from N or CR7;

[0256] X5is selected from N or CR8;

[0257] wherein

[0258] X1'is selected from N or CR9;

[0259] X2'is selected from N or CR10;

[0260] X3'is selected from N or CR11;

[0261] X4'is selected from N or CR12;

[0262] X5'is selected from N or CR13; wherein R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2, wherein the one or more substituents on R4, R5, R6,R7, R8, R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0263] According to an embodiment, in ligand L R1is selected from formula (IIIb), X2—X1

[0264] X3\\

[0265] c / *

[0266]

[0267] (IIIb),

[0268] wherein

[0269] X1is selected from N or CR4;

[0270] X2is selected from N or CR5;

[0271] X3is selected from N or CR6;

[0272] X4is selected from N or CR7;

[0273] X5is selected from N or CR8;

[0274] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0275] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0276] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2. Preferably one of R2and R3is independently selected from CH3, CF3, and CF2H, more preferred from CH3, and CF3, and most preferred from CH3.

[0277] According to an embodiment, in ligand L R1is selected from formula (Illb’),

[0278] / X2-X1

[0279] X3\\

[0280] \, / *

[0281]

[0282] X'x5(nib’),

[0283] wherein

[0284] X1is selected from N or CR4;

[0285] X2is selected from N or CR5;

[0286] X3is selected from N or CR6;

[0287] X4is selected from N or CR7;

[0288] X5is selected from N or CR8;

[0289] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0290] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0291] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl;

[0292] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2.

[0293] Preferably one of R2and R3is independently selected from CH3, CF3, and CF2H, more preferred from CH3, and CF3, and most preferred from CH3.

[0294] According to an embodiment, in Ligand L R1is selected from formula (IIIe),

[0295]

[0296] wherein

[0297] X1is selected from N or CR4;

[0298] X2is selected from N or CR5;

[0299] X3is selected from N or CR6;

[0300] X4is selected from N or CR7;

[0301] X5is selected from N or CR8;

[0302] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2,

[0303] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0304] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0305] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2,

[0306] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2. Preferably one of R2and R3is independently selected from CH3, CF3, and CF2H, and more preferred from CH3, and CF3.

[0307] According to an embodiment, in Ligand L R1is selected from formula (life’),

[0308] *2-x1

[0309] x3\\

[0310] \ A

[0311] X ~~~Y5

[0312]

[0313] A(inc’),

[0314] wherein

[0315] X1is selected from N or CR4;

[0316] X2is selected from N or CR5;

[0317] X3is selected from N or CR6;

[0318] X4is selected from N or CR7;

[0319] X5is selected from N or CR8;

[0320] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0321] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0322] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0323] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0324] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0325] Preferably one of R2and R3is independently selected from CH3, CF3, and CF2H, and more preferred from CH3, and CF3.

[0326] According to an embodiment, in Ligand L R1is selected from formula (IIId),

[0327] ,x2-x1

[0328] X3\\

[0329] \, / *

[0330]

[0331] X'X5(IIId),

[0332] wherein

[0333] X1is selected from N or CR4;

[0334] X2is selected from N or CR5;

[0335] X3is selected from N or CR6;

[0336] X4is selected from N or CR7;

[0337] X5is selected from N or CR8;

[0338] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0339] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVb);

[0340] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, formula (IVb);

[0341] with the proviso that one of R2and R3is selected from formula (IVb), / 4~-x5'

[0342]

[0343] X2-X1'(ivb),

[0344] wherein

[0345] X1'is selected from N or CR9;

[0346] X2'is selected from N or CR10;

[0347] X3'is selected from N or CR11;

[0348] X4'is selected from N or CR12;

[0349] X5'is selected from N or CR13;

[0350] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0351] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferred from CH3, and CF3, and most preferred from CH3.

[0352] According to an embodiment, in Ligand L R1is selected from formula (Hid’),

[0353]

[0354] wherein

[0355] X1is selected from N or CR4;

[0356] X2is selected from N or CR5;

[0357] X3is selected from N or CR6;

[0358] X4is selected from N or CR7;

[0359] X5is selected from N or CR8;

[0360] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0361] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0362] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVb’);

[0363] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, formula (IVb’);

[0364] with the proviso that one of R2and R3is selected from formula (IVb’),

[0365] / X 'X5'

[0366] V >■

[0367]

[0368] x=x’'

[0369] wherein

[0370] X1'is selected from N or CR9;

[0371] X2'is selected from N or CR10;

[0372] X3'is selected from N or CR11;

[0373] X4'is selected from N or CR12;

[0374] X5'is selected from N or CR13;

[0375] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

[0376] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferred from CH3, and CF3, and most preferred from CH3.

[0377] According to an embodiment, in Ligand L R1is selected from formula (Hid”), X2—X1

[0378] X3\\

[0379] V / *

[0380]

[0381] X'X5(IIId''),

[0382] wherein

[0383] X1is selected from N or CR4;

[0384] X2is selected from N or CR5;

[0385] X3is selected from N or CR6;

[0386] X4is selected from N or CR7;

[0387] X5is selected from N or CR8;

[0388] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0389] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0390] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVb”);

[0391] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, formula (IVb”);

[0392] with the proviso that one of R2and R3is selected from formula (IVb”),

[0393]

[0394] 1x=x’ y'

[0395] wherein

[0396] X1'is selected from N or CR9;

[0397] X2'is selected from N or CR10; X3'is selected from N or CR11;

[0398] X4'is selected from N or CR12;

[0399] X5'is selected from N or CR13;

[0400] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF.

[0401] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferred from CH3, and CF3, and most preferred from CH3.

[0402] According to an embodiment, in Ligand L R1is selected from formula (IIIe), ZZX2'X1

[0403] X3\\

[0404] \d / *

[0405]

[0406] X'X5(IIIe),

[0407] wherein

[0408] X1is selected from N or CR4;

[0409] X2is selected from N or CR5;

[0410] X3is selected from N or CR6;

[0411] X4is selected from N or CR7;

[0412] X5is selected from N or CR8;

[0413] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2,

[0414] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc),,

[0415] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0416] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc), CN, or NO2,

[0417] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2

[0418] with the proviso that one of R2and R3is selected from formula (IVc),

[0419]

[0420] 1 ' / y

[0421] wherein

[0422] X1'is selected from N or CR9;

[0423] X2'is selected from N or CR10;

[0424] X3'is selected from N or CR11;

[0425] X4'is selected from N or CR12;

[0426] X5'is selected from N or CR13;

[0427] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2, wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0428] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferably from CH3, and CF3, and most preferred from CH3.

[0429] According to an embodiment, in Ligand L R1is selected from formula (file’),

[0430] X2—X1

[0431] X3\\

[0432] X4-X5(life’),

[0433] wherein

[0434] X1is selected from N or CR4;

[0435] X2is selected from N or CR5;

[0436] X3is selected from N or CR6;

[0437] X4is selected from N or CR7;

[0438] X5is selected from N or CR8;

[0439] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0440] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0441] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0442] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc’), CN, or NO2,

[0443] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc’), CN, or NO2,

[0444] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2

[0445] with the proviso that one of R2and R3is selected from formula (IVc’),

[0446] / z^x5'

[0447] L >

[0448]

[0449] x=x’

[0450] wherein

[0451] X1'is selected from N or CR9;

[0452] X2'is selected from N or CR10;

[0453] X3'is selected from N or CR11;

[0454] X4'is selected from N or CR12;

[0455] X5'is selected from N or CR13;

[0456] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2, wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0457] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferably from CH3, and CF3, and most preferred from CH3.

[0458] According to an embodiment, in Ligand L R1is selected from formula (Ille”), x2-x1

[0459] x3\\

[0460] \ X4~~~Y5 / *

[0461]

[0462] A(Ille”),

[0463] wherein

[0464] X1is selected from N or CR4;

[0465] X2is selected from N or CR5;

[0466] X3is selected from N or CR6;

[0467] X4is selected from N or CR7;

[0468] X5is selected from N or CR8;

[0469] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0470] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0471] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0472] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc”), CN, or NO2,

[0473] wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0474] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, formula (IVc”), CN, or NO2,

[0475] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2 with the proviso that one of R2and R3is selected from formula (IVc”),

[0476]

[0477] wherein

[0478] X1'is selected from N or CR9;

[0479] X2'is selected from N or CR10;

[0480] X3'is selected from N or CR11;

[0481] X4'is selected from N or CR12;

[0482] X5'is selected from N or CR13;

[0483] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3,, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0484] wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF.

[0485] Preferably one of R2and R3is selected from CH3, CF3, and CF2H, more preferably from CH3, and CF3, and most preferred from CH3.

[0486] According to an embodiment, in ligand L R1is selected from formula (IIIf),

[0487]

[0488] wherein X1is selected from N or CR4;

[0489] X2is selected from N or CR5;

[0490] X3is selected from N or CR6;

[0491] X4is selected from N or CR7;

[0492] X5is selected from N or CR8;

[0493] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0494] R2is selected from formula (IVd),

[0495]

[0496] wherein

[0497] X1'is selected from N or CR9;

[0498] X2'is selected from N or CR10;

[0499] X3'is selected from N or CR11;

[0500] X4'is selected from N or CR12;

[0501] X5'is selected from N or CR13;

[0502] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2.

[0503] According to an embodiment, in ligand L R1is selected from formula (Illf ’),

[0504]

[0505] wherein

[0506] X1is selected from N or CR4;

[0507] X2is selected from N or CR5;

[0508] X3is selected from N or CR6;

[0509] X4is selected from N or CR7;

[0510] X5is selected from N or CR8;

[0511] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0512] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0513] R2is selected from formula (IVd’),

[0514]

[0515] wherein

[0516] X1'is selected from N or CR9;

[0517] X2'is selected from N or CR10;

[0518] X3'is selected from N or CR11;

[0519] X4'is selected from N or CR12;

[0520] X5'is selected from N or CR13;

[0521] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2.

[0522] According to an embodiment, in ligand L R1is selected from formula (Ulf”), X2—X1

[0523] X3\\

[0524] / *

[0525]

[0526] X4=X5(IIIf''),

[0527] wherein

[0528] X1is selected from N or CR4;

[0529] X2is selected from N or CR5;

[0530] X3is selected from N or CR6;

[0531] X4is selected from N or CR7;

[0532] X5is selected from N or CR8;

[0533] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0534] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0535] R2is selected from formula (IVd”),

[0536]

[0537] 1x=x’ y'

[0538] wherein

[0539] X1'is selected from N or CR9;

[0540] X2'is selected from N or CR10;

[0541] X3'is selected from N or CR11;

[0542] X4'is selected from N or CR12;

[0543] X5'is selected from N or CR13; wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0544] and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2.

[0545] According to an embodiment, in ligand L R1is selected from formula (IIIg),

[0546] X2—X1

[0547] X3\\

[0548]

[0549] X4=X5(IIIg),

[0550] wherein

[0551] X1is selected from N or CR4;

[0552] X2is selected from N or CR5;

[0553] X3is selected from N or CR6;

[0554] X4is selected from N or CR7;

[0555] X5is selected from N or CR8;

[0556] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0557] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R2is selected from formula (IVe),

[0558]

[0559] wherein

[0560] X1'is selected from N or CR9;

[0561] X2'is selected from N or CR10;

[0562] X3'is selected from N or CR11;

[0563] X4'is selected from N or CR12;

[0564] X5'is selected from N or CR13;

[0565] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0566] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2,

[0567] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0568] According to an embodiment, in ligand L R1is selected from formula (Illg’),

[0569] X2—X1

[0570] X3\\

[0571]

[0572] X4=X5(IIIg'), wherein

[0573] X1is selected from N or CR4;

[0574] X2is selected from N or CR5;

[0575] X3is selected from N or CR6;

[0576] X4is selected from N or CR7;

[0577] X5is selected from N or CR8;

[0578] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0579] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0580] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0581] R2is selected from formula (IVe’),

[0582] X4'—X5'

[0583] y

[0584]

[0585] X2'=X1'

[0586] wherein

[0587] X1'is selected from N or CR9;

[0588] X2'is selected from N or CR10;

[0589] X3'is selected from N or CR11;

[0590] X4'is selected from N or CR12;

[0591] X5'is selected from N or CR13;

[0592] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0593] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2,

[0594] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0595] According to an embodiment, in ligand L R1is selected from formula (Illg”), X2—X1

[0596] X3\\

[0597]

[0598] X4=X5(IIIg''),

[0599] wherein

[0600] X1is selected from N or CR4;

[0601] X2is selected from N or CR5;

[0602] X3is selected from N or CR6;

[0603] X4is selected from N or CR7;

[0604] X5is selected from N or CR8;

[0605] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0606] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0607] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0608] R2is selected from formula (IVe”),

[0609]

[0610] Kx=x’ > „„

[0611] wherein

[0612] X1'is selected from N or CR9;

[0613] X2'is selected from N or CR10;

[0614] X3'is selected from N or CR11;

[0615] X4'is selected from N or CR12;

[0616] X5'is selected from N or CR13;

[0617] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0618] wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0619] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2;

[0620] wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0621] According to an embodiment, in Ligand L R1is selected from formula (IIIh), X2—X1

[0622] X3\\

[0623] \ „ / *

[0624]

[0625] X4=X5(IIIh),

[0626] wherein

[0627] X1is selected from N or CR4;

[0628] X2is selected from N or CR5;

[0629] X3is selected from N or CR6;

[0630] X4is selected from N or CR7;

[0631] X5is selected from N or CR8;

[0632] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0633] R2is selected from formula (IVf),

[0634]

[0635] wherein

[0636] X1'is selected from N or CR9;

[0637] X2'is selected from N or CR10;

[0638] X3'is selected from N or CR11;

[0639] X4'is selected from N or CR12;

[0640] X5'is selected from N or CR13;

[0641] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; R3is selected from CH3, CF3, CF2H, more preferably from CH3, and CF3, and most preferably from CH3.

[0642] According to an embodiment, in Ligand L R1is selected from formula (Illh’),

[0643]

[0644] wherein

[0645] X1is selected from N or CR4;

[0646] X2is selected from N or CR5;

[0647] X3is selected from N or CR6;

[0648] X4is selected from N or CR7;

[0649] X5is selected from N or CR8;

[0650] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0651] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0652] R2is selected from formula (IVf ),

[0653]

[0654] wherein

[0655] X1'is selected from N or CR9;

[0656] X2'is selected from N or CR10;

[0657] X3'is selected from N or CR11;

[0658] X4'is selected from N or CR12;

[0659] X5'is selected from N or CR13; wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0660] R3is selected from CH3, CF3, CF2H, more preferably from CH3, and CF3, and most preferably from CH3.

[0661] According to an embodiment, in Ligand L R1is selected from formula (Illh”),

[0662] X2—X1

[0663] X3\\

[0664] / *

[0665]

[0666] X'X5(mi,..),

[0667] wherein

[0668] X1is selected from N or CR4;

[0669] X2is selected from N or CR5;

[0670] X3is selected from N or CR6;

[0671] X4is selected from N or CR7;

[0672] X5is selected from N or CR8;

[0673] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0674] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0675] R2is selected from formula (IVf”),

[0676]

[0677] wherein

[0678] X1'is selected from N or CR9;

[0679] X2'is selected from N or CR10; X3'is selected from N or CR11;

[0680] X4'is selected from N or CR12;

[0681] X5'is selected from N or CR13;

[0682] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0683] R3is selected from CH3, CF3, CF2H, more preferably from CH3, and CF3, and most preferably from CH3.

[0684] According to an embodiment, in the ligand of formula (II) R1is selected from formula (Illi), X2—X1

[0685] X3\\

[0686]

[0687] X4'x5(mi),

[0688] wherein

[0689] X1is selected from N or CR4;

[0690] X2is selected from N or CR5;

[0691] X3is selected from N or CR6;

[0692] X4is selected from N or CR7;

[0693] X5is selected from N or CR8;

[0694] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0695] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R2is selected from formula (IVg),

[0696]

[0697] wherein

[0698] X1'is selected from N or CR9;

[0699] X2'is selected from N or CR10;

[0700] X3'is selected from N or CR11;

[0701] X4'is selected from N or CR12;

[0702] X5'is selected from N or CR13;

[0703] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0704] and R3is selected from CH3, CF3, CF2H more preferably from CH3, and CF3, and most preferably from CH3.

[0705] According to an embodiment, in the ligand of formula (II) R1is selected from formula (ini’),

[0706] X2—X1

[0707] X3\\

[0708] X4-X5(mi’),

[0709] wherein

[0710] X1is selected from N or CR4;

[0711] X2is selected from N or CR5;

[0712] X3is selected from N or CR6; X4is selected from N or CR7;

[0713] X5is selected from N or CR8;

[0714] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0715] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0716] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0717] R2is selected from formula (IVg’),

[0718]

[0719] X^x1' (IVg’),

[0720] wherein

[0721] X1'is selected from N or CR9;

[0722] X2'is selected from N or CR10;

[0723] X3'is selected from N or CR11;

[0724] X4'is selected from N or CR12;

[0725] X5'is selected from N or CR13;

[0726] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0727] and R3is selected from CH3, CF3, CF2H more preferably from CH3, and CF3, and most preferably from CH3. According to an embodiment, in the ligand of formula (II) R1is selected from formula (Illi”),

[0728] x2-x1

[0729] x3\\

[0730] \4 / *

[0731]

[0732] X

[0733] A.

[0734] (Illi ),

[0735] wherein

[0736] X1is selected from N or CR4;

[0737] X2is selected from N or CR5;

[0738] X3is selected from N or CR6;

[0739] X4is selected from N or CR7;

[0740] X5is selected from N or CR8;

[0741] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0742] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0743] wherein at least three of X1, X2, X3, X4, and X5are selected from CF;

[0744] R2is selected from formula (IVg”),

[0745]

[0746] X^x1' (IVg”),

[0747] wherein

[0748] X1'is selected from N or CR9;

[0749] X2'is selected from N or CR10;

[0750] X3'is selected from N or CR11;

[0751] X4'is selected from N or CR12;

[0752] X5'is selected from N or CR13; wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0753] wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0754] and R3is selected from CH3, CF3, CF2H more preferably from CH3, and CF3, and most preferably from CH3.

[0755] According to an embodiment, in ligand L R1is selected from formula (IIIj),

[0756] X^X1

[0757] X3\\

[0758] \4 / *

[0759]

[0760] X" X5(Illj),

[0761] wherein

[0762] X1is selected from N or CR4;

[0763] X2is selected from N or CR5;

[0764] X3is selected from N or CR6;

[0765] X4is selected from N or CR7;

[0766] X5is selected from N or CR8;

[0767] wherein R4, R5, R6,R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO;

[0768] R2is selected from formula (IVh), / 4L-x='

[0769]

[0770] x2-x1' (ivh),

[0771] wherein

[0772] X1'is selected from N or CR9;

[0773] X2'is selected from N or CR10;

[0774] X3'is selected from N or CR11;

[0775] X4'is selected from N or CR12;

[0776] X5'is selected from N or CR13;

[0777] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; and R3is selected from CH3, CF3, CF2H.

[0778] According to an embodiment, in ligand L R1is selected from formula (Illj ’), / 'X1

[0779] x3W

[0780]

[0781] wherein

[0782] X1is selected from N or CR4;

[0783] X2is selected from N or CR5;

[0784] X3is selected from N or CR6;

[0785] X4is selected from N or CR7;

[0786] X5is selected from N or CR8;

[0787] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO; wherein at least three of X1, X2, X3, X4, and X5is selected from CF;

[0788] R2is selected from formula (IVh’),

[0789]

[0790] wherein

[0791] X1'is selected from N or CR9;

[0792] X2'is selected from N or CR10;

[0793] X3'is selected from N or CR11;

[0794] X4'is selected from N or CR12;

[0795] X5'is selected from N or CR13;

[0796] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; and R3is selected from CH3, CF3, CF2H.

[0797] According to an embodiment, in ligand L R1is selected from formula (Illj ”),

[0798] x2-x1

[0799] x3\\

[0800] \4 / *

[0801]

[0802] X" X5(Illj”),

[0803] wherein

[0804] X1is selected from N or CR4;

[0805] X2is selected from N or CR5;

[0806] X3is selected from N or CR6;

[0807] X4is selected from N or CR7;

[0808] X5is selected from N or CR8; wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO;

[0809] wherein at least three of X1, X2, X3, X4, and X5is selected from CF;

[0810] R2is selected from formula (IVh”),

[0811] z^X*

[0812] x’r')■

[0813]

[0814] x=x’'

[0815] wherein

[0816] X1'is selected from N or CR9;

[0817] X2'is selected from N or CR10;

[0818] X3'is selected from N or CR11;

[0819] X4'is selected from N or CR12;

[0820] X5'is selected from N or CR13;

[0821] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0822] and R3is selected from CH3, CF3, CF2H.

[0823] According to an embodiment, in ligand L R1is selected from formula (Illk), X2—X1

[0824] X3\\

[0825] \ „ / *

[0826]

[0827] X'X5(mk),

[0828] wherein

[0829] X1is selected from N or CR4;

[0830] X2is selected from N or CR5;

[0831] X3is selected from N or CR6;

[0832] X4is selected from N or CR7;

[0833] X5is selected from N or CR8;

[0834] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0835] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0836] R2is selected from formula (IVi),

[0837]

[0838] wherein

[0839] X1'is selected from N or CR9;

[0840] X2'is selected from N or CR10;

[0841] X3'is selected from N or CR11;

[0842] X4'is selected from N or CR12;

[0843] X5'is selected from N or CR13; wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0844] and R3is selected from CH3, CF3, CF2H.

[0845] According to an embodiment, in ligand L R1is selected from formula (Illk’), X2—X1

[0846] X3\\

[0847] / *

[0848]

[0849] X~x5(ink.),

[0850] wherein

[0851] X1is selected from N or CR4;

[0852] X2is selected from N or CR5;

[0853] X3is selected from N or CR6;

[0854] X4is selected from N or CR7;

[0855] X5is selected from N or CR8;

[0856] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0857] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2

[0858] wherein at least three of X1, X2, X3, X4, and X5is selected from CF;

[0859] R2is selected from formula (IVi’),

[0860]

[0861] wherein

[0862] X1'is selected from N or CR9;

[0863] X2'is selected from N or CR10;

[0864] X3'is selected from N or CR11;

[0865] X4'is selected from N or CR12;

[0866] X5'is selected from N or CR13;

[0867] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0868] and R3is selected from CH3, CF3, CF2H.

[0869] According to an embodiment, in ligand L R1is selected from formula (Illk”),

[0870] ,x2-x1

[0871] X3\\

[0872] c / *

[0873]

[0874] X'X5(ink-.),

[0875] wherein

[0876] X1is selected from N or CR4;

[0877] X2is selected from N or CR5;

[0878] X3is selected from N or CR6;

[0879] X4is selected from N or CR7;

[0880] X5is selected from N or CR8; wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0881] wherein the one or more substituents on R4, R5, R6,R7, and R8are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0882] wherein at least three of X1, X2, X3, X4, and X5is selected from CF;

[0883] R2is selected from formula (IVi”),

[0884] / 'X5'

[0885] 1 y

[0886]

[0887] x=x*'

[0888] wherein

[0889] X1'is selected from N or CR9;

[0890] X2'is selected from N or CR10;

[0891] X3'is selected from N or CR11;

[0892] X4'is selected from N or CR12;

[0893] X5'is selected from N or CR13;

[0894] wherein R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2; wherein the one or more substituents on R9, R10, R11, R12, and R13are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;

[0895] wherein at least one of X1, X2, X3, X4, and X5is selected from CF; preferably at least two of X1, X2, X3, X4, and X5are selected from CF; more preferably at least three of X1, X2, X3, X4, and X5are selected from CF;

[0896] and R3is selected from CH3, CF3, CF2H. According to an embodiment, in ligand L R1is selected from formula (film),

[0897] x2-x1

[0898] x3\\

[0899] \4 / *

[0900]

[0901] X ~~'Y5

[0902] * (film),

[0903] wherein

[0904] X1is selected from N or CR4;

[0905] X2is selected from N or CR5;

[0906] X3is selected from N or CR6;

[0907] X4is selected from N or CR7;

[0908] X5is selected from N or CR8;

[0909] wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0910] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2;

[0911] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, or NO2.

[0912] According to an embodiment, in ligand L R1is selected from formula (film’),

[0913] X2—X1

[0914] X3\\

[0915]

[0916] wherein

[0917] X1is selected from N or CR4;

[0918] X2is selected from N or CR5;

[0919] X3is selected from N or CR6;

[0920] X4is selected from N or CR7;

[0921] X5is selected from N or CR8; wherein R4, R5, R6’R7, and R8, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2;

[0922] wherein at least three of X1, X2, X3, X4, and X5is selected from CF;

[0923] R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2;

[0924] R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, or NO2.

[0925] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm) and (Illm’) at least one of R4, R5, R6, R7, and R8, if present, is independently selected from F, preferably at least two are independently selected from F, preferably at least three are independently selected from F.

[0926] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm) and (Illm’) at least one of X1, X2, X3, X4and X5, is independently selected from CF, preferably at least two are independently selected from CF, more preferably at least three are independently selected from CF.

[0927] According to an embodiment, in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) at least one of R9, R10, R11, R12, and R13, if present, is independently selected from F, preferably at least two are independently selected from F, preferably at least three are independently selected from F.

[0928] According to an embodiment, in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) at least one of X1, X2, X3, X4and X5, if present, is independently selected from CF, preferably at least two are independently selected from CF, more preferably at least three are independently selected from CF.

[0929] According to an embodiment, at least one of R4, R5, R6, R7, and R8, if present, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm), and (Illm’) or at least one of R9, R10, R11, R12, and R13in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) is independently selected from F, preferably at least two are independently selected from F, preferably at least three are independently selected from F. According to an embodiment, at least one of X1, X2, X3, X4and X5in formulae (III), (Illa) to (Illk), (IHb’) to (Illk’), (Illd”) to (Illk”), (Illm), and (Illm’) or at least one of X1, X2, X3, X4and X5in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”), is independently selected from CF, preferably at least two are independently selected from CF, more preferably at least three are independently selected from CF.

[0930] According to an embodiment, at least one of R4, R5, R6, R7, and R8, if present, in formulae (III), (Illa) to (Illk), (IHb’) to (Illk’), (Hid”) to (Illk”), (Illm), and (Illm’) and at least one of R9, R10, R11, R12, and R13in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) is independently selected from F, preferably at least two are independently selected from F, preferably at least three are independently selected from F.

[0931] According to an embodiment, at least one of X1, X2, X3, X4and X5in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm), and (Illm’) and at least one of X1, X2, X3, X4and X5in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) is independently selected from CF, preferably at least two are independently selected from CF, more preferably at least three are independently selected from CF.

[0932] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm), and (Illm’) R4, and R8, if present, are independently selected from H, D, and F; and wherein R5, R6, and R7, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

[0933] According to an embodiment, in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) R9, and R13, if present, are independently selected from H, D, and F; and

[0934] R10, R11, and R12, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

[0935] According to an embodiment, in formulae (III), (IV), (Illa) to (Illk), (Illb’) to (Illk’), (Hid”) to (Illk”), (Illm), (Illm’), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) R4, R8, R9, and R13, if present, are independently selected from H, D, and F; and

[0936] R5, R6, R7, R10, R11, and R12, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted G, to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

[0937] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (Illm), and (Illm’) at least one of X1, and X5are independently selected from CH, CD, CF or N.

[0938] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (Illm), and (Illm’) X1, and X5are independently selected from CH, CD, CF or N.

[0939] According to an embodiment, in formulae (III), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (Illm), and (Illm’) at least one of X1, and X5are independently selected from CH, CD, CF or N.

[0940] According to an embodiment, in formulae (IV), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) X1, and X5are independently selected from CH, CD, CF or N.

[0941] According to an embodiment, in formulae (III), (IV), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (Illm), (Illm’), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) at least one of X1, and X5, and at least one of X1and X5are independently selected from CH, CD, CF or N.

[0942] According to an embodiment, in formulae (III), (IV), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (Illm), (Illm’), and (IVa) to (IVi) X1, X5, X1and X5are independently selected from CH, CD, CF or N.

[0943] According to an embodiment, in formulae (III), (IV), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) at least one of X1, X5, X1and X5, if present, are independently selected from CH, CD, CF or N.

[0944] According to an embodiment, in formulae (III), (IV), (Illa) to (Illk), (Illb’) to (Illk’), (Illd”) to (Illk”), (IVa) to (IVi), (IVb’) to (IVi’) and (IVb”) to (IVi”) X1, X5, X1’ and X5’, if present, are independently selected from CH, CD, CF or N.

[0945] According to an embodiment, at least one of R1, R2, and R3is independently selected from Fl to F25

[0946]

[0947]

[0948] According to an embodiment, at least one of R1, R2, and R3is independently selected from Fl to F24.

[0949] According to an embodiment, at least one of R1or R2is independently selected from Fl to F25.

[0950] According to an embodiment, at least one of R1or R2is independently selected from Fl to F24

[0951] According to an embodiment, wherein the at least one of R1, and R2selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F25.

[0952] According to an embodiment, wherein the at least one of R1, and R2selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F24; preferably Fl to F9, more preferably Fl to F7, most preferably Fl to F6.

[0953] According to an embodiment, wherein R1is selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl. According to an embodiment, wherein R1selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F25.

[0954] According to an embodiment, wherein R1selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F24; preferably Fl to F9, more preferably Fl to F7, most preferably Fl to F6.

[0955] According to an embodiment, one of the remaining R1, R2, and R3(= that is not selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl) is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl.

[0956] By doing so, the rise of the operational voltage over time may be reduced, i.e. improved. According to an embodiment, at least one of R1, R2, and R3is independently selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; and

[0957] one of the remaining R1, R2, and R3is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl.

[0958] By doing so, the rise of the operational voltage over time may be reduced, i.e. improved. According to an embodiment, the at least one of R1, R2, and R3is independently selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F25; and

[0959] wherein one of the remaining R1, R2, and R3is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl.

[0960] By doing so, the rise of the operational voltage over time may be reduced, i.e. improved. According to an embodiment, the at least one of R1, R2, and R3is independently selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F24; and

[0961] wherein one of the remaining R1, R2, and R3is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl.

[0962] By doing so, the rise of the operational voltage over time may be reduced, i.e. improved. According to an embodiment, at least one of R1, and R2is independently selected from an aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; and

[0963] wherein one of the remaining R1, and R2is selected from substituted or unsubstituted C6to C19aryl, substituted or unsubstituted C2to C20heteroaryl.

[0964] By doing so, the rise of the operational voltage over time may be even more reduced, i.e. improved.

[0965] According to an embodiment, the at least one of R1, and R2is independently selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F25; and wherein one of the remaining R1, and R2is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl.

[0966] By doing so, the rise of the operational voltage over time may be even more reduced, i.e. improved.

[0967] According to an embodiment, the at least one of R1, and R2is independently selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl is independently selected from Fl to F24; and wherein one of the remaining R1, and R2is selected from substituted or unsubstituted C6to C19aryl, substituted or unsubstituted C2to C20heteroaryl.

[0968] By doing so, the rise of the operational voltage over time may be even more reduced, i.e. improved.

[0969] According to an embodiment, wherein the aryl or heteroaryl of the at least one aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl in ligand L is selected from phenyl, pyridyl, or pyrimidyl, preferably from phenyl, or pyridyl, more preferably from phenyl.

[0970] In other words, according to an embodiment L comprises at least one phenyl, or pyridyl, pyrimidyl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; preferably L comprises at least one phenyl, or pyridyl, comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; and more preferably L comprises at least one phenyl comprising at least one F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl. According to one embodiment, wherein the aryl or heteroaryl of the at least one of R1, R2, and R3comprising at least three F groups directly bonded to a sp2-hydridized carbon atom of the ring of the aryl or of the heteroaryl is selected from phenyl, pyridyl, or pyrimidyl, preferably from phenyl, or pyridyl, more preferably from phenyl.

[0971] In other words, according to an embodiment at least one of R1, R2, and R3is selected from phenyl, pyridyl, or pyrimidyl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; preferably at least one of R1, R2, and R3is selected from phenyl, or pyridyl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; and more preferably at least one of R1, R2, and R3is selected from phenyl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl.

[0972] According to an embodiment, R1and / or R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae El to E67

[0973]

[0974]

[0975] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E67; and or from formula E1 to E67.

[0976] According to an embodiment, R1and / or R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae E1 to E66

[0977] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E66; and

[0978] R3. is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E66.

[0979] According to an embodiment, R1is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26, and E67;

[0980] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26, and E67; and

[0981] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26, and E67.

[0982] According to an embodiment, R1is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26;

[0983] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26; and

[0984] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E26.

[0985] According to an embodiment, R1is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E24, and E67,

[0986] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E24, and E67; and

[0987] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula E1 to E24, and E67. According to an embodiment, R11 s selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula El to E24,

[0988] R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula El to E24; and

[0989] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formula El to E24.

[0990] According to an embodiment, R1and / or R2is selected from formulae G1 to G16

[0991]

[0992] According to an embodiment, R1and / or R2is selected from formulae G1 to G15.

[0993] According to an embodiment, R1and / or R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae H1 to H19

[0994]

[0995]

[0996] and R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae H1 to H19.

[0997] According to an embodiment, R2is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae H1 to H17; and R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or from formulae H1 to H17.

[0998] According to an embodiment, R1is selected from formulae G1 to G16

[0999]

[1000] R2is selected from CF3, formulae H1 to H19

[1001]

[1002] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2; preferably from CH3, CF3, and CF2H, more preferably from CH3, and CF3and most preferably from CH3.

[1003] According to an embodiment, R1is selected from formulae G1 to G15;

[1004] R2is selected from CF3, formulae H1 to H19; and

[1005] R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2; preferably from CH3, CF3, and CF2H, more preferably from CH3, and CF3and most preferably from CH3.

[1006] According to an embodiment, R1is selected from formulae G1 to G16;

[1007] wherein R2is selected from CF3, or formulae H1 to H17; and

[1008] wherein R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2; preferably from CH3, CF3, and CF2H, more preferably from CH3, and CF3, and most preferably from CH3.

[1009] According to an embodiment, R1is selected from formulae G1 to G15;

[1010] wherein R2is selected from CF3, or formulae H1 to H17; and wherein R3is selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2; preferably from CH3, CF3, and CF2H, more preferably from CH3, and CF3;and most preferably from CH3.

[1011] According to an embodiment, the ligand L and / or the ligand of formula (II) further comprises at least one group selected from F, CN, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[1012] According to an embodiment, the ligand L and / or the ligand of formula (II) further comprises at least one group selected from F, CN, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl.

[1013] According to an embodiment, the ligand L and / or the ligand formula (II) further comprises ≥2 to ≤10 groups selected from F, CN, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl; preferably ≥3 to ≤10 groups, more preferably 4≥ to ≤10 groups.

[1014] Amount of CN groups in ligand L and / or formula (II)

[1015]

[1016] According to an embodiment, the ligand L and / or the ligand of formula (II) comprises 0≥ to ≤ 4 CN groups, preferably 0≥ to ≤ 3 CN groups, more preferably 0≥ to ≤ 2 CN groups, and most preferably no or one CN groups.

[1017] According to an embodiment, the ligand L and / or the ligand of formula (II) comprises 0≥ to ≤ 4 CN groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl, preferably 0≥ to ≤ 3 CN groups, more preferably 0≥ to ≤ 2 CN groups, and most preferably no or one CN groups.

[1018] Compounds of formula (I)

[1019] According to an embodiment, the compound of formula (I) is selected from Al to A60, Bl to B12, Cl to C7, DI to D23:

[1020]

[1021]

[1022]

[1023]

[1024]

[1025]

[1026]

[1027]

[1028] D19,

[1029]

[1030] According to an embodiment, the compound of formula (I) is selected from Al, A2, A4 to A60, Bl to B12, Cl to C7, DI to D23:

[1031] According to an embodiment, where the compounds of formula (I) are selected from Al, to A60, Bl to B12, Cl to C7, and DI to D19.

[1032] According to an embodiment, where the compounds of formula (I) are selected from Al, A2, A4 to A60, Bl to B12, Cl to C7, and DI to D19.

[1033] According to a preferred embodiment, wherein the compounds of formula (I) are selected from Al to A60, Bl to 12, and Cl to C7.

[1034] According to a preferred embodiment, wherein the compounds of formula (I) are selected from Al, A2, A4 to 60, Bl to 12, and Cl to C7.

[1035] According to a more preferred embodiment, wherein the compounds of formula (I) are selected from Al to A60, and B1 to B12.

[1036] According to a more preferred embodiment, wherein the compounds of formula (I) are selected from Al, A2, A4 to A60, and B1 to B12. According to a most preferred embodiment, wherein the compounds of formula (I) are selected from Al to A60.

[1037] According to a most preferred embodiment, wherein the compounds of formula (I) are selected from Al to A60.

[1038] According to one embodiment, wherein the ligand L of formula (I) may be selected from a group comprising at least 12 carbon atoms and at most 21 carbon atoms, alternatively at least 12 carbon atoms and at most 20 carbon atoms, alternatively at least 12 carbon atoms and at most 19 carbon atoms, alternatively at least 12 carbon atoms and at most 18 carbon atoms, alternatively at least 12 carbon atoms and at most 17 carbon atoms.

[1039] According to one embodiment, wherein the metal complex of formula (I) has a LUMO energy level in the range from >-4.10 eV to < -1.0 eV; preferably in the range of >-4.0 eV to < -1.5 eV; more preferably >-3.9 eV to < -1.6 eV; and most preferably >-3.8 eV to < -1.7 eV.

[1040] According to an embodiment, wherein the energy gap Egap (difference between LUMO energy level and the HOMO energy level) is > 3.1 eV; preferably >3.2 eV, and more preferably >3.3 eV.

[1041] Ancillary ligand AL and term “m”

[1042] The term “m” is an integer selected from 0 to 2, i.e. “m” is an integer selected from 0, 1, or 2.

[1043] According to an embodiment “m” is an integer selected from 0 or 1. According to another embodiment “m” is an integer selected from 1.

[1044] According to an embodiment, “m” is an integer selected from 2.

[1045] According to an embodiment, “m” is an integer selected from 1.

[1046] According to an embodiment, “m” is an integer preferably selected from 0.

[1047] According to one embodiment, AL is charge-neutral.

[1048] According to one embodiment of Formula (I), AL is selected from the group comprising H2O, C2to C40mono- or multi-dentate ethers and C2to C40thioethers, C2to C40amines, C2to C40phosphines, C2to C20alkyl nitriles or C2to C40aryl nitriles, or a compound according to Formula (XX); R20

[1049] R21\N

[1050] R21^N

[1051]

[1052] R20(XX), wherein

[1053] R20and R21are independently selected from C1to C20alkyl, C1to C20heteroalkyl, C6to C20aryl, heteroaryl with 5 to 20 ring-forming atoms, halogenated or perhalogenated C1to C20alkyl, halogenated or perhalogenated C1to C20heteroalkyl, halogenated or perhalogenated C6to C20aryl, halogenated or perhalogenated heteroaryl with 5 to 20 ring-forming atoms, or at least one R20and R21are bridged and form a 5 to 20 member ring, or the two R20and / or the two R21are bridged and form a 5 to 40 member ring or form a 5 to 40 member ring comprising an unsubstituted or C1to C12substituted phenanthroline.

[1054] According to one embodiment of the application AL is H2O and m is 1.

[1055] Uses of the inventive compound

[1056] The present invention furthermore relates to the use of a compound of formula (I) in an organic device.

[1057] The present invention furthermore relates to the use of a compound of formula (I) in an organic semiconductor layer.

[1058] The present invention further more relates to the use of a compound of formula (I) as a p-dopant.

[1059] All preferred embodiments of the compound of formula (I) may apply ad libitum.

[1060] Semiconductor material

[1061] According to another aspect, a semiconductor material is provided which comprises at least one compound of Formula (I) according to the present invention.

[1062] According to one embodiment, the semiconductor material comprises in addition at least one covalent matrix compound or at least one substantially covalent matrix compound. According to another aspect, a semiconductor material comprises at least one compound of Formula (I) according to the present invention and in addition at least one covalent matrix compound or at least one substantially covalent matrix compound.

[1063] Organic semiconductor layer

[1064] According to another aspect, an organic semiconductor layer is provided which comprises at least one compound of Formula (I) according to the present invention.

[1065] According to one embodiment of the invention, the organic semiconductor layer is a hole injection layer.

[1066] The organic semiconductor layer may be formed on the anode layer or cathode layer by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like. When the organic semiconductor layer is formed using vacuum deposition, the deposition conditions may vary according to the compound(s) that are used to form the layer, and the desired structure and thermal properties of the layer. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 350° C, a pressure of 10-8to 10-3Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm / sec.

[1067] When the organic semiconductor layer is formed using spin coating or printing, coating conditions may vary according to the compound(s) that are used to form the layer, and the desired structure and thermal properties of the organic semiconductor layer. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.

[1068] The thickness of the organic semiconductor layer may be in the range from about 1 nm to about 20 nm, and for example, from about 2 nm to about 15 nm, alternatively about 2 nm to about 12 nm.

[1069] When the thickness of the organic semiconductor layer is within this range, the organic semiconductor layer may have excellent hole injecting and / or hole generation characteristics, without a substantial penalty in driving voltage.

[1070] According to one embodiment of the present invention, the organic semiconductor layer may comprise: - at least about > 0.5 wt.-% to about < 30 wt.-%, preferably about > 0.5 wt.-% to about < 20 wt.- %, and more preferred about > 1 wt.-% to about < 15 wt.-% of a compound of Formula (I), and

[1071] - at least about > 70 wt.-% to about < 99.5 wt.-%, preferably about > 80 wt.-% to about < 99.5 wt.-%, and more preferred about > 85 wt.-% to about < 99 wt.-% of a substantially covalent matrix compound; preferably the wt.-% of the compound of Formula (I) is lower than the wt.- % of the substantially covalent matrix compound; wherein the weight-% of the components are based on the total weight of the organic semiconductor layer.

[1072] According to one embodiment of the present invention the organic semiconductor layer and / or the compound of Formula (I) are non-emissive.

[1073] In the context of the present specification the term “essentially non-emissive” or “non-emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10%, preferably less than 5 % relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of about > 380 nm to about < 780 nm.

[1074] Substantially covalent matrix compound / covalent matrix compound

[1075] According to another aspect of the present invention, the semiconductor material and / or the organic semiconductor layer may further comprise a substantially covalent matrix compound.

[1076] The substantially covalent matrix compound, also named matrix compound, may be an organic aromatic matrix compounds, which comprises organic aromatic covalent bonded carbon atoms. The substantially covalent matrix compound may be an organic compound, consisting substantially from covalently bound C, H, O, N, S, which may optionally comprise also covalently bound B, P or Si. The substantially covalent matrix compound may be an organic aromatic covalent bonded compound, which is free of metal atoms, and the majority of its skeletal atoms may be selected from C, O, S, N and preferably from C, O and N, wherein the majority of atoms are C-atoms. Alternatively, the covalent matrix compound is free of metal atoms and majority of its skeletal atoms may be selected from C and N, preferably the covalent matrix compound is free of metal atoms and majority of its skeletal atoms may be selected from C and the minority of its skeletal atoms may be N.

[1077] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of > 400 and < 2000 g / mol, preferably a molecular weight Mw of > 450 and < 1500 g / mol, further preferred a molecular weight Mw of > 500 and < 1000 g / mol, in addition preferred a molecular weight Mw of > 550 and < 900 g / mol, also preferred a molecular weight Mw of > 600 and < 800 g / mol.

[1078] In one embodiment, the HOMO level of the substantially covalent matrix compound may be more negative than the HOMO level of N2, N2, N2', N2', N7, N7, N7', N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine (CAS 207739-72-8) when determined under the same conditions.

[1079] In one embodiment of the present invention, the substantially covalent matrix compound may be free of alkoxy groups.

[1080] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, alternatively a diarylamine moiety, alternatively a triarylamine moiety.

[1081] Preferably, the substantially covalent matrix compound is free of TPD or NPB.

[1082] Compound of formula (IXa) or a compound of formula (IXb)

[1083] According to another aspect of the present invention, the substantially covalent matrix compound or covalent matrix compound, also referred to as matrix compound herein, may comprises at least one arylamine compound, diarylamine compound, triarylamine compound, a compound of formula (IXa) or a compound of formula (IXb):

[1084] Ari Ari Ar4

[1085] T\ T\ T4^

[1086] N — T3— Ar3N — T6— l\f

[1087] zT2

[1088] Ar2

[1089]

[1090] (ixa), Ar27*XAr5(ixb), wherein:

[1091] T1, T2, T3, T4and T5are independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthenylene, preferably a single bond or phenylene; T6is phenylene, biphenylene, terphenylene or naphthenylene;

[1092] Ar1, Ar2, Ar3, Ar4and Ar5are independently selected from substituted or unsubstituted C6to C20aryl, or substituted or unsubstituted C3to C20heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted 9- fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted tetracene, substituted or unsubstituted tetraphene, substituted or unsubstituted dibenzofurane, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted

[1093] dibenzo [b,f] azepine, substituted or unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted spiro [fluorene-9, 9' -xanthene], or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from the group comprising substituted or unsubstituted non- hetero, substituted or unsubstituted hetero 5-member rings, substituted or unsubstituted 6-member rings and / or substituted or unsubstituted 7-member rings, substituted or unsubstituted fluorene, or a fused ring system comprising 2 to 6 substituted or unsubstituted 5- to 7-member rings and the rings are selected from the group comprising (i) unsaturated 5- to 7-member ring of a heterocycle, (ii) 5- to 6- member of an aromatic heterocycle, (IX) unsaturated 5- to 7-member ring of a nonheterocycle, (iv) 6-member ring of an aromatic non-heterocycle;

[1094] wherein

[1095] the substituents of Ar1, Ar2, Ar3, Ar4and Ar5are selected the same or different from the group comprising H, D, F, C(-O)R2, CN, Si(R2)3, P(-O)(R2)2, OR2, S(-O)R2, S(-O)2R2, substituted or unsubstituted straight-chain alkyl having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6to C18aryl, unsubstituted C3to C18heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5- to 7-member rings and the rings are selected from the group comprising unsaturated 5- to 7-member ring of a heterocycle, 5- to 6-member of an aromatic heterocycle, unsaturated 5- to 7-member ring of a non-heterocycle, and 6-member ring of an aromatic non-heterocycle,

[1096] wherein R2may be selected from H, D, straight-chain alkyl having 1 to 6 carbon atoms, branched alkyl having 1 to 6 carbon atoms, cyclic alkyl having 3 to 6 carbon atoms, alkenyl or alkynyl groups having 2 to 6 carbon atoms, C6to C18aryl or C3to C18heteroaryl.

[1097] Preferably, the substituents of Ar1, Ar2, Ar3, Ar4and Ar5are selected the same or different from the group comprising H, straight-chain alkyl having 1 to 6 carbon atoms, branched alkyl having 1 to 6 carbon atoms, cyclic alkyl having 3 to 6 carbon atoms, alkenyl or alkynyl groups having 2 to 6 carbon atoms, C6to C18aryl, C3to C18heteroaryl, a fused ring system comprising 2 to 4 unsubstituted 5- to 7-member rings and the rings are selected from the group comprising unsaturated 5- to 7-member ring of a heterocycle, 5- to 6-member of an aromatic heterocycle, unsaturated 5- to 7-member ring of a non-heterocycle, and 6-member ring of an aromatic nonheterocycle; more preferred the substituents are selected the same or different from the group consisting of H, straight-chain alkyl having 1 to 4 carbon atoms, branched alkyl having 1 to 4 carbon atoms, cyclic alkyl having 3 to 4 carbon atoms and / or phenyl.

[1098] Thereby, the compound of formula (IXa) or (IXb) may have a rate onset temperature suitable for mass production.

[1099] According to an embodiment of the semiconductor material and / or organic semiconductor layer, wherein the substantially covalent matrix compound comprises a compound of formula (IXa) or formula (IXb):

[1100] Ar1Ar1Ar4

[1101] T\ T4^

[1102] N — T3— Ar3N — T6—

[1103] zT2ZT2

[1104]

[1105] Ar2(ixa), Ar2 XAr5(ixb), wherein

[1106] T1, T2, T3, T4and T5may be independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthenylene, preferably a single bond or phenylene; T6is phenylene, biphenylene, terphenylene or naphthenylene;

[1107] Ar1, Ar2, Ar3, Ar4and Ar5may be independently selected from unsubstituted C6to C20aryl, or unsubstituted C3to C20heteroarylene, unsubstituted biphenylene, unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, unsubstituted naphthalene, unsubstituted anthracene, unsubstituted phenanthrene, unsubstituted pyrene, unsubstituted perylene, unsubstituted triphenylene, unsubstituted tetracene, unsubstituted tetraphene, unsubstituted dibenzofurane, unsubstituted dibenzothiophene, unsubstituted xanthene, unsubstituted carbazole, substituted 9-phenylcarbazole, unsubstituted azepine, unsubstituted dibenzo[b,f]azepine, unsubstituted 9,9'-spirobi[fluorene], unsubstituted spiro [fluorene-9, 9' -xanthene], or a unsubstituted aromatic fused ring system comprising at least three unsubstituted aromatic rings selected from the group comprising unsubstituted non-hetero, unsubstituted hetero 5-member rings, unsubstituted 6-member rings and / or unsubstituted 7-member rings, unsubstituted fluorene, or a fused ring system comprising 2 to 6 unsubstituted 5- to 7-member rings and the rings are selected from the group comprising (i) unsaturated 5- to 7-member ring of a heterocycle, (ii) 5- to 6-member of an aromatic heterocycle, (IX) unsaturated 5- to 7- member ring of a non-heterocycle, (iv) 6-member ring of an aromatic nonheterocycle.

[1108] According to an embodiment of the semiconductor material and / or organic semiconductor layer, wherein the substantially covalent matrix compound comprises a compound of formula (IXa) or formula (IXb):

[1109] Ar1Ar1Ar4

[1110] T\ T4^

[1111] N — T3— Ar3N — T6—

[1112] zT2ZT2

[1113]

[1114] Ar2(ixa), Ar2 XAr5(ixb), wherein

[1115] T1, T2, T3, T4and T5may be independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthenylene, preferably a single bond or phenylene; T6is phenylene, biphenylene, terphenylene or naphthenylene;

[1116] Ar1, Ar2, Ar3, Ar4and Ar5may be independently selected from unsubstituted C6to C20aryl, or unsubstituted C3to C20heteroarylene, unsubstituted biphenylene, unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, unsubstituted naphthalene, unsubstituted anthracene, unsubstituted phenanthrene, unsubstituted pyrene, unsubstituted perylene, unsubstituted triphenylene, unsubstituted tetracene, unsubstituted tetraphene, unsubstituted dibenzofurane, unsubstituted dibenzothiophene, unsubstituted xanthene, unsubstituted carbazole, substituted 9-phenylcarbazole, unsubstituted azepine, unsubstituted dibenzo[b,f]azepine, unsubstituted 9,9'-spirobi[fluorene], unsubstituted spiro [fluorene-9, 9' -xanthene].

[1117] Thereby, the compound of formula (IXa) or (IXb) may have a rate onset temperature suitable for mass production.

[1118] According to an embodiment wherein T1, T2, T3, T4and T5may be independently selected from a single bond, phenylene, biphenylene or terphenylene.

[1119] According to an embodiment wherein T1, T2, T3, T4and T5may be independently selected from phenylene, biphenylene or terphenylene and one of T1, T2, T3, T4and T5are a single bond.

[1120] According to an embodiment wherein T1, T2, T3, T4and T5may be independently selected from phenylene or biphenylene and one of T1, T2, T3, T4and T5are a single bond.

[1121] According to an embodiment wherein T1, T2, T3, T4and T5may be independently selected from phenylene or biphenylene and two of T1, T2, T3, T4and T5are a single bond.

[1122] According to an embodiment wherein T1, T2and T3may be independently selected from phenylene and one of T1, T2and T3are a single bond.

[1123] According to an embodiment wherein T1, T2and T3may be independently selected from phenylene and two of T1, T2and T3are a single bond.

[1124] According to an embodiment wherein T6may be phenylene, biphenylene, terphenylene. According to an embodiment wherein T6may be phenylene.

[1125] According to an embodiment wherein T6may be biphenylene. According to an embodiment wherein T6may be terphenylene.

[1126] According to an embodiment wherein Ar1, Ar2, Ar3, Ar4and Ar5may be independently selected from formulae (II) to (116):

[1127]

[1128]

[1129] wherein the asterix denotes the binding position.

[1130] According to an embodiment, Ar1, Ar2, Ar3, Ar4and Ar5may be independently selected from (II) to (115); alternatively selected from (II) to (110) and (113) to (115).

[1131] According to an embodiment, Ar1, Ar2, Ar3, Ar4and Ar5may be independently selected from the group consisting of (II), (12), (15), (17), (19), (110), (113) to (116).

[1132] The rate onset temperature may be in a range particularly suited to mass production, when Ar1, Ar2, Ar3, Ar4and Ar5are selected in this range.

[1133] The “matrix compound of formula (IXa) or formula (IXb) “ may be also referred to as “hole transport compound”.

[1134] According to one embodiment the compound of formula (IXa) or formula (IXb) may comprises at least > 1 to < 6 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings.

[1135] According to one embodiment the compound of formula (IXa) or formula (IXb) may comprise at least > 1 to < 6 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings and at least > 1 to < 3 substituted or unsubstituted unsaturated 5- to 7-member ring of a heterocycle, preferably > 2 to < 5 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings.

[1136] According to one embodiment the compound of formula (IXa) or formula (IXb) may comprises at least > 1 to < 6 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings and at least > 1 to < 3 substituted or unsubstituted unsaturated 5- to 7-member ring of a heterocycle, preferably > 2 to < 5 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings, and at least > 1 to < 3 substituted or unsubstituted unsaturated 5- to 7-member ring of a heterocycle, further preferred 3 or 4 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings and optional at least > 1 to < 3 substituted or unsubstituted unsaturated 5- to 7-member ring of a heterocycle, and additional preferred wherein the aromatic fused ring systems comprising heteroaromatic rings are unsubstituted and optional at least > 1 to < 3 unsubstituted unsaturated 5- to 7-member ring of a heterocycle.

[1137] According to one embodiment the compound of formula (IXa) or formula (IXb) may comprises:

[1138] - a substituted or unsubstituted aromatic fused ring systems with at least > 2 to < 6, preferably > 3 to < 5, or 4 fused aromatic rings selected from the group comprising substituted or unsubstituted non-hetero aromatic rings, substituted or unsubstituted hetero 5-member rings, substituted or unsubstituted 6-member rings and / or substituted or unsubstituted unsaturated 5- to 7- member ring of a heterocycle; or

[1139] - an unsubstituted aromatic fused ring systems with at least > 2 to < 6, preferably > 3 to < 5, or 4 fused aromatic rings selected from the group comprising unsubstituted non-hetero aromatic rings, unsubstituted hetero 5-member rings, unsubstituted 6-member rings and / or unsubstituted unsaturated 5- to 7-member ring of a heterocycle.

[1140] It should be noted here that the wording “aromatic fused ring system” may include at least one aromatic ring and at least one substituted or unsubstituted unsaturated 5- to 7- member ring. It should be noted here that the substituted or unsubstituted unsaturated 5- to 7- member ring may not be an aromatic ring.

[1141] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofurane group, dibenzothiophene group and / or substituted fluorenyl group, wherein the substituents are independently selected from methyl, phenyl or fluorenyl.

[1142] According to an embodiment of the present invention, wherein the compound of formula (IXa) or formula (IXb) are selected from formulae (KI) to (K23):

[1143]

[1144]

[1145]

[1146] o (K19), (K20), (K21), (K22),

[1147]

[1148] (K23);

[1149] preferably the compound of formula (IXa) or formula (IXb) is selected from formulae (K3) to (K23), more preferred from (K4) to (K23), most preferred from (K18).

[1150] Organic electronic device

[1151] According to another aspect of the present invention, an organic electronic device is provided, wherein the organic electronic device comprises a semiconductor material, wherein at least one semiconductor material comprises a compound of Formula (I).

[1152] According to another aspect of the present invention, an organic electronic device is provided, wherein the organic electronic device comprises an organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of Formula (I).

[1153] According to one embodiment of the present invention, the organic electronic device comprising an anode layer, a cathode layer, and an organic semiconductor layer according to the invention, preferably the organic semiconductor layer is arranged between the anode layer and the cathode layer.

[1154] Preferably, the organic semiconductor layer is arranged adjacent to the anode layer, preferably the organic semiconductor layer is arranged in direct contact with the anode layer. Preferably such organic semiconductor layer is a hole injection layer.

[1155] Surprisingly it has been shown that for many applications within the present invention such an organic electronic device has improved properties, especially in view of current efficiency, external quantum efficiency, and / or a good operational voltage, and good stability such as lifetime and / or good rise of the operational voltage over time

[1156] According to one embodiment of the present invention, the organic electronic device is selected from the group comprising a light emitting device, thin film transistor, a battery, a display device, a photovoltaic cell, or an organic photodetector, and preferably a light emitting device, preferably the electronic device is part of a display device or lighting device.

[1157] According to one embodiment the organic electronic device comprises a compound according to Formula (I) of the present invention is a light emitting device, a thin film transistor, a battery, an organic photovoltaic cell (OPV), a display device, a photovoltaic device, or an organic photodetector and preferably a light emitting device, preferably the electronic device is part of a display device or lighting device.

[1158] According to one embodiment of the invention, the organic electronic devices further comprises at least one photoactive layer, wherein the at least one photoactive layer is arranged between the anode layer and the cathode layer.

[1159] According to one embodiment of the invention, the organic electronic devices comprises at least one photoactive layer and the at least one organic semiconductor layers is arranged between the anode and the at least one photoactive layer.

[1160] According to one embodiment the organic electronic device comprises an anode layer, a cathode layer, at least one photoactive layer and at least one semiconductor layer, wherein the at least one semiconductor layer is arranged between the anode layer and the at least one photoactive layer; and wherein the at least one organic semiconductor layer comprises a compound of Formula (I).

[1161] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is the organic semiconductor layer according to the present invention.

[1162] According to one embodiment of the invention, the organic semiconductor layer is arranged and / or provided adjacent to the anode layer. According to one embodiment of the invention, the organic semiconductor layer of the present invention is a hole-injection layer.

[1163] In case the semiconductor layer of the present invention is a hole-injection layer and / or is arranged and / or provided adjacent to the anode layer then it is especially preferred that this layer consists essentially of the compound of Formula (I).

[1164] In the context of the present specification the term “consisting essentially of “ especially means and / or includes a concentration of > 90% (vol / vol) more preferred > 95% (vol / vol) and most preferred > 99% (vol / vol).

[1165] According to another aspect, the semiconductor layer may have a layer thickness of at least about > 0.5 nm to about < 10 nm, preferably of about > 2 nm to about < 8 nm, also preferred of about > 3 nm to about < 5 nm.

[1166] According to one embodiment of the invention, the semiconductor layer of the present invention may further comprise a substantially covalent matrix compound. Preferably at least one semiconductor layer further comprising a substantially covalent matrix compound is arranged and / or provided adjacent to the anode layer.

[1167] According to one embodiment of the invention, the electronic organic device is an electroluminescent device, preferably an organic light emitting diode.

[1168] According to one embodiment of the invention, the electronic organic device is an electroluminescent device, preferably an organic light emitting diode and the light is emitted through the cathode layer.

[1169] The present invention furthermore relates to a display device comprising an organic electronic device according to the present invention.

[1170] According to one embodiment of the invention the electronic organic device is an electroluminescent device, preferably an organic light emitting diode.

[1171] The present invention furthermore relates to a display device comprising an organic electronic device according to the present invention.

[1172] Further layers

[1173] In accordance with the invention, the organic electronic device may comprise, besides the layers already mentioned above, further layers. Exemplary embodiments of respective layers are described in the following: Substrate

[1174] The substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate may be both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.

[1175] Anode layer

[1176] The anode layer, also named anode electrode, may be formed by depositing or sputtering a material that is used to form the anode layer. The material used to form the anode layer may be a high work-function material, so as to facilitate hole injection. The anode layer may be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin-dioxide (SnO2), aluminum zinc oxide (A1Z0) and zinc oxide (ZnO), may be used to form the anode layer. The anode layer may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.

[1177] The anode layer may comprise two or more anode sub-layers.

[1178] According to one embodiment, the anode layer comprises a first anode sub-layer and a second anode sub-layer, wherein the first anode sub-layer is arranged closer to the substrate and the second anode sub-layer is arranged closer to the cathode layer.

[1179] According to one embodiment, the anode layer may comprise a first anode sub-layer comprising or consisting of Ag or Au and a second anode-sub-layer comprising or consisting of transparent conductive oxide.

[1180] According to one embodiment, the anode layer comprises a first anode sub-layer, a second anode sub-layer and a third anode sub-layer, wherein the first anode sub-layer is arranged closer to the substrate and the second anode sub-layer is arranged closer to the cathode layer, and the third anode sub-layer is arranged between the substrate and the first anode sub-layer.

[1181] According to one embodiment, the anode layer may comprise a first anode sub-layer comprising or consisting of Ag or Au, a second anode-sub-layer comprising or consisting of transparent conductive oxide and optionally a third anode sub-layer comprising or consisting of transparent conductive oxide. Preferably the first anode sub-layer may comprise or consists of Ag, the second anode-sublayer may comprise or consists of ITO or IZO and the third anode sublayer may comprises or consists of ITO or IZO.

[1182] Preferably the first anode sub-layer may comprise or consists of Ag, the second anodesublayer may comprise or consists of ITO and the third anode sub-layer may comprise or consist of ITO.

[1183] Preferably, the transparent conductive oxide in the second and third anode sub-layer may be selected the same.

[1184] According to one embodiment, the anode layer may comprise a first anode sub-layer comprising Ag or Au having a thickness of 100 to 150 nm, a second anode sub-layer comprising or consisting of a transparent conductive oxide having a thickness of 3 to 20 nm and a third anode sub-layer comprising or consisting of a transparent conductive oxide having a thickness of 3 to 20 nm.

[1185] It is to be understood that the third anode layer is not part of the substrate.

[1186] Hole injection layer

[1187] A hole injection layer (HIL) may be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like. When the HIL is formed using vacuum deposition, the deposition conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 500° C, a pressure of 10-8to 10-3Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm / sec.

[1188] When the HIL is formed using spin coating or printing, coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.

[1189] The HIL may be formed of any compound that is commonly used to form a HIL.

[1190] Examples of compounds that may be used to form the HIL include a phthalocyanine compound, such as copper phthalocyanine (CuPc), 4,4',4"-tris (3 -methylphenylphenylamino) triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), and polyaniline) / poly(4-styrenesulfonate (PANI / PSS).

[1191] The HIL may comprise or consist of p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile or 2,2',2"-(cyclopropane-l,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) but not limited hereto. The HIL may be selected from a holetransporting matrix compound doped with a p-type dopant. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc), which HOMO level is approximately -5.2 eV, doped with tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), which LUMO level is about -5.2 eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2 eV) doped with F4TCNQ; a-NPD (N, N'-Bis(naphthalen-l-yl)-N, N'-bis(phenyl)-benzidine) doped with F4TCNQ. a-NPD doped with 2,2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile. The p-type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%.

[1192] The thickness of the HIL may be in the range from about 1 nm to about 100 nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage.

[1193] Hole transport layer

[1194] According to one embodiment of the present invention, the organic electronic device may further comprise a hole transport layer, wherein the hole transport layer is arranged between the anode layer and the cathode layer, preferably between the organic semiconductor layer of the present invention and the cathode layer.

[1195] The hole transport layer (HTL) may be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL.

[1196] The HTL may be formed of any compound that is commonly used to form a HTL.

[1197] Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and incorporated by reference. Examples of the compound that may be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N, N'-bis(3-methylphenyl)-N, N'-diphenyl-[l,l-biphenyl]-4,4'-diamine (TPD), or N, N'-di(naphthalen-l-yl)-N, N'-diphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit excitons from being diffused into the EML.

[1198] According to a preferred embodiment of the present invention, the hole transport layer may comprise a substantially covalent matrix compound.

[1199] According to one embodiment of the present invention, the hole transport layer may comprise the same substantially covalent matrix compound as the organic semiconductor layer of the present invention, preferably, the hole transport layer may comprise the same compound of formula (IXa) or (IXb) as the organic semiconductor layer of the present invention.

[1200] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably, about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. A preferred thickness of the HTL may be 170 nm to 200 nm.

[1201] When the thickness of the HTL is within this range, the HTL may have excellent hole transporting characteristics, without a substantial penalty in driving voltage.

[1202] Electron blocking layer

[1203] The function of an electron blocking layer (EBL) is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and / or lifetime may be improved.

[1204] Typically, the electron blocking layer comprises a triarylamine compound. The triarylamine compound may have a LUMO level closer to vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO level of the hole transport layer. The thickness of the electron blocking layer may be selected between 2 and 20 nm.

[1205] If the electron blocking layer has a high triplet level, it may also be described as triplet control layer. The function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used. Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved. The triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emitter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2722908 Al.

[1206] Photoactive layer (PAL)

[1207] The photoactive layer converts an electrical current into photons or photons into an electrical current.

[1208] The PAL may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like. When the PAL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the PAL.

[1209] It may be provided that the photoactive layer does not comprise the compound of Formula (I).

[1210] The photoactive layer may be an emission layer (EML), also named light-emitting layer, or a light-absorbing layer.

[1211] Emission layer (EML)

[1212] According to an embodiment, the organic electronic device of the present invention may further comprise an emission layer (EML), wherein the emission layer is arranged between the anode layer and the cathode layer, preferably the emission layer is arranged betweent the organic semiconductor layer and the cathode layer.

[1213] The EML may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the EML.

[1214] The emission layer (EML) may comprise an organic emitter host and a light-emitting compound dopant. Examples of the organic emitter host are Alq3, 4,4'-N, N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9, 10-di(naphthalene-2-yl)anthracene (ADN), 4, 4', 4"-tris(carbazol-9-yl)-triphenylamine(TCTA), l,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DS A) and bis(2-(2-hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).

[1215] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters which emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[1216] Examples of red emitter dopants are PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants could also be used.

[1217] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[1218] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and ter-fluorene. 4,4'-bis(4-diphenyl amiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butyl perylene (TBPe) are examples of fluorescent blue emitter dopants.

[1219] It may be provided that the emission layer does not comprise the compound of Formula (I).

[1220] The amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight of the host. Alternatively, the emission layer may consist of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage.

[1221] According to a preferred embodiment of the present invention, the emission layer comprises a light-emitting compound of formula (X):

[1222]

[1223] wherein

[1224] Z1, Z2and Z3are the same as or different from each other, and are each independently selected from the group comprising a monocyclic to polycyclic aromatic hydrocarbon ring or monocyclic to polycyclic aromatic hetero ring;

[1225] Ar31and Ar32are the same as or selected different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring;

[1226] R31, R32and R33are the same as or different from each other, and are each independently selected from the group comprising hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring,

[1227] wherein one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, an alkyl silyl group having 1 to 30 carbon atoms, an aryl silyl group having 6 to 50 carbon atoms, an alkylamine group having 1 to 30 carbon atoms, an alkylarylamine group having 1 to 50 carbon atoms, an arylamine group having 6 to 50 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or a substituent to which two or more substituents selected from the group are linked, or adjacent substituents are bonded to each other to form an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, which is unsubstituted or substituted with the substituent; r31, r32and r33are each an integer from 0, 1, 2, 3 or 4, and when r31to r33are 2 or higher, substituents in the parenthesis are the same as or different from each other.

[1228] According to one embodiment, for formula (IX):

[1229] Z1, Z2and Z3are the same as or selected different from each other, and are each independently selected from the group comprising a monocyclic to bicyclic aromatic hydrocarbon ring, or a monocyclic to bicyclic aromatic hetero ring containing O, N or S;

[1230] Ar31and Ar32are the same as or selected different from, and are each independently selected from the group comprising an alkyl group having 1 to 10 carbon atoms, which is unsubstituted or substituted with an aryl group, an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with an aryl group, or a heteroaryl group having 2 to 30 carbon atoms;

[1231] R31, R32and R33are the same as or selected different from each other, and are each independently selected from the group comprising hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group,

[1232] or a substituted or unsubstituted heteroaryl group.

[1233] According to one embodiment, wherein for formula (IX):

[1234] Z1, Z2and Z3are the same as or selected different from each other, and are each independently selected from the group comprising a benzene ring or a thiophene ring;

[1235] Ar31and Ar32are the same as or selected different from each other, and are each independently selected from the group comprising phenyl group, a biphenyl group, a naphthyl group, a dimethyl fluorenyl group, a diphenyl fluorenyl group, a dibenzofuran group, or a dibenzothiophene group;

[1236] R31, R32and R33are the same as or selected different from each other, and are each independently selected from the group comprising hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. According to a preferred embodiment of the present invention, the emission layer comprises a light-emitting compound of formula (X) is selected from formulae (BD1) to (BD9):

[1237]

[1238]

[1239] According to a preferred embodiment of the present invention, the emission layer comprises an organic emitter host compound, wherein the organic emitter host compound comprises

[1240] - at least one condensed aromatic ring system consisting of 3 to 5 rings, and

[1241] - 3 to 7 aromatic or heteroaromatic rings, wherein one or more sub-groups of the aromatic and / or heteroaromatic rings may be condensed to form fused aromatic or heteroaromatic ring systems;

[1242] wherein the molecular weight Mw of the organic emitter host compound is in the range of > 400 and < 2000 g / mol.

[1243] According to a preferred embodiment of the present invention, the organic emitter host compound has the formula (XI)

[1244]

[1245] R47R46(XI), wherein

[1246] Ar41and Ar42are independently selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C3 to C24 heteroaryl;

[1247] L41and L42are independently selected from a direct bond or substituted or unsubstituted C6 to C24 arylene, substituted or unsubstituted C3 to C24 heteroarylene;

[1248] R41to R48are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C19 aryl, substituted or unsubstituted C3 to C12 heteroaryl;

[1249] wherein the substituents on Ar41, Ar42, L41, L42, R41to R48are independently selected from D, C6 to C10 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, halogen, F or CN.

[1250] According to a preferred embodiment of the present invention, the organic emitter host and / or compound of formula (XI) is selected from formulae (BH1) to (BH13):

[1251]

[1252]

[1253] According to a preferred embodiment of the present invention, the emission layer comprises a light-emitting dopant of formula (X) and an organic emitter host of formula (XI).

[1254] According to a preferred embodiment of the present invention, the organic semiconductor layer comprises a compound of Formula (I) and a compound of formula (IXa) or formula (IXb), the hole transport layer comprises a compound of formula (IXa) or formula (IXb), preferably the organic semiconductor layer and the hole transport layer comprise the same compound of formula (IXa) or formula (IXb) and the emission layer comprises a light-emitting dopant of formula (X) and an organic emitter host of formula (XI);

[1255] wherein the organic semiconductor layer is arranged between the anode layer and the hole transport layer, the hole transport layer is arranged between the organic semiconductor layer and the emission layer, and the emission layer is arranged between the hole transport layer and the cathode layer.

[1256] According to a preferred embodiment of the present invention, the organic semiconductor layer comprises a compound of Formula (I) and a compound of formula (IXa) or formula (IXb), the hole transport layer comprises a compound of formula (IXa) or formula (IXb), preferably the organic semiconductor layer and the hole transport layer comprise the same compound of formula (IXa) or formula (IXb) and the emission layer comprises a light-emitting dopant of formula (X) and an organic emitter host of formula (XI);

[1257] wherein the organic semiconductor layer is arranged between the anode layer and the hole transport layer, the hole transport layer is arranged between the organic semiconductor layer and the emission layer, and the emission layer is arranged between the hole transport layer and the cathode layer;

[1258] wherein the anode layer may comprise a first anode sub-layer comprising Ag or Au having a thickness of 100 to 150 nm, a second anode sub-layer comprising or consisting of a transparent conductive oxide having a thickness of 3 to 20 nm and a third anode sub-layer comprising or consisting of a transparent conductive oxide having a thickness of 3 to 20 nm, preferably the transparent conductive oxide is selected from ITO or IZO.

[1259] Hole blocking layer (HBL)

[1260] A hole blocking layer (HBL) may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL. When the EML comprises a phosphorescent dopant, the HBL may have also a triplet exciton blocking function.

[1261] The HBL may also be named auxiliary ETL or a-ETL.

[1262] When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and triazine derivatives.

[1263] The HBL may have a thickness in the range from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in driving voltage.

[1264] Electron transport layer (ETL)

[1265] The organic electronic device according to the present invention may further comprise an electron transport layer (ETL), wherein the electron transport layer is arranged between the anode layer and the cathode layer, preferably between the organic semiconductor layer and the cathode layer.

[1266] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a triazine compound.

[1267] In one embodiment, the electron transport layer may further comprise a dopant selected from an alkali organic complex, preferably LiQ.

[1268] The thickness of the ETL may be in the range from about 15 nm to about 50 nm, for example, in the range from about 20 nm to about 40 nm. When the thickness of the EIL is within this range, the ETL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage.

[1269] According to another embodiment of the present invention, the organic electronic device may further comprise a hole blocking layer and an electron transport layer, wherein the hole blocking layer and the electron transport layer comprise an azine compound. Preferably, the azine compound is a triazine compound.

[1270] Electron injection layer (EIL)

[1271] An optional EIL, which may facilitates injection of electrons from the cathode, may be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg which are known in the art. Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL.

[1272] The thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron- injecting properties, without a substantial penalty in driving voltage.

[1273] Cathode layer

[1274] The cathode layer is formed on the ETL or optional EIL. The cathode layer may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof. The cathode layer may have a low work function. For example, the cathode layer may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like. Alternatively, the cathode layer may be formed of a transparent conductive oxide, such as ITO or IZO.

[1275] The thickness of the cathode layer may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range from about 5 nm to about 50 nm, the cathode layer may be transparent or semitransparent even if formed from a metal or metal alloy.

[1276] It is to be understood that the cathode layer is not part of an electron injection layer or the electron transport layer.

[1277] Organic light-emitting diode (OLED)

[1278] The organic electronic device according to the invention may be an organic light-emitting device.

[1279] According to one aspect of the present invention, there is provided an organic lightemitting diode (OLED) comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising compound of Formula (I), a hole transport layer, an emission layer, an electron transport layer and a cathode layer.

[1280] According to another aspect of the present invention, there is provided an OLED comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising a compound of Formula (I), a hole transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer and a cathode layer.

[1281] According to another aspect of the present invention, there is provided an OLED comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising a compound of Formula (I), a hole transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode layer.

[1282] According to various embodiments of the present invention, there may be provided OLEDs layers arranged between the above mentioned layers, on the substrate or on the top layer.

[1283] Organic electronic device

[1284] The organic electronic device according to the invention may be a light emitting device, or a photovoltaic cell, and preferably a light emitting device.

[1285] According to another aspect of the present invention, there is provided a method of manufacturing an organic electronic device, the method using:

[1286] at least one deposition source, preferably two deposition sources and more preferred at least three deposition sources.

[1287] The methods for deposition that can be suitable comprise:

[1288] deposition via vacuum thermal evaporation;

[1289] deposition via solution processing, preferably the processing is selected from spincoating, printing, casting; and / or

[1290] slot-die coating.

[1291] According to various embodiments of the present invention, there is provided a method using:

[1292] a first deposition source to release the compound of Formula (I) according to the invention, and

[1293] a second deposition source to release the substantially covalent matrix compound; the method comprising the steps of forming the organic semiconductor layer; whereby for an organic light-emitting diode (OLED):

[1294] the organic semiconductor layer is formed by releasing the compound of Formula (I) according to the invention from the first deposition source and the substantially covalent matrix compound from the second deposition source. According to various embodiments of the present invention, the method may further include forming on the anode layer, at least one layer selected from the group consisting of forming a hole transport layer or forming a hole blocking layer, and an emission layer between the anode layer and the first electron transport layer.

[1295] According to various embodiments of the present invention, the method may further include the steps for forming an organic light-emitting diode (OLED), wherein

[1296] on a substrate an anode layer is formed,

[1297] on the anode layer an organic semiconductor layer comprising a compound of Formula (I) is formed,

[1298] on the organic semiconductor layer comprising a compound of Formula (I) a hole transport layer is formed,

[1299] on the hole transport layer an emission layer is formed,

[1300] on the emission layer an electron transport layer is formed, optionally a hole blocking layer is formed on the emission layer,

[1301] and finally a cathode layer is formed,

[1302] optional a hole blocking layer is formed in that order between the first anode layer and the emission layer,

[1303] optional an electron injection layer is formed between the electron transport layer and the cathode layer.

[1304] According to various embodiments, the OLED may have the following layer structure, wherein the layers having the following order:

[1305] anode layer, organic semiconductor layer comprising a compound of Formula (I) according to the invention, first hole transport layer, second hole transport layer, emission layer, optional hole blocking layer, electron transport layer, optional electron injection layer, and cathode layer.

[1306] According to another aspect of the invention, it is provided an electronic device comprising at least one organic light emitting device according to any embodiment described throughout this application, preferably, the electronic device comprises the organic light emitting diode in one of embodiments described throughout this application. More preferably, the electronic device is a display device. Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Reference will now be made in detail to the exemplary aspects.

[1307] Description of the Drawings

[1308] The aforementioned components, as well as the claimed components and the components to be used in accordance with the invention in the described embodiments, are not subject to any special exceptions with respect to their size, shape, material selection and technical concept such that the selection criteria known in the pertinent field can be applied without limitations.

[1309] Additional details, characteristics and advantages of the object of the invention are disclosed in the dependent claims and the following description of the respective figures which in an exemplary fashion show preferred embodiment according to the invention. Any embodiment does not necessarily represent the full scope of the invention, however, and reference is made therefore to the claims and herein for interpreting the scope of the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the present invention as claimed.

[1310] FIG. 1 is a schematic sectional view of an organic electronic device, according to an exemplary embodiment of the present invention;

[1311] FIG. 2 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention;

[1312] FIG. 3 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention.

[1313] FIG. 4 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention;

[1314] FIG. 5 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention.

[1315] FIG. 6 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention. FIG. 1 is a schematic sectional view of an organic electronic device 101, according to an exemplary embodiment of the present invention. The organic electronic device 101 includes a substrate (110), an anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), a photoactive layer (PAL) (151) and a cathode layer (190).

[1316] FIG. 2 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), an emission layer (EML) (150) and a cathode layer (190).

[1317] FIG. 3 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), a hole transport layer (HTL) (140), an emission layer (EML) (150), an electron transport layer (ETL) (160) and a cathode layer (190).

[1318] FIG. 4 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), an emission layer (EML) (150), a hole blocking layer (HBL) (155), an electron transport layer (ETL) (160), an optional electron injection layer (EIL) (180), and a cathode layer (190).

[1319] FIG. 5 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120) that comprises a first anode sub-layer (121) and a second anode sub-layer (122), a hole injection layer comprising a metal complex according to formula (I) (130), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), an emission layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160) and a cathode layer (190).

[1320] FIG. 6 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120) that comprises a first anode sub-layer (121), a second anode sub-layer (122) and a third anode sub-layer (123), a hole injection layer comprising a metal complex according to formula (I) (130), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), an emission layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160) and a cathode layer (190). The layers are disposed exactly in the order as mentioned before.

[1321] In the description above the method of manufacture an organic electronic device 101 of the present invention is for example started with a substrate (110) onto which an anode layer (120) is formed, on the anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), a photoactive layer (151) and a cathode electrode 190 are formed, exactly in that order or exactly the other way around.

[1322] In the description above the method of manufacture an OLED of the present invention is started with a substrate (110) onto which an anode layer (120) is formed, on the anode layer (120), a hole injection layer comprising a metal complex according to formula (I) (130), optional a hole transport layer (140), optional an electron blocking layer (145), an emission layer (150), optional a hole blocking layer (155), optional an electron transport layer (160), optional an electron injection layer (180), and a cathode electrode 190 are formed, exactly in that order or exactly the other way around.

[1323] The semiconductor layer comprising a metal complex according to formula (I) (130) can be a hole injection layer.

[1324] While not shown in Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5 and Fig. 6, a capping layer and / or a sealing layer may further be formed on the cathode electrodes 190, in order to seal the OLEDs 100. In addition, various other modifications may be applied thereto.

[1325] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with, reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention.

[1326] Calculated HOMO and LUMO

[1327] The energy the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and dipole moment (μ) of compounds of formula (I), and comparative compounds were calculated with the program package ORCA V5.0.3 (Max Planck Institute fur Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (F AccTs GmbH, Rolandstrasse 67, 50677 Koln, Germany). The LUMO energy levels and dipole moment of the molecular structures are determined by applying the hybrid functional B3LYP with a Def2-TZVP basis set and the Stuttgart / Dresden (SDD) effective core potential (ECP) for the metals from the optimized geometries obtained by applying the functional BP86 with a Def2-SVP basis set the Stuttgart / Dresden (SDD) effective core potential (ECP) for the metals. All the calculations were performed in the gas phase. If more than one conformation is viable, the conformation with the lowest total energy is selected. Depending on the metal cation different multiplicities may be applied. For the following metal cations the multiplicity is shown in brackets: Cu2+(doublet), Mn2+(sextet). The HOMO, LUMO and dipole moments values in Table 1 were calculated by this method unless noted otherwise.

[1328] General method for determining the sheet resistance of the hole injection layer

[1329] The sheet resistance of the hole injection, also named “2L-Rs”, is determined in Giga Ohm per square (GΩ / sq).

[1330] The sheet resistance Rs may be determined via the transfer length method. The measurement may be conducted by methods known in the art or as described in WO2022263524A1.

[1331] For the examples according to the invention and comparative examples in Table 3, the Rs for the hole injection layer (HIL) is determined as follows:

[1332] In a first step, a device comprising a hole transport layer and a hole injection layer is prepared, whereby the hole injection layer is deposited directly on the electrodes, and the hole transport layer is deposited directly on the hole injection layer.

[1333] In a second step, the sheet resistance Rs is determined for each device by using the transfer length method.

[1334] The higher the sheet resistance is, the lower is the current flow between adjacent pixels. Thereby, individual pixels in an electronic device can be addressed without adjacent pixels lighting up. Thereby, the so-called pixel crosstalk may be reduced.

[1335] The sheet resistance of the OLED, also named “OLED-Rs”, is determined in giga Ohm per square (GΩ / sq).

[1336] The sheet resistance Rs may be determined via the transfer length method. The measurement may be conducted by methods known in the art or as described in WO2022263524A1. For the examples according to the invention and comparative examples in Table 7, the OLED-Rs is determined as follows:

[1337] In a first step, the complete OLED as described in the examples and comparative examples is deposited.

[1338] In a second step, the sheet resistance Rs is determined for each device by using the transfer length method, while the cathode is not connected.

[1339] The higher the sheet resistance, the lower is the current flow between adjacent pixels. Thereby, individual pixels in an electronic device can be addressed without adjacent pixels lighting up. Thereby, the so-called pixel crosstalk may be reduced.

[1340] Glass transition temperature

[1341] The glass transition temperature (Tg) is measured under nitrogen and using a heating rate of 10 K per min in a Mettler Toledo DSC 822e differential scanning calorimeter as described in DIN EN ISO 11357, published in March 2010.

[1342] Melting point Imp)

[1343] Melting point (mp) temperatures were measured by DSC at heating rate 10 K / min, the reported values correspond the peak temperature for the observed melting endotherm on the DSC curve.

[1344] Thermogravimetric analysis

[1345] The term " TGA5%" denotes the temperature at which 5 % weight loss occurs during thermogravimetric analysis and is measured in °C.

[1346] The TGA5% value may be determined by heating a 9-11 mg sample in a thermogravimetric analyzer at a heating rate of 10 K / min in an open 100 μL aluminum pan, under a stream of nitrogen at a flow rate of 20 mL / min in the balance area and of 30 mL / min in the oven area.

[1347] The TGA5% value may provide an indirect measure of the volatility and / or decomposition temperature of a compound. In first approximation, the higher the TGA5% value the lower is the volatility of a compound and / or the higher the decomposition temperature. Rate onset temperature

[1348] The rate onset temperature (TRO) is determined by loading 100 mg compound into a VTE source. As VTE source a point source for organic materials may be used as supplied by Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com). The VTE source is heated at a constant rate of 15 K / min at a pressure of less than 10-5mbar and the temperature inside the source measured with a thermocouple. Evaporation of the compound is detected with a QCM detector which detects deposition of the compound on the quartz crystal of the detector. The deposition rate on the quartz crystal is measured in Angstrom per second. To determine the rate onset temperature, the deposition rate is plotted against the VTE source temperature. The rate onset is the temperature at which noticeable deposition on the QCM detector occurs. For accurate results, the VTE source is heated and cooled three time and only results from the second and third run are used to determine the rate onset temperature.

[1349] To achieve good control over the evaporation rate of an organic compound, the rate onset temperature may be in the range of 170 to 280 °C. If the rate onset temperature is below 170 °C the evaporation may be too rapid and therefore difficult to control. If the rate onset temperature is above 280 °C the evaporation rate may be too low which may result in low tact time and decomposition of the organic compound in VTE source may occur due to prolonged exposure to elevated temperatures.

[1350] The rate onset temperature is an indirect measure of the volatility of a compound. The higher the rate onset temperature the lower is the volatility of a compound.

[1351] Synthesis examples

[1352] General procedure:

[1353] The substituted pyrazolone derivates were prepared following reported procedure [for example see J. Heterocycl. Chem., 1984, 21(6), 1747-1752; Tetrahedron Lett., 2012, 53(32), 4206-4208; Coord. Chem. Rev., 2005, 249, 2909-2945; WO2024033322.

[1354] General procedure for the synthesis of the acyl-pyrazolone derivate:

[1355] 2 equivalents of calcium hydroxide were added to 1 equivalent of pyrazolone in 1,4-dioxane under a nitrogen atmosphere. The suspension was cooled using a water bath and 1 equivalent of acyl chloride were added portion wise and the mixture was stirred overnight. The mixture was cooled using an ice-bath followed by the addition of 2N hydrochloric acid. The resulting suspension was filtered and the crude product was washed with water, dried in vacuum and further purified by sublimation to obtain product in quantitative yield as a pale yellow solid.

[1356] General procedure for the synthesis of the metal zinc(II) complexes:

[1357] 2 equivalents of acyl pyrazolone were dissolved in ethanol and 1 equivalent of manganese(II) acetate tetrahydrate was added. The resulting mixture was stirred overnight at room temperature. Then the resulting solution was cooled with an ice-bath and a precipitate formed. The precipitate was then filtered, washed with ethanol and hexane and then dried in vacuum to obtain the desired product in quantitative yield as a yellow powder. The final product was further purified by sublimation.

[1358] General procedure for fabrication of OLEDs

[1359] For inventive examples and comparative examples in Table 3 a glass substrate with an anode layer comprising a first anode sub-layer of 120 nm Ag, a second anode sub-layer of 8 nm ITO and a third anode sub-layer of 10 nm ITO was cut to a size of 25 mm x 25 mm x 0.7 mm, ultrasonically washed with water for 60 minutes and then with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment to prepare the anode layer. The plasma treatment was performed in an atmosphere comprising 98.4 vol.-% nitrogen and 1.6 vol.-% oxygen.

[1360] Then, 4 vol% of a metal complex, which may be the compound of Formula (I) or a comparative compound, and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine ([1607480-22-7]) as a matrix compound were co-deposited in vacuum on the anode layer, to form a hole injection layer (HIL) having a thickness of 10 nm. The composition of the HIL can be seen in Table 3.

[1361] Then, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine ([1607480-22-7]) was vacuum deposited on the HIL, to form a HTL having a thickness of 128 nm. The compound that forms the HTL is selected the same as the matrix compound in the HIL.

[1362] Then N, N-di([ 1, 1 '-biphenyl]-4-yl)-3 '-(9H-carbazol-9-yl)-[ 1, 1 '-biphenyl]-4-amine ([1464822-27-2]) was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm. Then the emission layer (EML) having a thickness of 20 nm was formed on the EBL by co-depositing 99 vol.-% 7-(phenyl-d5)-l-(10-(phenyl-d5)anthracen-9-yl)dibenzo[b,d]furan ([2457172-82-4]) as EML host and 1 vol.-% 5H,9H -[l]Benzothieno[2',3':5,6][l,4]azaborino[2,3,4-kl ]phenazaborine, 2,7,1 l-tris(l,l-dimethylethyl)-5,9-bis[4-(l,l-dimethylethyl)phenyl] ([2482607-57-6]) as blue dopant.

[1363] Then a hole blocking layer (HBL) having a thickness of 5 nm was formed on the EML by depositing 4-([l,l'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[l,l'-biphenyl]-4-yl)-2-phenylpyrimidine ([1955546-40-3]).

[1364] Then the electron transport layer (ETL) having a thickness of 31 nm was formed on the hole blocking layer by vacuum depositing 50 wt.-% 6,6'-(naphthalene-l,2-diylbis(4,l-phenylene))bis(2,4-diphenyl-l,3,5-triazine) ([2244287-14-5]) and 50 wt.-% of LiQ (8-Hydroxyquinolinato)lithium; ([25387-93-3] or [850918-68-2]).

[1365] Then an electron injection layer (EIL) was formed on the electron transport layer by vacuum depositing a layer of 1.3 nm Yb.

[1366] Then Ag:Mg (90:10 vol.-%) was evaporated at a rate of 0.01 to 1 Å / s at 10-7mbar to form a cathode layer with a thickness of 13 nm on the EIL.

[1367] Then, N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine ([1242056-42-3]) was deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[1368] To assess the performance of the inventive examples compared to the prior art, the current efficiency is measured at 20°C. The current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between 0V and 10V. Likewise, the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd / m2using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) for each of the voltage values. The cd / A efficiency at 15 mA / cm2is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[1369] In bottom emission devices, the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE). The light is emitted through the anode layer. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA / cm2. In top emission devices, the emission is forward directed through the cathode layer, non-Lambertian and also highly dependent on the mirco-cavity. Therefore, the efficiency EQE will be higher compared to bottom emission devices. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA / cm2.

[1370] Lifetime LT of the device is measured at ambient conditions (20°C) and 20 mA / cm2, using a Keithley 2400 source meter, and recorded in hours.

[1371] The brightness of the device is measured using a calibrated photo diode. The lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value.

[1372] To determine the voltage stability over time U(100h)-(lh), a current density of at 20 mA / cm2was applied to the device. The operating voltage was measured after 1 hour and after 100 hours, followed by calculation of the voltage stability for the time period of 1 hour to 100 hours. A low value for U(100h)-(lh) denotes a low increase in operating voltage over time and thereby improved voltage stability.

[1373] Technical Effect of the invention

[1374] Data of inventive and comparative examples are given in Table 1 below. With respect to Table 1, the comparative compounds CC1 to CC8 exhibit values of the LUMO energy level in the range of -5.18 eV to -4.24 eV.

[1375] The compounds of formula (I) depicted in Table 1 exhibit a larger value of the LUMO energy level in the range of -3.74 eV to -1.81 eV compared to CC1 to CC8.

[1376] A larger value of the LUMO energy level may be beneficial for increasing the sheet resistance of an organic semiconductor layer and / or an organic electroluminescent device. Thereby, the cross-talk between two pixels in a display may be decreased, and the color purity in a display device or resolution in a display may be improved.

[1377] The comparative compounds CC1 to CC8 exhibit an Egap (energy difference between LUMO energy level and HOMO energy level) in the range of 2.02 eV to 2.46 eV.

[1378] The compounds of formula (I) in Table 1 exhibit a larger Egap in the range of 3.20 eV to 4.57 eV compared to CC1 to CC9.

[1379] A larger Egap may lower the absorption of the visible light in e-g- an organic light-emitting device which may increase the current efficiency and / or the external quantum efficiency. With respect to Table 2, the comparative compound CC1 to CC5 exhibits a melting point Tm in the range of 265 to 299°C, a rate onset temperature TRO in the range of 141 to 246°C, a glass transition temperature Tg up to 126°C, and a TGA5% in the range of 179°C to 219°C.

[1380] The compounds of formula (I) depicted in Table 2 exhibit a high melting point Tm in the range of 272 to 367°C.

[1381] The compounds of formula (I) depicted in Table 2 exhibit a high rate onset temperature TRO in the range of 226 to 266°C.

[1382] The compounds of formula (I) depicted in Table 2 exhibit a higher glass transition temperature Tg in the range of 137 to 170°C compared to CC1 to CC5.

[1383] The compounds of formula (I) depicted in Table 2 exhibit a high TGA5% in the range of 339°C to 391°C.

[1384] A high melting may be beneficial for processing stability, i.e. avoiding decomposition and reduction of risk of clogging of nozzles if linear source systems are utilized.

[1385] A high rate onset temperature may be desirable for good control of the evaporation rate in mass production of organic electronic devices.

[1386] A high glass transition temperature may be beneficial for increased temperature stability during bake-out processes which are necessary in mass production. Furthermore, a high glass transition temperature may increase the stability of an organic electronic device in particular an organic light-emitting device

[1387] A high TGA5% may be desirable for improved thermal stability.

[1388] In Table 3, the setup and data are shown for an organic electroluminescent device comprising an organic semiconductor layer comprising a compound of formula (I) or a comparative compound.

[1389] In comparative example 1, the organic semiconductor layer comprises 4 vol% of comparative compound CC1 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. As can be seen in Table 3, the operating voltage is 3.44 V, the external quantum efficiency (Qeff or EQE) is 22.3%, the current efficiency (Ceff / CIE-y) is 232 cd / A, the lifetime LT97 is 95 h, and the voltage rise over time U(100h) -U(lh) is 0.04 V. In addition, the sheet resistance OLED-Rs and 2L-Rs are 101 GΩ / sq or 33 GΩ / sq, respectively.

[1390] In inventive example 1, the organic semiconductor layer comprises 4 vol% of a metal complex of formula (I) A13 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. As can be seen in Table 3, the operating voltage is 3.49 V, the external quantum efficiency (Qeff or EQE) is 22.2%, the current efficiency (Ceff / CIE-y) is 232 cd / A, the lifetime LT97 is improved 98 h compared to comparative example 1, and the voltage rise over time U(100h) -U(lh) is 0.06 V. In addition, the sheet resistance OLED-Rs and 2L-Rs are improved to 3580 GΩ / sq or 703 GΩ / sq, respectively compared to comparative example le.

[1391] In inventive example 2, the organic semiconductor layer comprises 4 vol% of a metal complex of formula (I) A6 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. As can be seen in Table 3, the operating voltage is 3.60 V, the external quantum efficiency (Qeff or EQE) is 22.3%, the current efficiency (Ceff / CIE-y) is 231 cd / A, the lifetime LT97 is improved to 116 h compared to comparative example 1, and the voltage rise over time U(100h) -U(lh) is -0.02 V. In addition, the sheet resistance OLED-Rs and 2L-Rs are improved to 4482 GΩ / sq or 1262 GΩ / sq, respectively compared to comparative example 1.

[1392] In inventive example 4, the organic semiconductor layer comprises 4 vol% of a metal complex of formula (I) A4 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. As can be seen in Table 3, the operating voltage is 3.47 V, the external quantum efficiency (Qeff or EQE) is 22.3%, the current efficiency (Ceff / CIE-y) is 231 cd / A, the lifetime LT97 is improved to 114 h compared to comparative example 1, and the voltage rise over time U(100h) -U(lh) is 0.4 V. In addition, the sheet resistance OLED-Rs and 2L-Rs are improved to 1708 GΩ / sq or 224 GΩ / sq, respectively compared to comparative example 1.

[1393] In inventive example 4, the organic semiconductor layer comprises 4 vol% of a metal complex of formula (I) A9 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. As can be seen in Table 3, the operating voltage is 3.44 V, the external quantum efficiency (Qeff or EQE) is 22.2%, the current efficiency (Ceff / CIE-y) is 232 cd / A, the lifetime LT97 is improved to 113 h compared to comparative example 1, and the voltage rise over time U(100h) -U(lh) is 0.03 V. In addition, the sheet resistance 2L-Rs is improved to 570 GΩ / sq, respectively compared to comparative example 1.

[1394] In inventive example 5, the organic semiconductor layer comprises 4 vol% of a metal complex of formula (I) A35 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine. The sheet resistance OLED-Rs and 2L-Rs are improved to 5005 GΩ / sq or 1724 GΩ / sq, respectively compared to comparative example 1. In summary, a substantial improvement of the sheet resistance have been obtained without detrimental effect on the operating voltage, voltage rise over time, lifetime, current efficiency and / or external quantum efficiency (Qeff or EQE).

[1395] A low operating voltage may be important for a lower power consumption of organic electronic devices, in particular mobile devices.

[1396] A long lifetime may result in improved long-term stability of electronic devices.

[1397] A low voltage rise over time may result in improved long-term stability of electronic devices.

[1398] A high efficiency may be beneficial for low power consumption of organic electronic devices, in particular in mobile devices.

[1399] An improved sheet resistance may result in improved pixel crosstalk. Thereby, the color purity in a display device or resolution in a display may be improved. Table 1: LUMO energy level, Egap (Difference between HOMO energy level and LUMO energy level), and dipole moment of compounds of formula (I) and comparative compounds

[1400] LUMO EGap Dipole Name Structure

[1401] [eV] [eV] Moment [D] CC1 Cu

[1402] oZ xo

[1403] / ==A k X

[1404] N / ^ / XCF3 -4.69 2.09 0.01 N=\

[1405] L CF3J 2

[1406] CC2 -4.24 2.02 0.00

[1407] 2

[1408] Cu

[1409] r F3C \ O O "i

[1410] ==:co

[1411] < \ 1111

[1412] N^^l^^ oCF

[1413] CC33

[1414] = °z -5.07 2.14 0.24

[1415] F CN

[1416] 3CY^-CF3

[1417] \ O

[1418] z

[1419] i— F3JC _ i2

[1420]

[1421] Cu

[1422] F3V0P

[1423] CC4 O~N / S^'CF3-4.73 2.22 0.63

[1424] _F3C^

[1425] 2

[1426] CC5 Cu

[1427] <> AAF3

[1428] -5.18 2.46 0.01 F3CA~Z^CF;

[1429] 2

[1430] CC6 Cu

[1431] F3°\ _ Q \>

[1432] -4.51 2.31 1.44

[1433] L CF3d-l2

[1434]

[1435] CC7 Cu

[1436] F3CX _ 0

[1437] NC'-^ V / Kz\ / VCF3-5.15 2.26 1.13

[1438] N J J T

[1439] F3C Y^CN

[1440] CF3

[1441] 2

[1442] CC8 Cu

[1443] r Fh3tC< o / \ o 1

[1444] -4.99 2.42 0.22

[1445] CF3

[1446] 2

[1447] Al Zn

[1448] F\ / ( / \ F

[1449] -2.68 4.18 2.07

[1450] 2

[1451] F

[1452] A2 Zn

[1453] V / O' \ F

[1454] -2.74 4.04 2.63

[1455] 2

[1456] F

[1457]

[1458] A4Zn

[1459] F\ F Q \

[1460] -2.61 4.05 3.40

[1461] 2

[1462] F

[1463] A5 Zn

[1464] F\ _, F Q \

[1465] -3.01 3.89 0.74F^NtO9:FCF3_

[1466] 2

[1467] CF3

[1468] A6 11

[1469] -2.91 3.94 1.40

[1470] 2

[1471] - / N \. ^

[1472] A7 Z \

[1473] Zn° /

[1474] 4 q —

[1475] ' ( w - -3.65 3.48 4.35 O

[1476] w

[1477] 11 2

[1478] CF3

[1479]

[1480] A8 Zn

[1481] F\ _ F < / \>

[1482] -3.34 3.76 2.69F^Ni6?CF3_

[1483] 2

[1484] CF3

[1485] A9 Zn

[1486] F\ F ( / \

[1487] -2.98 3.93 0.72 I J 2

[1488] F

[1489] A10 Zn

[1490] F\ F Q \

[1491] -3.16 4.09 0.74

[1492] 1 '# ■% ' J 2

[1493] F

[1494] A11 Zn

[1495] FV / <5 0 F

[1496] -2.59 4.18 0.12

[1497] 2

[1498] F

[1499]

[1500] A12Zn

[1501] FV / < / \ F

[1502] -2.66 4.03 1.26 1 ) 2

[1503] F

[1504] A13 zn

[1505] F\ F j \

[1506] -2.66 3.98 0.64 1 1 2

[1507] F

[1508] A14 Zn

[1509] V / 0

[1510] -2.54 4.02 1.38

[1511] 2

[1512] F

[1513] A15 Zn

[1514] F\ _, F Q \

[1515] -2.93 3.88 2.43

[1516] 2

[1517] CF3

[1518]

[1519] A16 Zn

[1520] FF\ _? ( / \

[1521] ^ ^VCF3_ -2.83 3.93 0.89

[1522] CF 2

[1523] A17 Zn3

[1524] F\ _ F Q \

[1525] -3.58 3.46 6.39 1 W v

[1526] A18 Zn CF3

[1527] 18

[1528] F\ _ F Q \

[1529] -3.26 3.75 4.71F^Ni6?CF3_

[1530] 2

[1531] A19 r Zn CF3"1

[1532] w ° / 0

[1533] -2.91 3.91 2.58 1 W g J 2

[1534] F

[1535]

[1536] A20Zn

[1537] F\ F Q \

[1538] -3.08 4.08 2.61

[1539] 1 1 2

[1540] F

[1541] A21Zn

[1542] F\ / Q \ F

[1543] -2.83 4.18 3.97

[1544] 2

[1545] F

[1546] A22Zn

[1547] F\ / Q \ F

[1548] -2.88 4.05 4.52

[1549] 2

[1550] F

[1551] A23Zn

[1552] -2.88 4.00 3.69

[1553] 2

[1554] F

[1555]

[1556] A24Zn

[1557] -2.75 4.07 5.48

[1558] 2

[1559] F

[1560] A25 Zn

[1561] V / 0

[1562] -3.39 3.78 1.56

[1563] l“w: J 2

[1564] F

[1565] A26Znn

[1566] f\ / f< / \

[1567] -3.06 4.04 1.37 / 3XNi< VF_

[1568] 2

[1569] F

[1570] A27 Zn

[1571] F\ _? ( / \>

[1572] -3.13 3.92 2.02F3C>rN^ p:FCF3_

[1573] 2

[1574] CF3

[1575]

[1576] A28 Zn

[1577] F\ _? ( / \

[1578] -3.03 3.97 3.35F3c^ ^VcF3_

[1579] 2

[1580] CF3

[1581] A29 Zn

[1582] F\ _ F Q \

[1583] -3.74 3.54 2.50

[1584] 2

[1585] CF3

[1586] A30 Zn

[1587] F\ _ F Q \

[1588] -3.45 3.80 1.00F3C^Ni6?CF3_

[1589] 2

[1590] CF3

[1591] A31 r Zn "1

[1592] w0

[1593] -3.11 3.95 1.67 r# ^v:,. J 2

[1594] F

[1595]

[1596] A32Zn

[1597] -3.27 4.11 1.47

[1598] 2

[1599] F

[1600] A33Zn

[1601] F\ / Q \ F

[1602] -2.99 4.15 7.12

[1603] 2

[1604] F

[1605] A34Zn

[1606] F\ / Q \ F

[1607] -3.03 4.03 7.65

[1608] 2

[1609] F

[1610] A35Zn

[1611] -3.02 3.99 6.85

[1612] 2

[1613] F

[1614]

[1615] A36 Zn

[1616] F\ _? < / \>

[1617] -3.25 3.92 4.99

[1618] 2

[1619] CF3

[1620] A37

[1621] -3.16 3.96 6.50

[1622] 2

[1623] A38 r- Zn _,

[1624] -3.39 4.11 4.43 I,cJ 2

[1625] F

[1626] A39Zn11

[1627] <n

[1628] o

[1629] F=CV / < / \ F z \05- \ -2.95 4.19 5.63 ^\ c

[1630] / _ _ N \O=2

[1631] F

[1632]

[1633] G V

[1634] z

[1635] o

[1636] z

[1637] 1 _ 1 A40Zn

[1638] F=5 / < / \ F

[1639] -3.00 4.05 5.95

[1640] 2

[1641] F

[1642] A41Zn

[1643] F=C> F < / \

[1644] -2.99 4.01 5.30 1 $ Wr1 2

[1645] F

[1646] A42Zn

[1647] F=cv / 0- 0

[1648] -3.24 3.92 3.58

[1649] 2

[1650] CF3

[1651] A43zn

[1652] F=% F °0

[1653] -3.13 3.99 4.97;^ kV CFF3. 2

[1654] 3

[1655]

[1656] A44 Zn

[1657] F\ F Q \

[1658] -3.37 4.15 2.95

[1659] - 2

[1660] F

[1661] A45 Zn

[1662] ■F=C> F j, \

[1663] -3.03 3.98 3.27

[1664] CF3— z

[1665] A46 Zn

[1666] rf f< A i

[1667] -3.46 3.79 0.84

[1668] CF32

[1669] — / \

[1670] A47 / \

[1671] -2.70 3.98 1.99 o w

[1672] - 2

[1673]

[1674] A48 Zn

[1675] F\ F ( / \

[1676] -2.62 3.97 0.36

[1677] 2

[1678] A49 r zn n

[1679] W °0-2.83 4.00 4.02

[1680] N\ ^^CF3- 2

[1681] A50

[1682] -2.97 3.99 7.17

[1683] 2

[1684] A51 Zn

[1685] F\ _ F Q \ i i

[1686] co -3.84 3.55 1.46 o

[1687] J 2

[1688] CF3

[1689]

[1690] / - \

[1691] z

[1692] o

[1693] z

[1694] 1 _ 1 A52 Zn

[1695] F\ _? < / \>

[1696] -3.56 3.81 2.64Nc^Nt6?cF3_

[1697] 2

[1698] CF3

[1699] A53 r zn n

[1700] W °0

[1701] -3.23 3.95 4.78 1. J 2

[1702] F

[1703] A54Znn

[1704] [F3V / F° °

[1705] -3.49 3.81 1.16

[1706] 2

[1707] F

[1708] A55 Zn

[1709] FA / f° \°

[1710] -2.93 4.03 5.61

[1711] 1 2

[1712]

[1713] A56 Zn

[1714] FA F J \ -3.83 3.57 1.21 & W: 2

[1715] CF3

[1716] A57 Zn

[1717] F=cv / < / \

[1718] -3.55 3.83 1.41

[1719] 2

[1720] CF3

[1721] A58 Zn

[1722] F3V / ° °

[1723] -3.21 3.97 3.28 - 2

[1724] F

[1725] A59 Zn

[1726] -3.87 3.58 1.57

[1727] CF3J,

[1728]

[1729] A60 Zn

[1730] F\ F o' \

[1731] -3.54 3.84 0.71

[1732] CF3J

[1733] 2

[1734] Bl Zn

[1735] F\ F Q \

[1736] -3.10 4.02 2.56

[1737] 2

[1738] F

[1739] B2 Zn

[1740] -3.01 4.03 1.50

[1741] 2

[1742] F

[1743] B3 Zn

[1744] -3.21 4.06 4.19

[1745] 2

[1746] F

[1747]

[1748] B4Zn

[1749] -3.33 4.05 7.16

[1750] _ " M “ p Ui 2n X 1 r — 2

[1751] F

[1752] B5Zn

[1753] F=C> F d \

[1754] -2.87 4.06 7.03 _ - 2

[1755] F

[1756] B6Zn

[1757] F3V / F° \°

[1758] -3.17 4.06 2.99

[1759] 2

[1760] F

[1761] B7Zn

[1762] F=5 / J \

[1763] -3.31 4.08 5.69

[1764] _ r p Ui 2n 1 r _ 2

[1765] F

[1766]

[1767] B8Znn

[1768] F\ / F® \°

[1769] -3.28 3.74 3.36 1 J 2

[1770] F

[1771] B9 Zn

[1772] W °0

[1773] -2.93 4.01 0.93rA A V.

[1774] 2

[1775] B10

[1776] -2.54 4.10 6.37 F3C— / ~V

[1777] \=zN> J I i

[1778] LF^FNA J 2

[1779] B11Zn_,

[1780] -2.91 4.03 8.60

[1781] 2

[1782] F

[1783]

[1784] B12 Zn

[1785] F=CV / 0 / \

[1786] -2.66 4.10 7.92 1 J 2

[1787] Cl r zn n

[1788] Fw °0-2.40 4.09 4.36 LFM NA J 2

[1789] C2 Zn

[1790] -2.32 4.08 2.27

[1791] . - 2

[1792] C3 Zn _,

[1793] F\ F ( / \

[1794] -3.21 3.72 5.30 1 2

[1795] F

[1796]

[1797] C4 Zn

[1798] V / F< / °

[1799] -2.85 4.00 2.86

[1800] 2

[1801] F

[1802] C5 Zn

[1803] -2.74 4.03 9.57. “^ -■b6ar.

[1804] 2

[1805] C6 Zn

[1806] F\ _ F < / \

[1807] -3.50 3.79 2.20 I J 2

[1808] F

[1809] C7 Zn

[1810] f\ / f< /

[1811] -3.20 4.02 4.41; XNi< VF_

[1812] 2

[1813] F

[1814]

[1815] D1 Zn

[1816] -2.25 4.34 7.82

[1817] 1 2

[1818] D2 Zn

[1819] -2.02 4.48 4.97

[1820] 2

[1821] D3 Zn

[1822] -2.16 4.34 5.69

[1823] 1 1 2

[1824] D4 Zn

[1825] F\ / Q \ |

[1826] -1.94 4.46 2.94. J 2

[1827]

[1828] D5 Zn

[1829] F\ / o 0 CF3

[1830] -2.41 4.34 10.05

[1831] 2

[1832] D6 Zn

[1833] F\, F Q \ |

[1834] -2.24 4.42 7.09

[1835] 2

[1836] D7 Zn

[1837] F\ F oZ0 CF3

[1838] -2.67 4.21 13.05

[1839] 2

[1840] D8 Zn

[1841] -2.64 4.15 9.94. "^ -■br56. 2

[1842]

[1843] D9 Zn

[1844] PFsCC\ F o / \ 0 CF3

[1845] -2.54 4.34 11.24 ihX d - 2

[1846] D10 Zn

[1847] p3V / F° ° 1 -2.42 4.35 8.32

[1848] - 2

[1849] D11 Zn

[1850] F\ F / \

[1851] -2.83 4.18 0.72F'^1-N\^CF3

[1852] _ \NYH3J2

[1853] D12 Zn

[1854] F\ F / \

[1855] -2.74 4.17 1.25

[1856] _ F' VNYH3J2

[1857]

[1858] D13Zn

[1859] F\ F Q \ -3.35 4.30 1.99

[1860] LhFCF3J 2

[1861] D14 Zn

[1862] W °0-3.26 4.30 3.95

[1863] LrF^FX CF3cr' J 2

[1864] D15 Zn

[1865] W °0-1.90 4.57 5.28

[1866] rF ^n3-1 2

[1867] D16Zn

[1868] F\ F Q \ -1.81 4.56 3.29

[1869] rF ^FIs J 2

[1870]

[1871] D17Zn

[1872] \ / F* \°

[1873] -3.19 3.85 1.89 ) 2

[1874] F

[1875] D18 Zn

[1876] W °0

[1877] -3.10 3.86 3.87 2

[1878] F

[1879] D19 Zn

[1880] \ c / \

[1881] -3.20 3.68 1.37 2

[1882] F

[1883]

[1884] D20

[1885] -3.49 4.32 0.16

[1886] 2

[1887] D21 r Zn -

[1888] Fy__ / F® \ -3.62 4.31 2.65NC^ ^CF3

[1889] LF > CF3J2

[1890] D22 Zn -F\ F Q \>

[1891] -3.53 4.33 0.29

[1892] - X 1- F XCF3"- 2

[1893] D23 r Zn -

[1894] \ / F\°

[1895] 11 -3.62 4.36 1.53 co

[1896] L- |-3UFCF3 co o

[1897] O -12

[1898] ( — L1-

[1899]

[1900] O

[1901] / —l \\ r

[1902] z

[1903] co o

[1904] 11 Table 2: Thermal properties of the compounds of formula (I) and comparative compounds

[1905] Name Compound Tg / °C Mp / Rate TGA5%

[1906] °C Onset /

[1907] °C

[1908] CC1 not. 265 146 179 o obs.

[1909] z

[1910] " Z \ o-—

[1911] c / \ z

[1912] CC2 ° /

[1913] o not. 299 160 194 “ 11 _ _ obs.

[1914] CC3 not. 293 171 219 obs.

[1915]

[1916] u?

[1917] o11

[1918] A /

[1919] A( / LA=

[1920] o

[1921] Vo= / °°=

[1922] \ O—

[1923] J /

[1924] A 1 _ ± _ 1 CC4 Cu not. 288 141 188 obs.

[1925] rFV J> \ 1

[1926] C 'X V / / — N -M / - CCFF3

[1927] L. F, C^ 'N=\ —I2

[1928] CC5 Cu 126 not obs. 162 207

[1929] 0 \>

[1930] Vcp3

[1931] F3C^ N<CF3

[1932] -12

[1933] A13Zn153 326 246 381

[1934] F\ F J \

[1935] 1 W 1 2

[1936] F

[1937] A4 zn 140 292 200 373

[1938] F\ F ( / \

[1939] 2

[1940] F

[1941]

[1942] A6 Zn 135 281 219 357F\ _? Q \>

[1943] F^Ni67CF3_

[1944] 2

[1945] CF3

[1946] A9 Zn n.d. 326 222 371

[1947] F\ F Q \

[1948] [ ] 2

[1949] F

[1950] A35 r- Zn 170 367 266 382

[1951] w ° / °

[1952] ;c^ i67; _

[1953] 2

[1954] F

[1955]

[1956] Table 3: Setup, Performance and stability of organic electroluminescent devices and comparative examples

[1957] Example p-HIL Voltage QEff CEff / CIE-y LT97 Voltage rise OLED- 2L-Rs [V] [%] [cd / A] 20 mA / cm220 mA / cm2Rs [GQ / sq]

[1958] [h] (l-100h) [V] [GQ / sq] Comparative example 1 CC1 3.44 22.3 232 95 0.04 101 33 Inventive example 1 A13 3.49 22.2 232 98 0.06 3580 703 Inventive example 2 A6 3.60 22.3 231 116 -0.02 4482 1262 Inventive example 3 A4 3.47 22.3 231 114 0.04 1708 224 Inventive example 4 A9 3.44 22.2 232 113 0.03 No data 270 Inventive example 5 A35 ___ — — — — 5005 1742

[1959]

[1960] The particular combinations of elements and features in the above detailed embodiments are exemplary only; the interchanging and substitution of these teachings with other teachings in this and the patents / applications incorporated by reference are also expressly contemplated. As those skilled in the art will recognize, variations, modifications, and other implementations of what is described herein can occur to those of ordinary skill in the art without departing from the spirit and the scope of the invention as claimed. Accordingly, the foregoing description is by way of example only and is not intended as limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the indefinite article "a" or "an" does not exclude a plurality. The mere fact that certain measures are recited in mutually different dependent claims does not indicate that a combination of these measured cannot be used to advantage. The invention's scope is defined in the following claims and the equivalents thereto. Furthermore, reference signs used in the description and claims do not limit the scope of the invention as claimed.

Claims

ND 420661. A compound of Formula (I):ZnL2(AL)m(I)whereby Zn is in the oxidation state Zn(II),L is a ligand of formula (II)wherein R1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C2o heteroaryl;wherein R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C2o heteroaryl;wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2to C2o heteroaryl, CN, orNO2;wherein L comprises at least one aryl or heteroaryl comprising at least three F groups directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl;wherein AL is an ancillary ligand which coordinates to the metal M;wherein m is an integer selected from 0 to 2;2. The compound of claim 1, whereby a ligand of formula (II) according to the following table is excluded:

3. The compound of the claim 1 or 2, whereby in Ligand L at least one of R1, R2, and R3is selected from an aryl or heteroaryl comprising at least three F groups directly bonded directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl.

4. The compound of any of the claims 1 to 3, whereby in Ligand L at least one of R1and R2is selected from an aryl or heteroaryl comprising at least three F group directly bonded to a sp2-hybridized carbon atom of the ring of the aryl or of the heteroaryl.

5. The compound of any of the claims 1 to 4, whereby the molecular mass of L is selected in the range of < 600 Da and > 176 Da6. The compound of any of the claims 1 to 5, wherebyR1is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl,wherein the one or more substituents on R1are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl,wherein the one or more substituents on R2are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2;herein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, orNO2;R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2,wherein the one or more substituents on R3are independently selected from D, F, CN, NO2, unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

7. The compound of any of the claims 1 to 6, wherein the substituted or unsubstituted Ce to C19 aryl, and the substituted or unsubstituted C2 to C20 heteroaryl is selected from formula (III), and (IV)whereinX1is selected from N or CR4;X2is selected from N or CR5;X3is selected from N or CR6;X4is selected from N or CR7;X5is selected from N or CR8;whereinX1'is selected from N or CR9;X2'is selected from N or CR10;X3'is selected from N or CR11;X4'is selected from N or CR12;X5'is selected from N or CR13;wherein R4, R5, R6’R7, R8, R9, R10, R11, R12, and R13, if present, are independently selected from H, D, substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, F, CN, or NO2.

8. The compound of any of the claims 1 to 7, wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, R1is selected from formula (III) and R2is selected from formula (IV), CH3, CF3, and CF2H.

9. The compound of any of the claims 1 to 8, wherein R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, CN, or NO2, R1is selected from formula (III) and R2is selected from formula (IV).

10. The compound of any of the claims 1 to 9, whereby R3is selected from CH3, CF3, and CF2H, R1is selected from formula (III) and R2is selected from formula (IV), CH3, CF3, and CF2H.

11. The compound of any of the claims 1 to 10, whereby R1is selected from substituted or unsubstituted Ce to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl; R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD,CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

12. The compound of any of the claims 1 to 11, whereby R1is selected from formula (III); R2is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R3is selected from substituted or unsubstituted Ci to C12 alkyl, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated Ci to C12 alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

13. The compound of any of the claims 1 to 12, whereby R1is selected from formula (III) and R2is selected from CH3, CF3, and CF2H, and R3is selected from CH3, CF3, and CF2H, CN,.

14. The compound of any of the claim 1 to 13, wherein at least one of R1, R2, R3is selected from formula (III) and wherein at least three of X1, X2, X3, X4, and X5are selected from CF.

15. The compound of any of the claims 1 to 14, wherein R3is selected from CH3, CF3, and CF2H.

16. The compound of any of the claims 1 to 15, wherein at least one of R1, R2, and R3is independently selected from Fl to F25:

17. The compound of any of the claims 1 to 16, selected from formulae Al to A60, Bl to B12, Cl to C7, DI to D23:

18. The compound of any of the claims 1 to 16, selected from formulae A1, A2, A4 to A60, B1 to B12, C1 to C7, D1 to D23:

19. Use of a compound of formula (I) of any of the claims 1 to 18 in an organic device, especially an organic electroluminescent device.

20. Use of a compound of formula (I) of any of the claims 1 to 19 as a p-dopant.

21. An organic semiconductor layer, whereby the organic semiconductor layer comprises a compound of formula (I) of any of the preceding claims 1 to 18.

22. An organic electronic device comprising an anode layer, a cathode layer, and an organic semiconductor layer according to claim 21, preferably the organic semiconductor layer is arranged between the anode layer and the cathode layer.

23. The organic electronic device according to claim 22, wherein the organic semiconductor layer is arranged adjacent to the anode layer, preferably the organic semiconductor layer is arranged in direct contact with the anode layer.

24. The organic electronic device of claim 22 or 23, whereby at least one organic semiconductor layer that is the organic semiconductor layer according to claim 14 is a hole injection layer.

25. The organic electronic device according to any of the claims 22 to 24, wherein the organic electronic device is an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, thin film transistor, a battery, a display device, an organic photovoltaic cell (OPV), or an organic photodetector.

26. A display device comprising an organic electronic device according to any of the claims 22 to 25.

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