Metal complexes, semiconductor layers containing metal complexes, and organic electronic devices

Abstract

The present invention relates to a compound of formula (I) and an organic electronic device comprising a semiconductor layer containing a compound of formula (I).

Description

Technical Field

[0001] 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. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are self-emissive electronic devices that possess wide viewing angles, excellent contrast ratios, fast response times, high brightness, superior operating voltage characteristics, and excellent color reproduction. A typical OLED comprises an anode layer, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode layer, which are sequentially stacked on a substrate. In this regard, the HIL, HTL, EML, and ETL are thin films formed from organic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode move to the EML via the HIL and HTL, while electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons transition from the excited state to the ground state, light is emitted. The injection and flow of holes and electrons should be balanced so that OLEDs with the above structure exhibit low operating voltage, excellent efficiency, and / or long lifetime.

[0004] The performance of organic light-emitting diodes can be affected by the characteristics of the hole injection layer, which in turn can be affected by the characteristics of the hole transport compounds and metal complexes contained in the hole injection layer.

[0005] There is still a need to improve the performance of metal complexes, their semiconductor layers, and electronic devices suitable for use as semiconductor materials, particularly by improving the properties of the metal complexes contained therein to achieve current efficiency, external quantum efficiency, and / or good operating voltage, as well as good stability such as lifetime and / or good operating voltage over time. Summary of the Invention

[0006] One aspect of the present invention provides a metal complex of formula (I).

[0007] ZnL2(AL) m (I)

[0008] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Wherein L comprises at least one aryl or heteroaryl group containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2.

[0009] According to one embodiment of the present invention, ligands of formula (II) in the following table are excluded:

[0010]

[0011] According to one embodiment of the present invention, metal complexes of formula (I) in the following table are excluded:

[0012]

[0013] Furthermore, one embodiment relates to a metal complex of formula (I).

[0014] ZnL2(AL) m (I)

[0015] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Wherein L comprises at least one aryl or heteroaryl group containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes ligands of formula (II):

[0016]

[0017] Furthermore, one embodiment relates to a metal complex of formula (I).

[0018] ZnL2(AL) m (I)

[0019] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Wherein L comprises at least one aryl or heteroaryl group containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes metal complexes of formula (I):

[0020]

[0021] definition

[0022] It should be noted that throughout this application and in the claims, metal complexes or metal complexes of formula (I) are also referred to as compounds.

[0023] It should be noted that throughout this application and in the claims, unless otherwise noted, any R... 1 R 2 R 3L and M always refer independently to the same part according to their definitions.

[0024] In this specification, unless otherwise defined, "substituted" means substituted or unsubstituted C1 to C1 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl groups and substituted or unsubstituted C2 to C3 groups 20 Heteroaryl groups, wherein the substituents are selected from substituted or unsubstituted C1 to C2 groups. 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl groups and substituted or unsubstituted C2 to C3 groups 20 The substituents of the heteroaryl group are independently selected from halogens, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl groups, and partially or perfluorinated C1 to C8 alkoxy groups.

[0025] In this specification, "aryl group" and "aromatic ring" refer to hydrocarbon groups that can be formed by formally isolating a hydrogen atom from an aromatic ring in a corresponding aromatic hydrocarbon. An aromatic hydrocarbon is a hydrocarbon containing at least one aromatic ring or aromatic ring system. An aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bonded carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons satisfying Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups such as biphenyl containing multiple aromatic rings linked by single bonds, and polycyclic groups such as naphthyl or fluorenyl containing fused rings.

[0026] Similarly, "heteroaryl" and "heteroaromatic" are particularly well understood as groups derived by formally isolating a cyclic hydrogen from a heterocyclic aromatic ring in a metal complex containing at least one heterocyclic aromatic ring.

[0027] The term "non-heterocyclic" should be understood as referring to a ring or ring system that does not contain heteroatoms as ring members.

[0028] The term "heterocycle" should be understood as referring to a heterocycle containing at least one ring that contains one or more heteroatoms. A heterocycle containing more than one ring means that all rings contain heteroatoms, or that at least one ring contains heteroatoms and at least one ring contains only carbon atoms without heteroatoms. A C2 heteroaryl group means that the heteroaryl ring contains two carbon atoms, and the other atoms are heteroatoms.

[0029] Heterocyclic alkyl groups are particularly well understood as groups derived by formally isolating a cyclic hydrogen from a saturated cyclic alkyl ring in a compound containing at least one saturated cyclic alkyl ring.

[0030] The term "aryl" having at least 9 carbon atoms may contain at least one fused aryl ring. The term "heteroaryl" having at least 9 atoms may contain at least one fused heteroaryl ring fused with a heteroaryl ring or fused with an aryl ring.

[0031] The terms "fused aryl ring" or "condensed aryl ring" should be understood as referring to two aryl rings sharing at least two common sp... 2 When carbon atoms are hybridized, they are considered fused or condensed.

[0032] The term "fused ring system" should be understood as a ring system in which two or more rings share at least two atoms.

[0033] The term "5, 6, or 7-membered ring" should be understood to refer to a ring containing 5, 6, or 7 atoms. The atoms may be selected from carbon and one or more heteroatoms.

[0034] In this specification, a single key refers to a direct key.

[0035] In this specification, unless otherwise defined, “substituted” means substituted with H, deuterium, halogen, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, or partially or perfluorinated C1 to C8 alkoxy.

[0036] In this specification, "substituted aryl" refers to, for example, a C6 to C6 group substituted with one or more substituents. 19 Aryl or C6 to C 18 Aryl, wherein the substituent may be unsubstituted or 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.

[0037] Accordingly, in this specification, "substituted heteroaryl" means, for example, substituted by one or more substituents, wherein the substituent itself may be substituted by one or more substituents, preferably, the substituents may be selected from H, deuterium, halogen, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, partially or perfluorinated C1 to C8 alkoxy.

[0038] In this specification, unless otherwise defined, a substituted heteroaryl group having at least two C ring atoms may be substituted with one or more substituents. For example, a substituted C2 heteroaryl group may have one or two substituents.

[0039] A substituted aryl group having at least 6 ring atoms may be substituted by 1, 2, 3, 4 or 5 substituents.

[0040] The substituted heteroaryl group may contain at least 5 or 6 ring atoms. If the heteroaryl group contains one heteroatom and five C atoms, the substituted heteroaryl group containing at least 5 or 6 ring atoms may be substituted by 1, 2, 3 or 4 substituents; or if the heteroaryl group having at least 6 ring atoms contains two heteroatoms and four C atoms, the heteroaryl group may be substituted by 1, 2 or 3 substituents; or if the heteroaryl group having at least 6 ring atoms contains three heteroatoms and three C atoms, the heteroaryl group may be substituted by 1 or 2 substituents, wherein the substituents are bonded only to C ring atoms.

[0041] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbon group. Alkyl groups can be C1 to C2. 12 Alkyl groups. More specifically, the alkyl groups can be C1 to C2. 10 Alkyl groups or C1 to C6 alkyl groups. For example, C1 to C4 alkyl groups contain 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and cyclohexyl.

[0042] Specific examples of alkyl groups can be methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, isobutyl groups, sec-butyl groups, tert-butyl groups, pentyl groups, branched pentyl groups, hexyl groups, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, adamantyl groups, etc.

[0043] In this specification, unless otherwise defined, "substituted alkyl group" can refer to a straight-chain, branched, or cyclic substituted saturated aliphatic hydrocarbon group. The substituted alkyl group can be straight-chain, branched, or cyclic C1 to C2. 12 Alkyl groups. More specifically, the substituted alkyl groups can be straight-chain, branched, or cyclic substituted C1 to C2 groups. 10 An alkyl group or a straight-chain, branched, or cyclic substituted C1 to C6 alkyl group. For example, a straight-chain, branched, or cyclic substituted C1 to C4 alkyl group contains 1 to 4 carbons in the alkyl chain and may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and cyclohexyl. Substituents may be selected from halogens, F, Cl, CN, OCH3, and OCF3.

[0044] The term "heteroatom" should be understood as a structure in which at least one carbon atom is replaced by another polyvalent atom in a structure that can be formed by covalently bonded carbon atoms. Preferably, the heteroatom is selected from B, Si, N, P, O, and S, more preferably from N, P, O, and S, and most preferably from N.

[0045] In this specification, when the substituent is not named, the substituent may be H.

[0046] The term "charge neutral" refers to the fact that the AL group is generally electrically neutral.

[0047] In the context of this invention, "different" means that the metal complexes do not have the same chemical structure.

[0048] The terms "without," "containing," and "not including" do not exclude impurities that may be present in the metal complex prior to deposition. Impurities have no technical effect on the objectives achieved by this invention.

[0049] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the two adjacent layers.

[0050] The terms "light-absorbing layer" and "light-absorbing layer" are used synonymously.

[0051] The terms “light-emitting layer,” “light-emitting layer,” and “emitting layer” are used synonymously.

[0052] The terms “OLED,” “organic light-emitting diode,” and “organic light-emitting device” are used synonymously.

[0053] The terms anode, anode layer, and anode electrode are used synonymously.

[0054] The term “at least two anode sublayers” should be understood to mean two or more anode sublayers, such as two or three anode sublayers.

[0055] The terms cathode, cathode layer, and cathode electrode are used synonymously.

[0056] The term "hole injection layer" should be understood as a layer that improves charge injection from the anode layer into other layers of an electronic device or from other layers of an electronic device into the anode.

[0057] The term "hole transport layer" should be understood as the layer that transports holes between the hole injection layer and other layers arranged between the hole injection layer and the cathode layer.

[0058] The operating voltage U is measured using a voltmeter.

[0059] In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that the contribution of the metal complex of formula (I) or a hole injection layer containing a metal complex of formula (I) to the visible emission spectrum of an electronic device such as an 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.

[0060] In the context of this invention, the term "sublimation" can refer to a change from a solid state to a gaseous state, or from a liquid state to a gaseous state.

[0061] In this specification, hole characteristics refer to the ability of supplying electrons to form holes when an electric field is applied, and the ability of holes formed in the anode to be easily injected into and transported in the light-emitting layer due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level.

[0062] Furthermore, electronic properties refer to the ability of electrons formed in the cathode to be readily injected into and transported in the light-emitting layer when an electric field is applied, due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level.

[0063] The term "HOMO level" should be understood as referring to the highest occupied molecular orbital energy level, and is measured in eV (electron volts).

[0064] The term "HOMO level further from the vacuum level" should be understood as meaning 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 from the vacuum level than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine" should be understood as meaning 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'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine.

[0065] The term "absolute value" should be understood as a value without a "-" sign. According to one embodiment of the invention, the HOMO energy level of the matrix compound in the hole injection layer can be calculated using quantum mechanical methods.

[0066] Beneficial effects

[0067] Surprisingly, it has been found that the electronic device according to the invention solves the fundamental problem of the invention by enabling electronic devices such as organic light-emitting diodes to outperform known electronic devices in several respects, particularly with regard to current efficiency, external quantum efficiency and / or good operating voltage and good stability such as lifetime and / or good operating voltage over time.

[0068] According to one embodiment, Zn has an oxidation state of +II (= Zn(II)) in the compound of formula (I).

[0069] According to one implementation, in ligand L, R 1 R 2 and R 3At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0070] Furthermore, one embodiment relates to a metal complex of formula (I).

[0071] ZnL2(AL) m (I)

[0072] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R 1 R 2 and R 3 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes ligands of formula (II):

[0073]

[0074] Furthermore, one embodiment relates to a metal complex of formula (I).

[0075] ZnL2(AL) m (I)

[0076] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R 1 R 2 and R 3 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group.2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes metal complexes of formula (I):

[0077]

[0078] Furthermore, one embodiment relates to a metal complex of formula (I).

[0079] ZnL2(AL) m (I)

[0080] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R 1 R 2 and R 3At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes ligands of formula (II):

[0081]

[0082] Furthermore, one embodiment relates to a metal complex of formula (I).

[0083] ZnL2(AL) m (I)

[0084] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R1 R 2 and R 3 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes metal complexes of formula (I):

[0085]

[0086] According to one implementation, in ligand L, R 1 and R 2 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0087] Furthermore, one embodiment relates to a metal complex of formula (I).

[0088] ZnL2(AL) m (I)

[0089] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R 1 and R 2 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes ligands of formula (II):

[0090]

[0091] Furthermore, one embodiment relates to a metal complex of formula (I).

[0092] ZnL2(AL) m (I)

[0093] Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Among the ligands L, R 1 and R 2 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2; and The following table excludes metal complexes of formula (I):

[0094]

[0095] According to one embodiment, the molecular weight of L is selected in the range of ≤ 600 Da but ≥ 176 Da, preferably in the range of ≤ 550 Da but ≥ 280 Da, and most preferably in the range of ≤ 550 Da but ≥ 240 Da.

[0096] According to one implementation, R 1 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0097] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 1 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R here 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; R 3 Selected from substituted or unsubstituted C1 to C 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0098] According to one embodiment, C6 to C are substituted or not substituted. 19 Aryl groups and substituted or unsubstituted C2 to C3 groups 20 The heteroaryl group is selected from formulas (III) and (IV). (III), (IV), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 4 R 5 R6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0099] According to one implementation, R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

[0100] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV); Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV); Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups.12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV), CN or NO2; and Where R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

[0101] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV), Where R 1 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV), CN or NO2; Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R here 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (III) or formula (IV); Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and Where R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

[0102] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups.12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV); Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III) or formula (IV).

[0103] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV); Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III) or formula (IV); and Where R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

[0104] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), provided that R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where R 3Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl groups, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III) or formula (IV), Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0105] According to one implementation, R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), provided that R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, formula (III) or formula (IV), Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl groups, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, formula (III) or formula (IV), Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; and Where R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

[0106] According to one implementation, R 3 It is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0107] According to one implementation, R 3Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, R 1 Selected from equation (III), and R 2 Selected from formula (IV), CH3, CF3 and CF2H.

[0108] According to one implementation, R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, R 1 Selected from equation (III), and R 2 Selected from formula (IV) and CF3.

[0109] According to one implementation, R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, R 1 Selected from equation (III), and R 2 Selected from formula (IV).

[0110] According to one implementation, R 3 Selected from CH3, CF3 and CF2H, R 1 Selected from equation (III), and R 2 Selected from formula (IV), CH3, CF3 and CF2H.

[0111] According to one implementation, R 3 Selected from CH3, CF3 and CF2H, R 1 Selected from equation (III), and R 2 Selected from formula (IV) and CF3.

[0112] According to one implementation, R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0113] According to one implementation, R 2 Selected from CH3, CF3, and CF2H; and R 3 Selected from CH3, CF3 and CF2H.

[0114] According to one implementation, R 1 Selected from substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0115] The above-described embodiments are inventive in themselves and can be the basis for a separate invention.

[0116] According to one implementation, R 1 Selected from formula (III); R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0117] The above-described embodiments are inventive in themselves and can be the basis for a separate invention.

[0118] According to one implementation, R 1 Selected from substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

[0119] The above-described embodiments are inventive in themselves and can be the basis for a separate invention.

[0120] According to one implementation, R 1 Selected from formula (III), R 2 Selected from CH3, CF3 and CF2H, and R 3 Selected from CH3, CF3, CF2H, and CN.

[0121] The above-described embodiments are inventive in themselves and can be the basis for a separate invention.

[0122] According to one implementation, R 3 Selected from CH3, CF3 and CF2H.

[0123] According to one implementation, R 3 Selected from CH3, CF3 and CF2H, R 1 Selected from equation (III), and R 2 Selected from formula (IV).

[0124] According to one implementation, R 4 R 5 R 6 R 7 R8 R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0125] According to one embodiment, C6 to C, whether substituted or unsubstituted, 19 Aryl groups and substituted or unsubstituted C2 to C3 groups 20 The heteroaryl group is selected from formulas (IIIa) and (IVa). (IIIa), (IVa), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 4 R 5 R 6 R 7 R 8 R 9 R 10 R11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0126] According to one implementation, in ligand L, R 1 Selected from formula (IIIb), (IIIb), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, CN, or NO2.

[0127] Preferably, R 2 and R 3 One of them is independently selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0128] According to one implementation, in ligand L, R 1 Selected from formula (IIIb'), (IIIb'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, CN, or NO2.

[0129] Preferably, R 2 and R 3 One of them is independently selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0130] According to one implementation, in ligand L, R 1 Selected from formula (IIIc), (IIIc), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics, Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0131] Preferably, R 2 and R 3 One of them is independently selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3.

[0132] According to one implementation, in ligand L, R 1 Selected from formula (IIIc'), (IIIc'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics, Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0133] Preferably, R 2 and R 3 One of them is independently selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3.

[0134] According to one implementation, in ligand L, R 1 Selected from formula (IIId), (IIId), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVb); R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, CN or NO2, formula (IVb); The condition is R 2 and R 3 One of them is selected from formula (IVb). (IVb), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0135] Preferably, R 2 and R 3 One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0136] According to one implementation, in ligand L, R1 Selected from formula (IIId'), (IIId'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVb'); R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, CN or NO2, formula (IVb'); The condition is R 2 and R 3 One of them is selected from formula (IVb'). (IVb'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0137] Preferably, R 2 and R 3 One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0138] According to one implementation, in ligand L, R 1 Selected from formula (IIId''), (IIId''), in X 1 Selected from N or CR 4 ; X2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, formula (IVb''); R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, CN or NO2, formula (IVb''); The condition is R 2 and R 3One of them is selected from formula (IVb''). (IVb''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF.

[0139] Preferably, R 2 and R 3 One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0140] According to one implementation, in ligand L, R1 Selected from formula (IIIe), (IIIe), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc), Where R2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc), CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; The condition is R 2 and R 3 One of them is selected from formula (IVc). (IVc), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups.12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0141] Preferably, R 2 and R 3 One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0142] According to one implementation, in ligand L, R 1 Selected from formula (IIIe'), (IIIe'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc'), CN or NO2, Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc'), CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; The condition is R 2 and R 3 One of them is selected from formula (IVc'). (IVc'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2, Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0143] Preferably, R 2 and R 3One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0144] According to one implementation, in ligand L, R 1 Selected from formula (IIIe''), (IIIe''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc''), CN or NO2, Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, formula (IVc''), CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; The condition is R 2 and R 3 One of them is selected from formula (IVc''). (IVc''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF.

[0145] Preferably, R 2 and R 3 One of them is selected from CH3, CF3 and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0146] According to one implementation, in ligand L, R 1 Selected from formula (IIIf), (IIIf), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 2 Selected from formula (IVd), (IVd), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; And R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, CN, or NO2.

[0147] According to one implementation, in ligand L, R 1 Selected from formula (IIIf'), (IIIf'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVd'), (IVd'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; And R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, CN, or NO2.

[0148] According to one implementation, in ligand L, R 1 Selected from formula (IIIf''), (IIIf''), in X 1Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVd''), (IVd''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; And R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, CN, or NO2.

[0149] According to one implementation, in ligand L, R 1 Selected from formula (IIIg), (IIIg), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from formula (IVe), (IVe), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0150] According to one implementation, in ligand L, R 1 Selected from formula (IIIg'), (IIIg'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVe'), (IVe'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0151] According to one implementation, in ligand L, R 1 Selected from formula (IIIg''), (IIIg''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVe''), (IVe''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Where R3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0152] According to one implementation, in ligand L, R 1 Selected from formula (IIIh), (IIIh), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 2 Selected from formula (IVf), (IVf), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0153] According to one implementation, in ligand L, R 1 Selected from formula (IIIh'), (IIIh'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVf'), (IVf'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0154] According to one implementation, in ligand L, R 1 Selected from formula (IIIh''), (IIIh''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVf''), (IVf''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0155] According to one embodiment, in the ligand of formula (II), R 1 Selected from formula (IIIi), (IIIi), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from formula (IVg), (IVg), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; And R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0156] According to one embodiment, in the ligand of formula (II), R 1 Selected from formula (IIIi'), (IIIi'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVg'), (IVg'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; And R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0157] According to one embodiment, in the ligand of formula (II), R 1 Selected from formula (IIIi''), (IIIi''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVg''), (IVg''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; And R 3 It is selected from CH3, CF3, CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0158] According to one implementation, in ligand L, R 1 Selected from formula (IIIj), (IIIj), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO; R 2 Selected from formula (IVh), (IVh), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; And R 3 Selected from CH3, CF3, and CF2H.

[0159] According to one implementation, in ligand L, R 1 Selected from formula (IIIj'), (IIIj'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVh'), (IVh'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; And R 3 Selected from CH3, CF3, and CF2H.

[0160] According to one implementation, in ligand L, R 1 Selected from formula (IIIj''), (IIIj''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVh''), (IVh''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups.12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; And R 3 Selected from CH3, CF3, and CF2H.

[0161] According to one implementation, in ligand L, R 1 Selected from formula (IIIk), (IIIk), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from formula (IVi), (IVi), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; And R 3 Selected from CH3, CF3, and CF2H.

[0162] According to one implementation, in ligand L, R 1 Selected from formula (IIIk'), (IIIk'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVi'), (IVi'), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; And R 3 Selected from CH3, CF3, and CF2H.

[0163] According to one implementation, in ligand L, R 1 Selected from formula (IIIk''), (IIIk''), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 4 R 5 R 6 R 7 and R 8 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from formula (IVi''), (IVi''), in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where R 9 R 10 R 11 R 12 and R 13 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; Where X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is selected from CF; preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least two of them are selected from CF; more preferably, X 1’ X 2’ X 3’ X 4’ and X 5’ At least three of them are selected from CF; And R 3 Selected from CH3, CF3, and CF2H.

[0164] According to one implementation, in ligand L, R 1 Selected from formula (IIIm), (IIIm), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN or NO2.

[0165] According to one implementation, in ligand L, R 1 Selected from formula (IIIm'), (IIIm'), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; Where R 4 R 5 R 6 R 7 and R 8 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, F, CN or NO2; Where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN or NO2.

[0166] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), R 4R 5 R 6 R 7 and R 8 At least one of them, if present, is independently selected from F, preferably at least two are independently selected from F, and preferably at least three are independently selected from F.

[0167] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), X 1 X 2 X 3 X 4 and X 5 At least one of them is independently selected from CF, preferably at least two are independently selected from CF, and more preferably at least three are independently selected from CF.

[0168] According to one implementation, in formulas (IV), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), R 9 R 10 R 11 R 12 and R 13 At least one of them, if present, is independently selected from F, preferably at least two are independently selected from F, and preferably at least three are independently selected from F.

[0169] According to one implementation, in formulas (IV), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), X 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them, 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.

[0170] According to one implementation, R in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm') 4 R 5 R 6 R 7 and R 8 At least one of them, if present, is independently selected from F, or R from equations (IV), (IVa) to (IVi), (IVb') to (IVi') and (IVb'') to (IVi'').9 R 10 R 11 R 12 and R 13 At least one of them is independently selected from F, preferably at least two are independently selected from F, and preferably at least three are independently selected from F.

[0171] According to one implementation, X in formulas (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm') 1 X 2 X 3 X 4 and X 5 X in at least one of the formulas (IV), (IVa) to (IVi), (IVb') to (IVi') and (IVb'') to (IVi'') 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is independently selected from CF, preferably at least two are independently selected from CF, and more preferably at least three are independently selected from CF.

[0172] According to one implementation, R in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm') 4 R 5 R 6 R 7 and R 8 At least one of them, if present, is independently selected from F, and R from equations (IV), (IVa) to (IVi), (IVb') to (IVi') and (IVb'') to (IVi''). 9 R 10 R 11 R 12 and R 13 At least one of them is independently selected from F, preferably at least two are independently selected from F, and preferably at least three are independently selected from F.

[0173] According to one implementation, X in formulas (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm') 1 X 2 X 3 X 4 and X5 At least one of them and X in formulas (IV), (IVa) to (IVi), (IVb') to (IVi') and (IVb'') to (IVi'') 1’ X 2’ X 3’ X 4’ and X 5’ At least one of them is independently selected from CF, preferably at least two are independently selected from CF, and more preferably at least three are independently selected from CF.

[0174] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), R 4 and R 8 If it exists, it is independently selected from H, D, and F; and

[0175] Where R 5 R 6 and R 7 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0176] According to one implementation, in formulas (IV), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), R 9 and R 13 If it exists, it is independently selected from H, D, and F; and

[0177] R 10 R 11 and R 12 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0178] According to one implementation, in formulas (III), (IV), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm), (IIIm'), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), R 4 R 8 R 9 and R 13 If it exists, it is independently selected from H, D, and F; and

[0179] R 5 R 6 R 7 R 10 R 11 and R 12 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

[0180] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), X 1 and X 5 At least one of them is independently selected from CH, CD, CF or N.

[0181] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), X 1 and X 5 It can be independently selected from CH, CD, CF, or N.

[0182] According to one implementation, in equations (III), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm) and (IIIm'), X 1 and X 5 At least one of them is independently selected from CH, CD, CF or N.

[0183] According to one implementation, in formulas (IV), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), X 1’ and X 5’ It can be independently selected from CH, CD, CF, or N.

[0184] According to one implementation, in formulas (III), (IV), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm), (IIIm'), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), X 1 and X 5 At least one of them and X 1’ and X 5’ At least one of them is independently selected from CH, CD, CF or N.

[0185] According to one implementation, in equations (III), (IV), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IIIm), (IIIm') and (IVa) to (IVi), X 1 X 5 X 1’ and X 5’ It can be independently selected from CH, CD, CF, or N.

[0186] According to one implementation, in formulas (III), (IV), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), X 1 X 5 X 1’ and X 5’ At least one of them, if present, is independently selected from CH, CD, CF or N.

[0187] According to one implementation, in formulas (III), (IV), (IIIa) to (IIIk), (IIIb') to (IIIk'), (IIId'') to (IIIk''), (IVa) to (IVi), (IVb') to (IVi'), and (IVb'') to (IVi''), X 1 X 5 X 1’ and X 5’If it exists, it is independently selected from CH, CD, CF or N.

[0188] According to one implementation, R 1 R 2 and R 3 At least one of them is independently selected from F1 to F25 F1 F2 F3 F4 F5 F6 F7 F8 F9 F10 F11 F12 F13 F14 F15 F16 F17 F18 F19 F20 F21 F22, F23 F24 F25.

[0189] According to one implementation, R 1 R 2 and R 3 At least one of them is independently selected from F1 to F24.

[0190] According to one implementation, R 1 Or R 2 At least one of them is independently selected from F1 to F25.

[0191] According to one implementation, R 1 Or R 2 At least one of them is independently selected from F1 to F24.

[0192] According to one implementation, R is selected from the following 1 and R 2 At least one of them is independently selected from F1 to F25: an aryl or heteroaryl group comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0193] According to one implementation, R is selected from the following 1 and R 2 At least one of the following is independently selected from F1 to F24, preferably from F1 to F9, more preferably from F1 to F7, and most preferably from F1 to F6: an aryl or heteroaryl group comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0194] According to one implementation, R 1 Selected from aryl or heteroaryl groups containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0195] According to one implementation, R is selected from the following 1 Independently selected from F1 to F25: aryl or heteroaryl containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0196] According to one implementation, R is selected from the following 1 Independently selected from F1 to F24, preferably from F1 to F9, more preferably from F1 to F7, and most preferably from F1 to F6: an aryl or heteroaryl group comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0197] According to one implementation, the remaining R 1 R 2 and R 3 (=Not selected from aryl or heteroaryl groups containing at least three F groups, wherein the F groups are sp...) 2 (One of the hybridized carbon atoms directly bonded) is selected from substituted or unsubstituted C6 to C7. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0198] By doing so, the rise in operating voltage over time can be reduced, i.e., improved.

[0199] According to one implementation, R 1 R 2 and R 3 At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; and

[0200] The rest of R 1 R 2 and R 3 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0201] By doing so, the rise in operating voltage over time can be reduced, i.e., improved.

[0202] According to one implementation, R 1 R 2 and R 3 At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded, independently selected from F1 to F25; and

[0203] in the remaining R 1 R 2 and R 3 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0204] By doing so, the rise in operating voltage over time can be reduced, i.e., improved.

[0205] According to one implementation, R 1 R 2 and R 3 At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded, independently selected from F1 to F24; and

[0206] in the remaining R 1 R 2 and R 3 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0207] By doing so, the rise in operating voltage over time can be reduced, i.e., improved.

[0208] According to one implementation, R 1 and R 2At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; and

[0209] The remaining R 1 and R 2 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0210] By doing so, the rise in operating voltage over time can be reduced, or improved, to an even greater extent.

[0211] According to one implementation, R 1 and R 2 At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded, independently selected from F1 to F25; and

[0212] The remaining R 1 and R 2 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0213] By doing so, the rise in operating voltage over time can be reduced, or improved, to an even greater extent.

[0214] According to one implementation, R 1 and R 2 At least one of them is independently selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded, independently selected from F1 to F24; and

[0215] The remaining R 1 and R 2 One of them is selected from substituted or unsubstituted C6 to C14. 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatic compounds.

[0216] By doing so, the rise in operating voltage over time can be reduced, or improved, to an even greater extent.

[0217] According to one embodiment, the aryl or heteroaryl group is selected from phenyl, pyridyl, or pyrimidinyl, preferably from phenyl or pyridyl, more preferably from phenyl: at least one aryl or heteroaryl group comprising at least three F groups in ligand L, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

[0218] In other words, according to one embodiment, L comprises at least one phenyl or pyridyl or pyrimidinyl group containing at least three F groups, wherein the F groups are sp[i] with the ring of an aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; preferably, L comprises at least one phenyl or pyridyl group containing at least three F groups, said F groups being sp... 2 - Hybridized carbon atoms are directly bonded; more preferably, L comprises at least one phenyl group containing at least one F group, said F group being sp... 2 - Hybridized carbon atoms are directly bonded.

[0219] According to one embodiment, it includes at least three sp rings with aryl or heteroaryl groups. 2 - The R of the F group directly bonded to the hybridized carbon atom 1 R 2 and R 3 At least one of the aryl or heteroaryl groups is selected from phenyl, pyridyl or pyrimidinyl, preferably from phenyl or pyridyl, and more preferably from phenyl.

[0220] In other words, according to one implementation method, R 1 R 2 and R 3 At least one of them is selected from phenyl, pyridyl, or pyrimidinyl groups containing at least three F groups, wherein the F groups are sp[i] with the ring of aryl or heteroaryl. 2 - Hybridized carbon atoms are directly bonded; preferably, R 1 R 2 and R 3 At least one of them is selected from phenyl or pyridyl groups containing at least three F groups, wherein the F groups are sp[i] with the ring of aryl or heteroaryl. 2 - Hybridized carbon atoms are directly bonded; more preferably, R 1 R 2 and R 3 At least one of them is selected from phenyl groups containing at least three F groups, said F groups being sp[i] of the aryl ring. 2 - Hybridized carbon atoms are directly bonded.

[0221] According to one implementation, R 1 and / or R 2Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E67. E1、 E2, E3 E4 E5 E6 E7 E8 E9 E10 E11、 E12 E13 E14 E15 E16 E17 E18 E19 E20 E21 E22 E23 E24 E25 E26 E27 E28 E29 E30 E31 E32 E33 E34 E35 E36 E37 E38 E38 E40 E41 E42 E43 E44 E45 E46 E47 E48 E49 E50 E51 E52 E53 E54 E55 E56 E57 E58 E59 E60 E61 E62 E63 E64 E65 E66 E67, R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E67; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E67.

[0222] According to one implementation, R 1 and / or R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E66; R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E66; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E66.

[0223] According to one implementation, R 1 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26 and E67; R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26 and E67; and R 3Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26 and E67.

[0224] According to one implementation, R 1 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26; R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E26.

[0225] According to one implementation, R 1 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24 and E67; R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24 and E67; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24 and E67.

[0226] According to one implementation, R 1 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24. R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas E1 to E24.

[0227] According to one implementation, R 1 and / or R 2 Selected from formulas G1 to G16 G1 G2 G3 G4 G5 G6 G7 G8 G9 G10 G11 G12 G13 G14 G15 G16.

[0228] According to one implementation, R 1 and / or R 2 Selected from formulas G1 to G15.

[0229] According to one implementation, R 1 and / or R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas H1 to H19. H1, H2, H3 H4 H5 H6 H7 H8 H9 H10, H11, H12, H13 H14 H15 H16 H17 H18 H19, And R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas H1 to H19.

[0230] According to one implementation, R 2 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas H1 to H17; and R 3 Selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, NO2, or selected from formulas H1 to H17.

[0231] According to one implementation, R 1 Selected from formulas G1 to G16 G1 G2 G3 G4 G5 G6 G7 G8 G9 G10 G11 G12 G13 G14 G15 G16; and R 2 Selected from CF3, Equations H1 to H19 H1, H2, H3 H4 H5 H6 H7 H8 H9 H10, H11, H12, H13 H14 H15 H16 H17 H18 H19; R 3The ingredients are selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, and NO2, preferably from CH3, CF3, and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0232] According to one implementation, R 1 Selected from formulas G1 to G15; R 2 Selected from CF3, formulas H1 to H19; and R 3 The ingredients are selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, and NO2, preferably from CH3, CF3, and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0233] According to one implementation, R 1 Selected from formulas G1 to G16; Where R 2 Selected from CF3 or formulas H1 to H17; and Where R 3 The ingredients are selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, and NO2, preferably from CH3, CF3, and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0234] According to one implementation, R 1 Selected from formulas G1 to G15; Where R 2 Selected from CF3 or formulas H1 to H17; and Where R 3 The ingredients are selected from CH3, CH2D, CHD2, CD3, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN, and NO2, preferably from CH3, CF3, and CF2H, more preferably from CH3 and CF3, and most preferably from CH3.

[0235] According to one embodiment, ligand L and / or the ligand of formula (II) further comprises at least one group selected from the group consisting of F, CN, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0236] According to one embodiment, ligand L and / or the ligand of formula (II) further comprises at least one group selected from the group consisting of a sp group of an aryl or heteroaryl ring. 2- Hybridized carbon atoms directly bonded to F, CN, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

[0237] According to one embodiment, ligand L and / or the ligand of formula (II) further comprises ≥2 to ≤10 groups selected from the group consisting of: sp groups of an aryl or heteroaryl ring. 2 - F, CN, CF3, CF2H, CF2D, CFH2, CFHD or CFD2 directly bonded to hybridized carbon atoms, preferably containing ≥3 to ≤10 groups, more preferably containing ≥4 to ≤10 groups.

[0238] The amount of ligand L and / or CN group in formula (II)

[0239] According to one embodiment, ligand L and / or the ligand of formula (II) contains 0 ≥ to ≤ 4 CN groups, preferably 0 ≥ to ≤ 3 CN groups, more preferably 0 ≥ to ≤ 2 CN groups, and most preferably contains no CN groups or contains one CN group.

[0240] According to one embodiment, ligand L and / or the ligand of formula (II) comprises 0 ≥ to ≤ 4 CN groups, said CN groups being sp... 2 - Hybridized carbon atoms are directly bonded, preferably containing 0 ≥ to ≤3 CN groups, more preferably containing 0 ≥ to ≤2 CN groups, and most preferably containing no CN groups or containing one CN group.

[0241] Compound of formula (I)

[0242] According to one embodiment, the compounds of formula (I) are selected from A1 to A60, B1 to B12, C1 to C7, and D1 to D23: A1、 A2, A3 A4 A5 A6 A7 A8 A9 A10 A11、 A12, A13、 A14 A15 A16 A17 A18 A19 A20 A21, A22、 A23、 A24、 A25、 A26、 A27、 A28、 A29、 A30、 A31、 A32、 A33、 A34、 A35、 A36、 A37、 A38、 A39、 A40ぁ A41、 A42ぁ A43ぁ A44ぁ A45ぁ A46、 A47、 A48ぁ A49ぁ A50ぁ A51ぁ A52ぁ A53ぁ A54ぁ A55ぁ A56、 A57ぁ A58ぁ A59ぁ A60ぁ B1、 B2、 B3、 B4、 B5、 B6、 B7、 B8、 B9、 B10、 B11、 B12、 C1、 C2、 C3、 C4、 C5、 C6、 C7、 D1、 D2、 D3、 D4、 D5、 D6、 D7 D8、 D9 D10 D11、 D12 D13 D14 D15 D16 D17 D18 D19 D20 D21 D22、 D23.

[0243] According to one embodiment, the compound of formula (I) is selected from A1, A2, A4 to A60, B1 to B12, C1 to C7, D1 to D23.

[0244] According to one embodiment, the compound of formula (I) is selected from A1 to A60, B1 to B12, C1 to C7 and D1 to D19.

[0245] According to one embodiment, the compound of formula (I) is selected from A1, A2, A4 to A60, B1 to B12, C1 to C7 and D1 to D19.

[0246] According to a preferred embodiment, the compound of formula (I) is selected from A1 to A60, B1 to B12 and C1 to C7.

[0247] According to a preferred embodiment, the compound of formula (I) is selected from A1, A2, A4 to A60, B1 to B12 and C1 to C7.

[0248] According to a more preferred embodiment, the compound of formula (I) is selected from A1 to A60 and B1 to B12.

[0249] According to a more preferred embodiment, the compound of formula (I) is selected from A1, A2, A4 to A60 and B1 to B12.

[0250] According to a preferred embodiment, the compound of formula (I) is selected from A1 to A60.

[0251] According to a preferred embodiment, the compound of formula (I) is selected from A1 to A60.

[0252] According to one embodiment, the ligand L of formula (I) may be selected from a group containing at least 12 carbon atoms but at most 21 carbon atoms, or at least 12 carbon atoms but at most 20 carbon atoms, or at least 12 carbon atoms but at most 19 carbon atoms, or at least 12 carbon atoms but at most 18 carbon atoms, or at least 12 carbon atoms but at most 17 carbon atoms.

[0253] According to one embodiment, the metal complex of formula (I) has a LUMO energy level in the range of ≥-4.10 eV to ≤-1.0 eV, preferably in the range of ≥-4.0 eV to ≤-1.5 eV, more preferably in the range of ≥-3.9 eV to ≤-1.6 eV, and most preferably in the range of ≥-3.8 eV to ≤-1.7 eV.

[0254] According to one embodiment, the band gap (the difference between the LUMO and HOMO levels) is ≥ 3.1 eV, preferably ≥ 3.2 eV, and more preferably ≥ 3.3 eV.

[0255] The auxiliary ligand AL and the term "m"

[0256] The term “m” is an integer selected from 0 to 2, that is, “m” is an integer selected from 0, 1 or 2.

[0257] According to one implementation, "m" is an integer selected from 0 or 1. According to another implementation, "m" is an integer selected from 1.

[0258] According to one implementation, "m" is an integer selected from 2.

[0259] According to one implementation, "m" is an integer selected from 1.

[0260] According to one implementation, "m" is preferably an integer selected from 0.

[0261] According to one implementation, AL is charge neutral.

[0262] According to one embodiment of formula (I), AL is selected from H2O, C2 to C 40 Monodentate or multidentate ethers and C2 to C 40 Sulfides, C2 to C 40 Amines, C2 to C 40 Phosphine, C2 to C 20 Alkyl nitrile or C2 to C 40 Aryl nitrile or compounds according to formula (XX); (XX), where R 20 and R 21 Independently selected from C1 to C 20Alkyl, C1 to C 20 Heteroalkyl, C6 to C 20 Aryl, heteroaryl with 5 to 20 cyclic atoms, halogenated or fully halogenated C1 to C2 groups 20 Alkyl, halogenated or fully halogenated C1 to C1 20 Heteroalkyl, halogenated or fully halogenated C6 to C 20 A heteroaryl group having 5 to 20 cyclic atoms, aryl, halogenated or perhalogenated, or at least one R 20 and R 21 Bridge and form 5 to 20 element rings, or two Rs 20 and / or two Rs 21 Bridges and forms 5 to 40-membered rings, or forms rings containing unsubstituted elements or C1 to C1. 12 Substituted phenanthroline rings of 5 to 40 members.

[0263] According to one embodiment of this application, AL is H2O and m is 1.

[0264] Uses of the compounds of this invention

[0265] The present invention also relates to the use of compounds of formula (I) in organic devices.

[0266] The present invention also relates to the use of compounds of formula (I) in organic semiconductor layers.

[0267] The present invention also relates to the use of the compound of formula (I) as a p-type dopant.

[0268] All preferred embodiments of the compound of formula (I) may be applied arbitrarily.

[0269] semiconductor materials

[0270] According to another aspect, a semiconductor material is provided, the semiconductor material comprising at least one compound of formula (I) according to the invention.

[0271] According to one embodiment, the semiconductor material further comprises at least one covalent matrix compound or at least one substantially covalent matrix compound.

[0272] According to another aspect, the semiconductor material comprises at least one compound of formula (I) according to the invention and at least one additional covalent matrix compound or at least one substantially covalent matrix compound.

[0273] Organic semiconductor layer

[0274] According to another aspect, an organic semiconductor layer is provided, the organic semiconductor layer comprising at least one compound of formula (I) according to the invention.

[0275] According to one embodiment of the present invention, the organic semiconductor layer is a hole injection layer.

[0276] Organic semiconductor layers can be formed on the anode or cathode layer via vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When forming organic semiconductor layers using vacuum deposition, the deposition conditions can vary depending on the compound used to form the layer and the desired structure and thermal properties of the layer. Generally, however, vacuum deposition conditions can include deposition temperatures ranging from 100°C to 350°C, and 10... -8 Up to 10 -3 The pressure was 1 Torr (1 Torr equals 133.322 Pa) and the deposition rate was 0.1 nm / s to 10 nm / s.

[0277] When forming an organic semiconductor layer using spin coating or printing, the coating conditions can vary depending on the compound used to form the layer and the desired structure and thermal properties of the organic semiconductor layer. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0278] The thickness of the organic semiconductor layer can be in the range of about 1 nm to about 20 nm, for example, in the range of about 2 nm to about 15 nm, or in the range of about 2 nm to about 12 nm.

[0279] When the thickness of the organic semiconductor layer is within this range, the organic semiconductor layer can have excellent hole injection and / or hole generation characteristics without substantially damaging the driving voltage.

[0280] 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%, more preferably about ≥ 1 wt% to about ≤ 15 wt% of the compound of formula (I), and - At least about ≥ 70 wt% to about ≤ 99.5 wt%, preferably about ≥ 80 wt% to about ≤ 99.5 wt%, more preferably about ≥ 85 wt% to about ≤ 99 wt% of a substantially covalent matrix compound; preferably, the weight % of the compound of formula (I) is less than the weight % of the substantially covalent matrix compound; wherein the weight % of the components is based on the total weight of the organic semiconductor layer.

[0281] According to one embodiment of the present invention, the organic semiconductor layer and / or the compound of formula (I) is non-luminescent.

[0282] In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that the contribution of a compound or layer to the visible emission spectrum of a device is less than 10%, preferably less than 5%, relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0283] Basically covalent matrix compound / covalent matrix compound

[0284] According to another aspect of the invention, the semiconductor material and / or organic semiconductor layer may also comprise a substantially covalent matrix compound.

[0285] A substantially covalent matrix compound, also known as a matrix compound, can be an organic aromatic matrix compound containing covalently bonded carbon atoms. A substantially covalent matrix compound can be an organic compound consisting substantially of covalently bonded C, H, O, N, and S atoms, optionally also containing covalently bonded B, P, or Si atoms. A substantially covalent matrix compound can be an organic aromatic covalently bonded compound without metal atoms, and most of its skeletal atoms can be selected from C, O, S, and N, preferably from C, O, and N, wherein the majority of the atoms are C atoms. Alternatively, the covalent matrix compound does not contain metal atoms, and most of its skeletal atoms can be selected from C and N; preferably, the covalent matrix compound does not contain metal atoms, and most of its skeletal atoms can be selected from C, and a minority of its skeletal atoms can be N.

[0286] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≥ 400 g / mol but ≤ 2000 g / mol, preferably ≥ 450 g / mol but ≤ 1500 g / mol, more preferably ≥ 500 g / mol but ≤ 1000 g / mol, additionally preferably ≥ 550 g / mol but ≤ 900 g / mol, and even more preferably ≥ 600 g / mol but ≤ 800 g / mol.

[0287] In one embodiment, when measured under the same conditions, the HOMO level of a substantially covalent matrix compound can be more negative than that of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobis[fluorene]-2,2',7,7'-tetramine (CAS 207739-72-8).

[0288] In one embodiment of the invention, the substantially covalent matrix compound may be free of alkoxy groups.

[0289] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0290] Preferably, the substantially covalent matrix compound does not contain TPD or NPB.

[0291] Compounds of formula (IXa) or compounds of formula (IXb)

[0292] According to another aspect of the invention, the substantially covalent matrix compound, or covalent matrix compound as referred to herein, may comprise at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IXa), or a compound of formula (IXb): (IXa), (IXb), in: T 1 T 2 T 3 T 4 and T 5 It is independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably selected from single bond or phenylene group; T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Independently selected from substituted or unsubstituted C6 to C6. 20 aryl; or substituted or unsubstituted C3 to C4. 20Heteroarylene groups; substituted or unsubstituted biphenylidene; 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 biphenylidene; substituted or unsubstituted tetraphenyl; substituted or unsubstituted benzo[a]anthracene; substituted or unsubstituted dibenzofuran; substituted or unsubstituted dibenzothiophene; substituted or unsubstituted xanthones; substituted or unsubstituted carbazole; substituted 9-phenylcarbazole; substituted or unsubstituted azaheptanyl; substituted or unsubstituted dibenzo[b,f]azaheptanyl; substituted or unsubstituted 9,9' - spirodi[fluorene]; substituted or unsubstituted spiro[fluorene-9,9'-xanton]; or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene; or fused ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, wherein the 5 to 7-membered rings are selected from (i) unsaturated 5 to 7-membered rings of heterocyclic rings, (ii) 5 to 6-membered rings of aromatic heterocyclic rings, (iii) unsaturated 5 to 7-membered rings of non-heterocyclic rings, and (iv) 6-membered rings of aromatic non-heterocyclic rings; in Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H; D; F; C(-O)R, either the same or different. 2 ;CN;Si(R 2 )3;P(-O)(R 2 )2; OR 2 ;S(-O)R 2 S(-O)2R 2 ; substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms; substituted or unsubstituted alkenyl or ynyl groups having 2 to 20 carbon atoms; 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 C6 to C 18 Aryl; unsubstituted C3 to C 18 Heteroaryl; a fused ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the 5 to 7-membered rings are selected from unsaturated 5 to 7-membered heterocyclic rings, 5 to 6-membered aromatic heterocyclic rings, unsaturated 5 to 7-membered non-heterocyclic rings, and 6-membered aromatic non-heterocyclic rings. Where R 2The following can be selected from H, D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, C6 to C 18 Aryl or C3 to C 18 Mixed aromatic compounds.

[0293] Preferably, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, either the same as or different from H; straight-chain alkyl groups having 1 to 6 carbon atoms; branched alkyl groups having 1 to 6 carbon atoms; cyclic alkyl groups having 3 to 6 carbon atoms; alkenyl or ynyl groups having 2 to 6 carbon atoms; C6 to C6. 18 Aryl; C3 to C 18 Heteroaryl; a fused ring system comprising 2 to 4 unsubstituted 5 to 7-membered rings, wherein the 5 to 7-membered rings are selected from unsaturated 5 to 7-membered heterocyclic rings, 5 to 6-membered aromatic heterocyclic rings, unsaturated 5 to 7-membered non-heterocyclic rings, and 6-membered aromatic non-heterocyclic rings; more preferably, the substituents are selected from H, straight-chain alkyl groups having 1 to 4 carbon atoms, branched alkyl groups having 1 to 4 carbon atoms, cyclic alkyl groups having 3 to 4 carbon atoms, and / or phenyl groups.

[0294] Thus, compounds of formula (IXa) or (IXb) can have a standard starting temperature suitable for large-scale production.

[0295] According to one embodiment of the semiconductor material and / or organic semiconductor layer, wherein the substantially covalent matrix compound comprises a compound of formula (IXa) or (IXb): (IXa), (IXb), in T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably selected from single bond or phenylene group; T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from unsubstituted C6 to C6. 20aryl; or unsubstituted C3 to C4 20 Heteroarylene; Unsubstituted biphenylidene; Unsubstituted fluorene; Substituted 9-fluorene; Substituted 9,9-fluorene; Unsubstituted naphthalene; Unsubstituted anthracene; Unsubstituted phenanthrene; Unsubstituted pyrene; Unsubstituted perylene; Unsubstituted triphenylidene; Unsubstituted tetraphenyl; Unsubstituted benzo[b,f]-anthracene; Unsubstituted dibenzofuran; Unsubstituted dibenzothiophene; Unsubstituted xanthone; Unsubstituted carbazole; Substituted 9-phenylcarbazole; Unsubstituted aziridine heptane; Unsubstituted dibenzo[b,f]aziridine heptane; Unsubstituted 9,9'-spirodi[fluorene]; Unsubstituted spirodi[b,f]-spirodi[fluorene] [fluorene-9,9'-xanton]; or an unsubstituted aromatic fused-ring system comprising at least three unsubstituted aromatic rings selected from unsubstituted non-heterocyclic rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings and / or unsubstituted 7-membered rings, unsubstituted fluorene; or a fused-ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the 5 to 7-membered rings are selected from (i) unsaturated 5 to 7-membered rings of heterocyclic rings, (ii) 5 to 6-membered rings of aromatic heterocyclic rings, (iii) unsaturated 5 to 7-membered rings of non-heterocyclic rings, and (iv) 6-membered rings of aromatic non-heterocyclic rings.

[0296] According to one embodiment of the semiconductor material and / or organic semiconductor layer, wherein the substantially covalent matrix compound comprises a compound of formula (IXa) or (IXb): (IXa), (IXb), in T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably selected from single bond or phenylene group; T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from unsubstituted C6 to C6. 20 aryl; or unsubstituted C3 to C4 20Heteroarylene; unsubstituted biphenylidene; unsubstituted fluorene; substituted 9-fluorene; substituted 9,9-fluorene; unsubstituted naphthalene; unsubstituted anthracene; unsubstituted phenanthrene; unsubstituted pyrene; unsubstituted perylene; unsubstituted triphenylidene; unsubstituted tetraphenyl; unsubstituted benzo[b,f]-anthracene; unsubstituted dibenzofuran; unsubstituted dibenzothiophene; unsubstituted saxon; unsubstituted carbazole; substituted 9-phenylcarbazole; unsubstituted azircycloheptanyl; unsubstituted dibenzo[b,f]azircycloheptanyl; unsubstituted 9,9'-spirodi[fluorene]; unsubstituted spiro[fluorene-9,9'-saxon].

[0297] Thus, compounds of formula (IXa) or (IXb) can have a standard starting temperature suitable for large-scale production.

[0298] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bonds, phenylene groups, biphenylene groups, or triphenylene groups.

[0299] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene, biphenylene, or terphenylene, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond. According to one implementation, where T... 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond.

[0300] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T 4 and T 5The two in it are single bonds.

[0301] According to one implementation, where T 1 T 2 and T 3 It can be independently selected from the phenylene group, and T 1 T 2 and T 3 One of them is a single bond.

[0302] According to one implementation, where T 1 T 2 and T 3 It can be independently selected from phenylene groups, and T 1 T 2 and T 3 The two in it are single bonds.

[0303] According to one implementation, where T 6 It can be a phenylene group, a biphenylene group, or a terphenylene group. According to one embodiment, T... 6 It can be a benzene group.

[0304] According to one implementation, where T 6 It can be a biphenyl group. According to one embodiment, where T... 6 It could be a triphenylene oxide.

[0305] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from equations (I1) to (I16): (I1) (I2) (I3) (I4) (I5) (I6) (I7) (I8) (I9) (I10) (I11) (I12) (I13) (I14) (I15) (I16), Among them, the asterisk " "Indicates the position of combination.

[0306] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be selected independently from (I1) to (I15); or selected from (I1) to (I10) and (I13) to (I15).

[0307] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from (I1), (I2), (I5), (I7), (I9), (I10), (I13) to (I16).

[0308] When selecting Ar within this range 1 Ar 2 Ar 3 Ar 4 and Ar 5 At that time, the standard starting temperature can be within a range that is particularly suitable for large-scale production.

[0309] "Matrix compounds of formula (IXa) or (IXb)" may also be called "hole transport compounds".

[0310] According to one embodiment, the compound of formula (IXa) or formula (IXb) may comprise an aromatic fused ring system containing at least 1 to 6 substituted or unsubstituted heteroaromatic rings.

[0311] According to one embodiment, the compound of formula (IXa) or formula (IXb) may comprise an aromatic fused ring system containing at least 1 to 6 substituted or unsubstituted heterocyclic rings and an unsaturated 5 to 7-membered ring containing at least 1 to 3 substituted or unsubstituted heterocyclic rings, preferably an aromatic fused ring system containing at least 2 to 5 substituted or unsubstituted heterocyclic rings.

[0312] According to one embodiment, the compound of formula (IXa) or (IXb) may comprise an aromatic fused ring system comprising at least 1 to 6 substituted or unsubstituted heterocyclic rings and an unsaturated 5- to 7-membered ring comprising at least 1 to 3 substituted or unsubstituted heterocyclic rings, preferably an aromatic fused ring system comprising at least 2 to 5 substituted or unsubstituted heterocyclic rings and an unsaturated 5- to 7-membered ring comprising at least 1 to 3 substituted or unsubstituted heterocyclic rings, more preferably an aromatic fused ring system comprising 3 or 4 substituted or unsubstituted heterocyclic rings and optionally an unsaturated 5- to 7-membered ring comprising at least 1 to 3 substituted or unsubstituted heterocyclic rings, and additionally preferably the aromatic fused ring system comprising heterocyclic rings is unsubstituted and optionally an unsaturated 5- to 7-membered ring comprising at least 1 to 3 unsubstituted heterocyclic rings.

[0313] According to one embodiment, the compound of formula (IXa) or (IXb) may comprise: - A substituted or unsubstituted aromatic fused ring system having at least 2 to ≤ 6, preferably 3 to ≤ 5 or 4 fused aromatic rings, wherein the fused aromatic rings are selected from substituted or unsubstituted non-heteroaromatic rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or unsaturated 5- to 7-membered rings of substituted or unsubstituted heterocycles; or - An unsubstituted aromatic fused ring system having at least 2 to ≤ 6, preferably 3 to ≤ 5 or 4 fused aromatic rings, wherein the fused aromatic rings are selected from unsubstituted non-heteroaromatic rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings and / or unsaturated 5- to 7-membered rings of unsubstituted heterocycles.

[0314] It should be noted here that the term "aromatic fused ring system" may include at least one aromatic ring and at least one substituted or unsubstituted unsaturated 5- to 7-membered ring. It should also be noted here that the substituted or unsubstituted unsaturated 5- to 7-membered ring may not be an aromatic ring.

[0315] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or a substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl or fluorenyl.

[0316] According to one embodiment of the invention, the compound of formula (IXa) or formula (IXb) is selected from formulas (K1) to (K23): (K1) (K2) (K3) (K4) (K5) (K6) (K7) (K8) (K9) (K10) (K11) (K12) (K13) (K14) (K15) (K16) (K17) (K18) (K19) (K20) (K21) (K22) (K23); Preferably, the compound of formula (IXa) or formula (IXb) is selected from formula (K3) to (K23), more preferably from (K4) to (K23), and most preferably from (K18).

[0317] Organic electronic devices

[0318] 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).

[0319] 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).

[0320] According to one embodiment of the present invention, the organic electronic device includes an anode layer, a cathode layer and an organic semiconductor layer according to the present invention, preferably, the organic semiconductor layer is disposed between the anode layer and the cathode layer.

[0321] Preferably, the organic semiconductor layer is arranged adjacent to the anode layer; more preferably, the organic semiconductor layer is arranged in direct contact with the anode layer.

[0322] Preferably, such an organic semiconductor layer is a hole injection layer.

[0323] Surprisingly, such organic electronic devices exhibit improved performance for many applications within the present invention, particularly in terms of current efficiency, external quantum efficiency, and / or good operating voltage, as well as good stability such as lifetime and / or good operating voltage over time.

[0324] According to one embodiment of the present invention, the organic electronic device is selected from light-emitting devices, thin-film transistors, batteries, display devices, photovoltaic cells or organic photodetectors, preferably selected from light-emitting devices, and preferably, the electronic device is part of a display device or a lighting device.

[0325] According to one embodiment, the organic electronic device comprises a compound of formula (I) according to the invention, which 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, preferably a light-emitting device, and preferably, the electronic device is part of a display device or a lighting device.

[0326] According to one embodiment of the present invention, the organic electronic device further includes at least one photoactive layer, wherein the at least one photoactive layer is disposed between the anode layer and the cathode layer.

[0327] According to one embodiment of the present invention, the organic electronic device includes at least one photoactive layer, and at least one organic semiconductor layer is disposed between the anode and at least one photoactive layer.

[0328] According to one embodiment, the organic electronic device includes 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 disposed 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).

[0329] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention.

[0330] According to one embodiment of the present invention, the organic semiconductor layer is arranged and / or provided adjacent to the anode layer.

[0331] According to one embodiment of the present invention, the organic semiconductor layer of the present invention is a hole injection layer.

[0332] In cases where the semiconductor layer of the present invention is a hole injection layer and / or is arranged and / or provided adjacent to the anode layer, it is particularly preferred that the layer is substantially composed of a compound of formula (I).

[0333] In the context of this specification, the term "consistently of" specifically refers to and / or includes concentrations of ≥ 90% (volume / volume), more preferably ≥ 95% (volume / volume), and most preferably ≥ 99% (volume / volume).

[0334] According to another aspect, the semiconductor layer may have a thickness of at least about ≥ 0.5 nm to about ≤ 10 nm, preferably about ≥ 2 nm to about ≤ 8 nm, and even more preferably about ≥ 3 nm to about ≤ 5 nm.

[0335] According to one embodiment of the invention, the semiconductor layer of the 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.

[0336] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode.

[0337] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode, and emits light through a cathode layer.

[0338] The present invention also relates to a display device comprising organic electronic devices according to the present invention.

[0339] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode.

[0340] The present invention also relates to a display device comprising organic electronic devices according to the present invention.

[0341] Other layers

[0342] According to the present invention, in addition to the layers already mentioned above, organic electronic devices may also include other layers. Exemplary embodiments of each layer are described below: base The substrate can be any substrate commonly used in the manufacture of electronic devices such as organic light-emitting diodes (OLEDs). If light is to be emitted through the substrate, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0343] Anode layer

[0344] The anode layer, also known as the anode electrode, is formed by deposition or sputtering of the material used to form the anode layer. The material used to form the anode layer can be a high work function material to facilitate hole injection. The anode layer can 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 (AlZO), and zinc oxide (ZnO) can be used to form the anode layer. The anode layer can also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.

[0345] An anode layer may contain two or more anode sublayers.

[0346] According to one embodiment, the anode layer includes a first anode sublayer and a second anode sublayer, wherein the first anode sublayer is arranged closer to the substrate and the second anode sublayer is arranged closer to the cathode layer.

[0347] According to one embodiment, the anode layer may include a first anode sublayer and a second anode sublayer, wherein the first anode sublayer contains or is composed of Ag or Au, and the second anode sublayer contains or is composed of a transparent conductive oxide.

[0348] According to one embodiment, the anode layer includes a first anode sublayer, a second anode sublayer, and a third anode sublayer, wherein the first anode sublayer is arranged closer to the substrate, the second anode sublayer is arranged closer to the cathode layer, and the third anode sublayer is arranged between the substrate and the first anode sublayer.

[0349] According to one embodiment, the anode layer may include a first anode sublayer, a second anode sublayer, and optionally a third anode sublayer. The first anode sublayer comprises or is composed of Ag or Au, the second anode sublayer comprises or is composed of a transparent conductive oxide, and the third anode sublayer comprises or is composed of a transparent conductive oxide. Preferably, the first anode sublayer may comprise or is composed of Ag, the second anode sublayer may comprise or is composed of ITO or IZO, and the third anode sublayer may comprise or is composed of ITO or IZO.

[0350] Preferably, the first anode sublayer may contain or be composed of Ag, the second anode sublayer may contain or be composed of ITO, and the third anode sublayer may contain or be composed of ITO.

[0351] Preferably, the transparent conductive oxides in the second and third anode sublayers can be the same.

[0352] According to one embodiment, the anode layer may include a first anode sublayer, a second anode sublayer, and a third anode sublayer. The first anode sublayer contains Ag or Au with a thickness of 100 nm to 150 nm. The second anode sublayer contains or is composed of a transparent conductive oxide with a thickness of 3 nm to 20 nm. The third anode sublayer contains or is composed of a transparent conductive oxide with a thickness of 3 nm to 20 nm.

[0353] It should be understood that the third anode layer is not part of the substrate.

[0354] Hole injection layer

[0355] Hole-injected layers (HILs) can be formed on the anode electrode via vacuum deposition, spin coating, printing, casting, slot die coating, and Langmuir-Blodgett (LB) deposition. When using vacuum deposition to form HILs, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. Generally, however, vacuum deposition conditions can include deposition temperatures ranging from 100°C to 500°C, and 10... -8 Up to 10 -3 The pressure was 1 Torr (1 Torr equals 133.322 Pa) and the deposition rate was 0.1 nm / s to 10 nm / s.

[0356] When spin coating or printing is used to form HILs, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0357] HILs can be formed from any compound commonly used to form HILs. Examples of compounds that can be used to form HILs include phthalocyanine compounds 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-ethidedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0358] HILs may contain or be composed of p-type dopants, and the p-type dopants may be selected from, but are not limited to, tetrafluorotetracyanoquinone dimethyl ether (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diethylenedipropylene nitrile) or 2,2',2''-(cyclopropane-1,2,3-triethylenedipropylene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). HILs may be selected from hole-transporting matrix compounds doped with p-type dopants. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc) with a HOMO level of approximately -5.2 eV; tetrafluorotetracyanoquinone dimethane (F4TCNQ) doped with a LUMO level of approximately -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV); α-NPD (N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; and α-NPD doped with 2,2'-(perfluoronaphthyl-2,6-diethylenediamine)dimalonitrile. The concentration of the p-type dopant can be selected from 1 wt% to 20 wt%, more preferably from 3 wt% to 10 wt%.

[0359] The thickness of the HIL can range from about 1 nm to about 100 nm, for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL can have excellent hole injection characteristics without substantially impairing the driving voltage.

[0360] Hole transport layer

[0361] According to one embodiment of the present invention, the organic electronic device may further include a hole transport layer, wherein the hole transport layer is disposed between the anode layer and the cathode layer, preferably disposed between the organic semiconductor layer and the cathode layer of the present invention.

[0362] Hole transport layers (HTLs) can be formed on hollow ink layers (HILs) via vacuum deposition, spin coating, slot die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When forming HTLs via vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for HTL formation. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0363] HTLs can be formed from any compound commonly used to form HTLs. For example, applicable compounds are disclosed in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which are incorporated herein by reference. Examples of compounds that can be used to form HTLs are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds, such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). In these compounds, TCTA can transport holes and inhibit exciton diffusion into the EML.

[0364] According to a preferred embodiment of the invention, the hole transport layer may comprise a substantially covalent matrix compound.

[0365] According to one embodiment of the present invention, the hole transport layer may contain a substantially covalent matrix compound that is the same as the substantially covalent matrix compound in the organic semiconductor layer of the present invention. Preferably, the hole transport layer may contain a compound of formula (IXa) or (IXb) that is the same as the compound of formula (IXa) or (IXb) in the organic semiconductor layer of the present invention.

[0366] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably in the range of about 10 nm to about 200 nm, further in the range of about 20 nm to about 190 nm, further in the range of about 40 nm to about 180 nm, further in the range of about 60 nm to about 170 nm, further in the range of about 80 nm to about 160 nm, further in the range of about 100 nm to about 160 nm, and further in the range of about 120 nm to about 140 nm. A preferred thickness of the HTL can be from 170 nm to 200 nm.

[0367] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without substantially damaging the driving voltage.

[0368] Electron blocking layer

[0369] The function of an electron blocking layer (EBL) is to prevent electrons from transferring from the emissive layer to the hole transport layer, thereby confining electrons within the emissive layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. Compared to the LUMO level of the hole transport layer, the LUMO level of the triarylamine compound is closer to the vacuum level. Compared to the HOMO level of the hole transport layer, the HOMO level of the electron blocking layer is further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0370] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0371] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. This allows for higher luminous efficiency in the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than that of the phosphorescent emitter in the adjacent emitting layer. EP 2 722 908 A1 describes compounds suitable for triplet control layers, particularly triarylamine compounds.

[0372] Photoactive Alpha Layer (PAL)

[0373] The photoactive layer converts electric current into photons or photons into electric current.

[0374] PAL can be formed on HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming PAL using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming HIL. However, the deposition and coating conditions can vary depending on the compound used to form PAL.

[0375] The photoactive layer may not contain the compound of formula (I).

[0376] The photoactive layer can be a light-emitting layer (EML), also known as a light-emitting layer or a light-absorbing layer.

[0377] Emissive Layer (EML)

[0378] According to one embodiment, the organic electronic device of the present invention may further include a light-emitting layer (EML), wherein the light-emitting layer is disposed between an anode layer and a cathode layer, preferably, the light-emitting layer is disposed between an organic semiconductor layer and a cathode layer.

[0379] EML can be formed on HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming EML using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming HIL. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0380] The emissive layer (EML) may comprise an organic light-emitting body and a light-emitting compound dopant. Examples of organic light-emitting bodies are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), stilbene arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0381] The luminescent dopant can be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and those emitting light via thermally activated delayed fluorescence (TADF) are preferred due to their higher efficiency. The luminescent material can be a small molecule or a polymer.

[0382] Examples of red-emitting dopants include PtOEP, Ir(piq)3, and Btp2lr(acac), but are not limited to these. These compounds are phosphorescent; however, fluorescent red-emitting dopants can also be used.

[0383] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3.

[0384] Examples of phosphorescent blue emitting electron dopants are F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃, as well as terfluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0385] The luminescent layer may not contain the compound of formula (I).

[0386] Based on 100 parts by weight of the host, the amount of luminescent dopant can range from about 0.01 parts by weight to about 50 parts by weight. Alternatively, the luminescent layer can be composed of a luminescent polymer. The EML can 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 can exhibit excellent luminescence without substantially impairing the driving voltage.

[0387] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (X): (X), in Z 1 Z 2 and Z 3 They may be the same as or different from each other, and each is independently selected from monocyclic to polycyclic aromatic hydrocarbon rings or monocyclic to polycyclic aromatic heterocycles; Ar 31 and Ar 32 They may be identical or different from each other, and each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or adjacent substituents are bonded to each other to form substituted or unsubstituted aromatic rings or substituted or unsubstituted aliphatic rings. One or more of the substituents are selected from deuterium, alkyl groups having 1 to 6 carbon atoms, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 50 carbon atoms, alkylamine groups having 1 to 30 carbon atoms, alkylarylamine groups having 1 to 50 carbon atoms, arylamine groups having 6 to 50 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 2 to 30 carbon atoms, or substituents connected to two or more substituents selected from the above substituents, or adjacent substituents bonded to each other to form an unsubstituted or substituted aliphatic hydrocarbon ring having 3 to 60 carbon atoms; r 31 r 32 and r 33 Each is an integer of 0, 1, 2, 3, or 4, and when r 31 to r 33 When the number is 2 or greater, the substituents within the parentheses may be the same or different from each other.

[0388] According to one implementation, for equation (IX): Z 1 Z 2 and Z 3 They may be the same as each other or chosen to be different, and each is independently selected from monocyclic to bicyclic aromatic hydrocarbon rings or monocyclic to bicyclic aromatic heterocycles containing O, N or S; Ar 31 and Ar 32The same or different, and each independently selected from unsubstituted or aryl-substituted alkyl groups having 1 to 10 carbon atoms, unsubstituted or aryl-substituted aryl groups having 6 to 30 carbon atoms, or heteroaryl groups having 2 to 30 carbon atoms. R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups.

[0389] According to one implementation, for equation (IX): Z 1 Z 2 and Z 3 They may be identical to each other or chosen to be different, and each is independently selected from a benzene ring or a thiophene ring; Ar 31 and Ar 32 They may be the same as or different from each other, and each is independently selected from phenyl groups, biphenyl groups, naphthyl groups, dimethylfluorenyl groups, diphenylfluorenyl groups, dibenzofuran groups, or dibenzothiophene groups; R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms, substituted or unsubstituted silyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0390] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (X), said light-emitting compound being selected from formulas (BD1) to (BD9): (BD1) (BD2) (BD3) (BD4) (BD5) (BD6) (BD7) (BD8) (BD9)

[0391] According to a preferred embodiment of the present invention, the light-emitting layer comprises an organic light-emitting host compound, wherein the organic light-emitting host compound comprises

[0392] - At least one condensed aromatic ring system consisting of 3 to 5 rings, and

[0393] - 3 to 7 aromatic or heteroaromatic rings, wherein one or more daughter groups of the aromatic and / or heteroaromatic rings can condense to form a fused aromatic or heteroaromatic ring system; The molecular weight (Mw) of the organic light-emitting host compound is in the range of ≥ 400 g / mol but ≤ 2000 g / mol.

[0394] According to a preferred embodiment of the present invention, the organic light-emitting host compound has the formula (XI). (XI), where Ar 41 and Ar 42 Independently selected from substituted or unsubstituted C6 to C6. 24 Aryl, substituted or unsubstituted C3 to C 24 Mixed aromatics; L 41 and L 42 Independently selected from direct bonds or substituted or unsubstituted C6 to C1 bonds. 24 Aranediol, substituted or unsubstituted C3 to C4 24 Mixed aromatic subunits; R 41 To R 48 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatics; in Ar 41 Ar 42 L 41 L 42 R 41 To R 48 The substituents on the surface are independently selected from D, C6 to C6. 10 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 C 16 Alkyl, partially or perfluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, F or CN.

[0395] According to a preferred embodiment of the present invention, the organic light-emitting body and / or the compound of formula (XI) are selected from formulas (BH1) to (BH13): (BH1) (BH2) (BH3) (BH4) (BH5) (BH6) (BH7) (BH8) (BH9) (BH10) (BH11) (BH12) (BH13).

[0396] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI).

[0397] 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 light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI). 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 light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer.

[0398] 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 light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI). 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 light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer. The anode layer may include a first anode sublayer, a second anode sublayer, and a third anode sublayer. The first anode sublayer contains Ag or Au with a thickness of 100 nm to 150 nm. The second anode sublayer contains or is composed of a transparent conductive oxide with a thickness of 3 nm to 20 nm. The third anode sublayer contains or is composed of a transparent conductive oxide with a thickness of 3 nm to 20 nm. Preferably, the transparent conductive oxide is selected from ITO or IZO.

[0399] Hole blocking layer (HBL)

[0400] Hole blocking layers (HBLs) can be formed on the EML using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, and LB deposition to prevent holes from diffusing into the ETL. When the EML contains phosphorescent dopants, the HBL can also have triplet exciton blocking functionality.

[0401] HBL can also be called auxiliary ETL or a-ETL.

[0402] When forming HBLs using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds used to form HBLs include diazole derivatives, triazole derivatives, phenanthroline derivatives, and triazine derivatives.

[0403] The thickness of the HBL can 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 can have excellent hole blocking characteristics without substantially impairing the driving voltage.

[0404] Electron Transport Layer (ETL)

[0405] The organic electronic device according to the present invention may further include an electron transport layer (ETL), wherein the electron transport layer is disposed between the anode layer and the cathode layer, preferably between the organic semiconductor layer and the cathode layer.

[0406] According to another embodiment of the invention, the electron transport layer may further comprise an azazine compound, preferably a triazine compound.

[0407] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0408] The thickness of the ETL can range from about 15 nm to about 50 nm, for example, from about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL can have satisfactory electron injection characteristics without substantially impairing the driving voltage.

[0409] According to another embodiment of the present invention, the organic electronic device may further include a hole-blocking layer and an electron transport layer, wherein the hole-blocking layer and the electron transport layer comprise an azazine compound. Preferably, the azazine compound is a triazine compound.

[0410] Electron Injection Layer (EIL)

[0411] On the ETL, preferably directly on the electron transport layer, an optional EIL that facilitates electron injection from the cathode can be formed. Examples of materials used to form the EIL include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0412] The thickness of the EIL can range from about 0.1 nm to about 10 nm, for example, from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have satisfactory electron injection characteristics without substantially impairing the driving voltage.

[0413] cathode layer

[0414] The cathode layer is formed on an ETL or optionally an EIL. The cathode layer can be formed of a metal, alloy, conductive compound, or a mixture thereof. The cathode layer can have a low work function. For example, the cathode layer can 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), etc. Alternatively, the cathode layer can be formed of a transparent conductive oxide such as ITO or IZO.

[0415] The thickness of the cathode layer can be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, the cathode layer can be transparent or translucent even if it is formed of metal or metal alloy.

[0416] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0417] Organic light-emitting diode (OLED)

[0418] The organic electronic device according to the present invention can be an organic light-emitting device.

[0419] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided, the 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, a light-emitting layer, an electron transport layer, and a cathode layer.

[0420] According to another aspect of the present invention, an OLED is provided, the 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, a light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode layer.

[0421] According to another aspect of the present invention, an OLED is provided, the 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, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode layer.

[0422] According to various embodiments of the present invention, OLED layers can be provided disposed between the aforementioned layers, on a substrate, or on a top layer.

[0423] Organic electronic devices

[0424] The organic electronic device according to the present invention can be a light-emitting device or a photovoltaic cell, preferably a light-emitting device.

[0425] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method using: - At least one sedimentary source, preferably two sedimentary sources, more preferably at least three sedimentary sources.

[0426] Suitable deposition methods include: - Deposition via vacuum thermal evaporation; - Deposition via solution processing, preferably the processing being selected from spin coating, printing, casting; and / or - Slit-type die coating.

[0427] According to various embodiments of the present invention, a method is provided, the method using: - A first deposition source for releasing the compound of formula (I) according to the invention, and - A second deposition source for releasing essentially covalent matrix compounds; The method includes the step of forming an organic semiconductor layer; wherein, for organic light-emitting diodes (OLEDs): An organic semiconductor layer is formed by releasing a compound of formula (I) according to the invention from a first deposition source and a substantially covalent matrix compound from a second deposition source.

[0428] According to various embodiments of the present invention, the method may further include forming at least one layer selected from the group consisting of forming a hole transport layer or forming a hole blocking layer on the anode layer, and a light-emitting layer between the anode layer and the first electron transport layer.

[0429] According to various embodiments of the present invention, the method may further include the step of forming an organic light-emitting diode (OLED), wherein

[0430] - Form an anode layer on the substrate. - An organic semiconductor layer comprising a compound of formula (I) is formed on the anode layer. - A hole transport layer is formed on an organic semiconductor layer containing a compound of formula (I). - Form a light-emitting layer on the hole transport layer. - An electron transport layer is formed on the light-emitting layer, and optionally a hole blocking layer is formed on the light-emitting layer. - and finally the cathode layer is formed. - An optional hole-blocking layer is formed sequentially between the first anode layer and the light-emitting layer. - An optional electron injection layer is formed between the electron transport layer and the cathode layer.

[0431] According to various embodiments, an OLED may have the following layer structure, wherein the layers have the following order: The anode layer, an organic semiconductor layer comprising a compound according to formula (I) of the present invention, a first hole transport layer, a second hole transport layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode layer.

[0432] According to another aspect of the present invention, an electronic device is provided, the electronic device comprising at least one organic light-emitting device according to any embodiment described throughout this application, preferably, the electronic device comprising an organic light-emitting diode as described throughout this application. More preferably, the electronic device is a display device.

[0433] The embodiments will be described in more detail below with reference to examples. However, the invention is not limited to the following embodiments. Exemplary aspects will now be described in detail. Attached Figure Description

[0434] The aforementioned components in the described embodiments, as well as the claimed components and the components to be used according to the invention, have no particular exceptions in terms of their size, shape, material selection, and technical concept, and therefore selection criteria known in the relevant field can be applied without restriction.

[0435] Further details, features, and advantages of the invention are disclosed in the dependent claims and the following description of the accompanying drawings, which illustrate preferred embodiments of the invention by way of example. However, any embodiment is not necessarily representative of the full scope of the invention, and therefore the scope of the invention is to be interpreted with reference to the claims and this document. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and are intended to provide further explanation of the claimed invention.

[0436] Figure 1 This is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention; Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 4 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 5 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 6 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention.

[0437] Figure 1 This is a schematic cross-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 (130) comprising a metal complex according to formula (I), a photoactive layer (PAL) (151), and a cathode layer (190).

[0438] Figure 2 This is a schematic cross-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 (130) comprising a metal complex according to formula (I), an emissive layer (EML) (150), and a cathode layer (190).

[0439] Figure 3 This is a schematic cross-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 (130) comprising a metal complex according to formula (I), a hole transport layer (HTL) (140), an emissive layer (EML) (150), an electron transport layer (ETL) (160), and a cathode layer (190).

[0440] Figure 4 This is a schematic cross-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 (130) comprising a metal complex according to formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting 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).

[0441] Figure 5 This is a schematic cross-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) including a first anode sublayer (121) and a second anode sublayer (122), a hole injection layer (130) including a metal complex according to formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190).

[0442] Figure 6 This is a schematic cross-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) including a first anode sublayer (121), a second anode sublayer (122), and a third anode sublayer (123), a hole injection layer (130) including a metal complex according to formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190). The layers are arranged in exactly the order mentioned above.

[0443] In the above description, the method of manufacturing the organic electronic device 101 of the present invention, for example, begins with a substrate (110), on which an anode layer (120) is formed, and on the anode layer (120) a hole injection layer (130) comprising a metal complex according to formula (I), a photoactive layer (151), and a cathode electrode 190 are formed, either in exactly this order or in exactly the reverse order.

[0444] In the above description, the method of manufacturing the OLED of the present invention, for example, begins with a substrate (110), on which an anode layer (120) is formed, and on the anode layer (120) a hole injection layer (130) comprising a metal complex according to formula (I), an optional hole transport layer (140), an optional electron blocking layer (145), a light emitting layer (150), an optional hole blocking layer (155), an optional electron transport layer (160), an optional electron injection layer (180), and a cathode electrode 190 are formed, either entirely in this order or entirely in the reverse order.

[0445] A semiconductor layer (130) containing a metal complex according to formula (I) can be a hole injection layer.

[0446] although Figure 1 , Figure 2 , Figure 3 , Figure 4 , Figure 5 and Figure 6 Not shown, but a capping layer and / or sealing layer may also be formed on the cathode electrode 190 to seal the OLED 100. Furthermore, various other modifications may be made thereto.

[0447] One or more exemplary embodiments of the present invention will be described in detail below 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.

[0448] Calculated HOMO and LUMO

[0449] The highest occupied molecular orbital (HOMO) level, lowest unoccupied molecular orbital (LUMO) level, and dipole moment (μ) of the compounds and comparative compounds of Equation (I) were calculated using the packages ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany). The LUMO levels and dipole moments of the molecular structures were determined by applying the hybrid functionals B3LYP and Def2-TZVP basis sets, along with the Stuttgart / Dresden (SDD) effective nuclear potential (ECP) for the metals. All calculations were performed in the gas phase. If more than one conformation is feasible, the conformation with the lowest total energy is chosen. Different degrees of multiplicity can be applied depending on the metal cation. For the following metal cations, the multiplicity is shown in parentheses: Cu 2+ (doublet state), Mn 2+ (Sixtet). Unless otherwise noted, the HOMO, LUMO, and dipole moment values ​​in Table 1 are calculated using this method.

[0450] General method for determining the thin-film resistivity of the hole injection layer

[0451] The sheet resistance of the hole injection layer is also called "2L-Rs", which is measured in gigaohms per square (GΩ / sq).

[0452] The sheet resistance Rs can be determined by the transfer length method. Measurements can be performed using methods known in the art or as described in WO2022263524 A1.

[0453] For the embodiments and comparative examples according to the present invention in Table 3, the Rs of the hole injection layer (HIL) were determined as follows: In the first step, a device comprising a hole transport layer and a hole injection layer is fabricated, wherein the hole injection layer is deposited directly on the electrode and the hole transport layer is deposited directly on the hole injection layer.

[0454] - In the second step, the sheet resistance Rs of each device is determined by using the transfer length method.

[0455] The higher the resistance of the thin film, the lower the current between adjacent pixels. This allows individual pixels in an electronic device to be addressed without causing adjacent pixels to emit light. Consequently, so-called pixel crosstalk is reduced.

[0456] The sheet resistance of OLEDs, also known as "OLED-Rs", is measured in gigaohms per square (GΩ / sq).

[0457] The sheet resistance Rs can be determined by the transfer length method. Measurements can be performed using methods known in the art or as described in WO2022263524 A1.

[0458] For the embodiments and comparative examples according to the present invention in Table 7, OLED-Rs were measured as follows: In the first step, a complete OLED is deposited as described in the Examples and Comparative Examples.

[0459] In the second step, the sheet resistance Rs of each device was measured using the transfer length method without connecting the cathode.

[0460] The higher the resistance of the thin film, the lower the current between adjacent pixels. This allows individual pixels in an electronic device to be addressed without causing adjacent pixels to emit light. Consequently, so-called pixel crosstalk is reduced.

[0461] Glass transition temperature

[0462] As described in DIN EN ISO 11357 published in March 2010, the glass transition temperature (Tg) is measured in a Mettler Toledo DSC 822e differential scanning calorimeter under nitrogen atmosphere and with a heating rate of 10 K per minute.

[0463] Melting point (mp)

[0464] The melting point (mp) temperature was measured by DSC at a heating rate of 10 K / min, and the reported value corresponds to the peak temperature of the melting endothermic reaction observed on the DSC curve.

[0465] Thermogravimetric analysis

[0466] The term "TGA5%" refers to the temperature at which a 5% weight loss occurs during thermogravimetric analysis, and is measured in °C.

[0467] The TGA 5% value can be determined by heating a 9 mg–11 mg sample in an open 100 μL aluminum dish at a heating rate of 10 K / min in the equilibrium zone under a nitrogen flow of 20 mL / min and in the oven zone under a nitrogen flow of 30 mL / min.

[0468] The TGA 5% value provides an indirect measure of a compound's volatility and / or decomposition temperature. In first-order approximation, a higher TGA 5% value indicates lower volatility and / or a higher decomposition temperature.

[0469] Standard starting temperature

[0470] The standard onset temperature (T) was determined by loading 100 mg of the compound into a VTE source. RO As a VTE source, a point source for organic materials supplied by Kurt J. Lesker (www.lesker.com) or CreaPhys Ltd. (http: / / www.creaphys.com) can be used. (The last part, "in less than 10," appears to be an unrelated fragment and is omitted from the translation.) -5 The VTE source was heated at a constant rate of 15 K / min under millibar pressure, and the internal temperature of the source was measured using thermocouples. The evaporation of the compound was detected using a QCM detector, which detects the deposition of the compound on a quartz crystal of the detector. The deposition rate on the quartz crystal was measured in angstroms per second. To determine the standard onset temperature, the deposition rate was plotted against the VTE source temperature. The standard onset temperature is the temperature at which a significant deposition occurs on the QCM detector. For accurate results, the VTE source was heated and cooled three times, and only the results from the second and third runs were used to determine the standard onset temperature.

[0471] To achieve good control over the evaporation rate of organic compounds, a standard onset temperature can be in the range of 170°C to 280°C. If the standard onset temperature is below 170°C, evaporation can be too rapid and therefore difficult to control. If the standard onset temperature is above 280°C, the evaporation rate can be too low, which can lead to a low cycle time and, due to prolonged exposure to the elevated temperature, cause decomposition of the organic compounds in the VTE source.

[0472] The standard onset temperature is an indirect measure of a compound's volatility. The higher the standard onset temperature, the lower the compound's volatility.

[0473] Synthesis Examples

[0474] General procedure: Prepare substituted pyrazolone derivatives according to the reported procedure [see, 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; WO 2024033322].

[0475] General procedure for synthesizing acylpyrazolone derivatives: Under a nitrogen atmosphere, 2 equivalents of calcium hydroxide were added to 1 equivalent of pyrazolone in 1,4-dimethylbenzene. The suspension was cooled using a water bath, and 1 equivalent of acyl chloride was added in portions, with the mixture stirred overnight. The mixture was cooled using an ice bath, and then 2 N hydrochloric acid was added. The resulting suspension was filtered, and the crude product was washed with water, dried under vacuum, and further purified by sublimation to obtain a product as a pale yellow solid in quantitative yield.

[0476] General procedure for synthesizing zinc(II) complexes: Two equivalents of acylpyrazolone were dissolved in ethanol, and one equivalent of manganese(II) acetate tetrahydrate was added. The resulting mixture was stirred overnight at room temperature. The solution was then cooled in an ice bath, and a precipitate formed. The precipitate was then filtered, washed with ethanol and hexane, and dried under vacuum to obtain the desired product as a yellow powder in quantitative yield. The final product was further purified by sublimation.

[0477] General procedures for manufacturing OLEDs

[0478] For the inventive and comparative examples in Table 3, a glass substrate having an anode layer comprising a first anode sublayer of 120 nm Ag, a second anode sublayer of 8 nm ITO, and a third anode sublayer of 10 nm ITO was cut to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was performed to prepare the anode layer. The plasma treatment was performed in an atmosphere containing 98.4 vol% nitrogen and 1.6 vol% oxygen.

[0479] Then, 4 vol% of a metal complex of a compound of formula (I) or a comparative compound and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine ([1607480-22-7]) as a matrix compound were co-deposited on the anode layer in a vacuum to form a hole injection layer (HIL) with a thickness of 10 nm. The composition of the HIL is shown in Table 3.

[0480] Then, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine ([1607480-22-7]) was vacuum deposited on the HIL to form an HTL with a thickness of 128 nm. The compound used to form the HTL was chosen to be the same as the matrix compound in the HIL.

[0481] Then, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine ([1464822-27-2]) was vacuum deposited on HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0482] Then, a light-emitting layer (EML) with a thickness of 20 nm was formed on the EBL by co-depositing 99 vol% of 7-(phenyl-d5)-1-(10-(phenyl-d5)anthracene-9-yl)dibenzo[b,d]furan ([2457172-82-4]) as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] ([2482607-57-6]).

[0483] Then, a hole blocking layer (HBL) with a thickness of 5 nm was formed on the EML by depositing 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine ([1955546-40-3]).

[0484] Then, an electron transport layer (ETL) with a thickness of 31 nm was formed on the hole blocking layer by vacuum deposition of 50 wt% of 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) ([2244287-14-5]) and 50 wt% of LiQ (lithium 8-hydroxyquinoline) ([25387-93-3] or [850918-68-2]).

[0485] Then, an electron injection layer (EIL) is formed on the electron transport layer by vacuum deposition of a 1.3 nm Yb layer.

[0486] Then, in 10 -7 Ag:Mg (90 vol%:10 vol%) was evaporated at a rate of 0.01 Å / s to 1 Å / s under millibars to form a cathode layer with a thickness of 13 nm on the EIL.

[0487] Then, N-([1,1'-biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine ([1242056-42-3]) was deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0488] To evaluate the performance of the invention compared to the prior art, current efficiency was measured at 20°C. Using a Keithley 2635 source measurement unit, the current-voltage characteristics were determined by applying a voltage (in V) and measuring the current flowing through the device under test (in mA). The voltage applied to the device varied in 0.1 V steps within the range of 0 V to 10 V. Similarly, the luminance-voltage characteristics and CIE coordinates were determined by measuring the luminance (in cd / m²) at each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). The luminance-voltage and current-voltage characteristics at 15 mA / cm² were determined by interpolating the luminance-voltage and current-voltage characteristics separately. 2 The CD / A efficiency under these conditions.

[0489] In the bottom-emitting device, light emission is primarily Lambertian and is quantified as an external quantum efficiency (EQE) percentage. Light is emitted through the anode layer. To determine the efficiency (EQE) (in percentage), a calibrated photodiode at 15 mA / cm² is used. 2 The light output of the measuring device.

[0490] In top-emitting devices, light emission is forward-passing through the cathode layer, non-Lambertian, and highly dependent on the microcavity. Therefore, the efficiency EQE will be higher than that of bottom-emitting devices. To determine the efficiency EQE (in %), a calibrated photodiode was used at 15 mA / cm². 2 The light output of the measuring device.

[0491] The device lifetime LT was measured using a Keithley 2400 source meter under ambient conditions (20°C) and at 20 mA / cm², and recorded in hours.

[0492] The brightness of the device is measured using a calibrated photodiode. Lifetime LT is defined as the time until the brightness of the device drops to 97% of its initial value.

[0493] To determine the voltage stability over time U(100 h)-(1 h), a voltage of 20 mA / cm² was applied to the device. 2 The current density was measured. The operating voltage was measured after 1 hour and after 100 hours, and the voltage stability over the time period from 1 hour to 100 hours was calculated. A low value of U(100 h)-(1 h) indicates a lower increase in operating voltage over time, thus improving voltage stability.

[0494] Technical effects of the present invention

[0495] Data for the inventive and comparative examples are given in Table 1 below. Regarding Table 1, the comparative compounds CC1 to CC8 exhibit LUMO energy level values ​​in the range of -5.18 eV to -4.24 eV.

[0496] Compared to CC1 to CC8, the compounds of formula (I) depicted in Table 1 exhibit larger LUMO energy levels in the range of -3.74 eV to -1.81 eV.

[0497] A larger LUMO energy level can help increase the sheet resistance of organic semiconductor layers and / or organic electroluminescent devices. This can reduce crosstalk between two pixels in a display and improve the color purity or resolution of the display device.

[0498] Comparative compounds CC1 to CC8 exhibit an Egap (the energy difference between the LUMO and HOMO levels) in the range of 2.02 eV to 2.46 eV.

[0499] Compared to CC1 to CC9, the compounds of formula (I) in Table 1 exhibit a larger Egap in the range of 3.20 eV to 4.57 eV.

[0500] A larger Egap can reduce the absorption of visible light, for example, in organic light-emitting devices, which can improve current efficiency and / or external quantum efficiency.

[0501] Regarding Table 2, compounds CC1 to CC5 are compared to show melting points Tm in the range of 265°C to 299°C and standard onset temperatures T in the range of 141°C to 246°C. RO It has a glass transition temperature (Tg) as high as 126°C and a TGA5 in the range of 179°C to 219°C.

[0502] The compounds of formula (I) depicted in Table 2 exhibit higher melting points Tm in the range of 272°C to 367°C.

[0503] The compounds of formula (I) described in Table 2 exhibit a high standard onset temperature T in the range of 226°C to 266°C. RO .

[0504] Compared to CC1 to CC5, the compounds of formula (I) depicted in Table 2 exhibit higher glass transition temperatures (Tg) in the range of 137 °C to 170 °C.

[0505] The compounds of formula (I) depicted in Table 2 exhibit high TGA5 in the range of 339°C to 391°C.

[0506] A high melting point can be beneficial to processing stability; that is, if a linear source system is used, decomposition can be avoided and the risk of nozzle clogging can be reduced.

[0507] In the mass production of organic electronic devices, a high standard onset temperature is desirable for good control of the evaporation rate.

[0508] A high glass transition temperature is beneficial for increasing temperature stability during the baking process required in large-scale production. Furthermore, a high glass transition temperature can increase the stability of organic electronic devices, especially organic light-emitting devices.

[0509] A 5% increase in TGA could be desirable for improving thermal stability.

[0510] Table 3 shows the setup and data for organic electroluminescent devices containing an organic semiconductor layer of a compound or comparative compound of formula (I).

[0511] In Comparative Example 1, the organic semiconductor layer comprised 4 vol% of the comparative compound CC1 and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine. As shown in Table 3, the operating voltage was 3.44 V, the external quantum efficiency (Qeff or EQE) was 22.3%, the current efficiency (Ceff / CIE-y) was 232 cd / A, the lifetime LT97 was 95 h, and the voltage rise over time U(100 h)-U(1 h) was 0.04 V. Furthermore, the thin-film resistances OLED-Rs and 2L-Rs were 101 GΩ / sq and 33 GΩ / sq, respectively.

[0512] In Invention Example 1, the organic semiconductor layer comprises 4 vol% of the metal complex Al3 of formula (I) and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-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 98 h, which is an improvement over Comparative Example 1; and the voltage rise over time U(100 h)-U(1 h) is 0.06 V. Furthermore, the thin-film resistance OLED-Rs and 2L-Rs are 3580 GΩ / sq and 703 GΩ / sq, respectively, which are improvements over Comparative Example 1e.

[0513] In Invention Example 2, the organic semiconductor layer comprises 4 vol% of the metal complex A6 of formula (I) and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-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 116 h, an improvement over Comparative Example 1; and the voltage rise over time U(100 h)-U(1 h) is -0.02 V. Furthermore, the thin-film resistance OLED-Rs and 2L-Rs are 4482 GΩ / sq and 1262 GΩ / sq, respectively, an improvement over Comparative Example 1.

[0514] In Invention Example 4, the organic semiconductor layer comprises 4 vol% of the metal complex A4 of formula (I) and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-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 114 h, an improvement over Comparative Example 1; and the voltage rise over time U(100 h)-U(1 h) is 0.4 V. Furthermore, the thin-film resistance OLED-Rs and 2L-Rs are 1708 GΩ / sq and 224 GΩ / sq, respectively, an improvement over Comparative Example 1.

[0515] In Invention Example 4, the organic semiconductor layer comprises 4 vol% of the metal complex A9 of formula (I) and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-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 113 h, which is an improvement over Comparative Example 1; and the voltage rise over time U(100 h)-U(1 h) is 0.03 V. Furthermore, the sheet resistance 2L-Rs is 570 GΩ / sq, which is an improvement over Comparative Example 1.

[0516] In Invention Example 5, the organic semiconductor layer comprises 4 vol% of the metal complex A35 of formula (I) and 96 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine. The thin-film resistances OLED-Rs and 2L-Rs are 5005 GΩ / sq and 1724 GΩ / sq, respectively, which are improvements compared to Comparative Example 1.

[0517] In summary, significantly improved sheet resistance has been achieved without adverse effects on operating voltage, voltage rise over time, lifetime, current efficiency, and / or external quantum efficiency (Qeff or EQE).

[0518] Low operating voltage can be important for the low power consumption of organic electronic devices, especially mobile devices.

[0519] Long lifespan can lead to improved long-term stability of electronic devices.

[0520] A decrease in voltage over time can lead to an improvement in the long-term stability of electronic devices.

[0521] High efficiency can contribute to low power consumption in organic electronic devices, especially mobile devices.

[0522] Improving the resistance of the thin film can reduce pixel crosstalk. This, in turn, can improve the color purity of the display or the resolution of the monitor.

[0523] Table 1: LUMO level, Egap (difference between HOMO and LUMO levels), and dipole moment of compounds of formula (I) and comparative compounds.

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540] Table 2: Thermal properties of compounds of formula (I) and comparative compounds

[0541]

[0542]

[0543] Table 3: Setup, performance, and stability of organic electroluminescent devices and comparative examples

[0544]

[0545] The specific combinations of elements and features in the detailed embodiments described above are merely exemplary; these teachings are also explicitly considered in exchange for and substitution with other teachings herein and in the patents / applications incorporated herein by reference. As will be appreciated by those skilled in the art, variations, modifications, and other embodiments of the content described herein can be conceived without departing from the spirit and scope of the claimed invention. Therefore, the above description is by way of example only and is not intended to be limiting. In the claims, the word “comprising” does not exclude other elements or steps, and the singular forms “a” or “an” do not exclude plural indicators. The fact that specific measures are recited in different dependent claims does not mean that combinations of these measures cannot be used advantageously. The scope of the invention is defined by the claims and their equivalents. Furthermore, the reference numerals used in the specification and claims do not limit the scope of the claimed invention.

Claims

1. A compound of formula (I): ZnL2(AL) m (I) Where Zn is in the oxidized state Zn(II), L is the ligand of formula (II) (II) Where R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics; Where R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; Wherein L comprises at least one aryl or heteroaryl group containing at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded; AL is an auxiliary ligand that coordinates with metal M; Where m is an integer selected from 0 to 2.

2. The compound according to claim 1, wherein ligands of formula (II) according to the following table are excluded: 。 3. The compound according to claim 1 or 2, wherein in ligand L, R 1 R 2 and R 3 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

4. The compound according to any one of claims 1 to 3, wherein in ligand L, R 1 and R 2 At least one of them is selected from aryl or heteroaryl groups comprising at least three F groups, wherein the F groups are sp[i] with the ring of the aryl or heteroaryl group. 2 - Hybridized carbon atoms are directly bonded.

5. The compound according to any one of claims 1 to 4, wherein the molecular mass of L is selected in the range of ≤ 600 Da but ≥ 176 Da.

6. The compound according to any one of claims 1 to 5, wherein R 1 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics, Where R 1 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aromatics, Where R 2 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2; R here 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, Where R 3 One or more substituents are independently selected from D, F, CN, NO2, and unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, or CFD2.

7. The compound according to any one of claims 1 to 6, wherein the substituted or unsubstituted C6 to C6... 19 Aryl groups and the substituted or unsubstituted C2 to C3 groups 20 The heteroaryl group is selected from formulas (III) and (IV). (III), (IV), in X 1 Selected from N or CR 4 ; X 2 Selected from N or CR 5 ; X 3 Selected from N or CR 6 ; X 4 Selected from N or CR 7 ; X 5 Selected from N or CR 8 ; in X 1’ Selected from N or CR 9 ; X 2’ Selected from N or CR 10 ; X 3’ Selected from N or CR 11 ; X 4’ Selected from N or CR 12 ; X 5’ Selected from N or CR 13 ; Where R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 and R 13 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C2. 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD or CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Mixed aryl groups, F, CN, or NO2.

8. The compound according to any one of claims 1 to 7, wherein R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, R 1 Selected from equation (III), and R 2 Selected from formula (IV), CH3, CF3 and CF2H.

9. The compound according to any one of claims 1 to 8, wherein R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl, CN or NO2, R 1 Selected from equation (III), and R 2 Selected from formula (IV).

10. The compound according to any one of claims 1 to 9, wherein R 3 Selected from CH3, CF3 and CF2H, R 1 Selected from equation (III), and R 2 Selected from formula (IV), CH3, CF3 and CF2H.

11. The compound according to any one of claims 1 to 10, wherein R 1 Selected from substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 heteroaryl; R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

12. The compound according to any one of claims 1 to 11, wherein R 1 Selected from formula (III); R 2 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2; and R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, CH3, CH2D, CHD2, CD3, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, CF2H, CF2D, CFH2, CFHD, CFD2, CN.

13. The compound according to any one of claims 1 to 12, wherein R 1 Selected from equation (III), and R 2 Selected from CH3, CF3 and CF2H, and R 3 Selected from CH3, CF3, CF2H, and CN.

14. The compound according to any one of claims 1 to 13, wherein R 1 R 2 R 3 At least one of them is selected from equation (III), and where X 1 X 2 X 3 X 4 and X 5 At least three of them are selected from CF.

15. The compound according to any one of claims 1 to 14, wherein R 3 Selected from CH3, CF3 and CF2H.

16. The compound according to any one of claims 1 to 15, wherein R 1 R 2 and R 3 At least one of them is independently selected from F1 to F25: F1、 F2、 F3、 F4、 F5、 F6、 F7、 F8、 F9、 F10、 F11、 F12、 F13、 F14、 F15、 F16、 F17、 F18、 F19、 F20、 F21、 F22、 F23、 F24、 F25.

17. The compound according to any one of claims 1 to 16, wherein the compound is selected from formulas A1 to A60, B1 to B12, C1 to C7, and D1 to D23: A1、 A2、 A3、 A4、 A5、 A6、 A7、 A8、 A9、 A10、 A11、 A12、 A13、 A14、 A15、 A16、 A17、 A18、 A19、 A20、 A21、 A22、 A23、 A24、 A25、 A26、 A27、 A28、 A29、 A30、 A31、 A32、 A33、 A34、 A35、 A36、 A37、 A38、 A39、 A40ぁ A41、 A42ぁ A43ぁ A44ぁ A45ぁ A46、 A47、 A48ぁ A49ぁ A50ぁ A51ぁ A52ぁ A53ぁ A54ぁ A55ぁ A56、 A57ぁ A58ぁ A59ぁ A60、 B1、 B2、 B3、 B4、 B5、 B6、 B7、 B8、 B9、 B10、 B11、 B12、 C1、 C2、 C3、 C4、 C5、 C6、 C7、 D1、 D2、 D3、 D4、 D5、 D6、 D7、 D8、 D9、 D10、 D11、 D12、 D13、 D14、 D15、 D16、 D17、 D18、 D19、 D20、 D21、 D22、 D23。 18. The compound according to any one of claims 1 to 16, wherein the compound is selected from formulas A1, A2, A4 to A60, B1 to B12, C1 to C7, and D1 to D23.

19. Use of the compound of formula (I) according to any one of claims 1 to 18 in organic devices, especially organic electroluminescent devices.

20. Use of the compound of formula (I) according to any one of claims 1 to 19 as a p-type dopant.

21. An organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of formula (I) according to any one of 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 being disposed between the anode layer and the cathode layer.

23. The organic electronic device of 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 according to claim 22 or 23, wherein at least one organic semiconductor layer, which is the organic semiconductor layer according to claim 14, is a hole injection layer.

25. The organic electronic device according to any one of claims 22 to 24, wherein the organic electronic device is an electroluminescent device, an organic light-emitting diode (OLED), a light-emitting device, a 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 one of claims 22 to 25.

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