Organic electroluminescent materials and devices

Abstract

To provide a luminescent material in devices including electronic devices.SOLUTION: A compound comprising a ligand LA comprising a moiety L having a structure of Formula I is provided. In Formula I, LA is coordinated to a metal M; A1 is selected from B, N, P, P=O, P=S, Al, Ga, SiR", GeR", and SnR"; rings A, B, and C are 5- or 6-membered rings; Y1, Y2, and Y3 are selected from direct bonds, the metal M, and a variety of linkers; a+b+c=2 or 3; and one of a number of specific conditions is met. OLED devices, consumer products, and compositions comprising the compound are also provided.SELECTED DRAWING: None

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 63 / 106,035, filed October 27, 2020. This application is a continuation-in-part of U.S. Application No. 17 / 001,052, filed August 24, 2020, which claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 62 / 966,650, filed January 28, 2020, the disclosures of which are incorporated herein by reference in their entireties.

[0002] FIELD OF THE DISCLOSURE This disclosure relates generally to organometallic compounds and compositions and their various uses, including as light emitters in devices such as organic light emitting diodes and related electronic devices. [Background technology]

[0003] Optoelectronic devices that utilize organic materials are becoming increasingly desirable for a variety of reasons. Because many of the materials used to fabricate such devices are relatively inexpensive, organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as flexibility, may make them well suited for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials.

[0004] OLEDs utilize thin organic films that emit light when a voltage is applied across the device, and are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting, and backlighting.

[0005] One application of phosphorescent molecules is full-color displays. Industry standards for such displays require pixels adapted to emit specific colors, referred to as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. Conventionally, liquid crystal display emission from a white backlight is filtered with absorption filters to produce red, green, and blue emission. Similar techniques can be used with OLEDs. White OLEDs can be either single-emissive-layer (EML) devices or stacked structures. Color can be measured using CIE coordinates, which are well known in the art. Summary of the Invention

[0006] In one aspect, the present disclosure provides a compound of formula I: [ka] Ligand L comprising a moiety L having the structure A In formula I, a compound comprising: L A is coordinated to the metal M; A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; Rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Y 1 , Y 2 , and Y 3 are each independently a moiety selected from the group consisting of a direct bond, C═R, NR, O, S, Se, BR, SiRR′, GeRR′, SnRR′, and a metal M; a, b, and c are each independently 0 if not present and 1 if present; a+b+c=2 or 3; R A , R B , and R Ceach independently represent the maximum number of substitutions possible from mono to no substitution; R, R', R”, R A , R B , and R C are each independently a substituent selected from the group consisting of hydrogen, the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; M can coordinate with other ligands; Said ligand L A can be combined with other ligands to form bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligands; R, R', R”, R A , R B , and R C any two substituents in may be joined or fused to form a ring; and At least one of the following conditions is met: 1) at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring; 2) Y 1 , Y 2 , or Y 3 At least one of the exists as C=R; 3) A 1 is B and Y 1 , Y 2 , or Y 3 at least one of is present as a direct bond; 4) A 1 is B, a=b=1, and Y 1 Y 2 different from; 5) A 1 is N and Y 1 , Y 2 , and Y 3 At least one of these is present as a BR; 6)A 1 is B, a=b=1, and Y 1 is not O; 7) the compound contains a metal-carbene bond; or 8) Adjacent R A , R B , or R C At least one pair of these is bonded to each other to form a fused moiety that is fused to ring A, ring B, or ring C, respectively, and includes one or more rings extending from said ring, and said fused moiety is directly coordinated to said metal M.

[0007] In another aspect, the disclosure provides compositions of the disclosed compounds.

[0008] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound of the present disclosure.

[0009] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of the present disclosure. [Brief explanation of the drawings]

[0010] [Figure 1] FIG. 1 shows an organic light-emitting device.

[0011] [Figure 2] FIG. 2 shows an inverted organic light-emitting device that does not have a separate electron transport layer. DETAILED DESCRIPTION OF THE INVENTION

[0012] A. Terminology Unless otherwise stated, the following terms used herein are defined as follows:

[0013] As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" can actually be quite large. Small molecules can contain repeating units in some circumstances. For example, using a long-chain alkyl group as a substituent does not remove a molecule from the "small molecule" class. Small molecules can be incorporated into polymers, for example, as pendant groups on a polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of dendrimers, which consist of a series of chemical shells built on the core moiety. The core moiety of a dendrimer can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and all dendrimers currently used in the field of OLEDs are considered to be small molecules.

[0014] As used herein, "top" means furthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as "disposed over" a second layer, the first layer is disposed further from the substrate. There may be other layers between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode may be described as "disposed over" an anode, even though there may be various organic layers in between.

[0015] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium, either in the form of a solution or suspension.

[0016] A ligand may be referred to as "photoactive" if it is considered to directly contribute to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" if it is considered not to contribute to the photoactive properties of the emissive material, although the ancillary ligand may modify the properties of the photoactive ligand.

[0017] As used herein, and as generally understood by those skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Because ionization potentials (IPs) are measured as negative energies relative to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower" HOMO or LUMO energy level.

[0018] As used herein, and as generally understood by those skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a "higher" work function is illustrated as being farther away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.

[0019] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0020] The term "acyl" refers to a substituted carbonyl group (C(O)-R s ) refers to

[0021] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R sor -C(O)-OR s ) group.

[0022] The term "ether" means -OR s Refers to the base.

[0023] The terms "sulfanyl" and "thioether" are used interchangeably, and -SR s Refers to the base.

[0024] The term "sulfinyl" refers to -S(O)-R s Refers to the base.

[0025] The term "sulfonyl" means -SO2-R s Refers to the base.

[0026] The term "phosphino" refers to -P(R s ) refers to three groups, each R s may be the same or different.

[0027] The term "silyl" refers to -Si(R s ) refers to three groups, each R s may be the same or different.

[0028] The term "boryl" means -B(R s ) group or its Lewis adduct -B(R s ) 3 groups, R s may be the same or different.

[0029] In each of the above, R s can be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. sis selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0030] The term "alkyl" refers to and includes both straight-chain and branched-chain alkyl groups. Preferred alkyl groups contain from 1 to 15 carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, and 2,2-dimethylpropyl. Additionally, the alkyl groups may be optionally substituted.

[0031] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups contain 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Furthermore, the cycloalkyl groups may be optionally substituted.

[0032] The terms "heteroalkyl" or "heterocycloalkyl" refer to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Furthermore, the heteroalkyl or heterocycloalkyl group may be optionally substituted.

[0033] The term "alkenyl" refers to and includes both straight-chain and branched-chain alkene groups. An alkenyl group is essentially an alkyl group containing at least one carbon-carbon double bond in the alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group containing at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkenyl, cycloalkenyl, or heteroalkenyl group may be optionally substituted.

[0034] The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne groups. Alkynyl groups are essentially alkyl groups containing at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkynyl groups may be optionally substituted.

[0035] The terms "aralkyl" and "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. In addition, said aralkyl group may be optionally substituted.

[0036] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Heteroaromatic cyclic groups may be used interchangeably with heteroaryl. Preferred heteroaromatic cyclic groups contain 3 to 7 ring atoms and include at least one heteroatom, including cyclic amines such as morpholino, piperidino, and pyrrolidino, and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, and tetrahydrothiophene. Furthermore, the heterocyclic groups may be optionally substituted.

[0037] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycyclic ring can have two or more rings in which two carbon atoms are shared between two adjacent rings (the rings are "fused"), at least one of which is an aromatic hydrocarbyl group, and the other rings can be, for example, a cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups contain 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. Aryl groups having 6 carbons, 10 carbons, or 12 carbons are particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, and are preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Furthermore, the aryl group may be optionally substituted.

[0038] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems containing at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many instances, O, S, or N are preferred heteroatoms. Heteromonocyclic aromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings can have 1 to 6 heteroatoms. Heteropolycyclic ring systems can have two or more rings in which two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is heteroaryl; for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Heteropolycyclic aromatic ring systems can have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziso ... Examples of heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and their aza analogs. Furthermore, the heteroaryl group may be optionally substituted.

[0039] Of the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole groups, and their respective aza analogues, are of particular interest.

[0040] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic, aryl, and heteroaryl are independently unsubstituted or independently substituted with one or more common substituents.

[0041] In many instances, the common substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

[0042] In some instances, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.

[0043] In some instances, more preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

[0044] In still other instances, the most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0045] The terms "substituted" and "substituted" refer to a substituent other than H attached to the relevant position (e.g., carbon or nitrogen). For example, R 1 If represents a mono-substituted group, one R 1 must be other than H (i.e., a substitution). Similarly, R 1 If represents a di-substitution, R 1 must be other than H. Similarly, R 1 When represents zero or no substitution, R 1can be a hydrogen at an available valence of a ring atom, as in the case of a carbon atom in benzene and a nitrogen atom in pyrrole, or simply represent nothing in the case of a ring atom with a fully satisfied valence (e.g., nitrogen in pyridine). The maximum number of substitutions possible in a ring structure depends on the total number of available valences on the ring atoms.

[0046] As used herein, "combinations thereof" refers to one or more members of the applicable list being combined to form known or chemically stable configurations that one skilled in the art can contemplate from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. In one example, the term "substituted" includes combinations of 2 to 4 of the listed groups. In another example, the term "substituted" includes combinations of 2 to 3 groups. In yet another example, the term "substituted" includes combinations of 2 groups. Preferred combinations of substituents are those containing up to 50 atoms that are not hydrogen or deuterium, or those containing up to 40 atoms that are not hydrogen or deuterium, or those containing up to 30 atoms that are not hydrogen or deuterium. In many examples, preferred combinations of substituents include up to 20 atoms that are not hydrogen or deuterium.

[0047] The designation "aza" in the fragments described herein, such as aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C—H groups in each aromatic ring can be replaced by a nitrogen atom; for example, but not by way of limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Those skilled in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0048] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, International Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. 2011 / 0037057, the entire contents of which are incorporated by reference, describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Tetrahedron 2015, 71, 1425-30 (Ming Yan et al.) and Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65 (Atzrodt et al.), the entire contents of which are incorporated by reference, which describe efficient routes for deuteration of methylene hydrogens in benzylamines and substitution of aromatic ring hydrogens with deuterium, respectively.

[0049] It is understood that when a molecular fragment is described as being a substituent or as being attached to another moiety, the name may be described as being the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). Different designations of substituents or attached fragments are considered equivalent herein.

[0050] In some instances, adjacent pairs of substituents can be optionally bonded or fused to form a ring. Preferred rings are 5-, 6-, or 7-membered carbocyclic or heterocyclic rings, including both cases where the portion of the ring formed by the pair of substituents is saturated and cases where the portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two related substituents can be adjacent to each other on the same ring, or can be adjacent to each other on two rings with the two nearest available substitutable positions, such as the 2- and 2'-positions in biphenyl and the 1- and 8-positions in naphthalene, as long as a stable fused ring system can be formed.

[0051] B. Compounds of the Present Disclosure In one aspect, the present disclosure provides a compound of formula I: [ka] Ligand L comprising a moiety L having the structure A In the structure of Formula I, L A is coordinated to the metal M; A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; Rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Y 1 , Y 2 , and Y 3 are each independently a moiety selected from the group consisting of a direct bond, C═R, NR, O, S, Se, BR, SiRR′, GeRR′, SnRR′, and a metal M; a, b, and c are each independently 0 if not present and 1 if present; a+b+c=2 or 3; R A , R B , and R C each independently represent the maximum number of substitutions possible from mono to no substitution; R, R', R”, R A , R B , and R C are each independently hydrogen or a substituent selected from the group consisting of the metal M, the general substituents described herein, and combinations thereof; M can coordinate with other ligands; Said ligand L A can be combined with other ligands to form bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligands; R, R', R”, R A , R B , and R C any two substituents in may be joined or fused to form a ring; and At least one of the following conditions is met: 1) at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring; 2) Y 1 , Y 2 , or Y 3 At least one of the exists as C=R; 3) A 1 is B and Y 1 , Y 2 , or Y 3 at least one of is present as a direct bond; 4) A 1 is B, a=b=1, and Y 1 Y 2 different from; 5) A 1 is N and Y 1 , Y 2 , and Y 3 At least one of these is present as a BR; 6)A 1 is B, a=b=1, and Y 1 is not O; 7) the compound contains a metal-carbene bond; or 8) Adjacent R A , R B , or R C At least one pair of these is bonded to each other to form a fused moiety that is fused to ring A, ring B, or ring C, respectively, and includes one or more rings extending from said ring, and said fused moiety is directly coordinated to said metal M.

[0052] In some embodiments, two, three, four, or more of conditions 1) through 8) are met.

[0053] In some embodiments, the ligand L A is coordinated to the metal M via at least one metal-carbene bond.

[0054] In some embodiments, R, R', R", R A , R B , and R Care each independently hydrogen or a substituent selected from the group consisting of the metal M, the preferred general substituents defined herein, and combinations thereof. In some embodiments, R, R', R", R A , R B , and R C are each independently hydrogen or a substituent selected from the group consisting of the metal M, the more preferred general substituents defined herein, and combinations thereof. In some embodiments, R, R', R", R A , R B , and R C are each independently hydrogen or a substituent selected from the group consisting of the metal M, the most preferred general substituents defined herein, and combinations thereof.

[0055] In some embodiments, at most one of rings A, B, and C coordinates to the metal M. In some embodiments, none of rings A, B, and C coordinates to the metal M.

[0056] In some embodiments, the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au. In some embodiments, the metal M is Os or Ir. In some embodiments, the metal M is Pt or Pd. In some embodiments, the metal M is selected from the group consisting of Cu, Ag, and Au.

[0057] In some embodiments, at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring. In some embodiments, one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring. In some embodiments, two of rings A, B, and C are 5-membered carbocyclic or heterocyclic rings. In some embodiments, each of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring.

[0058] In some embodiments, Y 1 , Y 2 , and Y 3At least one of Y is present as C=R. 1 , Y 2 , and Y 3 is present as C=R. In some embodiments, Y 1 , Y 2 , and Y 3 In some embodiments, two of Y are present as C=R. 1 , Y 2 , and Y 3 Each of these exists as C=R. Y 1 , Y 2 , and Y 3 In some embodiments where at least one of is present as C=R, R is selected from R', R", R A , R B , or R C may be bonded to or fused with one of the following to form a ring.

[0059] In some embodiments, A 1 is B and Y 1 , Y 2 , and Y 3 In some embodiments, at least one of A is present as a direct bond. 1 is B and Y 1 , Y 2 , and Y 3 At least two of the following are present as direct bonds:

[0060] In some embodiments, A 1 is B, a=b=1, and Y 1 Y 2 In some embodiments, A 1 is B, a=b=1, and Y 1 Y 2 Unlike and Y 1 and Y 2 Both exist.

[0061] In some embodiments, A 1 is N and Y 1 , Y 2 , and Y3 At least one of A is present as BR. 1 is N and Y 1 , Y 2 , and Y 3 In some embodiments, two of A are present as BR. 1 is N and Y 1 , Y 2 , and Y 3 Each of these exists as a BR.

[0062] In some embodiments, A 1 is B, a=b=1, and Y 1 is not O.

[0063] In some embodiments, the compound comprises a metal-carbene bond. A is coordinated to M via a metal-carbene bond.

[0064] In some embodiments, adjacent R A , R B , or R C are bonded to each other to form a fused moiety comprising one or more rings fused to and extending from ring A, ring B, or ring C, respectively, and the fused moiety directly coordinates to the metal M. In some embodiments, the fused moiety comprises one 5- or 6-membered aromatic ring. In some embodiments, the fused moiety comprises two 5- or 6-membered aromatic rings. In some embodiments, the fused moiety comprises one 5-membered aromatic ring and one 6-membered aromatic ring. In some embodiments, the fused moiety comprises three 5- or 6-membered aromatic rings.

[0065] In some embodiments, exactly one substituent R A , R B , R C , R, or R' is the metal M.

[0066] In some embodiments, exactly one substituent RA , R B , or R C is the metal M.

[0067] In some embodiments, R A , R B , R C At least one of R, R, or R' comprises a substituent that coordinates to the metal M. In some embodiments, R A , R B , R C , R, or R' contains a substituent that coordinates to said metal M.

[0068] In some embodiments, R A , R B , R C At least one of R, R, or R' comprises a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl that coordinates to the metal M. In some embodiments, R A , R B , R C , R, or R' comprises a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl that coordinates to said metal M.

[0069] In some embodiments, R A , R B , R C , R, or R' is not the metal M.

[0070] In some embodiments, A 1 is B. In some embodiments, A 1 is N. In some embodiments, A 1 is P. In some embodiments, A 1 In some embodiments, A is P=O. 1 In some embodiments, P=S. 1 is Al. In some embodiments, A 1 is Ga. In some embodiments, A 1is SiR″. In some embodiments, A 1 is GeR″. In some embodiments, A 1 is SnR”.

[0071] In some embodiments, the moiety L has a structure selected from the group consisting of: [ka] [ka] During the ceremony, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , and X 19 are each independently C or N; R D and R E each independently represent the maximum number of substitutions possible from mono to no substitution; R D and R E each independently represents hydrogen or a substituent selected from the group consisting of the metal M, the general substituents defined herein, and combinations thereof; Y 4 , Y 5 , and Y 6 are each independently selected from the group consisting of C=R, NR, O, S, Se, BR, CRR', SiRR', GeRR', and SnRR'; and R, R', R”, R A , R B , R C , RD and R E Any two of the substituents in the formula (I) can be joined or fused to form a ring.

[0072] In some such embodiments, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , and X 19 The maximum number of consecutively bonded N atoms in is two.

[0073] In some embodiments, the moiety L has the structure of Formula III: [ka] During the ceremony, M is for X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , and Y 3 directly combine with one maximum number of; Y 1 , Y 2 , and Y 3 at least one of which is present as NR; X 1 , X 2 , and X 3 is directly bonded to said metal M, at least one of the following statements is met: 1) a+b+c=3; 2) a or c is 0; 3) b is 1; 4) R A contains a 5-membered carbocyclic or heterocyclic ring that coordinates to the metal M; or 5) X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , or Y 3 One of the groups contains R that contains a 5- or 6-membered carbocyclic or heterocyclic ring that coordinates to M.

[0074] In some embodiments of Formula III, two, three, or four of conditions 1) through 5) are met.

[0075] In some embodiments of Formula III, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , and X 9 are C, respectively.

[0076] In some embodiments of Formula III, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , and X 9 At least one of is N.

[0077] In some embodiments of Formula III, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , and X 9 Exactly one of is N.

[0078] In some embodiments of Formula III, Y 1 , Y 2 , and Y 3 At least one of the following is O.

[0079] In some embodiments of Formula III, Y 1 , Y 2 , and Y 3 At least one of is S.

[0080] In some embodiments of Formula III, Y 1 , Y 2 , and Y 3 At least two of the following are independently NR.

[0081] In some embodiments of Formula III, a+b+c is 2.

[0082] In some embodiments of Formula III, a+b+c is 3.

[0083] In some embodiments, the moiety L is part of a bidentate ligand. In some embodiments, the moiety L is part of a tridentate ligand. In some embodiments, the moiety L is part of a tetradentate ligand. In some embodiments, the moiety L is part of a pentadentate ligand. In some embodiments, the moiety L is part of a hexadentate ligand.

[0084] In some embodiments, M is Pt. In some embodiments, M is Ir.

[0085] In some embodiments, L A is a group L consisting of A Selected from the general structure: [ka] JPEG2025134732000007.jpg185160JPEG2025134732000008.jpg5538In formula, Rings F, G, and H are each independently a monocyclic or polycyclic ring structure, including 5- and / or 6-membered carbocyclic or heterocyclic rings; Ring T is a polycyclic ring structure containing the structure of formula I; L is a direct bond or a bivalent linker; Z 1 is C or N; X 20 , X 21 , X 22 , and X 23 are each independently C or N; The wavy line represents a bond to the metal M; R F , R G , and R H each independently represent the maximum number of substitutions possible from mono to no substitution; R F , R G , and R H are each independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; R, R', R”, R A , R B , R C , R D , R E , R F , R G , and R H Any two of the substituents in the formula (I) can be joined or fused to form a ring.

[0086] Some L A In an embodiment of the general structure, ring F, ring G, and ring H are each independently monocyclic or polycyclic ring structures containing 5- and / or 6-membered aromatic rings.

[0087] Some L A In an embodiment of the general structure of the formula (I), L is selected from the group consisting of optionally further substituted phenyl and biphenyl. AIn an embodiment of the general structure of the formula: L is a direct bond.

[0088] Some L A In an embodiment of the general structure of 1 is C. Some L A In an embodiment of the general structure of 1 is N.

[0089] Some L A In an embodiment of the general structure of A comprises a linker directly bonding to ring A, which is bonded to a second linker to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. In some embodiments, the linker is selected from the group consisting of O, S, and NR″, where R″ is hydrogen or a substituent selected from the group consisting of general substituents as defined herein.

[0090] In some embodiments, the ligand L A is selected from the group selected from the structures defined in List 1 below. [ka] JPEG2025134732000010.jpg189160JPEG2025134732000011.jpg214160JPEG2025134732000012.jpg192160JPEG2025134732000013.jpg179160JPEG202 5134732000014.jpg180160JPEG2025134732000015.jpg227160JPEG2025134732000016.jpg203160JPEG2025134732000017.jpg215160JPEG2025134732 000018.jpg169160JPEG2025134732000019.jpg217160JPEG2025134732000020.jpg218160JPEG2025134732000021.jpg220160JPEG2025134732000022.jpg202160JPEG2025134732000023.jpg203160JPEG2025134732000024.jpg178160JPEG2025134732000025.jpg214160In the list, R1 to R307 are defined in List 2 below. [ka] JPEG2025134732000027.jpg211160JPEG2025134732000028.jpg213160JPEG2025134732000029.jpg221160JPEG2025134732000030.jpg203160JPEG2025134732000031.jpg210160JPEG2025134732000032.jpg217160JPEG2025134732000033.jpg204160JPEG2025134732000034.jpg165160In the formula, Me is methyl, iPr is isopropyl, and tBu is t-butyl.

[0091] In some embodiments, the compound has the formula M(L A ) p (L B ) q (L C ) rL A is a bidentate ligand; L B and L C are each a bidentate ligand; p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M.

[0092] In some embodiments, the compound is Ir(L A )3, Ir(L A )(L B )2, Ir(L A )2(L B ), Ir(L A )2(L C ), and Ir(L A )(L B )(L C ) and L A , L B , and L C are different from each other.

[0093] In some embodiments, the compound has the formula Pt(L A )(L B ) and L A and L B may be the same or different. Pt(L A )(L B In some embodiments of A and L B combine to form a tetradentate ligand.

[0094] In some embodiments, L B and L C are each independently selected from the group consisting of: [ka] JPEG2025134732000036.jpg101160, Y T is selected from the group consisting of B, Al, Ga, and In; Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y 10 , Y11 , Y 12 , and Y 13 are each independently selected from the group consisting of carbon and nitrogen; Y' is BR e , N.R. e , PR e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , and GeR e R f selected from the group consisting of: R a , R b , R c , and R d each independently represents zero, mono, or up to the maximum number of substitutions allowed for its associated ring; R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f are each independently a substituent selected from the group consisting of hydrogen or deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and the general substituents defined herein; Any two adjacent R a , R a1 , R b , R b1 , R c , R c1 , R d , R d1 , R e , and R f can be fused or linked to form a ring or to form a multidentate ligand.

[0095] In some embodiments, L B and L C are each independently selected from the group consisting of: [ka] JPEG2025134732000038.jpg226160JPEG2025134732000039.jpg209160JPEG2025134732000040.jpg98160In formula, R a ', R b ', and R c each independently represents zero, mono, or up to the maximum number of substitutions allowed for its associated ring; R a1 , R b1 , R c1 , R a , R b , R c , R N , R a ', R b ', and R c each ' is independently a substituent selected from the group consisting of hydrogen or deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; R a ', R b ', and R c Two adjacent substituents in ' can be fused or linked to form a ring.

[0096] In some embodiments, the compound has the formula Ir(L Ax-(i)(l)(m)(n)(o))3, where x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; and the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))3~Ir(L A 64-(307)(307)(307)(307)(307))3, ​​or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))(L Bk )2, wherein x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; and k is an integer from 1 to 264; the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))(L B1 )2~Ir(L A 64-(307)(307)(307)(307)(307))(L B264 )2, or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))2(L Bk wherein x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; k is an integer from 1 to 264; and the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))2(L B1 )~Ir(L A 64-(307)(307)(307)(307)(307))2(L B264 ), or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))(L BBh )2, wherein x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; and h is an integer from 1 to 180; the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))(L BB1 )2~Ir(L A 64-(307)(307)(307)(307)(307))(LBB180 )2, or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))2(L BBh ), wherein x is an integer of 1 to 64; i, l, m, n, and o are each independently an integer of 1 to 307; h is an integer of 1 to 180; and the compound is selected from the group consisting of Ir(L A 1-(1)(1)(1)(1)(1))2(L BB1 )~Ir(L A 64-(307)(307)(307)(307)(307))2(L BB180 ), or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))2(L Cj-I wherein x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; and j is an integer from 1 to 1416; and the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))2(L C1-I )~Ir(L A 64-(307)(307)(307)(307)(307))2(L C1416-I ), or The compound has the formula Ir(L A x-(i)(l)(m)(n)(o))2(L Cj-II wherein x is an integer from 1 to 64; i, l, m, n, and o are each independently an integer from 1 to 307; and j is an integer from 1 to 1416; and the compound has the formula Ir(L A 1-(1)(1)(1)(1)(1))2(L C1-II )~Ir(L A 64-(307)(307)(307)(307)(307))2(L C1416-II ) selected from the group consisting of; L B1 ~L B264 has the structure defined in Listing 3 below. [ka] JPEG2025134732000042.jpg208160JPEG2025134732000043.jpg199160JPEG2025134732000044.jpg212160JPEG20251347320 00045.jpg215160JPEG2025134732000046.jpg200160JPEG2025134732000047.jpg197160JPEG2025134732000048.jpg150160L BB1 ~L BB180 has the structure defined in Listing 4 below. [ka] JPEG2025134732000050.jpg190160JPEG2025134732000051.jpg194160JPEG2025134732000052.jpg223160JPEG2025134732000 053.jpg193160JPEG2025134732000054.jpg209160JPEG2025134732000055.jpg218160JPEG2025134732000056.jpg136160Each L Cj-I is expressed by the following formula: [ka] having a structure based on; Each L Cj-II is expressed by the following formula: [ka] It has a structure based on L Cj-I and L Cj-II Each L in Cj In R 201 and R 202 are independently defined as shown in List 5 below. [ka] JPEG2025134732000060.jpg224160JPEG2025134732000061.jpg222160JPEG2025134732000062.jpg224160JPEG2025134732000 063.jpg223160JPEG2025134732000064.jpg223160JPEG2025134732000065.jpg224160JPEG2025134732000066.jpg103160In the formula, R D1 ~R D246 is defined in Listing 6 below. [ka] JPEG2025134732000068.jpg196160JPEG2025134732000069.jpg205160JPEG2025134732000070.jpg213160JPEG2025134732000071.jpg2536

[0097] In some embodiments, the compound has the formula Ir(L Ax -(i)(l)(m)(n)(o))(L Bk )2 or Ir(L Ax -(i)(l)(m)(n)(o))2(L Bk ), and the compound has the following structure: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B132 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B158 , L B160 , L B162 , L B204 , L B206, L B214 , L B216 , L B218 , L B220 , L B222 , L B231 , L B233 , L B235 , L B237 , L B240 , L B242 , L B244 , L B246 , L B248 , L B250 , L B252 , L B254 , L B256 , L B258 , L B260 , L B262 , L B263 , and L B264 L selected from the group consisting of Bk It has a ligand.

[0098] In some embodiments, the compound has the formula Ir(L Ax -(i)(l)(m)(n)(o))(L Bk )2 or Ir(L Ax -(i)(l)(m)(n)(o))2(L Bk ), and the compound has the following structure: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B132 , L B136 , L B138 , L B142 , L B156 , L B162 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , and L B237 L selected from the group consisting of Bk It has a ligand.

[0099] In some embodiments, the compound has the formula Ir(L Ax -(i)(l)(m)(n)(o))2(L Cj-I ) or Ir(L Ax -(i)(l)(m)(n)(o))2(L Cj-II ), and the compound has L Cj-I or L Cj-II It has a ligand, and its R 1’ and R 2’ are each independently selected from the following structures: D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D64 , R D18 , R D20 , R D22 , R D37 , R D40 , R D41 , R D42 , R D43 , R D48 , R D49 , R D50 , R D54 , R D55 , R D58 , R D59 , R D78 , R D79 , R D81 , R D87 , R D88 , R D89 , R D93 , R D116 , R D164 , R D118 , R D119 , R D120 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D147 , R D149 , R D151 , R D154 , R D155 , R D161 , R D645 , and R D190is selected from the group consisting of:

[0100] In some embodiments, the compound has the formula Ir(L Ax -(i)(l)(m)(n)(o))2(L Cj-I ) or Ir(L Ax -(i)(l)(m)(n)(o))2(L Cj-II ), and the compound has L Cj-I or L Cj-II It has a ligand, and its R 1’ and R 2’ are each independently selected from the following structures: D1 , R D3 , R D4 , R D5 , R D9 , R D64 , R D22 , R D43 , R D50 , R D78 , R D116 , R D118 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D149 , R D151 , R D154 , R D155 , and R D190 is selected from the group consisting of:

[0101] In some embodiments, the compound has the formula Ir(L Ax -(i)(l)(m)(n)(o))2(L Cj-I ), and the compound has L Cj-I Ligands, L Cj-I The ligand is selected from the group consisting of the following structures: [ka] JPEG2025134732000073.jpg165160

[0102] In some embodiments, the compound is selected from the group consisting of: [ka] JPEG2025134732000075.jpg223160JPEG2025134732000076.jpg53139

[0103] In some embodiments, the compound has the following formula II: [ka] It has the following structure. During the ceremony, Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from C or N; M 1 is Pd or Pt; Ring A 1 , A 2 , A 3 , and A 4 are each independently a monocyclic or polycyclic ring structure containing at least one 5- or 6-membered carbocyclic or heterocyclic ring; K 1 ~K 4 are each independently selected from the group consisting of a direct bond, O, and S; K 3 and K. 4 at least one of is a direct bond; L 1 ~L 4 are each independently selected from the group consisting of a single bond, no bond, O, S, C=R', CR'R'', SiR'R'', BR', BR'R'', and NR'; L 1 ~L 4 There are at least two of the following: R1 ’ , R2 ’ , R3 ’ , and R4 ’ each independently represents zero, mono, or up to the maximum number of substitutions allowed for its associated ring; R1’ , R2 ’ , R3 ’ , R4 ’ , R', and R" each independently represent hydrogen or a substituent selected from the group consisting of the general substituents defined herein; R1 ’ , R2 ’ , R3 ’ , R4 ’ any two of R', and R" can be bonded or fused together to form a ring; R1 ’ , R2 ’ , R3 ’ , R4 ’ , L 1 , L 2 , L 3 , L 4 , ring A 1 , ring A 2 , ring A 3 , ring A 4 or a combination thereof comprises the structure of Formula I:

[0104] In some embodiments of Formula II, A 1 , A 2 , A 3 , and A 4 are each independently a monocyclic or polycyclic aromatic ring structure. 1 , A 2 , A 3 , and A 4 are each independently selected from the group consisting of phenyl, pyridine, pyrazine, pyrimidine, pyridazine, imidazole, imidazole-derived carbenes, pyrazole, furan, thiophene, pyrrole, and benzo-fused variants thereof.

[0105] In some embodiments of Formula II, L 1 , L 2 , L 3 , and L 4 At least one of L is O. In some embodiments of Formula II, L 1 , L 2 , L 3 , and L4 In some embodiments of Formula II, at least one of L is NR'. 1 , L 2 , L 3 , and L 4 At least one of the is CR'R".

[0106] In some embodiments of Formula II, Z 1 , Z 2 , Z 3 , and Z 4 Two of them are C and Z 1 , Z 2 , Z 3 , and Z 4 and the remaining two are N. In some embodiments of Formula II, Z 1 , Z 2 , Z 3 , and Z 4 Two of them are C and Z 1 , Z 2 , Z 3 , and Z 4 One of them is carbene C, and Z 1 , Z 2 , Z 3 , and Z 4 The remaining one is N.

[0107] In some embodiments of Formula II, K 1 , K. 2 , K. 3 , and K 4 are both direct bonds. In some embodiments of Formula II, K 1 , K. 2 , K. 3 , and K 4 One of them is O.

[0108] In some embodiments of Formula II, the compound has a structure selected from the group consisting of: [ka] JPEG2025134732000079.jpg113160In formula, R A’ , RB’ , R C’ , R D’ , R E’ , R F’ , and R G’ are each independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , and R G’ any two substituents may be joined or fused to form a ring; R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , R G’ or combinations thereof, together with or apart from the remainder of formula II, comprises the structure of formula I.

[0109] In some embodiments of Formula II, the compound has a structure having a metal-carbene bond selected from the group consisting of: [ka] JPEG2025134732000081.jpg4096

[0110] In some embodiments, R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , R G’ In some embodiments, at least one of R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , R G’In some embodiments, at least one of R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , R G’ In some embodiments, at least one of R A’ , R B’ , R C’ , R D’ , R E’ , R F’ , R G’ At least one of the groups contains at least six six-membered aromatic rings that are not fused to one another.

[0111] In some embodiments, R A’ In some embodiments, R A’ In some embodiments, R A’ In some embodiments, R A’ contains at least six six-membered aromatic rings that are not fused to one another.

[0112] In some embodiments, the compound has the formula Pt(L A’ )(L B’ ), wherein the ligand L A’ teeth, [ka] and L4 is a ligand L B’ Ring A 1 binds to the ligand L B’ teeth, [ka] In such embodiments, the ligand L A’ is selected from the group consisting of structures defined in List 7 below. [ka] JPEG2025134732000085.jpg203160JPEG2025134732000086.jpg194160JPEG2025134732000087.jpg179160 JPEG2025134732000088.jpg212160JPEG2025134732000089.jpg218160JPEG2025134732000090.jpg195160J PEG2025134732000091.jpg193160JPEG2025134732000092.jpg204160JPEG2025134732000093.jpg210160J PEG2025134732000094.jpg192160JPEG2025134732000095.jpg195160JPEG2025134732000096.jpg215160JP EG2025134732000097.jpg209160JPEG2025134732000098.jpg196160JPEG2025134732000099.jpg222160JP EG2025134732000100.jpg205160JPEG2025134732000101.jpg226160JPEG2025134732000102.jpg207160JPE G2025134732000103.jpg208160JPEG2025134732000104.jpg210160JPEG2025134732000105.jpg211160JPE G2025134732000106.jpg188160JPEG2025134732000107.jpg176160JPEG2025134732000108.jpg185160In formula, L B’ is selected from the group consisting of the structures defined in Listing 8. TIFF2025134732000109.tif184160JPEG2025134732000110.jpg180160TIFF2025134732000111.tif199160TIFF2025134732000112.tif212160JPEG2025134732000113.jpg199160JPEG2025134732000114.jpg197160JPEG2025134732000115.jpg198160JPEG2025134732000116.jpg113160In the formula, R1 to R307 are defined in List 9 below. [ka] JPEG2025134732000118.jpg198160JPEG2025134732000119.jpg220160JPEG20251347320001 20.jpg195160JPEG2025134732000121.jpg190160JPEG2025134732000122.jpg199160JPEG20 25134732000123.jpg218160JPEG2025134732000124.jpg214160JPEG2025134732000125.jpg219160JPEG2025134732000126.jpg82160In the formula, Me is methyl, iPr is isopropyl, tBut is t-butyl, and Ph is phenyl.

[0113] In some embodiments, the compound is selected from the structures in list 10 below. [ka] JPEG2025134732000128.jpg192160JPEG2025134732000129.jpg186160JPEG2025134732000130.jpg200160JPEG2025134732000131.jpg208160JPEG202 5134732000132.jpg169160JPEG2025134732000133.jpg210160JPEG2025134 732000134.jpg183160JPEG2025134732000135.jpg168160JPEG20251347320 00136.jpg219160JPEG2025134732000137.jpg213160JPEG2025134732000138.jpg212160JPEG2025134732000139.jpg180160JPEG2025134732000140.j pg164160JPEG2025134732000141.jpg186160JPEG2025134732000142.jpg206160JPEG2025134732000143.jpg173160JPEG2025134732000144.jpg106160

[0114] C. OLEDs and Devices of the Present Disclosure In another aspect, the present disclosure also provides an OLED device that includes a first organic layer containing a compound disclosed in the Compounds section of this disclosure.

[0115] In some embodiments, an OLED comprises an anode, a cathode, and a first organic layer disposed between the anode and the cathode, the first organic layer comprising a ligand L comprising a moiety L described herein. A The compound may include a compound having the formula:

[0116] In some embodiments, the organic layer can be an emissive layer, and the compounds described herein can be an emissive or non-emissive dopant.

[0117] In some embodiments, the organic layer can further include a host, the host including a triphenylene containing benzo-fused thiophene or a benzo-fused furan, and any substituents in the host can independently be selected from the group consisting of C n H 2n+1 , O.C. n H 2n+1 , OAr1, N(C n H 2n+1 )2, N(Ar1)(Ar2), CH=CH-C n H 2n+1 , C≡CC n H 2n+1 , Ar1, Ar1-Ar2, C n H 2n -Ar1 is a non-fused substituent selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof, or can be unsubstituted, and n is 1 to 10. Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0118] In some embodiments, the organic layer can further include a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0119] In some embodiments, the host may be selected from the group of hosts selected from the group consisting of: [ka] [ka] [ka]

[0120] In some embodiments, the organic layer can further comprise a host, wherein the host comprises a metal complex.

[0121] In some embodiments, the compound described herein can be a sensitizer, and the device can further include an acceptor, and the acceptor can be selected from a fluorescent emitter, a delayed fluorescent emitter, and a combination thereof.

[0122] In yet another embodiment, the OLED of the present disclosure can also include a light-emitting region comprising a compound disclosed in the Compounds section of this disclosure.

[0123] In some embodiments, the emissive region comprises a ligand L comprising a moiety L described herein. A The compound may include a compound having the formula:

[0124] In some embodiments, at least one of the anode, cathode, or additional layers disposed on the organic light-emitting layer functions as an enhancement layer. The enhancement layer includes a plasmonic material that nonradiatively couples to the emitter material and exhibits a surface plasmon resonance that transfers excited-state energy from the emitter material to a nonradiative mode of surface plasmon polaritons. The enhancement layer is disposed within a threshold distance from the organic light-emitting layer, and the emitter material has a total nonradiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer, and at the threshold distance, the total nonradiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further includes an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer opposite the organic light-emitting layer. In some embodiments, the outcoupling layer is disposed on the opposite side of the enhancement layer from the light-emitting layer, but still outcouples energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, the energy is scattered from the surface plasmon mode into other modes of the device, such as, but not limited to, an organic waveguide mode, a substrate mode, or another waveguide mode. If the energy is scattered into a non-free-space mode of the OLED, other outcoupling schemes can be incorporated to extract the energy into free space. In some embodiments, one or more intervening layers can be disposed between the enhancement layer and the outcoupling layer. Examples of intervening layers can be dielectric materials, including organic, inorganic, perovskite, and oxide, and can include stacks and / or mixtures of these materials.

[0125] Enhancement layers alter the effective properties of the medium in which the emitter material resides, resulting in any or all of the following: a reduction in the emission rate; a change in the emission line shape; a change in the emission intensity with angle; a change in the stability of the emitter material; a change in the efficiency of the OLED; and a reduction in the efficiency roll-off of the OLED device. Placing an enhancement layer on the cathode side, the anode side, or both can result in an OLED device that utilizes any of the above-described effects. In addition to the specific functional layers shown in the various OLED examples described and illustrated herein, OLEDs according to the present disclosure can include any of the other functional layers frequently found in OLEDs.

[0126] The enhancement layer can be composed of a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmonic material is a material whose real part of its permittivity crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material includes at least one metal. In such embodiments, the metal can include at least one of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. In general, a metamaterial is a medium composed of different materials such that the medium as a whole behaves differently from the sum of its parts. In particular, an optically active metamaterial is defined as a material that has both a negative permittivity and a negative magnetic permeability. On the other hand, a hyperbolic metamaterial is an anisotropic medium in which the permittivity or permeability has different signs in different spatial directions. Optically active metamaterials and hyperbolic metamaterials are distinct from many other photonic structures, such as distributed Bragg reflectors ("DBRs"), in that they are media that appear uniform in the direction of propagation on the length scale of the wavelength of light. Using terminology understood by those skilled in the art, the dielectric constant of a metamaterial in the direction of propagation can be described by an effective medium approximation. Plasmonic materials and metamaterials offer a way to control the propagation of light and can improve OLED performance in a variety of ways.

[0127] In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has periodically, quasi-periodically, or randomly arranged wavelength-sized features or periodically, quasi-periodically, or randomly arranged sub-wavelength-sized features. In some embodiments, the wavelength-sized features and sub-wavelength-sized features have sharp edges.

[0128] In some embodiments, the outcoupling layer has periodically, quasi-periodically, or randomly arranged wavelength-sized features or periodically, quasi-periodically, or randomly arranged subwavelength-sized features. In some embodiments, the outcoupling layer can be composed of nanoparticles, and in other embodiments, the outcoupling layer is composed of nanoparticles disposed on a material. In these embodiments, outcoupling can be tunable by at least one of varying the size of the nanoparticles, varying the shape of the nanoparticles, varying the material of the nanoparticles, adjusting the thickness of the material, varying the refractive index of the material or the refractive index of an additional layer disposed on the nanoparticles, varying the thickness of an enhancement layer, and / or varying the material of the enhancement layer. The nanoparticles of the device can be formed from at least one of a metal, a dielectric material, a semiconductor material, an alloy of a metal, a mixture of dielectric materials, a stack or layer of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, the metal being selected from the group consisting of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. The nanoparticles can have additional layers disposed thereon. In some embodiments, the polarization of the emitted light can be adjusted using the outcoupling layer. By varying the dimensions and periodicity of the outcoupling layer, the type of polarization that is preferentially outcoupled to air can be selected. In some embodiments, the outcoupling layer also functions as an electrode for the device.

[0129] In yet another aspect, the present disclosure also provides a consumer product comprising an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound disclosed in the Compounds section of this disclosure.

[0130] In some embodiments, the consumer product is an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a ligand L comprising a moiety L as described herein. A The present invention also includes an OLED that can include a compound having the formula:

[0131] In some embodiments, the consumer product can be one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor illumination and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay less than 2 inches in diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays aligned together, a theater or stadium screen, a light therapy device, and a sign.

[0132] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons migrate to the oppositely charged electrode, respectively. When an electron and hole localize on the same molecule, an "exciton," a localized electron-hole pair with an excited energy state, is formed. Light is emitted via a photoemissive mechanism when the exciton relaxes. In some cases, the exciton may be localized on an excimer or exciplex. Non-radiative mechanisms, such as thermal relaxation, can also occur but are generally considered undesirable.

[0133] Some OLED materials and configurations are described in US Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated by reference in their entireties.

[0134] Early OLEDs used emissive molecules that emitted light from their singlet state ("fluorescence"), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a time frame of less than 10 nanoseconds.

[0135] More recently, OLEDs have been demonstrated that have emissive materials that emit light from triplet states ("phosphorescence"). Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, Vol. 395, No. 151-154, 1998; ("Baldo-I") and Baldo et al., "Very high-efficiency green organic light emitting devices based on electrophosphorescence," Appl. Phys. Lett., Vol. 75, No. 3, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entireties. Phosphorescence is described in further detail in U.S. Pat. No. 7,279,704, columns 5-6, which are incorporated by reference.

[0136] FIG. 1 shows an organic light-emitting device 100. The drawing is not necessarily to scale. Device 100 may include a substrate 110, an anode 115, a hole-injection layer 120, a hole-transport layer 125, an electron-blocking layer 130, an emissive layer 135, a hole-blocking layer 140, an electron-transport layer 145, an electron-injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in further detail in U.S. Pat. No. 7,279,704, cols. 6-10, which are incorporated by reference.

[0137] Further examples are available for each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes, including composite cathodes with a thin layer of metal, such as Mg:Ag, with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0138] FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole-transport layer 225, and an anode 230. Device 200 can be fabricated by depositing the layers described, in order. Because the most common OLED configuration has the cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides an example of how some layers can be omitted from the structure of device 100.

[0139] The simple layer structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and it is understood that embodiments of the present disclosure can be used in conjunction with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be achieved by combining the various layers described in various ways, or layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. While many of the examples provided herein describe various layers as including a single material, it is understood that combinations of materials, such as a mixture of a host and a dopant, or more generally, a mixture, may be used. Layers may also have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole-transport layer 225 transports holes and injects holes into emissive layer 220 and may be described as a hole-transport layer or a hole-injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include a single layer, or may further include multiple layers of different organic materials, such as those described with respect to Figures 1 and 2.

[0140] Structures and materials not specifically described may also be used, such as OLEDs (PLEDs) composed of polymeric materials, such as those disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. As a further example, an OLED having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Pat. No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from the simple layered structures illustrated in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces to improve outcoupling, such as the mesa structure described in U.S. Pat. No. 6,091,195 to Forrest et al. and / or the recessed structure described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0141] Unless otherwise specified, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include deposition by thermal evaporation, such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties; inkjet deposition; organic vapor phase deposition (OVPD), such as that described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety; and organic vapor jet printing (OVJP), such as that described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin-coating and other solution-based processes. Solution-based processes are preferably performed in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include patterning through a mask, such as those described in U.S. Patent Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, deposition via cold welding, and patterning associated with some deposition methods, such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to be compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, preferably containing at least three carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents with 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures, because asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

[0142] Devices fabricated according to embodiments of the present disclosure may further include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment, including moisture, vapors, and / or gases. The barrier layer may be deposited over, under, or adjacent to the substrate, the electrode, or any other portion of the device, including the edges. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds, or both. Preferred barrier layers include mixtures of polymeric and non-polymeric materials, as described in U.S. Pat. No. 7,968,146 and PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entireties. To be considered a "mixture," the polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and / or simultaneously. The weight ratio of polymeric to non-polymeric materials can be in the range of 95:5 to 5:95. The polymeric and non-polymeric materials can be made from the same precursor materials. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0143] Devices made according to embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into various electrical products or intermediate components. Such electrical products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels), and the like, which can be utilized by end-user product manufacturers. Such electronic component modules can optionally include drive electronics and / or power sources. Devices made according to embodiments of the present disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Consumer products are disclosed that include OLEDs that include compounds of the present disclosure in the organic layer of the OLED. Such consumer products include any type of product that includes one or more light sources and / or one or more visual displays of some kind. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays aligned together, theater or stadium screens, light therapy devices, and signage. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices fabricated according to the present disclosure. Many of the devices are intended for use within a temperature range comfortable to humans, such as 18°C ​​to 30°C, and more preferably room temperature (20-25°C), but can also be used outside this temperature range, e.g., between -40°C and +80°C.

[0144] Further details regarding OLEDs and the definitions set forth above can be found in US Pat. No. 7,279,704, which is incorporated by reference in its entirety.

[0145] The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.

[0146] In some embodiments, the OLED has one or more properties selected from the group consisting of flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

[0147] In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises an RGB pixel array or a white and color filter pixel array. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of ​​at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0148] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF) (also known as E-type delayed fluorescence; see, e.g., U.S. Application No. 15 / 700,352, incorporated by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the emissive dopant can be a racemic mixture or enriched in one enantiomer. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from the others). When more than one ligand is present that coordinates to the metal, in some embodiments, the ligands can all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, all of the ligands can be different from each other. This is true even in embodiments where a ligand coordinated to a metal can combine with other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Thus, when the coordinating ligands are bonded to one another, in some embodiments, all of the ligands can be identical, while in some other embodiments, at least one of the bonded ligands can be different from the other ligands.

[0149] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, where one or more layers in the OLED contain an acceptor in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound can be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor, which can emit energy or further transfer energy to the final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can come from any or all of the sensitizer, the acceptor, and the final emitter.

[0150] According to another aspect, compositions comprising the compounds described herein are also disclosed.

[0151] The OLEDs disclosed herein can be incorporated into one or more of consumer products, electronic component modules, and lighting panels. The organic layer can be an emissive layer, and in some embodiments, the compound can be an emissive dopant, while in other embodiments, the compound can be a non-emissive dopant.

[0152] In yet another aspect of the present disclosure, there is provided a composition comprising the novel compounds disclosed herein. The composition may also comprise one or more components selected from the group consisting of a solvent, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material disclosed herein.

[0153] The present disclosure encompasses any chemical structure comprising the novel compounds of the present disclosure, or monovalent or polyvalent variants thereof. In other words, the compounds of the present invention, or monovalent or polyvalent variants thereof, can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermolecules). As used herein, a "monovalent variant of a compound" refers to a moiety that is identical to the compound except that one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. As used herein, a "polyvalent variant of a compound" refers to a moiety that is identical to the compound except that more than one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. In the example of a supramolecule, the compounds of the present invention can also be incorporated into the supramolecular complex without a covalent bond.

[0154] D. Combinations of Compounds of the Present Disclosure with Other Materials The materials described herein as useful for a particular layer in an organic light-emitting device can be used in combination with a wide variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or referenced below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that may be useful in combination.

[0155] a) Conductive (electrically conductive) dopants: The charge transport layer is doped with a conductive dopant to significantly change the density of charge carriers and thereby its conductivity. The conductivity can be increased by generating charge carriers in the matrix material or, depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant, and n-type conductive dopants are used in the electron transport layer.

[0156] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are illustrated below, along with references that disclose these materials. EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012 [ka] [ka]

[0157] b) HIL / HTL: The hole injection / transport material used in the present disclosure is not particularly limited, and any compound may be used as long as it is a compound typically used as a hole injection / transport material. Examples of such materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorocarbons; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembly monomers derived from compounds such as phosphonic acid and silane derivatives; MoO xp-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds.

[0158] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structures: [ka]

[0159] Ar 1 From Ar 9each of which is a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazole, and aromatic heterocyclic compounds such as benzothiazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, which may be the same or different groups and which are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic cyclic group. Each Ar can be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0160] In one embodiment, Ar 1 From Ar9 teeth, [ka] (wherein k is an integer from 1 to 20; X 101 From X 108 is C (including CH) or N; Z 101 is NAr 1 , O, or S; Ar 1 has the same groups as defined above.

[0161] Examples of metal complexes used in the HIL or HTL include, but are not limited to, those of the following general formula: [ka] where Met is a metal that may have an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, and Y 101 and Y 102 are independently selected from C, N, O, P, and S; L 101 is an ancillary ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k'' is the maximum number of ligands that can be bound to the metal.

[0162] In one embodiment, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. 101 -Y 102 ) is a carbene ligand. In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex is + For the / Fc couple, it has a minimum oxidation potential of less than about 0.6 V in solution.

[0163] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references that disclose these materials. CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07-073529、JP2005112765、JP2007091719、JP2008021687、JP2014-009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018 [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0164] c) EBL: An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Blocking layers can also be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group used as one of the hosts described below.

[0165] d) Host: The light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. The host material is not particularly limited, and any metal complex or organic compound can be used as long as the triplet energy of the host is higher than that of the dopant. Any host material can be used with any dopant as long as the triplet criterion is met.

[0166] Examples of metal complexes used as host materials preferably have the following general formula: [ka] where Met is a metal; 103 -Y 104 ) is a bidentate ligand, and Y 103 and Y 104 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k'' is the maximum number of ligands that can be bound to the metal.

[0167] In one embodiment, the metal complex is: [ka] where (ON) is a bidentate ligand with the metal coordinated to atoms O and N.

[0168] In another embodiment, Met is selected from Ir and Pt. 103 -Y 104 ) is a carbene ligand.

[0169] In one embodiment, the host compound is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazoline, and aromatic heterocyclic compounds such as benzofuropyridine, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, which may be the same or different groups and which have 2 to 10 cyclic structural units bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic cyclic group. Each option within each group can be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0170] In one embodiment, the host compound contains at least one of the following groups in the molecule: [ka] [ka] In the formula, R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X 101 ~X 108 is independently selected from C (including CH) or N. Z 101 and Z 102 is independently, NR 101 , O, or S.

[0171] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references that disclose these materials. EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564 , TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US2 0090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012 126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO200706375 4. WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO20100 56066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO 2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803

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[0172] e) Additional luminaries: One or more additional emitter dopants can be used together with the compound of the present disclosure.The example of the additional emitter dopant is not particularly limited, and any compound can be used as long as the compound is typically used as an emitter material.Examples of suitable emitter materials include, but are not limited to, compounds that can generate light emission through phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes. Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references that disclose these materials. CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US 2014103305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US73 32232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586 , US8871361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO200201 5645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842 , WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO20 11044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO201317 4471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450,

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[0173] f) HBL: A hole-blocking layer (HBL) can be used to reduce the number of holes and / or excitons that escape from the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or a higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the HBL interface.

[0174] In one embodiment, the compounds used in the HBL contain the same molecules or the same functional groups as those used in the hosts described above.

[0175] In another embodiment, the compound used in the HBL comprises at least one of the following groups in the molecule: [ka] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0176] g)ETL: The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound typically used to transport electrons may be used.

[0177] In one embodiment, the compound used in the ETL contains at least one of the following groups in the molecule: [ka] In the formula, R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. 1 From Ar 3 has the same definition as that of Ar mentioned above. k is an integer from 1 to 20. X 101 From X 108 is selected from C (including CH) or N.

[0178] In another embodiment, the metal complex used in the ETL comprises, but is not limited to, the following general formula: [ka] where (ON) or (NN) is a bidentate ligand with the metal coordinated to atoms O, N or N, N; 101 is another ligand; and k' is an integer value between 1 and the maximum number of ligands that can be bound to the metal.

[0179] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references that disclose these materials. CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2 005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, U S20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US20 11210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO20 09148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, W O2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535 [ka] [ka] [ka]

[0180] h) Charge Generation Layer (CGL) In tandem or stacked OLEDs, the CGL plays a key role in performance and consists of an n-doped layer and a p-doped layer for electron and hole injection, respectively. Electrons and holes are supplied from the CGL and the electrodes. Consumed electrons and holes in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively, until the bipolar current gradually reaches a steady state. Typical CGL materials contain n-type and p-type conductivity dopants used in the transport layers.

[0181] In any of the above-mentioned compounds used in each layer of an OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically recited substituent, such as, but not limited to, methyl, phenyl, pyridyl, etc., can be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, substituent classes, such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc., can be undeuterated, partially deuterated, and fully deuterated versions thereof.

[0182] It is understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. Thus, the present invention as claimed may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

[0183] E. Experimental Data Table 1 Theoretical calculation [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4]

[0184] Table 1 shows the calculated triplet energies, HOMO, and LUMO of several compounds of the present invention. Geometry optimization calculations were performed in the Gaussian 09 software package using the B3LYP hybrid functional and CEP-31G basis set (including effective core potentials). Each compound exhibits a wide range of possible T1 energies, spanning from deep blue to near infrared, required for full-color displays.

[0185] It should be understood that the calculations performed with the DFT functions and basis sets identified herein are theoretical. Computational hybridization protocols, such as Gaussian with GEP-31G used herein, rely on the assumption that electronic effects are additive, and therefore larger basis sets can be used to extrapolate to the complete basis set (CBS) limit. However, when the goal of a study is to understand the variations in HOMO, LUMO, S1, T1, bond dissociation energies, etc., in a series of structurally related compounds, additive effects are expected to be similar. Therefore, although absolute errors using B3LYP may be significant compared to other computational methods, the relative differences between the HOMO, LUMO, S1, T1, and bond dissociation energy values ​​calculated with the B3LYP protocol are expected to closely reproduce experiment. See, e.g., Hong et al., Chem. Mater. 2016, 28, 5791-98, 5792-93, and Supplemental Information (discussing the reliability of DFT calculations with respect to OLED materials). Furthermore, for iridium and platinum complexes useful in OLED technology, data obtained by DFT calculations correlate very well with actual experimental data. See Tavasli et al., J. Mater. Chem. 2012, 22, 6419-29, 6422 (Table 3) (showing that DFT calculations correlate very well with actual data for various emissive complexes); Morello, GR, J. Mol. Model. 2017, 23:174 (studying various DFT functional and basis sets and concluding that the combination of B3LYP and CEP-31G is particularly accurate for emissive complexes). [Explanation of symbols]

[0186] 100 Organic Light-Emitting Devices 110 Substrate 115 Anode 120 Hole injection layer 125 Hole transport layer 130 Electron Blocking Layer 135 Light-emitting layer 140 Hole Blocking Layer 145 Electron transport layer 150 Electron injection layer 155 Protective layer 160 cathode 162 first conductive layer 164 Second conductive layer 170 Barrier Layer 200 Inverted OLED, device 210 Substrate 215 cathode 220 Light-emitting layer 225 Hole transport layer 230 Anode

Claims

1. Ligand L Ａ wherein the ligand L Ａ is represented by the following formula I: 【Chemical 1】 A compound comprising a moiety L having the structure: (In the formula, L Ａ is coordinated to the metal M; A １ is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; Rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Y １ , Y ２ , and Y ３ are each independently a moiety selected from the group consisting of a direct bond, C═R, NR, O, S, Se, BR, SiRR′, GeRR′, SnRR′, and a metal M; a, b, and c are each independently 0 when not present and 1 when present; a+b+c=2 or 3; R Ａ , R Ｂ , and R Ｃ each independently represents the maximum number of substitutions possible from mono or represents no substitution; R, R', R", R Ａ , R Ｂ , and R Ｃ are each independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; M can coordinate with other ligands; The ligand L Ａ can be combined with other ligands to form bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligands; R, R', R", R Ａ , R Ｂ , and R Ｃ any two substituents of may be joined or fused to form a ring; and At least one of the following conditions is met: 1) at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring; 2) Y １ , Y ２ , or Y ３ at least one of is present as C=R; 3) A １ is B and Y １ , Y ２ , or Y ３ at least one of is present as a direct bond; 4) A １ is B, a=b=1, and Y １ Y ２ different from; 5) A １ is N and Y １ , Y ２ , and Y ３ at least one of is present as BR; 6) A １ is B, a=b=1, and Y １ is not O; 7) the compound contains a metal-carbene bond; or 8) Adjacent R Ａ , R Ｂ , or R Ｃ At least one pair of is bonded to each other to form a fused moiety containing one or more rings fused to and extending from ring A, ring B, or ring C, respectively, and the fused moiety is directly coordinated to the metal M.

2. R, R', R", R Ａ , R Ｂ , and R Ｃ are each independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. 2. The compound of claim 1, wherein at most one of rings A, B, and C coordinates to the metal M.

4. The compound of claim 3 , wherein none of rings A, B, and C coordinates to the metal M.

5. 2. The compound of claim 1, wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

6. 2. The compound of claim 1, wherein the moiety L has a structure selected from the group consisting of: 【Chemistry 2】 【change】 (In the formula, X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ , X ９ , X １０ , X １１ , X １２ , X １３ , X １４ , X １５ , X １６ , X １７ , X １８ , and X １９ are each independently C or N; R Ｄ and R Ｅ each independently represents the maximum number of substitutions possible from mono or represents no substitution; R Ｄ and R Ｅ each independently represents a substituent selected from the group consisting of hydrogen, the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; Y ４ , Y ５ , and Y ６ are each independently selected from the group consisting of C═R, NR, O, S, Se, BR, CRR′, SiRR′, GeRR′, and SnRR′; and R, R', R", R Ａ , R Ｂ , R Ｃ , R Ｄ and R Ｅ Any two of the substituents in may be bonded or fused to form a ring.

7. 2. The compound of claim 1, wherein the compound has the structure of Formula II: 【Chemistry 3】 Formula II (In the formula, Z １ , Z ２ , Z ３ , and Z ４ are each independently selected from C or N; M １ is Pd or Pt; Ring A １ , A ２ , A ３ , and A ４ are each independently a monocyclic or polycyclic ring structure containing at least one 5- or 6-membered carbocyclic or heterocyclic ring; K １ ~K ４ are each independently selected from the group consisting of a direct bond, O, and S; K ３ and K. ４ at least one of is a direct bond; L １ ~L ４ are each independently selected from the group consisting of a single bond, no bond, O, S, C═R′, CR′R″, SiR′R″, BR′, BR′R″, and NR′; L １ ~L ４ at least two of: R １ ’ , R ２ ’ , R ３ ’ , and R ４ ’ each independently represents zero, mono, or up to the maximum number of substitutions allowed for its associated ring; R １ ’ , R ２ ’ , R ３ ’ , R ４ ’ , R', and R" each independently represent a substituent selected from the group consisting of hydrogen or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R １ ’ , R ２ ’ , R ３ ’ , R ４ ’ any two of R′, and R″ can be bonded or fused together to form a ring; R １ ’ , R ２ ’ , R ３ ’ , R ４ ’ , L １ , L ２ , L ３ , L ４ , ring A １ , ring A ２ , ring A ３ , ring A ４ At least one of or a combination thereof comprises the structure of Formula I.

8. L １ , L ２ , L ３ , and L ４ 8. The compound of claim 7, wherein at least one of is O, NR', or CR'R".

9. Z １ , Z ２ , Z ３ , and Z ４ The two are C and Z １ , Z ２ , Z ３ , and Z ４ The compound according to claim 7, wherein the remaining two are N.

10. K １ , K. ２ , K. ３ , and K ４ and each represent a direct bond.

11. 8. The compound of claim 7, wherein Formula II has a structure selected from the group consisting of: 【Chemistry 4】 【change】 (In the formula, R Ａ’ , R Ｂ’ , R Ｃ’ , R Ｄ’ , R Ｅ’ , R Ｆ’ , and R Ｇ’ each independently represents a substituent selected from the group consisting of hydrogen, the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R Ａ’ , R Ｂ’ , R Ｃ’ , R Ｄ’ , R Ｅ’ , R Ｆ’ , and R Ｇ’ any two substituents may be joined or fused to form a ring; R Ａ’ , R Ｂ’ , R Ｃ’ , R Ｄ’ , R Ｅ’ , R Ｆ’ , R Ｇ’ or combinations thereof, together with or apart from the remainder of formula II, comprise the structure of formula I.

12. The compound has the formula Pt(L Ａ’ ) (L Ｂ’ 8. The compound of claim 7, wherein (In the formula, the ligand L Ａ’ but, 【Chemistry 5】 and L ４ is the ligand L Ｂ’ Ring A １ and the ligand L Ｂ’ but has the following structure: 【Chemistry 6】 and The ligand L Ａ’ is selected from the group consisting of the structures defined below: 【Chemistry 7】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 In the ceremony, L Ｂ’ is selected from the group consisting of the structures defined below: 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 In the formula, R1 to R307 are defined as follows. 【Chemistry 8】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 In the formula, Me is methyl, iPr is isopropyl, tBu is t-butyl, and Ph is phenyl.

13. 8. The compound of claim 7, wherein the compound has a structure selected from: 【Chemistry 9】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

14. An organic light emitting device (OLED), comprising: an anode; a cathode; an organic layer disposed between the anode and the cathode; The organic layer contains the ligand L Ａ wherein the ligand L Ａ is represented by the following formula I: 【Chemistry 10】 1. An organic light emitting device (OLED) comprising a compound comprising a moiety L having the structure: (In the formula, L Ａ is coordinated to the metal M; A １ is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; Rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Y １ , Y ２ , and Y ３ are each independently a moiety selected from the group consisting of a direct bond, C═R, NR, O, S, Se, BR, SiRR′, GeRR′, SnRR′, and a metal M; a, b, and c are each independently 0 when not present and 1 when present; a+b+c=2 or 3; R Ａ , R Ｂ , and R Ｃ each independently represents the maximum number of substitutions possible from mono or represents no substitution; R, R', R", R Ａ , R Ｂ , and R Ｃ are each independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; M can coordinate with other ligands; The ligand L Ａ can be combined with other ligands to form bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligands; R, R', R", R Ａ , R Ｂ , and R Ｃ any two substituents of may be joined or fused to form a ring; and At least one of the following conditions is met: 1) at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring; 2) Y １ , Y ２ , or Y ３ at least one of is present as C=R; 3) A １ is B and Y １ , Y ２ , or Y ３ at least one of is present as a direct bond; 4) A １ is B, a=b=1, and Y １ Y ２ different from; 5) A １ is N and Y １ , Y ２ , and Y ３ at least one of is present as BR; 6) A １ is B, a=b=1, and Y １ is not O; 7) the compound contains a metal-carbene bond; or 8) Adjacent R Ａ , R Ｂ , or R Ｃ At least one pair of is bonded to each other to form a fused moiety containing one or more rings fused to and extending from ring A, ring B, or ring C, respectively, and the fused moiety is directly coordinated to the metal M.

15. 1. A consumer product comprising an organic light emitting device (OLED), the organic light emitting device (OLED) comprising: an anode; a cathode; an organic layer disposed between the anode and the cathode; The organic layer contains the ligand L Ａ wherein the ligand L Ａ is represented by the following formula I: 【Chemistry 11】 1. A consumer product characterized in that it is an organic light emitting device (OLED) comprising a compound comprising a moiety L having the structure: (In the formula, L Ａ is coordinated to the metal M; A １ is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; Rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Y １ , Y ２ , and Y ３ are each independently a moiety selected from the group consisting of a direct bond, C═R, NR, O, S, Se, BR, SiRR′, GeRR′, SnRR′, and a metal M; a, b, and c are each independently 0 when not present and 1 when present; a+b+c=2 or 3; R Ａ , R Ｂ , and R Ｃ each independently represents the maximum number of substitutions possible from mono or represents no substitution; R, R', R", R Ａ , R Ｂ , and R Ｃ are each independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; M can coordinate with other ligands; The ligand L Ａ can be combined with other ligands to form bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligands; R, R', R", R Ａ , R Ｂ , and R Ｃ any two substituents of may be joined or fused to form a ring; and At least one of the following conditions is met: 1) at least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring; 2) Y １ , Y ２ , or Y ３ at least one of is present as C=R; 3) A １ is B and Y １ , Y ２ , or Y ３ at least one of is present as a direct bond; 4) A １ is B, a=b=1, and Y １ Y ２ different from; 5) A １ is N and Y １ , Y ２ , and Y ３ at least one of is present as BR; 6) A １ is B, a=b=1, and Y １ is not O; 7) the compound contains a metal-carbene bond; or 8) Adjacent R Ａ , R Ｂ , or R Ｃ At least one pair of is bonded to each other to form a fused moiety containing one or more rings fused to and extending from ring A, ring B, or ring C, respectively, and the fused moiety is directly coordinated to the metal M.

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