ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

Information

  • Patent Application
  • 20230118106
  • Publication Number
    20230118106
  • Date Filed
    July 28, 2022
    a year ago
  • Date Published
    April 20, 2023
    a year ago
Abstract
Heteroleptic compounds having a structure of Ir(LA)p(LB)q(LC)r, where LB and LC are different bidentate ligands, p is 1 or 2, q is 1 or 2, r is 0, 1, or 2, and ligand LA has a structure of Formula I,
Description
FIELD

The present disclosure generally relates to organometallic compounds and formulations and their various uses including as emitters in devices such as organic light emitting diodes and related electronic devices.


BACKGROUND

Opto-electronic devices that make use of organic materials are becoming increasingly desirable for various reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials.


OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting.


One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively, the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single emissive layer (EML) device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.


SUMMARY

In one aspect, the present disclosure provides a structure of Ir(LA)p(LB)q(LC)r, wherein LB and LC are different bidentate ligands; wherein p is 1 or 2; q is 1 or 2; r is 0, 1, or 2; and wherein ligand LA has a structure of Formula I,




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In Formula I:

moiety B is a monocyclic or polycyclic fused ring system comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;


each of X1 to X6 is independently C or N;


RA, RB, and RC each independently represents mono to the maximum number of allowable substitutions, or no substitution;


each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;


at least one RB comprises a partially or fully deuterated alkyl or a partially or fully deuterated cycloalkyl group;


any two adjacent RA, two adjacent RC, one RA and one RB, or one RB and one RC can be joined or fused to form a ring;


if moiety B is a monocyclic 6-membered carbocyclic ring, then at least two adjacent RC substituents are fused to form a 5-membered ring or a 6-membered ring;


wherein the compound is heteroleptic; and


wherein LA may be joined with other LB or LC ligands to form a tetradentate or hexadentate ligand, with the proviso that at least one LB or LC is present and is not a phenylpyridine-based ligand.


In another aspect, the present disclosure provides a formulation comprising a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.


In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.


In yet another aspect, the present disclosure provides a consumer product comprising an OLED with an organic layer comprising a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.





BRIEF DESCRIPTION OF THE DRAWINGS


FIG. 1 shows an organic light emitting device.



FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.





DETAILED DESCRIPTION
A. Terminology

Unless otherwise specified, the below terms used herein are defined as follows:


As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat 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 may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.


As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, 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 are various organic layers in between.


As used herein, “solution processable” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.


A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.


As used herein, and as would be generally understood by one 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.


Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). 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.


As used herein, and as would be generally understood by one 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 further 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.


The terms “halo,” “halogen,” and “halide” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.


The term “acyl” refers to a substituted carbonyl radical (C(O)—Rs).


The term “ester” refers to a substituted oxycarbonyl (—O—C(O)—Rs or —C(O)—O—Rs) radical.


The term “ether” refers to an —ORs radical.


The terms “sulfanyl” or “thio-ether” are used interchangeably and refer to a —SRs radical.


The term “selenyl” refers to a —SeRs radical.


The term “sulfinyl” refers to a —S(O)—Rs radical.


The term “sulfonyl” refers to a —SO2—Rs radical.


The term “phosphino” refers to a —P(Rs)3 radical, wherein each Rs can be same or different.


The term “silyl” refers to a —Si(Rs)3 radical, wherein each Rs can be same or different.


The term “germyl” refers to a —Ge(Rs)3 radical, wherein each Rs can be same or different.


The term “boryl” refers to a —B(Rs)2 radical or its Lewis adduct —B(Rs)3 radical, wherein Rs can be same or different.


In each of the above, Rs 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 combination thereof. Preferred Rs is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.


The term “alkyl” refers to and includes both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group may be optionally substituted.


The term “cycloalkyl” refers to and includes monocyclic, polycyclic, and spiro alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl group may be optionally substituted.


The terms “heteroalkyl” or “heterocycloalkyl” refer to an alkyl or a cycloalkyl radical, 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. Additionally, the heteroalkyl or heterocycloalkyl group may be optionally substituted.


The term “alkenyl” refers to and includes both straight and branched chain alkene radicals. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. The term “heteroalkenyl” as used herein refers to an alkenyl radical 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 two to fifteen carbon atoms. Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl group may be optionally substituted.


The term “alkynyl” refers to and includes both straight and branched chain alkyne radicals. Alkynyl groups are essentially alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.


The terms “aralkyl” or “arylalkyl” are used interchangeably and refer to an alkyl group that is substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.


The term “heterocyclic group” refers to and includes aromatic and non-aromatic cyclic radicals 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. Hetero-aromatic cyclic radicals may be used interchangeably with heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers/thio-ethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Additionally, the heterocyclic group may be optionally substituted.


The term “aryl” refers to and includes both single-ring aromatic hydrocarbyl groups and polycyclic aromatic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is an aromatic hydrocarbyl group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted.


The term “heteroaryl” refers to and includes both single-ring aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. The heteroatoms include, but are not limited to O, S, N, P, B, Si, and Se. In many instances, O, S, or N are the preferred heteroatoms. Hetero-single ring aromatic systems are preferably single rings with 5 or 6 ring atoms, and the ring can have from one to six heteroatoms. The hetero-polycyclic ring systems can have two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. The hetero-polycyclic aromatic ring systems can have from one to six heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve 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, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.


Of the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and the respective aza-analogs of each thereof are of particular interest.


The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted, or independently substituted, with one or more general substituents.


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


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


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


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


The terms “substituted” and “substitution” refer to a substituent other than H that is bonded to the relevant position, e.g., a carbon or nitrogen. For example, when R1 represents mono-substitution, then one R1 must be other than H (i.e., a substitution). Similarly, when R1 represents di-substitution, then two of R1 must be other than H. Similarly, when R1 represents zero or no substitution, R1, for example, can be a hydrogen for available valencies of ring atoms, as in carbon atoms for benzene and the nitrogen atom in pyrrole, or simply represents nothing for ring atoms with fully filled valencies, e.g., the nitrogen atom in pyridine. The maximum number of substitutions possible in a ring structure will depend on the total number of available valencies in the ring atoms.


As used herein, “combinations thereof” indicates that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, an alkyl and deuterium can be combined to form a partial or fully deuterated alkyl group; a halogen and alkyl can be combined to form a halogenated alkyl substituent; and a halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. In one instance, the term substitution includes a combination of two to four of the listed groups. In another instance, the term substitution includes a combination of two to three groups. In yet another instance, the term substitution includes a combination of two groups. Preferred combinations of substituent groups are those that contain up to fifty atoms that are not hydrogen or deuterium, or those which include up to forty atoms that are not hydrogen or deuterium, or those that include up to thirty atoms that are not hydrogen or deuterium. In many instances, a preferred combination of substituent groups will include up to twenty atoms that are not hydrogen or deuterium.


The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective aromatic ring can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.


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, Patent Pub. No. WO 2006/095951, and U.S. Pat. Application Pub. No. US 2011/0037057, which are hereby incorporated by reference in their entireties, describe the making of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan, et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65, which are incorporated by reference in their entireties, describe the deuteration of the methylene hydrogens in benzyl amines and efficient pathways to replace aromatic ring hydrogens with deuterium, respectively.


It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.


In some instance, a pair of adjacent substituents can be optionally joined or fused into a ring. The preferred ring is a five, six, or seven-membered carbocyclic or heterocyclic ring, includes both instances where the portion of the ring formed by the pair of substituents is saturated and where the portion of the ring formed by the pair of substituents is unsaturated. As used herein, “adjacent” means that the two substituents involved can be on the same ring next to each other, or on two neighboring rings having the two closest available substitutable positions, such as 2, 2′ positions in a biphenyl, or 1, 8 position in a naphthalene, as long as they can form a stable fused ring system.


B. The Compounds of the Present Disclosure

In one aspect, the present disclosure provides a structure of Ir(LA)p(LB)q(LC)r, wherein LB and LC are different bidentate ligands; wherein p is 1 or 2; q is 1 or 2; r is 0, 1, or 2; and wherein ligand LA has a structure of Formula I,




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In Formula I:

moiety B is a monocyclic or polycyclic fused ring system comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;


each of X1 to X6 is independently C or N;


RA, RB, and RC each independently represents mono to the maximum number of allowable substitutions, or no substitution;


each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the General Substituents defined herein;


at least one RB comprises a partially or fully deuterated alkyl or a partially or fully deuterated cycloalkyl group;


any two adjacent RA, two adjacent RC, one RA and one RB, or one RB and one RC can be joined or fused to form a ring;


if moiety B is a monocyclic 6-membered carbocyclic ring, then at least two adjacent RC substituents are fused to form a 5-membered ring or a 6-membered ring;


wherein the compound is heteroleptic; and


wherein LA may be joined with other LB or LC ligands to form a tetradentate or hexadentate ligand, with the proviso that at least one LB or LC is present and is not a phenylpyridine-based ligand.


As used herein, a phenylpyridine-based ligand is a bidentate ligand where both phenyl and the N of a pyridine is coordinated to the metal.


In some embodiments, each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the Preferred General Substituents defined herein. In some embodiments, each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the More Preferred General Substituents defined herein. In some embodiments, each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the Most Preferred General Substituents defined herein.


In some embodiments, at least one of X1 and X2 is N. In some embodiments, exactly one of X1 and X2 is N. In some embodiments, X1 and X2 are C.


In some embodiments, moiety B is monocyclic. In some embodiments, moiety B is polycyclic. In some embodiments, moiety B is aromatic. In some embodiments, moiety B is selected from the group consisting of phenyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, phenanthridine, fluorene, naphtho[2,3-b]thiophene, and naphtho[2,3-b]furan.


In some embodiments, each of X3 to X6 is C. In some embodiments, at least one of X3 to X6 is N. In some embodiments, exactly one of X3 to X6 is N.


In some embodiments, the at least one RB comprises aryl or heteroaryl.


In some embodiments, the at least one RB substituent comprises a partially deuterated alkyl or a partially deuterated cycloalkyl group. In some embodiments, the at least one RB substituent is a partially deuterated alkyl or a partially deuterated cycloalkyl group.


In some embodiments, the at least one RB substituent comprises a partially or fully deuterated alkyl with at least 3 carbon atoms. In some embodiments, the at least one RB substituent comprises a partially or fully deuterated alkyl with at least 4 carbon atoms, or at least 5 carbon atoms, or at least 6 carbon atoms.


In some embodiments, the at least one RB substituent is a partially or fully deuterated alkyl with at least 3 carbon atoms. In some embodiments, the at least one RB substituent is a partially or fully deuterated alkyl with at least 4 carbon atoms, or at least 5 carbon atoms, or at least 6 carbon atoms.


In some embodiments, two adjacent RA are joined or fused to form a ring. In some embodiments, two adjacent RA are joined or fused to form a 5-membered or 6-membered ring. In some embodiments, two adjacent RA are joined or fused to form a ring selected from the group consisting of phenyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and combinations thereof.


In some embodiments, two adjacent RC are joined or fused to form a ring. In some embodiments, two adjacent RC are joined or fused to form a 5-membered or 6-membered ring. In some embodiments, two adjacent RC are joined or fused to form a ring selected from the group consisting of phenyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and combinations thereof.


In some embodiments, two RC are joined to form a polycyclic fused ring structure. In some embodiments, two RA are joined to form a polycyclic fused ring structure. In some embodiments. two RB are joined to form a polycyclic fused ring structure. In some embodiments, moiety E is a polycyclic fused ring structure.


In some of the above embodiments, the polycyclic fused ring structure comprising at least three fused rings In some embodiments, the polycyclic fused ring structure has two 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to Ir and the second 6-membered ring is fused to the 5-membered ring.


In some of the above embodiments, the polycyclic fused ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused ring structure comprises three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to Ir, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted by a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.


In some of the above embodiments, the polycyclic fused ring structure comprising at least five fused rings. In some embodiments, the polycyclic fused ring structure comprises four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments with one 5-membered ring, the 5-membered ring is fused to the ring coordinated to Ir, the second 6-membered ring is fused to the 5-membered ring, the third 6-membered ring is fused to the second 6-membered ring, and the fourth 6-membered ring is fused to the third-6-membered ring.


In some of the above embodiments, the polycyclic fused ring structure may have its aza version of the fused rings as described above. In some such embodiments, each polycyclic fused ting structure contains exact one aza N atom. In some such embodiments, each polycyclic fused ting structure contains exact two aza N atoms, which can be in one ring, or in two different rings. In some such embodiments, the ring having aza N atom is at least separated by another two rings from the Ir atom. In some such embodiments, the ring having aza N atom is at least separated by another three rings from the Ir atom. In some such embodiments, each of the ortho position of the aza N atom is substituted.


In some embodiments, X5 and X6 are C and the RC located at X5 and X6 are joined or fused to form a 5- or 6-membered ring. In some such embodiments, the RC substituents at X5 and X6 are fused to form a ring selected from the group consisting of phenyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and combinations thereof.


In some embodiments, one RA and one RB are joined or fused to form a ring.


In some embodiments, one RB and one RC are joined or fused to form a ring.


In some embodiments, an RC located at one of X3 to X6 is alkyl or cycloalkyl. In some embodiments, an RC located at one of X3 to X6 is alkyl or cycloalkyl comprising at least 3 carbon atoms or at least 4 carbon atoms. In some embodiments, an RC located at one of X3 to X6 is t-butyl or substituted t-butyl.


In some embodiments, X4 is C and the RC located at X4 is alkyl or cycloalkyl. In some embodiments, X4 is C and the RC located at X4 is alkyl or cycloalkyl comprising at least 3 carbon atoms or at least 4 carbon atoms. In some embodiments, X4 is C and the RC located at X4 is t-butyl or substituted t-butyl.


In some embodiments, at least one RA is a substituent selected from the group consisting of the Preferred General Substituents defined herein.


In some embodiments, at least one RB comprises a substituent other than partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl.


In some embodiments, at least one RC is a substituent selected from the group consisting of the Preferred General Substituents defined herein.


In some embodiments, the ligand LA is selected from the group consisting of the structures of the following


LIST 1:



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wherein:


each of X7 to X12 is independently C or N;


each of Y1a and Y1b is independently selected from the group consisting of BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CRR′, SiRR′, and GeRR′;


each R and R′ is independently a hydrogen or a substituent selected from the group consisting of the General Substituents defined herein; and


wherein any two adjacent substituents can be joined or fused to form a ring.


In some embodiments, the ligand LA is selected from the group consisting of the structures of the following


LIST 2:



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wherein RC1 each independently represents mono to the maximum number of allowable substitutions, or no substitution;


each of Y1a and Y1b is independently selected from the group consisting of BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CRR′, SiRR′, and GeRR′;


each R, R′, and RC is independently a hydrogen or a substituent selected from the group consisting of the General Substituents defined herein


any two adjacent substituents can be joined or fused to form a ring.


In some embodiments, the ligand LA is Selected from the group consisting of LA1-1 to LA1500-45, where for LAi-m, m is an integer from 1 to 45 and i is an integer from 1 to 1500;


wherein LAi-1 to LAi-45 have the structures defined in the following LIST 3:




embedded image


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wherein for each i, RE, RF, and G are defined in the following LIST 4:

















i
RF
RE
G








  1
R1
R31
G4



  2
R1
R32
G4



  3
R1
R33
G4



  4
R1
R34
G4



  5
R1
R35
G4



  6
R1
R36
G4



  7
R1
R37
G4



  8
R1
R38
G4



  9
R1
R39
G4



 10
R1
R40
G4



 11
R1
R41
G4



 12
R1
R42
G4



 13
R1
R43
G4



 14
R1
R44
G4



 15
R1
R45
G4



 16
R1
R46
G4



 17
R1
R47
G4



 18
R1
R48
G4



 19
R1
R49
G4



 20
R1
R50
G4



 21
R1
R51
G4



 22
R1
R52
G4



 23
R1
R53
G4



 24
R1
R54
G4



 25
R1
R55
G4



 26
R1
R56
G4



 27
R1
R57
G4



 28
R1
R58
G4



 29
R1
R59
G4



 30
R1
R60
G4



 31
R3
R31
G4



 32
R3
R32
G4



 33
R3
R33
G4



 34
R3
R34
G4



 35
R3
R35
G4



 36
R3
R36
G4



 37
R3
R37
G4



 38
R3
R38
G4



 39
R3
R39
G4



 40
R3
R40
G4



 41
R3
R41
G4



 42
R3
R42
G4



 43
R3
R43
G4



 44
R3
R44
G4



 45
R3
R45
G4



 46
R3
R46
G4



 47
R3
R47
G4



 48
R3
R48
G4



 49
R3
R49
G4



 50
R3
R50
G4



 51
R3
R51
G4



 52
R3
R52
G4



 53
R3
R53
G4



 54
R3
R54
G4



 55
R3
R55
G4



 56
R3
R56
G4



 57
R3
R57
G4



 58
R3
R58
G4



 59
R3
R59
G4



 60
R3
R60
G4



 61
R4
R31
G4



 62
R4
R32
G4



 63
R4
R33
G4



 64
R4
R34
G4



 65
R4
R35
G4



 66
R4
R36
G4



 67
R4
R37
G4



 68
R4
R38
G4



 69
R4
R39
G4



 70
R4
R40
G4



 71
R4
R41
G4



 72
R4
R42
G4



 73
R4
R43
G4



 74
R4
R44
G4



 75
R4
R45
G4



 76
R4
R46
G4



 77
R4
R47
G4



 78
R4
R48
G4



 79
R4
R49
G4



 80
R4
R50
G4



 81
R4
R51
G4



 82
R4
R52
G4



 83
R4
R53
G4



 84
R4
R54
G4



 85
R4
R55
G4



 86
R4
R56
G4



 87
R4
R57
G4



 88
R4
R58
G4



 89
R4
R59
G4



 90
R4
R60
G4



 91
R31
R1
G4



 92
R31
R2
G4



 93
R31
R3
G4



 94
R31
R4
G4



 95
R31
R5
G4



 96
R31
R6
G4



 97
R31
R7
G4



 98
R31
R8
G4



 99
R31
R9
G4



 100
R31
R10
G4



 101
R31
R11
G4



 102
R31
R12
G4



 103
R31
R13
G4



 104
R31
R14
G4



 105
R31
R15
G4



 106
R31
R16
G4



 107
R31
R17
G4



 108
R31
RI
G4



 109
R31
R19
G4



 110
R31
R20
G4



 111
R31
R21
G4



 112
R31
R22
G4



 113
R31
R23
G4



 114
R31
R24
G4



 115
R31
R25
G4



 116
R31
R26
G4



 117
R31
R27
G4



 118
R31
R28
G4



 119
R31
R29
G4



 120
R31
R30
G4



 121
R31
R31
G4



 122
R31
R32
G4



 123
R31
R33
G4



 124
R31
R34
G4



 125
R31
R35
G4



 126
R31
R36
G4



 127
R31
R37
G4



 128
R31
R38
G4



 129
R31
R39
G4



 130
R31
R40
G4



 131
R31
R41
G4



 132
R31
R42
G4



 133
R31
R43
G4



 134
R31
R44
G4



 135
R31
R45
G4



 136
R31
R46
G4



 137
R31
R47
G4



 138
R31
R48
G4



 139
R31
R49
G4



 140
R31
R50
G4



 141
R31
R51
G4



 142
R31
R52
G4



 143
R31
R53
G4



 144
R31
R54
G4



 145
R31
R55
G4



 146
R31
R56
G4



 147
R31
R57
G4



 148
R31
R58
G4



 149
R31
R59
G4



 150
R31
R60
G4



 151
R1
R31
G28



 152
R1
R32
G28



 153
R1
R33
G28



 154
R1
R34
G28



 155
R1
R35
G28



 156
R1
R36
G28



 157
R1
R37
G28



 158
R1
R38
G28



 159
R1
R39
G28



 160
R1
R40
G28



 161
R1
R41
G28



 162
R1
R42
G28



 163
R1
R43
G28



 164
R1
R44
G28



 165
R1
R45
G28



 166
R1
R46
G28



 167
R1
R47
G28



 168
R1
R48
G28



 169
R1
R49
G28



 170
R1
R50
G28



 171
R1
R51
G28



 172
R1
R52
G28



 173
R1
R53
G28



 174
R1
R54
G28



 175
R1
R55
G28



 176
R1
R56
G28



 177
R1
R57
G28



 178
R1
R58
G28



 179
R1
R59
G28



 180
R1
R60
G28



 181
R3
R31
G28



 182
R3
R32
G28



 183
R3
R33
G28



 184
R3
R34
G28



 185
R3
R35
G28



 186
R3
R36
G28



 187
R3
R37
G28



 188
R3
R38
G28



 189
R3
R39
G28



 190
R3
R40
G28



 191
R3
R41
G28



 192
R3
R42
G28



 193
R3
R43
G28



 194
R3
R44
G28



 195
R3
R45
G28



 196
R3
R46
G28



 197
R3
R47
G28



 198
R3
R48
G28



 199
R3
R49
G28



 200
R3
R50
G28



 201
R3
R51
G28



 202
R3
R52
G28



 203
R3
R53
G28



 204
R3
R54
G28



 205
R3
R55
G28



 206
R3
R56
G28



 207
R3
R57
G28



 208
R3
R58
G28



 209
R3
R59
G28



 210
R3
R60
G28



 211
R4
R31
G28



 212
R4
R32
G28



 213
R4
R33
G28



 214
R4
R34
G28



 215
R4
R35
G28



 216
R4
R36
G28



 217
R4
R37
G28



 218
R4
R38
G28



 219
R4
R39
G28



 220
R4
R40
G28



 221
R4
R41
G28



 222
R4
R42
G28



 223
R4
R43
G28



 224
R4
R44
G28



 225
R4
R45
G28



 226
R4
R46
G28



 227
R4
R47
G28



 228
R4
R48
G28



 229
R4
R49
G28



 230
R4
R50
G28



 231
R4
R51
G28



 232
R4
R52
G28



 233
R4
R53
G28



 234
R4
R54
G28



 235
R4
R55
G28



 236
R4
R56
G28



 237
R4
R57
G28



 238
R4
R59
G28



 239
R4
R59
G28



 240
R4
R60
G28



 241
R31
R1
G28



 242
R31
R2
G28



 243
R31
R3
G28



 244
R31
R4
G28



 245
R31
R5
G28



 246
R31
R6
G28



 247
R31
R7
G28



 248
R31
R8
G28



 249
R31
R9
G28



 250
R31
R10
G28



 251
R31
R11
G28



 252
R31
R12
G28



 253
R31
R13
G28



 254
R31
R14
G28



 255
R31
R15
G28



 256
R31
R16
G28



 257
R31
R17
G28



 258
R31
R18
G28



 259
R31
R19
G28



 260
R31
R20
G28



 261
R31
R21
G28



 262
R31
R22
G28



 263
R31
R23
G28



 264
R31
R24
G28



 265
R31
R25
G28



 266
R31
R26
G28



 267
R31
R27
G28



 268
R31
R28
G28



 269
R31
R29
G28



 270
R31
R30
G28



 271
R31
R31
G28



 272
R31
R32
G28



 273
R31
R33
G28



 274
R31
R34
G28



 275
R31
R35
G28



 276
R31
R36
G28



 277
R31
R37
G28



 278
R31
R38
G28



 279
R31
R39
G28



 280
R31
R40
G28



 281
R31
R41
G28



 282
R31
R42
G28



 283
R31
R43
G28



 284
R31
R44
G28



 285
R31
R45
G28



 286
R31
R46
G28



 287
R31
R47
G28



 288
R31
R48
G28



 289
R31
R49
G28



 290
R31
R50
G28



 291
R31
R51
G28



 292
R31
R52
G28



 293
R31
R53
G28



 294
R31
R54
G28



 295
R31
R55
G28



 296
R31
R56
G28



 297
R31
R57
G28



 298
R31
R58
G28



 299
R31
R59
G28



 300
R31
R60
G28



 301
R1
R31
G1



 302
R1
R32
G1



 303
R1
R36
G1



 304
R1
R39
G1



 305
R1
R45
G1



 306
R1
R49
G1



 307
R1
R55
G1



 308
R1
R57
G1



 309
R1
R58
G1



 310
R1
R60
G1



 311
R3
R31
G1



 312
R3
R32
G1



 313
R3
R36
G1



 314
R3
R39
G1



 315
R3
R45
G1



 316
R3
R49
G1



 317
R3
R55
G1



 318
R3
R57
G1



 319
R3
R58
G1



 320
R3
R60
G1



 321
R4
R31
G1



 322
R4
R32
G1



 323
R4
R36
G1



 324
R4
R39
G1



 325
R4
R45
G1



 326
R4
R49
G1



 327
R4
R55
G1



 328
R4
R57
G1



 329
R4
R58
G1



 330
R4
R60
G1



 331
R31
R31
G1



 332
R31
R32
G1



 333
R31
R36
G1



 334
R31
R39
G1



 335
R31
R45
G1



 336
R31
R49
G1



 337
R31
R55
G1



 338
R31
R57
G1



 339
R31
R58
G1



 340
R31
R60
G1



 341
R1
R31
G2



 342
R1
R32
G2



 343
R1
R36
G2



 344
R1
R39
G2



 345
R1
R45
G2



 346
R1
R49
G2



 347
R1
R55
G2



 348
R1
R57
G2



 349
R1
RS
G2



 350
R1
R60
G2



 351
R3
R31
G2



 352
R3
R32
G2



 353
R3
R36
G2



 354
R3
R39
G2



 355
R3
R45
G2



 356
R3
R49
G2



 357
R3
R55
G2



 358
R3
R57
G2



 359
R3
RS
G2



 360
R3
R60
G2



 361
R4
R31
G2



 362
R4
R32
G2



 363
R4
R36
G2



 364
R4
R39
G2



 365
R4
R45
G2



 366
R4
R49
G2



 367
R4
R55
G2



 368
R4
R57
G2



 369
R4
R58
G2



 370
R4
R60
G2



 371
R31
R31
G2



 372
R31
R32
G2



 373
R31
R36
G2



 374
R31
R39
G2



 375
R31
R45
G2



 376
R31
R49
G2



 377
R31
R55
G2



 378
R31
R57
G2



 379
R31
R58
G2



 380
R31
R60
G2



 381
R1
R31
G3



 382
R1
R32
G3



 383
R1
R36
G3



 384
R1
R39
G3



 385
R1
R45
G3



 386
R1
R49
G3



 387
R1
R55
G3



 388
R1
R57
G3



 389
R1
R58
G3



 390
R1
R60
G3



 391
R3
R31
G3



 392
R3
R32
G3



 393
R3
R36
G3



 394
R3
R39
G3



 395
R3
R45
G3



 396
R3
R49
G3



 397
R3
R55
G3



 398
R3
R57
G3



 399
R3
R58
G3



 400
R3
R60
G3



 401
R4
R31
G3



 402
R4
R32
G3



 403
R4
R36
G3



 404
R4
R39
G3



 405
R4
R45
G3



 406
R4
R49
G3



 407
R4
R55
G3



 408
R4
R57
G3



 409
R4
R58
G3



 410
R4
R60
G3



 411
R31
R31
G3



 412
R31
R32
G3



 413
R31
R36
G3



 414
R31
R39
G3



 415
R31
R45
G3



 416
R31
R49
G3



 417
R31
R55
G3



 418
R31
R57
G3



 419
R31
R58
G3



 420
R31
R60
G3



 421
R1
R31
G5



 422
R1
R32
G5



 423
R1
R36
G5



 424
R1
R39
G5



 425
R1
R45
G5



 426
R1
R49
G5



 427
R1
R55
G5



 428
R1
R57
G5



 429
R1
R58
G5



 430
R1
R60
G5



 431
R3
R31
G5



 432
R3
R32
G5



 433
R3
R36
G5



 434
R3
R39
G5



 435
R3
R45
G5



 436
R3
R49
G5



 437
R3
R55
G5



 438
R3
R57
G5



 439
R3
R58
G5



 440
R3
R60
G5



 441
R4
R31
G5



 442
R4
R32
G5



 443
R4
R36
G5



 444
R4
R39
G5



 445
R4
R45
G5



 446
R4
R49
G5



 447
R4
R55
G5



 448
R4
R57
G5



 449
R4
R58
G5



 450
R4
R60
G5



 451
R31
R31
G5



 452
R31
R32
G5



 453
R31
R36
G5



 454
R31
R39
G5



 455
R31
R45
G5



 456
R31
R49
G5



 457
R31
R55
G5



 458
R31
R57
G5



 459
R31
R58
G5



 460
R31
R60
G5



 461
R1
R31
G6



 462
R1
R32
G6



 463
R1
R36
G6



 464
R1
R39
G6



 465
R1
R45
G6



 466
R1
R49
G6



 467
R1
R55
G6



 468
R1
R57
G6



 469
R1
R58
G6



 470
R1
R60
G6



 471
R3
R31
G6



 472
R3
R32
G6



 473
R3
R36
G6



 474
R3
R39
G6



 475
R3
R45
G6



 476
R3
R49
G6



 477
R3
R55
G6



 478
R3
R57
G6



 479
R3
R58
G6



 480
R3
R60
G6



 481
R4
R31
G6



 482
R4
R32
G6



 483
R4
R36
G6



 484
R4
R39
G6



 485
R4
R45
G6



 486
R4
R49
G6



 487
R4
R55
G6



 488
R4
R57
G6



 489
R4
R58
G6



 490
R4
R60
G6



 491
R31
R31
G6



 492
R31
R32
G6



 493
R31
R36
G6



 494
R31
R39
G6



 495
R31
R45
G6



 496
R31
R49
G6



 497
R31
R55
G6



 498
R31
R57
G6



 499
R31
R58
G6



 500
R31
R60
G6



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R1
R31
G7



 502
R1
R32
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 503
R1
R36
G7



 504
R1
R39
G7



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R1
R45
G7



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R1
R49
G7



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R1
R55
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R1
R57
G7



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R1
R58
G7



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R1
R60
G7



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R3
R31
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R3
R32
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R3
R36
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R3
R39
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R3
R45
G7



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R3
R49
G7



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R3
R55
G7



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R3
R57
G7



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R3
R58
G7



 520
R3
R60
G7



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R4
R31
G7



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R4
R32
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R4
R36
G7



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R4
R39
G7



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R4
R45
G7



 526
R4
R49
G7



 527
R4
R55
G7



 528
R4
R57
G7



 529
R4
R58
G7



 530
R4
R60
G7



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R31
R31
G7



 532
R31
R32
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 533
R31
R36
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 534
R31
R39
G7



 535
R31
R45
G7



 536
R31
R49
G7



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R31
R55
G7



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R31
R57
G7



 539
R31
R58
G7



 540
R31
R60
G7



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R1
R31
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R1
R32
G8



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R1
R36
G8



 544
R1
R39
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 545
R1
R45
G8



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R1
R49
G8



 547
R1
R55
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R1
R57
G8



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R1
R58
G8



 550
R1
R60
G8



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R3
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R3
R32
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R3
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R3
R49
G8



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R3
R55
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R3
R57
G8



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R3
R58
G8



 560
R3
R60
G8



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R4
R31
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R4
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R4
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R4
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 565
R4
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R4
R49
G8



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R4
R55
G8



 568
R4
R57
G8



 569
R4
R58
G8



 570
R4
R60
G8



 571
R31
R31
G8



 572
R31
R32
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 573
R31
R36
G8



 574
R31
R39
G8



 575
R31
R45
G8



 576
R31
R49
G8



 577
R31
R55
G8



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R31
R57
G8



 579
R31
R58
G8



 580
R31
R60
G8



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R1
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R1
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R1
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R1
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G9



 585
R1
R45
G9



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R1
R49
G9



 587
R1
R55
G9



 588
R1
R57
G9



 589
R1
R58
G9



 590
R1
R60
G9



 591
R3
R31
G9



 592
R3
R32
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 593
R3
R36
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 594
R3
R39
G9



 595
R3
R45
G9



 596
R3
R49
G9



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R3
R55
G9



 598
R3
R57
G9



 599
R3
R58
G9



 600
R3
R60
G9



 601
R4
R31
G9



 602
R4
R32
G9



 603
R4
R36
G9



 604
R4
R39
G9



 605
R4
R45
G9



 606
R4
R49
G9



 607
R4
R55
G9



 608
R4
R57
G9



 609
R4
R58
G9



 610
R4
R60
G9



 611
R31
R31
G9



 612
R31
R32
G9



 613
R31
R36
G9



 614
R31
R39
G9



 615
R31
R45
G9



 616
R31
R49
G9



 617
R31
R55
G9



 618
R31
R57
G9



 619
R31
R58
G9



 620
R31
R60
G9



 621
R1
R31
G10



 622
R1
R32
G10



 623
R1
R36
G10



 624
R1
R39
G10



 625
R1
R45
G10



 626
R1
R49
G10



 627
R1
R55
G10



 628
R1
R57
G10



 629
R1
R58
G10



 630
R1
R60
G10



 631
R3
R31
G10



 632
R3
R32
G10



 633
R3
R36
G10



 634
R3
R39
G10



 635
R3
R45
G10



 636
R3
R49
G10



 637
R3
R55
G10



 638
R3
R57
G10



 639
R3
R58
G10



 640
R3
R60
G10



 641
R4
R31
G10



 642
R4
R32
G10



 643
R4
R36
G10



 644
R4
R39
G10



 645
R4
R45
G10



 646
R4
R49
G10



 647
R4
R55
G10



 648
R4
R57
G10



 649
R4
R58
G10



 650
R4
R60
G10



 651
R31
R31
G10



 652
R31
R32
G10



 653
R31
R36
G10



 654
R31
R39
G10



 655
R31
R45
G10



 656
R31
R49
G10



 657
R31
R55
G10



 658
R31
R57
G10



 659
R31
R58
G10



 660
R31
R60
G10



 661
R1
R31
G11



 662
R1
R32
G11



 663
R1
R36
G11



 664
R1
R39
G11



 665
R1
R45
G11



 666
R1
R49
G11



 667
R1
R55
G11



 668
R1
R57
G11



 669
R1
R58
G11



 670
R1
R60
G11



 671
R3
R31
G11



 672
R3
R32
G11



 673
R3
R36
G11



 674
R3
R39
G11



 675
R3
R45
G11



 676
R3
R49
G11



 677
R3
R55
G11



 678
R3
R57
G11



 679
R3
R58
G11



 680
R3
R60
G11



 681
R4
R31
G11



 682
R4
R32
G11



 683
R4
R36
G11



 684
R4
R39
G11



 685
R4
R45
G11



 686
R4
R49
G11



 687
R4
R55
G11



 688
R4
R57
G11



 689
R4
R58
G11



 690
R4
R60
G11



 691
R31
R31
G11



 692
R31
R32
G11



 693
R31
R36
G11



 694
R31
R39
G11



 695
R31
R45
G11



 696
R31
R49
G11



 697
R31
R55
G11



 698
R31
R57
G11



 699
R31
R58
G11



 700
R31
R60
G11



 701
R1
R31
G12



 702
R1
R32
G12



 703
R1
R36
G12



 704
R1
R39
G12



 705
R1
R45
G12



 706
R1
R49
G12



 707
R1
R55
G12



 708
R1
R57
G12



 709
R1
R58
G12



 710
R1
R60
G12



 711
R3
R31
G12



 712
R3
R32
G12



 713
R3
R36
G12



 714
R3
R39
G12



 715
R3
R45
G12



 716
R3
R49
G12



 717
R3
R55
G12



 718
R3
R57
G12



 719
R3
R58
G12



 720
R3
R60
G12



 721
R4
R31
G12



 722
R4
R32
G12



 723
R4
R36
G12



 724
R4
R39
G12



 725
R4
R45
G12



 726
R4
R49
G12



 727
R4
R55
G12



 728
R4
R57
G12



 729
R4
R58
G12



 730
R4
R60
G12



 731
R31
R31
G12



 732
R31
R32
G12



 733
R31
R36
G12



 734
R31
R39
G12



 735
R31
R45
G12



 736
R31
R49
G12



 737
R31
R55
G12



 738
R31
R57
G12



 739
R31
R58
G12



 740
R31
R60
G12



 741
R1
R31
G13



 742
R1
R32
G13



 743
R1
R36
G13



 744
R1
R39
G13



 745
R1
R45
G13



 746
R1
R49
G13



 747
R1
R55
G13



 748
R1
R57
G13



 749
R1
R58
G13



 750
R1
R60
G13



 751
R3
R31
G13



 752
R3
R32
G13



 753
R3
R36
G13



 754
R3
R39
G13



 755
R3
R45
G13



 756
R3
R49
G13



 757
R3
R55
G13



 758
R3
R57
G13



 759
R3
R58
G13



 760
R3
R60
G13



 761
R4
R31
G13



 762
R4
R32
G13



 763
R4
R36
G13



 764
R4
R39
G13



 765
R4
R45
G13



 766
R4
R49
G13



 767
R4
R55
G13



 768
R4
R57
G13



 769
R4
R58
G13



 770
R4
R60
G13



 771
R31
R31
G13



 772
R31
R32
G13



 773
R31
R36
G13



 774
R31
R39
G13



 775
R31
R45
G13



 776
R31
R49
G13



 777
R31
R55
G13



 778
R31
R57
G13



 779
R31
R58
G13



 780
R31
R60
G13



 781
R1
R31
G14



 782
R1
R32
G14



 783
R1
R36
G14



 784
R1
R39
G14



 785
R1
R45
G14



 786
R1
R49
G14



 787
R1
R55
G14



 788
R1
R57
G14



 789
R1
R58
G14



 790
R1
R60
G14



 791
R3
R31
G14



 792
R3
R32
G14



 793
R3
R36
G14



 794
R3
R39
G14



 795
R3
R45
G14



 796
R3
R49
G14



 797
R3
R55
G14



 798
R3
R57
G14



 799
R3
R58
G14



 800
R3
R60
G14



 801
R4
R31
G14



 802
R4
R32
G14



 803
R4
R36
G14



 804
R4
R39
G14



 805
R4
R45
G14



 806
R4
R49
G14



 807
R4
R55
G14



 808
R4
R57
G14



 809
R4
R58
G14



 810
R4
R60
G14



 811
R31
R31
G14



 812
R31
R32
G14



 813
R31
R36
G14



 814
R31
R39
G14



 815
R31
R45
G14



 816
R31
R49
G14



 817
R31
R55
G14



 818
R31
R57
G14



 819
R31
R58
G14



 820
R31
R60
G14



 821
R1
R31
G15



 822
R1
R32
G15



 823
R1
R36
G15



 824
R1
R39
G15



 825
R1
R45
G15



 826
R1
R49
G15



 827
R1
R55
G15



 828
R1
R57
G15



 829
R1
R58
G15



 830
R1
R60
G15



 831
R3
R31
G15



 832
R3
R32
G15



 833
R3
R36
G15



 834
R3
R39
G15



 835
R3
R45
G15



 836
R3
R49
G15



 837
R3
R55
G15



 838
R3
R57
G15



 839
R3
R58
G15



 840
R3
R60
G15



 841
R4
R31
G15



 842
R4
R32
G15



 843
R4
R36
G15



 844
R4
R39
G15



 845
R4
R45
G15



 846
R4
R49
G15



 847
R4
R55
G15



 848
R4
R57
G15



 849
R4
R58
G15



 850
R4
R60
G15



 851
R31
R31
G15



 852
R31
R32
G15



 853
R31
R36
G15



 854
R31
R39
G15



 855
R31
R45
G15



 856
R31
R49
G15



 857
R31
R55
G15



 858
R31
R57
G15



 859
R31
R58
G15



 860
R31
R60
G15



 861
R1
R31
G16



 862
R1
R32
G16



 863
R1
R36
G16



 864
R1
R39
G16



 865
R1
R45
G16



 866
R1
R49
G16



 867
R1
R55
G16



 868
R1
R57
G16



 869
R1
R58
G16



 870
R1
R60
G16



 871
R3
R31
G16



 872
R3
R32
G16



 873
R3
R36
G16



 874
R3
R39
G16



 875
R3
R45
G16



 876
R3
R49
G16



 877
R3
R55
G16



 878
R3
R57
G16



 879
R3
R58
G16



 880
R3
R60
G16



 881
R4
R31
G16



 882
R4
R32
G16



 883
R4
R36
G16



 884
R4
R39
G16



 885
R4
R45
G16



 886
R4
R49
G16



 887
R4
R55
G16



 888
R4
R57
G16



 889
R4
R58
G16



 890
R4
R60
G16



 891
R31
R31
G16



 892
R31
R32
G16



 893
R31
R36
G16



 894
R31
R39
G16



 895
R31
R45
G16



 896
R31
R49
G16



 897
R31
R55
G16



 898
R31
R57
G16



 899
R31
R58
G16



 900
R31
R60
G16



 901
R1
R31
G17



 902
R1
R32
G17



 903
R1
R36
G17



 904
R1
R39
G17



 905
R1
R45
G17



 906
R1
R49
G17



 907
R1
R55
G17



 908
R1
R57
G17



 909
R1
R58
G17



 910
R1
R60
G17



 911
R3
R31
G17



 912
R3
R32
G17



 913
R3
R36
G17



 914
R3
R39
G17



 915
R3
R45
G17



 916
R3
R49
G17



 917
R3
R55
G17



 918
R3
R57
G17



 919
R3
R58
G17



 920
R3
R60
G17



 921
R4
R31
G17



 922
R4
R32
G17



 923
R4
R36
G17



 924
R4
R39
G17



 925
R4
R45
G17



 926
R4
R49
G17



 927
R4
R55
G17



 928
R4
R57
G17



 929
R4
R58
G17



 930
R4
R60
G17



 931
R31
R31
G17



 932
R31
R32
G17



 933
R31
R36
G17



 934
R31
R39
G17



 935
R31
R45
G17



 936
R31
R49
G17



 937
R31
R55
G17



 938
R31
R57
G17



 939
R31
RS
G17



 940
R31
R60
G17



 941
R1
R31
G18



 942
R1
R32
G18



 943
R1
R36
G18



 944
R1
R39
G18



 945
R1
R45
G18



 946
R1
R49
G18



 947
R1
R55
G18



 948
R1
R57
G18



 949
R1
R58
G18



 950
R1
R60
G18



 951
R3
R31
G18



 952
R3
R32
G18



 953
R3
R36
G18



 954
R3
R39
G18



 955
R3
R45
G18



 956
R3
R49
G18



 957
R3
R55
G18



 958
R3
R57
G18



 959
R3
R58
G18



 960
R3
R60
G18



 961
R4
R31
G18



 962
R4
R32
G18



 963
R4
R36
G18



 964
R4
R39
G18



 965
R4
R45
G18



 966
R4
R49
G18



 967
R4
R55
G18



 968
R4
R57
G18



 969
R4
R58
G18



 970
R4
R60
G18



 971
R31
R31
G18



 972
R31
R32
G18



 973
R31
R36
G18



 974
R31
R39
G18



 975
R31
R45
G18



 976
R31
R49
G18



 977
R31
R55
G18



 978
R31
R57
G18



 979
R31
R58
G18



 980
R31
R60
G18



 981
R1
R31
G19



 982
R1
R32
G19



 983
R1
R36
G19



 984
R1
R39
G19



 985
R1
R45
G19



 986
R1
R49
G19



 987
R1
R55
G19



 988
R1
R57
G19



 989
R1
R58
G19



 990
R1
R60
G19



 991
R3
R31
G19



 992
R3
R32
G19



 993
R3
R36
G19



 994
R3
R39
G19



 995
R3
R45
G19



 996
R3
R49
G19



 997
R3
R55
G19



 998
R3
R57
G19



 999
R3
R58
G19



1000
R3
R60
G19



1001
R4
R31
G19



1002
R4
R32
G19



1003
R4
R36
G19



1004
R4
R39
G19



1005
R4
R45
G19



1006
R4
R49
G19



1007
R4
R55
G19



1008
R4
R57
G19



1009
R4
R58
G19



1010
R4
R60
G19



1011
R31
R31
G19



1012
R31
R32
G19



1013
R31
R36
G19



1014
R31
R39
G19



1015
R31
R45
G19



1016
R31
R49
G19



1017
R31
R55
G19



1018
R31
R57
G19



1019
R31
R58
G19



1020
R31
R60
G19



1021
R1
R31
G20



1022
R1
R32
G20



1023
R1
R36
G20



1024
R1
R39
G20



1025
R1
R45
G20



1026
R1
R49
G20



1027
R1
R55
G20



1028
R1
R57
G20



1029
R1
R58
G20



1030
R1
R60
G20



1031
R3
R31
G20



1032
R3
R32
G20



1033
R3
R36
G20



1034
R3
R39
G20



1035
R3
R45
G20



1036
R3
R49
G20



1037
R3
R55
G20



1038
R3
R57
G20



1039
R3
R58
G20



1040
R3
R60
G20



1041
R4
R31
G20



1042
R4
R32
G20



1043
R4
R36
G20



1044
R4
R39
G20



1045
R4
R45
G20



1046
R4
R49
G20



1047
R4
R55
G20



1048
R4
R57
G20



1049
R4
R58
G20



1050
R4
R60
G20



1051
R31
R31
G20



1052
R31
R32
G20



1053
R31
R36
G20



1054
R31
R39
G20



1055
R31
R45
G20



1056
R31
R49
G20



1057
R31
R55
G20



1058
R31
R57
G20



1059
R31
R58
G20



1060
R31
R60
G20



1061
R1
R31
G21



1062
R1
R32
G21



1063
R1
R36
G21



1064
R1
R39
G21



1065
R1
R45
G21



1066
R1
R49
G21



1067
R1
R55
G21



1068
R1
R57
G21



1069
R1
R58
G21



1070
R1
R60
G21



1071
R3
R31
G21



1072
R3
R32
G21



1073
R3
R36
G21



1074
R3
R39
G21



1075
R3
R45
G21



1076
R3
R49
G21



1077
R3
R55
G21



1078
R3
R57
G21



1079
R3
R58
G21



1080
R3
R60
G21



1081
R4
R31
G21



1082
R4
R32
G21



1083
R4
R36
G21



1084
R4
R39
G21



1085
R4
R45
G21



1086
R4
R49
G21



1087
R4
R55
G21



1088
R4
R57
G21



1089
R4
R58
G21



1090
R4
R60
G21



1091
R31
R31
G21



1092
R31
R32
G21



1093
R31
R36
G21



1094
R31
R39
G21



1095
R31
R45
G21



1096
R31
R49
G21



1097
R31
R55
G21



1098
R31
R57
G21



1099
R31
R58
G21



1100
R31
R60
G21



1101
R1
R31
G22



1102
R1
R32
G22



1103
R1
R36
G22



1104
R1
R39
G22



1105
R1
R45
G22



1106
R1
R49
G22



1107
R1
R55
G22



1108
R1
R57
G22



1109
R1
R58
G22



1110
R1
R60
G22



1111
R3
R31
G22



1112
R3
R32
G22



1113
R3
R36
G22



1114
R3
R39
G22



1115
R3
R45
G22



1116
R3
R49
G22



1117
R3
R55
G22



1118
R3
R57
G22



1119
R3
R58
G22



1120
R3
R60
G22



1121
R4
R31
G22



1122
R4
R32
G22



1123
R4
R36
G22



1124
R4
R39
G22



1125
R4
R45
G22



1126
R4
R49
G22



1127
R4
R55
G22



1128
R4
R57
G22



1129
R4
R58
G22



1130
R4
R60
G22



1131
R31
R31
G22



1132
R31
R32
G22



1133
R31
R36
G22



1134
R31
R39
G22



1135
R31
R45
G22



1136
R31
R49
G22



1137
R31
R55
G22



1138
R31
R57
G22



1139
R31
R58
G22



1140
R31
R60
G22



1141
R1
R31
G23



1142
R1
R32
G23



1143
R1
R36
G23



1144
R1
R39
G23



1145
R1
R45
G23



1146
R1
R49
G23



1147
R1
R55
G23



1148
R1
R57
G23



1149
R1
R58
G23



1150
R1
R60
G23



1151
R3
R31
G23



1152
R3
R32
G23



1153
R3
R36
G23



1154
R3
R39
G23



1155
R3
R45
G23



1156
R3
R49
G23



1157
R3
R55
G23



1158
R3
R57
G23



1159
R3
R58
G23



1160
R3
R60
G23



1161
R4
R31
G23



1162
R4
R32
G23



1163
R4
R36
G23



1164
R4
R39
G23



1165
R4
R45
G23



1166
R4
R49
G23



1167
R4
R55
G23



1168
R4
R57
G23



1169
R4
R58
G23



1170
R4
R60
G23



1171
R31
R31
G23



1172
R31
R32
G23



1173
R31
R36
G23



1174
R31
R39
G23



1175
R31
R45
G23



1176
R31
R49
G23



1177
R31
R55
G23



1178
R31
R57
G23



1179
R31
R58
G23



1180
R31
R60
G23



1181
R1
R31
G24



1182
R1
R32
G24



1183
R1
R36
G24



1184
R1
R39
G24



1185
R1
R45
G24



1186
R1
R49
G24



1187
R1
R55
G24



1188
R1
R57
G24



1189
R1
R58
G24



1190
R1
R60
G24



1191
R3
R31
G24



1192
R3
R32
G24



1193
R3
R36
G24



1194
R3
R39
G24



1195
R3
R45
G24



1196
R3
R49
G24



1197
R3
R55
G24



1198
R3
R57
G24



1199
R3
R58
G24



1200
R3
R60
G24



1201
R4
R31
G24



1202
R4
R32
G24



1203
R4
R36
G24



1204
R4
R39
G24



1205
R4
R45
G24



1206
R4
R49
G24



1207
R4
R55
G24



1208
R4
R57
G24



1209
R4
R58
G24



1210
R4
R60
G24



1211
R31
R31
G24



1212
R31
R32
G24



1213
R31
R36
G24



1214
R31
R39
G24



1215
R31
R45
G24



1216
R31
R49
G24



1217
R31
R55
G24



1218
R31
R57
G24



1219
R31
R58
G24



1220
R31
R60
G24



1221
R1
R31
G25



1222
R1
R32
G25



1223
R1
R36
G25



1224
R1
R39
G25



1225
R1
R45
G25



1226
R1
R49
G25



1227
R1
R55
G25



1228
R1
R57
G25



1229
R1
R58
G25



1230
R1
R60
G25



1231
R3
R31
G25



1232
R3
R32
G25



1233
R3
R36
G25



1234
R3
R39
G25



1235
R3
R45
G25



1236
R3
R49
G25



1237
R3
R55
G25



1238
R3
R57
G25



1239
R3
R58
G25



1240
R3
R60
G25



1241
R4
R31
G25



1242
R4
R32
G25



1243
R4
R36
G25



1244
R4
R39
G25



1245
R4
R45
G25



1246
R4
R49
G25



1247
R4
R55
G25



1248
R4
R57
G25



1249
R4
R58
G25



1250
R4
R60
G25



1251
R31
R31
G25



1252
R31
R32
G25



1253
R31
R36
G25



1254
R31
R39
G25



1255
R31
R45
G25



1256
R31
R49
G25



1257
R31
R55
G25



1258
R31
R57
G25



1259
R31
R58
G25



1260
R31
R60
G25



1261
R1
R31
G26



1262
R1
R32
G26



1263
R1
R36
G26



1264
R1
R39
G26



1265
R1
R45
G26



1266
R1
R49
G26



1267
R1
R55
G26



1268
R1
R57
G26



1269
R1
R58
G26



1270
R1
R60
G26



1271
R3
R31
G26



1272
R3
R32
G26



1273
R3
R36
G26



1274
R3
R39
G26



1275
R3
R45
G26



1276
R3
R49
G26



1277
R3
R55
G26



1278
R3
R57
G26



1279
R3
R58
G26



1280
R3
R60
G26



1281
R4
R31
G26



1282
R4
R32
G26



1283
R4
R36
G26



1284
R4
R39
G26



1285
R4
R45
G26



1286
R4
R49
G26



1287
R4
R55
G26



1288
R4
R57
G26



1289
R4
R58
G26



1290
R4
R60
G26



1291
R31
R31
G26



1292
R31
R32
G26



1293
R31
R36
G26



1294
R31
R39
G26



1295
R31
R45
G26



1296
R31
R49
G26



1297
R31
R55
G26



1298
R31
R57
G26



1299
R31
R58
G26



1300
R31
R60
G26



1301
R1
R31
G27



1302
R1
R32
G27



1303
R1
R36
G27



1304
R1
R39
G27



1305
R1
R45
G27



1306
R1
R49
G27



1307
R1
R55
G27



1308
R1
R57
G27



1309
R1
R58
G27



1310
R1
R60
G27



1311
R3
R31
G27



1312
R3
R32
G27



1313
R3
R36
G27



1314
R3
R39
G27



1315
R3
R45
G27



1316
R3
R49
G27



1317
R3
R55
G27



1318
R3
R57
G27



1319
R3
R58
G27



1320
R3
R60
G27



1321
R4
R31
G27



1322
R4
R32
G27



1323
R4
R36
G27



1324
R4
R39
G27



1325
R4
R45
G27



1326
R4
R49
G27



1327
R4
R55
G27



1328
R4
R57
G27



1329
R4
R58
G27



1330
R4
R60
G27



1331
R31
R31
G27



1332
R31
R32
G27



1333
R31
R36
G27



1334
R31
R39
G27



1335
R31
R45
G27



1336
R31
R49
G27



1337
R31
R55
G27



1338
R31
R57
G27



1339
R31
R58
G27



1340
R31
R60
G27



1341
R1
R31
G29



1342
R1
R32
G29



1343
R1
R36
G29



1344
R1
R39
G29



1345
R1
R45
G29



1346
R1
R49
G29



1347
R1
R55
G29



1348
R1
R57
G29



1349
R1
R58
G29



1350
R1
R60
G29



1351
R3
R31
G29



1352
R3
R32
G29



1353
R3
R36
G29



1354
R3
R39
G29



1355
R3
R45
G29



1356
R3
R49
G29



1357
R3
R55
G29



1358
R3
R57
G29



1359
R3
R58
G29



1360
R3
R60
G29



1361
R4
R31
G29



1362
R4
R32
G29



1363
R4
R36
G29



1364
R4
R39
G29



1365
R4
R45
G29



1366
R4
R49
G29



1367
R4
R55
G29



1368
R4
R57
G29



1369
R4
R58
G29



1370
R4
R60
G29



1371
R31
R31
G29



1372
R31
R32
G29



1373
R31
R36
G29



1374
R31
R39
G29



1375
R31
R45
G29



1376
R31
R49
G29



1377
R31
R55
G29



1378
R31
R57
G29



1379
R31
R58
G29



1380
R31
R60
G29



1381
R1
R31
G30



1382
R1
R32
G30



1383
R1
R36
G30



1384
R1
R39
G30



1385
R1
R45
G30



1386
R1
R49
G30



1387
R1
R55
G30



1388
R1
R57
G30



1389
R1
R58
G30



1390
R1
R60
G30



1391
R3
R31
G30



1392
R3
R32
G30



1393
R3
R36
G30



1394
R3
R39
G30



1395
R3
R45
G30



1396
R3
R49
G30



1397
R3
R55
G30



1398
R3
R57
G30



1399
R3
R58
G30



1400
R3
R60
G30



1401
R4
R31
G30



1402
R4
R32
G30



1403
R4
R36
G30



1404
R4
R39
G30



1405
R4
R45
G30



1406
R4
R49
G30



1407
R4
R55
G30



1408
R4
R57
G30



1409
R4
R58
G30



1410
R4
R60
G30



1411
R31
R31
G30



1412
R31
R32
G30



1413
R31
R36
G30



1414
R31
R39
G30



1415
R31
R45
G30



1416
R31
R49
G30



1417
R31
R55
G30



1418
R31
R57
G30



1419
R31
R58
G30



1420
R31
R60
G30



1421
R1
R31
G31



1422
R1
R32
G31



1423
R1
R36
G31



1424
R1
R39
G31



1425
R1
R45
G31



1426
R1
R49
G31



1427
R1
R55
G31



1428
R1
R57
G31



1429
R1
R58
G31



1430
R1
R60
G31



1431
R3
R31
G31



1432
R3
R32
G31



1433
R3
R36
G31



1434
R3
R39
G31



1435
R3
R45
G31



1436
R3
R49
G31



1437
R3
R55
G31



1438
R3
R57
G31



1439
R3
R58
G31



1440
R3
R60
G31



1441
R4
R31
G31



1442
R4
R32
G31



1443
R4
R36
G31



1444
R4
R39
G31



1445
R4
R45
G31



1446
R4
R49
G31



1447
R4
R55
G31



1448
R4
R57
G31



1449
R4
R58
G31



1450
R4
R60
G31



1451
R31
R31
G31



1452
R31
R32
G31



1453
R31
R36
G31



1454
R31
R39
G31



1455
R31
R45
G31



1456
R31
R49
G31



1457
R31
R55
G31



1458
R31
R57
G31



1459
R31
R58
G31



1460
R31
R60
G31



1461
R1
R31
G32



1462
R1
R32
G32



1463
R1
R36
G32



1464
R1
R39
G32



1465
R1
R45
G32



1466
R1
R49
G32



1467
R1
R55
G32



1468
R1
R57
G32



1469
R1
R58
G32



1470
R1
R60
G32



1471
R3
R31
G32



1472
R3
R32
G32



1473
R3
R36
G32



1474
R3
R39
G32



1475
R3
R45
G32



1476
R3
R49
G32



1477
R3
R55
G32



1478
R3
R57
G32



1479
R3
R58
G32



1480
R3
R60
G32



1481
R4
R31
G32



1482
R4
R32
G32



1483
R4
R36
G32



1484
R4
R39
G32



1485
R4
R45
G32



1486
R4
R49
G32



1487
R4
R55
G32



1488
R4
R57
G32



1489
R4
R58
G32



1490
R4
R60
G32



1491
R31
R31
G32



1492
R31
R32
G32



1493
R31
R36
G32



1494
R31
R39
G32



1495
R31
R45
G32



1496
R31
R49
G32



1497
R31
R55
G32



1498
R31
R57
G32



1499
R31
R58
G32



1500
R31
R60
G32










wherein:


R1 to R60 have the structures defined in the following LIST 5:




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wherein G1 to G32 have the structures defined in the following LIST 6:




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with the proviso that when m is 1 or 2, G cannot be G27, G28, G29, G30, G31, or G32.


In some embodiments, the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); and wherein LA, LB, and LC are different from each other.


In some embodiments, LB is a substituted or unsubstituted phenylpyridine, and LC is a substituted or unsubstituted acetylacetonate.


In some embodiments, LB and LC are each independently selected from the group consisting of the structures of the following LIST 7:




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wherein T is selected from the group consisting of B, Al, Ga, and In;


wherein K1′ is a direct bond or is selected from the group consisting of NRe, PRe, O, S, and Se;


wherein each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;


wherein Y′ is selected from the group consisting of BRe, BReRf, NRe, PRe, P(O)Re, O, S, Se, C═O, C═S, C═Se, C═NRe, C═CReRf, S═O, SO2, CReRf, SiReRf, and GeReRf;


wherein Re and Rf can be fused or joined to form a ring;


wherein each Ra, Rb, Rc, and Rd can independently represent from mono to the maximum possible number of substitutions, or no substitution;


wherein each Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, Rd, Re, and Rf is independently a hydrogen or a substituent selected from the group consisting of the General Substituents as defined herein; and


wherein any two Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, and Rd can be fused or joined to form a ring or form a multidentate ligand.


In some embodiments, LB and LC are each independently selected from the group consisting of the structures of the following LIST 8:




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wherein:


Ra′, Rb′, and Rc′ each independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;


each of Ra1, Rb1, Rc1, RN, Ra′, Rb′, and Rc′ is independently hydrogen or a substituent selected from the group consisting of the General Substituents defined herein; and


any two of Ra1, Rb1, Rc1, RN, Ra′, Rb′, and Rc′ can be fused or joined to form a ring or form a multidentate ligand.


In some embodiments, the compound can have the formula Ir(LA)3, the formula Ir(LA)(LBk)2, the formula Ir(LA)2(LBk), the formula Ir(LA)2(LCj-I), the formula Ir(LA)2(LCj-II), the formula Ir(LA)(LBk)(LCj-I), or the formula Ir(LA)(LBk)(LCj-II), wherein LA is a ligand with respect to Formula I as defined here; LBk is defined herein; and LCj-I and LCj-II are each defined herein.


In some embodiments, LA can be selected from LAi-m, wherein i is an integer from 1 to 1500; m is an integer from 1 to 45; LB can be selected from LBk, wherein k is an integer from 1 to 324; and LC can be selected from LCj-I and LCj-II, wherein j is an integer from 1 to 1416,


wherein:


when the compound has formula Ir(LAi-m)(LAs-n)(LAt-o), wherein s and t are each independently an integer from 1 to 1500, and n and o are each independently an integer from 1 to 45; and the compound is selected from the group consisting of Ir(LA1-1)(LA2-1)2 to Ir(LA1500-45)(LA1499-45)2, Ir(LA1-1)2(LA2-1) to Ir(LA1500-45)2(LA1499-45), Ir(LA1-1)(LA2-1)(LA3-1) to Ir(LA1500-45)(LA1499-45)(LA1498-45), Ir(LA1-1)(LA1-2)2 to Ir(LA1500-45)(LA1500-44)2, Ir(LA1-1)2(LA1-2) to Ir(LA1500-45)2(LA1500-44), and Ir(LA1-1)(LA1-2) (LA1-3) to Ir(LA1500-43)(LA1500-44) (LA1500-45), with the proviso that at least two of i, s, and t are different in the same formula, or at least two of m, n, and o are different in the same formula. In other words, each of i, s, and t can independently be an integer from 1 to 1500 and each of m, n, and o can independently be an integer from 1 to 45, so long as LAi-m, LAs-n, and LAt-o are different;


when the compound has formula Ir(LAi-m)(LBk)(LCj-I), the compound is selected from the group consisting of Ir(LA1-1)(LB1)(LC1-I) to Ir(LA1500-45)(LB324)(LC1416-I);


when the compound has formula Ir(LAi-m)(LBk)(LCj-II), the compound is selected from the group consisting of Ir(LA1-1)(LB1)(LC1-I) to Ir(LA1500-45)(LB324)(LC1416-I);


when the compound has formula Ir(LAi-m)2(LCj-1), the compound is selected from the group consisting of Ir(LA1-1)2(LC1-I) to Ir(LA1500-45)2(LC1416-I); and


when the compound has formula Ir(LAi-m)2(LCj-II), the compound is selected from the group consisting of Ir(LA1-1)2(LC1-II) to Ir(LA1500-45)2(LC1416-II);


wherein LB1 to LB324 have the structures defined in the following LIST 9:




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wherein each LCj-I has a structure based on formula




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and


each LCj-II has a structure based on formula




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wherein for each LCj in LCj-I and LCj-II, R201 and R202 are each independently defined in the following LIST 10:

















LCj
R201
R202









LC1
RD1
RD1



LC2
RD2
RD2



LC3
RD3
RD3



LC4
RD4
RD4



LC5
RD5
RD5



LC6
RD6
RD6



LC7
RD7
RD7



LC8
RD8
RD8



LC9
RD9
RD9



LC10
RD10
RD10



LC11
RD11
RD11



LC12
RD12
RD12



LC13
RD13
RD13



LC14
RD14
RD14



LC15
RD15
RD15



LC16
RD16
RD16



LC17
RD17
RD17



LC18
RD18
RD18



LC19
RD19
RD19



LC20
RD20
RD20



LC21
RD21
RD21



LC22
RD22
RD22



LC23
RD23
RD23



LC24
RD24
RD24



LC25
RD25
RD25



LC26
RD26
RD26



LC27
RD27
RD27



LC28
RD28
RD28



LC29
RD29
RD29



LC30
RD30
RD30



LC31
RD31
RD31



LC32
RD32
RD32



LC33
RD33
RD33



LC34
RD34
RD34



LC35
RD35
RD35



LC36
RD36
RD36



LC37
RD37
RD37



LC38
RD38
RD38



LC39
RD39
RD39



LC40
RD40
RD40



LC41
RD41
RD41



LC42
RD42
RD42



LC43
RD43
RD43



LC44
RD44
RD44



LC45
RD45
RD45



LC46
RD46
RD46



LC47
RD47
RD47



LC48
RD48
RD48



LC49
RD49
RD49



LC50
RD50
RD50



LC51
RD51
RD51



LC52
RD52
RD52



LC53
RD53
RD53



LC54
RD54
RD54



LC55
RD55
RD55



LC56
RD56
RD56



LC57
RD57
RD57



LC58
RD58
RD58



LC59
RD59
RD59



LC60
RD60
RD60



LC61
RD61
RD61



LC62
RD62
RD62



LC63
RD63
RD63



LC64
RD64
RD64



LC65
RD65
RD65



LC66
RD66
RD66



LC67
RD67
RD67



LC68
RD68
RD68



LC69
RD69
RD69



LC70
RD70
RD70



LC71
RD71
RD71



LC72
RD72
RD72



LC73
RD73
RD73



LC74
RD74
RD74



LC75
RD75
RD75



LC76
RD76
RD76



LC77
RD77
RD77



LC78
RD78
RD78



LC79
RD79
RD79



LC80
RD80
RD80



LC81
RD81
RD81



LC82
RD82
RD82



LC83
RD83
RD83



LC84
RD84
RD84



LC85
RD85
RD85



LC86
RD86
RD86



LC87
RD87
RD87



LC88
RD88
RD88



LC89
RD89
RD89



LC90
RD90
RD90



LC91
RD91
RD91



LC92
RD92
RD92



LC93
RD93
RD93



LC94
RD94
RD94



LC95
RD95
RD95



LC96
RD96
RD96



LC97
RD97
RD97



LC98
RD98
RD98



LC99
RD99
RD99



LC100
RD100
RD100



LC101
RD101
RD101



LC102
RD102
RD102



LC103
RD103
RD103



LC104
RD104
RD104



LC105
RD105
RD105



LC106
RD106
RD106



LC107
RD107
RD107



LC108
RD108
RD108



LC109
RD109
RD109



LC110
RD110
RD110



LC111
RD111
RD111



LC112
RD112
RD112



LC113
RD113
RD113



LC114
RD114
RD114



LC115
RD115
RD115



LC116
RD116
RD116



LC117
RD117
RD117



LC118
RD118
RD118



LC119
RD119
RD119



LC120
RD120
RD120



LC121
RD121
RD121



LC122
RD122
RD122



LC123
RD123
RD123



LC124
RD124
RD124



LC125
RD125
RD125



LC126
RD126
RD126



LC127
RD127
RD127



LC128
RD128
RD128



LC129
RD129
RD129



LC130
RD130
RD130



LC131
RD131
RD131



LC132
RD132
RD132



LC133
RD133
RD133



LC134
RD134
RD134



LC135
RD135
RD135



LC136
RD136
RD136



LC137
RD137
RD137



LC138
RD138
RD138



LC139
RD139
RD139



LC140
RD140
RD140



LC141
RD141
RD141



LC142
RD142
RD142



LC143
RD143
RD143



LC144
RD144
RD144



LC145
RD145
RD145



LC146
RD146
RD146



LC147
RD147
RD147



LC148
RD148
RD148



LC149
RD149
RD149



LC150
RD150
RD150



LC151
RD151
RD151



LC152
RD152
RD152



LC153
RD153
RD153



LC154
RD154
RD154



LC155
RD155
RD155



LC156
RD156
RD156



LC157
RD157
RD157



LC158
RD158
RD158



LC159
RD159
RD159



LC160
RD160
RD160



LC161
RD161
RD161



LC162
RD162
RD162



LC163
RD163
RD163



LC164
RD164
RD164



LC165
RD165
RD165



LC166
RD166
RD166



LC167
RD167
RD167



LC168
RD168
RD168



LC169
RD169
RD169



LC170
RD170
RD170



LC171
RD171
RD171



LC172
RD172
RD172



LC173
RD173
RD173



LC174
RD174
RD174



LC175
RD175
RD175



LC176
RD176
RD176



LC177
RD177
RD177



LC178
RD178
RD178



LC179
RD179
RD179



LC180
RD180
RD180



LC181
RD181
RD181



LC182
RD182
RD182



LC183
RD183
RD183



LC184
RD184
RD184



LC185
RD185
RD185



LC186
RD186
RD186



LC187
RD187
RD187



LC188
RD188
RD188



LC189
RD189
RD189



LC190
RD190
RD190



LC191
RD191
RD191



LC192
RD192
RD192



LC193
RD1
RD3



LC194
RD1
RD4



LC195
RD1
RD5



LC196
RD1
RD9



LC197
RD1
RD10



LC198
RD1
RD17



LC199
RD1
RD18



LC200
RD1
RD20



LC201
RD1
RD22



LC202
RD1
RD37



LC203
RD1
RD40



LC204
RD1
RD41



LC205
RD1
RD42



LC206
RD1
RD43



LC207
RD1
RD48



LC208
RD1
RD49



LC209
RD1
RD50



LC210
RD1
RD54



LC211
RD1
RD55



LC212
RD1
RD58



LC213
RD1
RD59



LC214
RD1
RD78



LC215
RD1
RD79



LC216
RD1
RD81



LC217
RD1
RD87



LC218
RD1
RD88



LC219
RD1
RD89



LC220
RD1
RD93



LC221
RD1
RD116



LC222
RD1
RD117



LC223
RD1
RD118



LC224
RD1
RD119



LC225
RD1
RD120



LC226
RD1
RD133



LC227
RD1
RD134



LC228
RD1
RD135



LC229
RD1
RD136



LC230
RD1
RD143



LC231
RD1
RD144



LC232
RD1
RD145



LC233
RD1
RD146



LC234
RD1
RD147



LC235
RD1
RD149



LC236
RD1
RD151



LC237
RD1
RD154



LC238
RD1
RD155



LC239
RD1
RD161



LC240
RD1
RD175



LC241
RD4
RD3



LC242
RD4
RD5



LC243
RD4
RD9



LC244
RD4
RD10



LC245
RD4
RD17



LC246
RD4
RD18



LC247
RD4
RD20



LC248
RD4
RD22



LC249
RD4
RD37



LC250
RD4
RD40



LC251
RD4
RD41



LC252
RD4
RD42



LC253
RD4
RD43



LC254
RD4
RD48



LC255
RD4
RD49



LC256
RD4
RD50



LC257
RD4
RD54



LC258
RD4
RD55



LC259
RD4
RD58



LC260
RD4
RD59



LC261
RD4
RD78



LC262
RD4
RD79



LC263
RD4
RD81



LC264
RD4
RD87



LC265
RD4
RD88



LC266
RD4
RD89



LC267
RD4
RD93



LC268
RD4
RD116



LC269
RD4
RD117



LC270
RD4
RD118



LC271
RD4
RD119



LC272
RD4
RD120



LC273
RD4
RD133



LC274
RD4
RD134



LC275
RD4
RD135



LC276
RD4
RD136



LC277
RD4
RD143



LC278
RD4
RD144



LC279
RD4
RD145



LC280
RD4
RD146



LC281
RD4
RD147



LC282
RD4
RD149



LC283
RD4
RD151



LC284
RD4
RD154



LC285
RD4
RD155



LC286
RD4
RD161



LC287
RD4
RD175



LC288
RD9
RD3



LC289
RD9
RD5



LC290
RD9
RD10



LC291
RD9
RD17



LC292
RD9
RD18



LC293
RD9
RD20



LC294
RD9
RD22



LC295
RD9
RD37



LC296
RD9
RD40



LC297
RD9
RD41



LC298
RD9
RD42



LC299
RD9
RD43



LC300
RD9
RD48



LC301
RD9
RD49



LC302
RD9
RD50



LC303
RD9
RD54



LC304
RD9
RD55



LC305
RD9
RD58



LC306
RD9
RD59



LC307
RD9
RD78



LC308
RD9
RD79



LC309
RD9
RD81



LC310
RD9
RD87



LC311
RD9
RD88



LC312
RD9
RD89



LC313
RD9
RD93



LC314
RD9
RD116



LC315
RD9
RD117



LC316
RD9
RD118



LC317
RD9
RD119



LC318
RD9
RD120



LC319
RD9
RD133



LC320
RD9
RD134



LC321
RD9
RD135



LC322
RD9
RD136



LC323
RD9
RD143



LC324
RD9
RD144



LC325
RD9
RD145



LC326
RD9
RD146



LC327
RD9
RD147



LC328
RD9
RD149



LC329
RD9
RD151



LC330
RD9
RD154



LC331
RD9
RD155



LC332
RD9
RD161



LC333
RD9
RD175



LC334
RD10
RD3



LC335
RD10
RD5



LC336
RD10
RD17



LC337
RD10
RD18



LC338
RD10
RD20



LC339
RD10
RD22



LC340
RD10
RD37



LC341
RD10
RD40



LC342
RD10
RD41



LC343
RD10
RD42



LC344
RD10
RD43



LC345
RD10
RD48



LC346
RD10
RD49



LC347
RD10
RD50



LC348
RD10
RD54



LC349
RD10
RD55



LC350
RD10
RD58



LC351
RD10
RD59



LC352
RD10
RD78



LC353
RD10
RD79



LC354
RD10
RD81



LC355
RD10
RD87



LC356
RD10
RD88



LC357
RD10
RD89



LC358
RD10
RD93



LC359
RD10
RD116



LC360
RD10
RD117



LC361
RD10
RD118



LC362
RD10
RD119



LC363
RD10
RD120



LC364
RD10
RD133



LC365
RD10
RD134



LC366
RD10
RD135



LC367
RD10
RD136



LC368
RD10
RD143



LC369
RD10
RD144



LC370
RD10
RD145



LC371
RD10
RD146



LC372
RD10
RD147



LC373
RD10
RD149



LC374
RD10
RD151



LC375
RD10
RD154



LC376
RD10
RD155



LC377
RD10
RD161



LC378
RD10
RD175



LC379
RD17
RD3



LC380
RD17
RD5



LC381
RD17
RD18



LC382
RD17
RD20



LC383
RD17
RD22



LC384
RD17
RD37



LC385
RD17
RD40



LC386
RD17
RD41



LC387
RD17
RD42



LC388
RD17
RD43



LC389
RD17
RD48



LC390
RD17
RD49



LC391
RD17
RD50



LC392
RD17
RD54



LC393
RD17
RD55



LC394
RD17
RD58



LC395
RD17
RD59



LC396
RD17
RD78



LC397
RD17
RD79



LC398
RD17
RD81



LC399
RD17
RD87



LC400
RD17
RD88



LC401
RD17
RD89



LC402
RD17
RD93



LC403
RD17
RD116



LC404
RD17
RD117



LC405
RD17
RD118



LC406
RD17
RD119



LC407
RD17
RD120



LC408
RD17
RD133



LC409
RD17
RD134



LC410
RD17
RD135



LC411
RD17
RD136



LC412
RD17
RD143



LC413
RD17
RD144



LC414
RD17
RD145



LC415
RD17
RD146



LC416
RD17
RD147



LC417
RD17
RD149



LC418
RD17
RD151



LC419
RD17
RD154



LC420
RD17
RD155



LC421
RD17
RD161



LC422
RD17
RD175



LC423
RD50
RD3



LC424
RD50
RD5



LC425
RD50
RD18



LC426
RD50
RD20



LC427
RD50
RD22



LC428
RD50
RD37



LC429
RD50
RD40



LC430
RD50
RD41



LC431
RD50
RD42



LC432
RD50
RD43



LC433
RD50
RD48



LC434
RD50
RD49



LC435
RD50
RD54



LC436
RD50
RD55



LC437
RD50
RD58



LC438
RD50
RD59



LC439
RD50
RD78



LC440
RD50
RD79



LC441
RD50
RD81



LC442
RD50
RD87



LC443
RD50
RD88



LC444
RD50
RD89



LC445
RD50
RD93



LC446
RD50
RD116



LC447
RD50
RD117



LC448
RD50
RD118



LC449
RD50
RD119



LC450
RD50
RD120



LC451
RD50
RD133



LC452
RD50
RD134



LC453
RD50
RD135



LC454
RD50
RD136



LC455
RD50
RD143



LC456
RD50
RD144



LC457
RD50
RD145



LC458
RD50
RD146



LC459
RD50
RD147



LC460
RD50
RD149



LC461
RD50
RD151



LC462
RD50
RD154



LC463
RD50
RD155



LC464
RD50
RD161



LC465
RD50
RD175



LC466
RD55
RD3



LC467
RD55
RD5



LC468
RD55
RD18



LC469
RD55
RD20



LC470
RD55
RD22



LC471
RD55
RD37



LC472
RD55
RD40



LC473
RD55
RD41



LC474
RD55
RD42



LC475
RD55
RD43



LC476
RD55
RD48



LC477
RD55
RD49



LC478
RD55
RD54



LC479
RD55
RD58



LC480
RD55
RD59



LC481
RD55
RD78



LC482
RD55
RD79



LC483
RD55
RD81



LC484
RD55
RD87



LC485
RD55
RD88



LC486
RD55
RD89



LC487
RD55
RD93



LC488
RD55
RD116



LC489
RD55
RD117



LC490
RD55
RD118



LC491
RD55
RD119



LC492
RD55
RD120



LC493
RD55
RD133



LC494
RD55
RD134



LC495
RD55
RD135



LC496
RD55
RD136



LC497
RD55
RD143



LC498
RD55
RD144



LC499
RD55
RD145



LC500
RD55
RD146



LC501
RD55
RD147



LC502
RD55
RD149



LC503
RD55
RD151



LC504
RD55
RD154



LC505
RD55
RD155



LC506
RD55
RD161



LC507
RD55
RD175



LC508
RD116
RD3



LC509
RD116
RD5



LC510
RD116
RD17



LC511
RD116
RD18



LC512
RD116
RD20



LC513
RD116
RD22



LC514
RD116
RD37



LC515
RD116
RD40



LC516
RD116
RD41



LC517
RD116
RD42



LC518
RD116
RD43



LC519
RD116
RD48



LC520
RD116
RD49



LC521
RD116
RD54



LC522
RD116
RD58



LC523
RD116
RD59



LC524
RD116
RD78



LC525
RD116
RD79



LC526
RD116
RD81



LC527
RD116
RD87



LC528
RD116
RD88



LC529
RD116
RD89



LC530
RD116
RD93



LC531
RD116
RD117



LC532
RD116
RD118



LC533
RD116
RD119



LC534
RD116
RD120



LC535
RD116
RD133



LC536
RD116
RD134



LC537
RD116
RD135



LC538
RD116
RD136



LC539
RD116
RD143



LC540
RD116
RD144



LC541
RD116
RD145



LC542
RD116
RD146



LC543
RD116
RD147



LC544
RD116
RD149



LC545
RD116
RD151



LC546
RD116
RD154



LC547
RD116
RD155



LC548
RD116
RD161



LC549
RD116
RD175



LC550
RD143
RD3



LC551
RD143
RD5



LC552
RD143
RD17



LC553
RD143
RD18



LC554
RD143
RD20



LC555
RD143
RD22



LC556
RD143
RD37



LC557
RD143
RD40



LC558
RD143
RD41



LC559
RD143
RD42



LC560
RD143
RD43



LC561
RD143
RD48



LC562
RD143
RD49



LC563
RD143
RD54



LC564
RD143
RD58



LC565
RD143
RD59



LC566
RD143
RD78



LC567
RD143
RD79



LC568
RD143
RD81



LC569
RD143
RD87



LC570
RD143
RD88



LC571
RD143
RD89



LC572
RD143
RD93



LC573
RD143
RD116



LC574
RD143
RD117



LC575
RD143
RD118



LC576
RD143
RD119



LC577
RD143
RD120



LC578
RD143
RD133



LC579
RD143
RD134



LC580
RD143
RD135



LC581
RD143
RD136



LC582
RD143
RD144



LC583
RD143
RD145



LC584
RD143
RD146



LC585
RD143
RD147



LC586
RD143
RD149



LC587
RD143
RD151



LC588
RD143
RD154



LC589
RD143
RD155



LC590
RD143
RD161



LC591
RD143
RD175



LC592
RD144
RD3



LC593
RD144
RD5



LC594
RD144
RD17



LC595
RD144
RD18



LC596
RD144
RD20



LC597
RD144
RD22



LC598
RD144
RD37



LC599
RD144
RD40



LC600
RD144
RD41



LC601
RD144
RD42



LC602
RD144
RD43



LC603
RD144
RD48



LC604
RD144
RD49



LC605
RD144
RD54



LC606
RD144
RD58



LC607
RD144
RD59



LC608
RD144
RD78



LC609
RD144
RD79



LC610
RD144
RD81



LC611
RD144
RD87



LC612
RD144
RD88



LC613
RD144
RD89



LC614
RD144
RD93



LC615
RD144
RD116



LC616
RD144
RD117



LC617
RD144
RD118



LC618
RD144
RD119



LC619
RD144
RD120



LC620
RD144
RD133



LC621
RD144
RD134



LC622
RD144
RD135



LC623
RD144
RD136



LC624
RD144
RD145



LC625
RD144
RD146



LC626
RD144
RD147



LC627
RD144
RD149



LC628
RD144
RD151



LC629
RD144
RD154



LC630
RD144
RD155



LC631
RD144
RD161



LC632
RD144
RD175



LC633
RD145
RD3



LC634
RD145
RD5



LC635
RD145
RD17



LC636
RD145
RD18



LC637
RD145
RD20



LC638
RD145
RD22



LC639
RD145
RD37



LC640
RD145
RD40



LC641
RD145
RD41



LC642
RD145
RD42



LC643
RD145
RD43



LC644
RD145
RD48



LC645
RD145
RD49



LC646
RD145
RD54



LC647
RD145
RD58



LC648
RD145
RD59



LC649
RD145
RD78



LC650
RD145
RD79



LC651
RD145
RD81



LC652
RD145
RD87



LC653
RD145
RD88



LC654
RD145
RD89



LC655
RD145
RD93



LC656
RD145
RD116



LC657
RD145
RD117



LC658
RD145
RD118



LC659
RD145
RD119



LC660
RD145
RD120



LC661
RD145
RD133



LC662
RD145
RD134



LC663
RD145
RD135



LC664
RD145
RD136



LC665
RD145
RD146



LC666
RD145
RD147



LC667
RD145
RD149



LC668
RD145
RD151



LC669
RD145
RD154



LC670
RD145
RD155



LC671
RD145
RD161



LC672
RD145
RD175



LC673
RD146
RD3



LC674
RD146
RD5



LC675
RD146
RD17



LC676
RD146
RD18



LC677
RD146
RD20



LC678
RD146
RD22



LC679
RD146
RD37



LC680
RD146
RD40



LC681
RD146
RD41



LC682
RD146
RD42



LC683
RD146
RD43



LC684
RD146
RD48



LC685
RD146
RD49



LC686
RD146
RD54



LC687
RD146
RD58



LC688
RD146
RD59



LC689
RD146
RD78



LC690
RD146
RD79



LC691
RD146
RD81



LC692
RD146
RD87



LC693
RD146
RD88



LC694
RD146
RD89



LC695
RD146
RD93



LC696
RD146
RD117



LC697
RD146
RD118



LC698
RD146
RD119



LC699
RD146
RD120



LC700
RD146
RD133



LC701
RD146
RD134



LC702
RD146
RD135



LC703
RD146
RD136



LC704
RD146
RD146



LC705
RD146
RD147



LC706
RD146
RD149



LC707
RD146
RD151



LC708
RD146
RD154



LC709
RD146
RD155



LC710
RD146
RD161



LC711
RD146
RD175



LC712
RD133
RD3



LC713
RD133
RD5



LC714
RD133
RD3



LC715
RD133
RD18



LC716
RD133
RD20



LC717
RD133
RD22



LC718
RD133
RD37



LC719
RD133
RD40



LC720
RD133
RD41



LC721
RD133
RD42



LC722
RD133
RD43



LC723
RD133
RD48



LC724
RD133
RD49



LC725
RD133
RD54



LC726
RD133
RD58



LC727
RD133
RD59



LC728
RD133
RD78



LC729
RD133
RD79



LC730
RD133
RD81



LC731
RD133
RD87



LC732
RD133
RD88



LC733
RD133
RD89



LC734
RD133
RD93



LC735
RD133
RD117



LC736
RD133
RD118



LC737
RD133
RD119



LC738
RD133
RD120



LC739
RD133
RD133



LC740
RD133
RD134



LC741
RD133
RD135



LC742
RD133
RD136



LC743
RD133
RD146



LC744
RD133
RD147



LC745
RD133
RD149



LC746
RD133
RD151



LC747
RD133
RD154



LC748
RD133
RD155



LC749
RD133
RD161



LC750
RD133
RD175



LC751
RD175
RD3



LC752
RD175
RD5



LC753
RD175
RD18



LC754
RD175
RD20



LC755
RD175
RD22



LC756
RD175
RD37



LC757
RD175
RD40



LC758
RD175
RD41



LC759
RD175
RD42



LC760
RD175
RD43



LC761
RD175
RD48



LC762
RD175
RD49



LC763
RD175
RD54



LC764
RD175
RD58



LC765
RD175
RD59



LC766
RD175
RD78



LC767
RD175
RD79



LC768
RD175
RD81



LC769
RD193
RD193



LC770
RD194
RD194



LC771
RD195
RD195



LC772
RD196
RD196



LC773
RD197
RD197



LC774
RD198
RD198



LC775
RD199
RD199



LC776
RD200
RD200



LC777
RD201
RD201



LC778
RD202
RD202



LC779
RD203
RD203



LC780
RD204
RD204



LC781
RD205
RD205



LC782
RD206
RD206



LC783
RD207
RD207



LC784
RD208
RD208



LC785
RD209
RD209



LC786
RD210
RD210



LC787
RD211
RD211



LC788
RD212
RD212



LC789
RD213
RD213



LC790
RD214
RD214



LC791
RD215
RD215



LC792
RD216
RD216



LC793
RD217
RD217



LC794
RD218
RD218



LC795
RD219
RD219



LC796
RD220
RD220



LC797
RD221
RD221



LC798
RD222
RD222



LC799
RD223
RD223



LC800
RD224
RD224



LC801
RD225
RD225



LC802
RD226
RD226



LC803
RD227
RD227



LC804
RD228
RD228



LC805
RD229
RD229



LC806
RD230
RD230



LC807
RD231
RD231



LC808
RD232
RD232



LC809
RD233
RD233



LC810
RD234
RD234



LC811
RD235
RD235



LC812
RD236
RD236



LC813
RD237
RD237



LC814
RD238
RD238



LC815
RD239
RD239



LC816
RD240
RD240



LC817
RD241
RD241



LC818
RD242
RD242



LC819
RD243
RD243



LC820
RD244
RD244



LC821
RD245
RD245



LC822
RD246
RD246



LC823
RD17
RD193



LC824
RD17
RD194



LC825
RD17
RD195



LC826
RD17
RD196



LC827
RD17
RD197



LC828
RD17
RD198



LC829
RD17
RD199



LC830
RD17
RD200



LC831
RD17
RD201



LC832
RD17
RD202



LC833
RD17
RD203



LC834
RD17
RD204



LC835
RD17
RD205



LC836
RD17
RD206



LC837
RD17
RD207



LC838
RD17
RD208



LC839
RD17
RD209



LC840
RD17
RD210



LC841
RD17
RD211



LC842
RD17
RD212



LC843
RD17
RD213



LC844
RD17
RD214



LC845
RD17
RD215



LC846
RD17
RD216



LC847
RD17
RD217



LC848
RD17
RD218



LC849
RD17
RD219



LC850
RD17
RD220



LC851
RD17
RD221



LC852
RD17
RD222



LC853
RD17
RD223



LC854
RD17
RD224



LC855
RD17
RD225



LC856
RD17
RD226



LC857
RD17
RD227



LC858
RD17
RD228



LC859
RD17
RD229



LC860
RD17
RD230



LC861
RD17
RD231



LC862
RD17
RD232



LC863
RD17
RD233



LC864
RD17
RD234



LC865
RD17
RD235



LC866
RD17
RD236



LC867
RD17
RD237



LC868
RD17
RD238



LC869
RD17
RD239



LC870
RD17
RD240



LC871
RD17
RD241



LC872
RD17
RD242



LC873
RD17
RD243



LC874
RD17
RD244



LC875
RD17
RD245



LC876
RD17
RD246



LC877
RD1
RD193



LC878
RD1
RD194



LC879
RD1
RD195



LC880
RD1
RD196



LC881
RD1
RD197



LC882
RD1
RD198



LC883
RD1
RD199



LC884
RD1
RD200



LC885
RD1
RD201



LC886
RD1
RD202



LC887
RD1
RD203



LC888
RD1
RD204



LC889
RD1
RD205



LC890
RD1
RD206



LC891
RD1
RD207



LC892
RD1
RD208



LC893
RD1
RD209



LC894
RD1
RD210



LC895
RD1
RD211



LC896
RD1
RD212



LC897
RD1
RD213



LC898
RD1
RD214



LC899
RD1
RD215



LC900
RD1
RD216



LC901
RD1
RD217



LC902
RD1
RD218



LC903
RD1
RD219



LC904
RD1
RD220



LC905
RD1
RD221



LC906
RD1
RD222



LC907
RD1
RD223



LC908
RD1
RD224



LC909
RD1
RD225



LC910
RD1
RD226



LC911
RD1
RD227



LC912
RD1
RD228



LC913
RD1
RD229



LC914
RD1
RD230



LC915
RD1
RD231



LC916
RD1
RD232



LC917
RD1
RD233



LC918
RD1
RD234



LC919
RD1
RD235



LC920
RD1
RD236



LC921
RD1
RD237



LC922
RD1
RD238



LC923
RD1
RD239



LC924
RD1
RD240



LC925
RD1
RD241



LC926
RD1
RD242



LC927
RD1
RD243



LC928
RD1
RD244



LC929
RD1
RD245



LC930
RD1
RD246



LC931
RD50
RD193



LC932
RD50
RD194



LC933
RD50
RD195



LC934
RD50
RD196



LC935
RD50
RD197



LC936
RD50
RD198



LC937
RD50
RD199



LC938
RD50
RD200



LC939
RD50
RD201



LC940
RD50
RD202



LC941
RD50
RD203



LC942
RD50
RD204



LC943
RD50
RD205



LC944
RD50
RD206



LC945
RD50
RD207



LC946
RD50
RD208



LC947
RD50
RD209



LC948
RD50
RD210



LC949
RD50
RD211



LC950
RD50
RD212



LC951
RD50
RD213



LC952
RD50
RD214



LC953
RD50
RD215



LC954
RD50
RD216



LC955
RD50
RD217



LC956
RD50
RD218



LC957
RD50
RD219



LC958
RD50
RD220



LC959
RD50
RD221



LC960
RD50
RD222



LC961
RD50
RD223



LC962
RD50
RD224



LC963
RD50
RD225



LC964
RD50
RD226



LC965
RD50
RD227



LC966
RD50
RD228



LC967
RD50
RD229



LC968
RD50
RD230



LC969
RD50
RD231



LC970
RD50
RD232



LC971
RD50
RD233



LC972
RD50
RD234



LC973
RD50
RD235



LC974
RD50
RD236



LC975
RD50
RD237



LC976
RD50
RD238



LC977
RD50
RD239



LC978
RD50
RD240



LC979
RD50
RD241



LC980
RD50
RD242



LC981
RD50
RD243



LC982
RD50
RD244



LC983
RD50
RD245



LC984
RD50
RD246



LC985
RD4
RD193



LC986
RD4
RD194



LC987
RD4
RD195



LC988
RD4
RD196



LC989
RD4
RD197



LC990
RD4
RD198



LC991
RD4
RD199



LC992
RD4
RD200



LC993
RD4
RD201



LC994
RD4
RD202



LC995
RD4
RD203



LC996
RD4
RD204



LC997
RD4
RD205



LC998
RD4
RD206



LC999
RD4
RD207



LC1000
RD4
RD208



LC1001
RD4
RD209



LC1002
RD4
RD210



LC1003
RD4
RD211



LC1004
RD4
RD212



LC1005
RD4
RD213



LC1006
RD4
RD214



LC1007
RD4
RD215



LC1008
RD4
RD216



LC1009
RD4
RD217



LC1010
RD4
RD218



LC1011
RD4
RD219



LC1012
RD4
RD220



LC1013
RD4
RD221



LC1014
RD4
RD222



LC1015
RD4
RD223



LC1016
RD4
RD224



LC1017
RD4
RD225



LC1018
RD4
RD226



LC1019
RD4
RD227



LC1020
RD4
RD228



LC1021
RD4
RD229



LC1022
RD4
RD230



LC1023
RD4
RD231



LC1024
RD4
RD232



LC1025
RD4
RD233



LC1026
RD4
RD234



LC1027
RD4
RD235



LC1028
RD4
RD236



LC1029
RD4
RD237



LC1030
RD4
RD238



LC1031
RD4
RD239



LC1032
RD4
RD240



LC1033
RD4
RD241



LC1034
RD4
RD242



LC1035
RD4
RD243



LC1036
RD4
RD244



LC1037
RD4
RD245



LC1038
RD4
RD246



LC1039
RD145
RD193



LC1040
RD145
RD194



LC1041
RD145
RD195



LC1042
RD145
RD196



LC1043
RD145
RD197



LC1044
RD145
RD198



LC1045
RD145
RD199



LC1046
RD145
RD200



LC1047
RD145
RD201



LC1048
RD145
RD202



LC1049
RD145
RD203



LC1050
RD145
RD204



LC1051
RD145
RD205



LC1052
RD145
RD206



LC1053
RD145
RD207



LC1054
RD145
RD208



LC1055
RD145
RD209



LC1056
RD145
RD210



LC1057
RD145
RD211



LC1058
RD145
RD212



LC1059
RD145
RD213



LC1060
RD145
RD214



LC1061
RD145
RD215



LC1062
RD145
RD216



LC1063
RD145
RD217



LC1064
RD145
RD218



LC1065
RD145
RD219



LC1066
RD145
RD220



LC1067
RD145
RD221



LC1068
RD145
RD222



LC1069
RD145
RD223



LC1070
RD145
RD224



LC1071
RD145
RD225



LC1072
RD145
RD226



LC1073
RD145
RD227



LC1074
RD145
RD228



LC1075
RD145
RD229



LC1076
RD145
RD230



LC1077
RD145
RD231



LC1078
RD145
RD232



LC1079
RD145
RD233



LC1080
RD145
RD234



LC1081
RD145
RD235



LC1082
RD145
RD236



LC1083
RD145
RD237



LC1084
RD145
RD238



LC1085
RD145
RD239



LC1086
RD145
RD240



LC1087
RD145
RD241



LC1088
RD145
RD242



LC1089
RD145
RD243



LC1090
RD145
RD244



LC1091
RD145
RD245



LC1092
RD145
RD246



LC1093
RD9
RD193



LC1094
RD9
RD194



LC1095
RD9
RD195



LC1096
RD9
RD196



LC1097
RD9
RD197



LC1098
RD9
RD198



LC1099
RD9
RD199



LC1100
RD9
RD200



LC1101
RD9
RD201



LC1102
RD9
RD202



LC1103
RD9
RD203



LC1104
RD9
RD204



LC1105
RD9
RD205



LC1106
RD9
RD206



LC1107
RD9
RD207



LC1108
RD9
RD208



LC1109
RD9
RD209



LC1110
RD9
RD210



LC1111
RD9
RD211



LC1112
RD9
RD212



LC1113
RD9
RD213



LC1114
RD9
RD214



LC1115
RD9
RD215



LC1116
RD9
RD216



LC1117
RD9
RD217



LC1118
RD9
RD218



LC1119
RD9
RD219



LC1120
RD9
RD220



LC1121
RD9
RD221



LC1122
RD9
RD222



LC1123
RD9
RD223



LC1124
RD9
RD224



LC1125
RD9
RD225



LC1126
RD9
RD226



LC1127
RD9
RD227



LC1128
RD9
RD228



LC1129
RD9
RD229



LC1130
RD9
RD230



LC1131
RD9
RD231



LC1132
RD9
RD232



LC1133
RD9
RD233



LC1134
RD9
RD234



LC1135
RD9
RD235



LC1136
RD9
RD236



LC1137
RD9
RD237



LC1138
RD9
RD238



LC1139
RD9
RD239



LC1140
RD9
RD240



LC1141
RD9
RD241



LC1142
RD9
RD242



LC1143
RD9
RD243



LC1144
RD9
RD244



LC1145
RD9
RD245



LC1146
RD9
RD246



LC1147
RD168
RD193



LC1148
RD168
RD194



LC1149
RD168
RD195



LC1150
RD168
RD196



LC1151
RD168
RD197



LC1152
RD168
RD198



LC1153
RD168
RD199



LC1154
RD168
RD200



LC1155
RD168
RD201



LC1156
RD168
RD202



LC1157
RD168
RD203



LC1158
RD168
RD204



LC1159
RD168
RD205



LC1160
RD168
RD206



LC1161
RD168
RD207



LC1162
RD168
RD208



LC1163
RD168
RD209



LC1164
RD168
RD210



LC1165
RD168
RD211



LC1166
RD168
RD212



LC1167
RD168
RD213



LC1168
RD168
RD214



LC1169
RD168
RD215



LC1170
RD168
RD216



LC1171
RD168
RD217



LC1172
RD168
RD218



LC1173
RD168
RD219



LC1174
RD168
RD220



LC1175
RD168
RD221



LC1176
RD168
RD222



LC1177
RD168
RD223



LC1178
RD168
RD224



LC1179
RD168
RD225



LC1180
RD168
RD226



LC1181
RD168
RD227



LC1182
RD168
RD228



LC1183
RD168
RD229



LC1184
RD168
RD230



LC1185
RD168
RD231



LC1186
RD168
RD232



LC1187
RD168
RD233



LC1188
RD168
RD234



LC1189
RD168
RD235



LC1190
RD168
RD236



LC1191
RD168
RD237



LC1192
RD168
RD238



LC1193
RD168
RD239



LC1194
RD168
RD240



LC1195
RD168
RD241



LC1196
RD168
RD242



LC1197
RD168
RD243



LC1198
RD168
RD244



LC1199
RD168
RD245



LC1200
RD168
RD246



LC1201
RD10
RD193



LC1202
RD10
RD194



LC1203
RD10
RD195



LC1204
RD10
RD196



LC1205
RD10
RD197



LC1206
RD10
RD198



LC1207
RD10
RD199



LC1208
RD10
RD200



LC1209
RD10
RD201



LC1210
RD10
RD202



LC1211
RD10
RD203



LC1212
RD10
RD204



LC1213
RD10
RD205



LC1214
RD10
RD206



LC1215
RD10
RD207



LC1216
RD10
RD208



LC1217
RD10
RD209



LC1218
RD10
RD210



LC1219
RD10
RD211



LC1220
RD10
RD212



LC1221
RD10
RD213



LC1222
RD10
RD214



LC1223
RD10
RD215



LC1224
RD10
RD216



LC1225
RD10
RD217



LC1226
RD10
RD218



LC1227
RD10
RD219



LC1228
RD10
RD220



LC1229
RD10
RD221



LC1230
RD10
RD222



LC1231
RD10
RD223



LC1232
RD10
RD224



LC1233
RD10
RD225



LC1234
RD10
RD226



LC1235
RD10
RD227



LC1236
RD10
RD228



LC1237
RD10
RD229



LC1238
RD10
RD230



LC1239
RD10
RD231



LC1240
RD10
RD232



LC1241
RD10
RD233



LC1242
RD10
RD234



LC1243
RD10
RD235



LC1244
RD10
RD236



LC1245
RD10
RD237



LC1246
RD10
RD238



LC1247
RD10
RD239



LC1248
RD10
RD240



LC1249
RD10
RD241



LC1250
RD10
RD242



LC1251
RD10
RD243



LC1252
RD10
RD244



LC1253
RD10
RD245



LC1254
RD10
RD246



LC1255
RD55
RD193



LC1256
RD55
RD194



LC1257
RD55
RD195



LC1258
RD55
RD196



LC1259
RD55
RD197



LC1260
RD55
RD198



LC1261
RD55
RD199



LC1262
RD55
RD200



LC1263
RD55
RD201



LC1264
RD55
RD202



LC1265
RD55
RD203



LC1266
RD55
RD204



LC1267
RD55
RD205



LC1268
RD55
RD206



LC1269
RD55
RD207



LC1270
RD55
RD208



LC1271
RD55
RD209



LC1272
RD55
RD210



LC1273
RD55
RD211



LC1274
RD55
RD212



LC1275
RD55
RD213



LC1276
RD55
RD214



LC1277
RD55
RD215



LC1278
RD55
RD216



LC1279
RD55
RD217



LC1280
RD55
RD218



LC1281
RD55
RD219



LC1282
RD55
RD220



LC1283
RD55
RD221



LC1284
RD55
RD222



LC1285
RD55
RD223



LC1286
RD55
RD224



LC1287
RD55
RD225



LC1288
RD55
RD226



LC1289
RD55
RD227



LC1290
RD55
RD228



LC1291
RD55
RD229



LC1292
RD55
RD230



LC1293
RD55
RD231



LC1294
RD55
RD232



LC1295
RD55
RD233



LC1296
RD55
RD234



LC1297
RD55
RD235



LC1298
RD55
RD236



LC1299
RD55
RD237



LC1300
RD55
RD238



LC1301
RD55
RD239



LC1302
RD55
RD240



LC1303
RD55
RD241



LC1304
RD55
RD242



LC1305
RD55
RD243



LC1306
RD55
RD244



LC1307
RD55
RD245



LC1308
RD55
RD246



LC1309
RD37
RD193



LC1310
RD37
RD194



LC1311
RD37
RD195



LC1312
RD37
RD196



LC1313
RD37
RD197



LC1314
RD37
RD198



LC1315
RD37
RD199



LC1316
RD37
RD200



LC1317
RD37
RD201



LC1318
RD37
RD202



LC1319
RD37
RD203



LC1320
RD37
RD204



LC1321
RD37
RD205



LC1322
RD37
RD206



LC1323
RD37
RD207



LC1324
RD37
RD208



LC1325
RD37
RD209



LC1326
RD37
RD210



LC1327
RD37
RD211



LC1328
RD37
RD212



LC1329
RD37
RD213



LC1330
RD37
RD214



LC1331
RD37
RD215



LC1332
RD37
RD216



LC1333
RD37
RD217



LC1334
RD37
RD218



LC1335
RD37
RD219



LC1336
RD37
RD220



LC1337
RD37
RD221



LC1338
RD37
RD222



LC1339
RD37
RD223



LC1340
RD37
RD224



LC1341
RD37
RD225



LC1342
RD37
RD226



LC1343
RD37
RD227



LC1344
RD37
RD228



LC1345
RD37
RD229



LC1346
RD37
RD230



LC1347
RD37
RD231



LC1348
RD37
RD232



LC1349
RD37
RD233



LC1350
RD37
RD234



LC1351
RD37
RD235



LC1352
RD37
RD236



LC1353
RD37
RD237



LC1354
RD37
RD238



LC1355
RD37
RD239



LC1356
RD37
RD240



LC1357
RD37
RD241



LC1358
RD37
RD242



LC1359
RD37
RD243



LC1360
RD37
RD244



LC1361
RD37
RD245



LC1362
RD37
RD246



LC1363
RD143
RD193



LC1364
RD143
RD194



LC1365
RD143
RD195



LC1366
RD143
RD196



LC1367
RD143
RD197



LC1368
RD143
RD198



LC1369
RD143
RD199



LC1370
RD143
RD200



LC1371
RD143
RD201



LC1372
RD143
RD202



LC1373
RD143
RD203



LC1374
RD143
RD204



LC1375
RD143
RD205



LC1376
RD143
RD206



LC1377
RD143
RD207



LC1378
RD143
RD208



LC1379
RD143
RD209



LC1380
RD143
RD210



LC1381
RD143
RD211



LC1382
RD143
RD212



LC1383
RD143
RD213



LC1384
RD143
RD214



LC1385
RD143
RD215



LC1386
RD143
RD216



LC1387
RD143
RD217



LC1388
RD143
RD218



LC1389
RD143
RD219



LC1390
RD143
RD220



LC1391
RD143
RD221



LC1392
RD143
RD222



LC1393
RD143
RD223



LC1394
RD143
RD224



LC1395
RD143
RD225



LC1396
RD143
RD226



LC1397
RD143
RD227



LC1398
RD143
RD228



LC1399
RD143
RD229



LC1400
RD143
RD230



LC1401
RD143
RD231



LC1402
RD143
RD232



LC1403
RD143
RD233



LC1404
RD143
RD234



LC1405
RD143
RD235



LC1406
RD143
RD236



LC1407
RD143
RD237



LC1408
RD143
RD238



LC1409
RD143
RD239



LC1410
RD143
RD240



LC1411
RD143
RD241



LC1412
RD143
RD242



LC1413
RD143
RD243



LC1414
RD143
RD244



LC1415
RD143
RD245



LC1416
RD143
RD246










wherein RD1 to RD246 have the structures defined in the following LIST 11:




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It should be understood that in the formula Ir(LAi-m)(LAs-n)(LAt-o), n and o each have the same meaning/definition as m, and s and t each have the same meaning/definition as i. The variables n, o, s, and t are only used to clearly demonstrate that each individual LA ligand is independently selected.


In some embodiments, the compound is selected from the group consisting of only those compounds whose LBk corresponds to one of the following: LB1, LB2, LB18, LB28, LB38, LB108, LB118, LB122, LB124, LB126, LB128, LB130, LB132, LB134, LB136, LB138, LB140, LB142, LB144, LB156, LB158, LB160, LB162, LB164, LB168, LB172, LB175, LB204, LB206, LB214, LB216, LB218, LB220, LB222, LB231, LB233, LB235, LB237, LB240, LB242, LB244, LB246, LB248, LB250, LB252, LB254, LB256, LB258, LB260, LB262 and LB264, LB265, LB266, LB267, LB268, LB269, and LB270.


In some embodiments, the compound is selected from the group consisting of only those compounds whose LBk corresponds to one of the following: LB1, LB2, LB18, LB28, LB38, LB108, LB118, LB122, LB126, LB128, LB132, LB136, LB138, LB142, LB156, LB162, LB204, LB206, LB214, LB216, LB218, LB220, LB231, LB233, LB237, LB264, LB265, LB266, LB267, LB268, LB269, and LB270.


In some embodiments, the compound is selected from the group consisting of only those compounds having LCj-I or LCj-II ligand whose corresponding R201 and R202 are defined to be one of the following structures: RD1, RD3, RD4, RD5, RD9, RD10, RD17, RD18, RD20, RD22, RD37, RD40, RD41, RD42, RD43, RD48, RD49, RD50, RD54, RD55, RD58, RD59, RD78, RD79, RD81, RD87, RD88, RD89, RD93, RD116, RD17, RD118, RD119, RD120, RD133, RD134, RD135, RD136, RD143, RD144, RD145, RD146, RD147, RD149, RD15, RD154, RD15, RD161, RD175 RD190, RD193, RD200, RD201, RD206, RD210, RD214, RD215, RD216, RD218, RD219, RD220, RD227, RD237, RD241, RD242, RD245, and RD246.


In some embodiments, the compound is selected from the group consisting of only those compounds having LCj-I or LCj-II ligand whose corresponding R201 and R202 are defined to be one of the following structures: RD1, RD3, RD4, RD5, RD9, RD10, RD17, RD22, RD43, RD50, RD78, RD116, RD118, RD133, RD134, RD135, RD136, RD143, RD144, RD145, RD146, RD149, RD15, RD154, RD155 RD190, RD193, RD200, RD201, RD206, RD210, RD214, RD215, RD216, RD218, RD219, RD220, RD227, RD237, RD241, RD242, RD245, and RD246.


In some embodiments, the compound is selected from the group consisting of only those compounds having one of the following structures for the LCj-I ligand:




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In some embodiments, at the compound is selected from the group consisting of the structures of the following LIST 12:




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In some embodiments, the compound having a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein can be at least 5% deuterated, at least 10% deuterated, at least 20% deuterated, at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, percent deuteration has its ordinary meaning and includes the percent of possible hydrogen atoms (e.g., positions that are hydrogen or deuterium) that are replaced by deuterium atoms.).


C. The OLEDs and the Devices of the Present Disclosure

In another aspect, the present disclosure also provides an OLED device comprising a first organic layer that contains a compound as disclosed in the above compounds section of the present disclosure.


In some embodiments, the first organic layer can comprise a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.


In some embodiments, the organic layer may be an emissive layer and the compound as described herein may be an emissive dopant or a non-emissive dopant.


In some embodiments, the organic layer may further comprise a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan, wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CCnH2n+1, Ar1, Ar1-Ar2, CnH2n-Ar1, or no substitution, wherein n is an integer from 1 to 10; and wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.


In some embodiments, the organic layer may further comprise a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, boryl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).


In some embodiments, the host may be selected from the HOST Group consisting of:




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and combinations thereof.


In some embodiments, the organic layer may further comprise a host, wherein the host comprises a metal complex.


In some embodiments, the compound as described herein may be a sensitizer; wherein the device may further comprise an acceptor; and wherein the acceptor may be selected from the group consisting of fluorescent emitter, delayed fluorescence emitter, and combination thereof.


In yet another aspect, the OLED of the present disclosure may also comprise an emissive region containing a compound as disclosed in the above compounds section of the present disclosure.


In some embodiments, the emissive region can comprise a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.


In some embodiments, at least one of the anode, the cathode, or a new layer disposed over the organic emissive layer functions as an enhancement layer. The enhancement layer comprises a plasmonic material exhibiting surface plasmon resonance that non-radiatively couples to the emitter material and transfers excited state energy from the emitter material to non-radiative mode of surface plasmon polariton. The enhancement layer is provided no more than a threshold distance away from the organic emissive layer, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer and the threshold distance is where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed over the enhancement layer on the opposite side of the organic emissive layer. In some embodiments, the outcoupling layer is disposed on opposite side of the emissive layer from the enhancement layer but still outcouples energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters the energy from the surface plasmon polaritons. In some embodiments this energy is scattered as photons to free space. In other embodiments, the energy is scattered from the surface plasmon mode into other modes of the device such as but not limited to the organic waveguide mode, the substrate mode, or another waveguiding mode. If energy is scattered to the non-free space mode of the OLED other outcoupling schemes could be incorporated to extract that energy to free space. In some embodiments, one or more intervening layer can be disposed between the enhancement layer and the outcoupling layer. The examples for interventing layer(s) can be dielectric materials, including organic, inorganic, perovskites, oxides, and may include stacks and/or mixtures of these materials.


The enhancement layer modifies the effective properties of the medium in which the emitter material resides resulting in any or all of the following: a decreased rate of emission, a modification of emission line-shape, a change in emission intensity with angle, a change in the stability of the emitter material, a change in the efficiency of the OLED, and reduced efficiency roll-off of the OLED device. Placement of the enhancement layer on the cathode side, anode side, or on both sides results in OLED devices which take advantage of any of the above-mentioned effects. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, the OLEDs according to the present disclosure may include any of the other functional layers often found in OLEDs.


The enhancement layer can be comprised of plasmonic materials, optically active metamaterials, or hyperbolic metamaterials. As used herein, a plasmonic material is a material in which the real part of the dielectric constant 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 may 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 where the medium as a whole acts differently than the sum of its material parts. In particular, we define optically active metamaterials as materials which have both negative permittivity and negative permeability. Hyperbolic metamaterials, on the other hand, are anisotropic media in which the permittivity or permeability are of different sign for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are strictly distinguished from many other photonic structures such as Distributed Bragg Reflectors (“DBRs”) in that the medium should appear uniform in the direction of propagation on the length scale of the wavelength of light. Using terminology that one skilled in the art can understand: the dielectric constant of the metamaterials in the direction of propagation can be described with the effective medium approximation. Plasmonic materials and metamaterials provide methods for controlling the propagation of light that can enhance OLED performance in a number of ways.


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


In some embodiments, the outcoupling layer has wavelength-sized features that are arranged periodically, quasi-periodically, or randomly, or sub-wavelength-sized features that are arranged periodically, quasi-periodically, or randomly. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles and in other embodiments the outcoupling layer is composed of a plurality of nanoparticles disposed over a material. In these embodiments the outcoupling may be tunable by at least one of varying a size of the plurality of nanoparticles, varying a shape of the plurality of nanoparticles, changing a material of the plurality of nanoparticles, adjusting a thickness of the material, changing the refractive index of the material or an additional layer disposed on the plurality of nanoparticles, varying a thickness of the enhancement layer, and/or varying the material of the enhancement layer. The plurality of nanoparticles of the device may be formed from at least one of metal, dielectric material, semiconductor materials, an alloy of metal, a mixture of dielectric materials, a stack or layering of one or more materials, and/or a core of one type of material and that is coated with a shell of a different type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles wherein the metal is 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 plurality of nanoparticles may have additional layer disposed over them. In some embodiments, the polarization of the emission can be tuned using the outcoupling layer. Varying the dimensionality and periodicity of the outcoupling layer can select a type of polarization that is preferentially outcoupled to air. In some embodiments the outcoupling layer also acts as an electrode of the device.


In yet another aspect, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound as disclosed in the above compounds section of the present disclosure.


In some embodiments, the consumer product comprises an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound having a structure of Ir(LA)p(LB)q(LC)r as described herein.


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 interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.


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 each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.


Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.


The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.


More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 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”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.



FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn 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 more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.


More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport 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. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport 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. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. 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 may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.



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 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may 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 one example of how some layers may be omitted from the structure of device 100.


The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the present disclosure may be used in connection 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. Functional OLEDs may be achieved by combining the various layers described in different 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. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may 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. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.


Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs 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. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.


Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP, also referred to as organic vapor jet deposition (OVJD)), such as 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 carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and organic vapor jet printing (OVJP). Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons are a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.


Devices fabricated in accordance with embodiments of the present disclosure may further optionally comprise 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, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise 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 as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.


Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. A consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-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, micro-displays (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, a light therapy device, and a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present disclosure, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25° C.), but could be used outside this temperature range, for example, from −40 degree C. to +80° C.


More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.


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 employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.


In some embodiments, the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.


In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises a RGB pixel arrangement or white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a hand held device, or a wearable device. In some embodiments, the OLED is a display panel having less than 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a display panel having at least 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a lighting panel.


In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. application Ser. No. 15/700,352, which is hereby incorporated by reference in its entirety), triplet-triplet annihilation, or combinations of these processes. In some embodiments, the emissive dopant can be a racemic mixture, or can be 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 others). When there are more than one ligand coordinated to a metal, the ligands can all be the same in some embodiments. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, every ligand can be different from each other. This is also true in embodiments where a ligand being coordinated to a metal can be linked with other ligands being coordinated to that metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, where the coordinating ligands are being linked together, all of the ligands can be the same in some embodiments, and at least one of the ligands being linked can be different from the other ligand(s) in some other embodiments.


In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED where one or multiple layers in the OLED contains an acceptor in the form of one or more fluorescent and/or delayed fluorescence emitters. In some embodiments, the compound can be used as one component of an exciplex to be used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor and the acceptor will emit the energy or further transfer energy to a final emitter. The acceptor concentrations can range from 0.001% to 100%. The acceptor could be in either 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 arise from any or all of the sensitizer, acceptor, and final emitter


According to another aspect, a formulation comprising the compound described herein is also disclosed.


The OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.


In yet another aspect of the present disclosure, a formulation that comprises the novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, electron blocking material, hole blocking material, and an electron transport material, disclosed herein.


The present disclosure encompasses any chemical structure comprising the novel compound of the present disclosure, or a monovalent or polyvalent variant thereof. In other words, the inventive compound, or a monovalent or polyvalent variant thereof, can be a part of a larger chemical structure. Such chemical structure can be selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule (also known as supermolecule). 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 rest 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 or bonds to the rest of the chemical structure. In the instance of a supramolecule, the inventive compound can also be incorporated into the supramolecule complex without covalent bonds.


D. Combination of the Compounds of the Present Disclosure with Other Materials

The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may 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 referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.


a) Conductivity Dopants:

A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.


Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.




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b) HIL/HTL:

A hole injecting/transporting material to be used in the present disclosure is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoOx; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.


Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:




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Each of Ar1 to Ar9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as 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, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by 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 acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.


In one aspect, Ar1 to Ar9 is independently selected from the group consisting of:




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wherein k is an integer from 1 to 20; X101 to X108 is C (including CH) or N; Z101 is NAr1, O, or S; Ar1 has the same group defined above.


Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:




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wherein Met is a metal, which can have an atomic weight greater than 40; (Y101-Y102) is a bidentate ligand, Y101 and Y102 are independently selected from C, N, O, P, and S; L101 is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.


In one aspect, (Y101-Y102) is a 2-phenylpyridine derivative. In another aspect, (Y101-Y102) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc+/Fc couple less than about 0.6 V.


Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those 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, U.S. Ser. No. 06/517,957, 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, U.S. Pat. Nos. 5,061,569, 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.




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c) EBL:

An electron blocking layer (EBL) may 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 may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may 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 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 higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.


d) Hosts:

The light emitting layer of the organic EL device of the present disclosure preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.


Examples of metal complexes used as host are preferred to have the following general formula:




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wherein Met is a metal; (Y103-Y104) is a bidentate ligand, Y103 and Y104 are independently selected from C, N, O, P, and S; L101 is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.


In one aspect, the metal complexes are:




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wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.


In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y103-Y104) is a carbene ligand.


In one aspect, the host compound contains at least one of the following groups 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; the group consisting of aromatic heterocyclic compounds such as 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, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by 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 acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.


In one aspect, the host compound contains at least one of the following groups in the molecule:




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wherein R101 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 acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20. X101 to X108 are independently selected from C (including CH) or N. Z101 and Z102 are independently selected from NR101, O, or S.


Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, U.S. Pat. No. 9,466,803,




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e) Additional Emitters:

One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.


Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No. 06/916,554, 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, US2014103305, U.S. Pat. Nos. 6,303,238, 6,413,656, 6,653,654, 6,670,645, 6,687,266, 6,835,469, 6,921,915, 7,279,704, 7,332,232, 7,378,162, 7,534,505, 7,675,228, 7,728,137, 7,740,957, 7,759,489, 7,951,947, 8,067,099, 8,592,586, 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.




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f) HBL:

A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may 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 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 higher triplet energy than one or more of the hosts closest to the HBL interface.


In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.


In another aspect, compound used in HBL contains at least one of the following groups in the molecule:




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wherein k is an integer from 1 to 20; L101 is another ligand, k′ is an integer from 1 to 3.


g) ETL:

Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.


In one aspect, compound used in ETL contains at least one of the following groups in the molecule:




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wherein R101 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 acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar1 to Ar3 has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X101 to X108 is selected from C (including CH) or N.


In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:




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wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.


Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S. Pat. Nos. 6,656,612, 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,




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h) Charge Generation Layer (CGL)

In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.


In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. The minimum amount of hydrogen of the compound being deuterated is selected from the group consisting of 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.


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 may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.


Experimental Data



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Synthesis of bis[1-(4-(tert-butyl)naphthalen-2-yl)-7-(2,2-dimethylpropyl-1,1-d2)-8-(methyl-d3)benzo[4,5]thieno[2,3-c]pyridinyl]-(3,7-diethyl-4,6-nonanedionato-k2O,O′)-iridium(II)

A solution of 1-(4-(tert-butyl)naphthalen-2-yl)-7-(2,2-dimethylpropyl-1,1-d2)-8-(methyl-d3)benzo[4,5]thieno[2,3-c]pyridine (1.97 g, 4.32 mmol) and iridium(III) chloride hydrate (0.80 g, 2.16 mmol) in 2-ethoxyethanol (21 mL) and heavy water (7 mL) was degassed with N2 for 10 minutes. The mixture was heated at 95° C. for 20 hours. After cooling the reaction to room temperature, MeOH was added and the red solid was filtered and washed with MeOH (3×20 ml). The resulting red solid (2.35 g, 1.032 mmol) was added to a solution of 3,7-diethylnonane-4,6-dione (0.548 g, 2.58 mmol), powdered potassium carbonate (0.428 g, 3.09 mmol) in DCM (15 ml) and MeOH (15 ml). The reaction mixture was degassed under N2 for 5 minutes, then stirred at 40° C. for 24 hours in a flask covered with foil to exclude light. After cooling the reaction to room temperature, MeOH (100 mL) was added and the red solid was filtered and washed with MeOH (2×10 ml) to give 1.65 g of crude material. The crude product was purified on a silica gel column chromatography, eluting with a gradient of 30% dichloromethane in heptanes. Fractions containing product were concentrated under reduced pressure. The product was dried under vacuum at 50° C. for 6 hours to give bis[1-(4-(tert-butyl)naphthalen-2-yl)-7-(2,2-dimethylpropyl-1,1-d2)-8-(methyl-d3)benzo[4,5]thieno[2,3-c]pyridinyl]-(3,7-diethyl-4,6-nonanedionato-k2O,O′)-iridium(III) (1.02 g, 37% yield) as a red solid.


Device Examples

All example devices were fabricated by high vacuum (<10−7 Torr) thermal evaporation. The anode electrode was 1,200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (8-hydroxyquinoline lithium) followed by 1,000 Å of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package. The organic stack of the device examples consisted of sequentially, from the ITO surface, 100 Å of LG101 (purchased from LG Chem) as the hole injection layer (HIL); 400 Å of HTM as a hole transporting layer (HTL); 50 Å of EBM as an electron blocking layer (EBL); 400 Å of an emissive layer (EML) containing RH as red host and 3% of emitter; and 350 Å of Liq (8-hydroxyquinoline lithium) doped with 35% of ETM as the electron transporting layer (ETL). Table 1 shows the thickness of the device layers and materials, and the chemical structures of the device materials are shown below.









TABLE 1







Device layer materials and thicknesses









Layer
Material
Thickness [Å]












Anode
ITO
1,200


HIL
LG-101
100


HTL
HTM
400


EBL
EBM
50


EML
RH: Emitter 3%
400


ETL
Liq: ETM 35%
350


EIL
Liq
10


Cathode
Al
1,000







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Upon fabrication, the devices were tested to measure EL and JVL. For this purpose, the samples were energized by the 2 channel Keysight B2902A SMU at a current density of 10 mA/cm2 and measured by the Photo Research PR735 Spectroradiometer. Radiance (W/str/cm2) from 380 nm to 1080 nm, and total integrated photon count were collected. The devices were then placed under a large area silicon photodiode for the JVL sweep. The integrated photon count of the device at 10 mA/cm2 was used to convert the photodiode current to photon count. The voltage was swept from 0 to a voltage equating to 200 mA/cm2. The device lifetime (LT95) was measured when the luminescence of the devices decaying to the 95% of the initial luminescence at 1K nits. All results are summarized in Table 2. LE (luminance efficiency), EQE (external quantum efficiency), PE (power efficiency), and LT95 of inventive example (Device 1) are reported as relative numbers normalized to the results of the comparative example (Device 2).


Tables 2 provides a summary of performance of electroluminescence device of the materials. The inventive device (Device 1) shows unexpected better performance in all parameters, i.e., higher LE, EQE, PE and longer LT95 than the comparative example (Device 2). All results show the improvement of device performance by using inventive example with partially deuterated alkyl groups on the aza-dibenzothiophene moiety. As a result, inventive examples have great potentials for applications in organic light emitting diodes (OLED).









TABLE 2







device results
















1931 CIE
λ max



















Device
Emitter
x
y
[nm]
LE
EQE
PE
LT95





Device 1
Inventive
0.675
0.325
618
1.01
1.01
1.02
1.04



Example









Device 2
Comparative
0.676
0.324
618
1.00
1.00
1.00
1.00



Example















Claims
  • 1. A compound having a structure of Ir(LA)p(LB)q(LC)r, wherein LB and LC are different bidentate ligands; wherein p is 1 or 2; q is 1 or 2; r is 0, 1, or 2; wherein ligand LA has a structure of the following Formula I:
  • 2. The compound of claim 1, wherein each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.
  • 3. The compound of claim 1, wherein at least one of X1 and X2 is N; or wherein X1 and X2 are C; and/or wherein each of X3 to X6 is C or wherein at least one of X3 to X6 is N.
  • 4. The compound of claim 1, wherein moiety B is monocyclic aromatic group.
  • 5. The compound of claim 1, wherein moiety B is polycyclic aromatic group.
  • 6. The compound of claim 1, wherein the at least one RB comprises aryl or heteroaryl; and/or wherein the at least one RB substituent comprises a partially deuterated alkyl or a partially deuterated cycloalkyl group.
  • 7. The compound of claim 1, wherein two adjacent RA are joined or fused to form a ring; and/or wherein two adjacent RC are joined or fused to form a ring; or wherein one RA and one RB are joined or fused to form a ring; or wherein one RB and one RC are joined or fused to form a ring.
  • 8. The compound of claim 1, wherein X5 and X6 are C and the RC located at X5 and X6 are joined or fused to form a 5- or 6-membered ring; or wherein RC located at one of X3 to X6 is alkyl or cycloalkyl; or wherein X4 is C and the RC located at X4 is alkyl or cycloalkyl.
  • 9. The compound claim 1, wherein at least one RA is a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof; and/or wherein at least one RB comprises a substituent other than partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl; and/or wherein at least one RC is a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.
  • 10. The compound of claim 1, wherein the ligand LA is selected from the group consisting of the structures of
  • 11. The compound of claim 1, wherein the ligand LA is selected from the group consisting of the structures of
  • 12. The compound of claim 1, wherein the ligand LA is selected from the group consisting of LA1-1 to LA1500-45, where for LAi-m, m is an integer from 1 to 45 and i is an integer from 1 to 1500; wherein LAi-1 to LAi-45 have the structures defined as follows:
  • 13. The compound of claim 1, wherein the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); and wherein LA, LB, and LC are different from each other.
  • 14. The compound of claim 13, wherein LB and LC are each independently selected from the group consisting of:
  • 15. The compound of claim 12, wherein LA can be selected from LAi-m, wherein i is an integer from 1 to 1500; m is an integer from 1 to 45; LB can be selected from LBk, wherein k is an integer from 1 to 324; and LC can be selected from LCj-I and LCj-II, wherein j is an integer from 1 to 1416 wherein: when the compound has formula Ir(LAi-m)(LAs-n)(LAt-o), wherein s and t are each independently an integer from 1 to 1500, and n and o are each independently an integer from 1 to 45; and the compound is selected from the group consisting of Ir(LA1-1)(LA2-1)2 to Ir(LA1500-45)(LA1499-45)2, Ir(LA1-1)2(LA2-1) to Ir(LA1500-45)2(LA1499-45), Ir(LA1-1)(LA2-1)(LA3-1) to Ir(LA1500-45) (LA1499-45) (LA1498-45), Ir(LA1-1)(LA1-2)2 to Ir(LA1500-45)(LA1500-44)2, Ir(LA1-1)2(LA1-2) to Ir(LA1500-45)2(LA1500-44), and Ir(LA1-1)(LA1-2)(LA1-3) to Ir(LA1500-43) (LA1500-44) (LA1500-45), with the proviso that at least two of i, s, and t are different in the same formula, or at least two of m, n, and o are different in the same formula;when the compound has formula Ir(LAi-m)(LBk)(LCj-I), the compound is selected from the group consisting of Ir(LA1-1)(LB1)(LC1-I) to Ir(LA1500-45)(LB324)(LC1416-I);when the compound has formula Ir(LAi-m)(LBk)(LCj-II), the compound is selected from the group consisting of Ir(LA1-1)(LB1)(LC1-I) to Ir(LA1500-45)(LB324)(LC1416-I);when the compound has formula Ir(LAi-m)2(LCj-I), the compound is selected from the group consisting of Ir(LA1-1)2(LC1-I) to Ir(LA1500-45)2(LC1416-I); andwhen the compound has formula Ir(LAi-m)2(LCj-II), the compound is selected from the group consisting of Ir(LA1-1)2(LC1-II) to Ir(LA1500-45)2(LC1416-II);wherein each LB1 to LB324 have the following structures:
  • 16. The compound of claim 1, wherein the compound is selected from the group consisting of:
  • 17. An organic light emitting device (OLED) comprising: an anode;a cathode; andan organic layer disposed between the anode and the cathode,
  • 18. The OLED of claim 17, wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).
  • 19. The OLED of claim 18, wherein the host is selected from the group consisting of the HOST Group defined herein.
  • 20. A consumer product comprising an organic light-emitting device comprising: an anode;a cathode; andan organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Ir(LA)p(LB)q(LC)r, wherein LB and LC are different bidentate ligands; wherein p is 1 or 2; q is 1 or 2; r is 0, 1, or 2;wherein ligand LA has a structure of the following Formula I:
CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. patent application Ser. No. 17/669,864, filed on Feb. 11, 2022, which claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 63/271,594, filed on Oct. 25, 2021, the entire contents of which are incorporated herein by reference. This application also claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 63/237,294, filed on Aug. 26, 2021, the entire contents of which are incorporated herein by reference.

Provisional Applications (2)
Number Date Country
63271594 Oct 2021 US
63237294 Aug 2021 US
Continuation in Parts (1)
Number Date Country
Parent 17669864 Feb 2022 US
Child 17875455 US