Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. The present disclosure provides a compound having a first ligand LA # imgabs0 # of Formula I wherein each of Z1, Z2 and X1 to X4 is C or N; part A is a monocyclic or polycyclic fused ring system; part C is a monocyclic or polycyclic fused ring system; k is selected from the group consisting of a direct bond, O, S, N (R [alpha]), P (R [alpha]), B (R [alpha]), C (R [alpha]) (R [beta]) and Si (R [alpha]) (R [beta]); y is a linking group; each R, R ', R alpha, R beta, R1, R2 and R3 is hydrogen or a universal substituent as defined herein; wherein one of the statements as defined herein is true. Formulations, OLEDs, and consumer products containing the compounds are also provided.

Description

[0001] Cross-reference to related applications

[0002] This application is a partial continuation of U.S. Patent Application No. 18 / 814,301, filed on August 23, 2024, and U.S. Patent Application No. 18 / 814,295, filed on August 23, 2024, the entire contents of both of which are incorporated herein by reference. This application also claims priority to U.S. Provisional Application No. 63 / 664,204, filed on June 26, 2024, U.S. Provisional Application No. 63 / 562,444, filed on March 7, 2024, U.S. Provisional Application No. 63 / 620,548, filed on January 12, 2024, U.S. Provisional Application No. 63 / 625,704, filed on January 26, 2024, and U.S. Provisional Application No. 63 / 614,955, filed on December 27, 2023, the entire contents of all of the above-referenced applications are incorporated herein by reference. Technical Field

[0003] The present disclosure generally relates to organic or metal coordination compounds and formulations and their various uses, including as emitters, sensitizers, charge transporters, or exciton transporters in devices such as organic light-emitting diodes and related electronic devices and consumer products. Background Art

[0004] For various reasons, optoelectronic devices that utilize organic materials have become increasingly popular. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. Additionally, the inherent properties of organic materials, such as their flexibility, can make them more suitable for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, organic scintillators, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

[0005] OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly attractive technology for applications such as displays, lighting, and backlighting.

[0006] One application of emissive molecules is full-color displays. Industry standards for such displays require pixels that are adapted to emit specific colors (referred to as "saturated" colors). Specifically, these standards require saturated red, green, and blue pixels. Alternatively, an OLED can be designed to emit white light. In a conventional liquid crystal display, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technique can also be used for OLEDs. A white OLED can be a single-emission layer (EML) device or a stacked structure. Color can be measured using CIE coordinates well known in the art. Summary of the Invention

[0007] In one aspect, the present disclosure provides a compound having a first ligand L with a structure comprising Formula I A ,

[0008] In Formula I:

[0009] Z 1 , Z 2 and X 1 to X 4 each independently is C or N;

[0010] Moiety A is a monocyclic or polycyclic fused-ring system, wherein each ring of the monocyclic and polycyclic fused-ring systems is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0011] Moiety C is a monocyclic or polycyclic fused-ring system, wherein each ring of the monocyclic or polycyclic fused-ring systems is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0012] K is selected from the group consisting of a direct bond, O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β );

[0013] Y is 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, CR, CRR', SiRR' and GeRR';

[0014] R 1 , R 2 and R 3 each independently represents mono-substitution to the maximum allowable substitution or no substitution;

[0015] Each R, R', Rα , R β , R 1 , R 2 and R 3 are independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boranyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;

[0016] Any two substituents may be joined or fused to form a ring;

[0017] L A is coordinated to a metal M having an atomic mass of at least 40;

[0018] The metal M may be coordinated with other ligands; and

[0019] L A may be joined to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0020] In another aspect, the present disclosure provides a formulation comprising a compound having a first ligand L A wherein the first ligand L A comprises the structure of Formula I as described herein.

[0021] In another aspect, the present disclosure provides an OLED having an organic layer comprising a compound having a first ligand L A wherein the first ligand L A comprises the structure of Formula I as described herein.

[0022] In another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound having a first ligand L A wherein the first ligand L A comprises the structure of Formula I as described herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 Shows an organic light emitting device.

[0024] Figure 2 Shows an inverted organic light emitting device without an independent electron transport layer. DETAILED DESCRIPTION

[0025] A. Terms

[0026] Unless otherwise specified, the following terms used herein are defined as follows:

[0027] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed over" a second layer, the first layer is disposed further from the substrate. There may be other layers between the first and second layers unless it is specified that the first layer "contacts" the second layer. For example, the cathode may be described as being "disposed over" the anode even though there are various organic layers between the cathode and the anode.

[0028] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0029] As used herein, and as would be generally understood by one of ordinary skill in the art, if a first energy level is closer to the vacuum level, then the 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. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram where the top is the vacuum level, 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 this diagram than a "lower" HOMO or LUMO energy level.

[0030] As used herein, and as would be generally understood by one of ordinary skill in the art, if a first work function has a higher absolute value, then the first work function is "greater than" or "higher than" a second work function. Since the work function is generally measured as a negative number relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram where the top is the vacuum level, a "higher" work function is illustrated as being further from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than the work function.

[0031] The present disclosure may describe layers, materials, regions, and devices in terms of the color of the light they emit. Generally, as used herein, an emission region described as producing a specific color of light may include one or more emission layers disposed over one another in a stacked manner.

[0032] As used herein, a "NIR," "red," "green," "blue," or "yellow" layer, material, region, or device refers to a layer, material, region, or device that emits light in a wavelength range of about 700-1500 nm, 580-700 nm, 500-600 nm, 400-500 nm, or 540-600 nm, respectively, or a layer, material, region, or device having the highest emission spectrum peak in the corresponding wavelength region. In some arrangements, separate regions, layers, materials, or devices may provide separate "deep blue" and "light blue" emissions. As used herein, a "deep blue" emission component refers to an emission having a peak emission wavelength that is at least about 4 nm less than the peak emission wavelength of a "light blue" emission component. Typically, the peak emission wavelength of the "light blue" emission component is in the range of about 465-500 nm, and the peak emission wavelength of the "deep blue" emission component is in the range of about 400-470 nm, but these ranges may vary for some configurations.

[0033] In some arrangements, a color-changing layer is provided that converts, modifies or changes the color of light emitted by another layer to an emission having a different wavelength. This color-changing layer can be configured to shift the wavelength of light emitted by another layer by a defined amount, as measured by the difference between the wavelength of the emitted light and the wavelength of the resulting light. In general, there are two types of color-changing layers: color filters that modify the spectrum by removing light of non-desired wavelengths, and color-changing layers that convert higher energy photons into lower energy. For example, there may be a "red" filter to filter the input light to remove light with wavelengths outside the range of about 580-700nm. A component of "color" refers to a component that produces or otherwise emits light having a specific color as previously described when activated or used. For example, a "first emission region of a first color" and a "second emission region of a second color different from the first color" describe two emission regions that emit two different colors as previously described when activated within the device.

[0034] As used herein, emissive materials, layers, and regions may be distinguished from each other and from other structures based on the light that the material, layer, or region initially produces as opposed to the light that the same or different structure ultimately emits. Initial light generation is typically the result of a change in energy levels that results in photon emission. For example, an organic emissive material may initially produce blue light, which may be converted to red or green light by a color filter, quantum dots, or other structure, such that the complete emissive stack or sub-pixel emits red or green light. In this case, the initial emissive material, region, or layer may be referred to as the "blue" component, even if the sub-pixel is the "red" or "green" component.

[0035] In some cases, it may be preferable to describe the color of a component, such as the color of an emission region, a subpixel, a color-changing layer, etc., according to 1931 CIE coordinates. For example, a yellow-emitting material may have multiple peak emission wavelengths, one in or near the edge of the "green" region and one in or near the edge of the "red" region, as previously described. Thus, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. The shape in the 1931 CIE color space is constructed by tracing the locus between two color points and any other internal points. For example, the internal shape parameters for red, green, blue, and yellow can be defined as follows:

[0036]

[0037] The terms "halo", "halogen", and "halo group" may be used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0038] The term "acyl group" refers to a substituted carbonyl group (-C(O)-R s ).

[0039] The term "ester" refers to a substituted oxycarbonyl group (-O-C(O)-R s or -C(O)-O-R s ).

[0040] The term "ether" refers to an -OR s group.

[0041] The terms "sulfanyl" or "thioether" may be used interchangeably and refer to an -SR s group.

[0042] The term "selenoalkyl" refers to a -SeR s group.

[0043] The term "sulfinyl" refers to a -S(O)-R s group.

[0044] The term "sulfonyl" refers to a -SO2-R s group.

[0045] The term "phosphino" refers to a group containing at least one phosphorus atom bonded to the relevant structure. Common examples of phosphino groups include, but are not limited to, groups such as -P(R s )2 group or -PO(R s )2 group, where each R s can be the same or different.

[0046] The term "silyl" refers to a group containing at least one silicon atom bonded to the relevant structure. Common examples of silyl groups include, but are not limited to, groups such as -Si(R s)3 group, where each R s may be the same or different.

[0047] The term "germyl" refers to a group containing at least one germanium atom bonded to the relevant structure. Common examples of germyl include, but are not limited to, groups such as -Ge(R s )3 group, where each R s may be the same or different.

[0048] The term "boryl" refers to a group containing at least one boron atom bonded to the relevant structure. Common examples of boryl include, but are not limited to, groups such as -B(R s )2 group or its Lewis adduct -B(R s )3 group, where R s may be the same or different.

[0049] In each of the above, R s may be hydrogen or a substituent selected from the group consisting of general substituents as defined in the present application. Preferred R s is selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof. More preferably, R s is selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof.

[0050] The term "alkyl" refers to and includes both straight-chain and branched-chain alkyls having alkyl carbon atoms bonded to the relevant structure. Preferred alkyls are alkyls containing one to fifteen carbon atoms, preferably one to nine carbon atoms, and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. Additionally, the alkyl may be further substituted.

[0051] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spirocycloalkyls having cycloalkyl carbon atoms bonded to the relevant structure. Preferred cycloalkyls are cycloalkyls containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, the cycloalkyl may be further substituted.

[0052] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group having at least one carbon atom replaced by a heteroatom, respectively. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Additionally, the heteroalkyl or heterocycloalkyl may be further substituted.

[0053] The term "alkenyl" refers to and includes both straight-chain and branched-chain olefin groups. An alkenyl is essentially an alkyl group that includes at least one carbon-carbon double bond in the alkyl chain, where one of the carbon atoms is from the carbon-carbon double bond bonded to the relevant structure. A cycloalkenyl is essentially a cycloalkyl group that includes at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing from two to fifteen carbon atoms. Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl may be further substituted.

[0054] The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne groups. An alkynyl is essentially an alkyl group that includes at least one carbon-carbon triple bond in the alkyl chain, where one of the carbon atoms is from the carbon-carbon triple bond bonded to the relevant structure. Preferred alkynyl groups are those containing from two to fifteen carbon atoms. Additionally, the alkynyl may be further substituted.

[0055] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an aryl-substituted alkyl group having an alkyl carbon atom bonded to the relevant structure. Additionally, the aralkyl may be further substituted.

[0056] The term "heterocyclic group" refers to and includes aromatic and non-aromatic ring groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, Se, N, P, B, Si, Ge, and Se, preferably O, S, N, or B. A heteroaromatic ring group may be used interchangeably with a heteroaryl. Preferred non-aromatic heterocyclic groups are non-aromatic heterocyclic groups containing from 3 to 10 ring atoms, preferably non-aromatic heterocyclic groups containing from 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines such as morpholinyl, piperidinyl, pyrrolidinyl, etc., and cyclic ethers / sulfides such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Additionally, the heterocyclic group may be further substituted or fused.

[0057] The term "aryl" means and includes both monocyclic and polycyclic aromatic hydrocarbon groups. The polycycle can have two or more rings, where two carbons are common to two adjacent rings (the rings are "fused"). Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty-four carbon atoms, six to eighteen carbon atoms, and more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, twelve, fourteen or eighteen carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluorene, phenanthrene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene and naphthalene. Additionally, the aryl group can be further substituted or fused, such as but not limited to fluorene.

[0058] The term "heteroaryl" means and includes both monocyclic aromatic groups having at least one heteroatom and polycyclic aromatic ring systems. Heteroatoms include, but are not limited to, O, S, Se, N, P, B, Si, Ge and Se. In many cases, O, S, N or B are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring can have one to six heteroatoms. The polycyclic heterocyclic system can have two or more aromatic rings, where two atoms are common to two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl. The polycyclic heteroaromatic ring system can have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and 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, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, azaborane, borazine, 5λ 2 ,9λ 2 -diazab-13b-boraphenanthro[2,3,4-de]anthracene, 5λ 2-Benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 5λ 2 ,9λ 2 -diazaboranaphtho[2,3,4-de]anthracene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene. Additionally, the heteroaryl may be further substituted or fused.

[0059] Among the aryl and heteroaryl listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 5λ 2 ,9λ 2 -diazaboranaphtho[2,3,4-de]anthracene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene groups, and their corresponding aza analogs are of particular interest.

[0060] In many cases, the general substituents are selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenyl, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0061] In some cases, the preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio and combinations thereof.

[0062] In some cases, the more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, aryl, heteroaryl, nitrile, thio and combinations thereof.

[0063] In some cases, the even more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile and combinations thereof.

[0064] In other other cases, the most preferred general substituents are selected from the group consisting of: deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0065] The terms "substituted" and "substitution" mean that a substituent other than H is bonded to the relevant position, such as carbon or nitrogen. For example, when R 1 represents monosubstitution, then one R 1 must not be H (i.e., substitution). Similarly, when R 1 represents disubstitution, then two R 1 must not be H. Similarly, when R 1 represents zero or no substitution, R 1 can be, for example, hydrogen at all available valences of the ring atoms, such as the carbon atoms in benzene and the nitrogen atom in pyrrole, or simply represent none for a ring atom with fully saturated valences, such as the nitrogen atom in pyridine. The maximum possible number of substitutions in a ring structure will depend on the total number of available valences in the ring atoms.

[0066] As used herein, "combinations thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that a person of ordinary skill in the art can envision from the applicable list. For example, an alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; a halogen and an alkyl can be combined to form a haloalkyl substituent; and a halogen, an alkyl, and an aryl can be combined to form a haloaryalkyl. In one example, the term substitution includes combinations of two to four of the listed groups. In another example, the term substitution includes combinations of two to three groups. In yet another example, the term substitution includes combinations of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, the preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0067] The "aza" name in the fragments described herein, such as aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic ring can be replaced by a nitrogen atom. For example, and without any limitation, aza-triphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Those 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 covered by the terms as set forth herein.

[0068] 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. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US2011 / 0037057 (which are incorporated herein by reference in their entireties) describe the preparation 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. (Review) 2007, 46, 7744-65 (which are incorporated by reference in their entireties) which respectively describe effective routes for the deuteration of methylene hydrogens in benzylamines and the replacement of aromatic ring hydrogens with deuterium.

[0069] As used herein, any specifically listed substituent, such as but not limited to methyl, phenyl, pyridyl, etc. includes its non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituents such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc. also include their non-deuterated, partially deuterated, and fully deuterated forms. Unless otherwise specified, atoms in a chemical structure that do not have valences fully filled by H or D should be considered to include their non-deuterated, partially deuterated, and fully deuterated forms. For example, the chemical structure is meant to include C6H6, C6D6, C6H3D3, and any other of its partially deuterated variants. Some common substantially or fully deuterated groups include but are not limited to CD3, CD2C(CH3)3, C(CD3)3, and C6D5.

[0070] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attached fragments are considered equivalent.

[0071] In some cases, a pair of substituents in a molecule can optionally be joined or fused to form a ring. Preferred rings are five- to nine-membered carbocyclic or heterocyclic rings, including cases where the portion of the ring formed by the pair of substituents is saturated and cases where the portion of the ring formed by the pair of substituents is unsaturated. In still other cases, a pair of adjacent substituents can optionally be joined or fused to form a ring. As used herein, "adjacent" means that the two substituents involved can be next to each other on the same ring or on two adjacent rings having the two closest available substitutable positions (such as the 2, 2'-positions in biphenyl or the 1, 8-positions in naphthalene).

[0072] B. Compounds of the Present Disclosure

[0073] The compounds disclosed herein exhibit improved properties when incorporated into OLEDs. The improved properties include a narrower emission spectrum (full width at half maximum) and a reduced transient lifetime.

[0074] In one aspect, the present disclosure provides a compound having a first ligand L having a structure comprising Formula I A ,

[0075] In Formula I:

[0076] Z 1 , Z 2 and X 1 to X 4 each independently is C or N;

[0077] Moiety A is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic and polycyclic fused ring systems is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0078] Moiety C is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring systems is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0079] K is selected from the group consisting of a direct bond, O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ) and Si(R α )(R β );

[0080] Y is 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, CR, CRR', SiRR' and GeRR';

[0081] R 1 , R 2 and R 3 each independently represents mono-substitution to the maximum allowable substitution or no substitution;

[0082] Each R, R', R α , R β , R 1 , R 2 and R 3 is independently hydrogen, or a substituent selected from the group of general substituents defined herein;

[0083] Any two substituents may be joined or fused to form a ring;

[0084] L A is coordinated to a metal M having an atomic mass of at least 40;

[0085] The metal M may be coordinated to other ligands; and

[0086] L A may be joined to other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

[0087] In some embodiments, the compound is not

[0088] In some embodiments, moiety C is a polycyclic fused ring system, and ring B or the ring formed by two Rs 2 and moiety C together contain at least two N ring atoms.

[0089] In some embodiments, moiety C contains three or more fused 5- to 10-membered carbocyclic or heterocyclic rings, and ring B and moiety C together contain at least one N ring atom.

[0090] In some embodiments, moiety A is a monocyclic 6-membered aromatic ring containing one or more N atoms, moiety C is a fused bicyclic structure composed of a 6-membered ring and a heterocyclic ring, wherein the 6-membered ring is fused to ring B1, and wherein ring B or moiety C contains at least one N atom; or at least one R 2 or R 3 contains an electron-withdrawing group.

[0091] In some embodiments, moiety A is a monocyclic 6-membered aromatic ring containing one or more N atoms, moiety C is a monocyclic ring, and two Rs 2 are joined to form moiety I, wherein moiety I is a heterocyclic or heterocyclic fused ring system, and each ring of the heterocyclic and heterocyclic fused ring systems is independently a 5- or 6-membered carbocyclic or heterocyclic ring.

[0092] In some embodiments, one of the following statements is true:

[0093] (1) Moiety C is a polycyclic fused ring system, and ring B or the ring formed by two Rs 2 and moiety C together contain at least two N ring atoms.

[0094] (2) Moiety C contains three or more fused 5- to 10-membered carbocyclic or heterocyclic rings, and ring B and moiety C together contain at least one N ring atom;

[0095] (3) Moiety A is a monocyclic 6-membered aromatic ring containing one or more N atoms, and moiety C is a fused bicyclic structure composed of a 6-membered ring and a heterocyclic ring, wherein the 6-membered ring is fused to ring B1, and wherein ring B or moiety C contains at least one N atom; or at least one R 2 or R 3 contains an electron-withdrawing group; or

[0096] (4) Moiety A is a monocyclic 6-membered aromatic ring containing one or more N atoms, moiety C is a monocyclic ring, and two Rs 2 are joined to form moiety I, wherein moiety I is a heterocyclic ring or a heterocyclic fused-ring system, and each ring of the heterocyclic ring and the heterocyclic fused-ring system is independently a 5-membered or 6-membered carbocyclic ring or heterocyclic ring.

[0097] In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then at least one of X 1 to X 4 is N. In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then exactly one of X 1 to X 4 is N.

[0098] In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then at least one R A is a substituent other than hydrogen. In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then at least one R A is alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl, an electron-withdrawing group, or a combination thereof.

[0099] In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then the benzo group of the benzimidazole bicyclic structure is substituted with a substituent other than hydrogen. In some embodiments, when moiety C is a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1, then the benzo group of the benzimidazole bicyclic structure is substituted with alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl, an electron-withdrawing group, or a combination thereof.

[0100] In some embodiments, moiety C is not a benzimidazole bicyclic structure in which the benzo part of the benzimidazole bicyclic structure is fused to ring B1.

[0101] In some embodiments, when moiety C is a bicyclic fused-ring structure, each ring of the bicyclic fused-ring structure has at least one N ring atom.

[0102] In some embodiments, when moiety C is a bicyclic fused-ring structure, each ring of the bicyclic fused-ring structure has exactly one N ring atom.

[0103] In some embodiments, when moiety C is a bicyclic fused-ring structure and each of X 1 through X 4 is independently C, then each ring of the bicyclic fused-ring structure has at least one N ring atom.

[0104] In some embodiments, when moiety C is a bicyclic fused-ring structure and each of X 1 through X 4 is independently C, then each ring of the bicyclic fused-ring structure has exactly one N ring atom.

[0105] In some embodiments, K is a direct bond. In some embodiments, K is O.

[0106] In some embodiments, if moiety C contains two rings and the terminal ring contains two N ring atoms, then moiety A is not imidazole. In some embodiments, moiety C contains two rings and the terminal ring contains two N ring atoms, and moiety A is not imidazole.

[0107] In some embodiments, the first ligand L A has the structure of Formula I. In some embodiments, the first ligand L A consists essentially of Formula I.

[0108] In some embodiments, at least one of R 1 , R 2 or R 3 is selected from the group consisting of the general substituents defined herein. In some embodiments, at least one of R 1 is selected from the group consisting of the general substituents defined herein. In some embodiments, at least one of R 2 is selected from the group consisting of the general substituents defined herein. In some embodiments, at least one of R 3 is selected from the group consisting of the general substituents defined herein.

[0109] In some embodiments of Formula I, at least one of R, R', R 1 , R 2 and R 3 is partially or fully deuterated. In some embodiments, at least one of R 1 is partially or fully deuterated. In some embodiments, at least one of R 2 is partially or fully deuterated. In some embodiments, at least one of R 3is partially or fully deuterated. In some embodiments, at least one of R or R' is partially or fully deuterated.

[0110] In some embodiments, moiety A is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic and polycyclic fused ring systems is independently a 5- or 6-membered carbocyclic or heterocyclic ring. In some embodiments, moiety A is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic and polycyclic fused ring systems is independently a 5- or 6-membered aryl or heteroaryl ring.

[0111] In some embodiments, moiety C is a polycyclic fused ring system, wherein each ring of the polycyclic fused ring system is independently a 5- or 6-membered carbocyclic or heterocyclic ring. In some embodiments, moiety C is a polycyclic fused ring system, wherein each ring of the polycyclic fused ring system is independently a 5- or 6-membered aryl and heteroaryl ring.

[0112] In some embodiments, each R, R', R 1 , R 2 and R 3 is independently hydrogen, or a substituent selected from the group consisting of preferred general substituents as defined herein. In some embodiments, each R, R', R 1 , R 2 and R 3 is independently hydrogen, or a substituent selected from the group consisting of more preferred general substituents as defined herein. In some embodiments, each R, R', R 1 , R 2 and R 3 is independently hydrogen, or a substituent selected from the group consisting of most preferred general substituents as defined herein.

[0113] In some embodiments, metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu. In some embodiments, metal M is Ir. In some embodiments, metal M is Pt or Pd. In some embodiments, metal M is Pt. In some embodiments, metal M is Pd.

[0114] In some embodiments, Z 1 is N and Z 2 is C. In some embodiments, Z 1 is a carbene carbon and Z 2 is N.

[0115] In some embodiments, Z 1 and Z 2 are both C.

[0116] In some embodiments, X 1 to X 4Each of them is C. In some embodiments, X 1 to X 4 at least one of which is N. In some embodiments, X 1 to X 4 exactly one of which is N.

[0117] In some embodiments, one of X 1 to X 4 bonded to moiety A is C.

[0118] In some embodiments, one of X 1 to X 4 bonded to metal M is C. In some embodiments, one of X 1 to X 4 bonded to metal M is N.

[0119] In some embodiments, moiety A is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, benzo-benzimidazole, aza-benzo-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, the aza-variant includes one N on the benzo ring. In some embodiments, the aza-variant includes one N on the benzo ring and the N is bonded to the Ir atom.

[0120] In some embodiments, moiety A is monocyclic. In some embodiments, moiety A is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole. In some embodiments, moiety A is pyridine, imidazole-derived carbene, or imidazole. In some embodiments, moiety A is pyridine. In some embodiments, moiety A is imidazole.

[0121] In some embodiments, moiety A is a polycyclic fused-ring system. In some embodiments, moiety A is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, aza-benzimidazole-derived carbene, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, moiety A is quinoline, isoquinoline, or benzimidazole. In some embodiments, moiety A is quinoline. In some embodiments, moiety A is isoquinoline. In some embodiments, moiety A is benzimidazole.

[0122] In some embodiments, moiety A can be a polycyclic fused-ring structure. In some embodiments, moiety A can be a polycyclic fused-ring structure comprising at least two fused rings. In some embodiments, the polycyclic fused-ring structure has a 6-membered ring and a 5-membered ring. In some such embodiments, the 5-membered ring or the 6-membered ring can coordinate to a metal. In some embodiments, the polycyclic fused-ring structure has two 6-membered rings. In some embodiments, moiety A can be selected from the group consisting of benzofuran, benzothiophene, benzoselenophene, naphthalene, and their aza-variants.

[0123] In some embodiments, moiety A can be a polycyclic fused-ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused-ring structure has two 6-membered rings and a 5-membered ring. In some such embodiments, the 5-membered ring is fused to a ring coordinated to metal M, and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, moiety A can be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and their aza-variants. In some such embodiments, moiety A can be further substituted at the ortho or meta position of the O, S, or Se atom with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza-variant contains exactly one N atom at the 6-position (ortho to O, S, or Se) and has a substituent at the 7-position (meta to O, S, or Se).

[0124] In some embodiments, moiety A can be a 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 metal M, 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 with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0125] In some embodiments, moiety A can be a 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 having one 5-membered ring, the 5-membered ring is fused to the ring coordinated to metal M, 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.

[0126] In some embodiments, moiety A can be the aza form of the polycyclic fused-ring described above. In some such embodiments, moiety A can contain exactly one aza N atom. In some such embodiments, moiety A can contain exactly two aza N atoms, which can be in one ring or in two different rings. In some such embodiments, the ring having the aza N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring having the aza N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each of the ortho positions of the aza N atom is substituted.

[0127] In some embodiments, moiety C is a polycyclic fused-ring system. In some embodiments, moiety C is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, aza-benzimidazole-derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, moiety C is quinoline, isoquinoline, or quinazoline.

[0128] In some embodiments, Ring B and moiety C together contain at least two N ring atoms. In some embodiments, Ring B and moiety C together contain at least three N ring atoms. In some embodiments, Ring B contains at least one N ring atom.

[0129] In some embodiments, moiety C contains two fused rings.

[0130] In some embodiments, one of X 1 to X 4 is N, and moiety C contains at least one N ring atom. In some such embodiments, moiety C is quinoline or isoquinoline. In some embodiments, moiety C is quinazoline.

[0131] In some embodiments, moiety C contains three or more 5- to 10-membered carbocyclic or heterocyclic rings, and Ring B and moiety C together contain at least one N ring atom. In some such embodiments, moiety C contains three 5- to 10-membered carbocyclic or heterocyclic rings. In some embodiments, moiety C contains four or more 5- to 10-membered carbocyclic or heterocyclic rings.

[0132] In some embodiments, moiety C contains three or more 5- or 6-membered carbocyclic or heterocyclic rings. In some embodiments, moiety C contains three or more 5- or 6-membered aryl or heteroaryl rings.

[0133] In some embodiments, moiety C is selected from the group consisting of carbazole, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, quinoxaline, phthalazine, aza-phenanthrene, aza-anthracene, phenanthridine, and aza-fluorene.

[0134] In some embodiments, the ring of moiety C fused to the Y-containing ring is benzene. In some embodiments, the ring of moiety C fused to the Y-containing ring contains at least one heteroatom. In some embodiments, the ring of moiety C fused to the Y-containing ring contains at least one N atom.

[0135] In some embodiments, moiety C contains at least two N ring atoms. In some embodiments, moiety C contains at least three N ring atoms.

[0136] In some embodiments, Y is selected from the group consisting of O, S, and Se. In some embodiments, Y is O. In some embodiments, Y is S. In some embodiments, Y is Se.

[0137] In some embodiments, Y is selected from the group consisting of BR, NR, and PR. In some embodiments, Y is selected from the group consisting of BRR', CRR', SiRR', and GeRR'. In some embodiments, Y is selected from the group consisting of P(O)R, C═O, C═S, C═Se, C═NR', C═CRR', S═O, and SO2. In some embodiments, Y is selected from CR.

[0138] In some embodiments of Formula I, Ring B, Ring B1, and moiety C together contain only one N ring atom. In some such embodiments, moiety C contains the sole N atom and is on the ring fused to Ring B1. In some such embodiments, moiety C contains the sole N atom and is on the ring remote from Ring B1. In some such embodiments, moiety C contains two fused 6-membered rings, and the sole N atom is on the 6-membered ring fused to Ring B1. In some such embodiments, moiety C contains two fused 6-membered rings, and the sole N atom is on the 6-membered ring remote from Ring B1.

[0139] In some embodiments of Formula I, moiety C contains all 6-membered rings. In some embodiments, moiety C contains only one 5-membered ring and the rest are 6-membered rings. In some embodiments, moiety C contains two 6-membered rings. In some embodiments, moiety C contains one 6-membered ring and one 5-membered ring. In some such embodiments, moiety C contains only one ring N atom, and neither Ring B nor Ring B1 contains any ring N atoms. In some embodiments, moiety C contains three 6-membered rings. In some embodiments, moiety C contains two 6-membered rings and one 5-membered ring. In some such embodiments, moiety C contains only one ring N atom, and neither Ring B nor Ring B1 contains any ring N atoms. In some such embodiments, the 6-membered moiety C ring fused to Ring B1 contains the sole ring N atom.

[0140] In some embodiments, the compound contains an electron-withdrawing group. In some embodiments, the Hammett constant of the electron-withdrawing group is greater than 0. In some embodiments, the Hammett constant of the electron-withdrawing group is equal to or greater than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.

[0141] In some embodiments, Formula I contains an electron-withdrawing group selected from the group consisting of the following list of EWG1: F, CF3, CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3, (R k2 )2CCN, (R k2 )2CCF3, CNC(CF3)2, BR k3 R k2, substituted or unsubstituted dibenzoborolene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridoxine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated alkyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyanoalkyl, cyanoaryl, cyanoheteroaryl, isocyanate,

[0142] wherein each R k1 represents mono-substitution to the maximum allowable substitution or no substitution;

[0143] wherein Y G is selected from the group consisting of: BR e , NR e , PR e , O, S, Se, C═O, S═O, SO2, CR e R f , SiR e R f and GeR e R f ; and

[0144] wherein each of R k1 , R k2 , R k3 , R e and R f is independently hydrogen or a substituent selected from the group of general substituents defined herein.

[0145] In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of the structures in the following EWG2 list:

[0146]

[0147]

[0148]

[0149] In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of the structures in the following EWG3 list:

[0150]

[0151]

[0152] In some embodiments, Formula I includes an electron-withdrawing group selected from the group consisting of the structures in the following EWG4 list:

[0153]

[0154] In some embodiments, Formula I includes an electron-withdrawing group, and the electron-withdrawing group is a π-deficient electron-withdrawing group. In some embodiments, the π-deficient electron-withdrawing groups are selected from the group consisting of the structures in the following π-EWG list: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3, BR k2 R k3 , substituted or unsubstituted dibenzoborolene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,

[0155] wherein the variables are the same as previously defined.

[0156] In some embodiments, the compound includes an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, the compound includes an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, the compound includes an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, the compound includes an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, the compound includes an electron-withdrawing group from the π-EWG list as defined herein.

[0157] In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0158] In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0159] In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0160] In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0161] In some embodiments, at least one R 1 is not H. In some embodiments, at least one R 1 comprises at least one C atom. In some embodiments, at least one R 1 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0162] In some embodiments, at least two R 1 each independently comprise a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some embodiments, at least two R 1 are independently alkyl. In some embodiments, at least two R 1 each independently comprise at least two C atoms. In some embodiments, at least two R 1 each independently comprise at least three C atoms.

[0163] In some embodiments, at least one R 2 is not H. In some embodiments, at least one R 2 comprises at least one C atom. In some embodiments, at least one R 2 comprises a substituent selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0164] In some embodiments, at least one R 3 is not H. In some embodiments, at least one R 3 comprises at least one C atom. In some embodiments, at least one R 3 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0165] In some embodiments, at least two R 3 each independently comprise a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, at least one R 3Contains an aryl group. In some such embodiments, at least one R 3 is an alkyl group. In some embodiments, at least one R 3 contains an aryl group, and at least one R 3 is an alkyl group.

[0166] In some embodiments, ligand L A is selected from the group consisting of the structures of List 1 below:

[0167]

[0168]

[0169] Wherein:

[0170] Each of X1 to X 20 is independently C or N;

[0171] Y B1 and Y B2 are each 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, CR, CRR', SiRR' and GeRR';

[0172] R A , R B and R C each independently represents mono-substituted to the maximum allowable substitution or unsubstituted;

[0173] Each R, R', R A , R B , R C and R N is independently hydrogen or a substituent selected from the group of general substituents defined herein;

[0174] Any two substituents may be joined or fused to form a ring; and one of the conditions is true, as specified previously for the fused bottom ring system of each structure.

[0175] In some embodiments where ligand L A is selected from List 1, at least one of X5 to X 20 in the structure is N. In some embodiments, exactly one of X5 to X 20 in the bottom fused polycyclic system is N. In some such embodiments, exactly one of X9 to X 12 in the bottom fused polycyclic system is N. In some such embodiments, X 13 to X 16Exactly one of them is N. In some such embodiments, X in the bottom-fused polycyclic system 17 to X 20 Exactly one of them is N. In some embodiments, at least two of X5 to X in the structure 20 are N. In some embodiments, a separate ring of the structure can contain one and only one N. In some embodiments, a separate ring of the structure can contain at most 2 N atoms. In some embodiments, at most three of X1 to X 20 can be N atoms in the structure. In some such embodiments, each N atom is in a separate and different ring. In some embodiments, X 6 is carbon and is connected to R 6 of X B selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, X 6 is carbon and is connected to R 6 of X B is alkyl, cycloalkyl, or silyl. In some embodiments, X 6 is carbon and is connected to R 6 of X B is a tertiary carbon. In some embodiments, X 6 is carbon and is connected to R 6 of X B is tert-butyl, CH3, or CD3. In some embodiments, two R A are fused to form a ring or a fused ring system. In some embodiments, the fused ring or the fused ring system can be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, aza-benzimidazole-derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, or aza-fluorene. In some such embodiments, the fused ring or the fused ring system can be benzene or naphthalene. In some such embodiments, the fused ring can be benzene. In some such embodiments, the fused ring system can be naphthalene.

[0176] In some embodiments where the ligand L A is selected from List 1, at least one of R A , R B , or R CSelect from the group consisting of the general substituents defined herein. In some embodiments, at least one R A Select from the group consisting of the general substituents defined herein. In some embodiments, at least one R B Select from the group consisting of the general substituents defined herein. In some embodiments, at least one R C Select from the group consisting of the general substituents defined herein.

[0177] In ligand L A In some embodiments selected from List 1, R, R', R A , R B , R C or R N is at least partially or fully deuterated. In some embodiments, at least one R A is at least partially or fully deuterated. In some embodiments, at least one R B is at least partially or fully deuterated. In some embodiments, at least one R C is at least partially or fully deuterated. In some embodiments, at least one R N is at least partially or fully deuterated. In some embodiments, R or R', if present, is at least partially or fully deuterated.

[0178] In ligand L A In some embodiments selected from List 1, at least one R A is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0179] In ligand L A In some embodiments selected from List 1, at least one R B is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R Bis or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0180] In some embodiments of ligand L A selected from List 1, at least one R C is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0181] In some embodiments of ligand L A selected from List 1, at least one R N is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0182] In some embodiments of ligand L A selected from List 1, at least one R or R' is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0183] In some embodiments, ligand LA Select from the group consisting of the structures in List 2 below:

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] wherein

[0195] each of X1 to X 14 is independently C or N;

[0196] Y B1 and Y B2 are each 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, CR, CRR', SiRR' and GeRR';

[0197] R A 、R B and R C each independently represents mono-substitution to the maximum allowable substitution or no substitution;

[0198] each R, R', R A 、R B 、R C and R N is independently hydrogen or a substituent selected from the group of general substituents defined herein;

[0199] Any two substituents may be joined or fused to form a ring; and one condition is true, as specified previously for the fused bottom ring system of each structure.

[0200] In some embodiments, ligand L ASelect from the group consisting of the structures in List 2a below:

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] wherein all variables are the same as previously defined; and any two substituents may optionally be joined or fused to form a ring.

[0207] In ligand L A In some embodiments selected from List 2 or some embodiments of List 2a, X of the fused benzene ring of benzimidazole in the structure 1 and X 2 are both carbon, and are respectively fused with two R A connected thereto to form a ring. Similarly, in some embodiments, X of the fused benzene ring of benzimidazole in the structure 2 and X 3 are both carbon, and are respectively fused with two R A connected thereto to form a ring. Likewise, in some embodiments, X of the fused benzene ring of benzimidazole in the structure 3 and X 4 are both carbon, and are respectively fused with two R A connected thereto to form a ring. In some such embodiments, the fused ring can be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole or triazole. In some such embodiments, the fused ring can be benzene.

[0208] In some embodiments, ligand L A is selected from the group consisting of the following structures (List 2b):

[0209] wherein each of X 15 to X 20 is independently C or N; and the remaining variables are the same as previously defined or as defined in the present disclosure; and any two substituents may optionally be fused or joined to form a ring.

[0210] In some embodiments where ligand L A is selected from List 2, List 2a or List 2b, at least one R BNot H. In some embodiments, at least one R B is selected from the group consisting of the general substituents defined herein. In some embodiments, at least one R B is selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, X 6 is carbon and the R 6 connected to X B is selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, X 6 is carbon and the R 6 connected to X B is alkyl, cycloalkyl or silyl. In some embodiments, X 6 is carbon and the R 6 connected to X B is a tertiary carbon. In some embodiments, X 6 is carbon and the R 6 connected to X B is tert-butyl, CH3 or CD3. In some embodiments, at least one R C is not H. In some embodiments, at least one R C is selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, at least two R C are not H. In some embodiments, at least two R C are each independently selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, at least one R A is not H. In some embodiments, at least one R A is selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, at least two R A are not H. In some embodiments, at least two R A are each independently selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, two R A fuse to form a ring. In some such embodiments, the fused ring can be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, or triazole. In some such embodiments, the fused ring can be benzene. In some embodiments, only X 12 is N. In some embodiments, only X9 is N. In some embodiments, R N is a substituted biphenyl. In some embodiments, RN is a carbon ring-substituted phenyl. In some embodiments, R N or R T is a heterocyclic ring-substituted phenyl.

[0211] In some embodiments where ligand L A is selected from List 2b, all embodiments of R T can be equally applied to the structures of List 2a.

[0212] In some embodiments where ligand L A is selected from List 2 or List 2a or List 2b, at least one of X5 to X 14 in the structure is N. In some embodiments, at least two of X5 to X 14 in the structure are N. In some embodiments, a single ring of the structure can contain one and only one N. In some embodiments, a single ring of the structure can contain at most 2 N atoms. In some embodiments, at most three of X1 to X 14 can be N atoms in the structure. In some such embodiments, each N atom is in a separate and distinct ring.

[0213] In some embodiments where ligand L A is selected from List 2 or List 2a or List 2b, at least one of R A , R B or R C is selected from the group consisting of general substituents defined herein. In some embodiments, at least one of R A is selected from the group consisting of general substituents defined herein. In some embodiments, at least one of R B is selected from the group consisting of general substituents defined herein. In some embodiments, at least one of R C is selected from the group consisting of general substituents defined herein.

[0214] In some embodiments where ligand L A is selected from List 2 or List 2a or List 2b, at least one of R, R', R A , R B , R C or R N is partially or fully deuterated. In some embodiments, at least one of R A is partially or fully deuterated. In some embodiments, at least one of R B is partially or fully deuterated. In some embodiments, at least one of R C is partially or fully deuterated. In some embodiments, at least one of R Nis partially or fully deuterated. In some embodiments, R or R', if present, is partially or fully deuterated.

[0215] In ligand L A In some embodiments selected from List 2 or List 2a or List 2b, at least one R A is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0216] In ligand L A In some embodiments selected from List 2 or List 2a or List 2b, at least one R B is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0217] In ligand L A In some embodiments selected from List 2 or List 2a or List 2b, at least one R C is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0218] In ligand L A In some embodiments selected from List 2 or List 2a or List 2b, at least one R N is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R N is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0219] In some embodiments, ligand L A is selected from the group consisting of the structures of List 2c below:

[0220]

[0221]

[0222]

[0223] wherein X 1 to X 6 are each independently C or N; R A , R B , R C and R D each independently represents mono-substitution to the maximum allowable substitution or no substitution; each R A , R B , R C and R D are independently hydrogen or a substituent selected from the group consisting of the general substituents as defined herein; the remaining variables are the same; and at least one of X 1 to X 6 is N; and any two substituents may optionally be joined or fused to form a ring.

[0224] In some embodiments where ligand L A is selected from List 2c, at least one R A , R B , R C or R D is selected from the group consisting of the general substituents as defined herein. In some embodiments, at least one R ASelect from the group consisting of the general substituents defined herein. In some embodiments, at least one R B Select from the group consisting of the general substituents defined herein. In some embodiments, at least one R C Select from the group consisting of the general substituents defined herein. In some embodiments, at least one R D Select from the group consisting of the general substituents defined herein. In some embodiments, X 1 to X 6 At least two of are N.

[0225] In some embodiments, ligand L A Select from the group consisting of the following structures (Listing 2d):

[0226]

[0227] Wherein all variables are the same as previously defined; and any two substituents may optionally be joined or fused to form a ring.

[0228] In ligand L A In some embodiments selected from Listing 2c or Listing 2d, at least one R B is not H. In some embodiments, at least one R B Select from the group consisting of the general substituents defined herein. In some embodiments, at least one R B Select from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, at least one R A is not H. In some embodiments, at least one R A Select from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, at least two R A are not H. In some embodiments, at least two R A Each independently select from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, two R A are fused to form a ring. In some such embodiments, the fused ring can be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, or triazole. In some such embodiments, the fused ring can be benzene. In some embodiments, only X 1 is N. In some embodiments, only X 2 is N. In some embodiments, only X 3 is N. In some embodiments, X 6 is carbon and is connected to X6 R of B is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof. In some embodiments, X 6 is carbon and is attached to the R of X 6 R of B is alkyl, cycloalkyl, or silyl. In some embodiments, X 6 is carbon and is attached to the R of X 6 R of B is tertiary carbon. In some embodiments, X 6 is carbon and is attached to the R of X 6 R of B is tert-butyl, CH3, or CD3. In some embodiments, at least one R D is a substituted or unsubstituted phenyl moiety. In some embodiments, at least one R D is a substituted or unsubstituted heteroaryl moiety.

[0229] In some embodiments, the ligand L A is selected from L Ai , where i is an integer from 1 to 582, and where each of L A1 to L A582 is defined in Listing 3 below:

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259] In some embodiments, ligand L A is selected from the group consisting of L Ai' -(Rm)(Rn)(Ro)(Rp)(Rq), where i' is an integer from 1 to 111, and each of Rm, Rn, Ro, Rp, and Rq is independently selected from the group consisting of R1 to R130; where L A1 (R1)(R1)(R1)(R1)(R1) to L A111 (R130)(R130)(R130)(R130)(R130) is defined in List 3a below:

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269] Wherein R1 to R130 have the structures in the following list:

[0270]

[0271]

[0272] In some embodiments, the ligand L A is selected from the group consisting of L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq), where g is an integer from 1 to 103, and each of Rl, Rm, Rn, Ro, Rp, and Rq is independently selected from the group consisting of R1 to R130; wherein L AB1 (R1)(R1)(R1)(R1)(R1) to L AB103 (R130)(R130)(R130)(R130)(R130) are each defined in the following List 3b:

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] In some embodiments, ligand L A is selected from the group consisting of L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'), where g' is an integer from 1 to 13, and each of Rl', Rm', Rn', Ro', Rp' and Rq' is independently selected from the group consisting of R1 to R130; Rq' is selected from E1 to E125 as defined herein; wherein L AC 1-(R1)(R1)(R1)(R1)(R1)(E1) to L AC 13-(R130)(R130)(R130)(R130)(R130)(E125) are each defined in the following Listing 3c:

[0284]

[0285]

[0286] In some embodiments, the compound has the formula M(L A ) p (L B ) q (L C ) r , where L B and L C are each bidentate ligands; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p + q + r is the oxidation state of metal M.

[0287] In some embodiments, L B comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, L B comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, L B comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, L B comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, L B comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0288] In some embodiments, L C comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, L C comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, LC comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, L C comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, L C comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0289] In some embodiments, the compound has a formula selected from the group consisting of: Ir(L A )3, Ir(L A )(L B )2, Ir(L A )2(L B ), Ir(L A )2(L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other.

[0290] In some embodiments, the compound may have the formula Ir(L A )3, the formula Ir(L A )(L Bk )2, the formula Ir(L A )2(L Bk ), the formula Ir(L A )2(L Cj-I ), the formula Ir(L A )2(L Cj-II ), the formula Ir(L A )(L Bk )(L Cj-I ), or the formula Ir(L A )(L Bk )(L Cj-II ), wherein L A is a ligand of formula I as defined herein; L Bk as defined herein; and L Cj-I and L Cj-II are each as defined herein.

[0291] In some embodiments, L B is selected from the group consisting of: substituted or unsubstituted phenylpyridine, substituted or unsubstituted phenylimidazole, and substituted or unsubstituted phenylbenzimidazole; and L C is a substituted or unsubstituted acetylacetonate.

[0292] In some embodiments, L Bis a substituted or unsubstituted phenylpyridine, and L C is a substituted or unsubstituted acetylacetonate.

[0293] In some embodiments, the compound has the formula Pt(L A )(L B ); and wherein L A and L B can be the same or different. In some embodiments, L A and L B are linked to form a tetradentate ligand.

[0294] In some embodiments, L B and L C are each independently selected from the group consisting of the structures of List 4 below:

[0295]

[0296]

[0297]

[0298] Wherein:

[0299] T is selected from the group consisting of: B, Al, Ga, and In;

[0300] K 1 ' is selected from the group consisting of: a single bond, O, S, NR e , PR e , BR e , CR e R f and SiR e R f ;

[0301] Y 1 to Y 13 each independently is selected from the group consisting of C and N;

[0302] Y' is selected from the group consisting of: BR e , BR e R f , NR e , PR e , P(O)R e , O, S, Se, C═O,

[0303] C═S, C═Se, C═NR e , C═CR e R f , S═O, SO2, CR e Rf , SiR e R f and GeR e R f ;

[0304] R e and R f may be fused or joined to form a ring;

[0305] Each R a , R b , R c and R d may independently represent mono-substituted to the maximum allowable number of substitutions or no substitution;

[0306] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

[0307] R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d any two substituents may be fused or joined to form a ring or form a multidentate ligand.

[0308] In some embodiments, L B and L C are each independently selected from the group consisting of the structures in List 5 below:

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] Wherein:

[0317] R a ', R b ', R c ', R d ' and R e ' each independently represents zero substitution, mono-substitution, or up to the maximum allowable number of substitutions on their respective rings;

[0318] R a1 , R b1 , R c1 , R a ', R b ', R c ', R d ' and R e ' each independently is hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

[0319] R a ', R b ', R c ', R d ', and R e ' two of the substituents can be fused or joined to form a ring or form a polydentate ligand.

[0320] In some embodiments, L B comprises a structure, where the variables are the same as previously defined. In some embodiments, Y 1 to Y 4 each independently is carbon. In some embodiments, at least one of Y 1 to Y 4 is N. In some embodiments, exactly one of Y 1 to Y 4 is N. In some embodiments, Y 1 is N. In some embodiments, Y 2 is N. In some embodiments, Y 3 is N. In some embodiments, Y 4 is N. In some embodiments, at least one R a is a tertiary alkyl, silyl, or germyl group. In some embodiments, at least one R a is a tertiary alkyl group. In some embodiments, Y 3 is C and the R a connected thereto is a tertiary alkyl, silyl, or germyl group. In some embodiments, Y 1 to Y 3 are C, Y 4 is N, and the R 3Linked R a is a tertiary alkyl group, a silyl group or a germyl group. In some embodiments, Y1 to Y3 are C, Y4 is N, and Ra 2 linked to Y is a tertiary alkyl group, a silyl group or a germyl group. In some embodiments, at least one R b is a tertiary alkyl group, a silyl group or a germyl group. In some embodiments, the tertiary alkyl group is a tert-butyl group. In some embodiments, at least one pair of R a , a pair of R b or a pair of R a and R b are joined or fused to form a ring.

[0321] In some embodiments, L A can be selected from L Ai , where i is an integer from 1 to 582; and L B can be selected from L Bk , where k is an integer from 1 to 530, where:

[0322] When the compound has the formula Ir(L Ai )3, the compound is selected from the group consisting of Ir(L A1 )3 to Ir(L A582 )3;

[0323] When the compound has the formula Ir(L Ai )(L Bk )2, the compound is selected from the group consisting of Ir(L A1 )(L B1 )2 to Ir(L A582 )(L B530 )2;

[0324] When the compound has the formula Ir(L Ai )2(L Bk ), the compound is selected from the group consisting of Ir(L A1 )2(L B1 ) to Ir(L A582 )2(L B530 );

[0325] When the compound has the formula Ir(L Ai )2(L Cj-I ), j is an integer from 1 to 1416, where the compound is selected from the group consisting of Ir(L A1 )2(L C1-I ) to Ir(L A582 )2(L C1416-I ); and

[0326] When the compound has the formula Ir(L Ai )2(LCj-II ) When j is an integer from 1 to 1416, where the compound is selected from the group consisting of Ir(L A1 )2(L C1-II ) to Ir(L A582 )2(L C1416-II );

[0327] Where each L Bk Has the structure defined in List 6 below:

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341] Where each L Cj-I Has a structure based on the formula ; And

[0342] Each L Cj-II Has a structure based on the formula , Where for each L Cj-I And L Cj-II In each L Cj , R 201 And R 202 Are defined in List 7 below:

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353] wherein R D1 to R D246 has the structure defined in List 8 below:

[0354]

[0355]

[0356]

[0357]

[0358] In some embodiments, the compound is selected from the group consisting of only those compounds corresponding to one of the following: L Bk 、L B1 、L B30 、L B31 、L B109 、L B110 、L B112 、L B113 、L B114 、L B125 、L B127 、L B138 、L B140 、L B149 、L B150 、L B170 、L B171 、L B172 、L B174 、L B208 、L B241 、L B312 、L B315 、L B356 、L B367 、LB371 , L B382 , L B439 , L B440 , L B455 , L B456 , L B457 , L B458 , L B461 , L B462 , L B463 , L B469 and L B476 .

[0359] In some embodiments, the compound is selected from the group consisting of only those compounds having L Bk corresponding to one of the following: L B1 , L B30 , L B31 , L B125 , L B138 , L B171 , L B172 , L B356 , L B357 , L B367 , L B371 , L B382 , L B455 and L B456 .

[0360] In some embodiments, the compound is selected from the group consisting of only those compounds having an L Cj-I or L Cj-II ligand, wherein the corresponding R 201 and R 202 are defined as one of the following structures: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D18 , R D20 , R D22 , R D37 , R D40 , R D41 , R D42 , R D43 , R D48 , R D49 , R D50 , R D54 , R D55 , R D58 , R D59 , R D78 , R D79 , R D81 , R D87, R D88 , R D89 , R D93 , R D116 , R D117 , R D118 , R D119 , R D120 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D147 , R D149 , R D151 , R D154 , R D155 , R D161 , R D175 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 and R D246 .

[0361] In some embodiments, the compound is selected from the group consisting of only those compounds having ligand L Cj-I or L Cj-II : the corresponding R 201 and R 202 of said ligand are defined as being selected from one of the following structures: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D22 , R D43 , R D50 , R D78 , R D116 , R D118 , R D133 , R D134 , R D135 , RD136 , R D143 , R D144 , R D145 , R D146 , R D149 , R D151 , R D154 , R D155 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 and R D246 .

[0362] In some embodiments, the compound is selected only from the group consisting of those compounds having one of the structures of Listing 9 for the L Cj-I ligand:

[0363]

[0364] In some embodiments, the compound has a formula selected from the group consisting of Ir(L A )3, Ir(L A )2(L B ), Ir(L A )(L B )2, Ir(L A )2(L C ), and Ir(L A )(L B )(L C ). In some embodiments, L A is selected from the group consisting of the structures of Listing 1, Listing 2, Listing 2a, Listing 2b, Listing 2c, Listing 2d, Listing 3a, Listing 3b, Listing 3c, and Listing 3, L B is selected from the group consisting of the structures of Listing 4, Listing 5, and Listing 6(L Bk ), and L C is selected from the group consisting of the structures of L Cj-I and L Cj-II as defined herein.

[0365] In some embodiments, L A is selected from the group consisting of the structures of List 1, and L B is selected from the group consisting of L Bk 's structures. In some embodiments, L A is selected from the group consisting of the structures of List 2, and L B is selected from the group consisting of L Bk 's structures. In some embodiments, L A is selected from L of List 3 defined herein Ai , and L B is selected from the group consisting of L Bk 's structures, where k is an integer from 1 to 530. In some embodiments, L A is selected from L of List 3a defined herein A'i' -(R m )(R n )(R o )(R p )(R q ), and L B is selected from the group consisting of L Bk 's structures, where k is an integer from 1 to 530. In some embodiments, L A is selected from L of List 3b defined herein AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq), and L B is selected from the group consisting of L Bk 's structures, where k is an integer from 1 to 530. In some embodiments, L A is selected from L of List 3c defined herein AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'), and L B is selected from the group consisting of L Bk 's structures, where k is an integer from 1 to 530. In some embodiments, L A is selected from List 3, List 3a, List 3b or List 3c defined herein, and L C is selected from the group consisting of L Cj-I and L Cj-II 's structures, where j is an integer from 1 to 1416.

[0366] In some embodiments, the compound may have the formula Ir(L A1 )3 to Ir(L A582 )3 of compounds consisting of Ir(L Ai )3, consisting of Ir(L A1(R1)(R1)(R1)(R1)(R1))3 to Ir(L A111 (R130)(R130)(R130)(R130)(R130))3 of the compound of the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))3, the formula Ir(L A )(L Bk )2, the formula Ir(L A )2(L Bk ), the formula Ir(L Ai )(L B )2, the formula Ir(L Ai )2(L B ), from Ir(L A1 )(L B1 )2 to Ir(L A582 )(L B530 )2 of the compound of the formula Ir(L Ai )(L Bk ), from Ir(L A1 )2(L B1 ) to Ir(L A582 )2(L B530 ) of the compound of the formula Ir(L Ai )2(L Bk ), from Ir(L A1 (R1)(R1)(R1)(R1)(R1))(L B1 )2 to Ir(L A111 (R130)(R130)(R130)(R130)(R130))(L B530 )2 of the compound of the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))(L Bk ), from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L B530 ) of the compound of the formula Ir(L Ai' -(R m )(R n )(R o)(R p )(R q ))2(L Bk )、 from Ir(L A1 )2(L C1-I ) to Ir(L A582 )2(L C1416-I ) of the formula Ir(L Ai )2(L Cj-I )、 from Ir(L A1 )2(L C1-II ) to Ir(L A582 )2(L C1416-II ) of the formula Ir(L Ai )2(L Cj-II )、 from Ir(L A1 )(L B1 )(L C1-I ) to Ir(L A582 )(L B530 )(L C1416-I ) of the formula Ir(L Ai )(L Bk )(L Cj-I )、 from Ir(L A1 )(L B1 )(L C1-II ) to Ir(L A582 )(L B530 )(L C1416-II ) of the formula Ir(L Ai )(L Bk )(L Cj-II )、 from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L C1-I ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L C1416-I ) of the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))2(L Cj-I )、 from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L C1-II ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L C1416-II ) of the formula Ir(L Ai'-(R m )(R n )(R o )(R p )(R q ))2(L Cj-II ) and compounds from Ir(L A1 (R1)(R1)(R1)(R1)(R1))(L B1 )(L C1-I ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))(L B530 )(L C1416-I ) having the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))(L Bk )(L Cj-I ) or compounds from Ir(L A1 (R1)(R1)(R1)(R1)(R1))(L B1 )(L C1-II ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))(L B530 )(L C1416-II ) having the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))(L Bk )(L Cj-II ), where L Ai' -(R m )(R n )(R o )(R p )(R q ), L Ai , L Bk , L Cj-I and L Cj-II are all defined herein.

[0367] In some embodiments, the compound may have the formula Ir(L AB1 (R1)(R1)(R1)(R1)(R1))3 to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))3 of compoundsAB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))3, consisting of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))(L B1 )2 to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))(L B530 )2 of the compound of the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))(L Bk )2, consisting of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L B1 ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L B530 ) of the compound of the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Bk ), consisting of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L C1-I ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L C1416-I ) of the compound of the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Cj-I ), consisting of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L C1-II ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L C1416-II ) of the compound of the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Cj-II ), consisting of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))(L B1 )(L C1-I ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))(L B530 )(L C1416-I ) of the compound of the formula Ir(L ABg-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))(L Bk )(L Cj-I ) or consisting of compounds of Ir(L AB1 (R1)(R1)(R1)(R1)(R1))(L B1 )(L C1-II ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))(L B530 )(L C1416-II ) and consisting of compounds of the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))(L Bk )(L Cj-II ), where L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq), L Bk , L Cj-I and L Cj-II are all defined herein.

[0368] In some embodiments, the compound may have the formula Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))3 to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))3 and consisting of compounds of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))3, consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))(L B1 )2 to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))(L B530 )2 and consisting of compounds of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))(L Bk ), consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L B1 ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L B530 ) and consisting of compounds of the formula Ir(L ACg'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Bk )、 consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L C1-I ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L C1416-I ) of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Cj-I )、 consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L C1-II ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L C1416-II ) of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Cj-II )、 consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))(L B1 )(L C1-I ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))(L B530 )(L C1416-I ) of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))(L Bk )(L Cj-I ) or consisting of compounds of Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))(L B1 )(L C1-II ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))(L B530 )(L C1416-II ) of the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))(L Bk )(L Cj-II ), wherein LAC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'), L Bk , L Cj-I and L Cj-II are all defined herein.

[0369] In some embodiments, the compound is selected from the group consisting of the structures of Listing 10 below:

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441] On the other hand, the present disclosure provides a compound comprising a core structure selected from the group consisting of the structures of List 10a below:

[0442]

[0443]

[0444]

[0445]

[0446]

[0447] wherein Y 4 is independently C or N at each occurrence; and Y B1 and Y B2 each independently is 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, CR, CRR', SiRR' and GeRR'.

[0448] It should be understood that, as understood by those of ordinary skill in the art, each hydrogen in each structure in Listing 10a may be substituted.

[0449] In yet another aspect, the present disclosure further provides a first ligand L having the formula X A" of the compound: In formula X, Z 1 ' and Z 2 ' each independently is C or N;

[0450] Moiety A1 is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic and the polycyclic fused ring system is independently a 5 - to 10 - membered carbocyclic or heterocyclic ring;

[0451] Moiety C1 is a bicyclic fused ring system, wherein each ring of the bicyclic fused ring system is independently a 5 - to 10 - membered carbocyclic or heterocyclic ring;

[0452] Y D is 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, CR, CRR', SiRR' and GeRR';

[0453] R A1 、R B2 and R C1 each independently represents mono - substitution to the maximum allowable substitution or no substitution;

[0454] Each R, R', RA1 , R B2 and R C1 are independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boranyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;

[0455] Any two substituents may be joined or fused to form a ring;

[0456] L A" is coordinated to a metal M having an atomic mass of at least 40;

[0457] The metal M may be coordinated to other ligands; and

[0458] L A" may be joined to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0459] In some embodiments of Formula X, moiety A1 is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, the aza variants include one N on the benzo ring. In some embodiments, the aza variants include one N on the benzo ring and the N is bonded to the Ir atom. In some embodiments, moiety A1 is pyridine or benzimidazole. In some of these embodiments, pyridine is substituted with at least one deuterated alkyl or aryl group. In some of these embodiments, pyridine is substituted with at least one CD3. In some of these embodiments, pyridine is substituted with two CD3.

[0460] In some embodiments of Formula X, moiety C1 contains only one ring nitrogen. In some embodiments of Formula X, each ring of moiety C1 is independently a 6-membered ring. In some of these embodiments, the ring of moiety C1 fused to ring B1 is pyridine. In some of these embodiments, the ring of moiety C1 not fused to ring B1 is pyridine.

[0461] In some embodiments of Formula X, part of C1 is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole.

[0462] In some embodiments of Formula X, Y D is O.

[0463] In some embodiments, L A" comprises the structure of Formula Xa wherein R T is hydrogen, or a substituent selected from the group consisting of the general substituents defined herein. In some embodiments of Formula Xa, R T may have the structure of Formula Xb,

[0464] wherein R D1 represents mono-substituted to tri-substituted or unsubstituted;

[0465] wherein each R 1 ', R 2 ' and R D ' is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

[0466] wherein at least one of R 1 ' and R 2 ' is not hydrogen or deuterium.

[0467] In some embodiments of Formula Xb, neither R 1 ' nor R 2 ' is hydrogen or deuterium.

[0468] In some embodiments of Formula Xb, R 1 ' and R 2 ' are each independently selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl and combinations thereof.

[0469] In some embodiments of Formula Xb, R 1 ' and R 2 ' are the same. In some embodiments of Formula Xb, R 1 ' and R 2 ' are different.

[0470] In some embodiments of Formula Xb, R 1 ' and R 2Each of them in 'contains at least 3 carbon atoms. In some embodiments of formula Xb, R 1 ' and R 2 ' each contain at least 4 carbon atoms. In some embodiments of formula Xb, R 1 ' and R 2 ' each contain at least 5 carbon atoms. In some embodiments of formula Xb, R 1 ' and R 2 ' each contain an alkyl group. In some embodiments of formula Xb, R 1 ' and R 2 ' each contain an aryl group. In some embodiments of formula Xb, R 1 ' and R 2 ' are each independently isopropyl.

[0471] In some embodiments of formula Xb, at least one R D1 is not hydrogen or deuterium. In some embodiments of formula Xb, at least one R D1 is selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl, and combinations thereof.

[0472] In some embodiments of formula Xb, the meta R 1 ' and R 2 ' for both are selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl, and combinations thereof. In some embodiments of formula Xb, the meta R D1 ' for both R 1 ' and R 2 ' is an aryl group substituted with at least one germyl or silyl group. In some embodiments of formula Xb, the meta R D1 ' for both R 1 ' and R 2 ' is a phenyl group substituted with at least one germyl or silyl group. D1 is a phenyl group substituted with at least one germyl or silyl group.

[0473] In some embodiments of formula Xb, at least one R D1 has the structure of formula Xc ;

[0474] wherein R D2 represents mono-substituted to tri-substituted or unsubstituted; and

[0475] wherein each R 11 ', R 21 ' and R D2 is independently hydrogen, or a substituent selected from the group of general substituents defined herein.

[0476] In some embodiments of formula Xb, R1 ' and R 2 ' meta-R of both D1 Has a structure of formula Xc.

[0477] In some embodiments of formula Xc, R 11 ' or R 21 ' at least one of which is not hydrogen or deuterium. In some embodiments of formula Xc, R 11 ' and R 21 ' each independently selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl and combinations thereof. In some such embodiments, R 11 ' and R 21 ' are the same, while in other embodiments, R 11 ' and R 21 ' are different.

[0478] In some embodiments of formula Xc, R 11 ' and R 21 ' each is hydrogen or deuterium.

[0479] In some embodiments of formula Xc, at least one R D2 is not hydrogen or deuterium.

[0480] In some embodiments of formula Xc, at least one R D2 selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl and combinations thereof. In some embodiments of formula Xc, R 11 ' and R 21 ' meta-R of both D2 selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germyl and combinations thereof.

[0481] In some embodiments of formula Xc, R 11 ' and R 21 ' meta-R of both D2 selected from the group consisting of: aryl, alkyl, silyl, germyl and combinations thereof. In some embodiments of formula Xc, R 11 ' and R 21 ' meta-R of both D2 selected from the group consisting of: phenyl, tert-butyl, Si(Me)3, Si(Ph)3, Ge(Me)3, Ge(Ph)3 and combinations thereof. In some embodiments of formula Xc, R 11 ' and R 21 ' meta-R of both D2 is phenyl, tert-butyl, Si(Me)3, Si(Ph)3, Ge(Me)3 or Ge(Ph)3.

[0482] In some embodiments of Formula Xc, R 11 ' and R 21 ' at the meta position of both R D2 is phenyl. In some embodiments of Formula Xc, R 11 ' and R 21 ' at the meta position of both R D2 is tert-butyl. In some embodiments of Formula Xc, R 11 ' and R 21 ' at the meta position of both R D2 is Si(Me)3 or Si(Ph)3. In some embodiments of Formula Xc, R 11 ' and R 21 ' at the meta position of both R D2 is Ge(Me)3 or Ge(Ph)3.

[0483] In some embodiments of Formula Xa, two RA1s can be fused to form a ring. In some such embodiments, the ring can be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, or triazole. In some such embodiments, the ring can be benzene.

[0484] In some embodiments of L A" in Formula X or Formula Xa, L A" can be combined with all L B and / or L C as defined throughout this disclosure.

[0485] In some embodiments of Formula X, the compound is selected from the group consisting of the structures of List 10b below:

[0486]

[0487] In some embodiments, the compound has Formula II wherein:

[0488] M 1 is Pd or Pt;

[0489] Moiety E is a monocyclic or polycyclic structure, wherein each ring of the monocyclic or polycyclic fused-ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0490] Moiety F is a monocyclic, polycyclic fused-ring structure, or an acyclic moiety, wherein each ring of the monocyclic or polycyclic fused-ring structure is independently a 5- to 10-membered carbocyclic or heterocyclic ring; and wherein the acyclic moiety is 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, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, cycloalkylene, and combinations thereof;

[0491] Z 3 and Z 4 are each independently C or N;

[0492] K, K 3 and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of the K, K 3 and K 4 are direct bonds;

[0493] L 1 、L 2 and L 3 are each independently absent or selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR', S═O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof, wherein at least one of L 1 and L 2 is present;

[0494] R E and R F each independently represent zero substitution, mono-substitution, or up to the maximum allowable number of substitutions;

[0495] R, R', R E and R F each independently is hydrogen or a substituent selected from the group of general substituents defined herein; and

[0496] two adjacent R A 、R B 、R C 、R E and R F may be joined or fused together to form a ring.

[0497] In some embodiments, R, R', R E and R FEach independently is hydrogen or a substituent selected from the group consisting of preferred general substituents.

[0498] In some embodiments, portions E and F are each independently a monocyclic or polycyclic structure, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- or 6-membered carbocyclic or heterocyclic ring.

[0499] In some embodiments of Formula II, at least one R 1 , R 2 , R 3 , R E or R F is a substituent selected from the group consisting of general substituents defined herein. In some embodiments, at least one R 1 is a substituent selected from the group consisting of general substituents defined herein. In some embodiments, at least one R 2 is a substituent selected from the group consisting of general substituents defined herein. In some embodiments, at least one R 3 is a substituent selected from the group consisting of general substituents defined herein. In some embodiments, at least one R E is a substituent selected from the group consisting of general substituents defined herein. In some embodiments, at least one R F is a substituent selected from the group consisting of general substituents defined herein.

[0500] In some embodiments of Formula II, at least one R, R', R 1 , R 2 , R 3 , R E or R F is partially or fully deuterated. In some embodiments, at least one R 1 is partially or fully deuterated. In some embodiments, at least one R 2 is partially or fully deuterated. In some embodiments, at least one R 3 is partially or fully deuterated. In some embodiments, at least one R E is partially or fully deuterated. In some embodiments, at least one R F is partially or fully deuterated. In some embodiments of Formula II, R or R', if present, is partially or fully deuterated.

[0501] In some embodiments of Formula II, at least one R, R', R 1 , R 2 , R 3 , R E or R Fis or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one of R, R', R 1 、R 2 、R 3 、R E or R F is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one of R, R', R 1 、R 2 、R 3 、R E or R F is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one of R, R', R 1 、R 2 、R 3 、R E or R F is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one of R, R', R 1 、R 2 、R 3 、R E or R F is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0502] In some embodiments of Formula II, at least one R 1 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 1 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0503] In some embodiments of Formula II, at least one R 2 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 2is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 2 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0504] In some embodiments of Formula II, at least one R 3 is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 3 is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0505] In some embodiments of Formula II, at least one R E is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R E is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R E is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R E is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R E is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0506] In some embodiments of Formula II, at least one R F is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R F is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R F is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R F is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R F is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0507] In some embodiments of Formula II, at least one R or R' is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R or R' is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0508] In some embodiments, Formula II comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, Formula II comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, Formula II comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, Formula II comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, Formula II comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0509] In some embodiments of Formula II, both moiety E and moiety F are 6-membered aromatic rings.

[0510] In some embodiments of Formula II, moiety F is a 5- or 6-membered heteroaromatic ring.

[0511] In some embodiments of Formula II, L 1 is O or CRR'.

[0512] In some embodiments of Formula II, Z 4 is N and Z 3 is C. In some embodiments of Formula II, Z 4 is C and Z 3 is N.

[0513] In some embodiments of Formula II, L 2 is a direct bond. In some embodiments of Formula II, L 2 is NR.

[0514] In some embodiments of Formula II, K 1 、K 2 、K 3 and K 4 are all direct bonds. In some embodiments of Formula II, one of K 1 、K 2 、K 3 and K 4 is O.

[0515] In some embodiments of Formula III, the compound is selected from the group consisting of compounds of the formula having Pt(L A' )(Ly):

[0516]

[0517] wherein L A' is selected from the group consisting of the structures of List 11 below:

[0518]

[0519]

[0520]

[0521] wherein each of X1 to X 20 is independently C or N;

[0522] the remaining variables are the same as previously defined; and two substituents may be joined or fused to form a ring. wherein L y is selected from the group consisting of the structures of List 12 below:

[0523]

[0524]

[0525]

[0526]

[0527] wherein each R, R', R X and R Y is independently hydrogen, or a substituent selected from the group of general substituents defined herein.

[0528] the remaining variables are the same as previously defined; and

[0529] any two substituents may be joined or fused to form a ring.

[0530] In some embodiments of Formula III, the compound is selected from the group consisting of compounds of the formula having Pt(L A' )(Ly):

[0531]

[0532] wherein L A' is selected from the group consisting of the structures defined in List 13 below:

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540] wherein L y is selected from the group consisting of the structures of List 14 below:

[0541]

[0542]

[0543]

[0544]

[0545]

[0546] wherein R K , R L , R M , Rs, Rt and Ru are each independently selected from R1 to R444 as defined below:

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566] In some embodiments, the compound is selected from the group consisting of the structures of the following Listing 15:

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582] In some embodiments, a compound having a first ligand L comprising the structure of Formula I described herein A may be 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, the percentage of deuteration has its ordinary meaning and includes the percentage of all possible hydrogen atoms (e.g., positions of hydrogen or deuterium) in the compound that are occupied by deuterium atoms. In some embodiments, the carbon atoms contained in the ring coordinated to metal M are fully or partially deuterated. In some embodiments, the carbon atoms contained in the polycyclic system coordinated to metal M are fully or partially deuterated. In some embodiments, the substituents attached to the monocyclic or fused polycyclic system coordinated to metal M are fully or partially deuterated.

[0583] In some embodiments, the emission of the compound of Formula I at room temperature has a full width at half maximum (FWHM) equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.

[0584] In some embodiments of the heteroleptic compound having the formula M(L A ) p (L B ) q (L C ) r , the ligand L A has a first substituent R I , wherein the first atom a-I in the first substituent R I is the farthest from the metal M among all the atoms of the ligand L A . Additionally, the ligand L B (if present) has a second substituent R II , wherein the first atom a-II in the second substituent R II is the farthest from the metal M among all the atoms of the ligand L B . Further, the ligand L C (if present) has a third substituent R III , wherein the first atom a-III in the third substituent R III is the farthest from the metal M among all the atoms of the ligand L C .

[0585] In such heteroleptic compounds, vectors V D1 , V D2 and V D3 can be defined as follows. V D1 represents the direction from the metal M to the first atom a-I, and the vector VD1 The value D 1 represents the straight-line distance between the metal M and the first atom a-I in the first substituent R I . V D2 represents the direction from the metal M to the first atom a-II, and the vector V D2 The value D 2 represents the straight-line distance between the metal M and the first atom a-II in the second substituent R II . V D3 represents the direction from the metal M to the first atom a-III, and the vector V D3 The value D 3 represents the straight-line distance between the metal M and the first atom a-III in the third substituent R III .

[0586] In such heteroleptic compounds, a sphere having a radius r is defined, the center of which is the metal M and the radius r is the minimum radius that allows the sphere to enclose all the atoms that are not part of the substituents R I , R II and R III ; and wherein D 1 , D 2 and D 3 is at least one of which is at least larger than the radius r by In some embodiments, D 1 , D 2 and D 3 is at least one of which is at least larger than the radius r by 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6 or In some embodiments, D 1 , D 2 and D 3 is at least two of which are at least larger than the radius r by 1.5, 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6 or

[0587] In some embodiments of such heteroleptic compounds, the compound has a transition dipole moment axis, and the angles between the transition dipole moment axis and the vectors V D1 , V D2 and V D3 are determined, wherein the transition dipole moment axis and the vectors V D1 , V D2 and V D3 is at least one of the angles less than 40°. In some embodiments, the transition dipole moment axis and the vectors V D1 , V D2 and V D3At least one of the angles between is less than 30°, 20°, 15°, or 10°. In some embodiments, the transition dipole moment axis and the vector V D1 , V D2 and V D3 At least two of the angles between are less than 20°. In some embodiments, the transition dipole moment axis and the vector V D1 , V D2 and V D3 At least two of the angles between are less than 15° or 10°.

[0588] In some embodiments, the transition dipole moment axis and the vector V D1 , V D2 and V D3 All three of the angles between are less than 20°. In some embodiments, the transition dipole moment axis and the vector V D1 , V D2 and V D3 All three of the angles between are less than 15° or 10°.

[0589] In some embodiments of such heteroleptic compounds, the compound has a vertical dipole ratio (VDR) of 0.33 or less. In some embodiments of such heteroleptic compounds, the compound has a VDR of 0.30, 0.25, 0.20, or 0.15 or less.

[0590] One of ordinary skill in the art will readily understand the meaning of the terms the transition dipole moment axis of a compound and the vertical dipole ratio of a compound. However, the meanings of these terms can be found in U.S. Patent No. 10,672,997, the disclosure of which is incorporated herein by reference in its entirety. In U.S. Patent No. 10,672,997, the horizontal dipole ratio (HDR) of a compound is discussed rather than the VDR. However, one of ordinary skill in the art will readily understand that VDR = 1 - HDR.

[0591] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emission via phosphorescence, fluorescence, thermally activated delayed fluorescence, triplet-triplet annihilation, or a combination of these methods. In some embodiments, the emissive dopant can be a racemic mixture or can be enriched in one enantiomer. In some embodiments, the compounds of the present invention can have different stereoisomers, such as fac and mer. The present compounds relate to individual isomers and mixtures of various isomers in any mixing ratio. In some embodiments, the compound can be homoleptic (each ligand being the same). In some embodiments, the compound can be heteroleptic (at least one ligand being different from the others). In some embodiments, when there is more than one ligand coordinated to the metal, the ligands can all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, each ligand can be different from all the other ligands. This also holds in embodiments where the ligands coordinated to the metal can be linked to other ligands coordinated to the metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, in cases where the coordinating ligands are linked together, in some embodiments, all the ligands can be the same, and in some other embodiments, at least one of the linked ligands can be different from the other ligands.

[0592] In yet another aspect of the present disclosure, a formulation comprising a novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of solvents, emitters, hosts, hole injection materials, hole transport materials, electron blocking materials, hole blocking materials, and electron transport materials disclosed herein.

[0593] This disclosure encompasses any chemical structure that includes the novel compounds of this disclosure or their monovalent or multivalent variants. In other words, the inventive compounds or their monovalent or multivalent variants can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of: monomers, polymers, macromolecules, and supramolecules (also referred to as supermolecules). As used herein, a "monovalent variant of a compound" refers to the same portion of the compound, but where one hydrogen has been removed and replaced with a bond that attaches to the remainder of the chemical structure. As used herein, a "multivalent variant of a compound" refers to the same portion of the compound, but where more than one hydrogen has been removed and replaced with one or more bonds that attach to the remainder of the chemical structure. In the case of a supramolecule, the inventive compounds can also be incorporated into a supramolecular complex without covalent bonds. As used in this context, the description that structure A contains portion B means that structure A includes the structure of portion B, and the structure of portion B does not include H or D atoms that can be attached to portion B. This is because at least one H or D on a given portion structure must be replaced with a substituent such that portion B can be part of structure A, and after it becomes part of structure A, one or more of the H or D on the given portion B structure can be further substituted.

[0594] C. OLEDs and Devices of the Present Disclosure

[0595] In another aspect, the present disclosure also provides an OLED device that includes a first organic layer containing a compound as disclosed in the above compound portion of the present disclosure.

[0596] In some embodiments, the OLED includes: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a compound having a first ligand L A and the first ligand L A includes the structure of Formula I as described herein.

[0597] In some embodiments, the organic layer is selected from the group consisting of: HIL, HTL, EBL, EML, HBL, ETL, and EIL. In some embodiments, the organic layer can be an emissive layer and the compound as described herein can be an emissive dopant or a non-emissive dopant.

[0598] In some embodiments, the organic layer can further include a host, where the host includes at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-borazinonaphtho[3,2,1-de]anthracene, azaborane, oxaborabine, dihydroacridine, xanthene, dihydrobenzoazasiline, dibenzooxasiline, phenoxazine, phenoxathiol, phenothiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrol, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, silane, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0599] In some embodiments, the subject can be selected from the group consisting of the following structures in subject group 1:

[0600]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606] in:

[0607] Each of J1 to J6 is independently C or N;

[0608] L' is a direct bond or an organic linking group;

[0609] Each Y AA , Y BB , Y CC and Y DD independently selected from the group consisting of: absence of bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0610] R A '、R B '、R C '、R D '、R E '、R F ' and RG each independently represents mono-substituted, up to maximum substitution or unsubstituted;

[0611] each R, R', R A ', R B ', R C ', R D ', R E ', R F ' and R G ' are independently hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring;

[0612] and, where possible, each unsubstituted aromatic carbon atom is optionally replaced by N to form a nitrogen-substituted ring.

[0613] In some embodiments, at least one of J1 to J3 is N. In some embodiments, at least two of J1 to J3 are N. In some embodiments, all three of J1 to J3 are N. In some embodiments, each Y CC and Y DD are independently O, S or SiRR', or more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen heterocycle.

[0614] In some embodiments, the host is selected from the group consisting of: EG1-MG1-EG1 to EG53-MG27-EG53 having the formula EGa-MGb-EGc, or EG1-EG1 to EG53-EG53 having the formula EGa-EGc when MGb is absent, where a is an integer from 1 to 53, b is an integer from 1 to 27, and c is an integer from 1 to 53. The structures of EG1 to EG53 are shown below:

[0615]

[0616]

[0617] The structures of MG1 to MG27 are shown below:

[0618]

[0619] In some embodiments, the host can be any one of its nitrogen-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the host has a formula selected from the group of hosts h1 to h112.

[0620]

[0621]

[0622] In some embodiments, the organic layer may further comprise a host, wherein the host comprises a metal complex.

[0623] In some embodiments, the emissive layer may comprise two hosts: a first host and a second host. In some embodiments, the first host is a hole-transporting host and the second host is an electron-transporting host. In some embodiments, the first host is a hole-transporting host and the second host is a bipolar host. In some embodiments, the first host is an electron-transporting host and the second host is a bipolar host. In some embodiments, the first host and the second host may form an exciplex. In some embodiments, the emissive layer may comprise a third host. In some embodiments, the third host is selected from the group consisting of: an insulating host (wide-bandgap host), a hole-transporting host, and an electron-transporting host. In some embodiments, the third host forms an exciplex with one of the first host and the second host or with both the first host and the second host. In some embodiments, the emissive layer may comprise a fourth host. In some embodiments, the fourth host is selected from the group consisting of: an insulating host (wide-bandgap host), a hole-transporting host, and an electron-transporting host. In some embodiments, the fourth host forms an exciplex with one of the first host, the second host, and the third host, with two of the first host, the second host, and the third host, or with each of the first host, the second host, and the third host. In some embodiments, the LUMO of the electron-transporting host is less than -2.4 eV, less than -2.5 eV, less than -2.6 eV, or less than -2.7 eV. In some embodiments, the HOMO of the hole-transporting host is higher than -5.6 eV, higher than -5.5 eV, higher than -5.4 eV, or higher than -5.35 eV. The HOMO and LUMO values can be determined electrochemically in solution. Cyclic voltammetry and differential pulse voltammetry in solution can be carried out using a CH Instruments Model 6201B potentiostat, using anhydrous dimethylformamide (DMF) solvent and tetrabutylammonium hexafluorophosphate as a supporting electrolyte. Glassy carbon, platinum wire, and silver wire are used as the working electrode, counter electrode, and reference electrode, respectively. By measuring the peak potential difference by differential pulse voltammetry, the electrochemical potential can be referenced to an internal ferrocene-ferrocenium redox pair (Fc / Fc+).According to the literature ((a) Fink R., Heischkel Y., Thelakkat M., Schmidt H.-W., Chem. Mater. 1998, 10, 3620-3625; (b) Pommerehne J., Vestweber H., Guss W., Mahrt R.F., Bassler H., Porsch M., Daub, J. Adv. Mater. 1995, 7, 551), the corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies are determined by referring the cationic and anionic redox potentials to the ferrocene reference (4.8 eV vs. vacuum).

[0624] In some embodiments, the compounds as described herein can be a sensitizer or a component of a sensitizer; wherein the device can further comprise a receptor that receives energy from the sensitizer. In some embodiments, the receptor is an emitter in the device. In some embodiments, the receptor can be a fluorescent material. In some embodiments, the compounds as described herein can be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain a receptor in the form of one or more non-delayed fluorescence and / or delayed fluorescence materials. In some embodiments, the compounds as described herein can be used as a component of an exciplex that functions as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the receptor and the receptor will emit energy or further transfer the energy to a final emitter. The receptor concentration can range from 0.001% to 99.9%. The receptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the receptor is a thermally activated delayed fluorescence (TADF) material. In some embodiments, the receptor is a non-delayed fluorescence material. In some embodiments, the emission can be generated by any one or all of the sensitizer, the receptor, and the final emitter. In some embodiments, the emission of the receptor at room temperature has a full width at half maximum (FWHM) equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.

[0625] As used herein, phosphorescence generally refers to photon emission when there is a change in the electron spin quantum number, i.e., the initial and final states of the emission have different electron spin quantum numbers, such as from the T1 to the S0 state. Most of the Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, if the exciplex formation involves a triplet emitter, such exciplexes can also emit phosphorescence. On the other hand, a fluorescent emitter generally refers to photon emission when the electron spin quantum number remains unchanged, such as from the S1 to the S0 state, or from the D1 to the D0 state. A fluorescent emitter can be a delayed fluorescence or non-delayed fluorescence emitter. Depending on the spin state, a fluorescent emitter can be a singlet emitter or a doublet emitter or other multiplet emitters. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the thermal population between the triplet and the singlet excited state. Thermal energy can activate the triplet transition back to the singlet. This type of delayed fluorescence is also referred to as TADF. E-type delayed fluorescence characteristics can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that TADF emission requires a compound or exciplex with a small singlet-triplet energy gap (ΔE S-T ) less than or equal to 400, 350, 300, 250, 200, 150, 100, or 50 meV. There are two main types of TADF emitters, one called donor-acceptor type TADF and the other called multi-resonant (MR) TADF. Generally, a single compound donor-acceptor TADF compound is constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) and an electron acceptor moiety (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). A donor-acceptor exciplex can be formed between a hole-transporting compound and an electron-transporting compound. Examples of MR-TADF materials include highly conjugated fused ring systems. In some embodiments, the MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials can also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 for delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, such time can be greater than 10 microseconds and less than 100 microseconds.

[0626] In some embodiments, the OLED can include additional compounds selected from the group consisting of: non-delayed fluorescent materials, delayed fluorescent materials, phosphorescent materials, and combinations thereof.

[0627] In some embodiments, the inventive compounds described herein are phosphorescent materials.

[0628] In some embodiments, the phosphorescent material is an emitter that emits light within the OLED. In some embodiments, the phosphorescent material does not emit light within the OLED. In some embodiments, the phosphorescent material transfers its excited state energy to another material within the OLED. In some embodiments, the phosphorescent material participates in charge transport within the OLED. In some embodiments, the phosphorescent material is a sensitizer or a component of a sensitizer, and the OLED further includes a receptor. In some embodiments, the phosphorescent material forms an exciplex with another material (e.g., a host material, an emitter material) within the OLED.

[0629] In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material is an emitter that emits light within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material does not emit light within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material transfers its excited state energy to another material within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material participates in charge transport within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material is a receptor, and the OLED further includes a sensitizer.

[0630] In some embodiments of the OLED, the delayed fluorescent material includes at least one donor group and at least one receptor group. In some embodiments, the delayed fluorescent material is a metal complex. In some embodiments, the delayed fluorescent material is a non-metal complex. In some embodiments, the delayed fluorescent material is a Pt, Pd, Zn, Cu, Ag, or Au complex (some of which are also referred to as metal-assisted (MA) TADF). In some embodiments, the metal-assisted delayed fluorescent material includes a metal-carbene bond. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material includes at least one chemical group selected from the group consisting of: aryl-amine, aryloxy, arylthio, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, 5λ 2 ,9λ 2 -diazaboranaphtho[2,3,4-de]anthracene, 5-oxa-9λ 2-aza-13b-boraphenanthro[3,2,1-de]anthracene, azacyclohexaborane, oxaborole, dihydroacridine, xanthene, dihydrobenzazasilole, dibenzooxasilole, phenoxazine, phenoxathiin, phenothiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, amino, silyl, their aza variants, and combinations thereof. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material comprises tris(aryl / heteroaryl)borane, wherein one or more pairs of substituents from the aryl / heteroaryl are joined to form a ring. In some embodiments, the fluorescent material comprises at least one chemical group selected from the group consisting of naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene.

[0631] In yet another aspect, the OLEDs of the present disclosure may further comprise an emissive region containing a compound or a formulation of compounds as disclosed in the above compound portions of the present disclosure. In some embodiments, the emissive region may comprise a compound having a first ligand L A or a formulation containing such a compound, the first ligand L A comprising the structure of Formula I as described herein.

[0632] In some embodiments, the emissive region consists of one or more organic layers, wherein at least one of the one or more organic layers has a minimum thickness selected from the group consisting of 350, 400, 450, 500, 550, 600, 650, and In some embodiments, at least one of the one or more organic layers is formed of an emissive system having a figure of merit (FOM) equal to or greater than a value selected from the group consisting of 2.50, 2.55, 2.60, 2.65, 2.70, 2.75, 2.80, 2.85, 2.90, 2.95, 3.00, 5.00, 10.0, 15.0, and 20.0. The definition of FOM can be obtained in U.S. Patent Application Publication No. 2023 / 0292605, the entire content of which is incorporated herein by reference. In some embodiments, at least one of the one or more organic layers comprises a compound or a formulation of compounds as disclosed in Part A and Part D of the present disclosure.

[0633] In some embodiments, the OLEDs or emissive regions containing the compounds of the present invention disclosed herein can be incorporated into a full-color pixel arrangement of a device. The full-color pixel arrangement of such a device includes at least one pixel, wherein the at least one pixel includes a first sub-pixel and a second sub-pixel. The first sub-pixel includes a first OLED, and the first OLED includes a first emissive region. The second sub-pixel includes a second OLED, and the second OLED includes a second emissive region. In some embodiments, the first and / or second OLEDs, the first and / or second emissive regions can be the same or different and each can independently have various device features and various embodiments of the compounds of the present invention included therein, as well as various combinations and sub-combinations of various device features and various embodiments of the compounds of the present invention included therein, as disclosed herein.

[0634] In some embodiments, the first emissive region is configured to emit light having a peak wavelength λ max1 ; the second emissive region is configured to emit light having a peak wavelength λ max2 . In some embodiments, the difference between the peak wavelength λ max1 and λ max2 is at least 4 nm but within the same color. For example, light of light blue and dark blue as described above. In some embodiments, the first emissive region is configured to emit light having a peak wavelength λ max1 in a region of the visible spectrum of 400 - 500 nm, 500 - 600 nm, 600 - 700 nm; and the second emissive region is configured to emit light having a peak wavelength λ max2 in one of the remaining regions of the visible spectrum of 400 - 500 nm, 500 - 600 nm, 600 - 700 nm. In some embodiments, the first emissive region includes (if more than one) a first number of emissive layers deposited one above the other; and the second emissive region includes (if more than one) a second number of emissive layers deposited one above the other; and the first number is different from the second number. In some embodiments, both the first emissive region and the second emissive region include phosphorescent materials that can be the same or different. In some embodiments, the first emissive region includes a phosphorescent material, while the second emissive region includes a fluorescent material. In some embodiments, both the first emissive region and the second emissive region include fluorescent materials that can be the same or different.

[0635] In some embodiments, at least one pixel of the OLED or emission region includes a total of N sub-pixels; wherein the N sub-pixels include a first sub-pixel and a second sub-pixel; wherein each of the N sub-pixels includes an emission region; and wherein the total number of emission regions within at least one pixel is equal to or less than N-1. In some embodiments, the second emission region is identical to the first emission region; and each sub-pixel of at least one pixel includes one emission region identical to the first emission region. In some embodiments, the full-color pixel arrangement may have a plurality of pixels including a first pixel region and a second pixel region; wherein at least one display characteristic of the first pixel region is different from the corresponding display characteristic of the second pixel region, and wherein at least one display characteristic is selected from the group consisting of: resolution, cavity mode, color, out-coupling, and color filter.

[0636] In some embodiments, the OLED is a stacked OLED including one or more charge generation layers (CGLs). In some embodiments, the OLED includes a first electrode, a first emission region disposed above the first electrode, a first CGL disposed above the first emission region, a second emission region disposed above the first CGL, and a second electrode disposed above the second emission region. In some embodiments, the first emission region and / or the second emission region may have various device characteristics as described above for the pixelated device. In some embodiments, the stacked OLED is configured to emit white. In some embodiments, one or more of the emission regions in the pixelated OLED or the stacked OLED include a sensitizer and a receptor having various sensitization device characteristics and various embodiments of the inventive compounds disclosed herein. For example, the first emission region is included in the sensitization device while the second emission region is not included in the sensitization device; in some cases, both the first emission region and the second emission region are included in the sensitization device.

[0637] In some embodiments, the OLED can emit at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99%, or 100% of the light from the plasmon mode. In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emission layer serves as an enhancement layer. The enhancement layer comprises a plasmonic material that exhibits surface plasmon resonance, the plasmonic material being non-radiatively coupled to the emitter material and transferring the excited state energy from the emitter material to the non-radiative mode of the surface plasmon polaritons. In some embodiments, the enhancement layer is disposed at a distance not exceeding a threshold distance from the organic emission layer, where, due to the presence of the enhancement layer, the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant. The threshold distance is the position where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. Another threshold distance is the distance at which the total radiative decay rate constant divided by the sum of the total non-radiative decay rate constant and the total radiative decay rate constant is equal to the photoluminescence yield of the emitter material in the absence of the enhancement layer.

[0638] In some embodiments, the OLED further comprises an out-coupling layer. In some embodiments, the out-coupling layer is disposed on the side opposite to the organic emission layer above the enhancement layer. The out-coupling layer scatters the energy from the surface plasmon polaritons. In some embodiments, this energy is scattered as photons into free space. In other embodiments, the energy is scattered from the surface plasmon mode of the device into other modes, such as but not limited to organic waveguide mode, substrate mode, or another waveguide mode. In some embodiments, one or more intermediate layers can be disposed between the enhancement layer and the out-coupling layer. Examples of the intermediate layer can be dielectric materials, including organic, inorganic, perovskite, oxides, and can include stacks and / or mixtures of these materials.

[0639] The enhancement layer changes the effective properties of the medium in which the emitter material resides, thereby causing any one or all of the following: reduced emissivity, changed emission line shape, angular variation of emission intensity, changed emitter material stability, changed OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, anode side, or both sides, or placing the enhancement layer itself as a CGL results in an OLED device that utilizes any of the above effects. In addition to the specific functional layers described in the various OLED examples mentioned herein and shown in the figures, the OLEDs according to the present disclosure may further include any other functional layers common in OLEDs.

[0640] In some embodiments, the enhancement layer may comprise a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. In some embodiments, the plasmonic material includes at least one metal. In such embodiments, the metal may include at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, or Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has features of wavelength size arranged periodically, quasi-periodically, or randomly, or features of sub-wavelength size arranged periodically, quasi-periodically, or randomly.

[0641] In some embodiments, the outer coupling layer has features of wavelength size or sub-wavelength size arranged periodically, quasi-periodically, or randomly. In some embodiments, the outer coupling layer may be composed of a plurality of nanoparticles. In some embodiments, the outer coupling layer is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the outer coupling layer can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer, or changing the material of the enhancement layer. The plurality of nanoparticles of the device can be formed from at least one of the following: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stack or layer of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outer coupling layer is composed of at least metal nanoparticles, where 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, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the outer coupling layer is formed by lithography.

[0642] In some embodiments of the plasmonic device, the emitter and / or host compound used in the emission layer has a vertical dipole ratio (VDR) of 0.33 or greater. In some such embodiments, the emitter and / or host compound has a VDR of 0.40, 0.50, 0.60, 0.70, or greater.

[0643] In yet another aspect, the present disclosure also provides a consumer product that includes an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, where the organic layer may include a compound or a formulation of compounds as disclosed in the above compound portion of the present disclosure.

[0644] In some embodiments, a consumer product includes an OLED having an anode; a cathode; and an organic layer disposed between the anode and the cathode, where the organic layer can include Technical Solution 1 as described herein.

[0645] Generally, an OLED includes 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. The injected holes and electrons each migrate toward the electrode of opposite charge. When an electron and a hole are located on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. When the exciton relaxes through a light-emission mechanism, light is emitted. In some cases, the exciton can be localized as an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, can also occur but are generally considered undesirable.

[0646] Figure 1 An organic light-emitting device 100 is shown. The figure is not necessarily drawn to scale. Device 100 can include a substrate 110, an anode 115, a hole injection layer (HIL) 120, a hole transport layer (HTL) 125, an electron blocking layer (EBL) 130, an emission layer (EML) 135, a hole blocking layer (HBL) 140, an electron transport layer (ETL) 145, an electron injection layer (EIL) 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by depositing the layers in sequence. The properties and functions of these various layers and example materials are described in more detail in columns 6-10 of US 7,279,704, which is incorporated by reference.

[0647] Additional instances of each of these layers can be obtained. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of light-emitting and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin layer of metal (such as Mg:Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0648] Figure 2 Displays 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. The device 200 can be fabricated by depositing the layers in sequence. Since the most common OLED configuration has a cathode disposed above the anode, and the device 200 has a cathode 215 disposed below the anode 230, the device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to the device 100 can be used in the corresponding layers of the device 200. Figure 2 Provides an example of how some layers can be omitted from the structure of the device 100.

[0649] Figure 1 and 2The simple layered structure described is provided by way of non-limiting example, and it should be understood that embodiments of the present disclosure may be used in conjunction with a 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 obtained by combining the various layers described in different ways, or the layers may be omitted altogether 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 the various layers as including a single material, it should be understood that combinations of materials may be used, such as a mixture of a host and a dopant, or more generally, mixtures. Additionally, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, the hole transport layer 225 transports holes and injects holes into the 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 such as, for example, as described with respect to Figure 1 and 2 the different organic materials described.

[0650] Structures and materials not specifically described may also be used, such as OLEDs (PLEDs) incorporating polymeric materials, as disclosed, for example, in U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. By way of another example, an OLED having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. The OLED structure may deviate from Figure 1 and 2 the simple layered structure described. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the mesa structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the dimpled structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0651] Unless otherwise specified, any one of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet (as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (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 known as organic vapor jet deposition (OVJD)) (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 other layers, preferred methods include thermal evaporation, sputtering, chemical vapor deposition, atomic layer deposition, and electron beam deposition. Preferred patterning methods include deposition through a mask, photolithography, and cold welding (as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety) and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods can also be used. The materials to be deposited can be modified to make them suitable for the specific deposition method. For example, branched or unbranched substituents, preferably containing at least 3 carbons, such as alkyl and aryl groups, can be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 or more carbons can be used, and a range of 3 to 20 carbons is preferred. Materials having an asymmetric structure can have better solution processability than materials having a symmetric structure because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents can be used to enhance the ability of small molecules to withstand solution processing.

[0652] Devices fabricated in accordance with embodiments of the present disclosure may further optionally include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage by harmful substances in an environment exposed to, including moisture, vapor, and / or gas, etc. The barrier layer may be deposited over the substrate, over the electrodes, under the substrate, under the electrodes, or beside the substrate, electrodes, or over any other part of the device (including the edges). The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic compounds or organic compounds or both. Preferred barrier layers include multiple alternative layers of the following materials: polymeric materials and non-polymeric materials; organic materials and inorganic materials; or mixtures of polymeric materials and non-polymeric materials, an example of which is described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entirety.

[0653] Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units), which can in turn 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) that can be utilized by end-user product manufacturers. The electronic component module can optionally include driving electronics and / or a power source. 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 electronic component modules (or units) incorporated therein. Disclosed is a consumer product that includes an OLED that includes a compound of the present disclosure in an organic layer of the OLED. The consumer product should include any kind of product that includes one or more light sources and / or one or more of certain types of visual displays. Some examples of the consumer product include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays (displays with a diagonal less than 2 inches), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls that include a plurality of displays tiled together, theater or stadium screens, light therapy devices, and signage. A variety of control mechanisms can be used to control the devices fabricated in accordance with the present disclosure, including passive matrix and active matrix. It is intended that many of the devices be used in a temperature range that is comfortable for humans, such as from 18 °C to 30 °C, and more preferably at room temperature (20 - 25 °C), but they can be used outside of this temperature range (e.g., from -40 °C to +80 °C).

[0654] More details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0655] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can employ the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0656] In some embodiments, the OLED has one or more characteristics selected from the group consisting of flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further includes a layer comprising carbon nanotubes. In some embodiments, the OLED further includes one or more quantum dots. Such quantum dots may be in the emission layer or in other functional layers, such as a down-conversion layer.

[0657] In some embodiments, the OLED includes an RGB pixel arrangement or a white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel with a diagonal less than 10 inches or an area less than 50 square inches. In some embodiments, the OLED is a display panel with a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0658] Other materials used in D.OLED

[0659] The materials described herein are various examples of specific layers that can be used in an OLED. It can also be used in combination with a wide variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used by themselves in the emissive dopants in the EML or in combination with a wide variety of other emitters, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds and devices disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0660] a) Conductive dopants:

[0661] The charge transport layer can be doped with a conductive dopant to generally change its charge carrier density, which in turn will change its conductivity. 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 can also be achieved. The hole transport layer can be doped with a p-type conductive dopant, and an n-type conductive dopant is used in the electron transport layer. In some embodiments, the conductive dopant includes at least one chemical moiety selected from the group consisting of cyano, fluorinated aryl or heteroaryl, fluorinated alkyl or cycloalkyl, alkylene, heteroaryl, amide, benzodithiophene, and highly conjugated heteroaryl extended by acyclic double bonds.

[0662] b) HIL / HTL:

[0663] The hole injection / transport materials used in the present disclosure are not particularly limited, and any compound can be used as long as the compound is commonly used as a hole injection / transport material. Examples of the materials include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorohydrocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x ; p-type semi-conductive organic compounds such as 1,4,5,8,9,12-hexaazatriphenylenehexanitrile; metal complexes; and crosslinkable compounds.

[0664] Examples of aromatic amine derivatives for HIL or HTL include (but are not limited to) the following general structures:

[0665]

[0666] Ar 1 to Ar 9 Each of which is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, fluorene, phenanthrene, fluorene, pyrene, 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, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units, which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Ar 1 to Ar 9 Each of which may be unsubstituted or may be substituted with a general substituent as described above, and any two substituents may be joined or fused into a ring.

[0667] In some embodiments, each Ar 1 to Ar 9 independently contains a moiety selected from the group consisting of:

[0668]

[0669] where k is an integer from 1 to 20; X 101 to X 108 is C or N; Z 101 is C, N, O, or S.

[0670] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0671]

[0672] where Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, and the coordinating atoms of Y 101 and Y 102 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0673] In some embodiments, (Y 101 -Y 102 ) is 2-phenylpyridine or a 2-phenylimidazole derivative. In some embodiments, (Y 101 -Y 102 ) is a carbene ligand. In some embodiments, Met is selected from Ir, Pt, Pd, Os, Cu, and Zn. In some embodiments, the metal complex has a minimum oxidation potential in solution of less than about 0.6 V compared to the Fc + / Fc couple.

[0674] In some embodiments, the HIL / HTL material is selected from the group consisting of: phthalocyanine and porphyrin compounds, starburst triarylamine, CF x fluorohydrocarbon polymers, conductive polymers (e.g., PEDOT:PSS, polyaniline, polythiophene), phosphonic acids and silane SAMs, triarylamines or polythiophene polymers containing conductive dopants, organic compounds containing conductive inorganic compounds (such as molybdenum oxide and tungsten oxide), n-type semiconducting organic complexes, organometallic metal complexes, crosslinkable compounds, polythiophene-based polymers and copolymers, triarylamines, triarylamines containing a spirofluorene core, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indolocarbazole, isoindole compounds, and metal carbene complexes.

[0675] c) EBL:

[0676] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Additionally, a blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or higher triplet energy compared to one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO level of the compound used in the EBL is shallower than the HOMO levels of one or more of the hosts in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional group as one of the hosts described below.

[0677] d) Host:

[0678] The light-emitting layer of the organic EL device of the present disclosure preferably contains at least a light-emitting material as a dopant and a host material. Examples of the host material are not particularly limited, and any metal complex or organic compound can be used as long as the host does not completely quench the emission of the dopant.

[0679] Examples of metal complexes used as hosts preferably have the following general formula:

[0680]

[0681] where Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, and the coordinating atoms of Y 103 and Y 104 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be connected to the metal; and k'+k" is the maximum number of ligands that can be connected to the metal.

[0682] In some embodiments, the metal complex is:

[0683]

[0684] where (O-N) is a bidentate ligand having a metal coordinated to O and N atoms.

[0685] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0686] In some embodiments, the host compound contains at least one selected from the following groups: the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, 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, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-carbazole, aza-indolocarbazole, aza-triphenylene, aza-tetraphenylene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-borata-naphtho[3,2,1-de]anthracene; and the group consisting of 2 to 10 cyclic structural units, which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each option within each group may be unsubstituted or may be substituted with a general substituent as described herein or may be further fused.

[0687] In some embodiments, the host compound comprises at least one selected from the moieties consisting of:

[0688]

[0689] where k is an integer from 0 to 20 or from 1 to 20. X 101 to X 108 are independently selected from C or N. Z 101 and Z 102 are independently selected from C, N, O, or S.

[0690] In some embodiments, the host material is selected from the group consisting of arylcarbazole, metal 8-hydroxyquinolinates (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic fused rings, zinc complexes, based on Compounds, aryltriptycene compounds, polycondensed heteroaryl compounds, donor-acceptor type molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., pvk), spirofluorene compounds, spirofluorene-carbazole compounds, indolocarbazole, 5-membered ring electron-deficient heterocycles (e.g., triazole, oxadiazole), perylene complexes, metal phenoxypyridine compounds, metal coordination complexes (e.g., Zn, Al containing N^N ligands), dibenzothiophene / dibenzofuran-carbazole compounds, silicon / germanium aryl compounds, aryl benzoyl esters, carbazole linked by non-conjugated groups, azacarbazole / dibenzofuran / dibenzothiophene compounds, and high triplet metal organometallic complexes (e.g., metal-carbene complexes).

[0691] e) Emitter materials in the EML:

[0692] One or more emitter materials can be used in combination with the compounds or devices of the present disclosure. The emitter materials can be emissive or non-emissive in the current devices as described herein. Examples of emitter materials are not particularly limited, and any compound can be used as long as the compound can produce emission in a conventional OLED device. Examples of suitable emitter materials include, but are not limited to, compounds capable of producing emission via phosphorescence, non-delayed fluorescence, delayed fluorescence (especially thermally activated delayed fluorescence, i.e., TADF (also known as E-type delayed fluorescence)), triplet-triplet annihilation, or a combination of these methods.

[0693] In some embodiments, the emitter material has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0694] where L 1 , L 2 and L 3 can be the same or different;

[0695] where x is 1, 2, or 3;

[0696] where y is 0, 1, or 2;

[0697] where z is 0, 1, or 2;

[0698] where x + y + z is the oxidation state of the metal M;

[0699] where L 1 is selected from the group consisting of structures in the following ligand list:

[0700]

[0701]

[0702] Wherein each L 2 and L 3 is independently selected from the group consisting of and the structures in the ligand list; wherein:

[0703] M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag, and Cu;

[0704] T is selected from the group consisting of: B, Al, Ga, and In;

[0705] K 1 ' is a direct bond or is selected from the group consisting of NR e 、PR e 、O, S, and Se;

[0706] Each Y 1 to Y 15 is independently selected from the group consisting of carbon and nitrogen;

[0707] Y' is selected from the group consisting of BR e 、NR e 、PR e 、O, S, Se, C=O, S=O, SO2, CR e R f 、SiR e R f and GeR e R f ;

[0708] Each R a 、R b 、R c and R d can independently represent mono-substitution to the maximum possible number of substitutions, or no substitution;

[0709] Each R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e and R f is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

[0710] wherein any two substituents can be fused or joined to form a ring or form a polydentate ligand.

[0711] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 1:

[0712]

[0713]

[0714]

[0715] wherein

[0716] each X 96 to X 99 is independently C or N;

[0717] each Y 100 is independently selected from the group consisting of NR", O, S, and Se;

[0718] each R 10a , R 20a , R 30a , R 40a and R 50a represents mono-substituted, up to maximally substituted, or unsubstituted;

[0719] each of R, R', R", R 10a , R 11a , R 12a , R 13a , R 20a , R 30a , R 40a , R 50a , R 60 , R 70 , R 97 , R 98 and R 99 is independently hydrogen or a substituent selected from the group of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0720] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 2:

[0721]

[0722]

[0723]

[0724]

[0725]

[0726] Wherein:

[0727] Each Y 100 is independently selected from the group consisting of NR″, O, S, and Se;

[0728] L is independently selected from the group consisting of: a direct bond, BR″, BR″R″′, NR″, PR″, O, S, Se, C═O, C═S, C═Se, C═NR″, C═CR″R″′, S═O, SO2, CR″, CR″R″′, SiR″R″′, GeR″R″′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

[0729] X 100 and X 200 each occurrence is selected from the group consisting of O, S, Se, NR″, and CR″R″′;

[0730] Each R A" 、R B" 、R C" 、R D" 、R E" and R F" independently represents mono-substituted, up to maximum-substituted, or unsubstituted;

[0731] R, R′, R″, R″′, R A1 ′, R A2 ′, R A" 、R B" 、R C" 、R D" 、R E" 、R F" 、R G" 、R H" 、R I" 、R J" 、R K" 、R L" 、R M" and R N" each independently is hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0732] In some embodiments of the above dopant groups 1 and 2, each unsubstituted aromatic carbon atom may be replaced by N to form a heterocyclic ring. In some embodiments, the maximum number of N atoms in one ring is 1 or 2. In some embodiments of the above dopant group 2, each Pt atom in the formula may be replaced by a Pd atom.

[0733] In some embodiments of the OLED, the delayed fluorescence material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescence material is a metal complex. In some embodiments, the delayed fluorescence material is a non-metal complex. In some embodiments, the delayed fluorescence material is a Zn, Cu, Ag or Au complex.

[0734] In some embodiments of the OLED, the delayed fluorescence material has the formula M(L 5 )(L 6 ), where M is Cu, Ag or Au, and L 5 and L 6 are different, and L 5 and L 6 are independently selected from the group consisting of:

[0735]

[0736] where A 1 –A 9 are each independently selected from C or N;

[0737] Each R P , R Q and R U independently represents mono-substituted, up to maximum-substituted or unsubstituted;

[0738] where each R P , R P , R U , R SA , R SB , R RA , R RB , R RC , R RD , R RE and R RF is independently hydrogen or a substituent selected from the group of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0739] In some embodiments of the OLED, the delayed fluorescence material comprises at least one of the donor moieties selected from the group consisting of:

[0740]

[0741] where Y T , Y U , Y V and Y W are each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO2.

[0742] In some of the above embodiments, any carbon ring atom up to a total of at most three carbon ring atoms in each benzene ring of any of the above structures, together with its substituents, can be replaced by N.

[0743] In some embodiments, the delayed fluorescence material comprises at least one of acceptor moieties selected from the group consisting of: nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor moiety and the donor moiety as described herein can be directly connected, connected via a conjugated linking group or a non-conjugated linking group (such as sp 3 carbon or silicon atoms).

[0744] In some embodiments, the fluorescent material comprises at least one of chemical moieties selected from the group consisting of:

[0745]

[0746]

[0747] wherein Y F 、Y G 、Y H and Y I are each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C═O, S═O, and SO2;

[0748] wherein X F and X G are each independently selected from the group consisting of C and N.

[0749] In some of the above embodiments, any carbon ring atom up to a total of at most three carbon ring atoms in each benzene ring of any of the above structures, together with its substituents, can be replaced by N.

[0750] f) HBL:

[0751] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Additionally, a blocking layer can be used to confine emission to the desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and / or a higher triplet energy compared to one or more of the emitters closest to the HBL interface.

[0752] In some embodiments, the compounds used in the HBL contain the same molecules or the same functional groups as those used in the host described above.

[0753] In some embodiments, the compounds used in the HBL include at least one of the following moieties selected from the group consisting of:

[0754]

[0755] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0756] g) ETL:

[0757] The electron transport layer (ETL) may include materials capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound can be used as long as it is commonly used to transport electrons.

[0758] In some embodiments, the compounds used in the ETL contain at least one of the following moieties in the molecule:

[0759] and fullerenes; where k is an integer from 1 to 20, X 101 to X 108 is selected from C or N; Z 101 is selected from the group consisting of C, N, O, and S.

[0760] In some embodiments, the metal complexes used in the ETL contain, but are not limited to, the following general formula:

[0761]

[0762] where (O-N) or (N-N) is a bidentate ligand having a metal coordinated to the atoms O, N, or N,N; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be connected to the metal.

[0763] In some embodiments, the ETL materials are selected from the group consisting of: anthracene-benzimidazole compounds, azatriphenylene derivatives, anthracene-benzothiazole compounds, metal 8-hydroxyquinolinates, metal hydroxybenzoquinolinates, bathocuprine compounds, 5-membered ring electron-deficient heterocycles (e.g., triazole, oxadiazole, imidazole, benzimidazole), silole compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0764] h) Charge generation layer (CGL)

[0765] In a tandem or stacked OLED, the CGL plays a fundamental role in performance and is composed of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and the electrodes. The electrons and holes consumed in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include the n- and p-conductive dopants used in the transport layer.

[0766] In any of the compounds disclosed herein, the hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99% and 100%. As used herein, the deuteration percentage has its ordinary meaning and includes the percentage of all possible hydrogen and deuterium atoms replaced by deuterium atoms. In some embodiments, the deuterium atoms are attached to an aromatic ring. In some embodiments, the deuterium atoms are attached to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atoms are attached to a heteroatom, such as a Si or Ge atom.

[0767] It should be 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 replaced by other materials and structures without departing from the spirit of the invention. The invention as claimed may thus include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories as to why the invention works are not intended to be limiting.

[0768] E. Experimental data

[0769] Synthesis of Compound 1 of the present invention

[0770]

[0771]

[0772] Charge a 1.0 L conical flask with 2,6-dichloro-5-fluoropyridin-3-amine (9.000 g, 1 Eq, 49.73 mmol), diiodomethane (29.97 g, 9.00 mL, 2.25 Eq, 111.9 mmol) and DCM (135.6 mL) and stir. Add sodium nitrite (18.01 g, 5.25 Eq, 261.1 mmol) and water (90.41 mL), and vigorously stir the two-phase mixture. Add glacial acetic acid (61.36 g, 58.4 mL, 20.55 Eq, 1.022 mol) dropwise over 20 minutes, and stir the resulting mixture for 1 hour. Neutralize the mixture with aqueous NaOH and NaHCO₃. Separate the layers, and extract the aqueous layer with DCM. Wash the combined organics with brine, dry over Na₂S₂O₄, filter, and concentrate on a rotary evaporator to give the desired product 1 (7.76 g, 54% yield).

[0773] Charge a 250 mL 2-neck round-bottom flask with 1 (7.760 g, 1 Eq, 26.59 mmol), (2-hydroxyphenyl)boronic acid (3.851 g, 1.05 Eq, 27.92 mmol), [1,1'-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (866.4 mg, 0.05 Eq, 1.329 mmol), potassium carbonate (16.93 g, 3 Eq, 79.76 mmol), toluene (75.96 mL) and water (30.39 mL), and bubble N₂ through the mixture for 15 minutes. Then heat the reaction to 45 °C overnight, at which point its conversion is 85%. Heat the reaction for another 4 hours, then cool to room temperature. Dilute the mixture with 200 mL of 1:1 ethyl acetate / water and separate the layers. Extract the aqueous layer twice with 100 mL of ethyl acetate each time. Wash the combined organics with brine, dry over Na₂SO₄, filter and concentrate on a rotary evaporator. Coat the crude mixture onto Celite (diatomaceous earth), and elute through a silica gel column with 20% ethyl acetate / heptane. Concentrate the product fractions to a off-white solid 2 (5.76 g, 84%).

[0774] Charge a 250 mL round-bottom flask with 2 (5.758 g, 1 Eq, 22.31 mmol) and MeCN (51.89 mL) and stir rapidly. Add potassium carbonate (9.250 g, 3 Eq, 66.94 mmol) and heat the mixture to 70 °C overnight. Then cool the mixture to room temperature, and the product precipitates as an off-white solid. Stir the solid in 100 mL of water, filter and dry to give 3 (2.2 g, 44% yield).

[0775] Charge 3 (1.036 g, 1 Eq, 4.675 mmol), (3-formyl-2-methoxyphenyl)boronic acid (1.262 g, 1.5 Eq, 7.012 mmol), potassium phosphate (2.977 g, 3 Eq, 14.02 mmol), 1,4-dioxane (38.96 mL), and water (7.791 mL) into a 100 mL Schlenk flask, and bubble N2 through the mixture for 10 minutes. Add XPhos Pd G2 (367.8 mg, 0.1 Eq, 467.5 μmol) and heat the reaction to 90 °C overnight. Cool the reaction to room temperature, dilute with 100 mL of 1:1 ethyl acetate / water and separate the layers. Extract the aqueous layer with 100 mL of ethyl acetate twice, wash the combined organics with brine, dry over Na2SO4, filter, and concentrate on a rotary evaporator. Coat the crude material onto silica gel and elute through a silica gel column with 25% ethyl acetate / heptane. Concentrate the product fraction, at which point the product precipitates out of the solution. Filter and dry the white solid to give 4 (1.2 g, 80%).

[0776] Charge 4 (867 mg, 1.075 Eq, 2.70 mmol), N1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)benzene-1,2-diamine (0.865 g, 1 Eq, 2.51 mmol), sodium metabisulfite (865 mg, 3.311 Eq, 8.31 mmol), and DMF (32.6 mL) into a 100 mL round-bottom flask, and heat to 130 °C for 24 hours, then cool to room temperature. Pour the mixture into 125 mL of water and filter the resulting precipitate, dissolve in ethyl acetate, wash with aqueous lithium chloride solution, dry over Na2SO4, filter, and concentrate the filtrate on a rotary evaporator. Purify the crude material on a silica gel column with 10-30% ethyl acetate / heptane and concentrate the product fraction to give 5 (1.27 g, 78%).

[0777] Charge 5 (2.063 g, 1 Eq, 3.195 mmol) and DCM (31.95 mL) into a 100 mL round-bottom flask, and stir under N2 while cooling to -78 °C. Slowly add boron tribromide (4.002 g, 15.97 mL, 1.000 molarity, 5 Eq, 15.97 mmol) in hexane, and allow the mixture to reach room temperature overnight. Pour the reaction onto 100 g of ice and stir, then neutralize with aqueous NaHCO3. Separate the layers, and extract the aqueous layer with 50 mL of DCM. Wash the combined organics with brine, dry over Na2SO4, filter, and concentrate the filtrate on a rotary evaporator to give 6 (2.02 g, 99%).

[0778] Charge 6 (2.220 g, 1 Eq, 3.514 mmol), potassium carbonate (2.185 g, 4.5 Eq, 15.81 mmol), and N-methyl-2-pyrrolidone (18.99 mL) into a 250 mL round-bottom flask to reach 250 mL RBF, and heat to 145 °C overnight under N2, then cool to room temperature. Pour the mixture into 100 mL of water, filter the resulting precipitate, dissolve it in ethyl acetate, wash with aqueous lithium chloride solution, dry over Na2SO4, filter, and concentrate the filtrate on a rotary evaporator. Purify the crude material on a silica gel column with 10% ethyl acetate / heptane and concentrate the product fraction on a rotary evaporator. Grind the resulting residue with ethyl acetate / heptane, filter and dry the resulting solid to obtain 7 (0.92 g, 43%).

[0779]

[0780] Charge 8 (0.400 g, 1 Eq, 483 μmol), 7 (281 mg, 0.95 Eq, 459 μmol), 2,6-dimethylpyridine (106 mg, 115 μL, 2.05 Eq, 990 μmol), and 2-ethoxyethanol (16.1 mL) into a 50 mL Schlenk tube. Bubble N2 through the mixture and heat the reaction to 110 °C for 24 h, at which point the temperature is raised to 125 °C for an additional 24 h. Cool the reaction to room temperature and concentrate to half volume on a rotary evaporator. Add water (20 mL), and filter and dry the resulting yellow precipitate. Purify the crude solid on a silica gel column with 70 - 95% toluene / heptane. Concentrate the product fraction and grind the residue with DCM / methanol. Filter and dry the resulting solid to obtain Compound 1 of the present invention (0.25 g, 41%).

[0781] Synthesis of Compound 2 of the present invention

[0782]

[0783] 3-(2,6-dichloro-5-fluoropyridin-3-yl)-2-methoxybenzaldehyde (9)

[0784] A solution of potassium carbonate (7.19 g, 52.0 mmol, 3.0 equiv) in water (25 mL) was added to a solution of (3-formyl-2-methoxyphenyl)boronic acid (3.12 g, 17.34 mmol, 1.0 equiv) and 3-bromo-2,6-dichloro-5-fluoropyridine (4.67 g, 19.07 mmol, 1.1 equiv) in 1,4-dioxane (149 mL), and the mixture was bubbled with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.00 g, 0.867 mmol, 0.05 equiv) was added with continuous bubbling for an additional 5 minutes, and the mixture was heated at 85 °C overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (100 mL) and water (50 mL). The layers were separated, and the aqueous layer was washed with dichloromethane (3 × 20 mL). The combined organic layers were concentrated to a volume of about 10 mL and adsorbed onto silica gel (30 g), loaded onto a 100 g flash column, and purified on an Interchim (3 × 220 g Sorbtech silica gel columns, stacked) eluting with a gradient of 10% to 60% dichloromethane / hexane to give 9 (3.3 g, 59% yield) as an off-white solid.

[0785] 3-(2,6-Dichloro-5-fluoropyridin-3-yl)-2-hydroxybenzaldehyde (10)

[0786] At 0 °C, a 1.0 M solution of boron tribromide in dichloromethane (38.0 mL, 38.0 mmol, 2.0 equiv) was added to a solution of 1 (5.70 g, 19.0 mmol, 1.0 equiv) in dichloromethane (190 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (200 mL) and saturated sodium bicarbonate solution (200 mL). The layers were separated, and the aqueous layer was washed with dichloromethane (3 × 50 mL). The combined organic layers were dried over sodium sulfate (40 g), filtered, and concentrated under reduced pressure. The residue was dissolved completely in dichloromethane (100 mL), then hexane (500 mL) was added. The mixture was then concentrated to a volume of about 100 mL. The resulting precipitate was filtered and washed with hexane (40 mL) to give 10 (4.60 g, 85% yield) as an orange solid.

[0787] 2-Chloro-3-fluorobenzo[f]chromene-8-carbaldehyde (11)

[0788] A mixture of 10 (4.50 g, 15.7 mmol, 1.0 equiv) and potassium carbonate (6.52 g, 47.2 mmol, 3.0 equiv) in N,N-dimethylformamide (157 mL) was bubbled with nitrogen for 5 minutes and heated at 100 °C overnight. LC / MS analysis showed complete consumption of the starting material, giving the desired product. The reaction mixture was cooled to room temperature and water (300 mL) was added, resulting in precipitation. The precipitate was filtered and washed with water (100 mL). This filtrate was saved as Filtrate A. The solid was dissolved in dichloromethane (200 mL), transferred to a separatory funnel and the residual water was separated. The organic layer was concentrated to a volume of about 20 mL. Hexane (200 mL) was added, giving a precipitate which was filtered and washed with hexane (100 mL) to afford 11 (2.4 g) as a brown solid. The filtrate was saved as Filtrate B. The aqueous layer (Filtrate A) above was extracted with dichloromethane (3 × 100 mL). The combined organic layers were combined with Filtrate B and concentrated to a volume of about 10 mL. Hexane (100 mL) was added, giving a precipitate which was filtered and washed with hexane (20 mL) to afford 11 (0.6 g) as a brown solid, which was combined with the above batch to give 11 (3.0 g, 76% yield). It was used in the next step without further purification.

[0789] 3-Fluoro-2-(2-hydroxyphenyl)benzofuro[2,3-b]pyridine-8-carbaldehyde (12)

[0790] A solution of potassium carbonate (4.98 g, 36.1 mmol, 3.0 equiv) in water (17 mL) was added to a solution of (2-hydroxyphenyl)boronic acid (1.99 g, 14.4 mmol, 1.2 equiv) and 3 (3.00 g, 12.02 mmol, 1.0 equiv) in 1,4-dioxane (103 mL), and the mixture was bubbled with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.694 g, 0.601 mmol, 0.05 equiv) was added over 5 minutes with continuous bubbling, and the mixture was heated at 100 °C overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL) and water (100 mL). The layers were separated and the aqueous layer was washed with dichloromethane (3 × 100 mL). The combined organic layers were concentrated under reduced pressure and the residue was suspended in dichloromethane (20 mL). Hexane (150 mL) was added and the mixture was triturated at 40 °C for 1 hour and then filtered to afford 12 (2.0 g, 54% yield) as an off-white solid.

[0791] Bis(benzofuro)[2,3-b:2',3'-e]pyridine-4-carbaldehyde (13)

[0792] A mixture of 12 (1.90 g, 6.18 mmol, 1.0 equiv) and potassium carbonate (2.56 g, 18.6 mmol, 3.0 equiv) in N,N-dimethylformamide (62 mL) was bubbled with nitrogen for 5 minutes and heated at 110 °C overnight. LC / MS analysis showed complete consumption of the starting material, giving the desired product. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL) and water (100 mL). The layers were separated, and the aqueous layer was washed with dichloromethane (3 × 100 mL). The combined organic layers were passed through a pad of silica gel and diatomaceous earth and washed with dichloromethane (150 mL). The filtrate was concentrated to a volume of about 10 mL, and then hexane (100 mL) was added. The resulting precipitate was filtered to give 13 (1.19 g) as a yellow solid. The crude product was purified on an Interchim (80 g Sorbtech silica gel column) eluting with a gradient of 10 to 100% dichloromethane / hexane to give 13 (1.89 g, 99% yield).

[0793] 4-(1-(3,5-Diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)bis(benzofuro)[2,3-b:2',3'-e]pyridine (14)

[0794] A mixture of N1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)benzene-1,2-diamine (2.10 g, 6.10 mmol, 1.0 equiv), 13 (1.84 g, 6.40 mmol, 1.05 equiv) and sodium bisulfite (1.90 g, 18.3 mmol, 3.0 equiv) in N,N-dimethylacetamide (84 mL) was heated at 130 °C overnight. The mixture was cooled to room temperature, and sodium bisulfite (1.90 g, 18.3 mmol, 3.0 equiv) was added, and then it was heated at 130 °C overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (300 mL) and water (100 mL). The layers were separated, and the aqueous layer was washed with dichloromethane (3 × 100 mL). The combined organic layers were concentrated to a volume of about 80 mL, wet-loaded onto a 100 g loader column, and purified on an Interchim automated chromatography system (330 g and 220 g Sorbtech silica gel columns, stacked) eluting with a gradient of 5 to 100% dichloromethane / hexane and then with 5% ethyl acetate / 95% dichloromethane to give the desired product 14 (2.0 g) as a brown solid.

[0795] Synthesis of Compound 2 of the Invention

[0796] Charge a 50 mL Schlenk tube with 14 (0.973 g, 1 Eq, 1.59 mmol), an iridium complex (1.34 g, 1 Eq, 1.59 mmol), 2,6-dimethylpyridine (0.511 g, 3 Eq, 4.77 mmol) and 2-ethoxyethanol (25 mL). Bubble N2 through the mixture and heat the reaction to 110 °C for 24 h, at which point the temperature is raised to 125 °C for an additional 24 h. Cool the reaction to room temperature and concentrate to half volume on a rotary evaporator. Add water (20 mL) and filter and dry the resulting yellow precipitate. Purify the crude solid on a silica gel column with 70 - 95% toluene / heptane. Concentrate the product fractions and triturate the residue with DCM / methanol. Filter and dry the resulting solid to give Compound 2 of the present invention (1.25 g, 64%).

[0797] Synthesis of Compound 3 of the Present Invention

[0798]

[0799] Methyl 2-(3-bromo-2-hydroxyphenyl)acetate (16)

[0800] Charge a mixture of methyl 2-(2-hydroxyphenyl)acetate (17.3 g, 1 Eq, 103.9 mmol) and diisopropylamine (2.15 g, 3.00 mL, 0.205 Eq, 21.3 mmol) in DCM (200 mL) with NBS (21.0 g, 1.136 Eq, 118.0 mmol) portionwise (3 g every 15 min) at 0 °C and stir the mixture for 3 h. Then add water (200 mL) to the reaction mixture and separate the organic layer. Extract the aqueous layer with DCM (3 × 100 mL). Wash the combined organic layers with saturated aqueous NaHCO3 (200 mL), brine (200 mL), dry over sodium sulfate and concentrate under reduced pressure. Combine it with similarly prepared batches and purify by silica gel chromatography (330 g column, dry load with DCM, 0 - 30% EtOAc / isohexane) to give methyl 2-(3-bromo-2-hydroxyphenyl)acetate (30.47 g, 77 mmol, 58%) as a pale yellow liquid which solidifies on standing.

[0801] Methyl 2-(2-(benzyloxy)-3-bromophenyl)acetate (17)

[0802] A mixture of methyl 2-(3-bromo-2-hydroxyphenyl)acetate (30.5 g, 61 wt%, 1 Eq, 75.84 mmol), methyl 2-(3,5-dibromo-2-hydroxyphenyl)acetate (30.5 g, 38 wt%, 0.4712 Eq, 35.74 mmol) and K2CO3 (31.0 g, 2.958 Eq, 224.3 mmol) was suspended in DMF (150 mL). Benzyl bromide (28.8 g, 20.0 mL, 2.217 Eq, 168.1 mmol) was added and the mixture was stirred at room temperature overnight. Then water (800 mL) was added and the mixture was extracted with EtOAc (3 × 300 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (2 × 330 g (gold) columns, dry loading 0 - 30% EtOAc / isohexane) to give methyl 2-(2-(benzyloxy)-3-bromophenyl)acetate (24.8 g, 72 mmol, 96%) as a colorless oil.

[0803] 2-(2-(Benzyloxy)-3-bromophenyl)acetic acid (18)

[0804] To a solution of methyl 2-(2-(benzyloxy)-3-bromophenyl)acetate (24.8 g, 98 wt%, 1 Eq, 72.45 mmol) in THF (30.0 mL), methanol (15.0 mL) and water (15.0 mL) was added lithium hydroxide monohydrate (9.12 g, 2.999 Eq, 217.3 mmol). The reaction mixture was stirred at 40 °C for 90 minutes, cooled to room temperature and concentrated to remove volatiles. Water (100 mL) was added, then 1 M aqueous HCl was added to reach pH 3, and the product was then extracted with ethyl acetate (2 × 200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 2-(2-(benzyloxy)-3-bromophenyl)acetic acid (23.8 g, 73 mmol, 100%) as a white solid.

[0805] 2-(2-(Benzyloxy)-3-bromophenyl)-N-(naphthalen-1-yl)acetamide (19)

[0806] HATU (20.6 g, 1.2 Eq, 54.1 mmol) was added to a mixture of naphthalen-1-amine (6.45 g, 1 Eq, 45.0 mmol), 2-(2-(benzyloxy)-3-bromophenyl)acetic acid (16.2 g, 98 wt%, 1.1 Eq, 49.5 mmol), and DIPEA (12 g, 16 mL, 2.0 Eq, 92 mmol) in DCM (200 mL). The mixture was stirred at room temperature for 18 h, then diluted with water (700 mL) and stirred for 1 h. The solid was collected by filtration, washed with water (2 × 250 mL), and dried to give 2-(2-(benzyloxy)-3-bromophenyl)-N-(naphthalen-1-yl)acetamide (14.5 g, 32 mmol, 70%) as a light pink solid.

[0807] 3-(2-(Benzyloxy)-3-bromophenyl)-2-chlorobenzo[h]quinoline (20)

[0808] DMF (283 mg, 300 μL, 1.78 Eq, 3.87 mmol) was added to POCl3 (3.3 g, 2.0 mL, 9.9 Eq, 21 mmol) at 0 °C. After 5 min, 2-(2-(benzyloxy)-3-bromophenyl)-N-(naphthalen-1-yl)acetamide (1.00 g, 97 wt%, 1 Eq, 2.17 mmol) was added and the mixture was stirred at 70 °C for 2 h. The reaction mixture was cooled to 0 °C, quenched with water (20 mL), and extracted with EtOAc (3 × 20 mL). The combined organic fractions were washed with saturated aqueous NaHCO3 (2 × 30 mL). The organic layer was dried (MgSO4), filtered, combined with similarly prepared batches, and concentrated. The combined crude product was purified by silica gel chromatography (40 g column, dry loaded on silica, eluting with 0–5% EtOAc / isohexane) to give two fractions: 3-(2-(benzyloxy)-3-bromophenyl)-2-chlorobenzo[h]quinoline (725 mg, 1.4 mmol, 32%).

[0809] 2-Bromo-6-(2-chlorobenzo[h]quinolin-3-yl)phenol (21)

[0810] TFA (14.8 g, 10.0 mL, 29.52 Eq, 129.8 mmol) was added to 3-(2-(benzyloxy)-3-bromophenyl)-2-chlorobenzo[h]quinoline (2.13 g, 98 wt%, 1 Eq, 4.397 mmol). The mixture was stirred at 70 °C for 2 h, cooled to room temperature and concentrated under reduced pressure. The residue was basified with saturated aqueous NaHCO3 (pH = 8) and extracted with EtOAc (3 × 50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by silica gel chromatography (40 g column (gold), dry loading 0 - 15% EtOAc / isohexane) to give 2-bromo-6-(2-chlorobenzo[h]quinolin-3-yl)phenol as a viscous off-white solid (1.53 g, 3.7 mmol, 83%).

[0811] 1-Bromobenzo[h]benzofuro[2,3-b]quinoline (22)

[0812] A mixture of 2-bromo-6-(2-chlorobenzo[h]quinolin-3-yl)phenol (4.80 g, 90 wt%, 1 Eq, 11.23 mmol) and potassium carbonate (4.66 g, 3 Eq, 33.69 mmol) was stirred at 60 °C for 3 h. The reaction mixture was cooled to room temperature and precipitated with water (200 mL). The precipitate was collected by filtration, washed with water (2 × 20 mL) and dried in vacuo to give 11-bromobenzo[h]benzofuro[2,3-b]quinoline as a light brown solid (3.71 g, 10 mmol, 93%).

[0813] Benzo[h]benzofuro[2,3-b]quinoline-11-carbaldehyde (23)

[0814] At -75 °C, butyllithium (4.00 mL, 1.60 M, 1.516 Eq, 6.400 mmol) was added dropwise to a suspension of 11-bromobenzo[h]benzofuro[2,3-b]quinoline (1.50 g, 98 wt%, 1 Eq, 4.222 mmol) in THF (10.0 mL). The mixture was stirred for 10 min, then quenched with DMF (944 mg, 1.00 mL, 3.06 Eq, 12.9 mmol) and stirring was continued for 1 h. The cooling bath was then removed and the reaction mixture was warmed to room temperature and quenched with saturated aqueous NH4Cl (50 mL). It was combined with similarly prepared batches and extracted with a 2:1 mixture of EtOAc and THF (3 × 300 mL). The combined organics were dried over Na2SO4, filtered and concentrated to give benzo[h]benzofuro[2,3-b]quinoline-11-carbaldehyde as a yellow solid (2.21 g, 6.2 mmol, 88%).

[0815] 11-(1-(3,5-Diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[h]benzofuro[2,3-b]quinoline (24)

[0816] A mixture of benzo[h]benzofuro[2,3-b]quinoline-11-carbaldehyde (2.10 g, 83 wt%, 1 Eq, 5.863 mmol), N1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)benzene-1,2-diamine (2.15 g, 1.065 Eq, 6.241 mmol), sodium bisulfite (5.00 g, 8.197 Eq, 48.05 mmol) and sodium metabisulfite (9.00 g, 8.076 Eq, 47.35 mmol) in DMF (20.0 mL) was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature and precipitated with water (200 mL). The precipitate was filtered, washed with water (2 × 50 mL), dissolved in DCM (100 mL) and adsorbed onto silica. The crude product was purified by silica gel chromatography (40:5:1 DCM:EtOAc:Et3N) / isohexane]) to give 11-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[h]benzofuro[2,3-b]quinoline as an off-white solid (1.970 g, 3.159 mmol, 61%).

[0817] Synthesis of Compound 3 of the present invention

[0818] A 50 mL Schlenk tube was charged with 24 (0.8 g, 1 Eq, 1.29 mmol), an iridium complex (1.09 g, 1 Eq, 1.29 mmol), 2,6-dimethylpyridine (0.414 g, 3 Eq, 3.86 mmol) and 2-ethoxyethanol (25 mL). N2 was bubbled through the mixture and the reaction was heated to 110 °C for 24 h, at which point the temperature was raised to 125 °C for an additional 24 h. The reaction was cooled to room temperature and concentrated to half volume on a rotary evaporator. Water (20 mL) was added and the resulting yellow precipitate was filtered and dried. The crude solid was purified on a silica gel column with 70-95% toluene / heptane. The product fractions were concentrated and the residue was triturated with DCM / methanol. The resulting solid was filtered and dried to give Compound 3 of the present invention (63%).

[0819] Device examples

[0820] All example devices were fabricated by thermal evaporation under high vacuum (<10 -7 Torr). The anode is indium tin oxide (ITO). The cathode consists of Liq (lithium 8-hydroxyquinoline) and Composition of Al. All devices were encapsulated with epoxy-sealed glass covers immediately after fabrication in a nitrogen glove box (<1 ppm of H2O and O2), and a desiccant was incorporated inside the package. The organic stack of the device example consisted of the following in sequence from the ITO surface: LG101 (purchased from LG Chem) as the hole injection layer (HIL); HTM as the hole transport layer (HTL); with a thickness of the emission layer (EML); EBM as the electron blocking layer (EBL); an emission layer containing a 6:4 ratio of H-host (H1):E-host (H2) and 5 wt% of a green emitter; H2 as the hole blocking layer (HBL); doped with 35% of ETM Liq (lithium 8-hydroxyquinoline) as the ETL. The device structure is shown in Table 1. The chemical structures of the device materials are shown below.

[0821]

[0822]

[0823] Table 1. Device layer materials and thicknesses

[0824]

[0825] During fabrication, the devices were tested to measure EL and JVL. For this purpose, the samples were energized with a current density of 10 mA / cm 2 using a 2-channel Keysight B2902ASMU, and measurements were made with a Photo Research PR735 spectroradiometer. The radiance (W / str / cm 2 ) from 380 nm to 1080 nm and the total integrated photon count were collected. Then the devices were placed under a large-area silicon photodiode for JVL scanning. The integrated photon count of the devices at 10 mA / cm 2 was used to convert the photodiode current to a photon count. The voltage was scanned from 0 to the voltage equal to 200 mA / cm 2 . The EQE of the devices was calculated using the total integrated photon count. All device results are summarized in Table 2. The voltages, LEs, and EQEs of Invention Examples 1 and 2 were reported as relative numbers normalized to the results of Comparative Example 1; the voltages, LEs, and EQEs of Invention Example 3 were reported as relative numbers normalized to the results of Comparative Example 4.

[0826] Table 2 Device performance results

[0827]

[0828] *Definition of M / T: The M / T ratio is a descriptor of the "narrowness" of the peak of the emission peak, where M represents the area of the main peak, which is defined as the integral of the area with a wavelength of the maximum peak wavelength (λ max ) ± 15 nm, and T is the total area of the spectrum, which is defined as the integral of the entire spectrum. The higher the M / T, the narrower the peak.

[0829] **The voltages, LEs, and EQEs of Invention Examples 1 and 2 are reported as relative numbers normalized with respect to the results of Comparative Example 1. The voltages, LEs, and EQEs of Invention Example 3 are reported as relative numbers normalized with respect to the results of Comparative Example 2.

[0830] Compounds 1, 2, and 3 of the present invention exhibit higher luminescence efficiency (LE) and higher external quantum efficiency (EQE) than their comparative compounds. According to the above M / T data, Compounds 1 and 2 of the present invention exhibit spectra that are much narrower than those of Comparative Example 1. Similarly, Compound 3 of the present invention exhibits a spectrum that is much narrower than that of Comparative Example 2, as demonstrated by the M / T measurement results. The higher the M / T value, the narrower the spectrum. Generally, the M / T of phosphorescent emitter complexes is low, usually about 0.43, as shown in the comparative examples herein. Obtaining a higher M / T ratio has been a long - sought goal, and an increase of 0.01 in the M / T ratio is significant for achieving a narrow line shape. The narrower the line shape, the better the color purity of the display application. As background information, the ideal line shape is a single wavelength (single line). As can be seen here, compared with the comparative compounds, the compounds of the present invention having an additional nitrogen on the fused - ring system can significantly increase the M / T ratio number equal to or greater than 0.47. The improvement of these values is higher than the value attributable to experimental error, and the observed improvement is significant. The performance improvement observed in the above data is unexpected. All results show the importance of the compounds of the present invention in the application of organic light - emitting diodes (OLEDs).

Claims

1. A compound having a first ligand L comprising a structure of Formula I A : in: Z 1 , Z 2 and X 1 To X 4 Each of is independently C or N; The moiety A is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic and polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; The moiety C is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; K is selected from direct bond, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) Y is 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, CR, CRR', SiRR' and GeRR'; R 1 , R 2 and R 3 Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution; Each R, R', R α , R β , R 1 , R 2 and R 3 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; Any two substituents may be joined or fused to form a ring; One of the following statements is true: (1) The C part is a polycyclic fused ring system, and the ring B or the two R 2 The formed ring and the moiety C together contain at least two N ring atoms; (2) the moiety C comprises three or more fused 5- to 10-membered carbocyclic or heterocyclic rings, and the ring B and the moiety C together comprise at least one N ring atom; (3) Moiety A is a monocyclic 6-membered aromatic ring containing one or more N atoms, and moiety C is a fused bicyclic structure consisting of a 6-membered ring and a heterocyclic ring, wherein the 6-membered ring is fused to ring B1, and wherein ring B or moiety C contains at least one N atom; or at least one R 2 or R 3 contains an electron withdrawing group; or (4) The A portion is a monocyclic 6-membered aromatic ring containing one or more N atoms, the C portion is a monocyclic ring, and both R 2 joined to form moiety I, wherein moiety I is a heterocyclic ring or a heterocyclic fused ring system, wherein each ring of said heterocyclic ring and said heterocyclic fused ring system is independently a 5-membered or 6-membered carbocyclic ring or a heterocyclic ring; L A coordinated to a metal M having an atomic mass of at least 40; The metal M may be coordinated with other ligands; and L A can be joined to other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands, provided that if moiety C comprises two rings and the terminal ring comprises two N ring atoms, then moiety A is not imidazole; and provided that the compound is not one of the following:

2. The compound according to claim 1, wherein Z 1 is N and Z 2 is C, or Z 1 is carbene carbon and Z 2 is N, or Z 1 and Z 2 All C; and / or X 1 To X 4 Each of which is C or X 1 To X 4 At least one of them is N.

3. The compound of claim 1, wherein the moiety A is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbenes, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzene, oxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbenes derived from benzimidazole, aza-benzimidazole derived carbenes, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran and / or wherein the moiety C is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzo and selenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, aza-benzimidazole-derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene and aza-fluorene.

4. The compound according to claim 1, wherein ring B and moiety C together comprise only one ring N atom; and / or wherein ring B and moiety C together comprise at least two ring N atoms; and / or wherein moiety C comprises at least two ring N atoms; and / or wherein Y is selected from the group consisting of O, S, CRR', NR, SiRR' and Se; and / or wherein K is a direct bond, O or S; and / or wherein the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au and Cu; and / or wherein at least one R 1 comprising a substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and a combination thereof; and / or wherein at least one R 2 comprising a substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and a combination thereof; and / or wherein at least one R 3 Contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

5. The compound according to claim 1, wherein the ligand L A Select from the group consisting of: in: X1 to X 20 Each of is independently C or N; Y B1 and Y B2 each of which 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, CR, CRR', SiRR' and GeRR'; R A , R B and R C Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution; Each R, R', R A , R B , R C and R N are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; Any two substituents may be joined or fused to form a ring.

6. The compound according to claim 1, wherein the ligand L A Select from the group consisting of: in X1 to X 14 Each of is independently C or N; Y B1 and Y B2 each of which 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, CR, CRR', SiRR' and GeRR'; R A , R B and R C Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution; Each R, R', R A , R B , R C and R N are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; Any two substituents may be joined or fused to form a ring.

7. The compound according to claim 1, wherein the ligand L A Selected from L Ai , where i is an integer from 1 to 546, and L A1 To L A546 Each of them is defined as follows: The ligand L A Choose from L Ai' -(Rm)(Rn)(Ro)(Rp)(Rq), wherein i' is an integer from 1 to 111, and each of Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R130; wherein L A1 (R1)(R1)(R1)(R1)(R1) to L A111 Each of (R130)(R130)(R130)(R130)(R130) is defined as follows: or The ligand L A Choose from L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq), wherein g is an integer from 1 to 103, and each of Rl, Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R130; wherein L AB1 (R1)(R1)(R1)(R1)(R1) to L AB103 Each of (R130)(R130)(R130)(R130)(R130) is defined as follows: or The ligand L A Choose from L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'), wherein g' is an integer from 1 to 13, each of Rl', Rm', Rn', Ro', Rp' and Rq' is independently selected from the group consisting of R1 to R130; Rq' is selected from E1 to E125; wherein L AC 1-(R1)(R1)(R1)(R1)(R1)(E1) to L AC Each of 13-(R130)(R130)(R130)(R130)(R130)(E125) is defined as follows: Where R1 to R130 have the following structure: Where E1 to E125 have the following structure defined in the EWG2 manifest:

8. The compound according to claim 1, wherein the compound has M(L A ) p (L B ) q (L C ) r The formula, where L B and L C Each is a bidentate ligand; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of the metal M.

9. The compound according to claim 8, wherein the compound has a A )3、Ir(L A )(L B )2、Ir(L A )2(L B )、Ir(L A )2(L C ) and Ir(L A )(L B )(L C ); and wherein L A , L B and L C different from each other; or Pt(L A )(L B ); and wherein L A and L B Can be the same or different.

10. The compound according to claim 8, wherein L B and L C Each independently selected from the group consisting of: in: T is selected from the group consisting of B, Al, Ga and In; K 1 'Selected from the group consisting of: single bond, O, S, NR e , PR e , BR e , CR e R f and SiR e R f ; Y 1 To Y 13 Each of which is independently selected from the group consisting of C and N; Y'Select from the group consisting of: BR e , BR e R f NR e , PR e 、P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e 、C=CR e R f 、S=O、SO2、CR e R f 、SiR e R f and GeR e R f ; R e and R f may be fused or joined to form a ring; Each R a , R b , R c and R d can independently represent monosubstitution to the maximum allowed number of substitutions or no substitution; R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, selenanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d Any two substituents of may be fused or joined to form a ring or to form a polydentate ligand.

11. The compound according to claim 8, wherein L A Can be selected from L Ai , wherein i is an integer from 1 to 582; or selected from L Ai' -(Rm)(Rn)(Ro)(Rp)(Rq), wherein i' is an integer from 1 to 111, and each of Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R130; wherein L A1 (R1)(R1)(R1)(R1)(R1) to L A111 Each of (R130)(R130)(R130)(R130)(R130) is defined in Listing 3a below: or L A You can choose free L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq), wherein g is an integer from 1 to 103, and each of Rl, Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R130; wherein L AB1 (R1)(R1)(R1)(R1)(R1) to L AB103 Each of (R130)(R130)(R130)(R130)(R130) is defined in Listing 3b below: or L A You can choose free L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'), wherein g' is an integer from 1 to 13, each of Rl', Rm', Rn', Ro', Rp' and Rq' is independently selected from the group consisting of R1 to R130; Rq' is selected from E1 to E125 as defined herein; wherein L AC 1-(R1)(R1)(R1)(R1)(R1)(E1) to L AC Each of 13-(R130)(R130)(R130)(R130)(R130)(E125) is defined in Listing 3c below: and L B Can be selected from L Bk , where k is an integer from 1 to 530, where: When the compound has the formula Ir(L Ai )3, the compound is selected from Ir(L A1 )3 to Ir(L A582 )3; When the compound has the formula Ir(L Ai )(L Bk )2, the compound is selected from Ir(L A1 )(L B1 )2 to Ir(L A582 )(L B530 )2; When the compound has the formula Ir(L Ai )2(L Bk ), the compound is selected from Ir(L A1 )2(L B1 ) to Ir(L A582 )2(L B530 ) When the compound has the formula Ir(L Ai )2(L Cj-I ), j is an integer from 1 to 1416, wherein the compound is selected from Ir(L A1 )2(L C1-I ) to Ir(L A582 )2(L C1416-I ) When the compound has the formula Ir(L Ai )2(L Cj-II ), j is an integer from 1 to 1416, wherein the compound is selected from Ir(L A1 )2(L C1-II ) to Ir(L A582 )2(L C1416-II ) When the compound has the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))3, the compound is selected from Ir(L A1 (R1)(R1)(R1)(R1)(R1))3 to Ir(L A111 (R130)(R130)(R130)(R130)(R130))3; When the compound has the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))(L Bk )2, the compound is selected from Ir(L A1 (R1)(R1)(R1)(R1)(R1))(L B1 )2 to Ir(L A111 (R130)(R130)(R130)(R130)(R130))(L B530 )2; When the compound has the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))2(L Bk ), the compound is selected from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L B530 ) is a group of compounds; When the compound has the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))2(L Cj-I ), the compound is selected from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L C1-I ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L C1416-I ) is a group of compounds; When the compound has the formula Ir(L Ai' -(R m )(R n )(R o )(R p )(R q ))2(L Cj-II ), the compound is selected from Ir(L A1 (R1)(R1)(R1)(R1)(R1))2(L C1-II ) to Ir(L A111 (R130)(R130)(R130)(R130)(R130))2(L C1416-II ) is a group of compounds; When the compound has the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))3, the compound is selected from Ir(L AB1 (R1)(R1)(R1)(R1)(R1))3 to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))3; When the compound has the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))(L Bk )2, the compound is selected from Ir(L AB1 (R1)(R1)(R1)(R1)(R1))(L B1 )2 to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))(L B530 )2; When the compound has the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Bk ), the compound is selected from Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L B1 ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L B530 ) is a group of compounds; When the compound has the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Cj-I ), the compound is selected from Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L C1-I ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L C1416-I ) is a group of compounds; When the compound has the formula Ir(L AB g-(Rl)(Rm)(Rn)(Ro)(Rp)(Rq))2(L Cj-II ), the compound is selected from Ir(L AB1 (R1)(R1)(R1)(R1)(R1))2(L C1-II ) to Ir(L AB103 (R130)(R130)(R130)(R130)(R130))2(L C1416-II ) is a group of compounds; When the compound has the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))3, the compound is selected from Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))3 to Ir(L AC The group consisting of compounds of 13-(R130)(R130)(R130)(R130)(R130)(E125))3; When the compound has the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))(L Bk )2, the compound is selected from Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))(L B1 )2 to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))(L B530 )2; When the compound has the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Bk ), the compound is selected from Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L B1 ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L B530 ) is a group of compounds; When the compound has the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Cj-I ), the compound is selected from Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L C1-I ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L C1416-I ) of the group consisting of compounds; and When the compound has the formula Ir(L AC g'-(Rl')(Rm')(Rn')(Ro')(Rp')(Rq'))2(L Cj-II ), the compound is selected from Ir(L AC 1-(R1)(R1)(R1)(R1)(R1)(E1))2(L C1-II ) to Ir(L AC 13-(R130)(R130)(R130)(R130)(R130)(E125))2(L C1416-II ) is a group of compounds; Where R1 to R130 have the structure in the following listing: Among them, E1 to E125 have the following structure: Each L Bk Has the structure defined as follows: Each L Cj-I Based on the formula structure; and Each L Cj-II Based on the formula The structure of Cj-I and L Cj-II Each L Cj , R 201 and R 202 The definition is as follows: Where R D1 to R D246 Has the following structure:

12. The compound of claim 1, wherein the compound is selected from the group consisting of the structures of List 10 below:

13. The compound according to claim 8, wherein the compound has Formula II: in: M 1 is Pd or Pt; Moieties E and F are each independently a monocyclic or polycyclic structure, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; Z 3 and Z 4 each independently is C or N; K.K 3 and K 4 Each is independently selected from the group consisting of a direct bond, O and S, wherein the K, K 3 and K 4 At least two of them are direct bonds; L 1 , L 2 and L 3 Each independently does not exist or is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof, wherein L is present 1 and L 2 at least one of; R E and R F each independently represents zero substitution, monosubstitution, or up to the maximum allowed number of substitutions; R, R', R E and R F each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, selenanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and Two adjacent R A , R B , R C , R E and R F May be joined or fused together to form a ring.

14. An organic light-emitting device, comprising: anode; cathode; and An organic layer is disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.

15. A consumer product comprising an organic light-emitting device, the organic light-emitting device comprising: anode; cathode; and An organic layer is disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.

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