Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. There is provided a compound having a first ligand LA comprising the structure of Formula I, # imgabs 0 # wherein at least one of RA and RB comprises the structure of Formula II, # imgabs 1 # in the compound, each of moieties A and B being a monocyclic or polycyclic fused ring system; each of Z1 to Z4 is C or N; k1 and K2 are each a direct bond or a linking group; l is a direct bond or a linking group; each of Xa and Xb is independently Si or Ge; each R, R ', R1, R2, R3, R4, R5, R alpha, R beta, RA and RB is hydrogen or a universal substituent as defined herein, and LA is coordinated with a metal M having an atomic mass of at least 40. Formulations, OLEDs and consumer products containing the compounds are also provided.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority under 35 USC §119(e) to U.S. Provisional Application No. 63 / 606,412, filed on December 5, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates generally to organic or metal coordination compounds and formulations and various uses thereof, 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] Optoelectronic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many materials used to manufacture the devices are relatively inexpensive, so organic optoelectronic devices have the potential to have cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) can make them more suitable for specific applications, such as manufacturing 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 use in applications such as flat panel displays, lighting, and backlighting.

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

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

[0008] In Formula I:

[0009] Each of moiety A and moiety B is independently a monocyclic or polycyclic fused ring system, wherein each ring in the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0010] Z 1 To Z 4 Each of is independently C or N;

[0011] K 1 and K 2 Each independently selected from the group consisting of: direct key, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β );

[0012] L is selected from the group consisting of: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO 2 , CRR', SiRR' and GeRR';

[0013] R A and R B Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution;

[0014] R A and R B At least one of them comprises a structure of Formula II,

[0015] Each R, R', R 1 , R 2 , R 3 , R 4 , R 5 , R α , R β , R A and R B are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof;

[0016] X a and X b Each of is independently Si or Ge;

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

[0018] M can coordinate with other ligands;

[0019] L A Can be joined with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands;

[0020] Any two substituents may be joined or fused to form a ring;

[0021] The condition is L A Does not contain formula III or Formula IV, The structure of; and the compound is not:

[0022] In another aspect, the present disclosure provides a formulation comprising a compound as described herein having a first ligand L comprising a structure of Formula I A .

[0023] In yet another aspect, the present disclosure provides an OLED having an organic layer, the organic layer comprising a compound as described herein having a first ligand L comprising a structure of Formula I A .

[0024] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound as described herein having a first ligand L comprising a structure of Formula I A . BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 An organic light emitting device is shown.

[0026] Figure 2 An inverted organic light-emitting device without a separate electron transport layer is demonstrated. DETAILED DESCRIPTION

[0027] A. Terminology

[0028] Unless otherwise specified, the following terms used herein are defined as follows:

[0029] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed "above" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, there may be other layers between the first and second layers. For example, a cathode may be described as being "disposed "above" an anode even though various organic layers are present between the cathode and the anode.

[0030] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0031] As used herein, and as will be generally understood by one skilled in the art, a first "Highest Occupied Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum energy level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram with the vacuum energy level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears closer to the top of this diagram than a "lower" HOMO or LUMO energy level.

[0032] As used herein, and as one skilled in the art would generally understand, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are typically measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being farther away from the vacuum level in a downward direction. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0033] Layers, materials, regions, and devices may be described herein with reference to the color of light they emit. Generally, as used herein, an emissive region described as producing a particular color of light may include one or more emissive layers disposed above each other in a stacked manner.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] In some cases, it may be preferred to describe the color of a component, such as the color of an emitting region, a sub-pixel, a color-changing layer, etc., in terms of 1931 CIE coordinates. For example, a yellow emitting material may have multiple peak emission wavelengths, one in or near the edge of a "green" region, and one in or near the edge of a "red" region, as previously described. Thus, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. Shapes in the 1931 CIE color space are constructed by tracing the trajectory between two color points and any other interior points. For example, the interior shape parameters for red, green, blue, and yellow may be defined as follows:

[0038]

[0039] The terms "halo," "halogen," and "halo" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0040] The term "acyl" refers to a substituted carbonyl (-C(O)-R s ).

[0041] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0042] The term "ether" refers to -OR s Group.

[0043] The terms "thio" or "thioether" are used interchangeably and refer to -SR s Group.

[0044] The term "selenoalkyl" refers to -SeR s Group.

[0045] The term "sulfinyl" refers to -S(O)-R s Group.

[0046] The term "sulfonyl" refers to -SO 2 -R s Group.

[0047] The term "phosphino" refers to a group containing at least one phosphorus atom bonded to a related structure. Common examples of phosphino groups include, but are not limited to, -P(R s ) 2 Group or -PO(R s ) 2 A group of groups, where each R s Can be the same or different.

[0048] The term "silyl group" refers to a group containing at least one silicon atom bonded to the associated structure. Common examples of silyl groups include, but are not limited to, -Si(R s ) 3 A group of groups, where each R s Can be the same or different.

[0049] The term "germanyl" refers to a group containing at least one germanium atom bonded to an associated structure. Common examples of germanyl groups include, but are not limited to, -Ge(R s ) 3 A group of groups, where each R s Can be the same or different.

[0050] The term "boryl" refers to a group containing at least one boron atom bonded to the structure of interest. Common examples of boryl groups include, but are not limited to, -B(R s ) 2 Group or its Lewis adduct -B(R s ) 3 A group of groups, where R s Can be the same or different.

[0051] In each of the above, R s It may be hydrogen or a substituent selected from the group consisting of general substituents as defined in this application. s is selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. More preferably, R s Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0052] The term "alkyl" refers to and includes both straight and branched chain alkyl groups having alkyl carbon atoms bonded to the relevant structure. Preferred alkyl groups are those 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, and the like. In addition, the alkyl group may be further substituted.

[0053] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spirocycloalkyl groups having cycloalkyl carbon atoms bonded to the related structure. Preferred cycloalkyl groups are cycloalkyl groups 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, and the like. In addition, the cycloalkyl group may be further substituted.

[0054] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, at least one heteroatom is selected from O, S, N, P, B, Si, Ge and Se, preferably O, S or N. In addition, the heteroalkyl or heterocycloalkyl group may be further substituted.

[0055] The term "alkenyl" refers to and includes both straight and branched olefin groups. Alkenyl is essentially an alkyl group including at least one carbon-carbon double bond in the alkyl chain, wherein one carbon atom is from a carbon-carbon double bond bonded to a related structure. Cycloalkenyl is essentially a cycloalkyl group including at least one carbon-carbon double bond in a cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, 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 two to fifteen carbon atoms. In addition, alkenyl, cycloalkenyl or heteroalkenyl groups may be further substituted.

[0056] The term "alkynyl" refers to and includes both straight and branched alkyne groups. Alkynyl groups are essentially alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain, wherein one carbon atom is from a carbon-carbon triple bond that is bonded to a related structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. In addition, alkynyl groups may be further substituted.

[0057] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group bonded to an alkyl carbon atom of the associated structure. Additionally, the aralkyl group may be further substituted.

[0058] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, at least one heteroatom is selected from O, S, Se, N, P, B, Si, Ge and Se, preferably O, S, N or B. Heteroaromatic cyclic groups can be used interchangeably with heteroaryl groups. Preferred non-aromatic heterocyclic groups are non-aromatic heterocyclic groups containing 3 to 10 ring atoms, preferably non-aromatic heterocyclic groups containing 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines, such as morpholinyl, piperidinyl, pyrrolidinyl, etc., and cyclic ethers / thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. In addition, the heterocyclic group can be further substituted or fused.

[0059] The term "aryl" refers to and includes both monocyclic and polycyclic aromatic hydrocarbon groups. Polycyclics may have two or more rings in which 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 carbons, ten carbons, twelve carbons, fourteen carbons, or eighteen carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene and naphthalene. In addition, the aryl group may be further substituted or fused, such as but not limited to fluorene.

[0060] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom. 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. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Polycyclic heterocyclic ring systems may have two or more aromatic rings, wherein two atoms are common to two adjacent rings (the rings are "fused"), wherein at least one of the rings is a heteroaryl. Polycyclic heteroaromatic ring systems may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls 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, pyridyl indole, pyrrolobipyridine, 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, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenophenodipyridine, azaborane, borazine, 5λ 2 ,9λ 2 -diaza-13b-borazinnaphtho[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 -diaza-13b-borazinnaphtho[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. In addition, the heteroaryl group may be further substituted or fused.

[0061] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 5λ 2 ,9λ 2-diaza-13b-borazinnaphtho[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 the corresponding aza analogs of each are of particular interest.

[0062] In many cases, the universal substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0063] In some cases, preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0064] In some cases, more preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, aryl, heteroaryl, nitrile, thio, and combinations thereof.

[0065] In some cases, even more preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, silane, aryl, heteroaryl, nitrile, and combinations thereof.

[0066] In still other cases, the most preferred universal substituents are selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0067] The terms "substituted" and "substituted" refer to the bonding of substituents other than H to the relevant positions, such as carbon or nitrogen. For example, when R 1 When it represents a single substitution, one R 1 must not be H (i.e., substituted). Similarly, when R 1 When it indicates disubstituted, the two R 1 must not be H. Similarly, when R 1 When it indicates zero or no substitution, R 1 For example, it can be hydrogen with all available valences of the ring atoms, such as the carbon atoms of benzene and the nitrogen atoms in pyrrole, or simply none for ring atoms with fully saturated valences, such as the nitrogen atoms in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences in the ring atoms.

[0068] 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, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloaralkyl. In one example, the term substitution includes a combination of two to four listed groups. In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination 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, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0069] The "aza" designation in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the CH groups in the corresponding aromatic ring can be replaced by a nitrogen atom, for example and without any limitation, azatriphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be covered by the term as set forth herein.

[0070] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be easily 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 entirety) 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 entirety) respectively describe the deuteration of methylene hydrogen in benzylamine and the effective way to replace aromatic ring hydrogen with deuterium.

[0071] As used herein, any specific 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 a valence 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 Meaning includes C 6 H 6 , C 6 D 6 , C 6 H 3 D 3 and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, but are not limited to, CD 3 , CD 2 C(CH 3 ) 3 、C(CD 3 ) 3 and C 6 D 5 .

[0072] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name can be written as if it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0073] In some cases, a pair of substituents in a molecule can be optionally joined or fused to form a ring. Preferred rings are five- to nine-membered carbocyclic or heterocyclic rings, including two cases in which the portion of the ring formed by the pair of substituents is saturated and the portion of the ring formed by the pair of substituents is unsaturated. In other cases, a pair of adjacent substituents can be optionally joined or fused to form a ring. As used herein, "adjacent" means that the two substituents involved can be adjacent to each other on the same ring, or on two adjacent rings with two closest available substitutable positions (such as 2, 2' positions in biphenyl or 1, 8 positions in naphthalene).

[0074] B. Compounds of the Disclosure

[0075] In one aspect, the present disclosure provides a compound having a first ligand L comprising a structure of Formula I A ,

[0076] In Formula I:

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

[0078] Z 1 To Z 4 Each of is independently C or N;

[0079] K 1 and K 2 Each independently selected from the group consisting of: direct key, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β );

[0080] L is selected from the group consisting of: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO 2 , CRR', SiRR' and GeRR';

[0081] R A and R B Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution;

[0082] R A and R B At least one of them comprises a structure of Formula II,

[0083] Each R, R', R 1 , R 2 , R 3 , R 4 , R 5 , R α , R β , R A and R B is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein;

[0084] X a and X b Each of is independently Si or Ge;

[0085] L A coordinated to a metal M having an atomic mass of at least 40;

[0086] M can coordinate with other ligands;

[0087] L A can be joined with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; and

[0088] Any two substituents may be joined or fused to form a ring.

[0089] In some embodiments, L A Does not contain formula III or Formula IV, In some embodiments, the compound is not:

[0090] In some embodiments, the first ligand L A Having a structure of Formula I. In some embodiments, the first ligand L A Consisting essentially of the structure of Formula I.

[0091] In some embodiments of Formula I, at least one of R, R', R A , R B , R 1 , R 2 , R 3 , R 4 or R 5 is partially or fully deuterated. In some embodiments, at least one R A is partially or fully deuterated. In some embodiments, at least one R B 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 4 is partially or fully deuterated. In some embodiments, at least one R 5 In some embodiments, at least one R or R' is partially or fully deuterated.

[0092] In some embodiments, each of R, R', R 1 , R 2 , R 3 , R 4 , R 5 , R α , R β , R A and R B is independently hydrogen or a substituent selected from the group consisting of preferred common substituents. In some embodiments, each of R, R', R 1 , R 2 , R3 , R 4 , R 5 , R α , R β , R A and R B is independently hydrogen or a substituent selected from the group consisting of more preferred common substituents. In some embodiments, each of R, R', R 1 , R 2 , R 3 , R 4 , R 5 , R α , R β , R A and R B is independently hydrogen or a substituent selected from the group consisting of the most preferred common substituents.

[0093] In some embodiments, the metal M is selected from the group consisting of: Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu. In some embodiments, the metal M is selected from the group consisting of: Os, Ir, Cu, Ag, and Au. In some embodiments, the metal M is Ir. In some embodiments, the metal M is Au or Cu.

[0094] In some embodiments, each of moiety A and moiety B 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, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza- Benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole, aza-benzimidazole-derived carbenes, naphtho-imidazole, aza-naphtho-imidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, phenanthro[3,2-b]benzofuran, 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 located on the benzo ring. In some embodiments, the aza variant includes one N located on the benzo ring and the N is bonded to the metal M.

[0095] In some embodiments, moiety A is a monocyclic ring. In some embodiments, moiety A is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, and imidazole-derived carbene. In some embodiments, moiety A is pyridine, imidazole, or imidazole-derived carbene. In some embodiments, moiety A is pyridine. In some embodiments, moiety A is imidazole. In some embodiments, moiety A is an imidazo-derived carbene.

[0096] 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, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole, naphtho-imidazole, aza-naphtho-imidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, aza-fluorene, and aza-benzimidazole-derived carbenes. In some embodiments, moiety A is quinoline, isoquinoline, aza-benzothiophene, or aza-dibenzothiophene. In some embodiments, moiety A is quinoline. In some embodiments, moiety A is isoquinoline. In some embodiments, moiety A is aza-benzothiophene. In some embodiments, moiety A is aza-dibenzothiophene.

[0097] In some embodiments, moiety B is a monocyclic ring. In some embodiments, moiety B is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole and triazole. In some embodiments, moiety B is benzene.

[0098] In some embodiments, moiety B is a polycyclic fused ring system. In some embodiments, moiety B 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, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, phenanthro[3,2-b]benzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, moiety B is naphthalene, dibenzofuran, or aza-dibenzofuran. In some embodiments, moiety B is naphthalene. In some embodiments, moiety B is dibenzofuran. In some embodiments, moiety B is aza-dibenzofuran.

[0099] In some embodiments, each of part A and part B can be independently a polycyclic fused ring structure. In some embodiments, each of part A and part B can be independently 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 one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to the metal M and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, each of part A and part B can be independently selected from the group consisting of: dibenzofuran, dibenzothiophene, dibenzoselenophene and its aza variant. In some such embodiments, each of part A and part B can be independently substituted by a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl and a combination thereof at the ortho or meta position of O, S or Se atoms. In some such embodiments, the aza variant contains exactly one N atom at the 6 position (ortho position of O, S or Se) and contains a substituent at the 7 position (meta position of O, S or Se).

[0100] In some embodiments, each of part A and part B can independently 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 the 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 by a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof.

[0101] In some embodiments, each of part A and part B can independently be a polycyclic condensed ring structure comprising at least five condensed rings. In some embodiments, the polycyclic condensed ring structure comprises four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments with a 5-membered ring, the 5-membered ring is fused with the ring coordinated to the metal M, the second 6-membered ring is fused with the 5-membered ring, the third 6-membered ring is fused with the second 6-membered ring, and the fourth 6-membered ring is fused with the third 6-membered ring.

[0102] In some embodiments, each of part A and part B can independently be an aza form of a polycyclic fused ring as described above. In some such embodiments, each of part A and part B can independently contain exactly one aza N atom. In some such embodiments, each of part A and part B contains exactly two aza N atoms, which can be in one ring or in two different rings. In some such embodiments, the ring with the aza N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring with 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.

[0103] In some embodiments, Z 1 is N and Z 4 is C. In some embodiments, Z 2 and Z 3 It is C.

[0104] In some embodiments, Z 1 is carbene C and Z 4 is C. In some embodiments, Z 2 is N and Z 3 It is C.

[0105] In some embodiments, K 1 It is a direct key.

[0106] In some embodiments, K 1 is O or S. In some embodiments, K 1 is O. In some embodiments, K 1 It’s S.

[0107] In some embodiments, K 1 is N(R α )、P(R α ) or B(R α ). In some embodiments, K 1 is C(R α )(Rβ ) or Si(R α )(R β ).

[0108] In some embodiments, K 2 It is a direct key.

[0109] In some embodiments, K 2 is O or S. In some embodiments, K 2 is O. In some embodiments, K 2 It’s S.

[0110] In some embodiments, K 2 is N(R α )、P(R α ) or B(R α ). In some embodiments, K 2 is C(R α )(R β ) or Si(R α )(R β ).

[0111] In some embodiments, K 1 and K 2 Each of K is a direct key. In some embodiments, K 1 is a direct key, and K 2 Not a direct key.

[0112] In some embodiments, L is a direct bond. In some embodiments, L is selected from the group consisting of O, S, and Se.

[0113] In some embodiments, L is selected from the group consisting of BR, NR, and PR. In some embodiments, L is BR. In some embodiments, L is NR. In some embodiments, L is PR. In some such embodiments, R is aryl or heteroaryl. In some such embodiments, R is aryl or heteroaryl and is in combination with R A or R B In some such embodiments, the ring containing B, N or P is a 5-membered ring.

[0114] In some embodiments, L is selected from the group consisting of: P(O)R, C=O, C=S, C=Se, C=NR', C=CRR', S=O, and SO 2 In some embodiments, L is selected from the group consisting of: BRR', CRR', SiRR', and GeRR'. In some embodiments, L is CR.

[0115] In some embodiments, the compound comprises an electron withdrawing group.

[0116] In some embodiments, the compound comprises an electron withdrawing group having a Hammett constant greater than 0. In some embodiments, the electron withdrawing group has a Hammett constant 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.

[0117] In some embodiments, Formula I comprises an electron withdrawing group selected from the group consisting of the following structures listed in the EWG1 list: F, CF 3 、CN、COCH 3 , CHO, COCF 3 、COOMe、COOCF 3 、NO 2 , SF 3 、SiF 3 PF 4 , SF 5 、OCF 3 、SCF 3 、SeCF 3 、SOCF 3 、SeOCF 3 、SO 2 F. SO 2 CF 3 , SeO 2 CF 3 、OSeO 2 CF 3 、OCN、SCN、SeCN、NC、 + N(R k2 ) 3 , (R k2 ) 2 CCN, (R k2 ) 2 CCF 3 、CNC(CF 3 ) 2 , BR k3 R k2, substituted or unsubstituted dibenzoborole, 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, cyano-containing alkyl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,

[0118]

[0119] Each R k1 represents mono-substitution to the maximum permissible substitution or no substitution;

[0120] where Y G Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO 2 , CR e R f 、SiR e R f and GeR e R f' ;and

[0121] Where R k1 , R k2 , R k3 , R e and R f Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein.

[0122] In some embodiments, Formula I comprises an electron withdrawing group selected from the group consisting of the following structures listed in EWG2:

[0123]

[0124]

[0125] In some embodiments, Formula I comprises an electron withdrawing group selected from the group consisting of the following structures listed in EWG3:

[0126]

[0127] In some embodiments, Formula I comprises an electron withdrawing group selected from the group consisting of the following structures listed in EWG4:

[0128]

[0129] In some embodiments, Formula I comprises an electron withdrawing group, and the electron withdrawing group is a π-electron-deficient electron withdrawing group. In some embodiments, the π-electron-deficient electron withdrawing group is selected from the group consisting of the following structures in the Pi-EWG list: CN, COCH 3 , CHO, COCF 3 、COOMe、COOCF 3 、NO 2 , SF 3 、SiF 3 PF 4 , SF 5 、OCF 3 、SCF 3 、SeCF 3 、SOCF 3 、SeOCF 3 、SO 2 F. SO 2 CF 3 , SeO 2 CF 3 、OSeO 2 CF 3 、OCN、SCN、SeCN、NC、 + N(R k2 ) 3 , BR k2 R k3, substituted or unsubstituted dibenzoborole, 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,

[0130] The variables are the same as defined previously.

[0131] In some embodiments, the compound comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, the compound comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, the compound comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, the compound comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, the compound comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0132] In some embodiments, 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 Pi-EWG list as defined herein.

[0133] In some embodiments, 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 Bis 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 Pi-EWG list as defined herein.

[0134] In some embodiments, at least one R 1 , R 2 or R 3 is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 1 , R 2 or R 3 is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 1 , R 2 or R 3 is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 1 , R 2 or R 3 is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 1 , R 2 or R 3 is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0135] In some embodiments, at least one R 4 or R 5 is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 4 or R 5 is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 4 or R 5 is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 4 or R 5 is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 4 or R 5 is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0136] In some embodiments, at least one R A The structure comprising Formula II.

[0137] In some embodiments, at least one R B The structure comprising Formula II.

[0138] In some embodiments, R A or R B In some embodiments, at least one R A Containing Formula II, and at least one R B Comprising Formula II.

[0139] In some embodiments, for at least one structure of Formula II, X a is Si and X b It's Si.

[0140] In some embodiments, for at least one structure of Formula II, X a is Ge and X b It's Ge.

[0141] In some embodiments, for at least one structure of Formula II, X a is Si and X b It's Ge.

[0142] In some embodiments, for at least one structure of Formula II, X a is Ge and X b It's Si.

[0143] In some embodiments, R 1 To R 5 In some embodiments, at least one of R 1 To R 5 At least two of are not hydrogen or deuterium. In some embodiments, R 1 To R 5 At least three of R are not hydrogen or deuterium. 1 To R 5 At least four of R are not hydrogen or deuterium. 1 To R 5 At least five of them are not hydrogen or deuterium.

[0144] In some embodiments, R 1 To R 5 At least one of contains at least one C atom. In some embodiments, R 1 To R 5 At least two of R include at least one C atom. 1 To R 5 At least three of R include at least one C atom. In some embodiments, R1 To R 5 At least four of the R 1 To R 5 At least five of them contain at least one C atom.

[0145] In some embodiments, R 1 To R 5 At least one of contains at least two C atoms. In some embodiments, R 1 To R 5 At least one of contains at least three C atoms. In some embodiments, R 1 To R 5 At least one of the comprises at least four C atoms.

[0146] In some embodiments, R 1 To R 5 At least one of the above independently comprises a substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and combinations thereof. 1 To R 5 In some embodiments, at least one of R 1 To R 5 At least one of the above independently comprises a methyl group.

[0147] In some embodiments, R 1 To R 5 At least two of the R independently comprise substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. 1 To R 5 In some embodiments, at least two of R independently comprise an alkyl group. 1 To R 5 At least two of the above independently contain a methyl group.

[0148] In some embodiments, R 1 To R 5 In some embodiments, at least two of R 1 To R 5 In some embodiments, at least three of R 1 To R 5 In some embodiments, at least four of R 1 To R 5 Each of has a different substituent.

[0149] In some embodiments, the structure of Formula II is bonded to moiety A or moiety B via a direct bond.

[0150] In some embodiments, the structure of Formula II is connected by an organic linker group L Y Bonded to either part A or part B.

[0151] In some embodiments, L Y 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, SO 2 , CRR', SiRR', GeRR', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof.

[0152] In some embodiments, L Y is a substituted or unsubstituted aryl or heteroaryl. In some embodiments, L Y is a substituted or unsubstituted aryl group. In some embodiments, L Y is substituted or unsubstituted benzene. In some embodiments, L Y is a substituted or unsubstituted biphenyl.

[0153] In some embodiments, L Y is a 6-membered aromatic ring, and the structure of formula II is Y In some embodiments, L Y 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, SO 2 , CRR', SiRR', GeRR' and combinations thereof.

[0154] In some embodiments, X a or X b Bonded to moiety A or moiety B. In some embodiments, X a or X b Forms a direct bond with either moiety A or moiety B without passing through the dashed line of Formula II. a or X b An indirect bond is formed with either moiety A or moiety B, not via the dashed line of formula II.

[0155] In some embodiments, X a or X b The only bond between X and either moiety A or moiety B is the dashed line of Formula II. a and X b Each of is independently bonded to either moiety A or moiety B.

[0156] In some embodiments, at least one RA is not hydrogen. In some embodiments, at least one R A In some embodiments, at least one R A Contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0157] In some embodiments, at least one R B is not hydrogen. In some embodiments, at least one R B In some embodiments, at least one R B Contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0158] In some embodiments, Formula II has a structure selected from the group consisting of the structures of Listing 1 below:

[0159]

[0160]

[0161]

[0162] In some embodiments, the ligand L A Selected from the group consisting of the following structures of Listing 2:

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] in:

[0174] T is selected from the group consisting of B, Al, Ga and In;

[0175] K 1 and K 1 Each of ' is independently selected from the group consisting of: direct key, NR e , PR e , O, S and Se;

[0176] Y 1 To Y 23 Each of is independently selected from the group consisting of carbon and nitrogen;

[0177] W 1 Selected from the group consisting of: direct bond, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO 2 , CRR', P(O)R, SiRR' and GeRR';

[0178] W 2 is B, N or P;

[0179] Y' and Y" are selected from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO 2 、C=CR e R f 、C=NR e , CR e R f 、P(O)R e 、SiR e R f and GeR e R f ;

[0180] Each R a , R b , R c and R d independently represents zero substitution, monosubstitution, or up to the maximum allowed number of substitutions on its associated ring;

[0181] R, R', R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R fEach of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0182] Any two adjacent R, R', R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f They may be fused or joined to form a ring or to form a multidentate ligand.

[0183] In ligand L A In some embodiments selected from List 1, at least one R a , R b , R c or R d In some embodiments, at least one R a In some embodiments, at least one R b In some embodiments, at least one R c Selected from the group consisting of general substituents defined herein. In some embodiments, at least one R d is selected from the group consisting of general substituents as defined herein. A In some embodiments selected from List 2, at least one R a , R b , R c or R d is partially or fully deuterated. In some embodiments, at least one R a is partially or fully deuterated. In some embodiments, at least one R b is partially or fully deuterated. In some embodiments, at least one R c is partially or fully deuterated. In some embodiments, at least one R d is partially or fully deuterated.

[0184] In ligand L A In some embodiments selected from List 2, 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 ais 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 Pi-EWG list as defined herein.

[0185] In ligand L A In some embodiments selected from List 2, 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 Pi-EWG list as defined herein.

[0186] In ligand L A In some embodiments selected from List 2, 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 Pi-EWG list as defined herein.

[0187] In ligand L A In some embodiments selected from List 2, at least one R d is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R dis or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0188] In some embodiments, the ligand L A Selected from the group consisting of the following structures of Listing 3:

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] in:

[0196] K 1 'Selected from the group consisting of: direct key, NR e , PR e , O, S and Se;

[0197] X, Y 2 To Y 5 and Y 9 -Y 12 Each of is independently selected from the group consisting of carbon and nitrogen;

[0198] W 1 Selected from the group consisting of: direct bond, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO 2 , CRR', P(O)R, SiRR' and GeRR';

[0199] W 2 is B, N or P;

[0200] Y' and Y" are selected from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO 2 、C=CR e R f、C=NR e , CR e R f 、P(O)R e 、SiR e R f and GeR e R f ;

[0201] Each R a , R b , R c and R d independently represents zero substitution, monosubstitution, or up to the maximum allowed number of substitutions on its associated ring;

[0202] R, R', R a , R b , R c , R d , R e and R f Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0203] Any two adjacent R, R', R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f They may be fused or joined to form a ring or to form a multidentate ligand.

[0204] In ligand L A In some embodiments selected from List 3, X, Y 2 To Y 5 and Y 9 -Y 12 In some embodiments, Y 2 is N. In some embodiments, Y 3 is N. In some embodiments, Y 4 is N. In some embodiments, Y 5 is N. In some embodiments, Y 9 is N. In some embodiments, Y 10 is N. In some embodiments, Y 11 is N. In some embodiments, Y 12 is N. In some embodiments, Y' is O. In some embodiments, Y" is O. In some embodiments, K 1' It is a direct key.

[0205] In ligand L A In some embodiments selected from Listing 3, at least one R a , R b , R c or R d Selected from the group consisting of general substituents defined herein. In some embodiments, at least one R a Selected from the group consisting of general substituents defined herein. In some embodiments, at least one R b Selected from the group consisting of general substituents defined herein. In some embodiments, at least one R c Selected from the group consisting of general substituents defined herein. In some embodiments, at least one R d is selected from the group consisting of general substituents as defined herein. A In some embodiments selected from Listing 3, at least one R a , R b , R c or R d is partially or fully deuterated. In some embodiments, at least one R a is partially or fully deuterated. In some embodiments, at least one R b is partially or fully deuterated. In some embodiments, at least one R c is partially or fully deuterated. In some embodiments, at least one R d is partially or fully deuterated.

[0206] In ligand L A In some embodiments selected from Listing 3, 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 Pi-EWG list as defined herein.

[0207] In ligand L A In some embodiments selected from List 2, 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 bis 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 Pi-EWG list as defined herein.

[0208] In ligand L A In some embodiments selected from Listing 3, 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 Pi-EWG list as defined herein.

[0209] In ligand L A In some embodiments selected from Listing 3, at least one R d is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R d is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0210] In some embodiments, the ligand L A Choose from L Ai (R E )(R J )(R K )(R L ), where i is an integer from 1 to 256, R J , R K and R LEach of which is independently selected from R 1 To R 150 The group is composed of E Choose from R E1 To R E94 The group consisting of L A1 (R E1 )(R 1 )(R 1 )(R 1 ) to L A256 (R E94 )(R 150 )(R 150 )(R 150 ) are each defined in Listing 4 below:

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] Where R E1 To R E94 With the following structure defined in Listing 1 below:

[0230]

[0231]

[0232] Where R 1 To R 150 With the structure defined in Listing 5 below:

[0233]

[0234]

[0235]

[0236] In some embodiments, the compound has the formula M(L A ) p (L B ) q (L C ) r , 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.

[0237] 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 where L A , L B and L C Different from each other.

[0238] In some embodiments, L Bcomprises 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 Electron withdrawing groups from the Pi-EWG list as defined herein are included.

[0239] 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, L C 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 Electron withdrawing groups from the Pi-EWG list as defined herein are included.

[0240] In some embodiments, L B is a substituted or unsubstituted phenylpyridine, and L C is a substituted or unsubstituted acetylacetonate.

[0241] In some embodiments, the compound has the formula Pt(L A )(L B ); and where L A and L B Can be the same or different. In some embodiments, L A and L B Connect to form a tetradentate ligand.

[0242] In some embodiments, L B and L C Each independently selected from the group consisting of the structures of Listing 6 below:

[0243]

[0244]

[0245]

[0246] in:

[0247] T is selected from the group consisting of B, Al, Ga and In;

[0248] 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 ;

[0249] Y 1 To Y 13 Each of which is independently selected from the group consisting of C and N;

[0250] 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、SO 2 , CR e R f 、SiR e R f and GeR e R f ;

[0251] R e and R f may be fused or joined to form a ring;

[0252] Each R a , R b , R c and R d independently represents monosubstituted to the maximum allowed number of substitutions or no substitution;

[0253] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0254] Ra1 , 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.

[0255] In ligand L B or L C In some embodiments selected from Listing 6, at least one R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e or R f is or comprises a structure of Formula II.

[0256] In some embodiments, L B and L C Each independently selected from the group consisting of the structures of Listing 7 below:

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] in:

[0267] R a '、R b '、R c '、R d ' and R e ' each independently represents zero substitution, monosubstitution or up to the maximum allowed number of substitutions on its associated ring;

[0268] R a '、R b '、R c '、R d ' and R e ' are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0269] R a '、R b '、R c '、R d ' and R e The two substituents of ' may be fused or joined to form a ring or to form a multidentate ligand.

[0270] In some embodiments, L B Contains the following structure: wherein all variables are the same as previously defined. In some embodiments, Y 1 To Y 4 In some embodiments, Y 1 To Y 4 At least one of is N. In some embodiments, Y 1 To Y 4 Exactly one of 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 group, a silane group or a germanium group. In some embodiments, at least one R a In some embodiments, Y 3 is C, and the R connected to it a is a tertiary alkyl group, a silane group or a germanium group. 1 To Y 3 It's C, Y 4 is N and connected to Y 3 R a is a tertiary alkyl group, a silane group or a germanium group. 1 To Y 3 It's C, Y 4 is N and connected to Y 2 R a is a tertiary alkyl group, a silane group or a germanium group. In some embodiments, at least one R b is a tertiary alkyl, a silane group or a germanium 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 Rb or a pair of R a and R b Join or condense into a ring.

[0271] In ligand L B or L C In some embodiments selected from Listing 7, at least one R a '、R b '、R c '、R d ' or R e ' is or comprises a structure of formula II.

[0272] In some embodiments, the compound has the formula Ir(L A ) 3 、Formula Ir(L A )(L Bk ) 2 、Formula Ir(L A ) 2 (L Bk ), formula Ir(L A ) 2 (L Cj-I ) or formula Ir(L A ) 2 (L Cj-II ),

[0273] Where L A According to any of the embodiments described herein, including L A1 (R E1 )(R 1 )(R 1 )(R 1 ) to L A256 (R E94 )(R 150 )(R 150 )(R 150 );

[0274] Where k is an integer from 1 to 530, and each L Bk With the following structure defined in Listing 8:

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] Where j is an integer from 1 to 1416, and each L Cj-I Has a structure based on the following formula: and

[0291] Each L Cj-II Has a structure based on the following formula: For L Cj-I and L Cj-II Each L Cj , R 201 and R 202 Each is independently defined in Listing 9 below:

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302] Where R D1 To R D246 With the following structure in Listing 10:

[0303]

[0304]

[0305]

[0306]

[0307] In some embodiments, the compound is selected from the group consisting of L Bk The group consisting of those compounds corresponding to one of the following: 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 , L B371 , 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 .

[0308] In some embodiments, the compound is selected from the group consisting of L Bk The group consisting of those compounds corresponding to one of the following: L B1 , L B30 , LB31 , L B125 , L B138 , L B171 , L B172 , L B356 , L B357 , L B367 , L B371 , L B382 , L B455 and L B456 .

[0309] In some embodiments, compounds are selected only from the group consisting of Cj-I or L Cj-II The group of compounds consisting of ligands corresponding to R 201 and R 202 is 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 , RD155 , 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 .

[0310] In some embodiments, compounds are selected only from the group consisting of Cj-I or L Cj-II The group of compounds consisting of ligands corresponding to R 201 and R 202 is defined as 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 , R D136 , 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 .

[0311] In some embodiments, the compounds are selected only from Cj-I The group consisting of those compounds whose ligand has one of the structures listed in List 11 below:

[0312]

[0313]

[0314] In some embodiments, L B' Selected from L B'w , where w is an integer from 1 to 224, and each L B'w Defined in Listing 12 below:

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328] 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 Selected from the group consisting of the structures of List 2, List 3, and List 4, L B Select from List 6, List 7, List 8 (L Bk ) and Listing 12 (L Bw ) structure, and L C Selected from L defined herein Cj-I and L Cj-II A group of structures.

[0329] In some embodiments, L A is selected from the group consisting of the structures of Listing 2, and L B Choose from L Bk wherein k is an integer from 1 to 530. In some embodiments, L A is selected from the group consisting of the structures of Listing 3, and L B Choose from L Bk In some embodiments, L A Choose Freestyle L Ai (R E )(R J )(R K )(R L ) defined by the structure L as defined herein A1 (R E1 )(R 1 )(R 1 )(R 1 ) to L A256 (R E94 )(R 150 )(R 150 )(R 150 ) and L B Choose from L Bk wherein k is an integer from 1 to 530. In some embodiments, L A Choose Freestyle L Ai -(R E )(R J )(R K )(R L) defined by the structure L as defined herein A1 (R E1 )(R 1 )(R 1 )(R 1 ) to L A256 (R E94 )(R 150 )(R 150 )(R 150 ) and L B Choose from L B'w wherein w is an integer from 1 to 224. In some embodiments, L A is selected from List 2 as defined herein, and L C Choose from L Cj-I and L Cj-II A group of structures consisting of, wherein j is an integer from 1 to 1416.

[0330] In some embodiments, the compound may have:

[0331] Formula Ir(L Ai (R E )(R J )(R K )(R L )) 3 , which is composed of compound Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 3 to

[0332] Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 )) 3 composition;

[0333] Formula Ir(L Ai (R E )(R J )(R K )(R L )) 2 (L B ), which is composed of compound Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 2 (L B ) to Ir(L A256(R E94 )(R 150 )(R 150 )(R 150 )) 2 (L B )composition;

[0334] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L B ) 2 , which is composed of compound Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 ))(L B ) 2 To Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B ) 2 composition;

[0335] Formula Ir(L A )(L Bk ) 2 , which is composed of compound Ir(L A )(L B1 ) 2 To Ir(L A )(L B522 ) 2 composition;

[0336] Formula Ir(L A ) 2 (L Bk ), which is composed of compound Ir(L A ) 2 (L B1 ) to Ir(L A ) 2 (L B522 )composition;

[0337] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L Bk ) 2 , which consists of Ir(L A1 (R E1 )(R1 )(R 1 )(R 1 ))(L B1 ) 2 To Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B522 ) 2 The compound composition of

[0338] Formula Ir(L Ai (R E )(R J )(R K )(R L )) 2 (L Bk ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 2 (L B1 ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 )) 2 (L B522 ) of the compound composition;

[0339] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L B'w ) 2 , which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 ))(L B'1 ) 2 To Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B'224 ) 2 The compound composition of

[0340] Formula Ir(L Ai (R E )(RJ )(R K )(R L )) 2 (L B'w ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 2 (L B'1 ) to Ir(L A256 -(R E94 )(R 150 )(R 150 )(R 150 )) 2 (L B'224 ) of the compound composition;

[0341] Formula Ir(L Ai (R E )(R J )(R K )(R L )) 2 (L Cj-I ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 2 (L C1-I ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 )) 2 (L C1416-I ) of the compound composition;

[0342] Formula Ir(L Ai (R E )(R J )(R K )(R L )) 2 (L Cj-II ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 )) 2 (L C1-II ) to Ir(L A256 (R E94 )(R 150 )(R 150)(R 150 )) 2 (L C1416-II ) of the compound composition;

[0343] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L Bk )(L Cj-I ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 ))(L B1 )(L C1-I ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B522 )(L C1416-I ) of the compound composition;

[0344] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L Bk )(L Cj-II ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 ))(L B1 )(L C1-II ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B522 )(L C1416-II ) of the compound composition;

[0345] Formula Ir(L Ai (R E )(R J )(R K )(R L ))(L B'w )(L Cj-I ), which consists of Ir(L A1 (R E1 )(R1 )(R 1 )(R 1 ))(L B'1 )(L C1-I ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B'224 )(L C1416-I ), or a compound of formula

[0346] Ir(L Ai (R E )(R J )(R K )(R L ))(L B'w )(L Cj-II ), which consists of Ir(L A1 (R E1 )(R 1 )(R 1 )(R 1 ))(L B'1 )(L C1-II ) to Ir(L A256 (R E94 )(R 150 )(R 150 )(R 150 ))(L B'224 )(L C1416-II ) of the compound composition,

[0347] Where L A1 (R E1 )(R 1 )(R 1 )(R 1 ) to L A256 -(R E94 )(R 150 )(R 150 )(R 150 )、L B1 To L B522 , L B'1 To L B'224 and L Cj-I L Cj-II , L C1-I To L C1416-I and L C1-II To L C1416-II All are as defined herein.

[0348] In some embodiments, the compound is selected from the group consisting of the structures in Listing 13 below:

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361] In some embodiments, the first ligand L described herein having a structure comprising Formula I A The compound can 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 deuterated percentage has its ordinary meaning and includes the percentage of all possible hydrogen atoms (such as hydrogen or deuterium positions) occupied by deuterium atoms in the compound. In some embodiments, the carbon atoms constituting the ring coordinated to the metal M are completely or partially deuterated. In some embodiments, the carbon atoms contained by the polycyclic system coordinated to the metal M are completely or partially deuterated. In some embodiments, the substituents connected to the monocyclic or fused polycyclic system coordinated to the metal M are completely or partially deuterated.

[0362] 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. Narrower FWHM means better color purity for OLED display applications.

[0363] In the case of a compound having the formula M(L A ) p (L B ) q (L C) r In some embodiments of the heteroleptic compound, the ligand L A Having a first substituent R I , wherein the first substituent R I The first atom aI in the ligand L A The ligand L is the farthest from the metal M among all the atoms in B (if present) has a second substituent R II , where the second substituent R II The first atom a-II in the ligand L B The ligand L is the farthest from the metal M among all the atoms in C (if present) has a third substituent R III , where the third substituent R III The first atom a-III in the ligand L C It is the farthest from the metal M among all the atoms in the atom.

[0364] In such heteroleptic compounds, the vector V can be defined as follows D1 、V D2 and V D3 . V D1 represents the direction from the metal M to the first atom aI, and the vector V D1 The value of D 1 Represents the metal M and the first substituent R I The straight-line distance between the first atom aI in V D2 represents the direction from the metal M to the first atom a-II, and the vector V D2 The value of D 2 Represents the metal M and the second substituent R II The straight-line distance between the first atom a-II in V D3 represents the direction from the metal M to the first atom a-III, and the vector V D3 The value of D 3 Represents the metal M and the third substituent R III The straight-line distance between the first atoms a-III in .

[0365] In such heteroleptic compounds, a sphere with radius r is defined, the center of which is the metal M and the radius r is the radius that allows the sphere to enclose the non-substituents R in the compound. I , R II and R III is the smallest radius of all atoms that are part of 1 , D 2 and D 3 At least one of them is larger than the radius r by at least In some embodiments, D 1 , D2 and D 3 At least one of the following is greater than the radius r by at least 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 At least two of the radius r are at least 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 more greater than the radius r.

[0366] In some embodiments of such heteroleptic compounds, the compound has a transition dipole moment axis and the transition dipole moment axis is aligned with the vector V D1 、V D2 and V D3 The angle between the transition dipole moment axis and the vector V is defined as D1 、V D2 and V D3 At least one angle between the transition dipole moment axis and the vector V is less than 40°. D1 、V D2 and V D3 At least one angle between the transition dipole moment axis and the vector V is less than 30°, 20°, 15°, or 10°. D1 、V D2 and V D3 At least two angles between the transition dipole moment axis and the vector V are less than 20°. D1 、V D2 and V D3 At least two of the angles therebetween are smaller than 15° or 10°.

[0367] In some embodiments, the transition dipole moment axis is aligned with the vector V D1 、V D2 and V D3 All three 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 angles between are less than 15° or 10°.

[0368] 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.

[0369] A person skilled in the art will readily understand the meaning of the terms transition dipole moment axis of a compound and vertical dipole ratio of a compound. However, the meaning of these terms can be found in U.S. Pat. No. 10,672,997, the disclosure of which is incorporated herein by reference in its entirety. In U.S. Pat. No. 10,672,997, the horizontal dipole ratio (HDR) of a compound is discussed instead of VDR. However, a person skilled in the art will readily understand that VDR=1-HDR.

[0370] In some embodiments, the compound can be an emitting dopant. In some embodiments, the compound can generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence, triplet-triplet elimination or a combination of these methods. In some embodiments, the emitting 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 current compound relates to a mixture of various isomers of individual isomers and any mixing ratio. In some embodiments, the compound can be homogeneous (each ligand is the same). In some embodiments, the compound can be mixed (at least one ligand is different from the others). In some embodiments, when there is more than one ligand coordinated to the metal, the ligands can be all the same. In some other embodiments, at least one ligand is different from other ligands. In some embodiments, each ligand can be different from all other ligands. This is also true in the following embodiments, that is, the ligand coordinated to the metal can be connected to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate or hexadentate ligand. Thus, where coordinating ligands are linked together, in some embodiments all of the ligands may be identical, and in some other embodiments at least one of the linked ligands may be different from the other ligands.

[0371] In yet another aspect of the present disclosure, a formulation comprising the novel compounds disclosed herein is described. The formulation may include one or more components disclosed herein selected from the group consisting of: a solvent, an emitter, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material.

[0372] The present disclosure encompasses any chemical structure comprising a novel compound of the present disclosure or a monovalent or multivalent variant thereof. In other words, the compounds of the present invention 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, "monovalent variants of a compound" refers to the same part as the compound, but one of the hydrogens has been removed and replaced with a bond to the rest of the chemical structure. As used herein, "multivalent variants of a compound" refers to the same part as the compound, but more than one hydrogen has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecules, the compounds of the present invention can also be incorporated into supramolecular complexes without covalent bonds. As used in this context, the description that structure A includes part B means that structure A includes the structure of part B, and the structure of part B does not include H or D atoms that can be connected to part B. This is because at least one H or D on a given part structure must be replaced with a substituent so that part B can be a part of structure A, and after it becomes a part of structure A, one or more of the H or D on a given part B structure can be further substituted.

[0373] C. OLEDs and Devices of the Present Disclosure

[0374] In another aspect, the present disclosure also provides an OLED device comprising a first organic layer containing a compound as disclosed in the above compound section of the present disclosure.

[0375] In some embodiments, an OLED comprises: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a first ligand L having a structure comprising Formula I A of compounds.

[0376] 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 may be an emissive layer and the compound as described herein may be an emissive dopant or a non-emissive dopant.

[0377] In some embodiments, the organic layer may further include a host, wherein the host includes at least one chemical group selected from the group consisting of triphenylene, carbazole, indolecarbazole, 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).

[0378] In some embodiments, the subject can be selected from the group consisting of the following structures in subject group 1:

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388] in:

[0389] J 1 To J 6 Each of is independently C or N;

[0390] L' is a direct bond or an organic linking group;

[0391] Each Y AA , Y BB , Y CC and Y DDindependently selected from the group consisting of: absence of bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0392] R A' , R B' , R C' , R D' , R E' , R F' and R G' Each of independently represents mono-substitution, up to maximum substitution, or no substitution;

[0393] 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;

[0394] Also, where possible, each unsubstituted aromatic carbon atom is optionally replaced with one or more N to form an aza-substituted ring.

[0395] In some embodiments, J 1 To J 3 At least one of is N. In some embodiments, J 1 To J 3 At least two of are N. In some embodiments, J 1 To J 3 All three of are N. In some embodiments, each Y CC and Y DD is 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.

[0396] 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, wherein 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:

[0397]

[0398]

[0399] The structures of MG1 to MG27 are shown below:

[0400] In the MGb structures shown above, the two bonding positions in the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are labeled with numbers for identification purposes.

[0401] In some embodiments, the host can be any of its aza-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the host has the formula EGa-MGb-Egc and is selected from the group consisting of h1 to h112 as defined in the following List of Host Group 2, wherein each of MGb, EGa, and EGc is defined as follows:

[0402]

[0403]

[0404] In the table above, EGa and EGc structures bonded to one of the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are annotated with a numerical prefix identifying its bonding position in the MGb structure.

[0405] In some embodiments, the organic layer may further include a host, wherein the host includes a metal complex.

[0406] In some embodiments, the emission layer may include two main bodies: a first main body and a second main body. In some embodiments, the first main body is a hole transport main body, and the second main body is an electron transport main body. In some embodiments, the first main body is a hole transport main body, and the second main body is a bipolar main body. In some embodiments, the first main body is an electron transport main body, and the second main body is a bipolar main body. In some embodiments, the first main body and the second main body may form an exciplex. In some embodiments, the emission layer may include a third main body. In some embodiments, the third main body is selected from the group consisting of: an insulating main body (wide bandgap main body), a hole transport main body, and an electron transport main body. In some embodiments, the third main body forms an exciplex with one of the first main body and the second main body or with both the first main body and the second main body. In some embodiments, the emission layer may include a fourth main body. In some embodiments, the fourth main body is selected from the group consisting of: an insulating main body (wide bandgap main body), a hole transport main body, and an electron transport main body. In some embodiments, the fourth main body forms an exciplex with one of the first main body, the second main body, and the third main body, with both of the first main body, the second main body, and the third main body, or with each of the first main body, the second main body, and the third main body. In some embodiments, the LUMO of the electron transport subject is less than -2.4eV, less than -2.5eV, less than -2.6eV or less than -2.7eV. In some embodiments, the HOMO of the hole transport subject is higher than -5.6eV, higher than -5.5eV, higher than -5.4eV or higher than -5.35eV. HOMO and LUMO values ​​can be determined using solution electrochemistry. Solution cyclic voltammetry and differential pulse voltammetry can be performed using a CH instrument model 6201B potentiostat, using anhydrous dimethylformamide (DMF) solvent and tetrabutylammonium hexafluorophosphate as supporting electrolytes. Glassy carbon, platinum wire and silver wire are used as 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 the internal ferrocene-ferrocene salt 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 RF; Bassler H.; Porsch M.) M.); Daub, J. Adv. Mater. 1995, 7, 551), the corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were determined by comparing the cation and anion redox potentials with those of a ferrocene reference (4.8 eV relative to vacuum).

[0407] In some embodiments, the compounds as described herein may be sensitizers or components of sensitizers; wherein the device may further comprise an acceptor that receives energy from the sensitizer. In some embodiments, the acceptor is an emitter in the device. In some embodiments, the acceptor may be a fluorescent material. In some embodiments, the compounds described herein may be used as phosphorescent sensitizers in OLEDs, wherein one or more layers in the OLED contain an acceptor in the form of one or more non-delayed fluorescent and / or delayed fluorescent materials. In some embodiments, the compounds described herein may be used as a component of an excited complex used as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the acceptor and the acceptor will emit energy or further transfer energy to the final emitter. The acceptor concentration may be in the range of 0.001% to 99.9%. The acceptor may be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a thermally activated delayed fluorescent (TADF) material. In some embodiments, the acceptor is a non-delayed fluorescent material. In some embodiments, emission may be generated by any one or all of the sensitizer, the acceptor, and the final emitter. In some embodiments, the emission of the acceptor 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. Narrower FWHM means better color purity for OLED display applications.

[0408] As used herein, phosphorescence generally refers to the emission of photons when the electron spin quantum number changes, that is, the initial and final states of the emission have different electron spin quantum numbers, such as from T1 to S0 state. Most of the Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, if the excited complex formation involves a triplet emitter, such excited complexes can also emit phosphorescence. On the other hand, a fluorescent emitter generally refers to the emission of photons when the electron spin quantum number does not change, such as from S1 to S0 state, or from D1 to D0 state. Fluorescent emitters can be delayed fluorescent or non-delayed fluorescent emitters. Depending on the spin state, the fluorescent emitter can be a singlet emitter or a doublet emitter or other multiplet emitter. 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 produced by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the thermal population between the triplet and singlet excited states. Thermal energy can activate the triplet transition back to the singlet state. This type of delayed fluorescence is also known 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 small singlet-triplet energy gap (ΔE) of less than or equal to 400, 350, 300, 250, 200, 150, 100 or 50 meV. S-T ) compounds or excited complexes. There are two main types of TADF emitters, one is called donor-acceptor type TADF and the other is called multi-resonance (MR) TADF. Typically, a single compound donor-acceptor TADF compound is constructed by connecting an electron donor portion (such as an amino or carbazole derivative) and an electron acceptor portion (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). A donor-acceptor excited complex can be formed between a hole transport compound and an electron transport compound. Examples of MR-TADF materials include highly conjugated fused ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials may also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 of delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, such time may be greater than 10 microseconds and less than 100 microseconds.

[0409] In some embodiments, the OLED may include additional compounds selected from the group consisting of: non-delayed fluorescent materials, delayed fluorescent materials, phosphorescent materials, and combinations thereof.

[0410] In some embodiments, the compounds of the invention described herein are phosphorescent materials.

[0411] 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 energy transfers its excited state 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 comprises an acceptor. In some embodiments, the phosphorescent material forms an exciplex with another material (e.g., a host material, an emitter material) within the OLED.

[0412] In some embodiments, the non-delayed fluorescent material or delayed fluorescent material is an emitter that emits light in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material does not emit light in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material energy transfers its excited state to another material in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material participates in charge transport in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material is an acceptor, and the OLED further comprises a sensitizer.

[0413] In some embodiments of the OLED, the delayed fluorescent material comprises at least one donor group and at least one acceptor 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 called metal-assisted (MA) TADF). In some embodiments, the metal-assisted delayed fluorescent material comprises a metal-carbenium bond. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material comprises at least one chemical group selected from the group consisting of: aryl-amine, aryloxy, arylthio, triphenylene, carbazole, indolecarbazole, 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 -diaza-13b-borazinnaphtho[2,3,4-de]anthracene, 5-oxa-9λ 2-aza-13b-borazinnaphtho[3,2,1-de]anthracene, azacyclohexaborane, oxaborin, dihydroacridine, xanthracene, dihydrobenzazasilane, dibenzooxasilane, phenoxazine, phenoxathiol, phenothiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrol, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, amino, silane, aza variants thereof, and combinations thereof. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material comprises tri(aryl / heteroaryl)borane, wherein one or more pairs of substituents from aryl / heteroaryl groups 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, phenanthracene, phenanthracene, fluorene, pyrene, Perylene and Azulene.

[0414] In yet another aspect, the OLED of the present disclosure may further comprise an emissive region containing a compound or formulation of compounds as disclosed in the above compound section of the present disclosure. In some embodiments, the emissive region may comprise a first ligand L having a structure comprising Formula I A In some embodiments, the emissive region is composed 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 found in U.S. Patent Application Publication No. 2023 / 0292605, and the entire contents are incorporated herein by reference. In some embodiments, at least one of the one or more organic layers comprises a compound or formulation of a compound as disclosed in Sections A and D of the present disclosure.

[0415] In some embodiments, the OLED or emission region comprising 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, which includes a first emission region. The second sub-pixel includes a second OLED, which includes a second emission region. In some embodiments, the first and / or second OLED, the first and / or second emission regions may be the same or different and each may 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.

[0416] In some embodiments, the first emission region is configured to emit a wavelength having a peak wavelength λ max1 The second emission region is configured to emit light having a peak wavelength λ max2 In some embodiments, the peak wavelength λ max1 With λ max2 The difference between is at least 4 nm but within the same color. For example, light blue and dark blue light as described above. In some embodiments, the first emission region is configured to emit a light having a peak wavelength λ in one region of the visible spectrum of 400-500 nm, 500-600 nm, 600-700 nm. max1 and the second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum of 400-500nm, 500-600nm, 600-700nm max2 light. In some embodiments, the first emission region comprises (if more than one) a first number of emission layers deposited one on top of the other; and the second emission region comprises (if more than one) a second number of emission layers deposited one on top of the other; and the first number is different from the second number. In some embodiments, both the first emission region and the second emission region comprise phosphorescent materials, which may be the same or different. In some embodiments, the first emission region comprises a phosphorescent material and the second emission region comprises a fluorescent material. In some embodiments, both the first emission region and the second emission region comprise fluorescent materials, which may be the same or different.

[0417] In some embodiments, at least one pixel of an OLED or an emissive region comprises a total of N subpixels; wherein the N subpixels comprise a first subpixel and a second subpixel; wherein each of the N subpixels comprises an emissive region; wherein the total number of emissive regions within at least one pixel is equal to or less than N-1. In some embodiments, the second emissive region is identical to the first emissive region; and each subpixel of at least one pixel comprises an emissive region that is identical to the first emissive region. In some embodiments, a full-color pixel arrangement may have a plurality of pixels comprising a first pixel region and a second pixel region; wherein at least one display feature in the first pixel region is different from a corresponding display feature in the second pixel region, and wherein at least one display feature is selected from the group consisting of: resolution, cavity mode, color, outcoupling, and color filter.

[0418] In some embodiments, the OLED is a stacked OLED comprising one or more charge generation layers (CGLs). In some embodiments, the OLED comprises 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 features 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 stacked OLED comprises a sensitizer and an acceptor having various sensitizing device features and various embodiments of the compounds of the present invention disclosed herein. For example, the first emission region is included in the sensitizing device, while the second emission region is not included in the sensitizing device; in some cases, both the first emission region and the second emission region are included in the sensitizing device.

[0419] In some embodiments, the OLED can emit light having at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99% or 100% from a plasmon mode. In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emission layer is used as an enhancement layer. The enhancement layer comprises a plasmon material exhibiting a surface plasmon resonance, the plasmon material non-radiatively couples to the emitter material, and transfers excited state energy from the emitter material to a non-radiative mode of a surface plasmon polariton. In some embodiments, the enhancement layer is disposed at a distance from the organic emission layer that does not exceed a threshold distance, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer. 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 emitting material in the absence of the enhancement layer.

[0420] In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on a side above the enhancement layer opposite to the organic emission layer. The outcoupling layer scatters energy from surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, energy is scattered from the surface plasmon mode of the device into other modes, such as but not limited to an organic waveguide mode, a substrate mode, or another waveguide mode. In some embodiments, one or more intermediate layers may be disposed between the enhancement layer and the outcoupling layer. Examples of intermediate layers may be dielectric materials, including organic, inorganic, perovskite, oxides, and may include stacks and / or mixtures of these materials.

[0421] The enhancement layer changes the effective properties of the medium in which the emitter material resides, causing any or all of the following: reduced emissivity, changed emission line shape, variation in emission intensity with angle, changed emitter material stability, changed OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both, or placing the enhancement layer itself as a CGL, produces 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 OLED according to the present disclosure may also include any other functional layers commonly found in OLEDs.

[0422] In some embodiments, the enhancement layer may include 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: 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 configured as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or has sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged.

[0423] In some embodiments, the outcoupling layer has wavelength-sized features or sub-wavelength-sized features that are arranged periodically, quasi-periodically, or randomly. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles. In some embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the outcoupling layer may be adjusted by at least one of: 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 may be formed of at least one of: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layering of one or more materials, and / or a core of one type of material and coated with a shell of another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the outcoupling layer is formed by photolithography.

[0424] In some embodiments of plasmonic devices, the emitter and / or host compound used in the emissive 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.

[0425] In yet another aspect, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound or a formulation of compounds as disclosed in the above compound section of the present disclosure.

[0426] In some embodiments, a consumer product comprises an OLED having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a first ligand L having a structure comprising Formula I A of compounds.

[0427] In general, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When an electric 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 oppositely charged electrode. When electrons and holes are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair with 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 excited complex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0428] Figure 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. The device 100 may 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 blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 can be manufactured by depositing the layers in sequence. The properties and functions of these various layers and example materials are described in more detail in US 7,279,704, columns 6-10, which are incorporated by reference.

[0429] More examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is one doped with F at a molar ratio of 50:1. 4-TCNQ m-MTDATA, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of luminescent and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal (e.g., Mg:Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0430] Figure 2 An inverted OLED 200 is shown. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 can be manufactured by depositing the layers in order. Because the most common OLED configuration has a cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 An example is provided of how some layers may be omitted from the structure of device 100 .

[0431] Figure 1 and 2The simple layered structures described in are provided by way of non-limiting examples, and it should be understood that embodiments of the present disclosure may be used in conjunction with various 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 entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than the specifically described materials may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it should be understood that a combination of materials may be used, such as a mixture of a host and a dopant, or more generally, a mixture. In addition, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, the 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, for example, Figure 1 and 2 Multiple layers of said different organic materials.

[0432] Structures and materials not specifically described may also be used, such as OLEDs containing polymeric materials (PLEDs), such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of another example, an OLED having a single organic layer may be used. OLEDs may be stacked, such as described in U.S. Pat. No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from Figure 1 and 2 For example, the substrate may include angled reflective surfaces to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and / or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0433] Unless otherwise specified, any of the layers of the various embodiments may 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, 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., incorporated by reference in their entirety), and deposition by organic vapor jet printing (OVJP, also referred to as organic vapor jet deposition (OVJD)) (as described in U.S. Pat. No. 7,431,968, incorporated by reference in their 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 may also be used. The material to be deposited may be modified to make it compatible with a specific deposition method. For example, branched or unbranched, preferably containing at least 3 carbons, such as alkyl and aryl substituents, may be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 or more carbons may be used, and 3 to 20 carbons are a preferred range. Materials having asymmetric structures may have better solution processability than materials having symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0434] The device manufactured according to the embodiments of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrode and the organic layer from being exposed to harmful substances in an environment including moisture, steam and / or gas. The barrier layer can be deposited on a substrate, an electrode, under a substrate, an electrode, or next to a substrate, an electrode, or on any other part of the device (including the edge). The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques, and may include a composition having a single phase and a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may be combined with an inorganic compound or an organic compound or both. Preferred barrier layers include multiple alternate layers of the following materials: polymeric materials and non-polymeric materials; organic materials and inorganic materials; or a mixture 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.

[0435] The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of electronic component modules (or units), which can be incorporated into a variety of electronic products or intermediate components. Examples of the electronic products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels), etc. that can be utilized by end-user product manufacturers. The electronic component module may optionally include driving electronic devices and / or power supplies. The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of consumer products, and the consumer products have one or more electronic component modules (or units) incorporated therein. A consumer product comprising an OLED is disclosed, and the OLED includes a compound of the present disclosure in an organic layer in the OLED. The consumer product should include any kind of product containing one or more light sources and / or some type of visual display. Some examples of consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, phones, cellular phones, tablet computers, tablet phones, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices, and signage. Various control mechanisms can be used to control devices manufactured according to the present disclosure, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18°C ​​to 30°C, and more preferably at room temperature (20-25°C), but can be used outside this temperature range (e.g., -40°C to +80°C).

[0436] More details regarding OLEDs and the definitions set forth above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0437] 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.

[0438] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes. In some embodiments, the OLED further comprises one or more quantum dots. Such quantum dots can be in the emission layer, or in other functional layers, such as downconversion layers.

[0439] In some embodiments, the OLED comprises 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 having a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of ​​at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0440] D. Other materials used in OLED

[0441] The materials described herein are various examples of specific layers that can be used in OLEDs. They 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 EML, or in combination with a wide variety of other emitters, hosts, transport layers, barrier 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.

[0442] a) Conductive dopants:

[0443] The charge transport layer can be doped with a conductivity dopant to substantially change its charge carrier density, which in turn will change its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductivity dopant, and an n-type conductivity dopant is used in the electron transport layer. In some embodiments, the conductive dopant comprises at least one chemical moiety selected from the group consisting of: a cyano group, a fluorinated aryl or heteroaryl group, a fluorinated alkyl or cycloalkyl group, an alkylene group, a heteroaryl group, an amide, a benzodithiophene, and a highly conjugated heteroaryl group extended by a non-cyclic double bond.

[0444] b)HIL / HTL:

[0445] The hole injection / transport material used in the present disclosure is not particularly limited, and any compound can be used as long as the compound is generally used as a hole injection / transport material. Examples of the material include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolecarbazole derivatives; polymers containing fluorocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x ; p-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile; metal complexes; and crosslinkable compounds.

[0446] Examples of aromatic amine derivatives for use in HIL or HTL include, but are not limited to, the following general structure:

[0447]

[0448] Ar 1 To Ar 9 Each of the following is selected from the group consisting of aromatic hydrocarbon cyclic compounds: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; a 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, naphthridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units, which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are directly or via at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups. Ar 1 To Ar 9 Each of may be unsubstituted or may be substituted with general substituents as described above, and any two substituents may be joined or fused to form a ring.

[0449] In some embodiments, each Ar 1 To Ar 9 independently comprising a portion selected from the group consisting of:

[0450]

[0451] 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.

[0452] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0453] Where Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 The coordinating atoms of L are independently selected from C, N, O, P and S; 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.

[0454] In some embodiments, (Y 101 -Y 102 ) is a 2-phenylpyridine or 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 relative + / Fc coupling has a minimum oxidation potential in solution of less than about 0.6 V.

[0455] In some embodiments, the HIL / HTL material is selected from the group consisting of phthalocyanine and porphyrin compounds, starburst triarylamines, CF x Fluorocarbon polymers, conductive polymers (e.g., PEDOT:PSS, polyaniline, polythiophene), phosphonic acid and silane SAMs, triarylamine or polythiophene polymers containing conductive dopants, organic compounds containing conductive inorganic compounds (such as molybdenum oxide and tungsten oxide), n-type semiconductive organic complexes, metal organic metal complexes, crosslinkable compounds, polymers and copolymers based on polythiophene, triarylamines, triarylamines containing spirofluorene cores, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indolecarbazoles, isoindole compounds and metal carbene complexes.

[0456] c) EBL:

[0457] 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 produce substantially higher efficiency and / or longer lifetimes than similar devices lacking a blocking layer. In addition, a blocking layer can be used to confine emission to a desired area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more 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 energy level of the compound used in the EBL is shallower than the HOMO energy level 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 used in one of the hosts described below.

[0458] d) Subject:

[0459] 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 may be used as long as the host does not completely quench the emission of the dopant.

[0460] Examples of metal complexes used as hosts preferably have the following general formula:

[0461]

[0462] Where Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 The coordinating atoms of L are independently selected from C, N, O, P and S; 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.

[0463] In some embodiments, the metal complex is:

[0464]

[0465] wherein (ON) is a bidentate ligand having a metal coordinated to O and N atoms.

[0466] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0467] In some embodiments, the host compound contains at least one selected from the following group: a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, Oxadiazine, indole, benzimidazole, indazole, indoxazines, 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-indolcarbazole, aza-triphenylene, aza-tetraphenylene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-borazinnaphtho[3,2,1-de]anthracene; and a group consisting of 2 to 10 cyclic structural units, which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are directly or via at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups. Each option within each group may be unsubstituted or may be substituted with a general substituent as described herein or may be further condensed.

[0468] In some embodiments, the host compound comprises at least one moiety selected from the group consisting of:

[0469]

[0470] Where k is an integer from 0 to 20 or from 1 to 20. 101 To X 108 Z is independently selected from C or N. 101 and Z 102 are independently selected from C, N, O or S.

[0471] In some embodiments, the host material is selected from the group consisting of: aryl carbazoles, metal 8-hydroxyquinolinates (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic fused rings, zinc complexes, Compounds, aryltriphenylene compounds, poly-fused heteroaryl compounds, donor-acceptor molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., PVK), spirofluorene compounds, spirofluorene-carbazole compounds, indolecarbazole, 5-membered electron-deficient heterocycles (e.g., triazole, oxadiazole), tetraphenylene complexes, metal phenoxypyridine compounds, metal coordination complexes (e.g., Zn, Al containing N^N ligands), dibenzothiophene / dibenzofuran-carbazole compounds, silicon / germanium aromatic compounds, aromatic benzoyl esters, carbazoles connected by non-conjugated groups, aza-carbazole / dibenzofuran / dibenzothiophene compounds and high triplet metal organic metal complexes (e.g., metal-carbene complexes).

[0472] e) Emitter materials in EML:

[0473] One or more emitter materials may be used in combination with the compounds or devices disclosed herein. The emitter material may be emissive or non-emissive in the current device as described herein. Examples of emitter materials are not particularly limited, and any compound may be used as long as the compound is capable of producing 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.

[0474] In some embodiments, the emitter material has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0475] Where L 1 , L 2 and L 3 Can be the same or different;

[0476] where x is 1, 2, or 3;

[0477] Where y is 0, 1 or 2;

[0478] where z is 0, 1 or 2;

[0479] Wherein x+y+z is the oxidation state of the metal M;

[0480] Where L 1 Selected from the group consisting of structures in the following ligand list:

[0481]

[0482]

[0483] Each L 2 and L 3 Independently choose freedom and a group consisting of structures in the ligand list; where:

[0484] M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag and Cu;

[0485] T is selected from the group consisting of B, Al, Ga and In;

[0486] K 1 ' is a direct key or is selected from the group consisting of: NR e , PR e , O, S and Se;

[0487] Each Y 1 To Y 15 independently selected from the group consisting of carbon and nitrogen;

[0488] Y'Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO 2 , CR e R f 、SiR e R f and GeR e R f ;

[0489] Each R a , R b , R c and R d can independently represent monosubstitution to the maximum possible number of substitutions or no substitution;

[0490] 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 general substituents as defined herein; and

[0491] Any two of the substituents may be fused or joined to form a ring or to form a polydentate ligand.

[0492] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 1:

[0493]

[0494]

[0495]

[0496]

[0497] in

[0498] X 96 To X 99 Each of is independently C or N;

[0499] Each Y 100 Independently selected from the group consisting of NR", O, S and Se;

[0500] R 10a , R 20a , R 30a , R 40a and R 50a Each of independently represents mono-substitution, up to maximum substitution, or no substitution;

[0501] 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 Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; any two substituents may be joined or fused to form a ring.

[0502] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 2:

[0503]

[0504]

[0505]

[0506]

[0507] in:

[0508] Each Y 100 Independently selected from the group consisting of NR", O, S and Se;

[0509] L is independently selected from the group consisting of: direct bond, BR", BR"R"', NR", PR", O, S, Se, C=O, C=S, C=Se, C=NR", C=CR"R"', S=O, SO 2 , CR", CR"R"', SiR"R"', GeR"R"', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof;

[0510] X 100 and X 200 at each occurrence selected from the group consisting of: O, S, Se, NR" and CR"R"';

[0511] Each R A" , R B" , R C" , R D" , R E" and R F" independently represents mono-substitution, up to maximum substitution, or no substitution;

[0512] 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 of is independently hydrogen or a substituent selected from the group consisting of general substituents as defined herein; and any two substituents may be joined or fused to form a ring.

[0513] In some embodiments of dopant groups 1 and 2 above, each unsubstituted aromatic carbon atom may be replaced by N to form a nitrogen heterocycle. In some embodiments, the maximum number of N atoms in one ring is 1 or 2. In some embodiments of dopant group 2 above, each Pt atom in the formula may be replaced by a Pd atom.

[0514] In some embodiments of the OLED, the delayed fluorescent material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescent material is a metal complex. In some embodiments, the delayed fluorescent material is a non-metallic complex. In some embodiments, the delayed fluorescent material is a Zn, Cu, Ag or Au complex.

[0515] In some embodiments of OLEDs, the delayed fluorescent material has the formula M(L 5 )(L 6 ), where M is Cu, Ag or Au, L 5 and L 6 Different, and L 5 and L 6 Independently selected from the group consisting of:

[0516]

[0517]

[0518] Among them A 1 -A 9 are each independently selected from C or N;

[0519] Each R P , R Q and R U independently represents mono-substitution, up to maximum substitution, or no substitution;

[0520] 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 consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0521] In some embodiments of the OLED, the delayed fluorescent material comprises at least one of the donor moieties selected from the group consisting of:

[0522]

[0523] where Y T , Y U , Y V and Y WEach independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO 2 .

[0524] In some of the above embodiments, any carbon ring atom up to a total of up to three carbon ring atoms together with their substituents in each benzene ring of any of the above structures can be replaced by N.

[0525] In some embodiments, the delayed fluorescent material comprises at least one of an acceptor moiety 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 linked, via a conjugated linker or a non-conjugated linker (such as sp 3 carbon or silicon atoms).

[0526] In some embodiments, the fluorescent material comprises at least one of the chemical moieties selected from the group consisting of:

[0527]

[0528]

[0529] where Y F , Y G , Y H and Y I Each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO 2 ;

[0530] Where X F and X G are each independently selected from the group consisting of C and N.

[0531] In some of the above embodiments, any carbon ring atom up to a total of up to three carbon ring atoms together with their substituents in each benzene ring of any of the above structures can be replaced by N.

[0532] f)HBL:

[0533] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in substantially higher efficiency and / or longer lifetime than a similar device lacking the blocking layer. In addition, a blocking layer can be used to confine emission to desired areas of the OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than one or more of the emitters closest to the HBL interface.

[0534] In some embodiments, the compounds used in HBL contain the same molecules or the same functional groups as used in the subjects described above.

[0535] In some embodiments, the compound used in HBL comprises at least one of the following moieties selected from the group consisting of:

[0536] Where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0537] g)ETL:

[0538] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.

[0539] In some embodiments, the compounds used in the ETL comprise at least one of the following moieties in the molecule: and fullerene; wherein k is an integer from 1 to 20, X 101 To X 108 Selected from C or N; Z 101 Selected from the group consisting of C, N, O and S.

[0540] In some embodiments, the metal complex used in the ETL contains but is not limited to the following general formula:

[0541]

[0542] wherein (ON) or (NN) is a bidentate ligand having a metal coordinated to 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 attached to the metal.

[0543] In some embodiments, the ETL material is selected from the group consisting of anthracene-benzimidazole compounds, azatriphenylene derivatives, anthracene-benzothiazole compounds, metal 8-hydroxyquinolinates, metal hydroxybenzoquinolinates, bathocuprine compounds, 5-membered electron-deficient heterocycles (e.g., triazole, oxadiazole, imidazole, benzimidazole), thiole compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0544] h) Charge Generation Layer (CGL)

[0545] In a tandem or stacked OLED, the CGL plays a fundamental role in the performance and consists 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 electrodes. The electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; then, the bipolar current gradually reaches a steady state. Typical CGL materials contain n- and p-conductivity dopants used in the transport layer.

[0546] In any compound disclosed herein, hydrogen atoms can be partially or completely 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 common meaning and includes the percentage of all possible hydrogens and deuterium atoms replaced by deuterium atoms. In certain embodiments, the deuterium atom is connected to an aromatic ring. In certain embodiments, the deuterium atom is connected to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atom is connected to a heteroatom, such as a Si or Ge atom.

[0547] 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 present invention. For example, other materials and structures may be used to replace many materials and structures described herein without departing from the spirit of the present invention. The present invention as required may therefore include variations of 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 about why the present invention works are not intended to be restrictive.

[0548] E. Experimental Data

[0549]

[0550] In a 200mL round-bottom flask, a dark yellow transparent solution of 7-(4-(tert-butyl)naphthalene-2-yl)-2-iodo-3-methylthieno[2,3-c]pyridine (3.000g, 6.559mmol) in anhydrous tetrahydrofuran (50mL) was cooled to -75°C in a dry ice-acetone bath under nitrogen. A hexane solution of n-BuLi (5.50mL, 1.600 moles, 8.855mmol) was added dropwise over 30 minutes. A gentle nitrogen flow was maintained. It was stirred at the same temperature for 1 hour and 20 minutes. A solution of 1-chloro-1,1,2,2,2-pentamethyldisilane (1.97mL, 10.17mmol) in anhydrous tetrahydrofuran (3.0mL) was prepared and added dropwise to the above solution over 10 minutes at the same temperature. A positive pressure of nitrogen was maintained. The mixture was slowly warmed to 20°C and stirred overnight (16 h). 4 The reaction mixture was quenched with aqueous Cl (50 mL), deionized water (20 mL), then diluted with EtOAc (20 mL) and stirred briefly to give two clear phases. The layers were separated and extracted repeatedly with EtOAc (50 mL). The combined organics were washed with MgSO 4 Drying, filtration and concentration in vacuo at 50°C afforded an off-white solid. Chromatography on silica using 0-3% EtOAc in heptane afforded a white solid 1.77 g (58%).

[0551]

[0552] 7-(4-(tert-butyl)naphthalen-2-yl)-3-methyl-2-(1,1,2,2,2-pentamethyldisilyl)thieno[2,3-c]pyridine (1.70 g, 2.2 Eq, 3.68 mmol), iridium chloride (0.590 g, 1 Eq, 1.67 mmol), 2-ethoxyethanol (45.00 mL) and water (15.00 mL) were added to a 125 mL 3-neck round bottom flask. Nitrogen was bubbled through the mixture and the mixture was heated to 105 ° C overnight under nitrogen. The reaction mixture was diluted with methanol, and the red solid was filtered off, washed with methanol and used in the next step without further purification.

[0553] To a 100 mL round bottom flask was added the product from the previous step (1.140 g, 1 Eq, 496.0 μmol), potassium (Z)-3,7-diethyl-6-oxonon-4-ene-4-olate (623.5 mg, 5 Eq, 2.480 mmol) and dichloromethane (34.00 mL). The reaction mixture was stirred at room temperature under nitrogen overnight. Diluted with dichloromethane and filtered through celite. The celite was washed with dichloromethane and the filtrate was evaporated to give a red solid. The residue was purified on a silica gel column to give 0.40 g (16%) of the product.

[0554]

[0555] 5-Bromo-2-chloropyridine reacts with nBuLi at 77K and quenches the reaction with 1-chloro-1,1,2,2,2-pentamethyldisilane to give 2-chloro-5-(1,1,2,2,2-pentamethyldisilyl)pyridine, which is then reacted with phenylboronic acid under Suzuki coupling reaction conditions to give 5-(1,1,2,2,2-pentamethyldisilyl)-2-phenylpyridine (L1). L1 reacts with IrCl3 to give Ir intermediate 1. It reacts with AgOTf to give Ir intermediate 2. Example 2 of the present invention can be prepared by reacting Ir intermediate 2 and L2 with a base.

[0556]

[0557] Inventive Example 3 can be prepared using L1 and L3 according to the above procedure.

[0558]

[0559] Example 4 of the present invention can be prepared using L1 and L4 according to the above procedure.

[0560]

[0561] Example 5 of the present invention can be prepared using LB3 and L5 according to the above procedure.

[0562] Device Examples

[0563] Through high vacuum (<10 -7 All example devices were fabricated by thermal evaporation using 200-1000 % MgCl2 (torr). The anode electrode was The cathode is made of indium tin oxide (ITO). Liq (8-hydroxyquinoline lithium) and thereafter All devices were prepared immediately after fabrication in a nitrogen glove box (<1 ppm H 2 O and O 2 ) is packaged with a glass lid sealed with epoxy resin, and a dehumidifier is incorporated into the package. The organic stack of the device example consists of the following in order from the ITO surface: LG101 (purchased from LG Chemical Co., Ltd.) as a hole injection layer (HIL); The HTM is used as the hole transport layer (HTL); The EBM acts as an electron blocking layer (EBL); an emissive layer (EML) containing RH as a red host and 3% emitter; and Liq (8-hydroxyquinoline lithium) doped with 35% ETM was used as the electron transport layer (ETL). Table 1 shows the thickness and materials of the device layers.

[0564] Table 1. Device layer materials and thicknesses

[0565]

[0566] The chemical structure of the device material is shown below:

[0567]

[0568] At the time of manufacture, the devices were tested for EL and JVL. For this purpose, the samples were powered by a 2-channel Keysight B2902A SMU at 10 mA / cm 2 The current density was energized and measured by a Photo Research PR735 spectroradiometer. The radiance (L) (W / str / cm 2 ) and total integrated photon counts. The device was then placed under a large area silicon photodiode for JVL scanning. The device was operated at 10 mA / cm 2 The integrated photon count under 0 is used to convert the photodiode current into photon counts. The scanning voltage is 0 to 200 mA / cm 2 The voltage of the device was calculated using total integrated photon counting. All results are summarized in Table 2. Voltage, EQE are reported as relative numbers normalized to the results of the comparative example.

[0569] Table 2.

[0570]

[0571] Table 2 summarizes the performance of the electroluminescent devices. The device of the present invention (Device 1) using the compound of the present invention as the emissive dopant exhibits a saturated red color (λmax=618 nm) compared to Device 2 using the comparative compound (λmax=611 nm). In addition, Device 1 exhibits a saturated red color (λmax=618 nm) compared to Device 2 at 10 mA / cm 2 The results show that the OLEDs of the present invention can be used as emissive dopants to improve the performance of OLED devices.

Claims

1. A compound having a first ligand L comprising a structure of Formula I A , in: Each of moiety A and moiety B is independently a monocyclic or polycyclic fused ring system, wherein each ring in the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; Z 1 To Z 4 Each of is independently C or N; K 1 and K 2 Each independently selected from the group consisting of: direct key, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ); L is selected from the group consisting of 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, CRR', SiRR' and GeRR'; R A and R B Each of the above independently represents mono-substitution to the maximum permissible substitution or no substitution; R A and R B At least one of them comprises a structure of Formula II, Each R, R', R 1 , R 2 , R 3 , R 4 , R 5 , R α , R β , R A and R B are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; X a and X b Each of is independently Si or Ge; L A coordinated to a metal M having an atomic mass of at least 40; M can coordinate with other ligands; L A Capable of combining with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; Any two substituents can be joined or fused to form a ring; The condition is L A Does not contain formula III Or Formula IV The structure of; and the compound is not:

2. The compound of claim 1, wherein each of moiety A and moiety B 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, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenol phenanthene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, aza-benzimidazole-derived carbene, naphtho-imidazole, aza-naphtho-imidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, phenanthro[3,2-b]benzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene and aza-fluorene.

3. The compound according to claim 1, wherein Z 1 is N and Z 4 is C, or Z 1 is carbene C and Z 4 is C; and / or where Z 2 and Z 3 is C; and / or K 1 is a direct bond, S or O; and / or wherein K 2 is a direct bond, S or O; and / or wherein L is a direct bond; and / or wherein at least one R A comprising a substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and combinations thereof; and / or wherein at least one R B comprising a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; and / or wherein the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu.

4. The compound according to claim 1, wherein for at least one structure of Formula II, X a is Si and X b is Si; and / or wherein R 1 To R 5 At least one of the following independently comprises a substituent selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof; and / or wherein X a or X b Bonded to part A or part B, or where X a or X b A direct bond is formed with either moiety A or moiety B, not via the dashed line of formula II.

5. The compound according to claim 1, wherein the structure of Formula II is linked by a direct bond or by an organic linking group L Y Bonded to either part A or part B.

6. The compound according to claim 1, wherein the ligand L A Select 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: direct key, NR e , PR e , O, S and Se; Y 1 To Y 23 Each of is independently selected from the group consisting of carbon and nitrogen; W 1 Selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR' and GeRR'; W 2 is B, N or P; Y' and Y" are selected from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO2,C=CR e R f 、C=NR e , CR e R f 、P(O)R e 、SiR e R f and GeR e R f ; Each R a , R b , R c and R d independently represents zero substitution, monosubstitution, or up to the maximum allowed number of substitutions on its associated ring; R, R', 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, boryl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; and Any two adjacent R, R', R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f Capable of condensing or joining to form a ring or to form a multidentate ligand.

7. The compound according to claim 1, wherein the ligand L A Select from the group consisting of: in: K 1 'Selected from the group consisting of: direct key, NR e , PR e , O, S and Se; Y 2 To Y 7 Each of is independently selected from the group consisting of carbon and nitrogen; W 1 Selected from the group consisting of: direct bond, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR' and GeRR'; Y' and Y" are selected from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,C=S,C=Se, S=O, SO2, C=CR e R f , C=NR e , CR e R f , P(O)R e , SiR e R f , and GeR e R f ; Each R a , R b , R c and R d independently represents zero substitution, monosubstitution, or up to the maximum allowed number of substitutions on its associated ring; R, R', 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, boryl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; and Any two adjacent R, R', R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f Capable of condensing or joining to form a ring or to form a multidentate ligand.

8. The compound according to claim 1, wherein the ligand L A Choose from L Ai -(R E )(R J )(R K )(R L ), where i is an integer from 1 to 256, R J , R K and R L Each of which is independently selected from R1 to R 150 The group is composed of E Choose from R E1 To R E94 The group consisting of L A1 (R E1 )(R1)(R1)(R1) to L A256 (R E94 )(R 150 )(R 150 )(R 150 ) is defined as follows: Where R E To R E94 Has the following structure: Where R1 to R 150 Has the following structure:

9. The compound according to claim 1, wherein the compound has the formula M(L A ) p (L B ) q (L C ) r , 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.

10. The compound of claim 9, wherein 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 where L A , L B and L C Different from each other; or formula Pt(L A )(L B ); and where L A and L B Can be the same or different.

11. The compound according to claim 9, 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 capable of being fused or joined to form a ring; Each R a , R b , R c and R d independently represents monosubstituted 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 can be fused or joined to form a ring or to form a multidentate ligand.

12. The compound according to claim 8, wherein the compound has the formula Ir(L A )3, Formula Ir(L A )(L Bk )2, Formula Ir(L A )2(L Bk ), formula Ir(L A )2(L Cj-I ) or formula Ir(L A )2(L Cj-II ), Where k is an integer from 1 to 530, and each L Bk Has the following structure: Where j is an integer from 1 to 1416, and each L Cj-I Has a structure based on the following formula: and Each L Cj-II Has a structure based on the following formula: For L Cj-I and L Cj-II Each L Cj , R 201 and R 202 As defined below: Where R D1 To R D246 Has the following structure:

13. The compound of claim 1, wherein the compound is selected from the group consisting of:

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

Images