Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. Provided is a compound comprising a first ligand LA of formula I '# imgabs 0 # # imgabs 1 #. In formula I'or formula I *, all variables are as defined herein; and LA is coordinated with the metal M. 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 U.S.C. §119(e) to U.S. Provisional Application Nos. 63 / 600,843 filed on November 20, 2023, 63 / 585,614 filed on September 27, 2023, and 63 / 514,698 filed on July 20, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates generally to organometallic compounds and formulations and various uses thereof, including as emitters in devices such as organic light emitting diodes and related electronic devices. Background Art

[0004] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly desirable. Many materials used to manufacture such devices are relatively inexpensive, so organic optoelectronic devices have the potential for 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, 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 phosphorescent emitting molecules is full-color displays. Industry standards for such displays require pixels suitable for emitting 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 well known in the art. Summary of the invention

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

[0008]

[0009] wherein moieties A, B, C, D and E0 are each independently a monocyclic or polycyclic fused ring system, wherein each ring in the monocyclic and polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0010] Where W 1 , W 2 , W 3 and W 4 Each independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR';

[0011] Where W 5 and W 6 Each independently selected from the group consisting of: BR, N, CR, SiR and GeR;

[0012] Where K 1 and K 2 Each of which is 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 );

[0013] K 1 and K 2 At least one of is a direct key;

[0014] R A , R B , R C , R D and R E0 Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0015] R, R', R α , R β , R A , R B , R C , R D and R E0 each independently is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof;

[0016] L A Coordinate with metal M;

[0017] M can coordinate with other ligands;

[0018] L A Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands;

[0019] wherein any two substituents may be joined or fused to form a ring; and

[0020] The compound is not

[0021] In another aspect, the present disclosure also provides a compound comprising a first ligand L of formula I* A* :

[0022]

[0023] wherein the moiety A* and the moiety B* are each 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;

[0024] Where Z 1* -Z 4* each independently is C or N;

[0025] Where R A* and R B* Each independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0026] Where 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 );

[0027] wherein L* is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CR'R", S=O, SO2, CRR', SiRR' and GeRR';

[0028] Where R α , R β , R, R', R A* and RB* each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof;

[0029] wherein any two substituents may be joined or fused to form a ring;

[0030] Where L A* Inclusive The structure of X1 to X 14 Each of is independently C or N; each R W represents monosubstituted to the maximum permissible substitution, or no substitution; and each R W are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; and any two R W may be optionally joined or fused to form a ring;

[0031] Where L A* coordinated to a metal M having an atomic mass of at least 40;

[0032] wherein the compound is a monometallic compound;

[0033] wherein the metal M can be coordinated with other ligands; and

[0034] Where L A* Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands;

[0035] In another aspect, the present disclosure provides a formulation containing a first ligand L comprising Formula I' or Formula I* as defined herein A of compounds.

[0036] In another aspect, the present disclosure provides an OLED having an organic layer comprising a first ligand L comprising formula I' or formula I* as defined herein A of compounds.

[0037] In another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer, the organic layer comprising a first ligand L comprising Formula I' or Formula I* as defined herein A of compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 An organic light emitting device is shown.

[0039] Figure 2 An inverted organic light-emitting device without a separate electron transport layer is shown. DETAILED DESCRIPTION

[0040] A. Terminology

[0041] Unless otherwise stated, the following terms used herein are defined as follows:

[0042] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "placed "above" a second layer, the first layer is placed 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 layer and the second layer. For example, a cathode may be described as being "placed "above" an anode, even though there are various organic layers between the two.

[0043] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium, either in solution or suspension form.

[0044] 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 (less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (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.

[0045] As used herein, and as will be generally understood by one skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are 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 in the downward direction from the vacuum level. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0046] 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 light of a particular color may include one or more emissive layers disposed on top of each other in a stacked manner.

[0047] 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.

[0048] In some arrangements, a color change layer is provided that converts, modifies or changes the color of light emitted by another layer to an emission having a different wavelength. The color change layer may be formulated to shift the wavelength of light emitted by another layer by a specified amount, the amount being 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 change layers: color filter layers 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" color filter layer to filter the input light to remove light with wavelengths outside the range of about 580-700nm. A "color" component refers to a component that, when activated or used, produces or otherwise emits light having a specific color as previously described. 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, when activated within the device, emit two different colors as previously described.

[0049] As used herein, emissive materials, layers, and regions may be different 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.

[0050] In some cases, it may be preferred to describe the color of a component (e.g., 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 within or near the edge of the "green" region and one within or near the edge of the "red" region, as previously described. Accordingly, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. A shape in the 1931 CIE color space is constructed by tracing the trajectory between two color points and any other internal points. For example, the internal shape parameters for red, green, blue, and yellow may be defined as follows:

[0051]

[0052] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0053] The term "acyl" refers to a substituted carbonyl (-C(O)-R s ).

[0054] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0055] The term "ether" refers to -OR s Group.

[0056] The terms "thio" or "thioether" are used interchangeably and refer to -SR s Group.

[0057] The term "selenoyl" refers to -SeR s Group.

[0058] The term "sulfinyl" refers to -S(O)-R s Group.

[0059] The term "sulfonyl" refers to -SO2-Rs Group.

[0060] 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 groups, wherein each R s Can be the same or different.

[0061] The term "silyl group" refers to a group containing at least one silicon atom bonded to the structure of interest. Common examples of silyl groups include, but are not limited to, -Si(R s )3 groups, wherein each R s Can be the same or different.

[0062] 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 groups, wherein each R s Can be the same or different.

[0063] The term "boryl" refers to a group containing at least one boron atom bonded to a related structure. Common examples of boryl groups include, but are not limited to, -B(R s )2 group or its Lewis adduct -B(R s )3 groups, wherein R s Can be the same or different.

[0064] In each of the above, R s It may be hydrogen or a substituent selected from the group consisting of general substituents defined in the present 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.

[0065] 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.

[0066] 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.

[0067] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group having at least one carbon atom replaced by a heteroatom, respectively. 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.

[0068] 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 from the carbon-carbon double bond is bonded to a related structure. Cycloalkenyl is essentially a cycloalkyl group including at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, 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.

[0069] 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 from the carbon-carbon triple bond is bonded to the associated structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, alkynyl groups may be further substituted.

[0070] 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.

[0071] 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.

[0072] The term "aryl" refers to and includes both monocyclic and polycyclic aromatic hydrocarbon groups. Polycyclic rings may have two or more rings, wherein two carbons are common to two adjacent rings (the rings are "fused"). Preferred aryl groups are aryl groups 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 with 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, chrysene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene and naphthalene. In addition, aryl groups may be further substituted or fused, such as but not limited to fluorene.

[0073] 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. Heteropolycyclic aromatic 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, benzo imidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, dibenzopyran, 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.

[0074] 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 each of their corresponding aza analogs are of particular interest.

[0075] 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0076] In some cases, preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0077] In some cases, more preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, aryl, heteroaryl, nitrile, thio, and combinations thereof.

[0078] 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.

[0079] In still other cases, the most preferred universal substituents are selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0080] The terms "substituted" and "substituted" refer to the bonding of a substituent other than H to the relevant position, such as carbon or nitrogen. For example, when R 1 When it represents a single substitution, then 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 substitution or no substitution, R 1 This can be, for example, hydrogen with available valences for the ring atoms, such as the carbon atoms of benzene and the nitrogen atoms in pyrrole, or simply none for ring atoms with full 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.

[0081] As used herein, "combinations thereof" means that one or more members of the applicable list are combined to form known or chemically stable arrangements that can be envisioned by a person of ordinary skill in the art from the applicable list. For example, alkyl groups can be combined with deuterium to form partially or fully deuterated alkyl groups; halogens can be combined with alkyl groups to form halogenated alkyl substituents; and halogens, alkyl groups, and aryls can be combined to form halogenated arylalkyl groups. In one case, the term substitution includes a combination of two to four of the listed groups. In another case, the term substitution includes a combination of two to three groups. In another case, the term substitution includes a combination of two groups. Preferred combinations of substituents are substituents containing up to fifty atoms that are not hydrogen or deuterium, or substituents including up to forty atoms that are not hydrogen or deuterium, or substituents 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.

[0082] The "aza" designations in the fragments described herein, i.e., azadibenzofuran, azadibenzothiophene, etc., mean that one or more CH groups in the respective aromatic rings may 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 encompassed by the term as set forth herein.

[0083] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US2011 / 0037057 (each of which is incorporated herein by reference in its entirety) describe the preparation of deuterium-substituted organometallic complexes. Reference is also 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 herein by reference in their entireties, which describe efficient pathways for deuteration of methylene hydrogens in benzylamines and replacement of aromatic ring hydrogens with deuterium, respectively.

[0084] As used herein, any specific listed substituents, such as but not limited to methyl, phenyl, pyridyl, etc., include their 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 whose valence is not 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 of is meant to include C6H6, C6D6, C6H3D3 and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, but are not limited to, CD3, CD2C(CH3)3, C(CD3)3 and C6D5.

[0085] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0086] 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).

[0087] B. Compounds of the Disclosure

[0088] Complexes with unique ligand structures and substitution features are described herein. The substitution patterns described herein improve material properties, including emission color, emission spectral line shape, alignment in emissive film layers, and improve OLED performance when the compounds are used as emissive dopants.

[0089] In one aspect, the present disclosure provides a compound comprising a first ligand L of formula I' A ,

[0090]

[0091] wherein moieties A, B, C, D and E0 are each independently a monocyclic or polycyclic fused ring system, wherein each ring in the monocyclic and polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0092] Where W 1 , W 2 , W 3 and W 4 Each independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR';

[0093] Where W 5 and W 6 Each independently selected from the group consisting of: BR, N, CR, SiR and GeR;

[0094] Where K 1 and K 2 Each of which is 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 );

[0095] K 1 and K 2 At least one of is a direct key;

[0096] R A , R B , R C , R D and R E0 Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0097] R, R', R α , R β , R A , R B , R C , R D and R E0 are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein;

[0098] L A Coordinate with metal M;

[0099] M can coordinate with other ligands;

[0100] L A Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands;

[0101] wherein any two substituents may be joined or fused to form a ring; and

[0102] The compound is not

[0103]

[0104] In some embodiments, when the moiety C is a 5-membered aromatic ring and the moiety A is a 6-membered or polycyclic ring, the two R C Do not join to form a ring. In some of these embodiments, portion B and / or portion D may or may not be present.

[0105] In some embodiments, when moiety C is a 5-membered non-aromatic ring, then moiety E0 is a polycyclic fused ring system.

[0106] In some embodiments, when moiety C is a 6-membered ring, then at least one of moiety A or moiety EO is a polycyclic fused ring system; and at least one of moiety B or D is present.

[0107] In some embodiments, the compound comprises a ligand L of Formula I'A A :

[0108]

[0109] In some embodiments, the compound comprises a ligand L of Formula I'B A :

[0110]

[0111] In some embodiments, the compound comprises a ligand L of Formula I'C A :

[0112]

[0113] In some embodiments, the compound comprises a ligand L of Formula I'D A :

[0114]

[0115] In some embodiments of Formula I', each of the moieties A, B (when present), C, D (when present), and EO are independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthridine, phenanthridine, and fluorene.

[0116] In some embodiments, the moiety C is pyrrole, furan, thiophene, selenophene, pyrazole, oxazole, thiazole, or imidazole. In some embodiments, the moiety A is pyridine, pyrimidine, quinoline, isoquinoline, furopyridine, or thienopyridine.

[0117] In some embodiments of Formula I', Z 1 is N and Z 2 is C. In some embodiments, Z 1 is C and Z 2 It is N.

[0118] In some embodiments of Formula I', W 1 To X 6 Each of is C. In some embodiments, W 1 To X 6 At least one of is N. In some embodiments, W 1 To W 4 At least one of is O, S or Se. In some embodiments, W 5 or W 6 At least one of is N.

[0119] In one aspect, the present disclosure provides a compound comprising a first ligand L of formula I A ,

[0120] In Formula I:

[0121] each of moiety C, moiety E, and (when present) moieties B and D is independently a monocyclic or polycyclic fused ring system, wherein each ring in the monocyclic and polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0122] The dashed arcs indicate that part B and part D are optionally present;

[0123] X 1 , X 2 , Z 1 and Z 2 Each of is independently C or N;

[0124] X 3 To X 6 Each of which is independently selected from the group consisting of: C, O, S, Se, N, P, Si, and Ge;

[0125] 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 );

[0126] K 1 and K 2 At least one of is a direct key;

[0127] Each independently represents a single bond or a double bond;

[0128] R A , R B , R C , R D and R E Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0129] R α , R β , 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;

[0130] L A Coordinate with metal M;

[0131] M can coordinate with other ligands;

[0132] L A Capable of combining with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands;

[0133] Any two substituents may be joined or fused to form a ring; and

[0134] Provided that the compound is not

[0135] In some embodiments of Formula I, if X 3 To X 6 If each of is carbon, then at least one of portion B and portion D is present.

[0136] In some embodiments of Formula I, R A , R B (if present), R C , R D (if present) or R E At least one of R 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(if present) 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 (if present) is partially or fully deuterated. In some embodiments, at least one R E is partially or fully deuterated.

[0137] In some embodiments, R α , R β , R A , R B (if present), R C , R D (if present) and R E Each is independently hydrogen or a substituent selected from the group consisting of preferred general substituents defined herein. α , R β , R A , R B (if present), R C , R D (if present) and R E Each is independently hydrogen or a substituent selected from the group consisting of the more preferred general substituents defined herein. α , R β , R A , R B (if present), R C , R D (if present) and R E Each is independently hydrogen or a substituent selected from the group consisting of the most preferred general substituents defined herein.

[0138] 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 Ir. In some embodiments, the metal M is Pt or Pd. In some embodiments, the metal M is Pt. In some embodiments, the metal M is Pd.

[0139] In some embodiments, Z 1 is N and Z 2 is C. In some embodiments, Z 1 is C and Z 2 It is N.

[0140] In some embodiments, X 2 With X 3 Between is a double bond. In some embodiments, X 2 With X 3Between is a single bond. In some embodiments, comprising X 6 of In some embodiments, X 6 of It is a single bond.

[0141] In some embodiments, X 1 and X 2 All are C. In some embodiments, X 1 or X 2 At least one of is N.

[0142] In some embodiments, X 3 To X 6 Each of is C.

[0143] In some embodiments, X 3 To X 6 At least one of is not C. In some embodiments, X 3 To X 6 At least one of X is selected from the group consisting of O, S, Se and N. In some embodiments, X 3 is selected from the group consisting of O, S, Se and N. In some embodiments, X 4 is selected from the group consisting of O, S, Se and N. In some embodiments, X 5 is selected from the group consisting of O, S, Se and N. In some embodiments, X 6 Selected from the group consisting of O, S, Se and N.

[0144] In some embodiments, X 4 or X 5 At least one of X is selected from the group consisting of O, S, Se and N. In some embodiments, X 4 or X 5 At least one of is O or S. In some embodiments, X 4 or X 5 At least one of is O. In some embodiments, X 4 or X 5 At least one of is S. In some embodiments, the portion C is a 5-membered ring.

[0145] In some embodiments, X 4 is selected from the group consisting of O, S, Se and N, and moiety B is absent. In some embodiments, X 4 is N, and moiety B is present. In some such embodiments, moiety C is a 5-membered ring.

[0146] In some embodiments, X 5is selected from the group consisting of O, S, Se and N, and the moiety D is absent. In some embodiments, X 5 is N, and moiety D is present. In some such embodiments, moiety C is a 5-membered ring.

[0147] In some embodiments, each of moiety C, moiety E, and (when present) moieties B and D is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, Aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene and aza-fluorene.

[0148] In some embodiments, portion B is absent.

[0149] In some embodiments, moiety B is present. In some embodiments, B is a monocyclic ring. In some embodiments, moiety B is a polycyclic fused ring system. In some embodiments, comprising X 3 and X 4 The ring is a 5-membered ring. In some embodiments, the ring includes X 3 and X 4 The ring is a 6-membered ring.

[0150] In some embodiments, moiety B is selected from the group consisting of benzene, pyridine, naphthalene, quinoline, and isoquinoline. In some embodiments, moiety B is benzene. In some embodiments, moiety B is naphthalene. In some embodiments, moiety B is pyridine. In some embodiments, moiety B is pyridine. In some embodiments, X 4 It is N.

[0151] In some embodiments, the moiety C is a monocyclic ring. In some embodiments, the moiety C is a polycyclic fused ring system. In some embodiments, the moiety C comprises X 4 and X 5 The ring is a 5-membered ring. In some embodiments, the ring includes X 4 and X 5 The ring is a 6-membered ring.

[0152] In some embodiments, moiety C is selected from the group consisting of benzene, pyrrole, and furan. In some embodiments, moiety C is benzene. In some embodiments, moiety C is pyrrole. In some embodiments, moiety C is furan. In some embodiments, X 4 is N or O. In some embodiments, X5 It is N or O.

[0153] In some embodiments, moiety D is absent. In some embodiments, X 5 is O. In some embodiments, X 5 It is N.

[0154] In some embodiments, moiety D is present. In some embodiments, moiety D is a monocyclic ring. In some embodiments, moiety D is a polycyclic fused ring system. In some embodiments, comprising X 5 and X 6 The ring is a 5-membered ring. In some embodiments, the ring includes X 5 and X 6 The ring is a 6-membered ring.

[0155] In some embodiments, the moiety D is selected from the group consisting of benzene, pyridine, naphthalene, quinoline, and isoquinoline. In some embodiments, the moiety D is benzene. In some embodiments, the moiety D is naphthalene. In some embodiments, the moiety D is pyridine. In some embodiments, the moiety D is X 5 It is N.

[0156] In some embodiments, the moiety E is a monocyclic ring. In some embodiments, the moiety E is a polycyclic fused ring system. In some embodiments, 6 The ring of the ring-fused moiety E is a 5-membered ring. 6 The ring of the ring-fused portion E is a 6-membered ring.

[0157] In some embodiments, moiety E is selected from the group consisting of benzene, naphthalene, and thiophene. In some embodiments, moiety E is benzene. In some embodiments, moiety E is naphthalene. In some embodiments, moiety E is thiophene.

[0158] In some embodiments, each of part B, part C, part D, and part E can independently be a polycyclic fused ring structure. In some embodiments, each of part B, part C, part D, and part E can independently be a polycyclic fused ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused ring structure has two 6-membered rings and one 5-membered ring. In some embodiments, each of part B, part C, part D, and part E can independently be selected from the group consisting of: dibenzofuran, dibenzothiophene, dibenzoselenophene, and aza-variants thereof. In some such embodiments, each of part B, part C, part D, and part E can independently be further substituted at the ortho or meta position of the O, S, or Se atom by a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza-variant contains exactly one N atom at the 6th position (ortho position of O, S, or Se) and a substituent at the 7th position (meta position of O, S, or Se).

[0159] In some embodiments, each of moiety B, moiety C, moiety D, and moiety E 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.

[0160] In some embodiments, each of part B, part C, part D and part E 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.

[0161] In some embodiments, each of part B, part C, part D and part E can independently be an aza-type of the polycyclic fused ring described above. In some such embodiments, each of part B, part C, part D and part E can independently contain exactly one aza-N atom. In some such embodiments, each of part B, part D, part E and part E 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 ortho position of the aza-N atom is substituted.

[0162] In some embodiments, at least one R A is not hydrogen. In some embodiments, at least one R AIn some embodiments, the moiety B is absent and X 3 R A Contains at least one C atom.

[0163] In some embodiments, two R A In some embodiments, X 1 and X 2 R A In some embodiments, X 2 and X 3 R A In some embodiments, two R A The ring formed by the joining or fusion is a benzene ring.

[0164] In some embodiments, R B In some embodiments, at least one of R B Contains at least one C atom.

[0165] In some embodiments, two R B In some embodiments, two R B Join or condense to form a benzene ring.

[0166] In some embodiments, at least one R C is not hydrogen. In some embodiments, at least one R C In some embodiments, the moiety B is absent and X 4 R C In some embodiments, the moiety D is absent and X 5 R C Contains at least one C atom.

[0167] In some embodiments, two R C In some embodiments, two R C Join or condense to form a benzene ring.

[0168] In some embodiments, at least one R D is not hydrogen. In some embodiments, at least one R D Contains at least one C atom.

[0169] In some embodiments, two R D In some embodiments, two R D Join or condense to form a benzene ring.

[0170] In some embodiments, at least one R E is not hydrogen. In some embodiments, at least one R E In some embodiments, the moiety D is absent and X 6 R E Contains at least one C atom.

[0171] In some embodiments, two R E In some embodiments, two R E Join or condense to form a benzene ring.

[0172] It should be understood that all embodiments related to Formula I may also be applicable to Formula I', Formula I'A, Formula I'B, Formula I'C or Formula I'D. For example, all R A The related embodiments may also be applicable to Formula I, Formula I', Formula I'A, Formula I'B, Formula I'C or Formula I'D. Similarly, all R of Formula I B , R C , R D , R E0 or R E The related embodiments are also applicable to Formula I', Formula I'A, Formula I'B, Formula I'C or Formula I'D. The same is true for all parts B, C, D, E or E in Formula I, Formula I', Formula I'A, Formula I'B, Formula I'C and Formula I'D.

[0173] In some embodiments, the compound comprises an electron withdrawing group. In some embodiments, the compound comprises an electron withdrawing group having a Hammett constant of at least 0.1.

[0174] In some embodiments, the compound comprises an electron withdrawing group selected from the group consisting of the structures listed in the following EWG1: F, CF3, CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3、(R k2 )2CCN、(R k2 )2CCF3, CNC(CF3)2, BR k3 R k2, substituted or unsubstituted 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,

[0175] Each R k1 indicates mono-substitution to the maximum permissible substitution, or no substitution;

[0176] where Y G Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO2,CR e R f 、SiR e R f and GeR e R f' ;and

[0177] 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.

[0178] In some embodiments, the compound comprises an electron withdrawing group selected from the group consisting of the structures in the following EWG2 checklist:

[0179]

[0180]

[0181] In some embodiments, the compound comprises an electron withdrawing group selected from the group consisting of the structures in the following EWG3 checklist:

[0182]

[0183] In some embodiments, the compound comprises an electron withdrawing group selected from the group consisting of the following structures listed in EWG4:

[0184] In some embodiments, the compound comprises an electron withdrawing group, which is an electron withdrawing group lacking π electrons. In some embodiments, the electron withdrawing group lacking π-electrons is selected from the group consisting of: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3. BR k2 R k3 , substituted or unsubstituted 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,

[0185] All variables are the same as defined above.

[0186] In some embodiments, at least one R A , R B , R C , R D or R E is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R A or R B is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R A or R Bis or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R A or R B is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R A or R B is or comprises an electron withdrawing group of the Pi-EWG list as defined herein.

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

[0188] In some embodiments, at least one R B is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R B is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R B is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R B is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R B is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0189] In some embodiments, at least one R C is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R C is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R C is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R C is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R Cis or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0190] In some embodiments, at least one R D is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R D is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R D is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R D is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R D is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0191] In some embodiments, at least one R E is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R E is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R E is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R E is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R E is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0192] In some embodiments, moiety D is not thiophene. In some embodiments, if moiety D is thiophene, then at least one of the following is true: (i) moiety B is present, (ii) moiety C is not benzene; (iii) moiety E is not benzene; (iv) X 1 To X 6 At least one of is not C; or (v) R A , R B , R C , R D or R E At least one of them contains at least one C.

[0193] In some embodiments, the ligand L A Selected from the group consisting of the following structures of Listing 1:

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] in:

[0211] At each occurrence, X is independently C or N;

[0212] Y A , Y B , Y C , Y D and Y E each of which is independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR';

[0213] Y C 'Selected from the group consisting of: B, BR, CR, N, P, SiR and GeR;

[0214] R AA , R BB , R CC , R DD and R EEEach of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0215] R, R', R AA , R BB , R CC , R DD and R EE are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein;

[0216] W is B, P or N; and

[0217] Any two substituents may be optionally joined or fused to form a ring.

[0218] In some embodiments of the structure of Listing 1, R A , R AA , R BB , R CC , R DD or R EE At least one of R 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 AA is partially or fully deuterated. In some embodiments, at least one R BB is partially or fully deuterated. In some embodiments, at least one R CC is partially or fully deuterated. In some embodiments, at least one R DD is partially or fully deuterated. In some embodiments, at least one R EE is partially or fully deuterated.

[0219] In some embodiments of the structure of Listing 1, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List EWG1 as defined herein. In some embodiments of the structures of List 1, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List 2 of EWG as defined herein. In some embodiments of the structures of List 1, at least one R A , R AA , R BB , R CC , R DD or REE is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments of the structures of List 1, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List 4 of EWG as defined herein. In some embodiments of the structures of List 1, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0220] In some embodiments of the structure of Listing 1, at least one R A is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 1, at least one R AA is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 1, at least one R BB is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 1, at least one R CC is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 1, at least one R DD is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 1, at least one R EE is or comprises an electron withdrawing group selected from the EWG1 list, the EWG2 list, the EWG3 list, the EWG4 list or the Pi-EWG list as defined herein.

[0221] In some embodiments, the ligand L A Selected from the group consisting of the following structures of Listing 2:

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238] in:

[0239] Y B , Y C , Y D and Y E each of which is independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR';

[0240] Y C 'Selected from the group consisting of: B, BR, CR, N, P, SiR and GeR;

[0241] R BB , R CC , R DD and R EE Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0242] R, R', R BB, R CC , R DD and R EE are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein;

[0243] The remaining variables are the same as defined previously; and

[0244] Any two substituents may be optionally fused or joined to form a ring.

[0245] In some embodiments of the structure of Listing 2, R A , R AA , R BB , R CC , R DD or R EE At least one of R 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 AA is partially or fully deuterated. In some embodiments, at least one R BB is partially or fully deuterated. In some embodiments, at least one R CC is partially or fully deuterated. In some embodiments, at least one R DD is partially or fully deuterated. In some embodiments, at least one R EE is partially or fully deuterated.

[0246] In some embodiments of the structure of Listing 2, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List 1 of EWG1 as defined herein. In some embodiments of the structures of List 2, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List 2 of EWG2 as defined herein. In some embodiments of the structures of List 2, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments of the structures of List 2, at least one R A , RAA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from List 4 of EWG as defined herein. In some embodiments of the structures of List 2, at least one R A , R AA , R BB , R CC , R DD or R EE is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0247] In some embodiments of the structure of Listing 2, at least one R A is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 2, at least one R AA is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 2, at least one R BB is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 2, at least one R CC is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 2, at least one R DD is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of the structures of List 2, at least one R EE is or comprises an electron withdrawing group selected from the EWG1 list, the EWG2 list, the EWG3 list, the EWG4 list or the Pi-EWG list as defined herein.

[0248] In some embodiments, the ligand L A Selected from L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ), wherein i is an integer from 1 to 161, and R EA, R EB , R EC , R ED , R EE , R EF and R EG Each of which is independently selected from R1 to R 211 The group consisting of L A1 (R1)(R1)(R1)(R1)(R1)(R1)(R1) to

[0249] L A161 (R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 ) are each defined in Listing 3 below:

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] Where R1 to R211 With the following structure in Listing 4:

[0267]

[0268]

[0269]

[0270]

[0271]

[0272] 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.

[0273] 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.

[0274] In some embodiments, L B is a substituted or unsubstituted phenylpyridine, and L C It is a substituted or unsubstituted acetylacetonate.

[0275] 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 connected to form a tetradentate ligand.

[0276] In some embodiments, L B comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, L B comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, L B comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, L B comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, L B comprising an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0277] In some embodiments, L C comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments, L C comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments, L C comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments, L C comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments, L C comprising an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0278] In some embodiments, L B and L C Each independently selected from the group consisting of the structures of Listing 5 below:

[0279]

[0280]

[0281]

[0282] in:

[0283] T is selected from the group consisting of B, Al, Ga and In;

[0284] 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 ;

[0285] Y 1To Y 13 Each of is independently selected from the group consisting of C and N;

[0286] 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、

[0287] 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 ;

[0288] R e and R f may be fused or joined to form a ring;

[0289] R a , R b , R c and R d Each independently represents a single substitution to the maximum allowed number of substitutions, or no substitution;

[0290] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0291] R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d Any two adjacent substituents of may be fused or joined to form a ring or to form a multidentate ligand.

[0292] In some embodiments, L B and L CEach independently selected from the group consisting of the structures of Listing 6 below:

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] in:

[0300] 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;

[0301] 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

[0302] 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.

[0303] In some embodiments, L B Include In some embodiments, Y 1 To Y 4 In some embodiments, each of Y is independently carbon. 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, Y4 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 R b or a pair of R a and R b Join or condense into a ring.

[0304] 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 ),

[0305] Where L A According to any embodiment described herein, including L A1 (R1)(R1)(R1)(R1)(R1)(R1)(R1) to L A161 (R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 );

[0306] Where k is an integer from 1 to 522, and each L Bk With the structure defined in Listing 7 below:

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319] Where j is an integer from 1 to 1416, and each L Cj-I Based on the formula structure; and

[0320] Each L Cj-II Based on the formula The structure of Cj-I and L Cj-II Each L Cj , R 201 and R 202 Each is independently defined in Listing 8 below:

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332] Where R D1 To R D246 With the following structure in Listing 9:

[0333]

[0334]

[0335]

[0336]

[0337] In some embodiments, the compound is selected from the group consisting of only L Bk The group consisting of those compounds corresponding to one of the following: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B132 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B158 , L B160 , L B162 , L B164 , L B168 , L B172 , L B175 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B222, L B231 , L B233 , L B235 , L B237 , L B240 , L B242 , L B244 , L B246 , L B248 , L B250 , L B252 , L B254 , L B256 , L B258 , L B260 , L B262 , L B264 , L B265 , L B266 , L B267 , L B268 , L B269 and L B270 .

[0338] In some embodiments, the compound is selected from the group consisting of only L Bk The group consisting of compounds corresponding to one of the following: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B126 , L B128 , L B132 , L B136 , L B138 , L B142 , L B156 , L B162 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , L B237 , L B264 , L B265 , L B266 , L B267 , L B268 , L B269 and L B270 .

[0339] In some embodiments, the compound is selected from the group consisting of only Cj-I or L Cj-II The group of compounds consisting of ligands corresponding to R201 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 , R D155 , R D161 , R D175 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , RD242 , R D245 and R D246 .

[0340] In some embodiments, the compound is selected from the group consisting of only Cj-I or L Cj-II The group of compounds consisting of ligands corresponding to R 201 and R 202 is defined as one selected from 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 .

[0341] In some embodiments, the compound is selected from the group consisting of only Cj-I The ligand is a group of compounds having a structure selected from the following list 10:

[0342]

[0343] In some embodiments, L A is selected from the group consisting of the structures of List 1, List 2, and List 3, and L B is selected from the group consisting of the structures of Listing 5, Listing 6, and Listing 7. In some embodiments, L A is selected from the group consisting of the structures of Listing 1, and L B is selected from the group consisting of the structures of Listing 7. In some embodiments, L A is selected from the group consisting of the structures of Listing 2, and L B is selected from the group consisting of the structures of Listing 7. In some embodiments, L A Choose from L A1 (R1)(R1)(R1)(R1)(R1)(R1)(R1) to

[0344] L A161 (R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 ) Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ) of List 3, and L B Choose from L Bk Listing 7 is a group of structures, where k is an integer from 1 to 522, and L Bk By L B1 To L B522 composition.

[0345] In some embodiments, the compound may be Ir(L A )2(L B ) or Ir(L A )(L B ) 2. In some of these embodiments, L A Can have Formula I as defined herein. In some of these embodiments, L A can be selected from the group consisting of the structures of Listing 1, Listing 2, and Listing 3 as defined herein. In some of these embodiments, L B can be selected from the group consisting of the structures of List 5, List 6 and List 7 as defined herein. In some of these embodiments, the compound can be Ir(L Ai (R EA )(REB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L B )、Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L B )2、Ir(L A )2(L Bk )、Ir(L A )(L Bk )2、 composed of Ir(L A1 (R1)(R1)(R1)(R1)(R1)(R1)(R1))2(L Bk ) to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L Bk ) of the compound Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L Bk ) or composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )2 to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk)2 compounds composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )2.

[0346] In some embodiments, the compound may be Ir(L A )2(L C ). In some of these embodiments, L A Can have Formula I as defined herein. In some of these embodiments, L A can be selected from the group consisting of the structures of Listing 1, Listing 2, and Listing 3 as defined herein, and L C Can be selected from L C1-I To L C1416-I and L C1-II To L C1416-II In some embodiments, the compound may be composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L Cj-I ) to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L Cj-I ) of compounds composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))2(L Cj-I ), or by Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG)2(L Cj-II ) to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG )2(L Cj-II ) of compounds composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG )2(L Cj-II ).

[0347] In some embodiments, the compound may be Ir(L A )(L B )(L C ). In some of these embodiments, L A Can have Formula I as defined herein. In some of these embodiments, L A can be selected from the group consisting of the structures of Listing 1, Listing 2 and Listing 3 as defined herein, L B is selected from the group consisting of the structures in Listing 5, Listing 6, and Listing 7, and L C Can be selected from L C1-I To L C1416-I and L C1-Ii To L C1416-II In some embodiments, the compound may be composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-I ) to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-I ) of compounds composed of Ir(L Ai (R EA)(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-I ), or by Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-II ) to Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-II ) of compounds composed of Ir(L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ))(L Bk )(L Cj-II ).

[0348] In some embodiments, the compound is selected from the group consisting of the structures of Listing 11 below:

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359] In some embodiments, the compound has the structure of Formula II':

[0360]

[0361] in:

[0362] M 1 is Pd or Pt;

[0363] Moieties E' and F are each independently a monocyclic or polycyclic fused ring system, wherein each ring of said monocyclic and said polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0364] Z 1 and Z 2 each independently is C or N;

[0365] K 1 , K 2 , K 1 ' and K 2 ' are each independently selected from the group consisting of a direct bond, O and S, wherein at least two of them are direct bonds;

[0366] L 1 , L 2 and L 3 Each independently does not exist or is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene and combinations thereof, wherein L 1 and L 2 At least one of the exists;

[0367] R E ' and R F Each independently represents zero, single, or up to the maximum allowed number of substitutions on its associated ring;

[0368] R, R', R E ' and R F Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0369] Two adjacent R A , R B , RC , R E , R E ' and R F May be joined or fused together to form a ring.

[0370] In some embodiments, the compound has the structure of Formula II:

[0371]

[0372] in:

[0373] M 1 is Pd or Pt;

[0374] Moieties E' and F are each independently a monocyclic or polycyclic fused ring system, wherein each ring of said monocyclic and said polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0375] Z 1 and Z 2 each independently is C or N;

[0376] K 1 , K 2 , K 1 ' and K 2 ' are each independently selected from the group consisting of a direct bond, O and S, wherein at least two of them are direct bonds;

[0377] L 1 , L 2 and L 3 Each independently does not exist or is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene and combinations thereof, wherein L 1 and L 2 At least one of the exists;

[0378] R E ' and R F Each independently represents zero, single, or up to the maximum allowed number of substitutions on its associated ring;

[0379] R, R', R E ' and R F Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0380] Two adjacent R A , R B , RC , R E , R E ' and R F May be joined or fused together to form a ring.

[0381] In some embodiments of Formula II or Formula II', R, R', R E and R F Each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0382] In some embodiments of Formula II or Formula II', R A , R B , R C , R D , R E , R E ' or R F At least one of R 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. In some embodiments, at least one R E is partially or fully deuterated. In some embodiments, at least one R E ' is partially or fully deuterated. In some embodiments, at least one R F In some embodiments of Formula II or Formula II', at least one R or R' (if present) is partially or fully deuterated.

[0383] In some embodiments of Formula II or Formula II', at least one of R, R', R A , R B , R C , R D , R E , R E ' or R F is or comprises an electron withdrawing group selected from the EWG1 list as defined herein. In some embodiments of Formula II or Formula II', at least one of R, R', R A , R B , R C , R D , R E , R E ' or RF is or comprises an electron withdrawing group selected from the EWG2 list as defined herein. In some embodiments of Formula II or Formula II', at least one of R, R', R A , R B , R C , R D , R E , R E ' or R F is or comprises an electron withdrawing group selected from the EWG3 list as defined herein. In some embodiments of Formula II or Formula II', at least one of R, R', R A , R B , R C , R D , R E , R E ' or R F is or comprises an electron withdrawing group selected from the EWG4 list as defined herein. In some embodiments of Formula II or Formula II', at least one of R, R', R A , R B , R C , R D , R E , R E ' or R F is or comprises an electron withdrawing group selected from the Pi-EWG list as defined herein.

[0384] In some embodiments of Formula II or Formula II', at least one R A is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R B is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R C is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R D is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R Eis or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R E ' is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R F is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list, or Pi-EWG list as defined herein. In some embodiments of Formula II or Formula II', at least one R or R' is or comprises an electron withdrawing group selected from the EWG1 list, EWG2 list, EWG3 list, EWG4 list, or Pi-EWG list as defined herein.

[0385] In some embodiments of Formula II or Formula II', both moiety E' and moiety F are 6-membered aromatic rings. In some embodiments of Formula II or Formula II', moiety F is a 5-membered or 6-membered heteroaromatic ring.

[0386] In some embodiments of Formula II or Formula II', L 1 It is O or CRR'.

[0387] In some embodiments of Formula II or Formula II', Z 2 is N and Z 1 is C. In some embodiments of Formula II or Formula II', Z 2 is C and Z 1 It is N.

[0388] In some embodiments of Formula II or Formula II', L 2 is a direct bond. In some embodiments of Formula II or Formula II', L 2 It is NR.

[0389] In some embodiments of Formula II or Formula II', K 1 , K 1 ', K 2 and K 2 ' are all direct bonds. In some embodiments of Formula II or Formula II', K 1 , K 1 ', K 2 and K 2 'One of them is O.

[0390] In some embodiments of Formula II or Formula II', the compound is selected from the group consisting of compounds having the formula Pt(L A' The group consisting of compounds of )(Ly):

[0391]

[0392] Where L A' Selected from the group consisting of the following structures of Listing 12:

[0393]

[0394]

[0395] Where L y Selected from the group consisting of the following structures of Listing 13:

[0396]

[0397]

[0398]

[0399]

[0400] in:

[0401] At each occurrence, Y B , Y E and X Z independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR'

[0402] wherein, at each occurrence, X is independently C or N;

[0403] R BB , R CC , R EE , R E ' and R F Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0404] R, R', R BB , R CC , R EE , R E ' and R F are each independently hydrogen or a substituent selected from the group consisting of general substituents; and

[0405] Any two substituents may be optionally fused or joined to form a ring.

[0406] In some embodiments, the compound is selected from the group consisting of compounds having the formula Pt(L A'The group consisting of compounds of )(Ly):

[0407]

[0408] Where L A' Choose from L A'i' (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG )(P), wherein i' is an integer from 1 to 12, P is an integer from 1 to 5, and R EA , R EB , R EC , R ED , R EE , R EF and R EG Each of which is independently selected from R1 to R 211 The group consisting of L A'1 (R1)(R1)(R1)(R1)(R1)(R1)(R1)(1) to L A'12 (R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(5) has the following structure defined in Listing 14:

[0409]

[0410]

[0411] Where L Y Choose from L Yj (R FA )(R FB ), wherein j is an integer from 1 to 4, and R FA and R FB Each of which is independently selected from R1 to R 211 The group consisting of L Y1 (R1)(R1) to L Y4 (R 211 )(R 211 ) has the following structure defined in Listing 15:

[0412]

[0413] wherein R1 to R211 have the structures defined in Listing 4 as defined herein; and

[0414] where, for each P from 1 to 5, L A' With the structure defined in the following listing:

[0415]

[0416] In some embodiments, the compound is selected from the group consisting of the structures of Listing 16 below:

[0417]

[0418] In another aspect, the present disclosure also provides a compound comprising a first ligand L of formula I* A* ,

[0419]

[0420] wherein the moiety A* and the moiety B* are each 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;

[0421] Where Z 1* -Z 4* each independently is C or N;

[0422] Where R A* and R B* Each independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0423] Where 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 );

[0424] wherein L* is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CR'R", S=O, SO2, CRR', SiRR' and GeRR';

[0425] Where R α , R β , R, R', R A* and R B*each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof;

[0426] wherein any two substituents may be joined or fused to form a ring;

[0427] Where L A* Inclusive The structure of X1 to X 14 Each of is independently C or N; each R W represents monosubstituted to the maximum permissible substitution, or no substitution; and each R W are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; and any two R W may be optionally joined or fused to form a ring;

[0428] Where L A* coordinated to a metal M having an atomic mass of at least 40;

[0429] wherein the compound is a monometallic compound;

[0430] wherein the metal M can be coordinated with other ligands; and

[0431] Where L A* Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands;

[0432] Provided that the compound is not

[0433] In some embodiments, Z 1* and Z 4* All are C. In some embodiments, Z 1* or Z 4* One of them is C and the other is N. In some embodiments, Z 1* is C, and Z 4* It is N.

[0434] In some embodiments, L* is a direct bond. In some embodiments, L* is O, S, Se, NR, CRR', or SiRR'.

[0435] In some embodiments, K 1* and K 2* Each of K is independently a direct bond. In some embodiments, K 1* or K 2* One of them can be O or s.

[0436] In some embodiments, at least one of moieties A* and B* comprises formula II* structure.

[0437] In some embodiments, R A* and R B* The moieties A* and B* are joined to form a ring structure, and the moieties A* and B* together with the formed ring structure comprise the formula structure.

[0438] In some embodiments, R A* and R B* At least one of the compounds comprises formula II* structure.

[0439] In some embodiments, moiety A* comprises a structure of Formula II*, wherein X1 to X 14 One of them coordinates to the metal directly or through an anion O or S.

[0440] In some embodiments, moiety B* comprises a structure of Formula II*, wherein X1 to X 14 One of them coordinates to the metal directly or through an anion O or S.

[0441] In some embodiments, X1 to X 14 Each of X1 to X2 is independently C. In some embodiments, X1 to X 14 At least one of X1 to X2 is N. 14 In some embodiments, at most eight of X1 to X4 are N. In some embodiments, each of X1 to X4 is independently C. In some embodiments, one of X1 to X4 is N. In some embodiments, two of X1 to X4 are N. In some embodiments, X5 and X 14 Each of X5 and X is independently C. 14 One of X5 and X is N. In some embodiments, X5 and X 14 All are N. In some embodiments, X6 and X 13 Each of X6 and X7 is independently C. 13 One of X6 and X7 is N. 13 All are N. In some embodiments, X7 and X 12 Each of X7 and X is independently C. In some embodiments,12 One of X7 and X8 is N. 12 All are N. In some embodiments, X8 to X 11 Each of X8 to X1 is independently C. 11 One of X6 to X7 is N. 11 Both of them are N.

[0442] In some embodiments, L A* Select from the following structures (Listing 1*):

[0443]

[0444]

[0445] in:

[0446] X is independently C or N at each occurrence;

[0447] Y C Selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR';

[0448] W is selected from the group consisting of B, N, C, P, Si and Ge;

[0449] R BB* and R EE* Each of the above independently represents mono-substitution to the maximum permissible substitution, or no substitution;

[0450] R, R', R BB* and R EE* are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein;

[0451] The remaining variables are the same as defined previously; and

[0452] Any two substituents may be optionally joined or fused to form a ring.

[0453] In ligand L A* In some embodiments selected from List 1*, R A* , R BB* or R EE* At least one of R 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 BB* is partially or fully deuterated. In some embodiments, at least one REE* is partially or fully deuterated.

[0454] In ligand L A* In some embodiments selected from Listing 1*, at least one R A* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0455] In ligand L A* In some embodiments selected from Listing 1*, at least one R BB* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0456] In ligand L A* In some embodiments selected from Listing 1*, at least one R EE* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0457] In some embodiments, L A*Select from the following structures (Listing 2*):

[0458]

[0459]

[0460] wherein all variables are the same as previously defined; and any two substituents may be optionally fused or joined to form a ring.

[0461] SPEC: In ligand L A In some embodiments selected from Listing 2*, R A* , R BB* or R EE* At least one of R 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 BB* is partially or fully deuterated. In some embodiments, at least one R EE* is partially or fully deuterated.

[0462] In ligand L A* In some embodiments selected from Listing 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 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.

[0463] In ligand L A* In some embodiments selected from Listing 2*, at least one R BB* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R BB* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R BB*is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0464] In ligand L A* In some embodiments selected from Listing 2*, at least one R EE* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R EE* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0465] In some embodiments, the ligand L A* Selected from L A*g (R EA )(R EB )(R EC )(R ED )(R EE ), wherein g is an integer from 1 to 4, and R EA , R EB , R EC , R ED , R EE Each of which is independently selected from R1 to R 332 The group consisting of L A*1 (R1)(R1)(R1)(R1)(R1) to L A*4 (R 332 )(R 332 )(R 332 )(R 332 )(R 332 ) are each as defined in Listing 3* below:

[0466]

[0467] Where R1 to R 332 With a structure defined like this:

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475] 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.

[0476] 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.

[0477] In some embodiments, L B is a substituted or unsubstituted phenylpyridine, and L C It is a substituted or unsubstituted acetylacetonate.

[0478] In some embodiments, the compound has the formula Pt(LA*)(LB); and wherein LA* and LB can be the same or different.

[0479] In some embodiments, L A* and L B Connect to form a tetradentate ligand.

[0480] In some embodiments, L B and L C each independently selected from the group consisting of the structures of List 5 as defined herein;

[0481] in:

[0482] T is selected from the group consisting of B, Al, Ga and In;

[0483] 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 ;

[0484] Y 1 To Y 13 Each of is independently selected from the group consisting of C and N;

[0485] 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、

[0486] 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 ;

[0487] R e and R f may be fused or joined to form a ring;

[0488] R a , R b , R c and R d Each independently represents a single substitution to the maximum allowed number of substitutions, or no substitution;

[0489] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R feach of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0490] R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d Any two adjacent substituents of may be fused or joined to form a ring or to form a multidentate ligand.

[0491] In some embodiments, L B and L C each independently selected from the group consisting of the structures of Listing 6 as defined herein;

[0492] in:

[0493] 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;

[0494] R a '、R b '、R c '、R d ' and R e ' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0495] 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.

[0496] In some embodiments, the compound has the formula Ir(L A* )3, Formula Ir(L A* )(LBk )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 ),

[0497] According to any one of technical solutions 1-6;

[0498] Where k is an integer from 1 to 522, and each L Bk Has the structure defined in Listing 7 as defined in this article;

[0499] Each L Cj-I Based on the formula structure; and

[0500] Each L Cj-II Based on the formula The structure of Cj-I and L Cj-II Each L Cj , R 201 and R 202 Each is independently defined in Listing 8 as defined in this document;

[0501] Where R D1 To R D246 Has the structure defined in Listing 9 as defined in this article.

[0502] In some embodiments, the compound is selected from the group consisting of only L Bk The group consisting of those compounds corresponding to one of the following: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B132 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B158 , L B160 , L B162 , L B164 , L B168, L B172 , L B175 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B222 , L B231 , L B233 , L B235 , L B237 , L B240 , L B242 , L B244 , L B246 , L B248 , L B250 , L B252 , L B254 , L B256 , L B258 , L B260 , L B262 , L B264 , L B265 , L B266 , L B267 , L B268 , L B269 and L B270 .

[0503] In some embodiments, the compound is selected from the group consisting of only L Bk The group consisting of compounds corresponding to one of the following: L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B126 , L B128 , L B132 , L B136 , L B138 , L B142 , L B156 , L B162 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , L B237 , L B264 , L B265 , L B266 , L B267 , LB268 , L B269 and L B270 .

[0504] In some embodiments, the compound is selected from the group consisting of only 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 , R D155 , R D161 , R D175 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210, R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 and R D246 .

[0505] In some embodiments, the compound is selected from the group consisting of only Cj-I or L Cj-II The group of compounds consisting of ligands corresponding to R 201 and R 202 is defined as one selected from 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 .

[0506] In some embodiments, the compound is selected from the group consisting of only those having Cj-I The ligands are defined as the group consisting of those compounds having one of the structures of List 10.

[0507] In some embodiments, the compound has Formula X:

[0508] in:

[0509] M 1 is Pd or Pt;

[0510] The moieties E* and F* are each independently a monocyclic or polycyclic structure comprising a 5-membered and / or 6-membered carbocyclic or heterocyclic ring;

[0511] Z 1 ' and Z 2 ' are each independently C or N;

[0512] K 1* , K 2* ', K 1 ' and K 2 ' are each independently selected from the group consisting of: a direct bond, O and S, wherein at least two of them are direct bonds;

[0513] L 1* , L 2* and L 3* Each independently does not exist or is selected from the group consisting of a direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene and combinations thereof, wherein L 1* and L 2* At least one of the exists;

[0514] R E* and R F* Each independently represents zero, single, or up to the maximum allowed number of substitutions on its associated ring;

[0515] R, R', R E* and R F* each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0516] Two adjacent substituents may be joined or fused together to form a ring.

[0517] In some embodiments of Formula X, at least one R A* , R B* , R E* or R F* 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 E* is partially or fully deuterated. In some embodiments, at least one R F* is partially or fully deuterated.

[0518] In some embodiments of Formula X, at least one R A* , R B* , R E* or R F* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A* , R B* , R E* or R F* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A* , R B* , R E* or R F* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A* , R B* , R E* or R F* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A* , R B* , R E* or R F* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0519] In some embodiments of Formula X, 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.

[0520] In some embodiments of Formula X, 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.

[0521] In some embodiments of Formula X, at least one R E* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R E* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R E* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R E* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R E* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0522] In some embodiments of Formula X, at least one R F* is or comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R F* is or comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R F* is or comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R F* is or comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R F* is or comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0523] In some embodiments, Formula X comprises an electron withdrawing group from the EWG1 list as defined herein. In some embodiments, Formula X comprises an electron withdrawing group from the EWG2 list as defined herein. In some embodiments, Formula X comprises an electron withdrawing group from the EWG3 list as defined herein. In some embodiments, Formula X comprises an electron withdrawing group from the EWG4 list as defined herein. In some embodiments, Formula X comprises an electron withdrawing group from the Pi-EWG list as defined herein.

[0524] In some embodiments, both moiety E* and moiety F* are 6-membered aromatic rings.

[0525] In some embodiments, the moiety F* is a 5- or 6-membered heteroaromatic ring.

[0526] In some embodiments, L 1* It is O or CRR'.

[0527] In some embodiments, Z 2 ' is N and Z 1 'It's C.

[0528] In some embodiments, Z 2 ' is C and Z 1 'It's N.

[0529] In some embodiments, L 2* It is a direct key.

[0530] In some embodiments, L 2* It is NR.

[0531] In some embodiments, K 1* , K 1 ', K 2* and K 2 'All are direct keys.

[0532] In some embodiments, K 1* , K 1 ', K 2* and K 2 'One of them is O.

[0533] In some embodiments, the first ligand L described herein having Formula I, Formula I' or Formula I* ACompounds may be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated or 100% deuterated. As used herein, deuteration percentage has its common meaning and includes the percentage of possible hydrogen atoms (e.g., positions of hydrogen or deuterium) replaced by deuterium atoms. In some embodiments, the carbon atoms constituting the ring coordinated with metal M are completely or partially deuterated. In some embodiments, the carbon atoms included by the polycyclic system coordinated with metal M are completely or partially deuterated. In some embodiments, the substituents connected to the monocyclic or fused polycyclic system coordinated with metal M are completely or partially deuterated.

[0534] 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.

[0535] 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, the 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, a third substituent R III , where the third substituent R III The first atom in a-III is in the ligand L C It is the farthest from the metal M among all the atoms in the atom.

[0536] In this type of heteroleptic compound, the vector V D1 、V D2 and V D3 It can be defined as follows. 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 IThe 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 .

[0537] 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 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 , D 2 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

[0538] 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 determined. 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 of the angles between the transition dipole moment axis and the vector V is less than 30°. D1 、V D2 and V D3 At least one of the angles between the transition dipole moment axis and the vector V is less than 20°. D1 、V D2 and V D3At least one of the angles between the transition dipole moment axis and the vector V is less than 15°. D1 、V D2 and V D3 At least one angle between the transition dipole moment axis and the vector V is less than 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 angles between the transition dipole moment axis and the vector V are less than 15°. D1 、V D2 and V D3 At least two of the angles therebetween are less than 10°.

[0539] 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°. In some embodiments, the transition dipole moment axis is aligned with the vector V D1 、V D2 and V D3 All three angles between them are less than 10°.

[0540] 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 or less. In some embodiments of such heteroleptic compounds, the compound has a VDR of 0.25 or less. In some embodiments of such heteroleptic compounds, the compound has a VDR of 0.20 or less. In some embodiments of such heteroleptic compounds, the compound has a VDR of 0.15 or less.

[0541] The meaning of the terms transition dipole moment axis of a compound and vertical dipole ratio of a compound are readily understood by those skilled in the art. 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, not VDR. However, it is readily understood by those skilled in the art that VDR=1-HDR.

[0542] 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 all be 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 embodiments where 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 the 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 linking ligands may be different from the other ligand(s).

[0543] 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.

[0544] The present disclosure encompasses any chemical structure comprising novel compounds of the present disclosure or their monovalent or multivalent variants. 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 compounds" refer to the same as compounds, but one hydrogen has been removed and replaced with a portion of a bond connected to the rest of the chemical structure. As used herein, "multivalent variants of compounds" refer to the same as compounds but more than one hydrogen has been removed and replaced with a portion of one or more bonds connected 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 H or D on a given part B structure can be further substituted.

[0545] C. OLEDs and Devices of the Present Disclosure

[0546] In another aspect, the present disclosure also provides an OLED device comprising a first organic layer, wherein the first organic layer contains a compound disclosed in the above compound section of the present disclosure.

[0547] In some embodiments, the OLED comprises: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a first ligand L comprising Formula I, Formula I', or Formula I* as defined herein. A of compounds.

[0548] 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.

[0549] In some embodiments, the emissive layer comprises one or more quantum dots.

[0550] In some embodiments, the organic layer may further comprise a host, wherein the host comprises a triphenylene containing a benzo-fused thiophene or a benzo-fused furan, wherein any substituent in the host is a non-fused substituent independently selected from the group consisting of: C n H 2n+1 , OC n H 2n+1 、OAr1、N(C n H 2n+1 )2, N(Ar1)(Ar2), CH=CH-Cn H 2n+1 、C≡CC n H 2n+1 、Ar1、Ar1-Ar2、C n H 2n -Ar1 or unsubstituted, wherein n is an integer from 1 to 10; and wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole and heteroaromatic analogs thereof.

[0551] 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, dihydrobenzazasilane, dibenzooxasilane, 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).

[0552] In some embodiments, the subject can be selected from the group consisting of the following structures in subject group 1:

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560] in:

[0561] Each of J1 to J6 is independently C or N;

[0562] L' is a direct bond or an organic linking group;

[0563] Y AA , Y BB , Y CC and Y DD each independently selected from the group consisting of: no bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0564] 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;

[0565] R, R', R A '、R B '、R C '、R D '、R E '、R F ' and R G 'are each 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;

[0566] Also, where possible, each unsubstituted aromatic carbon atom is optionally replaced with N to form an aza-substituted ring.

[0567] In some embodiments, at least one of J1 to J3 is N, in some embodiments, at least two of J1 to J3 are N, and in some embodiments, all three of J1 to J3 are N. In some embodiments, Y CC and Y DD Each is preferably O, S and SiRR', more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen heterocycle.

[0568] 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 when MGb is absent, EG1-EG1 to EG53-EG53 having the formula EGa-EGc, 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:

[0569]

[0570]

[0571] The structures of MG1 to MG27 are as follows:

[0572]

[0573]

[0574] 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.

[0575] 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 defined in the following List of Host Group 2, wherein each of MGb, EGa, and EGc is defined as follows:

[0576]

[0577]

[0578] In the above table, 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 indicating their bonding position in the MGb structure.

[0579] In some embodiments, the subject may be selected from the subject group 2 consisting of:

[0580]

[0581]

[0582] and combinations thereof.

[0583] In some embodiments, the organic layer may further include a host, wherein the host includes a metal complex.

[0584] In some embodiments, the emissive layer may include two hosts: a first host and a second host. In some embodiments, the first host is a hole transport host and the second host is an electron transport host. In some embodiments, the first host and the second host may form an exciplex.

[0585] In some embodiments, the compound as described herein may be a sensitizer; wherein the device may further comprise a receptor; and wherein the receptor may be selected from the group consisting of: a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0586] In another aspect, an OLED of the present disclosure may further comprise an emissive region comprising a compound as disclosed in the above Compounds section of the present disclosure.

[0587] In some embodiments, the emission region may contain a first ligand L comprising Formula I, Formula I', or Formula I* as defined herein. A of compounds.

[0588] In some embodiments, at least one of the anode, cathode, or new layer disposed above the organic emission layer acts as an enhancement layer. The enhancement layer includes a plasmon material that exhibits 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. The enhancement layer is disposed at a distance from the organic emission layer that does not exceed a threshold distance, wherein due to the presence of the enhancement layer, the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant, and the threshold distance is the position where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further includes an outcoupling layer. In some embodiments, the outcoupling layer is disposed above the enhancement layer on the opposite side of the organic emission layer. In some embodiments, the outcoupling layer is disposed on the opposite side of the emission layer from the enhancement layer, but still couples energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is dispersed into free space in the form of 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. If the energy is scattered into a non-free space mode of the OLED, other outcoupling schemes may be combined to extract the energy into free space. 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 materials, inorganic materials, perovskites, oxides, and may include stacks and / or mixtures of these materials.

[0589] The enhancement layer modifies the effective properties of the medium in which the emitter material resides, resulting in any or all of the following: reduced emissivity, modification of the emission line shape, change in emission intensity versus angle, change in stability of the emitter material, change in efficiency of the OLED, and reduced efficiency decay of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both sides 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, an OLED according to the present disclosure may also include any of the other functional layers typically found in OLEDs.

[0590] The enhancement layer may comprise a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmonic material is a material whose real part of the dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may include at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca alloys, or mixtures of these materials, and stacks of these materials. In general, a metamaterial is a medium composed of different materials, where the effect of the medium as a whole is different from the sum of its material parts. Specifically, we define an optically active metamaterial as a material that has both negative permittivity and negative permeability. On the other hand, a hyperbolic metamaterial is an anisotropic medium, where the permittivity or permeability has different signs for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are strictly distinguished from many other photonic structures, such as distributed Bragg reflectors ("DBRs"), in that the medium should appear uniform in the direction of propagation on the length scale of the wavelength of light. Using terms that are understood by those skilled in the art: the dielectric constant of a metamaterial in the direction of propagation can be approximated by an effective medium. Plasmonic materials and metamaterials provide a way to control light propagation that can enhance OLED performance in a variety of ways.

[0591] In some embodiments, the enhancement layer is provided as a flat layer. In other embodiments, the enhancement layer has periodic, quasi-periodic or randomly arranged wavelength-sized features, or periodic, quasi-periodic or randomly arranged sub-wavelength-sized features. In some embodiments, the wavelength-scale features and sub-wavelength-scale features have sharp edges.

[0592] In some embodiments, the outcoupling 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. In some embodiments, the outcoupling layer can be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, the outcoupling can be tuned 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 or an additional layer disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer, and / or changing the material of the enhancement layer. The plurality of nanoparticles of the device can 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 coated with a shell of a different type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. Multiple nanoparticles can have additional layers disposed on them. In some embodiments, the outcoupling layer can be used to adjust the polarization of the emission. Changing the size and periodicity of the outcoupling layer can select the polarization type that is preferentially outcoupled to air. In some embodiments, the outcoupling layer also acts as an electrode of the device.

[0593] On the other hand, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED), wherein the organic light-emitting device has an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound as disclosed in the above-mentioned compound section of the present disclosure.

[0594] In some embodiments, the 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 contain a first ligand L comprising Formula I as defined herein. A of compounds.

[0595] In some embodiments, the consumer product can be one of the following: a flat panel display, a computer monitor, a medical monitor, a television, a sign, a light for interior or exterior lighting and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.

[0596] In general, an OLED comprises at least one organic layer disposed between an anode and a cathode and electrically connected to the anode and the cathode. When an electric current is applied, the anode injects holes and the cathode injects electrons into one or more organic layers. The injected holes and electrons each migrate toward the oppositely charged electrode. When electrons and holes are localized on the same molecule, "excitons" are formed, which are localized electron-hole pairs with excited energy states. When the excitons relax via a photoemission mechanism, light is emitted. Excitons can be confined to excimers or excited complexes. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0597] Several OLED materials and configurations are described in US Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

[0598] The original OLEDs utilized emissive molecules to emit light from their singlet states ("fluorescence"), as disclosed, for example, in US Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a time frame of less than 10 nanoseconds.

[0599] Recently, OLEDs with emissive materials that emit light from triplet states ("phosphorescence") have been demonstrated. Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices", Nature, Vol. 395, 151-154, 1998 ("Baldo-I"); and Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence", Appl. Phys. Lett., Vol. 75, No. 3, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, Columns 5-6, which is incorporated by reference.

[0600] Figure 1 An organic light emitting device 100 is shown. The figure is not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emission layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a 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 made by depositing the layers in sequence. The properties and functions of these different layers and example materials are described in more detail in US 7,279,704, columns 6-10, which is incorporated by reference.

[0601] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of emissive materials 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 at 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 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.

[0602] 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. The device 200 can be manufactured by depositing the layers in order. Because the most common OLED configuration has a cathode disposed on the anode, and the device 200 has the cathode 215 disposed under the anode 230, the device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to the device 100 can be used in the corresponding layers of the device 200. Figure 2 An example is provided of how some layers may be omitted from the structure of device 100.

[0603] 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 a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or several 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 various layers as comprising a single material, it should be understood that a combination of materials (e.g., a mixture of a host and a dopant) or, more generally, a mixture may be used. In addition, a layer 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 include a single layer, or may further include, for example, Figure 1 and 2 Multiple layers of different organic materials are described.

[0604] 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 herein by reference in their entirety.

[0605] 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, which are incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety), and deposition by organic vapor jet printing (OVJP, also known as organic vapor jet deposition (OVJD)) (as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, 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, substituents such as alkyl and aryl groups, which may be branched or unbranched and preferably contain at least 3 carbons, 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. The solution processability of materials having an asymmetric structure may be better than that of materials having a symmetric structure, 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.

[0606] 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, etc. The barrier layer may be deposited on a substrate, above an electrode, under a substrate, or next to a substrate, an electrode, or on any other part of the device (including an edge). The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include 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. A preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material, as described in U.S. Patent No. 7,968,146, PCT Patent Application No. PCT / US2007 / 023098 and No. PCT / US2009 / 042829, which are incorporated herein by reference in their entirety. In order to be considered a "mixture", the aforementioned polymeric material and non-polymeric material constituting the barrier layer should be deposited under the same reaction conditions and / or deposited simultaneously. The weight ratio of polymeric material to non-polymeric material can be in the range of 95:5 to 5:95. The polymeric material and non-polymeric material can be produced from the same precursor material. In one example, the mixture of polymeric material and non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0607] 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 such electronic products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels), etc. that can be used by end-user product manufacturers. The electronic component module may optionally include driving electronics and / or a power supply. The device made according to the embodiments of the present disclosure can be incorporated into a variety of consumer products, and one or more electronic component modules (or units) are included in the consumer product. A consumer product comprising an OLED is disclosed, and the organic layer of the OLED includes a compound of the present invention. Such consumer products should include any kind of product containing one or more light sources and / or a certain type of visual display. Some examples of such 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, mobile phones, tablet computers, phablets, 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 made according to the present disclosure, including passive matrices and active matrices. Many 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 also be used outside this temperature range, such as in the range of -40°C to +80°C.

[0608] More details regarding OLEDs and the above definitions can be found in US Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.

[0609] 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 use the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0610] 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.

[0611] In some embodiments, the OLED further comprises a layer containing a delayed fluorescent emitter. 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.

[0612] In some embodiments, the compound may be an emitting dopant. In some embodiments, the compound may be emitted via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also referred to as E-type delayed fluorescence; see, for example, U.S. Application No. 15 / 700,352, which is incorporated herein by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the emitting dopant may be a racemic mixture, or may be enriched in one enantiomer. In some embodiments, the compound may be homogeneous (each ligand is the same). In some embodiments, the compound may 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 may all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, each ligand may be different from each other. This is also true in embodiments where 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 the 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 linking ligands may be different from the other ligand(s).

[0613] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain an acceptor in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound can be used as a component of an excitation 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 can be in the range of 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can be generated by any one or all of the sensitizer, the acceptor, and the final emitter.

[0614] According to another aspect, a formulation comprising a compound described herein is also disclosed.

[0615] The OLEDs disclosed herein may be incorporated into one or more consumer products, electronic component modules, and lighting panels.The organic layer may be an emissive layer, and the compound may be an emissive dopant in some embodiments, while the compound may be a non-emissive dopant in other embodiments.

[0616] In 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, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material.

[0617] The present disclosure encompasses any chemical structure comprising the novel compounds of the present disclosure or their monovalent or multivalent variants. 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 a portion that is identical to the compound, but one hydrogen 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 a portion that is identical to 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.

[0618] D. Combinations of Compounds of the Disclosure with Other Materials

[0619] As various examples, the materials described herein are suitable for use in specific layers in an OLED. They may also be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein may 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 may be used in combination with the compounds and devices disclosed herein, and those skilled in the art may readily consult the literature to identify other materials that may be used in combination.

[0620] a) Conductive dopants:

[0621] The charge transport layer can be doped with a conductive 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.

[0622] b)HIL / HTL:

[0623] 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 conductive dopants; 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.

[0624] Examples of aromatic amine derivatives for use in HIL or HTL include, but are not limited to, the following general structure:

[0625]

[0626] Ar 1 To Ar 9 Each of the compounds is selected from the group consisting of aromatic hydrocarbon cyclic compounds, such as benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxoline , naphthyridine, phthalazine, pteridine, dibenzopyran, 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 bonded to each other or bonded 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 by the general substituents described above, and any two substituents may be joined or fused to form a ring.

[0627] In some embodiments, each Ar 1 To Ar 9 independently comprising a portion selected from the group consisting of:

[0628]

[0629] Wherein 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.

[0630] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0631]

[0632] 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.

[0633] In some embodiments, (Y101 -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 + The minimum oxidation potential in solution for the / Fc pair is less than about 0.6 V.

[0634] 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 (e.g., 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.

[0635] c) EBL:

[0636] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of the blocking layer in the device can produce substantially higher efficiency and / or longer lifetime than similar devices lacking a blocking layer. In addition, a blocking layer can be used to limit 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 hosts in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional group as used in one of the hosts described below.

[0637] d) Subject:

[0638] The light-emitting layer of the organic EL device of the present disclosure preferably contains at least a light-emitting material as a dopant, and a host material. Examples of the host material are not particularly limited, and any metal complex or organic compound can be used as long as the host does not completely quench the emission of the dopant.

[0639] Examples of metal composites used as matrices preferably have the following general formula:

[0640]

[0641] 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.

[0642] In some embodiments, the metal complex is:

[0643]

[0644] where (ON) is a bidentate ligand with a metal coordinated to O and N atoms.

[0645] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0646] In some embodiments, the host compound contains at least one of the following groups selected from the group consisting of: aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, naphthalene, phenanthrene, fluorene, pyrene, chrysene, perylene and azulene; the group consisting of: aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole , oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoloxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, dibenzopyran, acridine, phenazine, phenothiazine, phenoxazine, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-carbazole, aza-indolocarbazole, aza-triphenylene, aza-tetraphenylene, 5λ 2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranenaphtho[3,2,1-de]anthracene; and a group consisting of 2 to 10 cyclic structural units, the units are groups of the same type or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and are directly or through at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic cyclic groups. Each option within each group may be unsubstituted or may be substituted with the general substituents described herein or may be further condensed.

[0647] In some embodiments, the host compound comprises at least one chemical moiety selected from the group consisting of:

[0648]

[0649]

[0650] wherein 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.

[0651] 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-condensed 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 aryl compounds, arylbenzoyl esters, carbazoles connected by non-conjugated groups, aza-carbazole / dibenzofuran / dibenzothiophene compounds, and high triplet metal organic metal complexes (e.g., metal-carbene complexes).

[0652] e) Emitter materials in EML:

[0653] One or more emitter materials can be used in combination with the compounds or devices disclosed herein. The emitter material can be an emitting or non-emitting material in the current device described herein. The examples of emitter materials are not particularly limited, and any compound can be used as long as the compound can produce emission in a conventional OLED device. Examples of suitable emitter materials include, but are not limited to, compounds that can produce 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 processes.

[0654] In some embodiments, the emitter material has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0655] Where L 1 , L 2 and L 3 Can be the same or different;

[0656] where x is 1, 2, or 3;

[0657] Where y is 0, 1 or 2;

[0658] where z is 0, 1 or 2;

[0659] Where x+y+z is the oxidation state of metal M;

[0660] Where L 1 Selected from the group consisting of structures in the following ligand list:

[0661]

[0662]

[0663]

[0664] Where L 2 and L 3 Independently choose freedom and a group consisting of structures in the ligand list; where:

[0665] M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag and Cu;

[0666] T is selected from the group consisting of B, Al, Ga and In;

[0667] K 1' is a direct key or is selected from the group consisting of: NR e , PR e , O, S and Se;

[0668] Y 1 To Y 15 are each independently selected from the group consisting of carbon and nitrogen;

[0669] Y'Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO2,CR e R f 、SiR e R f and GeR e R f ;

[0670] R a , R b , R c and R d can each independently represent a single substitution to the maximum possible number of substitutions, or no substitution;

[0671] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0672] Any two of the substituents may be fused or joined to form a ring or to form a polydentate ligand.

[0673] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 1:

[0674]

[0675]

[0676]

[0677]

[0678] in

[0679] X 96 To X 99Each of is independently C or N;

[0680] Each Y 100 Independently selected from the group consisting of NR", O, S and Se;

[0681] R 10a , R 20a , R 30a , R 40a and R 50a Each of independently represents monosubstitution, up to maximum substitution, or no substitution;

[0682] 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.

[0683] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 2:

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691] in:

[0692] Each Y 100 Independently selected from the group consisting of NR", O, S and Se;

[0693] L is independently selected from the group consisting of a direct bond, BR", BR"R"', NR", PR", O, S, Se, C=O, C=S, C=Se, C=NR", C=CR"R"', S=O, SO2, CR", CR"R"', SiR"R"', GeR"R"', alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

[0694] X 100 and X 200 at each occurrence selected from the group consisting of: O, S, Se, NR", and CR"R"';

[0695] R A ”、R B ”、R C ”、R D ”、R E ” and R F ” each independently represents mono-substitution, up to maximum substitution, or no substitution;

[0696] 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 defined herein; any two substituents may be joined or fused to form a ring;

[0697] 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.

[0698] In some embodiments of 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.

[0699] 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:

[0700]

[0701]

[0702]

[0703] Among them A 1 -A 9 are each independently selected from C or N;

[0704] R P , R Q and R U each independently represents monosubstitution, up to maximum substitution, or no substitution;

[0705] Where R P , R P , R U , R SA , R SB , R RA , R RB , R RC , R RD , R RE and R RF Each 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.

[0706] In some embodiments of the OLED, the delayed fluorescent material comprises at least one donor moiety selected from the group consisting of:

[0707]

[0708]

[0709] where Y T , Y U , Y V and Y W Each is independently selected from the group consisting of B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO2.

[0710] In some of the above embodiments, any carbon ring atom, up to a total of three carbon ring atoms together with their substituents, in each benzene ring of any of the above structures can be replaced by N.

[0711] In some embodiments, the delayed fluorescent material comprises at least one 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).

[0712] In some embodiments, the fluorescent material comprises at least one chemical moiety selected from the group consisting of:

[0713]

[0714]

[0715]

[0716] 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 SO2;

[0717] Where X F and X G are each independently selected from the group consisting of C and N.

[0718] In some of the above embodiments, any carbon ring atom, up to a total of three carbon ring atoms together with their substituents, in each benzene ring of any of the above structures can be replaced by N.

[0719] f)HBL:

[0720] 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 the blocking layer in the device can result in substantially higher efficiency and / or longer lifetime than a similar device lacking the blocking layer. In addition, the blocking layer can be used to confine emission to a desired area 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 emitters closest to the HBL interface.

[0721] In some embodiments, the compound used in HBL contains the same molecule or the same functional group as used in the above-mentioned subject.

[0722] In some embodiments, the compound used in HBL comprises at least one chemical moiety selected from the group consisting of:

[0723]

[0724] wherein k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0725] g)ETL:

[0726] 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 composite or organic compound may be used as long as it is typically used to transport electrons.

[0727] In some embodiments, the compounds used in the ETL contain at least one of the following moieties in the molecule:

[0728]

[0729] and fullerenes; 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.

[0730] In some embodiments, the metal complex used in the ETL contains but is not limited to the following general formula:

[0731]

[0732] 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.

[0733] 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.

[0734] h) Charge Generation Layer (CGL)

[0735] In a tandem or stacked OLED, the CGL plays an important role in performance and is composed of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and 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 include n and p conductivity dopants used in the transport layer.

[0736] 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.

[0737] It should be understood that the various embodiments described herein are only for example, and are not intended to limit the scope of the present invention. For example, many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. The present invention as required can therefore include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

[0738] E. Experimental Data

[0739] Synthesis of Example 1 of the present invention

[0740]

[0741] 1-Methoxydibenzo[f,h]isoquinoline

[0742] A mixture of 4-chloro-2-methoxynicotinic acid (20.6 g, 110 mmol, 1.0 equiv), 2-iodo-1,1'-biphenyl (33.4 g, 120 mmol, 1.1 equiv), potassium carbonate (45 g, 326 mmol, 3.0 equiv) and anhydrous N,N-dimethylformamide (630 mL) was bubbled with nitrogen. Bis(triphenylphosphine)palladium(II) dichloride (6.2 g, 8.8 mmol, 0.08 equiv) was added and the reaction mixture was heated at 140 °C for 16 hours. LCMS analysis of the reaction aliquots showed that the reaction was complete. After cooling to room temperature (RT), the reaction mixture was poured into water and allowed to stand for 2 hours. The suspension was filtered and the solid was washed with water. The solid was wet-triturated with acetonitrile at 50 °C, the suspension was filtered and the solid was washed with acetonitrile. The solid was air-dried to give 1-methoxydibenzo[f,h]isoquinoline as an off-white solid.

[0743] Dibenzo[f,h]isoquinolin-1-ol

[0744] Sodium ethanethiolate (27.7 g, 330 mmol, 3.0 equiv) was added to a nitrogen bubbling solution of 1-methoxy-dibenzo[f,h]isoquinoline (28.5 g, 110 mmol, 1.0 equiv) in N-methylpyrrolidone (500 mL), followed by heating the reaction mixture at 100 °C for 2 hours. The reaction mixture was cooled to 40 °C, poured into water and allowed to stand for 1 hour. The suspension was filtered and the solid was air-dried. The solid was triturated with acetonitrile, filtered and air-dried to give dibenzo[f,h]isoquinolin-1-ol as an off-white solid.

[0745] dibenzo[f,h]isoquinolin-1-yl trifluoromethanesulfonate

[0746] A nitrogen-bubbled solution of dibenzo[f,h]isoquinolin-1-ol (18.4 g, 75 mmol, 1.0 eq.) and triethylamine (35 mL, 251 mmol, 3.4 eq.) in dichloromethane (450 mL) was cooled in an ice-water bath. Trifluoromethanesulfonic anhydride (35 mL, 209 mmol, 2.8 eq.) was added dropwise. After warming to room temperature over 16 hours, LCMS analysis of the reaction aliquot showed that the reaction was complete. The reaction mixture was poured into water and dichloromethane, the layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was triturated with acetonitrile at 50 °C. The suspension was filtered to give the first batch of product. Recrystallization of the filtrate produced additional product. The solids were combined to give dibenzo[f,h]isoquinolin-1-yl trifluoromethanesulfonate as a light brown solid.

[0747] 1-(3-Bronaphthalen-2-yl)dibenzo[f,h]isoquinoline

[0748] A mixture of dibenzo[f,h]isoquinolin-1-yl trifluoromethanesulfonate (5.0 g, 13.3 mmol, 1.0 equiv), (3-bromonaphthalen-2-yl)boronic acid (3.7 g, 14.7 mmol, 1.1 equiv), potassium carbonate (4.2 g, 30.4 mmol, 2.3 equiv) and a 4:2:1 mixture of toluene, water and ethanol (175 mL) was bubbled with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.11 mmol, 0.08 equiv) was added and the reaction mixture was heated at reflux for 16 hours. LCMS analysis of an aliquot showed the reaction was complete. The reaction mixture was cooled to room temperature and poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over sodium sulfate and filtered. The filtrate was adsorbed onto silica gel and purified on a Biotage automated chromatography system eluting with 17% ethyl acetate in hexanes. The purest product fractions were concentrated thoroughly under reduced pressure. The suspension was filtered and the solids were air-dried to give the product as a pale yellow solid. The filtrate was concentrated and the pale yellow solid was triturated with acetonitrile to give additional product. The combined two batches of solids were dried in a vacuum oven to give 1-(3-bromo-naphthalen-2-yl)dibenzo[f,h]-isoquinoline as a tan solid.

[0749] Naphtho[2,3-h]phenanthro[9,10,1-def]quinoline

[0750] A solution of 1-(3-bromonaphthalene-2-yl)dibenzo[f,h]isoquinoline (3.0 g, 6.9 mmol, 1.0 equiv) in xylene (30 mL) was bubbled with nitrogen. Potassium hydroxide pellets (4.9 g, 87 mmol, 12.6 equiv) were added, and the reaction mixture was heated at 140 °C for 48 hours. The reaction mixture was cooled to room temperature and poured into water. The suspension was filtered and the solid was washed with water. The solid was triturated with acetonitrile and filtered. The brown solid was washed with methyl tert-butyl ether and air-dried. The crude solid was purified on a Biotage automated chromatography system, eluting with 25% ethyl acetate in hexanes (containing 15% dichloromethane additive) until 100% dichloromethane. The residual light yellow solid was triturated with acetonitrile, followed by trituration with hexanes and filtering the solid. The solid was air-dried for 10 minutes to afford naphtho[2,3-h]phenanthroline-[9,10,1-def]quinoline as a very fluffy, papery, light yellow solid.

[0751] Bis[(naphtho[2,3-h]phenanthro[9,10,1-def]quinolin-1-yl)-16'-yl]-[3,7-diethyl-4,6-nonanedione-k2O,O']iridium(III)

[0752] A solution of naphtho[2,3-h]phenanthroline-[9,10,1-def]quinoline (837 mg, 2.37 mmol, 4.0 equiv) in dichlorobenzene (20 mL) was bubbled with nitrogen followed by the addition of bis(1,5-cyclooctadiene)diiridium(I)dichloride (0.398 g, 0.593 mmol, 1.0 equiv). The reaction mixture was heated at 140 °C for 24 hours. After the reaction mixture was cooled to room temperature, potassium (Z)-3,7-diethyl-6-oxonon-4-ene-4-oate (1534 mg, 2.37 mmol, 4.0 equiv) was added. The reaction mixture was heated at 40 °C in a flask wrapped in foil to protect from light for 16 hours. After cooling to room temperature, the reaction mixture was poured directly into a flask containing (diatomaceous earth) in a dry-loaded cartridge and purified on a Biotage automated chromatography system, eluting with 100% hexane until all dichlorobenzene was eluted, followed by elution with hexane containing 0-100% dichloromethane. The cleanest product fraction was concentrated under reduced pressure. The residual solid was wet-triturated with methanol and filtered. The solid was dried in a vacuum oven at 50° C. to give bis[(naphtho[2,3-h]phenanthro[9,10,1-def]quinolin-1-yl)-16'-yl]-[3,7-diethyl-4,6-nonanedione-k2O,O']iridium(III) as a red solid.

[0753] Synthesis of Example 2 of the present invention

[0754]

[0755]

[0756] 3',5-di-tert-butyl-[1,1'-biphenyl]-2-amine

[0757] A flask was charged with 2-bromo-4-(tert-butyl)aniline (20.00 g, 1 eq., 87.67 mmol), (3-(tert-butyl)phenyl)boronic acid (15.61 g, 1 eq., 87.67 mmol), K2CO3 (18.17 g, 1.5 eq., 131.5 mmol), toluene (100.0 mL), dioxane (100.0 mL) and water (60.00 mL). The reaction mixture was degassed with bubbling nitrogen. Pd(PPh3)4 (2.026 g, 0.02 eq., 1.753 mmol) was added and the reaction mixture was heated to 100°C and maintained for 16 hours. The reactants were allowed to cool to room temperature and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water followed by brine and concentrated in vacuo to give 3',5-di-tert-butyl-[1,1'-biphenyl]-2-amine as a brown oil.

[0758] 3',5-Di-tert-butyl-2-iodo-1,1'-biphenyl

[0759] To a solution of 3',5-di-tert-butyl-[1,1'-biphenyl]-2-amine (29.40 g, 1 eq., 104.5 mmol) in THF (250 mL) cooled in ice to 5 °C was added a cooled 4 M hydrochloric acid solution (260 mL) dropwise. Water (70 mL) containing sodium nitrite (8.648 g, 1.2 eq., 125.4 mmol) was added dropwise to the light yellow solution. The reaction mixture was stirred at 4 °C for 1 hour. A pre-cooled solution of potassium iodide (41.62 g, 2.4 eq., 250.7 mmol) in water (110 mL) was added dropwise. The dark brown mixture was stirred at 0 °C for 1 hour, then the ice bath was removed and the mixture was stirred at room temperature overnight. Water and EtOAc were added to the reaction mixture and the layers were separated. The aqueous layer was extracted with additional EtOAc, and the combined organic layers were washed with water and 10% Na2S2O3 aqueous solution. The organic layer was further washed with water, aqueous NaHCO3 and aqueous NH4Cl and dried over MgSO4, charcoal was added and the mixture was filtered through a short pad of silica and celite. The solvent was removed under reduced pressure to give a brown oil.

[0760] 2,8-Di-tert-butyldibenzo[b,d]iodonium-5-ol trifluoromethanesulfonate

[0761] 3',5-di-tert-butyl-2-iodo-1,1'-biphenyl (27.35g, 1 equivalent, 69.71mmol) was added to an ice-cold solution of DCM (300mL) with 3-chlorobenzoperoxyacid (18.04g, 1.5 equivalents, 104.6mmol). Trifluoromethanesulfonic acid (31.39g, 18.51mL, 3 equivalents, 209.1mmol) was added dropwise to this mixture. The mixture was stirred at 0°C for 40 minutes and then allowed to warm to room temperature. The mixture was evaporated under reduced pressure and the dark residue was wet-ground in TBME for a few minutes. The light purple solid was filtered out and washed with TBME. The solid was further wet-ground with TBME and the solid was collected by filtration to obtain the product in the form of a light pink solid.

[0762] 7,10-Di-tert-butyl-1-methoxydibenzo[f,h]isoquinoline

[0763] To trifluoromethanesulfonic acid 2,8-di-tert-butyl-5H-513-dibenzo[b,d]iodo-5-yl ester (21.80 g, 1 eq., 40.34 mmol), 4-chloro-2-methoxynicotinic acid (11.35 g, 1.5 eq., 60.51 mmol) and potassium carbonate (16.73 g, 3 eq., 121.0 mmol) was added palladium acetate (905.7 mg, 0.1 eq., 4.034 mmol) followed by DMF (400 mL). The vessel was degassed and heated at 120 °C overnight. The dark mixture was diluted with TBME, charcoal and diatomaceous earth were added and stirred at room temperature. The mixture was filtered through a short pad of diatomaceous earth and washed with additional TBME to give a dark brown solution. Water was added thereto and the layers were separated. The aqueous layer was extracted with TBME, and the combined organic layers were washed with brine, NH4Cl, NaHCO3, 10% aqueous sodium thiosulfate solution and brine, then dried over MgSO4. The mixture was filtered through a short silica pad and eluted with TBME. The solvent was removed under reduced pressure to give a brown solid residue. The crude residue was triturated with methanol to give a light beige solid. Further recrystallization of the filtrate produced additional product.

[0764] 7,10-Di-tert-butyldibenzo[f,h]isoquinolin-1-ol

[0765] To a solution of 7,10-di-tert-butyl-1-methoxydibenzo[f,h]isoquinoline (21.29 g, 1 eq, 57.31 mmol) in DCE (225 mL) was added AcOH (70.00 mL, 33% by weight, 6.746 eq, 386.6 mmol) containing 33% hydrobromic acid. The orange mixture was stirred and heated at 71 °C for 4 hours. The reaction mixture was allowed to cool to room temperature. A precipitate formed and was collected by filtration and washed with water to give a cream solid and a brown filtrate. The white solid was dissolved in DCM containing 2% MeOH and washed with dilute ammonia. The layers were separated and the organic layer was dried over MgSO4. The organic layer was filtered through a short pad of silica and alumina, eluting with DCM / MeOH. The solvent was removed under reduced pressure to give a milky white solid.

[0766] Recrystallization of the filtrate produced additional product.

[0767] 7,10-Di-tert-butyldibenzo[f,h]isoquinolin-1-yl

[0768] A nitrogen sparged solution of 7,10-di-tert-butyldibenzo[f,h]-isoquinolin-1-ol (8.0 g, 22.38 mmol, 1.0 equiv) and triethylamine (9.4 mL, 67.13 mmol, 3.0 equiv) in dichloromethane (120 mL) was cooled in an ice-water bath. Trifluoromethanesulfonic anhydride (10.6 mL, 62.66 mmol, 2.8 equiv) was added dropwise via syringe, and the reaction mixture was then warmed to room temperature over 16 hours. The reaction mixture was poured into water and dichloromethane, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude trifluoromethanesulfonic acid 7,10-di-tert-butyldibenzo[f,h]isoquinolin-1-yl ester as a sticky brown semisolid.

[0769] 1-(3-Bronaphthalen-2-yl)-7,10-di-tert-butyldibenzo[f,h]isoquinoline

[0770] Trifluoromethanesulfonic acid 7,10-di-tert-butyldibenzo[f,h]isoquinolin-1-yl ester (10.95 g, 22.37 mmol, 1.0 equiv), (3-bromo-naphthalen-2-yl)boronic acid (6.73 g, 26.84 mmol, 1.2 equiv), potassium carbonate (7.11 g, 51.45 mmol, 2.3 equiv), toluene (80 mL), water (40 mL) and ethanol (20 mL) were bubbled with nitrogen. Bis(triphenylphosphine)palladium(II) dichloride (1.26 g, 1.79 mmol, 0.08 equiv) was added, and the reaction mixture was heated at 93° C. for 18 hours. After cooling to room temperature, the mixture was diluted with saturated brine and ethyl acetate. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a Biotage automated chromatography system eluting with ethyl acetate / dichloromethane / hexanes to afford 1-(3-bromonaphthalen-2-yl)-7,10-di-tert-butyldibenzo[f,h]isoquinoline as a tan solid.

[0771] 6,9-Di-tert-butylnaphtho[2,3-h]phenanthro[9,10,1-def]quinoline

[0772] A 250 mL round bottom flask equipped with a stir bar was charged with 1-(3-bromonaphthalene-2-yl)-7,10-di-tert-butyldibenzo[f,h]isoquinoline (4.0 g, 7.32 mmol, 1.0 equiv), potassium hydroxide pellets (61.6 g, 1.10 mol, 150 equiv) and xylene (90 mL). The reaction mixture was heated at 160 ° C for 2 days. After cooling to room temperature, the mixture was diluted with water, and the suspension was filtered. The solid was washed with water and dried to give 6,9-di-tert-butylnaphtho[2,3-h]phenanthro[9,10,1-def]quinoline (1.40 g, 41% yield, 99.7% UPLC purity) as a gray paper solid.

[0773] Bis[(6,9-di-tert-butylnaphtho[2,3-h]phenanthro[9,10,1-def]quinolin-1-yl)-16'-yl]-(3,7-diethylnonane-4,6-dione-κ2O,O')iridium(III)

[0774] A solution of 6,9-di-tert-butylnaphtho[2,3-h]phenanthro[9,10,1-def]quinoline (1.40 g, 3.01 mmol, 4.0 equiv) and bis(1,5-cyclooctadiene)-diiridium(I) dichloride (506 mg, 753 μmol, 1.0 equiv) in xylene (30 mL) was heated at 130 °C for 4 days. The reaction mixture was cooled to room temperature. Potassium (Z)-3,7-diethyl-6-oxonon-4-ene-4-oate (566 mg, 2.26 mmol, 3.0 equiv) was added and the reaction mixture was heated at 40 °C for 18 hours. The reaction mixture was cooled to room temperature and purified directly on a Biotage automated chromatography system, eluting with dichloromethane / hexane. The solid obtained was triturated with dichloromethane / methanol. The suspension was filtered and the solid was dried to give bis[(6,9-di-tert-butylnaphtho[2,3-h]phenanthro[9,10,1-def]quinolin-1-yl)-16'-yl]-(3,7-diethylnonane-4,6-dione-κ2O,O')iridium(III) as a red solid.

[0775] Photoluminescence properties

[0776] Emission spectra were collected on a Horiba Fluorolog-3 spectrofluorometer equipped with a Synapse Plus CCD detector. All samples were excited at 340 nm. PLQY values ​​were measured using a Hamamatsu Quantaurus-QY Plus UV-NIR absolute PL quantum yield spectrometer with an excitation wavelength of 340 nm. A 1% solution of emitter and PMMA in toluene was prepared, filtered, and drop-cast onto a quartz substrate.

[0777] The triplet energy (T1) of compounds 1 and 2 of the present invention and the comparative compound was measured to be 617 nm, 612 nm and 615 nm, respectively. T1 was obtained using the initial emission, which was obtained at 20% of the peak height of the gated emission of the frozen sample in 2-MeTHF at 77 K. The gated emission spectra were collected on a Horiba Fluorolog-3 spectrofluorometer equipped with a xenon flash lamp (flash delay of 10 milliseconds and collection window of 50 milliseconds). The sample was excited at 300 nm.

[0778] The T1 energies were obtained from the emission spectrum of frozen samples in 2-MeTHF at 77 K.

[0779]

[0780] Table 1. Photoluminescence data of inventive and comparative examples in PMMA. The PLQYs of inventive compounds are presented normalized to the values ​​of comparative compounds.

[0781]

[0782] Table 1 summarizes the photoluminescent properties of compounds of the invention containing five benzene rings fused together in a linear geometry and a comparative compound containing only four benzene rings fused in a linear geometry. All three compounds showed emission with similar peak wavelengths, however, the line shape and PLQY of the inventive examples were significantly improved over the comparative examples. These improvements exceed any values ​​attributable to experimental error, and the observed improvements are significant and unexpected.

[0783] Device Examples

[0784] All example devices were operated under high vacuum (<10 -7 The anode electrode is The cathode is made of indium tin oxide (ITO). Liq (8-hydroxyquinoline lithium) and subsequently All devices were packaged with epoxy-sealed glass lids in a nitrogen glove box (H2O and O2 <1 ppm) immediately after fabrication, and a desiccant was incorporated inside the package. The organic stack of the device example consisted of the following in sequence: starting with the ITO surface, LG101 (purchased from LG Chem); as a hole transport layer (HTL) HTM; as an electron blocking layer (EBL) EBM; contains body and 3% emitter The emission layer (EML) and the electron transport layer (ETL) doped with 35% ETM Liq (8-hydroxyquinoline lithium). Table 2 shows the thickness and materials of the device layers.

[0785] Table 2. Device layer materials and thicknesses

[0786]

[0787] The chemical structure of the device material is shown below:

[0788]

[0789] The device was manufactured and tested by EL and JVL. For this purpose, the samples were tested at 10 mA / cm using a 2-channel Keysight B2902A SMU. 2 The current density was energized and measured using a Photo Research PR735 spectroradiometer. The radiance (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 is used to convert the photodiode current into photon counts. The voltage is swept from 0 to 200 mA / cm 2 The voltage of the device was calculated using the total integrated photon count. All results are summarized in Table 3. The voltage, EQE and LE of Inventive Example 2 (Device 1) are reported as relative numbers normalized to the results of the Comparative Example (Device 2).

[0790] Table 3. Device data of the present invention examples and comparative examples

[0791]

[0792] Table 3 summarizes the performance of electroluminescent devices of the inventive device containing five benzene rings fused together in a linear geometry and a comparative device containing only four benzene rings fused in a linear geometry. Both devices show emission with a peak wavelength of about 620nm, however, the linearity, turn-on voltage, EQE and luminous efficiency of the inventive example are significantly improved compared to the comparative example. These improvements exceed any values ​​attributable to experimental error, and the observed improvements are significant and unexpected.

Claims

1. A compound comprising a first ligand L of formula I' A , wherein moieties A, B, C, D and E0 are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic ring or the polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; Where W 1 , W 2 , W 3 and W 4 Each independently selected from the group consisting of: BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR'; Where W 5 and W 6 Each independently selected from the group consisting of: BR, N, CR, SiR and GeR; Where K 1 and K 2 Each of which is 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 ); K 1 and K 2 At least one of is a direct key; R A , R B , R C , R D and R E0 Each of the above independently represents a single substitution to the maximum permissible substitution, or no substitution; R, R', R α , R β , R A , R B , R C , R D and R E0 each independently is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; L A Coordinate with metal M; M can coordinate with other ligands; L A Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; wherein any two substituents may be joined or fused to form a ring; and The compound is not 2. The compound according to claim 1, wherein the first ligand L A Having the structure of Formula I: in: each of moiety C, moiety E, and when present, moieties B and D, are independently a monocyclic or polycyclic fused ring system, wherein each ring in said monocyclic and said polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; The dashed arcs indicate that part B and part D are optionally present; X 1 , X 2 , Z 1 and Z 2 Each of is independently C or N; X 3 To X 6 Each of which is independently selected from the group consisting of: C, O, S, Se, N, P, Si, and Ge; If X 3 To X 6 is carbon, then at least one of portion B and portion D is present; 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 ); K 1 and K 2 At least one of is a direct key; Each independently represent a single bond or a double bond; R A , R B , R C , R D and R E Each of the above independently represents a single substitution to the maximum permissible substitution, or no substitution; R α , R β , R A , R B , R C , R D and R E each independently is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; L A Coordinate with metal M; M can coordinate with other ligands; L A can be joined with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; and Any two substituents may be joined or fused to form a ring.

3. The compound of claim 1, wherein each of moiety C, moiety E, and when present, moieties B and D are independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzo Thiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene and aza-fluorene; and / or Two of the R A are joined or fused to form a ring; and / or wherein two R B When present, they are joined or fused to form a ring; and / or wherein two R C are joined or fused to form a ring; and / or wherein two R D When present, they are joined or fused to form a ring; and / or wherein two R E are joined or fused to form a ring; and / or wherein the compound comprises an electron withdrawing group; 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 the ligand L A Select from the group consisting of: in: At each occurrence, X is independently C or N; Y A , Y B , Y C , Y D and Y E Each of which is independently selected from the group consisting of: BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR'; Y C 'Selected from the group consisting of C, Si and Ge; R AA , R BB , R CC , R DD and R EE Each of the above independently represents a single substitution to the maximum permissible substitution, or no substitution; R, R', R AA , R BB , R CC , R DD and R EE are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; and Any two substituents may be optionally fused or joined to form a ring.

5. The compound according to claim 1, wherein the ligand L A Select from the group consisting of: in: Y B , Y C , Y D and Y E each of which is independently selected from the group consisting of BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR' and GeRR'; Y C 'Selected from the group consisting of C, Si and Ge; R BB , R CC , R DD and R EE Each of the above independently represents a single substitution to the maximum permissible substitution, or no substitution; R, R', R BB , R CC , R DD and R EE are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; and Any two substituents may be optionally fused or joined to form a ring.

6. The compound according to claim 1, wherein the ligand L A Selected from L Ai (R EA )(R EB )(R EC )(R ED )(R EE )(R EF )(R EG ), wherein i is an integer from 1 to 161, and R EA , R EB , R EC , R ED , R EE , R EF and R EG Each of which is independently selected from R1 to R 211 A group of L A1 (R1)(R1)(R1)(R1)(R1)(R1)(R1) to L A161 (R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 )(R 211 ) are defined as follows: Where R1 to R 211 Has the following structure:

7. 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 are each bidentate ligands; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of the metal M.

8. The compound according to claim 7, 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.

9. The compound according to claim 7, 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 is independently selected from the group consisting of C and N; Y'Select from the group consisting of: BR e , BR e R f NR e , PR e 、P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e 、C=CR e R f 、S=O、SO2、CR e R f 、SiR e R f and GeR e R f ; R e and R f may be fused or joined to form a ring; R a , R b , R c and R d Each independently represents a single substitution 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 are each independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, seleno, 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 adjacent substituents of may be fused or joined to form a ring or to form a multidentate ligand.

10. The compound according to claim 6, 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 522, and each L Bk Has the structure defined as follows: Where j is an integer from 1 to 1416, and each L Cj-I Based on the formula structure; and Each L Cj-II Based on the formula The structure of Cj-I and L Cj-II Each L Cj , R 201 and R 202 The definition is as follows: Where R D1 To R D246 Has the following structure:

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

12. The compound according to claim 7, wherein the compound has the following structure: Formula II': Formula II: in: M 1 is Pd or Pt; Moieties E' and F are each independently a monocyclic or polycyclic fused ring system, wherein each ring of said monocyclic and said polycyclic fused ring system is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; Z 1 and Z 2 each independently is C or N; K 1 , K 2 , K 1 ' and K 2 ' are each independently selected from the group consisting of a direct bond, O and S, wherein at least two of them are direct bonds; L 1 , L 2 and L 3 Each independently does not exist or is selected from the group consisting of: direct key, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof, wherein L 1 and L 2 At least one of the exists; R E ' and R F Each independently represents zero, single, or up to the maximum allowed number of substitutions on its associated ring; R, R', R E ' and R F Each of is independently hydrogen or a substituent selected from the group consisting of: deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thiol, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof; and Two adjacent R A , R B , R C , R E , R E ' and R F May be joined or fused together to form a ring.

13. A compound comprising a first ligand L of formula I* A* : wherein the moiety A* and the moiety B* are each 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; Where Z 1* -Z 4* each independently is C or N; Where R A* and R B* Each independently represents mono-substitution to the maximum permissible substitution, or no substitution; Where 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 ); Wherein 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=CR'R", S=O, SO2, CRR', SiRR' and GeRR'; Where R α , R β , R, R', R A* and R B* each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; wherein any two substituents may be joined or fused to form a ring; Where L A* Containing Formula II* The structure of X1 to X 14 Each of is independently C or N; each R W represents monosubstituted to the maximum permissible substitution, or no substitution; and each R W are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof; and any two R W may be optionally joined or fused to form a ring; Where L A* coordinated to a metal M having an atomic mass of at least 40; wherein the compound is a monometallic compound; wherein the metal M can be coordinated with other ligands; and Where L A* Can be joined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; Provided that the compound is not 14. An organic light-emitting device, comprising: anode; cathode; and An organic layer is disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.

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

Images