Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. Provided is an organometallic compound comprising a Pd or Pt atom as a central metal atom coordinated by a tetradentate ligand comprising at least four moieties, each independently being a monocyclic or polycyclic fused ring system, each moiety being a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring. Formulations comprising these organometallic compounds are also provided. Organic light emitting devices (OLED) and related consumer products utilizing these organometallic compounds are also provided.

Description

[0001] Cross - Reference to Related Applications

[0002] This application claims the benefit of priority to U.S. Provisional Application No. 63 / 619,914, filed on November 1, 2024, the entire content of which is incorporated herein by reference. This application claims the benefit of priority to U.S. Provisional Application No. 63 / 609,996, filed on December 14, 2023, the entire content of which is incorporated herein by reference. This application claims the benefit of priority to U.S. Provisional Application No. 63 / 632,362, filed on April 10, 2024, the entire content of which is incorporated herein by reference. This application claims the benefit of priority to U.S. Provisional Application No. 63 / 619,527, filed on January 10, 2024, the entire content of which is incorporated herein by reference. This application claims the benefit of priority to U.S. Provisional Application No. 63 / 614,848, filed on December 26, 2023, the entire content of which is incorporated herein by reference. This application claims the benefit of priority to U.S. Provisional Application No. 63 / 618,688, filed on January 8, 2024, the entire content of which is incorporated herein by reference. TECHNICAL FIELD

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

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

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

[0006] One application of emissive molecules is full-color displays. Industry standards for such displays require pixels that are adapted to emit specific colors (referred to as "saturated" colors). Specifically, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technique can also be used for OLEDs. 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 structure of Formula I:

[0008]

[0009] wherein moieties A, B, C, and D 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;

[0010] wherein M is selected from Pt and Pd;

[0011] wherein X 1 -X 4 are each independently C or N;

[0012] wherein Z 1 -Z 4 are each independently C or N;

[0013] wherein L is a direct bond, or an organic linking group having one or two linking atoms;

[0014] wherein K 1 and K 2 are each independently a direct bond or selected from the group consisting of O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β );

[0015] wherein represents a single bond or a double bond;

[0016] wherein R A , R B , R C , and R D each independently represent mono-substitution to the maximum allowable substitution, or no substitution;

[0017] Wherein each R α , R β , R A , R B , R C and R D is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, selenyl and combinations thereof;

[0018] Wherein any two substituents may be fused or joined to form a ring;

[0019] Wherein any two substituents may be fused or joined to form a ring.

[0020] In another aspect, the present disclosure provides a formulation of a compound as described herein.

[0021] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound as described herein.

[0022] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound as described herein. BRIEF DESCRIPTION OF THE DRAWINGS

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

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

[0025] A. Terms

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

[0027] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as being "disposed on" a second layer "above", the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, there may be other layers between the first and second layers. For example, even if there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed on" the anode "above".

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

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

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

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

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

[0033] In some arrangements, a color - changing layer is provided that converts, modifies, or alters the color of light emitted by another layer into an emission with a different wavelength. This color - changing layer can be formulated to shift the wavelength of the light emitted by another layer by a defined amount, as measured by the difference between the wavelength of the emitted light and the wavelength of the resulting light. Generally, there are two types of color - changing layers: color filters that modify the spectrum by removing light of unwanted wavelengths, and color - changing layers that convert higher - energy photons into lower - energy photons. For example, there can be a "red" filter to filter the input light to remove light outside the wavelength range of about 580 - 700 nm. A "component" of "color" 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 emit two different colors as previously described when activated within a device.

[0034] As used herein, based on the fact that the light initially generated by a material, layer, or region is distinct from the light finally emitted by the same or different structures, emission materials, layers, and regions can be distinguished from each other and from other structures. Initial light generation is typically the result of a change in energy levels that leads to photon emission. For example, an organic emission material can initially generate blue light, which can be converted into red or green light by a color filter, quantum dots, or other structures, such that the complete emission stack or sub - pixel emits red or green light. In this case, the initial emission material, region, or layer can be referred to as a "blue" component, even though the sub - pixel is a "red" or "green" component.

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

[0036]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[0058] The term "heteroaryl" means and includes both monocyclic aromatic groups having at least one heteroatom and polycyclic aromatic ring systems. Heteroatoms include but are not limited to O, S, Se, N, P, B, Si, Ge, and Se. In many cases, O, S, N, or B are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring can have one to six heteroatoms. The polycyclic heterocyclic system can have two or more aromatic rings, where two atoms are common to two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl. The polycyclic heteroaromatic ring system can have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, azaborine, borazine, 5λ 2 ,9λ 2 -diazab-13b-boraphenanthro[2,3,4-de]anthracene, 5λ 2-Benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 5λ 2 ,9λ 2 -diazaboranaphtho[2,3,4-de]anthracene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene. Additionally, the heteroaryl may be further substituted or fused.

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

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

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

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

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

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

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

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

[0067] The "aza" name in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic ring can be replaced by a nitrogen atom. For example, and without any limitation, aza-triphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Those of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be covered by the terms as set forth herein.

[0068] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US2011 / 0037057 (which are incorporated herein by reference in their entireties) describe the preparation of deuterium-substituted organometallic complexes. Further reference to Ming Yan et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Review) 2007, 46, 7744-65 (which are incorporated by reference in their entireties) describe effective routes for the deuteration of methylene hydrogens in benzylamines and for the replacement of aromatic ring hydrogens with deuterium, respectively.

[0069] As used herein, any specifically listed substituent, such as but not limited to methyl, phenyl, pyridyl, etc. includes its non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituents of classes 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 having no valence filled completely by H or D should be considered to include their non-deuterated, partially deuterated, and fully deuterated forms. For example, the chemical structure is meant to include C6H6, C6D6, C6H3D3, and any other of its partially deuterated variants. Some common substantially or fully deuterated groups include but are not limited to CD3, CD2C(CH3)3, C(CD3)3, and C6D5.

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

[0071] In some cases, a pair of substituents in a molecule may optionally be joined or fused into a ring. Preferred rings are five- to nine-membered carbocyclic or heterocyclic rings, including cases where the portion of the ring formed by the pair of substituents is saturated and cases where the portion of the ring formed by the pair of substituents is unsaturated. In still other cases, a pair of adjacent substituents may optionally be joined or fused into 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 neighboring rings having the two closest available substitutable positions (such as the 2,2'-positions in biphenyl or the 1,8-positions in naphthalene).

[0072] B. Compounds of the Present Disclosure

[0073] In one aspect, the present disclosure provides a compound comprising a structure of Formula I:

[0074]

[0075] wherein moieties A, B, C, and D 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;

[0076] wherein M is selected from Pt and Pd;

[0077] wherein X 1 -X 4 are each independently C or N;

[0078] wherein Z 1 -Z 4 are each independently C or N;

[0079] wherein L is a direct bond or an organic linking group having one or two linking atoms;

[0080] wherein K 1 and K 2 are each independently a direct bond or selected from the group consisting of O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β );

[0081] wherein represents a single bond or a double bond;

[0082] wherein R A , R B , R C , and R D each independently represent mono-substitution to the maximum allowable substitution, or no substitution;

[0083] wherein each R α , R β , R A , R B , R C and R DIndependently is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boranyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boranyl, selenyl, and combinations thereof;

[0084] wherein any two substituents may be fused or joined to form a ring; and

[0085] wherein any two substituents may be fused or joined to form a ring.

[0086] In some embodiments, K 1 and K 2 each independently is selected from the group consisting of O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β ).

[0087] In some embodiments, at least one of R A , R B , R C , and R D contains an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P. In some embodiments, at least one R A contains an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P. In some embodiments, at least one R B contains an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P. In some embodiments, at least one R C contains an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P. In some embodiments, at least one R D contains an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P.

[0088] In some embodiments, the compound is not:

[0089]

[0090] In some embodiments, R α , R β , R A , R B , R C , and R DEach is independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio and combinations thereof.

[0091] In some embodiments, the compound consists essentially of Formula I. In some embodiments, the compound has the structure of Formula I.

[0092] In some embodiments of Formula I, R A , R B , R C or R D is at least partially or fully deuterated. In some embodiments, at least one R A is at least partially or fully deuterated. In some embodiments, at least one R B is at least partially or fully deuterated. In some embodiments, at least one R C is at least partially or fully deuterated. In some embodiments, at least one R D is at least partially or fully deuterated. In some embodiments, R α or R β is at least partially or fully deuterated. In some embodiments, at least one of R, R', R α , R β , R A , R B , R C or R D is a substituent selected from the group consisting of the general substituents defined herein.

[0093] In some embodiments, M is Pt.

[0094] In some embodiments, M is Pd.

[0095] In some embodiments, one of K 1 and K 2 is O.

[0096] In some embodiments, one of K 1 and K 2 is a direct bond.

[0097] In some embodiments, one of K 1 and K 2 is O, and the other of K 1 and K 2 is a direct bond.

[0098] In some embodiments, both K 1 and K 2 are O.

[0099] In some embodiments, at least one of Z 1 -Z 4 is N.

[0100] In some embodiments, exactly one of Z 1 -Z 4 is N.

[0101] In some embodiments, at least two of Z 1 -Z 4 are N.

[0102] In some embodiments, exactly two of Z 1 -Z 4 are N.

[0103] In some embodiments, Z 1 is N.

[0104] In some embodiments, Z 2 is N.

[0105] In some embodiments, both Z 1 and Z 3 are N.

[0106] In some embodiments, Z 1 is C.

[0107] In some embodiments, Z 2 is C.

[0108] In some embodiments, both Z 1 and Z 3 are C.

[0109] In some embodiments, both Z 1 and Z 3 are N, and both Z 1 and Z 3 are C.

[0110] In some embodiments, both Z 1 -Z 4 are C.

[0111] In some embodiments, at least one of X 1 -X 4 is N.

[0112] In some embodiments, exactly one of X 1 -X 4 is N.

[0113] In some embodiments, both X 1 -X 4 are C.

[0114] In some embodiments, L is a direct bond or an organic linking group having one or two linking atoms. Thus, the linking group L means a direct bond, or an atom or chemical group that is covalently bonded to both moiety A and moiety D simultaneously. In other words, the linking group L bridges moieties A and D. For calculating the number of linking atoms, only those atoms of a chemical group consisting of two or more atoms that are directly connected bridging atoms are relevant. For example, if the linking group L is NR, only the N atom is relevant for calculating the number of linking atoms, since it is bonded to moieties A and D. In other words, NR is an example of a monoatomic linking group. For example, if the linking group L is an alkylene group (e.g., CRR'-CRR'), only two C atoms are relevant for calculating the number of linking atoms, since they form a direct bridge between moieties A and D. In other words, an alkylene group is an example of a diatomic linking group.

[0115] In some embodiments, L is selected from the group consisting of: a direct bond, O, S, Se, NR, BR, BRR', PR, CR, C=O, C=NR, C=CRR', C=S, CRR', SO, SO2, P(O)R, SiRR', GeRR', alkylene, cycloalkylene, arylene, heteroarylene, and combinations thereof.

[0116] In some embodiments, L is selected from the group consisting of: O, S, Se, NR, BR, BRR', PR, CR, C=O, C=NR, C=CRR', C=S, CRR', SO, SO2, P(O)R, SiRR', GeRR', alkylene, cycloalkylene, arylene, heteroarylene, and combinations thereof, where each R or R' is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof; where any two substituents may be fused or joined to form a ring. In some embodiments, at least one of R or R' is partially or fully deuterated.

[0117] In some embodiments, if K 1 and K 2 one of which is a direct bond and moiety A is a 6-membered ring, then L is a direct bond.

[0118] In some embodiments, if moiety A is a 5-membered ring, then moiety C is a 5-membered ring.

[0119] In some embodiments, L is CR.

[0120] In some embodiments, L is CR, and the R of CR is joined to R A or R D to form a ring.

[0121] In some embodiments, L is a direct bond.

[0122] In some embodiments, at least two of moieties A, B, C, and D are 6-membered rings.

[0123] In some embodiments, at least two of moieties A, B, C, and D are 6-membered aromatic rings.

[0124] In some embodiments, at least two of moieties A, B, C, and D are 6-membered carbocyclic aromatic rings.

[0125] In some embodiments, at least three of moieties A, B, C, and D are 6-membered rings.

[0126] In some embodiments, at least three of moieties A, B, C, and D are 6-membered aromatic rings.

[0127] In some embodiments, at least three of moieties A, B, C, and D are 6-membered carbocyclic aromatic rings.

[0128] In some embodiments, at least one of moieties A, B, C, and D is a 5-membered ring.

[0129] In some embodiments, at least one of moieties A, B, C, and D is a 5-membered aromatic ring.

[0130] In some embodiments, at least one of moieties A, B, C, and D is a 5-membered heteroaromatic ring.

[0131] In some embodiments, at least two of moieties A, B, C, and D are 5-membered rings.

[0132] In some embodiments, at least two of moieties A, B, C, and D are 5-membered aromatic rings.

[0133] In some embodiments, at least two of moieties A, B, C, and D are 5-membered heteroaromatic rings.

[0134] In some embodiments, at least one of moieties A, B, C, and D is a 6-membered ring.

[0135] In some embodiments, at least one of moieties A, B, C, and D is a 6-membered aromatic ring.

[0136] In some embodiments, at least one of moieties A, B, C, and D is a 6-membered heteroaromatic ring.

[0137] In some embodiments, exactly two of moieties A, B, C, and D are 6-membered rings.

[0138] In some embodiments, exactly two of moieties A, B, C, and D are 6-membered aromatic rings.

[0139] In some embodiments, exactly two of moieties A, B, C, and D are 6-membered heteroaromatic rings.

[0140] In some embodiments, moieties A, B, C, and D are all 6-membered rings.

[0141] In some embodiments, moieties A, B, C, and D are all 6-membered aromatic rings.

[0142] In some embodiments, moiety A is a 6-membered ring.

[0143] In some embodiments, moiety A is a 6-membered aromatic ring.

[0144] In some embodiments, moiety A is a 6-membered heteroaromatic ring.

[0145] In some embodiments, moiety A is a 6-membered carbocyclic aromatic ring.

[0146] In some embodiments, moiety B is a 6-membered ring.

[0147] In some embodiments, moiety B is a 6-membered aromatic ring.

[0148] In some embodiments, moiety B is a 6-membered carbocyclic aromatic ring.

[0149] In some embodiments, moiety B is a 6-membered heteroaromatic ring.

[0150] In some embodiments, moiety B is a 5-membered ring.

[0151] In some embodiments, moiety B is a 5-membered aromatic ring.

[0152] In some embodiments, moiety B is a 5-membered heteroaromatic ring.

[0153] In some embodiments, moiety C is a 6-membered ring.

[0154] In some embodiments, moiety C is a 6-membered aromatic ring.

[0155] In some embodiments, moiety C is a 6-membered carbocyclic aromatic ring.

[0156] In some embodiments, moiety C is a 6-membered heteroaromatic ring.

[0157] In some embodiments, moiety C is a 5-membered ring.

[0158] In some embodiments, moiety C is a 5-membered aromatic ring.

[0159] In some embodiments, moiety C is a 5-membered heteroaromatic ring.

[0160] In some embodiments, moiety D is a 6-membered ring.

[0161] In some embodiments, moiety D is a 6-membered aromatic ring.

[0162] In some embodiments, moiety D is a 6-membered carbocyclic aromatic ring.

[0163] In some embodiments, moiety D is a 6-membered heteroaromatic ring.

[0164] In some embodiments, moiety D is a 5-membered ring.

[0165] In some embodiments, moiety D is a 5-membered aromatic ring.

[0166] In some embodiments, moiety D is a 5-membered heteroaromatic ring.

[0167] In some embodiments, moiety A is independently selected from the group consisting of the following list of cyclic moieties: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0168] In some embodiments, moiety A is a monocyclic ring.

[0169] In some embodiments, moiety A is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0170] In some embodiments, moiety A is pyridine or imidazole.

[0171] In some embodiments, moiety A is a polycyclic fused ring system.

[0172] In some embodiments, moiety A is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0173] In some embodiments, moiety A is benzimidazole.

[0174] In some embodiments, moiety B is independently selected from the group consisting of the following list of cyclic moieties: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0175] In some embodiments, moiety B is monocyclic.

[0176] In some embodiments, moiety B is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0177] In some embodiments, moiety B is pyridine or imidazole.

[0178] In some embodiments, moiety B is a polycyclic fused ring system.

[0179] In some embodiments, moiety B is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0180] In some embodiments, moiety B is benzimidazole.

[0181] In some embodiments, moiety C is independently selected from the group consisting of the following list of cyclic moieties: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0182] In some embodiments, moiety C is monocyclic.

[0183] In some embodiments, moiety C is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0184] In some embodiments, moiety C is pyridine or imidazole.

[0185] In some embodiments, moiety C is a polycyclic fused-ring system.

[0186] In some embodiments, moiety C is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0187] In some embodiments, moiety C is benzimidazole.

[0188] In some embodiments, moiety D is independently selected from the group consisting of the following list of cyclic moieties: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0189] In some embodiments, moiety D is monocyclic.

[0190] In some embodiments, moiety D is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0191] In some embodiments, moiety D is pyridine or imidazole.

[0192] In some embodiments, moiety D is a polycyclic fused ring system.

[0193] In some embodiments, moiety D is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, benzimidazole-derived carbene, aza-benzimidazole, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0194] In some embodiments, moiety D is benzimidazole.

[0195] In some embodiments, at least two Rs A are joined to form a fused polycyclic moiety including moiety A.

[0196] In some embodiments, at least two Rs A are joined to form a 5-membered ring fused to moiety A.

[0197] In some embodiments, at least two Rs A are joined to form a 5-membered aromatic ring fused to moiety A.

[0198] In some embodiments, at least two Rs A are joined to form a 5-membered aromatic heterocycle fused to moiety A.

[0199] In some embodiments, at least two Rs B are joined to form a fused polycyclic moiety including moiety B.

[0200] In some embodiments, at least two Rs B are joined to form a 5-membered ring fused to moiety B.

[0201] In some embodiments, at least two Rs B are joined to form a 5-membered aromatic ring fused to moiety B.

[0202] In some embodiments, at least two Rs B are joined to form a 5-membered aromatic heterocycle fused to moiety B.

[0203] In some embodiments, the compound comprises at least two atoms selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P.

[0204] In some embodiments, the compound comprises at least two atoms selected from the group consisting of B, Si, Ge, S, Se, and P.

[0205] In some embodiments, R A , R B , R C and R D At least one of the comprises at least one deuterium atom.

[0206] In some embodiments, R A , R B , R C and R D At least two of them are deuterium atoms.

[0207] In some embodiments, R A , R B , R C and R D At least three of them are deuterium atoms.

[0208] In some embodiments, R A , R B , R C and R D At least four of them are deuterium atoms.

[0209] In some embodiments, R A At least two of R B Two of them, R C Two or R D Two of them are deuterium atoms.

[0210] In some embodiments, R A At least three of R B Three of them, R C Three or R D Three of them are deuterium atoms.

[0211] In some embodiments, R A At least four of R B Four of them, R C Four or R D Four of them are deuterium atoms.

[0212] In some embodiments, R A , R B , R C and R D At least one of the comprises at least three deuterium atoms.

[0213] In some embodiments, R A , R B , R C and R D At least one of the comprises at least four deuterium atoms.

[0214] In some embodiments, RA , R B , R C and R D at least one of them contains at least one B atom.

[0215] In some embodiments, R A , R B , R C and R D at least one of them contains at least one Si atom.

[0216] In some embodiments, R A , R B , R C and R D at least one of them contains at least two Si atoms.

[0217] In some embodiments, R A , R B , R C and R D at least one of them contains at least one Ge atom.

[0218] In some embodiments, R A , R B , R C and R D at least one of them contains at least one S atom.

[0219] In some embodiments, R A , R B , R C and R D at least one of them contains at least one Se atom.

[0220] In some embodiments, R A , R B , R C and R D at least one of them contains at least one P atom.

[0221] In some embodiments, at least one atom selected from the group consisting of B, Si, Ge, S, Se, and P is directly bonded to one of moieties A, B, C, or D.

[0222] In some embodiments, if moiety A is a 5-membered ring, then moiety C or moiety D is a 5-membered ring.

[0223] In some embodiments, when moiety A is an N-heterocyclic carbene, then moiety C or moiety D is an N-heterocyclic carbene or an imidazole.

[0224] In some embodiments, when moieties A and D are 5-membered rings, moiety D contains at least two non-adjacent heteroatoms and L is selected from the group consisting of: O, S, Se, NR, BR, BRR', PR, CR, C═O, C═NR, C═CRR', C═S, CRR', SO, SO2, P(O)R, SiRR', GeRR', alkylene, cycloalkylene, arylene, heteroarylene, and combinations thereof.

[0225] In some embodiments, when K 1 and K 2 one of which is a direct bond and moiety A is a 6-membered ring, then L is a direct bond.

[0226] In some embodiments, when K 1 and K 2 are both O and L is CH2, then R A 、R B 、R C and R D do not contain BPh2.

[0227] In some embodiments, when K 1 and K 2 are both O, then L is not CH2.

[0228] In some embodiments, when K 1 and K 2 are both O, then L is selected from the group consisting of: O, S, Se, NR, BR, BRR', PR, CR, C═O, C═NR, C═CRR', C═S, CRR', SO, SO2, P(O)R, SiRR', GeRR', alkylene, cycloalkylene, arylene, heteroarylene, and combinations thereof.

[0229] In some embodiments, when R A 、R B 、R C or R D contains boron, then the boron atom is contained in the ring.

[0230] In some embodiments, any one of R A 、R B 、R C and R D contains deuterium, B, Si, Ge, S, Se, or P atoms that are not fused to any of moieties A, B, C, and D to form a polycyclic structure.

[0231] In some embodiments, moiety B is a 5-membered ring and moieties A, C, and D are 6-membered rings.

[0232] In some embodiments, the compound is selected from those having the formula Pt(LA' a group consisting of compounds of (Ly):

[0233]

[0234] wherein L A' is selected from the group consisting of the structures shown in Lists 1 and 2 below:

[0235] List 1:

[0236]

[0237] List 2:

[0238]

[0239]

[0240] wherein L y is selected from the group consisting of the structures shown in Lists 3 and 4 below:

[0241] List 3:

[0242]

[0243] List 4:

[0244]

[0245]

[0246] wherein when L A' is from List 1, Ly is from Lists 3 and 4;

[0247] wherein when L A' is from List 2, Ly is from List 3; and

[0248] R CC , R G , R", and R''' are independently hydrogen or substituents selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boranyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boranyl, selenyl, and combinations thereof; and

[0249] wherein any two substituents may be fused or joined to form a ring.

[0250] In some embodiments, R A , R B , R C , RCC and R D and R G at least one of R, R', R", and R''' is selected from R203 - R445 in List 11.

[0251] In some embodiments, each R A and R B and R C and R CC and R D and R G and R, R', R", and R''' are independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boranyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boranyl, selenyl, and combinations thereof.

[0252] In some embodiments, each R A and R B and R C and R CC and R D and R G and R, R', R", and R''' are independently selected from the group consisting of the structures defined in List 11.

[0253] In some embodiments, the compound is selected from the group consisting of compounds having the formula Pt(L A' )(Ly):

[0254]

[0255] wherein L A' is selected from the group consisting of L A' W 1 -(Ri)(Rj)(Rk)(Rl), where W 1 is an integer from 1 to 40, where i, j, k, l are each independently integers from 1 to 445, each Ri, Rj, Rk, and Rl is independently selected from R1 - R445, at least one of Ri, Rj, Rk, Rl is selected from R203 - R445, wherein L A' 1-(R1)(R1)(R1)(R1) to L A' 4-(R445)(R445)(R445)(R445) is shown in List 7, and L A' 5-(R1)(R1)(R1)(R1) to L A' 40-(R445)(R445)(R445)(R445) is shown in List 8:

[0256] Listing 7:

[0257]

[0258] Listing 8:

[0259]

[0260]

[0261]

[0262]

[0263] wherein L y is selected from the group consisting of L y Z 1 -(Rs)(Rt)(Ru)(Rv), wherein Z 1 is an integer from 1 to 22, wherein s, t, u, and v are each independently integers from 1 to 445, and each of Rs, Rt, Ru, and Rv is independently selected from R1 to R445, and at least one of Rs, Rt, Ru, and Rv is selected from R203 - R445; L y 1-(R1)(R1)(R1)(R1) to L y 3-(R445)(R445)(R445)(R445) as defined in Listing 9, and L y 4-(R1)(R1)(R1)(R1) to L y 22-(R445)(R445)(R445)(R445) as defined in Listing 10:

[0264] Listing 9:

[0265]

[0266] Listing 10:

[0267]

[0268]

[0269] wherein when L A' is from Listing 7, Ly is from Listing 9 and Listing 10;

[0270] wherein when L A' is from Listing 8, Ly is from Listing 9;

[0271] wherein R1 to R445 have the following structure as defined in the following Listing 11:

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] In some embodiments, the compound is selected from the group consisting of the structures in the following Listing 12:

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently a polycyclic fused-ring structure. In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently a polycyclic fused-ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused-ring structure has two 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M, and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and their N-heterocyclic variants. In some such embodiments, each of moiety A, moiety B, moiety C, and moiety D can be independently further substituted at the ortho or meta position of the O, S, or Se atom with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the N-heterocyclic variant contains exactly one N atom at the 6-position (ortho to O, S, or Se) and has a substituent at the 7-position (meta to O, S, or Se).

[0300] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently a polycyclic fused-ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused-ring structure comprises three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0301] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently a polycyclic fused-ring structure comprising at least five fused rings. In some embodiments, the polycyclic fused-ring structure comprises four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments having two 5-membered rings, the 5-membered rings are fused together. In some embodiments having two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments having one 5-membered ring, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, the third 6-membered ring is fused to the second 6-membered ring, and the fourth 6-membered ring is fused to the third 6-membered ring.

[0302] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D is independently an aza form of the polycyclic fused ring described above. In some such embodiments, each of moiety A, moiety B, moiety C, and moiety D independently contains exactly one aza N atom. In some such embodiments, each of moiety A, moiety B, moiety C, and moiety D contains exactly two aza N atoms, which two aza N atoms may be in one ring or in two different rings. In some such embodiments, the ring having an aza N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring having an aza N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each of the ortho positions of the aza N atom is substituted.

[0303] In some embodiments, the compound comprises an electron-withdrawing group. In some embodiments, the Hammett constant of the electron-withdrawing group is greater than 0. In some embodiments, the Hammett constant of the electron-withdrawing group is equal to or greater than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.

[0304] In some embodiments, the compound comprises an electron-withdrawing group selected from the group consisting of the following EWG1 list: F, CF3, CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3, (R k2 )2CCN, (R k2 )2CCF3, CNC(CF3)2, BR k3 R k2 , substituted or unsubstituted dibenzoborolene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridoxine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated alkyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing alkyl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,

[0305] Wherein each R k1 represents mono-substitution to the maximum allowable substitution or no substitution;

[0306] Wherein Y G is selected from the group consisting of: BR e 、NR e 、PR e 、O, S, Se, C═O, S═O, SO2, CR e R f 、SiR e R f and GeR e R f ; and

[0307] R k1 、R k2 、R k3 、R e and R f each independently is hydrogen or a substituent selected from the group of general substituents defined herein.

[0308] In some embodiments, the compound comprises an electron-withdrawing group selected from the group consisting of the structures in the following EWG2 list:

[0309]

[0310]

[0311] In some embodiments, the compound comprises an electron-withdrawing group selected from the group consisting of the structures in the following EWG3 list

[0312]

[0313]

[0314] In some embodiments, the compound comprises an electron-withdrawing group selected from the group consisting of the structures in the following EWG4 list

[0315]

[0316] In some embodiments, the compound comprises an electron-withdrawing group, which is a π-deficient electron-withdrawing group. In some embodiments, the π-deficient electron-withdrawing group is selected from the group consisting of the structures in the following π-EWG list: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, + N(R k2 )3, BR k2 R k3 , substituted or unsubstituted dibenzoborolene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,

[0317] and wherein the variables are the same as those defined previously.

[0318] In some embodiments, the compound comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0319] In some embodiments, at least one R A is or comprises an electron-withdrawing group. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R Ais or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0320] In some embodiments, at least one R B is or comprises an electron-withdrawing group. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R B is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0321] In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R C is or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0322] In some embodiments, at least one R D is or comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R D is or comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R D is or comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R D is or comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R Dis or comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0323] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can be 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, benzobenzimidazole, aza-benzobenzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0324] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be a polycyclic fused-ring structure. In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be a polycyclic fused-ring structure comprising at least two fused rings. In some embodiments, the polycyclic fused-ring structure has a 6-membered ring and a 5-membered ring. In some such embodiments, the 5-membered ring or the 6-membered ring can coordinate to a metal. In some embodiments, the polycyclic fused-ring structure has two 6-membered rings. In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be selected from the group consisting of benzofuran, benzothiophene, benzoselenophene, naphthalene, and their aza-variants.

[0325] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D 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 a 5-membered ring. In some such embodiments, the 5-membered ring is fused to a ring coordinated to metal M, and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and their aza-variants. In some such embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be further substituted at the ortho or meta position of an O, S, or Se atom with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza-variant contains exactly one N atom at the 6-position (ortho to O, S, or Se) and has a substituent at the 7-position (meta to O, S, or Se).

[0326] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be a polycyclic fused-ring structure containing at least four fused rings. In some embodiments, the polycyclic fused-ring structure contains three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted with a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0327] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be a polycyclic fused-ring structure containing at least five fused rings. In some embodiments, the polycyclic fused-ring structure contains four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments containing two 5-membered rings, the 5-membered rings are fused together. In some embodiments containing two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments having one 5-membered ring, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, the third 6-membered ring is fused to the second 6-membered ring, and the fourth 6-membered ring is fused to the third 6-membered ring.

[0328] In some embodiments, each of moiety A, moiety B, moiety C, and moiety D can independently be an aza version of the polycyclic fused-ring described above. In some such embodiments, at least one of moiety A, moiety B, moiety C, and moiety D can independently contain exactly one aza N atom. In some such embodiments, at least one of moiety A, moiety B, moiety C, and moiety D contains exactly two aza N atoms, which two aza N atoms can be in one ring or in two different rings. In some such embodiments, the ring having the aza N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring having the aza N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each of the ortho positions of the aza N atom is substituted.

[0329] In some embodiments, a compound having the structure of Formula I described herein can be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, the percentage of deuteration has its ordinary meaning and includes the percentage of all possible hydrogen atoms (e.g., positions of hydrogen or deuterium) occupied by deuterium atoms in the compound. In some embodiments, the carbon atoms constituting the ring coordinated to metal M are fully or partially deuterated. In some embodiments, the carbon atoms contained in the polycyclic system coordinated to metal M are fully or partially deuterated. In some embodiments, the substituents attached to the monocyclic or fused polycyclic system coordinated to metal M are fully or partially deuterated.

[0330] In some embodiments, the emission of the compound of Formula I at room temperature has a full width at half maximum (FWHM) equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.

[0331] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emission via phosphorescence, fluorescence, thermally activated delayed fluorescence, triplet-triplet annihilation, or a combination of these methods. In some embodiments, the emissive dopant can be a racemic mixture or can be enriched in one enantiomer. In some embodiments, the compounds of the present invention can have different stereoisomers, such as fac and mer. The present compounds relate to individual isomers and mixtures of various isomers in any mixing ratio. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (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 the other ligands. In some embodiments, each ligand can be different from all other ligands. This also holds in embodiments where the ligands coordinated to the metal can be connected to other ligands coordinated to the metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, in cases where the coordinated ligands are connected together, in some embodiments, all ligands can be the same, and in some other embodiments, at least one of the connected ligands can be different from the other ligands.

[0332] In yet another aspect of the present disclosure, a formulation comprising a novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of solvents, emitters, hosts, hole injection materials, hole transport materials, electron blocking materials, hole blocking materials, and electron transport materials disclosed herein.

[0333] The present disclosure encompasses any chemical structure that includes 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, a "monovalent variant of a compound" refers to the same moiety as the compound, but in which one hydrogen has been removed and replaced with a bond that attaches to the remainder of the chemical structure. As used herein, a "multivalent variant of a compound" refers to the same moiety as the compound, but in which more than one hydrogen has been removed and replaced with one or more bonds that attach to the remainder of the chemical structure. In the case of a supramolecule, the compounds of the present invention can also be incorporated into the supramolecular complex without a covalent bond. As used in this context, the description that structure A contains moiety B means that structure A includes the structure of moiety B, and the structure of moiety B does not include H or D atoms that can be attached to moiety B. This is because at least one H or D on the given moiety structure must be replaced with a substituent such that moiety B can be part of structure A, and after it becomes part of structure A, one or more of the H or D on the given moiety B structure can be further substituted.

[0334] C. OLEDs and Devices of the Present Disclosure

[0335] In another aspect, the present disclosure also provides an OLED device that includes a first organic layer containing a compound as disclosed in the above compound moiety of the present disclosure.

[0336] In some embodiments, the OLED includes: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compounds described herein.

[0337] In some embodiments, the organic layer is selected from the group consisting of: HIL, HTL, EBL, EML, HBL, ETL, and EIL. In some embodiments, the organic layer can be an emissive layer and the compounds as described herein can be emissive dopants or non-emissive dopants.

[0338] In some embodiments, the organic layer can further include a host, wherein the host contains at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2-Benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boraphenanthro[3,2,1-de]anthracene, azacyclohexaborane, oxaborole, dihydroacridine, xanthene, dihydrobenzoazasiline, dibenzooxasiline, phenoxazine, phenoxathiin, phenothiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, silyl, 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-boraphenanthro[3,2,1-de]anthracene).

[0339] In some embodiments, the host may be selected from the group consisting of the structures in Host Group 1 below:

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349] Wherein:

[0350] Each of J1 to J6 is independently C or N;

[0351] L' is a direct bond or an organic linking group;

[0352] Each Y AA 、Y BB 、Y CC and Y DD is independently selected from the group consisting of: no bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0353] R A '、R B '、R C '、R D '、R E '、R F ' and R G ' each independently represents mono - substitution, up to maximum substitution or no substitution;

[0354] Each R, R', R A '、R B '、R C '、R D '、R E '、R F ' and R G ' are independently hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring;

[0355] And, where possible, each unsubstituted aromatic carbon atom is optionally replaced by N to form a nitrogen - substituted ring.

[0356] In some embodiments, at least one of J1 to J3 is N. In some embodiments, at least two of J1 to J3 are N. In some embodiments, all three of J1 to J3 are N. In some embodiments, each Y CC and Y DD are independently O, S or SiRR', or more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen - containing ring.

[0357] In some embodiments, the host is selected from the group consisting of: EG1 - MG1 - EG1 to EG53 - MG27 - EG53 having the formula EGa - MGb - EGc, or EG1 - EG1 to EG53 - EG53 having the formula EGa - EGc when MGb is absent, where a is an integer from 1 to 53, b is an integer from 1 to 27, and c is an integer from 1 to 53. The structures of EG1 to EG53 are shown below:

[0358]

[0359]

[0360] The structures of MG1 to MG27 are shown below:

[0361]

[0362] In the MGb structure shown above, two bonding positions in the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24, and MG25 are marked with numbers for identification purposes.

[0363] In some embodiments, the host may be any one of its N - substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the host has the formula EGa - MGb - Egc and is selected from the group consisting of h1 to h112 as defined in the following list of Group 2 of hosts, where each of MGb, EGa, and Egc is defined as follows:

[0364]

[0365]

[0366] In the table above, the EGa and Egc structures bonded to one of the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24, and MG25 are labeled with a numerical prefix that identifies their bonding position in the MGb structure.

[0367] In some embodiments, the organic layer may further comprise a host, wherein the host comprises a metal complex.

[0368] In some embodiments, the emissive layer may comprise two hosts: a first host and a second host. In some embodiments, the first host is a hole-transporting host and the second host is an electron-transporting host. In some embodiments, the first host is a hole-transporting host and the second host is a bipolar host. In some embodiments, the first host is an electron-transporting host and the second host is a bipolar host. In some embodiments, the first host and the second host may form an exciplex. In some embodiments, the emissive layer may comprise a third host. In some embodiments, the third host is selected from the group consisting of: an insulating host (wide-bandgap host), a hole-transporting host, and an electron-transporting host. In some embodiments, the third host forms an exciplex with one of the first host and the second host or with both the first host and the second host. In some embodiments, the emissive layer may comprise a fourth host. In some embodiments, the fourth host is selected from the group consisting of: an insulating host (wide-bandgap host), a hole-transporting host, and an electron-transporting host. In some embodiments, the fourth host forms an exciplex with one of the first host, the second host, and the third host, with two of the first host, the second host, and the third host, or with each of the first host, the second host, and the third host. In some embodiments, the LUMO of the electron-transporting host is less than -2.4 eV, less than -2.5 eV, less than -2.6 eV, or less than -2.7 eV. In some embodiments, the HOMO of the hole-transporting host is higher than -5.6 eV, higher than -5.5 eV, higher than -5.4 eV, or higher than -5.35 eV. The HOMO and LUMO values can be determined electrochemically in solution. Cyclic voltammetry and differential pulse voltammetry in solution can be performed using a CH Instruments Model 6201B potentiostat, using anhydrous dimethylformamide (DMF) solvent and tetrabutylammonium hexafluorophosphate as the supporting electrolyte. Glassy carbon, platinum wire, and silver wire are used as the working electrode, counter electrode, and reference electrode, respectively. By measuring the peak potential difference by differential pulse voltammetry, the electrochemical potential can be referenced to the internal ferrocene-ferrocenium redox couple (Fc / Fc+).According to the literature ((a) Fink R., Heischkel Y., Thelakkat M., Schmidt H.-W., Chem. Mater. 1998, 10, 3620 - 3625; (b) Pommerehne J., Vestweber H., Guss W., Mahrt R.F., Bassler H., Porsch M., Daub, J. Adv. Mater. 1995, 7, 551), the corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies are determined by setting the cationic and anionic redox potentials relative to the ferrocene reference (4.8 eV relative to vacuum).

[0369] In some embodiments, the compounds as described herein can be a sensitizer or a component of a sensitizer; wherein the device can further comprise an acceptor that receives energy from the sensitizer. In some embodiments, the acceptor is an emitter in the device. In some embodiments, the acceptor can be a fluorescent material. In some embodiments, the compounds as described herein can be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain an acceptor in the form of one or more non - delayed fluorescence and / or delayed fluorescence materials. In some embodiments, the compounds as described herein can be used as a component of an exciplex that serves 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 the energy to a final emitter. The acceptor concentration can range from 0.001% to 99.9%. 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 thermally activated delayed fluorescence (TADF) material. In some embodiments, the acceptor is a non - delayed fluorescence material. In some embodiments, the emission can be generated by any one or all of the sensitizer, the acceptor, and the final emitter. In some embodiments, the emission of the acceptor at room temperature has a full width at half maximum (FWHM) equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.

[0370] As used herein, phosphorescence generally refers to photon emission when there is a change in the electron spin quantum number, i.e., the initial and final states of the emission have different electron spin quantum numbers, such as from the T1 to the S0 state. Most of the Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, if the exciplex formation involves a triplet emitter, such exciplexes can also emit phosphorescence. On the other hand, fluorescent emitters generally refer to photon emission when the electron spin quantum number remains unchanged, such as from the S1 to the S0 state, or from the D1 to the D0 state. Fluorescent emitters can be delayed fluorescence or non-delayed fluorescence emitters. Depending on the spin state, fluorescent emitters can be singlet emitters or doublet emitters or other multiplet emitters. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the thermal population between the triplet and the singlet excited state. Thermal energy can activate the triplet transition back to the singlet. This type of delayed fluorescence is also known as TADF. E-type delayed fluorescence characteristics can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that TADF emission requires a compound or exciplex with a small singlet-triplet energy gap (ΔE S-T ) less than or equal to 400, 350, 300, 250, 200, 150, 100, or 50 meV. There are two main types of TADF emitters, one called donor-acceptor type TADF and the other called multi-resonant (MR) TADF. Generally, single compound donor-acceptor TADF compounds are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) and an electron acceptor moiety (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). A donor-acceptor exciplex can be formed between a hole transporting compound and an electron transporting compound. Examples of MR-TADF materials include highly conjugated fused ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials can also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 for delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, such time can be greater than 10 microseconds and less than 100 microseconds.

[0371] In some embodiments, the OLED can include additional compounds selected from the group consisting of: non-delayed fluorescent materials, delayed fluorescent materials, phosphorescent materials, and combinations thereof.

[0372] In some embodiments, the inventive compounds described herein are phosphorescent materials.

[0373] In some embodiments, the phosphorescent material is an emitter that emits light within the OLED. In some embodiments, the phosphorescent material does not emit light within the OLED. In some embodiments, the phosphorescent material transfers its excited state energy to another material within the OLED. In some embodiments, the phosphorescent material participates in charge transport within the OLED. In some embodiments, the phosphorescent material is a sensitizer or a component of a sensitizer, and the OLED further includes a receptor. In some embodiments, the phosphorescent material forms an exciplex with another material (such as a host material, an emitter material) within the OLED.

[0374] In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material is an emitter that emits light within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material does not emit light within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material transfers its excited state energy to another material within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material participates in charge transport within the OLED. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material is a receptor, and the OLED further includes a sensitizer.

[0375] In some embodiments of the OLED, the delayed fluorescent material includes at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescent material is a metal complex. In some embodiments, the delayed fluorescent material is a non-metal complex. In some embodiments, the delayed fluorescent material is a Pt, Pd, Zn, Cu, Ag, or Au complex (some of which are also referred to as metal-assisted (MA) TADF). In some embodiments, the metal-assisted delayed fluorescent material includes a metal-carbene bond. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material includes at least one chemical group selected from the group consisting of: aryl-amine, aryloxy, arylthio, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boraperylene[3,2,1-de]anthracene, 5λ 2 ,9λ 2 -diazaborylene[2,3,4-de]anthracene, 5-oxa-9λ 2-aza-13b-boraphenanthro[3,2,1-de]anthracene, azaborinane, oxaborole, dihydroacridine, xanthene, dihydrobenzazasilole, dibenzooxasilole, phenoxazine, phenoxathiin, phenothiazine, dihydro-phenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, amino, silyl, their aza-variants, and combinations thereof. In some embodiments, the non-delayed fluorescence material or the delayed fluorescence material comprises tris(aryl / heteroaryl)borane, wherein one or more pairs of substituents from the aryl / heteroaryl are joined to form a ring. In some embodiments, the fluorescent material comprises at least one chemical group selected from the group consisting of naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene, and azulene.

[0376] In yet another aspect, the OLEDs of the present disclosure may further comprise an emissive region containing a compound or a formulation of compounds as disclosed in the above compound portions of the present disclosure. In some embodiments, the emissive region may comprise a compound or a formulation of compounds as described herein. In some embodiments, the emissive region consists of one or more organic layers, wherein at least one of the one or more organic layers has a minimum thickness selected from the group consisting of 350, 400, 450, 500, 550, 600, 650, and In some embodiments, at least one of the one or more organic layers is formed of an emission system having a figure of merit (FOM) equal to or greater than a value selected from the group consisting of 2.50, 2.55, 2.60, 2.65, 2.70, 2.75, 2.80, 2.85, 2.90, 2.95, 3.00, 5.00, 10.0, 15.0, and 20.0. The definition of FOM can be obtained from U.S. Patent Application Publication No. 2023 / 0292605, the entire content of which is incorporated herein by reference. In some embodiments, at least one of the one or more organic layers comprises a compound or a formulation of compounds as disclosed in Part A and Part D of the present disclosure.

[0377] In some embodiments, the OLEDs or emissive regions containing the compounds of the present invention disclosed herein can be incorporated into a full-color pixel arrangement of a device. The full-color pixel arrangement of such a device includes at least one pixel, wherein the at least one pixel includes a first sub-pixel and a second sub-pixel. The first sub-pixel includes a first OLED, and the first OLED includes a first emissive region. The second sub-pixel includes a second OLED, and the second OLED includes a second emissive region. In some embodiments, the first and / or second OLEDs, the first and / or second emissive regions can be the same or different and each can independently have various device features and various embodiments of the compounds of the present invention included therein, as well as various combinations and sub-combinations of various device features and various embodiments of the compounds of the present invention included therein, as disclosed herein.

[0378] In some embodiments, the first emissive region is configured to emit light having a peak wavelength λ max1 ; the second emissive region is configured to emit light having a peak wavelength λ max2 . In some embodiments, the difference between the peak wavelength λ max1 and λ max2 is at least 4 nm but within the same color. For example, light of light blue and dark blue as described above. In some embodiments, the first emissive region is configured to emit light having a peak wavelength λ max1 in one region of the visible spectrum of 400 - 500 nm, 500 - 600 nm, 600 - 700 nm; and the second emissive region is configured to emit light having a peak wavelength λ max2 in one of the remaining regions of the visible spectrum of 400 - 500 nm, 500 - 600 nm, 600 - 700 nm. In some embodiments, the first emissive region includes (if more than one) a first number of emissive layers deposited one above the other; and the second emissive region includes (if more than one) a second number of emissive layers deposited one above the other; and the first number is different from the second number. In some embodiments, both the first emissive region and the second emissive region include phosphorescent materials that can be the same or different. In some embodiments, the first emissive region includes a phosphorescent material, while the second emissive region includes a fluorescent material. In some embodiments, both the first emissive region and the second emissive region include fluorescent materials that can be the same or different.

[0379] In some embodiments, at least one pixel of the OLED or emission region includes a total of N sub-pixels; where the N sub-pixels include a first sub-pixel and a second sub-pixel; where each of the N sub-pixels includes an emission region; and where the total number of emission regions within at least one pixel is equal to or less than N-1. In some embodiments, the second emission region is identical to the first emission region; and each sub-pixel of at least one pixel includes one emission region identical to the first emission region. In some embodiments, the full-color pixel arrangement may have a plurality of pixels including a first pixel region and a second pixel region; where at least one display characteristic of the first pixel region is different from the corresponding display characteristic of the second pixel region, and where at least one display characteristic is selected from the group consisting of: resolution, cavity mode, color, out-coupling, and color filter.

[0380] In some embodiments, the OLED is a stacked OLED including one or more charge generation layers (CGLs). In some embodiments, the OLED includes a first electrode, a first emission region disposed above the first electrode, a first CGL disposed above the first emission region, a second emission region disposed above the first CGL, and a second electrode disposed above the second emission region. In some embodiments, the first emission region and / or the second emission region may have various device characteristics as described above for the pixelated device. In some embodiments, the stacked OLED is configured to emit white light. In some embodiments, one or more of the emission regions in the pixelated OLED or the stacked OLED include a sensitizer and a receptor having various sensitization device characteristics and various embodiments of the inventive compounds disclosed herein. For example, the first emission region is included in the sensitization device while the second emission region is not included in the sensitization device; in some cases, both the first emission region and the second emission region are included in the sensitization device.

[0381] In some embodiments, the OLED can emit at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99%, or 100% of the light from the plasmon mode. In some embodiments, at least one of the anode, the cathode, or a new layer disposed above the organic emissive layer serves as an enhancement layer. The enhancement layer includes a plasmonic material that exhibits surface plasmon resonance, the plasmonic material being non-radiatively coupled to the emitter material and transferring the excited state energy from the emitter material to the non-radiative mode of the surface plasmon polaritons. In some embodiments, the enhancement layer is disposed at a distance from the organic emissive layer that does not exceed a threshold distance, where, due to the presence of the enhancement layer, the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant. The threshold distance is the position where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. Another threshold distance is the distance at which the total radiative decay rate constant divided by the sum of the total non-radiative decay rate constant and the total radiative decay rate constant is equal to the photoluminescence yield of the emitter material in the absence of the enhancement layer.

[0382] In some embodiments, the OLED further includes an out-coupling layer. In some embodiments, the out-coupling layer is disposed on the side opposite the organic emissive layer above the enhancement layer. The out-coupling layer scatters the energy from the surface plasmon polaritons. In some embodiments, this energy is scattered as photons into free space. In other embodiments, the energy is scattered from the surface plasmon mode of the device into other modes, such as but not limited to organic waveguide modes, substrate modes, or another waveguide mode. In some embodiments, one or more intermediate layers can be disposed between the enhancement layer and the out-coupling layer. Examples of the intermediate layer can be dielectric materials, including organic, inorganic, perovskite, oxides, and can include stacks and / or mixtures of these materials.

[0383] The enhancement layer changes the effective properties of the medium in which the emitter material resides, thereby causing any one or all of the following: reduced emissivity, changed emission line shape, angular variation of emission intensity, changed emitter material stability, changed OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both sides, or placing the enhancement layer itself as a CGL produces an OLED device that utilizes any of the above effects. In addition to the specific functional layers described in the various OLED examples mentioned herein and illustrated in the figures, the OLEDs according to the present disclosure can also include any other functional layers common in OLEDs.

[0384] In some embodiments, the enhancement layer can comprise a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. In some embodiments, the plasmonic material includes at least one metal. In such embodiments, the metal can include at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, or Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has features of wavelength size arranged periodically, quasi-periodically, or randomly, or features of sub-wavelength size arranged periodically, quasi-periodically, or randomly.

[0385] In some embodiments, the out-coupling layer has features of wavelength size or sub-wavelength size arranged periodically, quasi-periodically, or randomly. In some embodiments, the out-coupling layer can be composed of a plurality of nanoparticles. In some embodiments, the out-coupling layer is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the out-coupling layer can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer, or changing the material of the enhancement layer. The plurality of nanoparticles of the device can be formed from at least one of the following: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stack or layer of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the out-coupling layer is composed of at least metal nanoparticles, where the metal is selected from the group consisting of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the out-coupling layer is formed by lithography.

[0386] In some embodiments of the plasmonic device, the emitter and / or host compound used in the emission layer has a vertical dipole ratio (VDR) of 0.33 or greater. In some such embodiments, the emitter and / or host compound has a VDR of 0.40, 0.50, 0.60, 0.70, or greater.

[0387] In yet another aspect, the present disclosure also provides a consumer product that includes an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, where the organic layer can include a compound or formulation of compounds as disclosed in the above compound portion of the present disclosure.

[0388] In some embodiments, a consumer product includes an OLED having an anode; a cathode; and an organic layer disposed between the anode and the cathode, where the organic layer can include a compound as described herein.

[0389] Generally, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the electrode of opposite charge. When an electron and a hole are located on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. When the exciton relaxes through a light-emitting mechanism, light is emitted. In some cases, the exciton can be localized as an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, can also occur but are generally considered undesirable.

[0390] Figure 1 An organic light-emitting device 100 is shown. The figure is not necessarily drawn to scale. Device 100 can include a substrate 110, an anode 115, a hole injection layer (HIL) 120, a hole transport layer (HTL) 125, an electron blocking layer (EBL) 130, an emission layer (EML) 135, a hole blocking layer (HBL) 140, an electron transport layer (ETL) 145, an electron injection layer (EIL) 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by depositing the layers in sequence. The properties and functions of these various layers and exemplary materials are described in more detail in columns 6-10 of US 7,279,704, which is incorporated by reference.

[0391] Additional instances of each of these layers can be obtained. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of the light-emitting and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which disclosure is incorporated herein by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin layer of metal (such as Mg:Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of the blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entireties. Examples of the injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0392] Figure 2 Displays an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. The device 200 can be fabricated by depositing the layers in sequence. Since the most common OLED configuration has a cathode disposed above the anode, and the device 200 has a cathode 215 disposed below the anode 230, the device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to the device 100 can be used in the corresponding layers of the device 200. Figure 2 Provides an example of how some layers can be omitted from the structure of the device 100.

[0393] Figure 1 and 2The simple layered structure described herein is provided by way of non-limiting examples, and it should be understood that embodiments of the present disclosure can be used in combination with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the various layers described in different ways, or the layers can be completely omitted based on design, performance, and cost factors. Other layers not specifically described can also be included. Materials other than those specifically described can be used. Although many of the examples provided herein describe the various layers as including a single material, it should be understood that combinations of materials can be used, such as mixtures of hosts and dopants, or more generally, mixtures. Additionally, the layers can have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, the hole transport layer 225 transports holes and injects holes into the emission layer 220, and can be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer can comprise a single layer, or can further comprise multiple layers of different organic materials such as, for example, as described with respect to Figure 1 and 2 the different organic materials.

[0394] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) comprising polymeric materials, as disclosed, for example, in U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. By way of another example, an OLED having a single organic layer can be used. OLEDs can be stacked, for example, as described in U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. The OLED structure can deviate from Figure 1 and 2 the simple layered structure described therein. For example, the substrate can include angled reflective surfaces to improve out-coupling, such as the mesa structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the dimpled structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0395] Unless otherwise specified, any one 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 nitrogen or an inert atmosphere. For other layers, preferred methods include thermal evaporation, sputtering, chemical vapor deposition, atomic layer deposition, and electron beam deposition. Preferred patterning methods include deposition through a mask, photolithography, and cold welding (as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety) and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The materials to be deposited may be modified to be suitable for a particular deposition method. For example, substituents such as alkyl and aryl, 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 a range of 3 to 20 carbons is preferred. Materials having an asymmetric structure may have better solution processability than materials having a symmetric structure because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0396] Devices fabricated in accordance with embodiments of the present disclosure may further optionally include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage by harmful substances in an environment exposed to, including moisture, vapor, and / or gas, etc. The barrier layer may be deposited over the substrate, over the electrodes, under the substrate, under the electrodes, beside the substrate, electrodes, or over any other part of the device (including the edges). The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic compounds or organic compounds or both. Preferred barrier layers include multiple alternative layers of the following materials: polymeric materials and non-polymeric materials; organic materials and inorganic materials; or mixtures of polymeric materials and non-polymeric materials, an example of which is described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entireties.

[0397] Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units), which can in turn be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels) that can be utilized by end-user product manufacturers, and the like. The electronic component module can optionally include driving electronics and / or a power source. Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of consumer products that have one or more electronic component modules (or units) incorporated therein. Disclosed is a consumer product that includes an OLED which includes a compound of the present disclosure in an organic layer of the OLED. The consumer product should include any type of product that includes one or more of one or more light sources and / or a certain type of visual display. Some examples of the consumer product include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external illumination and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular telephones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays (displays having a diagonal of less than 2 inches), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls that include multiple displays tiled together, theater or stadium screens, light therapy devices, and signs. A variety of control mechanisms can be used to control the devices fabricated in accordance with the present disclosure, including passive matrix and active matrix. It is intended that many of the devices be used in a temperature range that is comfortable for humans, such as from 18 °C to 30 °C, and more preferably at room temperature (20 - 25 °C), but they can be used outside of this temperature range (e.g., from -40 °C to +80 °C).

[0398] More details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0399] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can employ the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0400] In some embodiments, the OLED has one or more characteristics selected from the group consisting of flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further includes a layer comprising carbon nanotubes. In some embodiments, the OLED further includes one or more quantum dots. Such quantum dots may be in the emission layer or in other functional layers, such as a down-conversion layer.

[0401] In some embodiments, the OLED includes an RGB pixel arrangement or a white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel with a diagonal less than 10 inches or an area less than 50 square inches. In some embodiments, the OLED is a display panel with a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0402] Other materials used in D.OLED

[0403] The materials described herein are various examples of specific layers that can be used in an OLED. It can also be used in combination with a wide variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used by themselves in the emissive dopants in the EML or in combination with a wide variety of other emitters, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds and devices disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0404] a) Conductive dopants:

[0405] 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. Conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant, and an n-type conductive dopant is used in the electron transport layer. In some embodiments, the conductive dopant includes at least one chemical moiety selected from the group consisting of cyano, fluorinated aryl or heteroaryl, fluorinated alkyl or cycloalkyl, alkylene, heteroaryl, amide, benzodithiophene, and highly conjugated heteroaryl extended by an acyclic double bond.

[0406] b) HIL / HTL:

[0407] The hole injection / transport materials used in the present disclosure are not particularly limited, and any compound can be used as long as the compound is commonly used as a hole injection / transport material. Examples of the materials include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorohydrocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x ; p-type semi-conductive organic compounds such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile; metal complexes; and crosslinkable compounds.

[0408] Examples of the aromatic amine derivatives for HIL or HTL include (but are not limited to) the following general structures:

[0409]

[0410] Ar 1 to Ar 9 each of which is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, fluorene, phenanthrene, fluorene, pyrene, perylene and azulene; the group consisting of aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Ar 1 to Ar 9 each of which may be unsubstituted or may be substituted with a general substituent as described above, and any two substituents may be joined or fused into a ring.

[0411] In some embodiments, each Ar 1 to Ar 9 independently comprises a moiety selected from the group consisting of:

[0412]

[0413] where k is an integer from 1 to 20; X 101 to X 108 is C or N; Z 101 is C, N, O, or S.

[0414] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0415]

[0416] where Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, and the coordinating atoms of Y 101 and Y 102 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be connected to the metal; and k' + k" is the maximum number of ligands that can be connected to the metal.

[0417] In some embodiments, (Y 101 -Y 102 ) is a 2-phenylpyridine or 2-phenylimidazole derivative. In some embodiments, (Y 101 -Y 102 ) is a carbene ligand. In some embodiments, Met is selected from Ir, Pt, Pd, Os, Cu, and Zn. In some embodiments, the metal complex has a minimum oxidation potential in solution of less than about 0.6 V compared to the Fc + / Fc couple.

[0418] In some embodiments, the HIL / HTL material is selected from the group consisting of: phthalocyanine and porphyrin compounds, starburst triarylamine, CF x fluorocarbon polymers, conductive polymers (e.g., PEDOT:PSS, polyaniline, polythiophene), phosphonic acids and silane SAMs, triarylamines or polythiophene polymers containing conductive dopants, organic compounds containing conductive inorganic compounds (such as molybdenum oxide and tungsten oxide), n-type semiconducting organic complexes, organometallic metal complexes, crosslinkable compounds, polythiophene-based polymers and copolymers, triarylamines, triarylamines containing a spirofluorene core, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indolocarbazole, isoindole compounds, and metal carbene complexes.

[0419] c) EBL:

[0420] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Additionally, a blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or higher triplet energy compared to one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO level of the compound used in the EBL is shallower than the HOMO level of one or more of the hosts in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional group as one of the hosts described below.

[0421] d) Host:

[0422] 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.

[0423] Examples of metal complexes used as hosts preferably have the following general formula:

[0424]

[0425] where Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, and the coordinating atoms of Y 103 and Y 104 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be connected to the metal; and k'+k" is the maximum number of ligands that can be connected to the metal.

[0426] In some embodiments, the metal complex is:

[0427]

[0428] where (O-N) is a bidentate ligand having a metal coordinated to O and N atoms.

[0429] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0430] In some embodiments, the host compound contains at least one selected from the following groups: the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-carbazole, aza-indolocarbazole, aza-triphenylene, aza-tetraphenylene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-borata-naphtho[3,2,1-de]anthracene; and the group consisting of 2 to 10 cyclic structural units, which are the same type or different types of groups selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each option within each group may be unsubstituted or may be substituted with a general substituent as described herein or may be further fused.

[0431] In some embodiments, the host compound contains at least one selected from the moieties consisting of:

[0432]

[0433] where k is an integer from 0 to 20 or from 1 to 20. X 101 to X 108 are independently selected from C or N. Z 101 and Z 102 are independently selected from C, N, O, or S.

[0434] In some embodiments, the host material is selected from the group consisting of arylcarbazole, metal 8-hydroxyquinolinates (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic condensed rings, zinc complexes, based on Compounds, aryltriphenylene compounds, polycondensed heteroaryl compounds, donor-acceptor type molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., pvk), spirofluorene compounds, spirofluorene-carbazole compounds, indolocarbazole, 5-membered ring electron-deficient heterocycles (e.g., triazole, oxadiazole), tetracene complexes, metal phenoxypyridine compounds, metal coordination complexes (e.g., Zn, Al containing N^N ligands), dibenzothiophene / dibenzofuran-carbazole compounds, silicon / germanium aryl compounds, aryl benzoyl esters, carbazole linked by non-conjugated groups, azacarbazole / dibenzofuran / dibenzothiophene compounds, and high triplet metal organometallic complexes (e.g., metal-carbene complexes).

[0435] e) Emitter materials in the EML:

[0436] One or more emitter materials can be used in combination with the compounds or devices of the present disclosure. The emitter materials can be emissive or non-emissive in the current devices as described herein. Examples of emitter materials are not particularly limited, and any compound can be used as long as the compound can produce emission in a conventional OLED device. Examples of suitable emitter materials include, but are not limited to, compounds capable of producing emission via phosphorescence, non-delayed fluorescence, delayed fluorescence (especially thermally activated delayed fluorescence, i.e., TADF (also known as E-type delayed fluorescence)), triplet-triplet annihilation, or a combination of these methods.

[0437] In some embodiments, the emitter material has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0438] wherein L 1 , L 2 and L 3 can be the same or different;

[0439] wherein x is 1, 2 or 3;

[0440] wherein y is 0, 1 or 2;

[0441] wherein z is 0, 1 or 2;

[0442] wherein x + y + z is the oxidation state of the metal M;

[0443] wherein L 1 is selected from the group consisting of the structures of the following ligand list:

[0444]

[0445]

[0446]

[0447] wherein each L 2 and L 3 are independently selected from the group consisting of: and the structure of the ligand list; wherein:

[0448] M is selected from the group consisting of: Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag, and Cu;

[0449] T is selected from the group consisting of: B, Al, Ga, and In;

[0450] K 1 ' is a direct bond or is selected from the group consisting of NR e , PR e , O, S, and Se;

[0451] each Y 1 to Y 15 are independently selected from the group consisting of carbon and nitrogen;

[0452] Y' is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO2, CR e R f , SiR e R f , and GeR e R f ;

[0453] each R a , R b , R c , and R d can independently represent mono-substitution to the maximum possible number of substitutions, or no substitution;

[0454] each R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f are independently hydrogen or a substituent selected from the group of general substituents as defined herein; and

[0455] Any two of these substituents may be fused or joined to form a ring or form a polydentate ligand.

[0456] In some embodiments, the emitter material is selected from the group consisting of dopants in dopant group 1:

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463] wherein

[0464] X 96 to X 99 each is independently C or N;

[0465] each Y 100 is independently selected from the group consisting of NR″, O, S, and Se;

[0466] R 10a 、R 20a 、R 30a 、R 40a and R 50a each independently represents mono-substituted, up to maximally substituted, or unsubstituted;

[0467] 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 is independently hydrogen or a substituent selected from the group of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0468] In some embodiments, the emitter material is selected from the group consisting of dopants in dopant group 2:

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477] wherein:

[0478] each Y 100 is independently selected from the group consisting of NR″, O, S, and Se;

[0479] 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;

[0480] X 100 and X 200 are each independently selected, at each occurrence, from the group consisting of O, S, Se, NR″, and CR″R″′;

[0481] each R A ″, R B ″, R C ″, R D ″, R E ″ and R F ″ independently represents mono-substituted, up to maximum substitution, or unsubstituted;

[0482] 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 ″, RM ” and R N ” is independently hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0483] In some embodiments of the above dopant groups 1 and 2, each unsubstituted aromatic carbon atom may be replaced by N to form a heterocycle. In some embodiments, the maximum number of N atoms in a ring is 1 or 2. In some embodiments of the above dopant group 2, the Pt atom in each formula may be replaced by a Pd atom.

[0484] In some embodiments of the OLED, the delayed fluorescence material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescence material is a metal complex. In some embodiments, the delayed fluorescence material is a non-metal complex. In some embodiments, the delayed fluorescence material is a Zn, Cu, Ag or Au complex.

[0485] In some embodiments of the OLED, the delayed fluorescence material has the formula M(L 5 )(L 6 ), where M is Cu, Ag or Au, L 5 and L 6 are different, and L 5 and L 6 are independently selected from the group consisting of:

[0486]

[0487]

[0488]

[0489] where A 1 -A 9 are each independently selected from C or N;

[0490] Each R P , R Q and R U independently represents mono-substituted, up to maximum substitution or unsubstituted;

[0491] where each R P , R P , R U , R SA , R SB , R RA , R RB , R RC , R RD , R RE and R RFindependently is hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents may be joined or fused to form a ring.

[0492] In some embodiments of the OLED, the delayed fluorescence material comprises at least one selected from the group consisting of donor moieties:

[0493]

[0494]

[0495] wherein Y T 、Y U 、Y V and Y W are each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C═O, S═O, and SO2.

[0496] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures up to a total of at most three carbon ring atoms together with its substituents may be replaced by N.

[0497] In some embodiments, the delayed fluorescence material comprises at least one selected from the group consisting of acceptor moieties: 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 may be directly connected, connected via a conjugated linking group or a non-conjugated linking group (such as sp 3 carbon or silicon atoms).

[0498] In some embodiments, the fluorescent material comprises at least one selected from the group consisting of chemical moieties:

[0499]

[0500]

[0501]

[0502] wherein Y F 、Y G 、Y H and Y I are each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C═O, S═O, and SO2;

[0503] wherein XF and X G are each independently selected from the group consisting of C and N.

[0504] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures up to a total of at most three carbon ring atoms together with its substituents can be replaced by N.

[0505] f) HBL:

[0506] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Additionally, a blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and / or a higher triplet energy compared to one or more of the emitters closest to the HBL interface.

[0507] In some embodiments, the compound used in the HBL contains the same molecule or the same functional group as used in the host described above.

[0508] In some embodiments, the compound used in the HBL contains at least one of the following moieties selected from the group consisting of:

[0509]

[0510]

[0511] where k is an integer from 1 to 20; L 101 is another ligand and k' is an integer from 1 to 3.

[0512] g) ETL:

[0513] An electron transport layer (ETL) can include a material capable of transporting electrons. The electron transport layer can be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited and any metal complex or organic compound can be used as long as it is commonly used to transport electrons.

[0514] In some embodiments, the compound used in the ETL contains at least one of the following moieties in the molecule:

[0515]

[0516] and fullerenes; where k is an integer from 1 to 20, X 101 to X 108 is selected from C or N; Z101 Selected from the group consisting of C, N, O, and S.

[0517] In some embodiments, the metal complex used in the ETL has, but is not limited to, the following general formula:

[0518]

[0519] where (O-N) or (N-N) is a bidentate ligand having a metal coordinated to the atoms O, N, or N, N; L 101 is another ligand; and k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.

[0520] 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 ring electron-deficient heterocycles (e.g., triazole, oxadiazole, imidazole, benzimidazole), silole compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0521] h) Charge Generation Layer (CGL)

[0522] In a tandem or stacked OLED, the CGL plays a fundamental role in performance and consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and the electrodes. The electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductive dopants used in the transport layer.

[0523] In any of the compounds disclosed herein, the hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. As used herein, the deuteration percentage has its ordinary meaning and includes the percentage of all possible hydrogen and deuterium atoms replaced by deuterium atoms. In some embodiments, the deuterium atoms are attached to an aromatic ring. In some embodiments, the deuterium atoms are attached to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atoms are attached to a heteroatom, such as an Si or Ge atom.

[0524] It should be understood that the various embodiments described herein are for illustrative purposes only and are not intended to limit the scope of the present invention. For example, many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. The present invention as claimed may thus include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

[0525] Experimental data

[0526] Synthesis of the emitter-1 of the present invention

[0527] (Synthesis of (3,5-dibromophenyl)triphenylsilane: A 50 mL flask was dried with a hot air gun. 1,3,5-Tribromobenzene (1.500 g, 1 equivalent, 4.765 mmol) dissolved in diethyl ether (25.00 mL) was added. At -78 °C, n-butyllithium (305.2 mg, 2.978 mL, 1.600 molar concentration, 1 equivalent, 4.765 mmol) was added dropwise over 10 minutes. The mixture was maintained at -78 °C for 2 hours. Chlorotriphenylsilane (1.405 g, 1 equivalent, 4.765 mmol) in 10 mL of diethyl ether was added dropwise, and the reaction mixture was slowly warmed to room temperature and stirred for 18 hours. The crude product (700 mg, 30% yield) was purified by column chromatography.

[0528] (Synthesis of 2-(3-bromo-5-(triphenylsilyl)phenyl)pyridine: (3,5-Dibromophenyl)triphenylsilane (0.8600 g, 1 equivalent, 1.740 mmol) and bis(triphenylphosphine)palladium(II) dichloride (122.1 mg, 0.1 equivalent, 174.0 μmol) were charged into an RBF equipped with a condenser and dissolved in THF (17.40 mL). The solution was degassed by bubbling nitrogen through it for 10 minutes, and then pyridin-2-ylzinc(II) bromide (427.5 mg, 3.828 mL, 0.500 molar concentration, 1.1 equivalents, 1.914 mmol) was added via syringe. The reaction was heated to 70 °C and stirred for 2 hours, and the crude mixture (382 mg, 45% yield) was purified by column chromatography.

[0529] Synthesis of 2,4-Di-tert-butyl-6-(4-(tert-butyl)-6-chloropyridin-2-yl)phenol: Cesium carbonate (4.412 g, 1 equiv, 13.54 mmol), tetrakis(triphenylphosphine)palladium(0) (782.5 mg, 0.05 equiv, 677.1 μmol), 4-(tert-butyl)-2,6-dichloropyridine (5.528 g, 2 equiv, 27.08 mmol), and 2,4-di-tert-butyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (4.500 g, 1 equiv, 13.54 mmol) were dissolved in a mixture of 1,4-dioxane (100.0 mL) and water (20.00 mL). The mixture was bubbled with N2 for 20 minutes, equipped with an air condenser at the top, and stirred at 90 °C. The product was purified by column chromatography (4.5 g, 89% yield).

[0530] Synthesis of 2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(triphenylsilyl)phenyl)pyridine: 2-(3-Bromo-5-(triphenylsilyl)phenyl)pyridine (0.5744 g, 1 equiv, 1.166 mmol), bis(pinacolato)diboron (444.3 mg, 1.5 equiv, 1.749 mmol), and potassium acetate (263.3 mg, 2.3 equiv, 2.683 mmol) were added to an RBF equipped with a condenser, and the atmosphere was replaced with nitrogen. 1,4-Dioxane (23.33 mL) was added and the solution was degassed using an in-house vacuum. Subsequently, Pd(dppf)Cl2·DCM (190.5 mg, 0.20 equiv, 233.3 μmol) was added and further degassed. The reaction was heated to 95 °C and stirred for 3 hours, and purified by column chromatography (288 mg, 46% yield).

[0531] Synthesis of 2,4-Di-tert-butyl-6-(4-(tert-butyl)-6-(3-(pyridin-2-yl)-5-(triphenylsilyl)phenyl)pyridin-2-yl)phenol: Add 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(triphenylsilyl)phenyl)pyridine (2.5429 g, 1 equivalent, 4.7129 mmol), 2,4-di-tert-butyl-6-(4-(tert-butyl)-6-chloropyridin-2-yl)phenol (1.7625 g, 1 equivalent, 4.7129 mmol), and potassium carbonate (1.9540 g, 3 equivalents, 14.139 mmol) into a vial. Then add dioxane and water, and degas the suspension by bubbling nitrogen for 2 minutes. Then add SPhos Pd G2 (339.63 mg, 0.10 equivalent, 471.29 μmol), degas the suspension again, then seal the vial and transfer it to a preheated sand bath, and stir at 100 °C for 18 hours. Purify the product by column chromatography (1.59 g, 45% yield).

[0532] Synthesis of Emitter-1: Add 2,4-di-tert-butyl-6-(4-(tert-butyl)-6-(3-(pyridin-2-yl)-5-(triphenylsilyl)phenyl)pyridin-2-yl)phenol (0.2114 g, 1 equivalent, 281.5 μmol) and a Pt precursor (1.2 equivalents) into a Schlenk tube under nitrogen. Then add an organic solvent (7.00 mL), and stir the mixture under house vacuum to degas for 10 minutes. Replace the atmosphere with nitrogen, then add an organic base (5 equivalents) via syringe under a nitrogen stream, and then degas again. Reflux the Schlenk tube for 18 hours. Chromatograph the crude mixture to obtain the Emitter-1 of the present invention (113 mg, 43% yield).

[0533]

[0534] The synthesis of Emitter-2 can be achieved using the synthesis method of Emitter-1 but replacing chlorotriphenylsilane with chlorotriphenylgermane.

[0535]

[0536] The synthesis of Emitter-3 can be achieved using the synthesis method we previously reported in US20240251655A1 but replacing 1,3-dibromo-5-(tert-butyl)benzene with (3,5-dibromophenyl)triphenylsilane.

[0537]

[0538] The synthesis of Emitter-4 can be achieved using the synthetic method we previously reported in US20240251655A1, but with (3,5-dibromophenyl)di-mesitylborane instead of 1,3-dibromo-5-(tert-butyl)benzene. (3,5-Dibromophenyl)di-mesitylborane can be prepared according to the literature procedure in the Journal of Organic Chemistry (J. Org. Chem.) 2015, 80, 4097.

[0539]

[0540] The synthesis of Emitter-5 can be achieved using the synthetic method we previously reported in US20240251655A1, but with 2,4-dibromodibenzo[b,d]thiophene instead of 1,3-dibromo-5-(tert-butyl)benzene.

[0541]

[0542] The synthesis of Emitter-6 can be achieved using the synthetic method of Emitter-1, but with 2,4-dibromodibenzo[b,d]thiophene instead of (3,5-dibromophenyl)triphenylsilane.

[0543] Table 1. Photophysical properties

[0544]

[0545] Table 1 summarizes the basic photophysical properties of Emitter-1 and the comparative examples. By adding the decoration of the present invention to the core Pt skeleton, the emission wavelength is more suitable for green applications. In addition, the features of the present invention greatly improve the PLQY, which is one of the basic requirements for making the emitter useful in OLED applications.

[0546] Emission spectra were collected using a Horiba Fluorolog-3 spectrofluorometer equipped with a Synapse Plus CCD detector. All samples were excited at 340 nm. The 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 solution of 1% emitter and PMMA in toluene was prepared, filtered, and cast dropwise onto a quartz substrate. The T1 energy was obtained from the emission spectrum of the frozen sample in 2-MeTHF at 77 K.

Claims

1. A compound comprising a structure of formula I: wherein moieties A, B, C and D are each independently a monocyclic or polycyclic fused ring system, wherein each ring in said monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; wherein M is selected from Pt and Pd; Where X 1 -X 4 each independently is C or N; Where Z 1 -Z 4 each independently is C or N; Wherein L is a direct bond, or an organic linking group having one or two linking atoms; Where K 1 and K 2 Each is independently a direct bond or selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) in represents a single bond or a double bond; Where K 1 and K 2 At least one of each independently selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) Where R A , R B , R C and R D Each independently represents mono-substitution to the maximum permissible substitution, or no substitution; Each R α , R β , R A , R B , R C and R D are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, borane, selenanyl, and combinations thereof; wherein any two substituents may be fused or joined to form a ring; Where R A , R B , R C and R D At least one of the atoms comprises an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P; wherein any two substituents may be fused or joined to form a ring; and Wherein the compound is not:

2. The compound according to claim 1, wherein R α , R β , R A , R B , R C and R D are each independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof; and / or wherein if K 1 and K 2 is a direct bond and moiety A is a 6-membered ring, then L is a direct bond; and / or wherein if moiety A is a 5-membered ring, then moiety C is a 5-membered ring.

3. The compound according to claim 1, wherein K 1 and K 2 one of which is a direct key; and / or wherein K 1 and K 2 One of them is O, and K 1 and K 2 The other of which is a direct bond; and / or wherein Z 1 -Z 4 At least one of which is N; and / or wherein X 1 -X 4 All are C.

4. The compound according to claim 1, wherein L is selected from the group consisting of: a direct bond, O, S, Se, NR, BR, BRR', PR, CR, C=O, C=NR, C=CRR', C=S, CRR', SO, SO2, P(O)R, SiRR', GeRR', alkylene, cycloalkylene, arylene, heteroarylene, and combinations thereof; and / or wherein L is a direct bond; and / or wherein at least two R A to form a 5-membered ring fused to moiety A; and / or At least two of the R A Joined to form a 5-membered aromatic heterocyclic ring fused to part A.

5. The compound according to claim 1, wherein at least two R B to form a 5-membered aromatic heterocyclic ring fused to moiety B; and / or wherein the compound comprises at least two atoms selected from the group consisting of deuterium, B, Si, Ge, S, Se and P; and / or wherein R A , R B , R C and R D At least one of the comprises at least one deuterium atom.

6. The compound according to claim 1, wherein R A , R B , R C and R D At least one of them contains at least one B atom; and / or wherein R A , R B , R C and R D At least one of them contains at least one Si atom.

7. The compound of claim 1, wherein at least one atom selected from the group consisting of B, Si, Ge, S, Se and P is directly bonded to one of the moieties A, B, C or D.

8. The compound according to claim 1, wherein when K 1 and K 2 When one of is a direct bond and the moiety A is a 6-membered ring, then L is a direct bond.

9. The compound according to claim 1, wherein the compound is selected from the group consisting of A' The group consisting of compounds of )(Ly): Where L A' Selected from the group consisting of the structures shown below in Listing 1 and Listing 2: Listing 1: Listing 2: Where L y Select from the group consisting of the structures shown below in Listing 3 and Listing 4: Listing 3: Listing 4: Among them, when L A' When from list 1, Ly is from list 3 and list 4; Among them, when L A' When from list 2, Ly is from list 3; Where R A , R B , R C , R CC , R D , R E , R G At least one of R, R', R" and R'" is selected from R203-R445 as defined in List 11 as defined herein; Each R A , R B , R C , R CC , R D , R E , R G , R, R', R" and R'" are independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, borane, selenanyl and combinations thereof.

10. The compound according to claim 1, wherein the compound is selected from the group consisting of A' The group consisting of compounds of )(Ly): Where L A' Choose from L A' W 1 -(Ri)(Rj)(Rk)(Rl), where W 1 is an integer from 1 to 40, wherein i, j, k, l are each independently an integer from 1 to 445, each Ri, Rj, Rk and Rl are independently selected from R1-R445, wherein at least one of Ri, Rj, Rk, Rl is selected from R203-R445: wherein L A' 1-(R1)(R1)(R1)(R1) to L A' Each of 4-(R445)(R445)(R445)(R445) is shown in Listing 7, and L A' 5-(R1)(R1)(R1)(R1) to L A' 40-(R445)(R445)(R445)(R445) is shown in Listing 8, both Listing 7 and Listing 8 are defined in this article; Where L y Choose from L y Z 1 -(Rs)(Rt)(Ru)(Rv), where Z 1 is an integer from 1 to 22, wherein s, t, u and v are each independently an integer from 1 to 445, and each of Rs, Rt, Ru and Rv is independently selected from R1 to R445, wherein at least one of Rs, Rt, Ru and Rv is selected from R203-R445; L y 1-(R1)(R1)(R1)(R1) to L y 3-(R445)(R445)(R445)(R445) is defined in Listing 9, and L y 4-(R1)(R1)(R1)(R1) to L y 22-(R445)(R445)(R445)(R445) is defined in Listing 10, and both Listing 9 and Listing 10 are defined in this document; Among them, when L A' When from list 7, Ly is from list 9 and list 10; Among them, when L A' When from list 8, Ly is from list 9; Wherein R1 to R445 have the following structure defined in Listing 11 as defined herein.

11. The compound of claim 1, wherein the compound is selected from the group consisting of the structures in List 12 as defined herein.

12. An organic light emitting device (OLED), comprising: anode; cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a compound having a structure comprising Formula I: wherein moieties A, B, C and D are each independently a monocyclic or polycyclic fused ring system, wherein each ring in said monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; wherein M is selected from Pt and Pd; Where X 1 -X 4 each independently is C or N; Where Z 1 -Z 4 each independently is C or N; Wherein L is a direct bond, or an organic linking group having one or two linking atoms; Where K 1 and K 2 Each is independently a direct bond or selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) in represents a single bond or a double bond; Where K 1 and K 2 At least one of each independently selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) Where R A , R B , R C and R D Each independently represents mono-substitution to the maximum permissible substitution, or no substitution; Each R α , R β , R A , R B , R C and R D are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, borane, selenanyl, and combinations thereof; wherein any two substituents may be fused or joined to form a ring; Where R A , R B , R C and R D At least one of the atoms comprises an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P; wherein any two substituents may be fused or joined to form a ring; and Wherein the compound is not:

13. The OLED of claim 12, wherein the organic layer further comprises a host, wherein the host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-borazinonaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-borazinonaphtho[3,2,1-de]anthracene).

14. The OLED of claim 13, wherein the host is selected from the group consisting of the structures in Listing 13 as defined herein; in: X 1 To X 24 Each of is independently C or N; L' is a direct bond or an organic linking group; Each Y A independently selected from the group consisting of: absence of a bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR'; 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; R, R', R A '、R B '、R C '、R D '、R E '、R F ' and R G ' 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, selenanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, borane, and combinations thereof; R A '、R B '、R C '、R D '、R E '、R F ' and R G ' are optionally joined or fused to form a ring.

15. A consumer product comprising an organic light emitting device (OLED), the OLED comprising: anode; cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a compound having a structure comprising Formula I: wherein moieties A, B, C and D are each independently a monocyclic or polycyclic fused ring system, wherein each ring in said monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring; wherein M is selected from Pt and Pd; Where X 1 -X 4 each independently is C or N; Where Z 1 -Z 4 each independently is C or N; Wherein L is a direct bond, or an organic linking group having one or two linking atoms; Where K 1 and K 2 Each is independently a direct bond or selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) in represents a single bond or a double bond; Where K 1 and K 2 At least one of each independently selected from O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ) Where R A , R B , R C and R D Each independently represents mono-substitution to the maximum permissible substitution, or no substitution; Each R α , R β , R A , R B , R C and R D are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, borane, selenanyl, and combinations thereof; wherein any two substituents may be fused or joined to form a ring; Where R A , R B , R C and R D At least one of the atoms comprises an atom selected from the group consisting of deuterium, B, Si, Ge, S, Se, and P; wherein any two substituents may be fused or joined to form a ring; and Wherein the compound is not:

Images