Organic electroluminescent materials and devices

Abstract

Disclosed are compounds having the structure of Formula I. At least one RA or RB comprises an olefin moiety, wherein if the olefin forms part of a ring, the ring is not aromatic, and / or at least one of the structures A or B comprises a non-aromatic ring having at least one olefin moiety. If M is Ir, at least one of the following holds: K is not a direct bond; structures A and B are polycyclic fused ring systems; Z4 is C, and structure B is a polycyclic fused ring system having exactly two rings or at least four rings; or the compound has a ligand LB comprising a structure G, wherein structure G is coordinated to M and is a polycyclic fused ring system having at least four rings, each ring of the polycyclic fused ring system being a 5- to 10-membered carbocyclic or heterocyclic ring. Also provided are compositions, OLEDs, and consumer articles containing the compounds. Formula I

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 790,768, filed April 18, 2025, and U.S. Provisional Application No. 63 / 884,401, filed September 19, 2025, pursuant to 35 U.S. SC §119(e), the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly popular. Many of the materials used to manufacture such devices are relatively inexpensive, thus organic optoelectronic devices have the potential to offer a cost advantage over inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, make them more suitable for specific 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 offer performance advantages over conventional materials.

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

[0006] One application of emitting molecules is in full-color displays. Industry standards for such displays require pixels suited to emitting specific colors (called "saturated" colors). Specifically, these standards require pixels saturated with red, green, and blue light. 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 emission. The same technology can be used for OLEDs. White OLEDs can be single-emitting-layer (EML) devices or stacked structures. Color can be measured using CIE coordinates, well-known in the art. Invention Overview

[0007] In one aspect, this disclosure provides a first ligand L A The compound, the first ligand L A Structure of Formula I:

[0008] Formula I,

[0009] in:

[0010] Structural part A and structural part B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring;

[0011] Z 1 -Z 4 Each can be either C or N independently;

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

[0013] R A and R B Each can be used independently to represent monosubstitution up to the maximum permissible substitution, or no substitution.

[0014] R α R β R A and R B Each of the following is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof;

[0015] At least one of the following conditions must be true:

[0016] i) at least one R A Or R B It includes an olefin structural moiety, wherein if the olefin structural moiety forms part of a ring, the ring is not aromatic; or

[0017] ii) At least one of structural moiety A or structural moiety B contains a non-aromatic ring having at least one olefinic structural moiety;

[0018] L A Fitted in metal M;

[0019] M is selected from the following groups: Os, Ir, Pd, Pt, Rh, Re, Ru, Cu, Ag, and Au;

[0020] M can ligand other ligands;

[0021] L A It can be linked with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands;

[0022] Any two substituents can be linked or fused to form a ring.

[0023] In another aspect, this disclosure provides a first ligand L A The compound, or its neutral molecular form, or its monovalent or polyvalent form, or its monomeric or polymeric form, or its macromolecular or supramolecular form, wherein the compound having a first ligand L A The compounds are as described in this article.

[0024] In another aspect, this disclosure provides the first ligand L described herein. A Compositions of compounds.

[0025] In another aspect, this disclosure provides an OLED having an organic layer comprising the first ligand L described herein. A Compounds.

[0026] In another aspect, this disclosure provides consumer products comprising an OLED having an organic layer, said organic layer comprising the first ligand L described herein. A Compounds. Brief description of the attached figures

[0027] Figure 1 An organic light-emitting device is shown.

[0028] Figure 2 An inverted organic light-emitting device without a separate electron transport layer is shown. Detailed description

[0029] A. Terminology

[0030] Unless otherwise specified, the following terms as used herein are defined as follows:

[0031] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "placed" "above" the second layer, the first layer is placed at a greater distance from the substrate. Unless otherwise specified, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "placed" "above" the anode.

[0032] As used herein, "solution-processable" means capable of dissolving, dispersing, or transporting in and / or depositing from a liquid medium in the form of a solution or suspension.

[0033] As used herein and as commonly understood by those skilled in the art, if a first energy level is closer to the vacuum level, then the first “highest occupied molecular orbital” (HOMO) or “lowest unoccupied molecular orbital” (LUMO) level is “greater” or “higher” than the second HOMO or LUMO level. Because the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with the vacuum level at the top, the LUMO level of a material is higher than the HOMO level of the same material. A “higher” HOMO or LUMO level is closer to the top of such a diagram than a “lower” HOMO or LUMO level.

[0034] As used herein and as is generally understood by those skilled in the art, if the first work function has a higher absolute value, then the first work function is “greater” or “higher” than the second work function. This is because the work function is typically measured as a negative number relative to the vacuum level, meaning that a “higher” work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a “higher” work function is shown as being further away from the vacuum level in the downward direction. Therefore, the definitions of HOMO and LUMO levels follow different rules than those for the work function.

[0035] This document may describe layers, materials, regions, and devices by referring to the color of light emitted by them. Generally, as used herein, an emitting region described as producing a particular color of light may include one or more emitting layers arranged in a stacked manner on top of each other.

[0036] As used herein, “NIR,” “red,” “green,” “blue,” and “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, and 540–600 nm, respectively, or layers, materials, regions, or devices that have a peak in their emission spectrum within the corresponding wavelength regions. In some arrangements, individual regions, layers, materials, or devices may provide separate “deep blue” and “light blue” emissions. As used herein, a “deep blue” emission component refers to an emission whose peak emission wavelength is at least approximately 4 nm smaller than the peak emission wavelength of the “light blue” emission component. Typically, the peak emission wavelength of the “light blue” emission component is in the range of approximately 465–500 nm, and the peak emission wavelength of the “deep blue” emission component is in the range of approximately 400–470 nm, but these ranges may vary for some configurations.

[0037] In some arrangements, a color-changing layer is provided that converts, modifies, or alters the color of light emitted by another layer to emit light with a different wavelength. Such a color-changing layer can be tuned to an amount defined by a wavelength shift of the light emitted by the other layer, 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 unwanted wavelengths of light, and color-changing layers that convert higher-energy photons into lower-energy photons. For example, a "red" color filter may be present to filter input light to remove light with wavelengths outside the approximately 580-700 nm range. An element of a particular "color" refers to an element that, when activated or used, produces or otherwise emits light having the specific color described above. 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 described above when activated within the device.

[0038] In this context, emitting materials, layers, and regions are distinguishable from each other and from other structures based on the light initially generated by the material, layer, or region (not the light ultimately emitted by the same or different structures). Initial light generation is typically a result of energy level changes that lead to photon emission. For example, an organic emitting material may initially generate blue light, which can be converted into red or green light by filters, quantum dots, or other structures, causing the entire emitting stack or subpixel to emit red or green light. In this case, the initial emitting material, region, or layer can be referred to as a "blue" element, even if the subpixel is a "red" or "green" element.

[0039] In some cases, describing the color of elements such as emission regions, subpixels, color-changing layers, etc., according to the 1931 CIE coordinates may be preferred. For example, a yellow emitting material may have multiple peak emission wavelengths, one within or near the edge of the previously described "green" region, and one within or near the edge of the previously described "red" region. Therefore, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. A shape in the 1931 CIE color space is constructed by tracing a path 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:

[0040]

[0041] The terms “halogen,” “halogen,” and “halogen group” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0042] The term "acyl" refers to a substituted carbonyl group (-C(O)-R). s ).

[0043] The term "ester" refers to a substituted oxycarbonyl group (-OC(O)-R). s or -C(O)-OR s ) group.

[0044] The term "ether" refers to -OR s Group.

[0045] The terms "thioalkyl" or "thioether" are used interchangeably and refer to -SR s Group.

[0046] The term "selenyl" refers to -SeR s Group.

[0047] The term "sulfinyl" refers to -S(O)-R s Group.

[0048] The term "sulfonyl" refers to -SO2-R s Group.

[0049] The term "phosphinyl" refers to a group containing at least one phosphorus atom bonded to the relevant structure. Common examples of phosphinyl groups include, but are not limited to, -P(R s )2 group or -PO(R s )2 groups, wherein each R s They can be the same or different.

[0050] The term "silyl" refers to a group containing at least one silicon atom bonded to the relevant structure. Common examples of silyl groups include, but are not limited to, -Si(Rs )3 groups, wherein each R s They can be the same or different.

[0051] The term "germanium alkyl" refers to a group containing at least one germanium atom bonded to the relevant structure. Common examples of germanium alkyl groups include, but are not limited to, -Ge(R s )3 groups, wherein each R s They can be the same or different.

[0052] The term "borane" refers to a group containing at least one boron atom bonded to the relevant structure. Common examples of borane groups include, but are not limited to, -B(R s )2 group or its Lewis adduct -B(R s )3 groups, of which R s They can be the same or different.

[0053] In each of the above terminology definitions, R s It can be hydrogen or a substituent selected from the generic substituents defined in this application. Preferred R s Selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. More preferably, R s Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof.

[0054] The term "alkyl" refers to and includes both straight-chain and branched alkyl groups having alkyl carbon atoms bonded to the relevant structure. Preferred alkyl groups are those containing one to fifteen carbon atoms, preferably one to nine carbon atoms, and include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,3-dimethylpropyl, 1,1-dimethylpropyl, 2-ethylpropyl, 1,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3-ethylpentyl, 2,2,3-trimethylbutyl, etc. In addition, alkyl groups can be further substituted.

[0055] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spirocyclic alkyl groups having cycloalkyl carbon atoms bonded to the relevant structure. Preferred cycloalkyl groups are those containing 3 to 12 cyclic carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Furthermore, the cycloalkyl group may be further substituted.

[0056] The terms "heteroalkyl" or "heterocyclic alkyl" refer to an alkyl or cycloalkyl group in which at least one carbon atom is replaced by a heteroatom, respectively. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Furthermore, the heteroalkyl or heterocyclic alkyl group may be further substituted.

[0057] The term "alkenyl" refers to and includes both straight-chain and branched olefin groups. An alkenyl is essentially an alkyl group comprising at least one carbon-carbon double bond in an alkyl chain, wherein one carbon atom from said carbon-carbon double bond is bonded to the associated structure. A cycloalkenyl is essentially a cycloalkyl group comprising at least one carbon-carbon double bond in a cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group in which at least one carbon atom is replaced by a heteroatom. Optionally, said at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Furthermore, said alkenyl, cycloalkenyl, or heteroalkenyl groups may be further substituted.

[0058] The term "alkynyl" refers to and includes both straight-chain and branched alkyne groups. An alkynyl group is essentially an alkyl group comprising at least one carbon-carbon triple bond in an alkyl chain, wherein one carbon atom from said carbon-carbon triple bond is bonded to the relevant structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Furthermore, the alkynyl group may be further substituted.

[0059] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an aryl-substituted alkyl group having an alkyl carbon atom bonded to the relevant structure. Furthermore, the aralkyl group may be further substituted.

[0060] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic 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. The terms "heteroaromatic cyclic group" and "heteroaryl" can be used interchangeably. Preferred non-aromatic heterocyclic groups are those containing 3 to 10 ring atoms, more preferably 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines such as morpholino, piperidinyl, pyrrolyl, etc., and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Furthermore, the heterocyclic group may be further substituted or fused.

[0061] The term "aryl" refers to and includes both monocyclic and polycyclic aromatic hydrocarbon groups. The polycyclic group may have two or more rings, wherein two adjacent rings share two carbon atoms (the rings are "fused"). Preferred aryl groups are those containing six to thirty carbon atoms, more preferably six to twenty-four carbon atoms, or six to eighteen carbon atoms, 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, triphenyl, benzo[9,10]phenanthrene, tetraphenyl, naphthalene, anthracene, phenanthrene, pyrene, β, perylene, and azulene, with phenyl, biphenyl, triphenyl, benzo[9,10]phenanthrene, and naphthyl being preferred. Furthermore, the aryl group may be further substituted or fused, such as, but not limited to, fluorene.

[0062] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom. The heteroatom includes, but is not limited to, O, S, Se, N, P, B, Si, Ge, and Se. In many cases, O, S, N, or B are preferred heteroatoms. A monocyclic heteroaromatic system is preferably a monocycle having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. A polycyclic heterocyclic system may have two or more aromatic rings, wherein two adjacent rings share two atoms (the rings are "fused"), and at least one of the rings is a heteroaryl. A polycyclic heteroaromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryls are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, or three to eighteen carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, Benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenopyridine, selenopyridine, azirborane, cycloborane, 5λ 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium and 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazolium, pyridine, triazine, benzimidazole, 5λ 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo[3,2-a]imidazo[3,2,1-de]anthracene. Additionally, the heteroaryl groups may be further substituted or fused.

[0063] Among the aryl and heteroaryl groups listed above, benzo[9,10]phenanthrene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 5λ 2 ,9λ 2-diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 The groups of -benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-borazonaphtho[3,2,1-de]anthracene, and each of the corresponding aza analogues in said groups are of particular interest.

[0064] In many cases, the general substituents are selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof.

[0065] In some cases, preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioalkyl, and combinations thereof.

[0066] In some cases, more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, germanyl, boronyl, aryl, heteroaryl, nitrile, thioalkyl, and combinations thereof.

[0067] In some cases, even more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitriles and combinations thereof.

[0068] In other cases, the most preferred general substituents are selected from the group consisting of: deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0069] In one or more substituents (e.g., R, R) R R A R A R 1 Where R1, R2, etc., are not specifically defined, each of the one or more substituents shall be understood to independently represent hydrogen or a substituent selected from the general substituents defined herein. Similarly, each of the one or more substituents may optionally be linked or fused with another substituent to form a ring. It should also be understood that any substituent that may be selected from the general substituents defined herein may also be selected from the preferred general substituents defined herein, the more preferred general substituents defined herein, the even more preferred general substituents defined herein, or the most preferred general substituents defined herein.

[0070] The terms "substituted" and "substituted" refer to substituents other than H being bonded to the relevant position, such as carbon or nitrogen. For example, when R... 1 When representing monosubstitution, then an R 1 It must not be H (i.e., substitution). Similarly, when R 1 When representing disubstituted substitution, then the two Rs 1 It must not be H. Similarly, when R... 1 When representing zero or no substitution, all available valences R for ring atoms (such as the carbon atom in benzene and the nitrogen atom in pyrrole) 1 For example, it could be hydrogen, or simply none for ring atoms with fully saturated valences (such as nitrogen 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.

[0071] As used herein, “combinations of them” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl groups can be combined to form haloalkyl substituents; and halogen, alkyl, and aryl groups can be combined to form haloaralkyl groups. In one instance, the term “substitution” includes a combination of two to four listed groups. In another instance, the term “substitution” includes a combination of two to three groups. In yet another instance, the term “substitution” includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations containing up to forty atoms that are not hydrogen or deuterium, or combinations containing up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0072] The term "aza" in the fragments described herein, namely azadibenzofuran, azadibenzothiophene, etc., means that one or more of the CH groups in the corresponding aromatic ring can be replaced by nitrogen atoms. For example, and without limitation, azabenzo[9,10]phenanthrene covers dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza derivatives described above will readily conceive of those skilled in the art, and all such analogs are intended to be covered by the terminology set forth herein.

[0073] This disclosure includes all compounds of this disclosure with acceptable isotopic labeling, wherein one or more atoms are replaced by atoms having the same atomic number but with an atomic mass or mass number different from those normally found in nature.

[0074] Examples of suitable isotopes to be included in the compounds disclosed herein include: isotopes of hydrogen, such as... 2 H and 3H; isotopes of carbon, such as 11 C 13 C and 14 C; isotopes of chlorine, for example 36 Cl; isotopes of fluorine, for example 18 F; Isotopes of iodine, such as 123 I, 124 I and 125 I; Isotopes of nitrogen, such as 13 N and 15 N; isotopes of oxygen, such as 15 O、 17 O and 18 O; isotopes of phosphorus, such as 32 P; and isotopes of sulfur, such as 35 S.

[0075] Certain isotope-labeled compounds disclosed herein, such as those conjugated with radioactive isotopes, can be used in diagnostics and other research. Radioactive isotope tritium (i.e., 3 H) and carbon-14 (i.e. 14 C) They are particularly suitable for this purpose because they are easy to introduce and easy to detect.

[0076] Using heavier isotopes such as deuterium (i.e., 2 H) substitution can provide some advantages resulting from greater stability, and may therefore be preferred in some cases.

[0077] Isotopically labeled compounds of this disclosure can generally be prepared by conventional techniques known to those skilled in the art or by methods similar to those described in the appended examples and preparations, using a suitable isotopically labeled reagent instead of the previously used unlabeled reagent.

[0078] For example, deuterated compounds can be readily prepared using methods known in the art. For instance, the preparation of deuterated organometallic complexes is described in U.S. Patent No. 8,557,400, Patent Publication WO 2006 / 095951, and U.S. Patent Application Publication US 2011 / 0037057 (the entire contents of which are incorporated herein by reference)

[0079] When used herein, any specifically listed substituent (e.g., but not limited to methyl, phenyl, pyridyl, etc.) includes its undeuterated, partially deuterated, and fully deuterated forms. Similarly, some types of substituents (e.g., but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc.) also include their undeuterated, partially deuterated, and fully deuterated forms. Unless otherwise specified, atoms in chemical structures where the chemical bonds are not completely filled by H or D should be considered to include their undeuterated, partially deuterated, and fully deuterated forms. For example, The chemical structure implies variants including C6H6, C6D6, C6H3D3, and any other partially deuterated forms. Some common basic partially or fully deuterated groups include, but are not limited to, CD3, CD2C(CH3)3, C(CD3)3, and C6D5. Similarly, in cases where a partially or fully defined atomic structure shows that a particular position can be either deuterated or hydrogen, the same atomic structure in which one, two, or at most all deuterated atoms are replaced by hydrogen is also conceivable.

[0080] It should be understood that when a molecular fragment is described as a substituent or attached to another structural part, its name can be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., benzene, naphthalene, dibenzofuran). In this document, these different ways of naming substituents or attached fragments are considered equivalent.

[0081] In some cases, a pair of substituents in a molecule can be linked or fused to form a ring. Preferred rings are five- to nine-membered carbon rings or heterocycles, including both cases where a portion of the ring formed by the pair of substituents is saturated and cases where a portion of the ring formed by the pair of substituents is unsaturated. In other cases, a pair of adjacent substituents can be linked or fused to form a ring. As used herein, “adjacent” means that the two substituents involved can be adjacent to each other on the same ring, or on two neighboring rings having the two closest available substituted positions (e.g., the 2,2' position in biphenyl or the 1,8 position in naphthalene).

[0082] B. Compounds disclosed herein

[0083] In one aspect, this disclosure provides a first ligand L A The compound, the first ligand L A Structure of Formula I:

[0084] Formula I,

[0085] in:

[0086] Structural part A and structural part B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring;

[0087] Z 1 -Z 4 Each can be either C or N independently;

[0088] K is selected from the following group: direct bond, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R) α (R) β ), and Si(R) α (R) β );

[0089] R A and R B Each can be used independently to represent monosubstitution up to the maximum permissible substitution, or no substitution.

[0090] R α R β R A and R B Each is hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof;

[0091] At least one of the following conditions must be true:

[0092] i) at least one R A Or R B It includes an olefin structural moiety, wherein if the olefin structural moiety forms part of a ring, the ring is not aromatic; or

[0093] ii) At least one of structural moiety A or structural moiety B contains a non-aromatic ring having at least one olefinic structural moiety;

[0094] L A Fitted in metal M;

[0095] M is selected from the following groups: Os, Ir, Pd, Pt, Rh, Re, Ru, Cu, Ag, and Au;

[0096] M can ligand other ligands;

[0097] L AIt can be linked with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands;

[0098] Any two substituents can be linked or fused to form a ring.

[0099] In some implementations, if M is Ir, then at least one of the following conditions is true:

[0100] (1) K is not a direct key;

[0101] (2) Both structural part A and structural part B are polycyclic fused ring systems;

[0102] (3) Z 4 It is C, and structural part B is a polycyclic fused ring system;

[0103] (4) The compound contains ligand L B The ligand L B It includes a structural portion G, wherein the structural portion G is coordinated to a metal M and is a polycyclic fused ring system, wherein each ring of the polycyclic fused ring system of the structural portion G is independently a 5- to 10-membered carbon ring or heterocyclic ring; or

[0104] (5) Z 4 It is C, and structural part B is a single ring, while structural part A is a multi-ring containing at least two rings.

[0105] In some implementation schemes, Z 4 It is C, and structural part B is a polycyclic fused ring system with exactly two rings. In some embodiments, Z 4 It is C, and structural part B is a polycyclic fused ring system having at least four rings. In some embodiments, Z 4 C is a polycyclic fused ring system having three rings, and structural moiety B is substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. In some such embodiments, the aryl or heteroaryl group may be a polycyclic fused ring system substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. In some such embodiments, the aryl or heteroaryl group may be a tricyclic fused ring system substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0106] In some embodiments, the compound comprises ligand L B The ligand L BThe system comprises a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system comprising at least two rings, wherein each ring of the polycyclic fused ring system comprising the structural moiety G is independently a 5- to 10-membered carbon ring or a heterocyclic ring. In some such embodiments, the at least two rings are substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0107] In some embodiments, the compound comprises ligand L B The ligand L B The system comprises a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system comprising at least three rings, wherein each ring of the polycyclic fused ring system comprising the structural moiety G is independently a 5- to 10-membered carbon ring or a heterocyclic ring. In some such embodiments, the at least three rings are substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0108] In some embodiments, the compound comprises ligand L B The ligand L B The system comprises a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system comprising at least four rings, wherein each ring of the polycyclic fused ring system comprising the structural moiety G is independently a 5- to 10-membered carbon ring or a heterocyclic ring. In some such embodiments, the at least four rings are substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0109] In some embodiments, the compound comprises ligand L B The ligand L B The system comprises a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system comprising at least five rings, wherein each ring of the polycyclic fused ring system comprising the structural moiety G is independently a 5- to 10-membered carbon ring or a heterocyclic ring. In some such embodiments, the at least five rings are substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0110] In some implementation schemes, Z 4The structure is C, and structural moiety B is a monocyclic ring, while structural moiety A is a polycyclic system comprising at least two rings. In some such embodiments, the monocyclic structural moiety B is substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. In some such embodiments, the polycyclic structural moiety A comprises at least two rings and is substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. In some such embodiments, the polycyclic structural moiety A comprises at least three rings and is substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. In some such embodiments, the polycyclic structural moiety A comprises at least four rings and is substituted with at least one deuterium, an electron-withdrawing group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof.

[0111] In some implementations, the first ligand L A It is essentially composed of Formula I. In some embodiments, the first ligand L A It has the structure of Formula I.

[0112] In some implementations, the first ligand L A no:

[0113] , , , , ,or .

[0114] In some implementations, at least one R α R β R A Or R B Selected from the generic substituents defined herein. In some embodiments, at least one R α Selected from the generic substituents defined herein. In some embodiments, at least one R β Selected from the generic substituents defined herein. In some embodiments, at least one R A Selected from the generic substituents defined herein. In some embodiments, at least one R B Selected from the generic substituents defined herein. In some embodiments, at least one R α R β R A Or R B Selected from the preferred general substituents defined in this document.

[0115] In some implementations, each R α R β RA and R B Substituents that are independently hydrogen or selected from the group consisting of preferred generic substituents as defined herein. In some embodiments, each R α R β R A and R B Substituents that are independently hydrogen or selected from the group consisting of more preferred generic substituents as defined herein. In some embodiments, each R α R β R A and R B Substituents that are independently hydrogen or selected from the group consisting of: even more preferred generic substituents as defined herein. In some embodiments, each R α R β R A and R B Substituents that are independently hydrogen or selected from the group consisting of the most preferred general substituents as defined herein.

[0116] In some implementations, each R α R β R A and R B The substituent is independently hydrogen or selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioalkyl and combinations thereof.

[0117] In some embodiments of Formula I, at least one R α R β R A and R B It is partially or completely deuterated. In some implementations, at least one R α Or R β It is partially or completely deuterated. In some implementations, at least one R A It is partially or completely deuterated. In some implementations, at least one R B It is partially or completely deuterated.

[0118] Despite Z 1 -Z 2 The bonds between them are shown as single bonds, and it should be understood that they can be any other bonds required to form the rings of the applicable structural part A. This also applies to the structures of any other generalized rings or structural parts disclosed herein, including Z. 3 -Z 4 .

[0119] In some implementations, structural portions A and B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- or 6-membered carbon ring or heterocyclic ring.

[0120] In some embodiments, structural portions A and B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- or 6-membered aryl or heteroaryl ring.

[0121] In some embodiments, structural part A is selected from the following list of cyclic structural parts: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azirabenzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, azirabenzoxazole, benzothiophene, azirabenzothiophene, benzo ...benzo[3,2-b]benzo[3,2- Thiazole, azirbenzathiazole, benzo[selenyl]phenanthrene, azirbenzaselenyl, indene, azirindene, indole, azirindole, benzimidazole, azirbenzamidazole, benzo[benzamidazole]phenanthrene, azirbenzamidazole, carbazole, azircarbazole, naphthemidazole, dibenzofuran, azirdibenzofuran, dibenzothiophene, azirdibenzothiophene, quinoxaline, phthalazine, phenanthrene, azirphenanthrene, anthracene, aziranthracene, phenanthrene, and azirfluorene.

[0122] In some embodiments, the azaheteromorph includes a nitrogen atom on the benzene ring. In some embodiments, the azaheteromorph includes a nitrogen atom on the benzene ring, and the nitrogen atom is coordinated to a metal M.

[0123] In some implementations, structural part A is a single ring.

[0124] In some embodiments, structural part A is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0125] In some implementations, structural part A is pyridine, pyrimidine, or imidazole.

[0126] In some implementations, structural part A is a polycyclic fused ring system.

[0127] In some embodiments, structural part A is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, azirabenzofuran, phenanthrene[3,2-b]benzofuran, benzoxazole, azirabenzoxazole, benzothiophene, azirabenzothiophene, benzothiazole, azirabenzothiazole, benzoselenene, azirabenselenene, indole, aziraindole, benzimidazole, azirabenzimidazole, benzobenzimidazole, azirabenzimidazole, carbazole, aziracarbazole, dibenzofuran, aziradibenzofuran, dibenzothiazole, aziradibenzothiazole, phthalazine, phenanthrene, aziraphenanthrene, anthracene, aziraanthracene, phenanthridine, fluorene, and azirafluorene.

[0128] In some embodiments, structural part A is benzimidazole, quinoline, isoquinoline, benzothiazole, azirbenzothiazole, dibenzothiophene, or azirdibenzothiophene.

[0129] In some embodiments, structural moiety A is benzimidazole. In some embodiments, structural moiety A is isoquinoline. In some embodiments, structural moiety A is azirconothiazole. In some embodiments, structural moiety A is azirdibenzothiophene.

[0130] In some implementations, the ring coordinated to the metal M is a pyrimidine.

[0131] In some implementations, structural part A is azirdibenzothiophene cyclized from a benzene ring.

[0132] In some implementations, structural portion B is selected from the list of ring-shaped structural portions defined herein.

[0133] In some implementations, structural part B is a single ring.

[0134] In some embodiments, structural part B is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0135] In some implementations, structural part B is benzene.

[0136] In some implementations, structural part B is a polycyclic fused ring system.

[0137] In some embodiments, structural part B is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, azabenzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimidazole, azabenzimidazole, benzobenzimidazole, azabenzimidazole, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

[0138] In some implementations, structural part B is naphthalene or dibenzofuran.

[0139] In some embodiments, structural portion B is cyclized through structural portion B', wherein structural portion B' is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring.

[0140] In some embodiments, structural moiety B' is a 5- or 6-membered carbon ring or heterocyclic ring. In some embodiments, structural moiety B' is a 5- or 6-membered aryl or heteroaryl ring.

[0141] In some implementations, structural portion B' is selected from the list of ring-shaped structural portions defined herein.

[0142] In some implementations, structural part B' is a single ring.

[0143] In some embodiments, structural part B' is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0144] In some embodiments, structural moiety B' is benzene or pyridine. In some embodiments, structural moiety B' is benzene. In some embodiments, structural moiety B' is pyridine.

[0145] In some implementations, structural part B' is a polycyclic fused ring system.

[0146] In some embodiments, structural part B' is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, azabenzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimidazole, azabenzimidazole, benzobenzimidazole, azabenzimidazole, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiphene, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

[0147] In some embodiments, structural part B' is naphthalene, quinoline, benzofuran, azirbenzofuran, benzothiophene, azirbenzothiophene, benzimazole, azirbenzoimazole, carbazole, azircarbazole, dibenzofuran, azirdibenzofuran, dibenzothiophene, or azirdibenzothiophene.

[0148] In some embodiments, structural moiety B' is naphthalene. In some embodiments, structural moiety B' is benzofuran.

[0149] In some implementations, structural moiety B is dibenzofuran and structural moiety B' is benzene or naphthalene.

[0150] In some embodiments, at least one of structural portions A and / or B may be an independent polycyclic fused ring structure. In some embodiments, at least one of structural portion A or structural portion B may be an independent polycyclic fused ring structure comprising at least two fused rings. In some embodiments, the polycyclic fused ring structure has one 6-membered ring and one 5-membered ring. In some such embodiments, the 5-membered ring or the 6-membered ring may be configured with the metal. In some embodiments, the polycyclic fused ring structure has two 6-membered rings. In some embodiments, at least one of structural portion A or structural portion B may be independently selected from the group consisting of benzofuran, benzothiophene, benzoselenene, naphthalene, and their nitrogen heteromorphs.

[0151] In some embodiments, at least one of structural moiety A or structural moiety B may independently be a polycyclic fused ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused ring structure has two 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to a ring coordinated to metal M, and a second 6-membered ring is fused to the 5-membered ring. In some embodiments, at least one of structural moiety A or structural moiety B may independently be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenene, and their nitrogen heteromorphs. In some such embodiments, at least one of structural moiety A or structural moiety B may independently be further substituted at the ortho or meta position of the O, S, or Se atom, with the substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the nitrogen heteromorph contains exactly one N atom at the 6-position (ortho to the O, S, or Se), while the substituent is at the 7-position (meta to the O, S, or Se).

[0152] In some embodiments, at least one of structural part A or structural part B may independently be a polycyclic fused ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused ring structure comprises three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to a 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.

[0153] In some embodiments, at least one of structural portion A or structural portion B may independently be a multi-ring fused ring structure comprising at least five fused rings. In some embodiments, the multi-ring fused ring structure comprises four 6-membered rings and one 5-membered ring, or comprises three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the two 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the two 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 a ring coordinated with metal M, a second 6-membered ring is fused to the 5-membered ring, a third 6-membered ring is fused to the second 6-membered ring, and a fourth 6-membered ring is fused to the third 6-membered ring.

[0154] In some embodiments, at least one of structural moiety A or structural moiety B may independently be a nitrogen-heterogeneous form of the polycyclic fused ring described above. In some such embodiments, at least one of structural moiety A or structural moiety B may independently contain exactly one nitrogen-atom. In some such embodiments, at least one of structural moiety A or structural moiety B contains exactly two nitrogen-atoms, which may be in one ring or in two different rings. In some such embodiments, the ring containing the nitrogen-atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring containing the nitrogen-atom is separated from the metal M atom by at least three other rings. In some such embodiments, each adjacent position of the nitrogen-atom is substituted.

[0155] In some implementation schemes, Z 1 It is N and Z 4 It is C. In some implementations, Z 1 It is N, Z 4 It is C, and Z 2 and Z 3 Both are C.

[0156] In some implementation schemes, Z 1 It is a carbene carbon and Z 4 It is C. In some implementations, Z1 It's carbene carbon, Z 4 It's C, Z 2 It is N, and Z 3 It's C.

[0157] In some implementation schemes, Z 2 and Z 3 Both are C.

[0158] In some implementation schemes, Z 2 Or Z 3 At least one of them is N. In some implementations, Z 2 It is N and Z 3 It's C.

[0159] In some implementation schemes, Z 2 It is N. In some implementations, Z 3 It is N.

[0160] In some implementations, K is a direct key.

[0161] In some implementations, K is O, S, or Se. In some implementations, K is O.

[0162] In some implementations, K is selected from the group consisting of: N(R) α ), P(R α ), and B(R) α ).

[0163] In some implementations, K is selected from the group consisting of: C(R) α (R) β ) and Si(R α (R) β ).

[0164] In some implementations, the metal M is Ir.

[0165] In some implementations, the metal M is Pt.

[0166] In some implementations, K is not a direct key.

[0167] In some embodiments, metal M is Ir and K is not a direct bond. In some such embodiments, K is O, S, or Se. In some embodiments, metal M is Ir and K is O. In some embodiments, K is selected from the group consisting of: N(R) α ), P(R α ), and B(R) α In some implementations, K is selected from the group consisting of: C(R) α (R) β ) and Si(R α (R)β ).

[0168] In some implementations, structural part A and structural part B are both polycyclic fused ring systems.

[0169] In some implementations, metal M is Ir, and structural part A and structural part B are both polycyclic fused ring systems.

[0170] In some implementations, structural portion A has exactly two fused rings.

[0171] In some embodiments, structural portion A contains at least three fused rings. In some embodiments, structural portion A contains at least four fused rings. In some embodiments, structural portion A contains at least five fused rings.

[0172] In some implementation schemes, Z 4 It is C, and structural part B is a polycyclic fused ring system having exactly two fused rings or at least four rings.

[0173] In some implementations, metal M is Ir, Z 4 C is a polycyclic fused ring system having exactly two fused rings or at least four rings. In some embodiments, structural part B has exactly two fused rings. In some embodiments, structural part B is naphthalene.

[0174] In some embodiments, structural moiety B comprises at least four fused rings. In some embodiments, structural moiety B is a dibenzofuran and further cyclically formed through structural moiety B', wherein structural moiety B' is benzene or pyridine. In some embodiments, structural moiety B is an azadibenzofuran and further cyclically formed through structural moiety B', wherein structural moiety B' is benzene or pyridine.

[0175] In some embodiments, structural moiety B comprises at least five fused rings. In some embodiments, structural moiety B is a dibenzofuran and further cyclically formed through structural moiety B', wherein structural moiety B' is naphthalene, quinoline, or isoquinoline. In some embodiments, structural moiety B is an azadibenzofuran and further cyclically formed through structural moiety B', wherein structural moiety B' is naphthalene, quinoline, or isoquinoline.

[0176] In some embodiments, the compound comprises ligand L B The ligand L B It includes a structural part G, wherein the structural part G is located in a metal M and is a polycyclic fused ring system comprising at least four rings, wherein each ring of the polycyclic fused ring system of the structural part G is independently a 5- to 10-membered carbon ring or a heterocyclic ring.

[0177] In some embodiments, the metal M is Ir, and the compound comprises a ligand L. B The ligand L B It includes a structural part G, wherein the structural part G is located in a metal M and is a polycyclic fused ring system comprising at least four rings, wherein each ring of the polycyclic fused ring system of the structural part G is independently a 5- to 10-membered carbon ring or a heterocyclic ring.

[0178] In some embodiments, G has exactly four fused rings. In some embodiments, G contains at least five fused rings.

[0179] In some implementations, the metal M is Ir, and at least one of conditions (1)-(4) is met.

[0180] In some implementations, two of conditions (1)-(4) are true. In some implementations, the metal M is Ir, and two of conditions (1)-(4) are true.

[0181] In some implementations, three of conditions (1)-(4) are true. In some implementations, the metal M is Ir, and three of conditions (1)-(4) are true.

[0182] In some implementations, conditions (1)-(4) are all true. In some implementations, the metal M is Ir, and conditions (1)-(4) are all true.

[0183] In some embodiments, the compound comprises an electron-withdrawing group. In some embodiments, the electron-withdrawing group has a Hammett constant greater than 0. In some embodiments, the electron-withdrawing group has a Hammett constant equal to or greater than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.

[0184] In some implementations, the first ligand L A Contains electron-withdrawing groups selected from 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 k2Substituted or unsubstituted dibenzoboranecyclopentadiene, 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. , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ;

[0185] Each R k1 Indicates single substitution up to the maximum permissible substitution, or indicates no substitution;

[0186] Where Y G Selected from the following group: 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

[0187] Where R k1 R k2 R k3 R e and R f Each of them is independently hydrogen, or a substituent selected from the general substituents defined herein.

[0188] In some implementations, the first ligand L A Structures containing electron-withdrawing groups selected from the following EWG2 list:

[0189] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , ,and .

[0190] In some implementations, the first ligand L A Structures containing electron-withdrawing groups selected from the following EWG3 list:

[0191] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0192] In some implementations, the first ligand L A Structures containing electron-withdrawing groups selected from the following EWG4 list:

[0193] , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0194] In some implementations, the first ligand L A Structures containing π-electron-deficient electron-withdrawing groups selected from the following Pi-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 k3Substituted or unsubstituted dibenzoboranecyclopentadiene, 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. , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and The variables are the same as those defined previously.

[0195] In some embodiments, the compound comprises an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, the compound comprises an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0196] In some implementations, at least one R A It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0197] In some implementations, at least one R B It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0198] In some implementations, at least one R α Or R β It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R α Or R β It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R α Or R β It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R α Or R β It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R α Or R β It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0199] In some implementations, at least one R A It's not hydrogen.

[0200] In some implementations, at least one R A It contains at least one carbon atom. In some embodiments, at least one R A It contains at least two carbon atoms. In some embodiments, at least one R A It contains at least three carbon atoms. In some embodiments, at least one R A It contains at least four carbon atoms.

[0201] In some implementations, at least one R A It contains substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0202] In some implementations, at least one R A It contains electron-withdrawing groups.

[0203] In some implementations, at least one R A Includes electron-withdrawing groups selected from the EWG1 list as defined herein.

[0204] In some implementations, at least one R A Structure of Formula II: II;

[0205] Among them, ring F It consists of 5- to 10-membered carbon rings or heterocycles;

[0206] Where R F’ It indicates mono- or tri-substituted, or unsubstituted;

[0207] Where R 1’ R 2’ and R F’ Each is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and

[0208] Where R 1’ Or R 2’ At least one of them is neither hydrogen nor deuterium.

[0209] In some implementation schemes, ring F It is a 5- or 6-membered carbon ring or heterocyclic ring. In some implementations, ring F... It is a 5- or 6-membered aryl or heteroaryl ring.

[0210] In some implementation schemes, R 1’ and R 2’ Neither of them are hydrogen or deuterium.

[0211] In some implementation schemes, R 1’ and R 2’ Each is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof. In some embodiments, R 1’ and R 2’ The same. In some implementations, R 1’ and R 2’ different.

[0212] In some implementation schemes, R 1’ and R 2’ All contain at least one carbon atom. In some embodiments, R 1’ and R 2’ All contain at least two carbon atoms. In some implementations, R 1’ and R 2’ All contain at least three carbon atoms. In some implementations, R 1’ and R 2’ All contain at least four carbon atoms. In some implementations, R 1’ and R 2’ They all contain at least five carbon atoms.

[0213] In some implementations, at least one R F’ It is neither hydrogen nor deuterium.

[0214] In some implementations, at least one R F’ Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, silalkyl, germanalkyl, and combinations thereof.

[0215] In some implementation schemes, ring F Selected from the following group: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole and triazole.

[0216] In some implementations, at least one R A Structure of the included IIA: IIA, where X 1a X 2a and X 3a Each can be either C or N independently.

[0217] In some implementations, at least one R F’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R F’It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R F’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R F’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R F’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0218] In some implementation schemes, R 1’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, R 1’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, R 1’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, R 1’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, R 1’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0219] In some implementation schemes, R 2’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, R 2’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, R 2’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, R 2’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, R 2’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0220] In some implementations, bonded to X 2a R F’ Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof. In some embodiments, bonded to X 2a R F’ It is an alkyl group. In some embodiments, it is bonded to X. 2a R F’ It is aryl or heteroaryl. In some embodiments, it is bonded to X. 2a R F’ It is a silane. In some embodiments, it is bonded to X. 2aR F’ It is a germanyl group.

[0221] In some implementation schemes, X 1a X 2a and X 3a Both are C.

[0222] In some implementation schemes, X 1a X 2a Or X 3a At least one of them is N. In some implementations, X is exactly... 1a X 2a Or X 3a One of them is N.

[0223] In some implementation schemes, R F’ It is aryl. In some implementations, R F’ It is benzene.

[0224] In some implementations, two R A They are connected or fused together to form a non-aromatic ring containing at least one olefinic structural moiety.

[0225] In some implementations, at least one R B It's not hydrogen.

[0226] In some implementations, at least one R B It contains at least one carbon atom. In some embodiments, at least one R B It contains at least two carbon atoms. In some embodiments, at least one R B It contains at least three carbon atoms. In some embodiments, at least one R B It contains at least four carbon atoms.

[0227] In some implementations, at least one R B It contains substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0228] In some implementations, at least one R B It contains electron-withdrawing groups.

[0229] In some implementations, at least one R B Includes electron-withdrawing groups selected from the EWG1 list as defined herein.

[0230] In some implementations, two R B Connect or fuse to form a non-aromatic ring containing at least one olefinic structural moiety.

[0231] In some implementations, an R A And an RB Connect or fuse to form a ring.

[0232] In some implementations, at least one R A Or R B It has the structure of Formula III:

[0233] Formula III,

[0234] in:

[0235] If the olefin structural portion is directly bonded to structural portion A or structural portion B, then the dashed bond indicates a bond in structural portion A or structural portion B; or the dashed bond indicates a bond connected to an R bond respectively bonded to structural portion A or structural portion B. A Or R B The key;

[0236] n is 0, 1, 2, 3, or 4;

[0237] When n is 0, Equation III is directly bonded to structural part A or structural part B, or bonded to R that is bonded to structural part A or structural part B respectively. A Or R B .

[0238] Each of R1, R2, R3, R4 and R5 is independently hydrogen, or a substituent selected from the general substituents defined herein;

[0239] Any two substituents can be linked or fused to form a ring; and

[0240] R1, R2, R3, R4, or R5 can be connected to adjacent R... A Or R B Connect or fuse to form a ring.

[0241] In some implementations, at least one R A It has the structure of Formula III. In some embodiments, at least one R B It has the structure of Formula III.

[0242] In some embodiments, at least R1 is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least R1 is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least R1 is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least R1 is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least R1 is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0243] In some embodiments, at least R2 is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least R2 is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least R2 is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least R2 is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least R2 is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0244] In some embodiments, at least R3 is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least R3 is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least R3 is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least R3 is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least R3 is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0245] In some embodiments, if at least one R4 is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, if at least one R4 is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, if at least one R4 is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, if at least one R4 is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, if at least one R4 is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0246] In some embodiments, if at least one R5 is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, if at least one R5 is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, if at least one R5 is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, if at least one R5 is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, if at least one R5 is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0247] In some implementations, n is 0. In some implementations, n is 1. In some implementations, n is 2. In some implementations, n is 3. In some implementations, n is 4.

[0248] In some embodiments, R1 is hydrogen or deuterium. In some embodiments, R1 is hydrogen. In some embodiments, R1 is deuterium.

[0249] In some implementations, R1 is not hydrogen.

[0250] In some embodiments, R1 contains at least one carbon atom. In some embodiments, R1 contains at least two carbon atoms. In some embodiments, R1 contains at least three carbon atoms. In some embodiments, R1 contains at least four carbon atoms.

[0251] In some embodiments, R1 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0252] In some implementations, R1 contains an electron-withdrawing group.

[0253] In some embodiments, R1 contains an electron-withdrawing group selected from the EWG1 list as defined herein.

[0254] In some implementations, R2 is not hydrogen.

[0255] In some embodiments, R2 contains at least one carbon atom. In some embodiments, R2 contains at least two carbon atoms. In some embodiments, R2 contains at least three carbon atoms. In some embodiments, R2 contains at least four carbon atoms.

[0256] In some embodiments, R2 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0257] In some embodiments, R2 comprises an aryl or heteroaryl group. In some embodiments, R2 is an aryl group. In some embodiments, R2 is a heteroaryl group.

[0258] In some implementations, R2 contains an electron-withdrawing group.

[0259] In some embodiments, R2 contains an electron-withdrawing group selected from the EWG1 list as defined herein.

[0260] In some implementations, R3 is not hydrogen.

[0261] In some embodiments, R3 contains at least one carbon atom. In some embodiments, R3 contains at least two carbon atoms. In some embodiments, R3 contains at least three carbon atoms. In some embodiments, R3 contains at least four carbon atoms.

[0262] In some embodiments, R3 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0263] In some embodiments, R3 comprises an aryl or heteroaryl group. In some embodiments, R3 is an aryl group. In some embodiments, R3 is a heteroaryl group.

[0264] In some implementations, R3 contains an electron-withdrawing group.

[0265] In some embodiments, R3 contains an electron-withdrawing group selected from the EWG1 list as defined herein.

[0266] In some embodiments, R4 contains at least one carbon atom when present. In some embodiments, R4 contains at least two carbon atoms. In some embodiments, R4 contains at least three carbon atoms. In some embodiments, R4 contains at least four carbon atoms.

[0267] In some embodiments, when present, R4 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0268] In some embodiments, R5 contains at least one carbon atom when present. In some embodiments, R5 contains at least two carbon atoms. In some embodiments, R5 contains at least three carbon atoms. In some embodiments, R5 contains at least four carbon atoms.

[0269] In some embodiments, when present, R5 comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0270] In some embodiments, at least one of R2 or R3 comprises an aryl or heteroaryl group. In some embodiments, R2 is an aryl group. In some embodiments, R2 is a heteroaryl group. In some embodiments, R3 is an aryl group. In some embodiments, R3 is a heteroaryl group.

[0271] In some embodiments, R2 and R3 each independently comprise an aryl or a heteroaryl group. In some embodiments, both R2 and R3 are aryl groups. In some embodiments, both R2 and R3 are heteroaryl groups. In some embodiments, one of R2 and R3 is an aryl group, and the other of R2 and R3 is a heteroaryl group.

[0272] In some implementations, Formula III has an E configuration.

[0273] In some implementations, Formula III has a Z configuration.

[0274] In some implementation schemes, R 1 and R 2 They are joined or fused together to form a ring. In some embodiments, the ring is not aromatic.

[0275] In some implementation schemes, R 2 and R 3 They are joined or fused together to form a ring. In some embodiments, the ring is not aromatic.

[0276] In some implementations, at least one R A It includes the olefin structural portion.

[0277] In some implementations, at least one R A A structure comprising formula II or formula IIA, or at least one of them R F’ It includes the olefin structural portion.

[0278] In some implementations, at least one R B It includes the olefin structural portion.

[0279] In some implementations, at least one R A and at least one R B It includes the olefin structural portion.

[0280] In some embodiments, the olefin structural portion does not contain rings.

[0281] In some embodiments, at least one of structural part A or structural part B contains a non-aromatic ring having at least one olefinic structural part.

[0282] In some implementations, the non-aromatic ring is ring-formed onto structural portion A.

[0283] In some implementations, the non-aromatic ring is ring-formed onto structural portion B.

[0284] In some embodiments, the compound comprises a first non-aromatic ring having at least one olefinic structural moiety and a second non-aromatic ring having at least one olefinic structural moiety, wherein the first non-aromatic ring is cyclized to structural moiety A, and the second non-aromatic ring is cyclized to structural moiety B. In some embodiments, the non-aromatic ring does not comprise either structural moiety A or structural moiety B.

[0285] In some embodiments, structural portion A or structural portion B having an olefinic structural portion is a polycyclic fused ring structure, wherein the non-aromatic ring having the olefinic structural portion is the terminal ring of the polycyclic fused ring structure.

[0286] In some embodiments, the non-aromatic ring comprises cyclopentadiene or cyclohexene.

[0287] In some embodiments, the non-aromatic ring comprises cyclohexene, wherein the cyclohexene comprises at least one quaternary carbide ring atom. In some embodiments, the cyclohexene comprises at least two quaternary carbide ring atoms.

[0288] In some implementations, at least one R A Or R B It includes an olefinic structural moiety, and at least one of the structural moiety A or structural moiety B includes a non-aromatic ring having at least one olefinic structural moiety.

[0289] In some implementation schemes, R α Or R β At least one of them is not hydrogen.

[0290] In some implementation schemes, R α Or R β At least one of them contains at least one carbon atom. In some embodiments, R α Or R β At least one of them contains at least two carbon atoms. In some embodiments, R α Or R β At least one of them contains at least three carbon atoms. In some embodiments, R α Or R β At least one of them contains at least four carbon atoms.

[0291] In some implementation schemes, R α Or R β At least one of them contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0292] In some implementation schemes, R α Or R β At least one of them contains an electron-withdrawing group.

[0293] In some implementation schemes, R α Or R β At least one of them contains an electron-withdrawing compound selected from the EWG1 list as defined herein.

[0294] In some implementation schemes, R α and R βThey connect or fuse together to form a ring.

[0295] In some embodiments, the olefin structural portion has a structure having formula IIIC: The olefin structural portion, wherein the structure of formula IIIC has formula P#, where # is an integer from 1 to 428, and each of P1 to P365 is a linear olefin structural portion selected from the structures defined in the following list A1:

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311] Furthermore, each of P366-P428 has the structure defined in list A2 of this document.

[0312] In some embodiments, the olefin structural portion forms part of a ring that is not aromatic and is or includes a structure of formula IIIA:

[0313] Formula IIIA;

[0314] in,

[0315] n is an integer between 0 and 10;

[0316] The structural part W is a 5-, 6-, or 7-membered non-aromatic ring;

[0317] R AB Indicates single substitution up to the maximum permissible substitution, or no substitution;

[0318] R G1 R G2 R G3 and R AB Each is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and

[0319] Any two substituents may optionally be linked or fused to form a ring.

[0320] In some embodiments, the olefinic structural portion of Formula IIIC is selected from the structures P366-P428 as defined in List A2 below:

[0321]

[0322]

[0323] In some embodiments, the olefin structural portion forms part of a ring, which is achieved by using The two carbon atoms of the label are attached to structural moiety A or structural moiety B, and the olefin structural moiety comprises or has a structure of formula IIIB:

[0324] Formula IIIB,

[0325] in,

[0326] n1 and n2 are each independent integers from 0 to 20;

[0327] R AB Indicates single substitution up to the maximum permissible substitution, or indicates no substitution;

[0328] Each R AB Independently, it is hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and

[0329] Any two substituents may optionally be linked or fused to form a ring.

[0330] In some embodiments, n1 is 0 and n2 is 1. In some embodiments, n1 is 1 and n2 is 0. In some embodiments, n2 is 0 and n1 is 0. In some embodiments, n1 is 1 and n2 is 1. In some embodiments, the structure of Formula IIIB is bonded to two adjacent atoms of structural portion A. In some embodiments, the structure of Formula IIIB is bonded to two adjacent atoms of structural portion B.

[0331] In some embodiments, the olefin structural portion is selected from structures W1-W23 of the following list A3:

[0332] , , , , , , , , , , , , , , , , , , , , , ,and .

[0333] In some implementations, the ligand L A The structure is selected from the following List 1:

[0334] , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0335] in:

[0336] T is selected from the following groups: B, Al, Ga, and In;

[0337] K 1’ Selected from the following group: single bond, O, S, NR e PR e , BR e CR e R f and SiR e R f ;

[0338] Y 1 -Y 118 and V 1 -V 129 Each of them is independently selected from C and N;

[0339] Y a’ Each of Y' and Y'' is independently selected from the following group: BR e , BR e R f, NR e PR e , P(O)R e , O, S,Se, C=O, C=S, C=Se, C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f and GeR e R f ;

[0340] Y drawn by dashed lines 24 and V 1 Y 37 and V 1 Y 56 and V 1 Y 24 and V 7 Y 37 and V 7 Y 71’ and V 7 The single key can be optionally present;

[0341] Y drawn by dashed line 8 -W 1 -V 1 Y 32 -W 1 -V 1 Y 8 -W 1 -V 7 Y 32 -W 1 -V 7 The single bond groups between them can be arbitrarily present, and when single bond groups are present, their respective groups V 1 V 7 Y 8 and Y 32 It's carbon, W 1 Selected from the following groups: direct bonds, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR', and GeRR', when Y 8 -W 1 -V 1 Y 32 -W 1 -V 1 Y 8 -W 1 -V 7 Y 32-W 1 -V 7 If the single bond between them does not exist, then W 1 It does not exist either;

[0342] Y drawn by dashed line 8 and W 2 W 2 and V 7 The single bond between them can be arbitrarily present, and when it is present, then V 7 and Y 8 Each is carbon, W 2 Is it B, N, P, CR, SiR, or GeR, when Y 8 and W 2 W 2 and V 7 If the single bond between them does not exist, then W 2 Selected from the following groups: direct bonds, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR', and GeRR';

[0343] Is with V 5 -V 8 V 13 -V 16 Or V 25 -V 28 One of the connection points;

[0344] R a’ , R b’ , R c’ and R d’ Each of the terms in the alphabet independently represents one to the maximum allowed number of substitutions, or represents no substitution;

[0345] R, R', R a1 , R b1 , R c1 , R d1 , R a’ , R b’ , R c’ , R d’ , R e and R f Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof;

[0346] R, R', R a1 , R b1 , R c1 , R d1 , R a’ , R b’ , R c’ , R d’ , R e and R f Any two substituents can fuse or connect to form a ring or a polydentate ligand; and

[0347] R a’ Or R b’ At least one of them is a structure that either contains or includes formula III or formula IIIA, or is selected from list A1 or list A2; or at least one of the above structures is fused with a structure of formula IIIB, or is fused with a structure selected from list A3 as defined herein.

[0348] In which ligand L A Selected from some implementation schemes in List 1, V 13 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 14 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 15 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 16 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 25 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 26 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 27 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, V 28 It is a carbon atom bonded to a 5- or 6-membered nitrogen-containing ring in the top structural portion. In some embodiments, Y and Y Each is O independently. In some implementations, Y a’ It is NR And R It is or includes the structure of Formula II or Formula IIA. In such an implementation, all those implementations related to Formula II or Formula IIA are equally applicable herein.

[0349] In some implementations, two R a’They are connected to form a fused ring. In some such embodiments, the fused ring may be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azabenzofuran, phenanthero[3,2-b]benzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimazole, azabenzimidazole, carbazole, azacarbazole, naphthemidazole, dibenzofuran, azadibenzofuran, dibenzothiazole, azadibenzothiazole, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene. In some such implementations, the fused ring may be benzene.

[0350] In which ligand L A Selected from some implementation schemes in List 1, Y a’ It can be NR And R You can select a group that consists of the following structure (list B1):

[0351] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , ,and ,

[0352] The dashed line is connected to N.

[0353] In which ligand L A In some implementation schemes selected from List 1, at least one R a’ Or R b’ Selected from the universal substituents defined in this paper. In which ligand L... A In some implementation schemes selected from List 1, at least one R a’ Or R b’ Selected from preferred universal substituents defined herein. In which ligand L... A In some implementation schemes selected from List 1, at least one R a’ Or R b’ It is partially or completely deuterated. In some implementations, at least one R a’ It is partially or completely deuterated. In some implementations, at least one R b’ It is partially or completely deuterated.

[0354] In which ligand L A In some implementation schemes selected from List 1, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0355] In which ligand L AIn some implementation schemes selected from List 1, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0356] In some implementations, the ligand L A Select the group consisting of the structure listed in List 2 below:

[0357] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ; , , and ,

[0358] wherein:

[0359] V 29 , V 30 , V 31 , V 32 , V 68 , V 73 , V 73 , V 77 , V 81 and V 85Each can be either C or N independently;

[0360] Y and Y Each is independently selected from the following groups: BR, BRR , NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR S=O, SO2, CRR SiRR , and GeRR ;

[0361] W 1 Selected from the following groups: direct bonds, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR S=O, SO2, CRR P(O)R, SiRR , and GeRR ;

[0362] R a’ R b’ R c’ and R d’ Each can independently represent zero, one, or the maximum permissible number of substitutions up to its associated ring;

[0363] R a1 R b1 R c1 R a’ R b’ R c’ R d’ R and R Each is independently hydrogen, or a substituent selected from the general substituents defined herein;

[0364] R a’ R b’ R c’ and R d’ The two substituents can fuse or connect to form a ring or a polydentate ligand; and

[0365] R a’ Or R b’ At least one of them is or contains a structure of formula III or formula IIIA, or is selected from list A1 or list A2; or at least one of the above structures is fused to a structure of formula IIIB, or is fused to a structure selected from list A3 as defined herein.

[0366] In which ligand L A Selected from some implementation schemes in List 2, V 29It is C. In some implementations, V 29 It is N. In some implementations, V 30 It is N. In some implementations, V 30 It is C. In some implementations, V 31 It is N. In some implementations, V 31 It is C. In some implementations, V 32 It is N. In some implementations, V 32 It is C. In some implementations, Y a’ It is NR And R It is or includes the structure of Formula II or Formula IIA. In such an implementation, all those implementations related to Formula II or Formula IIA are equally applicable herein.

[0367] In which ligand L A Selected from some implementation schemes in List 2, Y a’ It can be NR And R It can be selected from the structure of list B1 defined in this article.

[0368] In some implementations, two R a’ They are connected to form a fused ring. In some such embodiments, the fused ring may be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azabenzofuran, phenanthero[3,2-b]benzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimazole, azabenzimidazole, carbazole, azacarbazole, naphthemidazole, dibenzofuran, azadibenzofuran, dibenzothiazole, azadibenzothiazole, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene. In some such implementations, the fused ring may be benzene.

[0369] In which ligand L A Selected from some implementation schemes in List 2, at least one R a’ Or R b’ Selected from the universal substituents defined in this paper. In which ligand L... A Selected from some implementation schemes in List 2, at least one R a’ Or R b’ Selected from preferred universal substituents defined herein. In which ligand L... A Selected from some implementation schemes in List 2, at least one R a’ Or Rb’ It is partially or completely deuterated. In some implementations, at least one R a’ It is partially or completely deuterated. In some implementations, at least one R b’ It is partially or completely deuterated. In some implementations, at least one R B2 It is partially or completely deuterated.

[0370] In which ligand L A Selected from some implementation schemes in List 2, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R a’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0371] In which ligand L A Selected from some implementation schemes in List 2, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG1 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG2 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG3 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the EWG4 list as defined herein. In some embodiments, at least one R b’ It is or contains an electron-withdrawing group selected from the Pi-EWG list as defined herein.

[0372] In some implementations, ligand L A Selected from L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EA Selected from P1-P428, R EB R ECR ED R EE and R EF Each is independently selected from U1-U126; and L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1)toL Aa-150 Each of -(P428)(U126)(U126)(U126)(U126)(U126) is defined in the following list 3:

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403] P1-P428 have the structures defined in List A1 and List A2 in this document;

[0404] U1-U126 have the structures defined in the following list C:

[0405] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， , ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , ,and .

[0406] In the above implementation scheme regarding the combination of List 3, R EA Selected from P1-P428, and the rest R EB R EC R ED R EE and R EF Each is independently U1-U126. However, it should be understood that as long as R... EA R EB R EC R ED R EE Or R EF If at least one group is selected from P1-P428, then the remaining groups can each be independently selected from U1-U126. In some embodiments, R is specifically selected from P1-P428. EA R EB R EC R ED R EE Or R EF One of them is selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC R ED R EE Or R EF Two of the groups are selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC R ED R EE Or R EF Three of the groups are selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC RED R EE Or R EF Four of them are selected from P1-P428, and the remaining groups are each independently selected from U1-U126.

[0407] More specifically, the following ligands are also covered, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EB Selected from P1-P428; R EA R EC R ED R EE and R EF Each is independently selected from U1-U126; and L Aa-1 -(U1)(P1)(U1)(U1)(U1)(U1)(U1)toL Aa-150 Each of -(U126)(P428) (U126)(U126)(U126)(U126) has the corresponding structure in List 3.

[0408] More specifically, the following ligands are also covered, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EC Selected from P1-P428; R EA R EB R ED R EE and R EF Each is independently selected from U1-U126; and L Aa-1 -(U1)(U1)(P1)(U1)(U1)(U1)toL Aa-150 Each of -(U126)(U126) (P428)(U126)(U126)(U126) has the corresponding structure in List 3.

[0409] More specifically, the following ligands are also covered, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R)EF ), where n is an integer from 1 to 150; R ED Selected from P1-P428; R EA R EB R EC R EE and R EF Each is independently selected from U1-U126; and L Aa-1 -(U1)(U1)(U1)(P1)(U1)(U1)toL Aa-150 Each of -(U126)(U126) (U126)(P428)(U126)(U126) has the corresponding structure in List 3.

[0410] More specifically, the following ligands are also covered, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EE Selected from P1-P428; R EA R EB R EC R ED and R EF Each is independently selected from U1-U126; and L Aa-1 -(U1)(U1)(U1)(U1)(P1)(U1)toL Aa-150 Each of -(U126)(U126) (U126)(U126)(P428)(U126) has the corresponding structure in List 3.

[0411] More specifically, the following ligands are also covered, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EF Selected from P1-P428; R EA R EB R EC R ED and R EE Each is independently selected from U1-U126; and L Aa-1 -(U1)(U1)(U1)(U1)(U1)(P1) to L Aa-150Each of -(U126)(U126) (U126)(U126)(U126)(P428) has the corresponding structure in List 3.

[0412] Furthermore, the following ligands are also included, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EA R EB R EC R ED R EE Or R EF Two of them are selected from P1-P428, and the remaining four groups are each independently selected from U1-U126, having the corresponding structures in List 3.

[0413] Furthermore, the following ligands are also included, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EA R EB R EC R ED R EE Or R EF Three of them are selected from P1-P428, and the remaining three groups are each independently selected from U1-U126, having the corresponding structures in List 3.

[0414] Furthermore, the following ligands are also included, for example: L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ), where n is an integer from 1 to 150; R EA R EB R EC R ED R EE Or R EF Four of them are selected from P1-P428, and the remaining two groups are each independently selected from U1-U126, having the corresponding structures in List 3.

[0415] In short, this disclosure is intended to cover all of the above-described embodiments / combinations, even if some of these combinations are not specifically and fully listed, but can be readily conceived or understood. It should also be understood that all of the above-described L... A The implementation schemes can all be applied in the same way to all general and specific L disclosed herein. B and / or L C Combinations of ligands, even if they are not explicitly or specifically listed. However, all such combinations are within the scope of this disclosure.

[0416] In some implementations, ligand L A Selected from L AAg , where g is an integer from 1 to 2^16, and L AA1 -L AA216 Each of the following is defined (List 3a):

[0417] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， , , , , , , , , , , , , , ， , ， , ， , , , , , , , , , , , , ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0418] In some embodiments, the compound has the following formula: M(L A ) p (L B ) q (L C ) r L B and L C All are bidentate ligands; and p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of metal M.

[0419] In some embodiments, the compound has the formula selected from the group consisting of: Ir(L A )3,Ir(L A (L) B )2,Ir(L A )2(L B ), Ir(L A )2(L C ), and Ir(L A (L) B (L) C ), where L A L B and L C They are different.

[0420] In some implementations, L B It is a substituted or unsubstituted phenylpyridine, and L C It is either substituted or unsubstituted acetylacetone.

[0421] In some embodiments, the compound has the following formula: Pt(L A (L) B ), where L A and L B They can be the same or different.

[0422] In some implementations, L A and L B They connect together to form tetradentate ligands.

[0423] In some implementations, L B and L C Each group is independently selected from the following groups, which are composed of the structures listed in Table 4:

[0424] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0425] in:

[0426] T is selected from the following groups: B, Al, Ga, and In;

[0427] K 1’ Selected from the following group: single bond, O, S, NR e PR e BR e CR e R f , and SiR e Rf ;

[0428] Y 1 -Y 13 Each of them is independently selected from C and N;

[0429] Y Selected from the following group: BR e BR e R f NR e PR e P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f , and GeR e R f ;

[0430] R e and R f They can be fused or joined to form a ring;

[0431] R a R b R c and R d Each can be used independently to represent monosubstitution up to the maximum allowed number of substitutions, or to represent no substitution;

[0432] R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and

[0433] R a1 R b1 R c1 R d1 R a R b Rc and R d Any two substituents can fused or joined to form a ring or a polydentate ligand.

[0434] In which ligand L B Selected from some implementation schemes in List 4, R a R b R c Or R d At least one of them is a structure that either contains formula III or formula IIIA, or is selected from list A1 or list A2; or at least one of the above structures is fused with a structure of formula IIIB, or is fused with a structure selected from list A3 described herein.

[0435] In some implementations, L B and L C Each group is independently selected from the structures listed in Table 5 below:

[0436] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0437] in:

[0438] R a ', R b ', R c ', R d 'and R e Each can independently represent zero, one, or up to the maximum allowed number of substitutions for its associated ring;

[0439] R a ', R b ', R c ', R d 'and R e Each of the following substituents is independently hydrogen or selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and

[0440] R a ', R b ', R c ', R d 'and R e The two substituents in ' can fused or connected to form a ring or a polydentate ligand.

[0441] In which ligand L B Selected from some implementation schemes in List 5, R a ', R b ', R c ', R d 'or R e At least one of them is or contains a structure of formula III or formula IIIA, or is selected from list A1 or list A2; or at least one of the above structures is fused with a structure of formula IIIB, or is fused with a structure selected from list A3 described herein.

[0442] In some implementations, L B Structures including the following:

[0443] ,

[0444] The variables are the same as those defined above. In some implementations, Y 1a -Y 4a Both are carbon. In some implementation schemes, Y 1a -Y 4aAt least one of them is N. In some implementations, exactly Y 1a -Y 4a One is N. In some implementations, Y 1a It is N. In some implementations, Y 2a It is N. In some implementations, Y 3a It is N. In some implementations, Y 4a It is N. In some implementations, at least one R a It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, at least one R a It is a tertiary alkyl group.

[0445] In some implementation schemes, Y 1a It is carbon and is connected to R a1 In some such implementations, R a1 It can be selected from the generic substituents defined herein. In some such implementations, R a1 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R a1 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R a1 It is a tertiary alkyl group. In some embodiments, Y 2a It is carbon and is connected to R a2 In some such implementations, R a2 It can be selected from the generic substituents defined herein. In some such implementations, R a2 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R a2 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R a2 It is a tertiary alkyl group. In some embodiments, Y 3a It is carbon and is connected to R a3 In some such implementations, R a3 It can be selected from the generic substituents defined herein. In some such implementations, R a3 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R a3 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R a3 It is a tertiary alkyl group. In some embodiments, Y 4a It is carbon and is connected to R a4 In some such implementations, R a4 It can be selected from the generic substituents defined herein. In some such implementations, R a4The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R a4 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R a4 It is a tertiary alkyl group.

[0446] In some implementation schemes, Y 3a It is C, and R is connected to it. a It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, Y 2a It is C, and R is connected to it. a It is a tertiary alkyl, silyl, or germanyl group.

[0447] In some implementation schemes, Y 1a -Y 3a It is C, Y 4a It is N, and connected to Y. 3a R a3 It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, Y 1a -Y 3a It is C, Y 4a It is N, and connected to Y. 2a R a2 It is a tertiary alkyl, silyl, or germanyl group.

[0448] In some implementations, at least one R b It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, at least one R b It is tert-butyl. In some implementations, at least one pair of R a A pair of R b Or an R a And an R b Connect or fused into a ring.

[0449] In some implementation schemes, R b1 Linked to C1 (carbon atom). In some such implementations, R b1 It can be selected from the generic substituents defined herein. In some such implementations, R b1 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R b1 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R b1 It is a tertiary alkyl group. In some embodiments, the tertiary alkyl group is a tertiary butyl group. In some embodiments, R... b2 It is attached to C2 (carbon atom). In some such implementations, R b2 It can be selected from the generic substituents defined herein. In some such implementations, R b2The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R b2 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R b2 It is a tertiary alkyl group. In some embodiments, the tertiary alkyl group is a tertiary butyl group. In some embodiments, R... b3 It is attached to C3 (carbon atom). In some such implementations, R b3 It can be selected from the generic substituents defined herein. In some such implementations, R b3 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R b3 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R b3 It is a tertiary alkyl group. In some embodiments, the tertiary alkyl group is a tertiary butyl group. In some embodiments, R... b4 It is attached to C4 (carbon atom). In some such implementations, R b4 It can be selected from the generic substituents defined herein. In some such implementations, R b4 The substituents can be selected from the preferred general substituents defined herein. In some such embodiments, R b4 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, R b4 It is a tertiary alkyl group. In some embodiments, the tertiary alkyl group is a tertiary butyl group.

[0450] In some embodiments, the compound has the formula Ir(L A )3, Equation Ir(L A (L) Bk )2, Equation Ir(L A )2(L Bk ), formula Ir(L A )2(L Cj-I ), formula Ir(L A )2(L Cj-II ), formula Ir(L A (L) Bk (L) Cj-I ), or the formula Ir(L A (L) Bk (L) Cj-II ), where L A As defined in this article, including L Aa-1 -(P1)(U1) (U1)(U1)(U1)(U1)(U1)toL Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126); where k is an integer from 1 to 544, and each L BkIt has the structure defined in the following List 6:

[0451] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， , , , , , , , , ， ， ， ， ， ， , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， , ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ;

[0452] Each L Cj-I With a based The structure; and each L Cj-II With a based The structure, in which about L Cj-I and L Cj-II Each L in Cj R 201 and R 202 Each is defined independently as shown in List 7 below:

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461] Where R D1 -R D246 It has the structure shown in List D:

[0462] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0463] In some embodiments, the compound is selected from those derived solely from its L... Bk Group L corresponds to those compounds that make up one of the following groups: B1 L B30 L B31 L B109 L B110 L B112 L B113 L B114 L B125 L B127 LB138 L B140 L B149 L B150 L B170 L B171 L B172 L B174 L B208 L B241 L B312 L B315 L B356 L B357 L B367 L B371 L B382 L B439 L B440 L B455 L B456 L B457 L B458 L B461 L B462 L B463 L B469 , and L B476 .

[0464] In some embodiments, the compound is selected from those derived solely from its L... Bk Group L corresponds to those compounds that make up one of the following groups: B1 L B30 L B31 L B125 L B138 L B171 L B172 L B356 L B357 L B367 L B371 L B382 L B455 , and L B456 .

[0465] In some embodiments, the compound is selected from those having their corresponding R 201 and R 202 L is defined as one of the following structures Cj-I Or L Cj-II Compounds that act as ligands: R D1 R D3 R D4 R D5 R D9 R D10 R D17 R D18 R D20 R D22 R D37 RD40 R D41 R D42 R D43 R D48 R D49 R D50 R D54 R D55 R D58 R D59 R D78 R D79 R D81 R D87 R D88 R D89 R D93 R D116 R D117 R D118 R D119 R D120 R D133 R D134 R D135 R D136 R D143 R D144 R D145 R D146 R D147 R D149 R D151 R D154 R D155 R D161 R D175 R D190 R D193 R D200 R D201 R D206 R D210 R D214 R D215 R D216 R D218 R D219 R D220 R D227 R D237 R D241 R D242 R D245 , and R D246 .

[0466] In some embodiments, the compound is selected from those having their corresponding R 201 and R 202 L is defined as one of the following structures Cj-I Or L Cj-II Compounds that act as ligands: R D1 R D3 RD4 R D5 R D9 R D10 R D17 R D22 R D43 R D50 R D78 R D116 R D118 R D133 R D134 R D135 R D136 R D143 R D144 R D145 R D146 R D149 R D151 R D154 R D155 ， R D190 R D193 R D200 R D201 R D206 R D210 R D214 R D215 R D216 R D218 R D219 R D220 R D227 R D237 R D241 R D242 R D245 , and R D246 .

[0467] In some embodiments, the compound is selected from one of the structures listed in List 8 as L Cj-I Compounds that act as ligands:

[0468] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0469] In some embodiments, the compound comprises ligand L B The ligand L B Includes a structural portion G, wherein the ligand L containing the structural portion G B The structure is selected from the following list 9:

[0470] , , , , , , , , , , , , , , , , , , ,and ,

[0471] All variables are the same as those defined above; and any two substituents may optionally be connected or fused to form a ring.

[0472] In some embodiments, the compound comprises ligand L B The ligand L B Selected from L BBk’ , where k' is an integer from 1 to 288, and the L BBk’ L is defined below (List 9a) BB1 -L BB288 :

[0473] , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ,and .

[0474] In some embodiments, the compound has the formula selected from the group consisting of: Ir(L A )3,Ir(L A )2(L B ), Ir(L A (L) B )2,Ir(L A )2(L C ), and Ir(L A (L) B (L) C In some implementations, L A Selected from the structure of List 1, List 2, List 3a, and List 3, L B Selected from List 1, List 2, List 3a, List 3, List 4, List 5, List 6 (L) Bk ), the structure of List 9 and List 9a, and L C L is selected from the definition in List 7 of this article. Cj-I and L Cj-II The structure. It should be understood that if L... A This is from list 3a, and it does not mean that it is the same as L from list 3a. B combination.

[0475] In some implementations, L A The structure is selected from List 1 and L B Selected from L Bk The structure. In some implementations, L A The structure is selected from List 2 and L B Selected from L Bk The structure. In some implementations, L A Selected from list 3 as defined in this article, and L B Selected from L Bk The structure is where k is an integer from 1 to 544. In some implementations, L A Selected from list 3 as defined in this article, and L B The structure is selected from List 9 as defined in this document. In some implementations, L A Selected from list 3a as defined in this article, and L B The structure is selected from List 9 as defined in this document. In some implementations, L A Selected from list 3a as defined in this article, and L B Selected from L BBk’ The structure is , where k' is an integer from 1 to 288. In some implementations, L ASelected from list 3 as defined in this article, and L C Selected from L Cj-I and L Cj-II The structure is , where j is an integer from 1 to 1416.

[0476] In some embodiments, the compound may have the following formula: Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))3, which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1))3 to Ir(L Aa-150 The compound composition of -(P428)(U126)(U126)(U126)(U126)(U126))3; formula Ir(L A (L) Bk )2; Equation Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))(L Bk )2, which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))(L B1 )2 to Ir(L Aa-150 -(P428)(U126)(U126)(U126) (U126)(U126))(L B544 The compound composition of )2; formula Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED ) (R EE (R) EF ))2(L B ); Formula Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))2(L Bk ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))2(L B1 ) to Ir(LAa-150 -(P428)(U126)(U126) (U126)(U126)(U126))2(L B544 The compound composition of Ir(L) Aa-n -(R EA (R) EB (R) EC ) (R ED (R) EE (R) EF ))2(L Cj-I ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))2(L C1-I ) to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126))2(L C1416-I The compound composition of Ir(L) Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))2(L Cj-II ), which is composed of Ir(L Aa-1 -(P1)(U1) (U1)(U1)(U1)(U1))2(L C1-II ) to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126) (U126))2(L C1416-II The compound composition of Ir(L) Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF )) (L Bk (L) Cj-I ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))(L B1 (L) C1-I ) to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126))(L B544 (L) C1416-I The composition of the compound is: ) or Ir(L Aa-n -(R EA (R) EB(R) EC (R) ED (R) EE (R) EF ))(L Bk (L) Cj-II ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))(L B1 (L) C1-II ) to Ir(L Aa-150 -(P428)(U126)(U126) (U126)(U126)(U126))(L B544 (L) C1416-II The compound composition of ) in which L Aa-n -(R EA (R) EB ) (R EC (R) ED (R) EE (R) EF L Bk and L Cj-I和 L Cj-II All of these are defined in this article.

[0477] In some embodiments, the compound may have the following formula: Ir(L A (L) BBk’ )2; Equation Ir(L AAg (L) BBk’ )2, which is composed of Ir(L AA1 (L) BB1 )2 to Ir(L AA216 (L) BB288 The compound composition of )2; formula Ir(L AAg )2(L B ); Formula Ir(L AAg )2(L BBk’ ), which is composed of Ir(L AA1 )2(L BB1 ) to Ir(L AA216 )2(L BB288 The compound composition of Ir(L) AAg (L) BBk’ (L) Cj-I ), which is composed of Ir(L AA1 (L) BB1 (L) C1-I ) to Ir(L AA216 (L) BB288 (L) C1416-I The composition of the compound is: ) or Ir(L AAg (L) BBk’ (L)Cj-II ), which is composed of Ir(L AA1 (L) BB1 (L) C1-II ) to Ir(L AA216 (L) BB288 (L) C1416-II The compound composition of ) in which L AAg L BBk’ and L Cj-I and L Cj-II All of these are defined in this article.

[0478] In some embodiments, the compound may have the following formula: Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))(L AAg )2, which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1) (U1))(L AA1 )2 to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126))(L AA216 The compound composition of )2; formula Ir(L Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF ))2(L AAg ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))2(L AA1 ) to Ir(L Aa-150 -(P428)(U126)(U126) (U126)(U126)(U126))2(L AA216 The compound composition of Ir(L) Aa-n -(R EA (R) EB (R) EC ) (R ED (R) EE (R) EF ))(L AAg (L) Cj-I ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1)) (LAA1 (L) C1-I ) to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126))(L AA216 ) (L C1416-I The composition of compounds, or those of the formula Ir(L) Aa-n -(R EA (R) EB (R) EC (R) ED (R) EE (R) EF )) (L AAg (L) Cj-II ), which is composed of Ir(L Aa-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1))(L AA1 (L) C1-II ) to Ir(L Aa-150 -(P428)(U126)(U126)(U126)(U126)(U126))(L AA216 (L) C1416-II The composition of the compound is as follows, where all variables are the same as those defined above.

[0479] In some embodiments, the compound is selected from the structures listed in List 10 below:

[0480] , , , , , , , , , , , , , , , , , , . , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ，， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

[0481] In some embodiments, the compound has the structure of formula IV:

[0482] Formula IV,

[0483] in:

[0484] M 1 It is either Pd or Pt;

[0485] Structural components E and F are each independently a monocyclic or polycyclic ring structure, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring;

[0486] Z 3 and Z 4 Each can be either C or N independently;

[0487] K, K 3 and K 4 Each is independently selected from the following groups: direct bonds, O, and S, wherein at least two of them are direct bonds;

[0488] L 1 L 2 and L 3Each of these groups does not exist independently, or is selected from the following groups: direct bonds, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, aryl, heteroaryl, and combinations thereof, wherein L 1 Or L 2 At least one of them exists;

[0489] R E and R F Each can independently represent zero, one, or up to the maximum allowed number of substitutions;

[0490] R, R', R E and R F Each of these groups is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and

[0491] Two adjacent R A R B R E and R F They can be connected or fused together to form a ring.

[0492] In some implementation schemes, R, R', R E and R F Each of them is independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, boroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioalkyl, and combinations thereof.

[0493] In some embodiments, structural portions E and F are each independently a monocyclic or polycyclic ring structure, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- or 6-membered carbon ring or heterocyclic ring.

[0494] In some implementations of Formula IV, at least one R A R B R E Or R F Selected from the generic substituents defined herein. In some embodiments, at least one R A Selected from the generic substituents defined herein. In some embodiments, at least one R BSelected from the generic substituents defined herein. In some embodiments, at least one R E Selected from the generic substituents defined herein. In some embodiments, at least one R F Selected from the universal substituents defined herein. In some embodiments of Formula IV, at least one R A R B R E Or R F Selected from the preferred general substituents defined in this document.

[0495] In some implementations of Formula IV, at least one R A R B R E Or R F It is partially or completely deuterated. In some implementations, at least one R A It is partially or completely deuterated. In some implementations, at least one R B It is partially or completely deuterated. In some implementations, at least one R E It is partially or completely deuterated. In some implementations, at least one R F It is partially or completely deuterated.

[0496] In some implementations of Formula IV, at least one R A It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the Pi-EWG list as defined herein.

[0497] In some implementations of Formula IV, at least one R B It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R BIt is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the Pi-EWG list as defined herein.

[0498] In some implementations of Formula IV, at least one R E It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R E It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R E It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R E It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R E It is or contains an electron-withdrawing group from the Pi-EWG list as defined herein.

[0499] In some implementations of Formula IV, at least one R F It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R F It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R F It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R F It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R F It is or contains an electron-withdrawing group from the Pi-EWG list as defined herein.

[0500] In some embodiments of Formula IV, Formula IV comprises at least one electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, Formula IV comprises at least one electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, Formula IV comprises at least one electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, Formula IV comprises at least one electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, Formula IV comprises at least one electron-withdrawing group from the Pi-EWG list as defined herein.

[0501] In some implementations, structural part E and structural part F are both 6-membered aromatic rings.

[0502] In some implementations, the structural part F is a 5- or 6-membered heteroaromatic ring.

[0503] In some implementations, L 1 It is either O or CRR'.

[0504] In some implementation schemes, Z 4 It is N and Z 3 It's C.

[0505] In some implementation schemes, Z 4 It is C and Z 3 It is N.

[0506] In some implementations, L 2 It's a direct key.

[0507] In some implementations, L 2 It is NR.

[0508] In some implementation schemes, K, K 3 and K 4 They are all direct keys.

[0509] In some implementation schemes, K, K 3 and K 4 One of them is O.

[0510] In some embodiments, structural moiety E and structural moiety F are each independently selected from benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azirabenzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, azirabenzoxazole, benzothiophene, azirabenzothiophene, benzothiazole, azirabenzothiophene, benzothiazole, azirabenzothiophene, benzothiazole, azirabenzothiophene, azirabenzothiazole ... Benzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimidazole, azabenzimidazole, benzimidazole-derived carbene, azabenzimidazole-derived carbene, benzobenzimidazole, azabenzimidazole, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

[0511] In some implementation schemes, R A R B R E Or R F At least one of them is a bulky group selected from the structure in List E below:

[0512] , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ;

[0513] Q A Q B Q C Q D and Q E Each can be used independently to indicate monosubstitution up to the maximum permissible substitution, or to indicate no substitution;

[0514] Q A Q B Q C Q D Q E Q A1 Q B1 Q C1 Q D1 and Q E1 Each of the following is independently hydrogen or a substituent selected from the group consisting of: alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof;

[0515] Y aa and Y bb Each is independently selected from the following group: direct bonds, BR, BRR', NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; and

[0516] Any two substituents can be linked or fused to form a ring.

[0517] In some embodiments, the compound is selected from compounds having the formula Pt(L A’ Compounds of (Ly):

[0518]

[0519] Where L A’ The structure selected from List 11 below:

[0520]

[0521] Where L y The structure selected from the following list 12:

[0522]

[0523]

[0524]

[0525]

[0526] in:

[0527] Structural part C is a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring;

[0528] X, X 1 and X 2 Each can be either C or N independently;

[0529] R C and R DD Each can be used independently to indicate monosubstitution up to the maximum permissible substitution, or to indicate no substitution;

[0530] Each R 1 R 2 R N R CC and R DD The substituent is independently hydrogen or selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof;

[0531] X Z and Y A Each of them independently selected from the following groups: BR e BR e Rf NR e PR e P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f , and GeR e R f ;

[0532] The remaining variables are the same as those defined previously;

[0533] Any two substituents may optionally be linked or fused to form a ring; and

[0534] R 1 R 2 R A R C Or R DD At least one of them is or contains a structure of formula III or formula IIIA, or is selected from list A1 or list A2; or the above L A’ At least one ring is fused to the structure of formula IIIB, or to the structure of list A3 described herein.

[0535] In some embodiments, structural part C may be selected from benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azabenzofuran, phenanthero[3,2-b]benzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimazole, azabenzimidazole, carbazole, azacarbazole, naphthemidazole, dibenzofuran, azadibenzofuran, dibenzothiazole, azadibenzothiazole, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

[0536] In some embodiments, the compound is selected from compounds having the formula Pt(L A’ Compounds of (Ly):

[0537]

[0538] Among them, ligand L A’ Selected from L A’a-n -(R EA (R) EB (R)EC (R) ED (R) EE (R) EF )(P), where n is an integer from 1 to 4; R EA Selected from P1-P428, R EB R EC R ED R EE and R EF Each of the integers is independently selected from U1-U126; P is an integer from 1 to 5, where for each P that is 1 to 5, L 3 It has the following meanings:

[0539]

[0540] And L A’a-1 -(P1)(U1)(U1)(U1)(U1)(U1)(U1)(1) to L A’a-4 Each of -(P428)(U126)(U126) (U126)(U126)(U126)(5) is defined in the following list 13:

[0541]

[0542] Among them, ligand L y Selected from L ym (R FA (R) FB ), where m is an integer from 1 to 4; R FA and R FB Each is independently selected from U1-U126;

[0543] Where L Y1 (U1)(U1) to L Y4 (U126)(U126) has the structure defined in the following List 14:

[0544]

[0545] in:

[0546] P1-P428 have the structure of lists A1 and A2 as defined in this document; and

[0547] U1-U126 have the structure of list C as defined in this paper.

[0548] Once again, in the above-described implementation scheme regarding the combination, R EA Selected from P1-P428, and the rest R EB R EC R ED R EE and REF Each is independently U1-U126. However, it should be understood that as long as R... EA R EB R EC R ED R EE Or R EF If at least one group is selected from P1-P428, then the remaining groups can each be independently selected from U1-U126. In some embodiments, R is specifically selected from P1-P428. EA R EB R EC R ED R EE Or R EF One of them is selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC R ED R EE Or R EF Two of the groups are selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC R ED R EE Or R EF Three of the groups are selected from P1-P428, and the remaining groups are each independently selected from U1-U126. In some embodiments, R EA R EB R EC R ED R EE Or R EF Four of the groups are selected from P1-P428, and the remaining groups are each independently selected from U1-U126. All previous combinations related to iridium may be applied equivalently or similarly, and this disclosure is intended to fully and explicitly cover them, even if they are not specifically described in this disclosure.

[0549] In some embodiments, the compound is selected from the structures listed in List 15 below:

[0550] , , , , , , , , ,and .

[0551] In some embodiments, the first ligand L having a structure comprising Formula I as described herein A The compound is partially or fully deuterated. In some embodiments, the compound is fully deuterated. In some embodiments, the first ligand L having formula I described herein... A The compound may be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, the percentage of deuteration has its conventional meaning and includes the percentage of all possible hydrogen atoms (i.e., hydrogen or deuterium positions) in the compound occupied by deuterium atoms. In some embodiments, the carbon atoms contained in the ring coordinated to metal M are partially or completely deuterated. In some embodiments, the carbon atoms contained in the polycyclic ring system coordinated to metal M are partially or completely deuterated. In some embodiments, the substituents connected to the monocyclic or fused polycyclic ring system coordinated to metal M are partially or completely deuterated.

[0552] In some implementations, the compounds of Formula I emit at room temperature with 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.

[0553] In the formula M(L) defined above A ) p (L B ) q (L C ) r In some embodiments of the heterocoordination compound, the ligand L A Having the first substituent R I The first substituent R I Having the first atom aI, in the ligand L A Of all the atoms, the first atom aI is the furthest from the metal M. Additionally, if present, the ligand L... B Having a second substituent R II The second substituent R II Having the first atom α-II, in the ligand L B Of all the atoms, the first atom a-II is the furthest from the metal M. Furthermore, if present, the ligand L... C Having a third substituent R III The third substituent R III Having the first atom α-III, in the ligand LC Of all the atoms, the first atom a-III is the furthest from the metal M.

[0554] In such heterocoordination compounds, vector V D1 V D2 and V D3 It can be defined as follows. V D1 The vector V represents the direction from metal M to the first atom aI, and the vector V represents the direction from metal M to the first atom aI. D1 Having value D 1 It represents metal M and the first substituent R. I The straight-line distance between the first atoms aI in V. D2 The vector V represents the direction from metal M to the first atom a-II, and the vector V represents the direction from metal M to the first atom a-II. D2 Having value D 2 It represents metal M and second substituent R. II The straight-line distance between the first atom a-II in V. D3 The vector V represents the direction from metal M to the first atom a-III, and the vector V represents the direction from metal M to the first atom a-III. D3 Having value D 3 It represents metal M and the third substituent R. III The straight-line distance between the first atom a-III in the matrix.

[0555] In such heterocoordination compounds, a sphere with radius r is defined, the center of which is metal M, and the radius r is such that the sphere surrounds a substituent R in the compound that is not the substituent. I R II and R III The minimum radius of all atoms in a portion; where D 1 D 2 Or D 3 At least one of them is at least 1.5 Å larger than the radius r. In some embodiments, D 1 D 2 Or D 3 At least one of them is at least 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6, or 19.1 Å larger than the radius r. In some embodiments, D 1 D 2 Or D 3 At least two of them are at least 1.5, 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6 or 19.1 Å larger than the radius r.

[0556] In some embodiments of such heterocoordination compounds, the compound has a transition dipole moment axis, and the transition dipole moment axis and the vector VD1 V D2 and V D3 The angle is defined, wherein the transition dipole moment axis and the vector V are defined. D1 V D2 and V D3 At least one of the angles between them is less than 40°. In some embodiments, the transition dipole moment axis and the vector V D1 V D2 and V D3 At least one of the angles between them is less than 30°, 20°, 15°, or 10°. In some embodiments, the transition dipole moment axis and the vector V D1 V D2 and V D3 At least two of the angles between them are less than 20°. In some embodiments, the transition dipole moment axis and the vector V D1 V D2 and V D3 At least two of the angles between them are less than 15° or 10°.

[0557] In some implementations, the transition dipole moment axis and the vector V D1 V D2 and V D3 All three angles between them are less than 20°. In some embodiments, the transition dipole moment axis and the vector V D1 V D2 and V D3 All three angles between them are less than 15° or 10°.

[0558] In some embodiments of such heterocoordination compounds, the compound has a vertical dipole ratio (VDR) of 0.33 or less. In some embodiments of such heterocoordination compounds, the compound has a VDR of 0.30, 0.25, 0.20, 0.15 or less.

[0559] Those skilled in the art will readily understand the meaning of the terms "transition dipole moment axis" and "vertical dipole ratio" of a compound. However, the meanings of these terms can be found in U.S. Patent No. 10,672,997, the disclosure of which is incorporated herein by reference in its entirety. In U.S. Patent No. 10,672,997, the horizontal dipole ratio (HDR) of the compound is discussed, not the VDR. However, those skilled in the art will readily understand that VDR = 1 - HDR.

[0560] In some embodiments, the compound may be an emission dopant. In some embodiments, the compound may generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence, triplet-triplet annihilation, or a combination of these methods. In some embodiments, the emission dopant may be a racemic mixture or may be enriched with one enantiomer. In some embodiments, the compounds of the present invention may 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 may be homogamic (each ligand is identical). In some embodiments, the compound may be heterogamic (at least one ligand is different from the others). In some embodiments, when more than one ligand coordinated to a metal is present, the ligands may all be identical. In some other embodiments, at least one ligand is different from the others. In some embodiments, each ligand may be different from all the others. This also applies in embodiments where ligands coordinated to a metal may be linked to other ligands coordinated to the metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Therefore, in some embodiments where the ligands are linked together, all the ligands may be the same, and in some other embodiments, at least one of the linked ligands may be different from the others.

[0561] In another aspect of this disclosure, compositions comprising the novel compounds disclosed herein are described. The compositions may include one or more components selected from the group consisting of solvents, emitters, hosts, hole injection materials, hole transport materials, electron blocking materials, and electron transport materials.

[0562] This disclosure covers any chemical structure comprising novel compounds, whether in their neutral molecular form, monovalent or polyvalent form, monomeric or polymeric form, or macromolecular or supramolecular form, wherein said compound has the first ligand L described herein. A In another aspect, this disclosure also provides compositions of compounds of formula I, wherein the compounds of formula I comprise a neutral molecular form, or a monovalent or polyvalent form thereof, or a monomeric or polymeric form thereof, or a macromolecular or supramolecular form thereof, and wherein the compounds have a first ligand L as described herein. AAs used herein, a "monovalent variant of a compound" refers to the same structural moiety as the compound, but in which one hydrogen atom has been removed and replaced with a bond to the rest of the chemical structure. A "multivalent variant of a compound" refers to the same structural moiety as the compound, but in which multiple hydrogen atoms have been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecular structures, the compounds of the present invention can also be incorporated into supramolecular complexes without covalent bonds. When used in the context, the description of structure A containing structural moiety B means that structure A includes the structure of structural moiety B, but does not include H or D atoms that can be attached to structural moiety B. This is because at least one H or D atom on the structure of a given structural moiety must be replaced to become a substituent, such that structural moiety B can be part of structure A, and after it becomes part of structure A, one or more H or D atoms on the structure of a given structural moiety B can be further substituted.

[0563] C. OLEDs and Devices of this Disclosure

[0564] In another aspect, this disclosure also provides an OLED device comprising a first organic layer containing compounds as disclosed in the foregoing compound section of this disclosure.

[0565] 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 comprises an organic layer having a first ligand L as described herein. A Compounds.

[0566] In some embodiments, the organic layer is selected from the group consisting of HIL, HTL, EBL, EML, HBL, ETL, and EIL. In some embodiments, the organic layer may be an emission layer, and the compounds described herein may be emission dopants or non-emission dopants. In some embodiments, the emission layer may also optionally contain a dopant selected from delayed fluorescence dopants and non-delayed fluorescence dopants.

[0567] In some embodiments, the organic layer may further comprise a body containing at least one chemical group selected from the group consisting of: benzo[9,10]phenanthrene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2-Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronanaphtho[3,2,1-de]anthracene, azircyclohexane, oxacyclohexane, dihydroacridine, xanthonium, dihydrobenzoaziroxane, dibenzooxane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borylalkyl, silylalkyl, azirbenzo[9,10]phenanthrene, azircarbazole, azirindolocarbazole, azirdibenzothiophene, azirdibenzofuran, azirdibenzoselenophene, azir-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo and aza-(5,9-dioxa-13b-boronanaphtho[3,2,1-de]anthracene).

[0568] In some implementations, the subject may be selected from the structure of subject group 1:

[0569] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0570] in:

[0571] Each of J1 to J6 is independently either C or N;

[0572] L' is a direct bond or an organic linking group;

[0573] Y AA Y BB Y CC and Y DD Each is independently selected from the following groups: void, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0574] R A' R B' R C' R D' R E' R F' and R G' Each of the terms in the alphabet independently represents a single substitution up to the maximum permissible substitution, or represents no substitution.

[0575] Each R, R', RA' R B' R C' R D' R E' R F' and R G' Substituents that are independently hydrogen or selected from the generic substituents defined herein; any two substituents may be linked or fused to form a ring;

[0576] Furthermore, where possible, each unsubstituted aromatic carbon atom can be replaced by one or more N atoms to form a nitrogen-substituted ring.

[0577] In some embodiments, L' is an organic linking group selected from the group consisting of: BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, aryl, heteroaryl, and combinations thereof.

[0578] 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 It is independently O, S, or SiRR', or more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen heterocycle.

[0579] In some implementations, the subject 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:

[0580] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

[0581] The structural diagrams of MG1 through MG27 are shown below:

[0582] , , , , , , , , , , , , , , , , , , , , , , , , , , .

[0583] 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.

[0584] In some embodiments, the body may be any of its nitrogen-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the body has the formula EGa-MGb-EGc and is selected from h1 to h112 as defined in the following list of body group 2, wherein each of MGb, EGa, and EGc is defined as follows:

[0585]

[0586] 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 marked with a numerical prefix to identify their bonding position in the MGb structure.

[0587] In some embodiments, the organic layer may further comprise a host, wherein the host comprises a metal complex.

[0588] In some embodiments, the emitter layer may comprise two substrates: a first substrate and a second substrate. In some embodiments, the first substrate is a hole transport substrate, and the second substrate is an electron transport substrate. In some embodiments, the first substrate is a hole transport substrate, and the second substrate is a bipolar substrate. In some embodiments, the first substrate and the second substrate may form an excimer complex. In some embodiments, the emitter layer may comprise a third substrate. In some embodiments, the third substrate is selected from the group consisting of an insulating substrate (wide bandgap substrate), a hole transport substrate, and an electron transport substrate. In some embodiments, the third substrate forms an excimer complex with one of the first substrate and the second substrate, or with both of the first substrate and the second substrate. In some embodiments, the emitter layer may comprise a fourth substrate. In some embodiments, the fourth substrate is selected from the group consisting of an insulating substrate (wide bandgap substrate), a hole transport substrate, and an electron transport substrate. In some embodiments, the fourth substrate forms an excimer complex with one of the first substrate, the second substrate, and the third substrate, with two of the first substrate, the second substrate, and the third substrate, or with each of the first substrate, the second substrate, and the third substrate. In some implementations, the LUMO of the electron transport 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 implementations, the HOMO of the hole transport host is greater than -5.6 eV, greater than -5.5 eV, greater than -5.4 eV, or greater than -5.35 eV. HOMO and LUMO values ​​can be determined using solution electrochemistry. Solution cyclic voltammetry and differential pulse voltammetry can be performed using a CH Instrument 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. The electrochemical potential can be referenced to the internal ferrocene-ferrocene redox pair (Fc / Fc+) by measuring the peak potential difference using differential pulse voltammetry.According to the literature ((a) Fink, R.; Heischkel, Y.; Thelakkat, M.; Schmidt, H.-W., Chem. Mater. 1998, 10, 3620-3625; (b) Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, RF; Bassler, H.; Porsch, M.; Daub, Journal of Advanced Materials 1995, 7, 551), by comparing the redox potentials of the cations and anions with a ferrocene reference (4.8). The corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were determined by measuring the energy of the HOMO (highest occupied molecular orbital) relative to vacuum (eV).

[0589] In some embodiments, the compound described herein may be a sensitizer or a component of a sensitizer; wherein the device may further include a receptor that receives energy from the sensitizer. In some embodiments, the receptor is an emitter in the device. In some embodiments, the receptor may be a fluorescent material. In some embodiments, the compound described herein may be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain receptors in the form of one or more non-delayed fluorescent and / or delayed fluorescent materials. In some embodiments, the compound described herein may be used as a component of an excimer complex used as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the receptor and the receptor to emit energy or further transfer energy to the final emitter. The receptor concentration may range from 0.001% to 99.9%. The receptor may be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the receptor is a thermally activated delayed fluorescence (TADF) material. In some embodiments, the receptor is a non-delayed fluorescent material. In some embodiments, emission may be generated by any one or all of the sensitizer, receptor, and final emitter. In some implementations, the receptor emits at room temperature with 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.

[0590] As used herein, phosphorescence generally refers to photon emission with a change in electron spin quantum number, i.e., the initial and final states of emission have different electron spin quantum numbers, such as from T1 to S0. Most Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, such exciton complexes can also emit phosphorescence if exciton complex formation involves a triplet emitter. On the other hand, fluorescence emission generally refers to photon emission with a constant electron spin quantum number, such as from S1 to S0 or from D1 to D0. Fluorescent emitters can be delayed or non-delayed fluorescent emitters. Depending on the spin state, fluorescent emitters can be singlet, doublet, or other multiplyt emitters. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Two types of delayed fluorescence exist: 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 depend on the collision of two triplet states, but rather on the thermal population between the triplet and singlet excited states. Thermal energy can activate the triplet state to transition back to the singlet state. This type of delayed fluorescence is also known as TADF. E-type delayed fluorescence characteristics can be seen in excimer complex systems or single compounds. Unbound by theory, it is believed that TADF emission requires a small singlet-triplet bandgap (ΔE) less than or equal to 400, 350, 300, 250, 200, 150, 100, or 50 meV. S-T The electron transport compound or excitokinetic complex is a compound that emits electrons. There are two main types of TADF emitters: one called donor-acceptor TADF and the other called multi-resonant (MR) TADF. Typically, a single-compound donor-acceptor TADF compound is constructed by connecting the electron donor structural part (such as an amino or carbazole derivative) and the electron acceptor structural part (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). Donor-acceptor excitokinetic complexes can be formed between hole-transporting compounds and electron-transporting compounds. Examples of MR-TADF materials include highly conjugated fused-ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials may also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 for delayed fluorescence emission at 293 K is less than or equal to 10 microseconds. In some embodiments, such a time can be greater than 10 microseconds and less than 100 microseconds.

[0591] In some embodiments, the OLED may include additional compounds selected from the group consisting of non-delayed fluorescent materials, delayed fluorescent materials, phosphorescent materials, and combinations thereof.

[0592] In some embodiments, the compounds of the present invention described herein are phosphorescent materials.

[0593] 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 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 an acceptor. In some embodiments, the phosphorescent material forms an excimer complex with another material within the OLED (e.g., a host material, an emitter material).

[0594] 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 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 an acceptor, and the OLED further includes a sensitizer.

[0595] In some embodiments of OLEDs, 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-metallic complex. In some embodiments, the delayed fluorescence 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 fluorescence material comprises a metal-carbene bond. In some embodiments, the non-delayed fluorescence material or the delayed fluorescence material comprises at least one chemical group selected from the group consisting of: arylamine, aryloxy, arylthio, benzo[9,10]phenanthrene, carbazole, indolecarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene, 5λ λ diaza Boron-naphthalene Anthracene Oxygen λ 2-aza-13b-boronanaphthene, azacyclohexylborane, oxacyclohexylborane, dihydroacridine, xanthones, dihydrobenzoazasiloxane, dibenzooxazine, phenoxthiazine, phenthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, amino, silane, their aza variants and combinations thereof. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material comprises tri(aryl / heteroaryl)borane, wherein one or more pairs of substituents from the aryl / heteroaryl group are bonded to form a ring. In some embodiments, the fluorescent material comprises at least one chemical group selected from the group consisting of naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-, perylene, and azulene.

[0596] In another aspect, the OLED of this disclosure may also include an emission region containing a compound or a combination of compounds disclosed in the foregoing compound section of this disclosure. In some embodiments, the emission region may include a first ligand L as described herein. A The emission region comprises one or more organic layers, at least one of which has a minimum thickness selected from the group consisting of 350, 400, 450, 500, 550, 600, 650, and 700 Å. In some embodiments, at least one of the organic layers is formed by an emission system with a figure of merit (FOM) equal to or greater than 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 is available in U.S. Patent Application Publication No. 2023 / 0292605, the entire contents of which are incorporated herein by reference. In some embodiments, at least one of the organic layers comprises a compound or composition of compounds disclosed in Parts A and D of this disclosure.

[0597] In some embodiments, the OLED or emitting region containing the compound of the present invention disclosed herein may be incorporated into a full-color pixel arrangement of a device. Such a full-color pixel arrangement of a device includes at least one pixel, wherein said at least one pixel includes a first sub-pixel and a second sub-pixel. The first sub-pixel includes a first OLED containing a first emitting region. The second sub-pixel includes a second OLED containing a second emitting region. In some embodiments, the first and / or second OLEDs, the first and / or second emitting regions may be the same or different and may each independently have various device features and various embodiments of the compound of the present invention included therein, as well as various combinations and sub-combinations of various device features and various embodiments of the compound of the present invention included therein, as disclosed herein.

[0598] In some implementations, the first emission region is configured to emit light with a peak wavelength λ. max1 The second emission region is configured to emit light with a peak wavelength λ. max2 The light. In some implementations, the peak wavelength λ max1 With λ max2 The difference between them is at least 4 nm but within the same color. For example, light blue and dark blue light as described above. In some embodiments, the first emission region is configured to emit light with a peak wavelength λ in one region of the visible spectrum at 400-500 nm, 500-600 nm, or 600-700 nm. max1 The second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum: 400-500 nm, 500-600 nm, or 600-700 nm. max2 The light emitted is emitted. In some embodiments, the first emitting region comprises a first number of emitting layers (deposited in stacks if there are more than one layer); and the second emitting region comprises a second number of emitting layers (deposited in stacks if there are more than one layer); and the first number is different from the second number. In some embodiments, both the first and second emitting regions comprise phosphorescent materials, which may be the same or different. In some embodiments, the first emitting region comprises phosphorescent materials, while the second emitting region comprises fluorescent materials. In some embodiments, both the first and second emitting regions comprise fluorescent materials, which may be the same or different.

[0599] In some embodiments, at least one pixel of an OLED or emitting region comprises a total of N sub-pixels, wherein the N sub-pixels include a first sub-pixel and a second sub-pixel; each of the N sub-pixels contains an emitting region; and the total number of emitting regions within the at least one pixel is equal to or less than N-1. In some embodiments, the second emitting region is identical to the first emitting region, and each sub-pixel of the at least one pixel contains the same emitting region as the first emitting region. In some embodiments, a full-color pixel arrangement may have multiple pixels containing a first pixel region and a second pixel region, wherein at least one display feature in the first pixel region differs from a corresponding display feature in the second pixel region, and wherein the at least one display feature is selected from the group consisting of: resolution, cavity mode, color, output coupling, and color filter.

[0600] In some embodiments, the OLED is a stacked OLED comprising one or more charge generating layers (CGLs). In some embodiments, the OLED comprises a first electrode, a first emitting region disposed above the first electrode, a first CGL disposed above the first emitting region, a second emitting region disposed above the first CGL, and a second electrode disposed above the second emitting region. In some embodiments, the first emitting region and / or the second emitting region may have various device features as described above for pixelated devices. In some embodiments, the stacked OLED is configured to emit white. In some embodiments, one or more of the emitting regions in the pixelated OLED or stacked OLED comprise a sensitizer and an acceptor having various sensitized device features and various embodiments of the compounds of the present invention disclosed herein. For example, the first emitting region is included in the sensitized device while the second emitting region is not included in the sensitized device; in some cases, both the first and second emitting regions are included in the sensitized device.

[0601] In some embodiments, the light emitted by the OLED may be at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99%, or 100% derived from plasmonic modes. In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emitting layer serves as a reinforcement layer. The reinforcement layer comprises a plasmonic material exhibiting surface plasmon resonance, which is nonradiatively coupled to the emitter material and transfers excited-state energy from the emitter material to the nonradiative modes of surface plasmon polaritons. In some embodiments, the reinforcement layer is positioned at a distance from the organic emitting layer not exceeding a threshold distance, wherein, due to the presence of the reinforcement layer, the emitter material has a total nonradiative decay rate constant and a total radiative decay rate constant. The threshold distance is the position where the total nonradiative decay rate constant equals 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 nonradiative decay rate constant and the total radiative decay rate constant equals the photoluminescence yield of the emitting material without the reinforcement layer.

[0602] In some embodiments, the OLED further includes an output coupling layer. In some embodiments, the output coupling layer is disposed above the enhancement layer on the side opposite the organic emitting layer. The output coupling layer scatters energy from surface plasmon polaritons. In some embodiments, this energy is scattered as photons into free space. In other embodiments, energy is scattered from the surface plasmon polariton modes 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 intermediary layers may be disposed between the enhancement layer and the output coupling layer. Examples of the intermediary layers may be dielectric materials, including organic, inorganic, perovskite, and oxide materials, and may comprise stacks and / or mixtures of these materials.

[0603] The enhancement layer alters the effective properties of the medium in which the emitter material resides, resulting in any or all of the following: reduced emissivity, altered emission line shape, emission intensity variation with angle, altered emitter material stability, altered OLED efficiency, and reduced OLED device efficiency roll-off. Placing the enhancement layer on the cathode side, anode side, or both sides, or having the enhancement layer itself as a CGL, produces an OLED device utilizing any of the aforementioned effects. In addition to the specific functional layers described herein and in the various OLED examples shown in the accompanying drawings, the OLEDs of this disclosure may also include any other functional layers commonly found in OLEDs.

[0604] In some embodiments, the reinforcing layer may be composed of a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may include at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the reinforcing layer is configured as a planar layer. In other embodiments, the reinforcing layer is characterized by a periodically, quasi-periodically, or randomly arranged wavelength size, or by a periodically, quasi-periodically, or randomly arranged subwavelength size.

[0605] In some embodiments, the output coupling layer has a wavelength or subwavelength characteristic of being arranged periodically, quasi-periodically, or randomly. In some embodiments, the output coupling layer may be composed of multiple nanoparticles. In some embodiments, the output coupling layer is composed of multiple nanoparticles disposed on a material. In these embodiments, the output coupling layer can be adjusted by at least one of the following: changing the size of the multiple nanoparticles, changing the shape of the multiple nanoparticles, changing the material of the multiple nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the multiple nanoparticles, changing the thickness of the reinforcement layer, or changing the material of the reinforcement layer. The multiple nanoparticles of the device may be formed from at least one of the following materials: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stacks or laminates of one or more materials and / or a core of one type of material and a shell of a different type of material coated thereon. In some embodiments, the output coupling layer comprises at least metal nanoparticles, wherein the metal is selected from the group consisting of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the output coupling layer is formed by photolithography.

[0606] In some embodiments of plasmonic devices, the emitter and / or host compound used in the emitter 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.

[0607] In another aspect, this disclosure also provides consumer products comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise compounds or compositions of compounds disclosed in the foregoing compound section of this disclosure.

[0608] In some embodiments, the consumer product includes an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer may contain a first ligand L as described herein. A Compounds.

[0609] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to both the anode and cathode. When a current is applied, holes are injected into the anode and electrons into the organic layer from the cathode. The injected holes and electrons migrate toward their respective oppositely charged electrodes. When electrons and holes are localized on the same molecule, "excitons" are formed, which are localized electron-hole pairs with excited energy states. Light is emitted when the excitons relax via photoemission mechanisms. In some cases, excitons can be localized as excimers or excitokines. Non-radiative mechanisms such as thermal relaxation may also occur, but are generally considered undesirable.

[0610] Figure 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer (HIL) 120, a hole transport layer (HTL) 125, an electron closure layer (EBL) 130, an emission layer (EML) 135, a hole closure 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. The 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, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704, which is incorporated herein by reference.

[0611] More examples are available for each of these layers. For example, a flexible 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-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1 (m-MTDATA:F4-TCNQ), as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of luminescent and host materials are disclosed in U.S. Patent No. 6,303,238 (Thompson et al.), which is incorporated herein by reference in its entirety. An example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, including composite cathodes having a thin metal layer such as Mg:Ag and a covering transparent, conductive sputter-deposited ITO layer, are disclosed herein by reference in their entirety. Theories and uses of sealing layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, both of which are incorporated herein by reference in their entirety. Examples of implanted layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0612] Figure 2 An inverted OLED 200 is shown. The device includes a substrate 210, a cathode 215, an emitter layer 220, a hole transport layer 225, and an anode 230. Device 200 can be fabricated by depositing the layers sequentially. Because the most common OLED configuration has a cathode disposed above the anode, and device 200 has a cathode 215 disposed below the anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described when discussing device 100 can be used in the corresponding layers of device 200. Figure 2 An example of how to omit some layers from the structure of device 100 is provided.

[0613] The simple layered structures shown in Figures 1 and 2 are provided as non-limiting examples, and it should be understood that embodiments of this disclosure can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the various layers described in different ways, or the layers can be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many examples provided herein describe various layers as comprising a single material, it should be understood that combinations of materials, such as mixtures of host and dopant, or more generally, mixtures, may be used. Furthermore, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emitter layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, regarding Figure 1 and 2 Multiple layers of the different organic materials mentioned above.

[0614] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) composed of polymeric materials, as disclosed in, for example, U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. As another example, an OLED with a single organic layer can be used. OLEDs can be stacked, for example as described in, for example, U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. OLED structures can be deviated from... Figure 1 and 2 The illustrations depict a simple layered structure. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the benchtop structure described in U.S. Patent No. 6,091,195 to Forrest et al. and / or the pit structure described in U.S. Patent No. 5,834,893 to Bulovic et al., all of which are incorporated herein by reference in their entirety.

[0615] Unless otherwise stated, any of these layers in the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet printing (e.g., described in U.S. Patent Nos. 6,013,982 and 6,087,196, the entire contents of which are incorporated herein by reference), organic vapor deposition (OVPD) (e.g., described in U.S. Patent No. 6,337,102 to Forrest et al., the entire contents of which are incorporated herein by reference), and deposition by organic vapor jet printing (OVJP, also known as organic vapor jet deposition (OVJD)) (e.g., described in U.S. Patent No. 7,431,968, the entire contents of which are incorporated herein by reference). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably performed under a nitrogen or 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 via masks, photolithography, and cold soldering (e.g., methods described in U.S. Patent Nos. 6,294,398 and 6,468,819, the entire contents of which are incorporated herein by reference), and patterning in conjunction with certain deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The deposited material can be modified to make it compatible with the specific deposition method. For example, substituents such as branched or unbranched alkyl and aryl groups (preferably containing at least 3 carbon atoms) can be used in small molecules to improve their ability to undergo solution processing. Substituents having 20 or more carbon atoms can be used, and 3-20 carbon atoms are a preferred range. Materials with asymmetric structures can have better solution processability than those with symmetric structures because asymmetric materials can have a lower tendency to recrystallize. Dendritic molecular substituents can be used to improve the ability of small molecules to undergo solution processing.

[0616] Devices manufactured according to some embodiments of this disclosure may optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from harmful exposure to environmental substances, including moisture, vapors, and / or gases. The barrier layer may be deposited above, below, adjacent to, or over any other portion of the device, including edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed using a variety of known chemical vapor deposition techniques and may comprise 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 comprise an inorganic compound or an organic compound or both. Preferred barrier layers comprise multiple alternating layers of polymeric and non-polymeric materials, multiple alternating layers of organic and inorganic materials, or mixtures of polymeric 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, the entire contents of which are incorporated herein by reference.

[0617] Devices manufactured according to embodiments of this disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be integrated into various electronic products or intermediate components. Examples of such electronic products or intermediate components include displays, lighting devices such as discrete light source devices, or lighting panels that can be utilized by end-user product manufacturers. Such electronic component modules may optionally include driving electronics and / or power supplies. Devices manufactured according to embodiments of this disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. This invention discloses a consumer product comprising an OLED, wherein the OLED comprises compounds of this disclosure in its organic layer. Such consumer products include any kind of product containing one or more light sources and / or one or more of some type of visual display. Examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, phototherapy devices, and signage. Various control mechanisms can be used to control devices manufactured according to this disclosure, including passive and active matrices. Many of the devices are intended for use within a temperature range comfortable for humans, such as 18°C ​​to 30°C, more preferably at room temperature (20-25°C), but can be used outside this temperature range (e.g., -40°C to +80°C).

[0618] Further details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, the entire contents of which are incorporated herein by reference.

[0619] 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 utilize the materials and structures described. More generally, organic devices such as organic transistors can utilize the materials and structures described.

[0620] In some embodiments, the OLED has one or more features selected from the group consisting of: being flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer including carbon nanotubes. In some embodiments, the OLED further comprises one or more quantum dots. Such quantum dots may be in the emitter layer or in other functional layers such as the conversion layer.

[0621] In some embodiments, the OLED comprises an RGB pixel arrangement or a white pixel arrangement with a color filter. 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 of less than 10 inches or an area of ​​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.

[0622] D. Other materials used in OLEDs

[0623] The materials described herein are various examples of materials that can be used in specific layers in OLEDs. They can also be used in combination with a wide variety of other materials present in the device. For example, the emission dopants disclosed herein can be used by the emission dopants in the EML themselves, or in combination with a wide variety of other emitters, bodies, transport layers, capping layers, implantation 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 readily consult the literature to identify other materials that can be used in combination.

[0624] a) Conductive dopants:

[0625] Charge transport layers can be doped with conductive dopants to substantially alter their charge carrier density, which in turn changes their conductivity. Conductivity can be increased by generating charge carriers in the matrix material, and, depending on the type of dopant, variations in the Fermi level of the semiconductor can also be achieved. Hole transport layers can be doped with p-type conductive dopants, and n-type conductive dopants are used in electron transport layers. In some embodiments, the conductive dopant comprises at least one chemical structural moiety selected from the group consisting of cyano, fluorinated aryl or heteroaryl, fluorinated alkyl or cycloalkyl, alkylene, heteroaryl, amide, benzodithiophene, and highly conjugated heteroaryl groups extended by acyclic double bonds.

[0626] b) HIL / HTL:

[0627] The hole injection / transport materials used in this disclosure are not particularly limited, and any compound may be used, provided that the compound is commonly used as a hole injection / transport material. Examples of materials include, but are not limited to, phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indole-carbazole derivatives; polymers containing fluorinated hydrocarbons; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; and metal oxide derivatives such as MoO. x p-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylhexacarbonitrile; metal complexes; and crosslinkable compounds.

[0628] Examples of aromatic amine derivatives used for HIL or HTL include, but are not limited to, the following general formula structures:

[0629] , , , ,and .

[0630] Ar 1 To Ar 9 Each of these is selected from the group consisting of: aromatic cyclic compounds, such as benzene, biphenyl, biphenyl, benzo[9,10]phenanthrene, naphthalene, anthracene, fen, phenanthrene, fluorene, pyrene, β, perylene, and azulene; aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole-carbazole, pyridylindole, pyrrolo-dipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benzo[9,10]phenanthrene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, oxazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benzo[9,10]phenanthrene, ... Isoxazole, benzothiazole, quinoline, isoquinoline, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, phenotoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenopyridine, and selenopyridine; and a group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. 1 To Ar 9 Each of them can be unsubstituted or can be substituted by the general substituents described above, and any two substituents can be linked or fused into a ring.

[0631] In some implementations, each Ar 1 To Ar9 Independently includes structural parts selected from the following group:

[0632] , , , , , ,and ;

[0633] Where k is an integer from 1 to 20; X 101 To X 108 It is C or N; Z 101 It is C, N, O, or S.

[0634] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0635] Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 The coordinating atoms are independently selected from C, N, O, P, and S; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k" is the maximum number of ligands that can be bound to the metal.

[0636] In some implementation schemes, (Y 101 -Y 102 (Y) is a 2-phenylpyridine or 2-phenylimidazole derivative. In some embodiments, (Y) 101 -Y 102 Met is a carbene ligand. In some embodiments, Met is selected from Ir, Pt, Pd, Os, Cu, and Zn. In some embodiments, the metal complex has a relative affinity to Fc. + The minimum oxidation potential in solution with / Fc coupling is less than about 0.6V.

[0637] In some embodiments, the HIL / HTL material is selected from the group consisting of phthalocyanine and porphyrin compounds, starburst triarylamine, and CF. xFluorinated hydrocarbon 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 (e.g., molybdenum oxide and tungsten oxide), n-type semiconductive organic complexes, organometallic complexes, crosslinkable compounds, polythiophene-based polymers and copolymers, triarylamines, triarylamines containing spirofluorene cores, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indole-carbazole, isoindole compounds, and metal carbene complexes.

[0638] c) EBL:

[0639] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emitter layer. The presence of such a blocking layer in a device can lead to significantly higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, the 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 a higher triplet energy compared to one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO level of the compound used in the EBL is shallower than the HOMO levels of one or more of the hosts in the EML. In some embodiments, the compound used in the EBL contains the same molecules or functional groups as those used in one of the hosts described below.

[0640] d) Main body:

[0641] The light-emitting layer of the organic EL device disclosed herein 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.

[0642] Examples of metal complexes used as the host preferably have the following general formula:

[0643]

[0644] Where Met is a metal; (Y) 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 The coordinating atoms are independently selected from C, N, O, P, and S; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k" is the maximum number of ligands that can be bound to the metal.

[0645] In some implementations, the metal complex is:

[0646]

[0647] (ON) is a bidentate ligand that coordinates the metal with O and N atoms.

[0648] In some implementations, Met is selected from Ir and Pt. In another implementation, (Y 103 -Y 104 ) is a carbene ligand.

[0649] In some embodiments, the host compound contains at least one group selected from the group consisting of: aromatic cyclic compounds, such as benzene, biphenyl, biphenyl, benzo[9,10]phenanthrene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-phenanthrene, perylene, and azurite; aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, and oxadiazole. Azole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziisoxazole, benzothiazazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, phenothiazine, azidobenzothiophene, azidobenzofuran, azidobenzoselenophene, azidocarbazole, azidoindolocarbazole, azidobenzo[9,10]phenanthrene, azidotetrophene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronanaphene[3,2,1-de]anthracene; and a group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. Each option within the group may be unsubstituted or may be substituted by the general substituents described herein or may be further fused.

[0650] In some embodiments, the host compound comprises at least one structural moiety selected from the group consisting of:

[0651] , , , , , , , , , , , , , , , , , , , ,and ,

[0652] Where K is an integer between 0 and 20 or between 1 and 20; X 101 -X 108 Independently selected from C or N; Z 101 and Z 102 It can be independently selected from C, N, O, or S.

[0653] In some embodiments, the host material is selected from the group consisting of: arylcarbazole, metal 8-hydroxyquinoline compounds (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic fused rings, zinc complexes, β-based compounds, arylbenzo[9,10]phenanthrene compounds, polyfused heteroaryl compounds, donor-acceptor molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., pvk), spirofluorene compounds, and spirofluorene. -Carbazole compounds, indolocarbazole, 5-membered electron-deficient heterocycles (e.g., triazoles, oxadiazoles), tetrabenzene 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, non-conjugated carbazoles, azacarbazole / dibenzofuran / dibenzothiophene compounds, and high triplet state organometallic complexes (e.g., metal carbene complexes).

[0654] e) Emitter material in EML:

[0655] One or more emitter materials may be used in conjunction with the compounds or devices disclosed herein. In the present devices described herein, the emitter material may be either emissive or non-emissive. Examples of emitter materials are not particularly limited, and any compound may be used as long as it is capable of generating emission in a conventional OLED device. Examples of suitable emitter materials include, but are not limited to, compounds capable of generating 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 combinations thereof.

[0656] In some implementations, the emitter material has the formula M(L)1 ) x (L 2 ) y (L 3 ) z ;

[0657] Where L 1 L 2 and L 3 They can be the same or different;

[0658] Where x is 1, 2, or 3;

[0659] Where y is 0, 1, or 2;

[0660] Where z is 0, 1, or 2;

[0661] Where x+y+z is the oxidation state of metal M;

[0662] Where L 1 Structures selected from the following list of ligands:

[0663] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ;

[0664] Where L 2 and L 3 Each person independently selects from the following groups: and the structures in the ligand list; where:

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

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

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

[0668] Y 1 -Y 15 Each is independently selected from the following groups: C and N;

[0669] Y Selected from the following group: BR e NR e PR e ,O,S,Se,C=O,S=O,SO2,CR e R f SiR e R f and GeR e R f ;

[0670] Each R a R b R c and R d It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0671] Each R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Independently, it is either hydrogen or a substituent selected from the generic substituents defined herein; and

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

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

[0674] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0675] in

[0676] X 96 To X 99 Each of them is independently C or N;

[0677] Each Y 100 Independently selected from NR , O, S and Se;

[0678] R 10a R 20a R 30a R 40a and R 50a Each of the terms in the alphabet independently represents monosubstituted to maximally substituted, or represents no substitution.

[0679] R, R R R 10a R 11a R 12a R 13a R 20a R 30a R 40aR 50a R 60 R 70 R 97 R 98 and R 99 Each of the substituents is independently hydrogen or a substituent selected from the generic substituents defined herein; any two substituents may be linked or fused to form a ring.

[0680] In some embodiments, the emitter material is selected from the following dopant group 2:

[0681] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ,

[0682] in:

[0683] Each Y 100 Independently selected from NR , O, S and Se;

[0684] L is independently selected from the following group: 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;

[0685] X 100 and X 200 Each time it appears, select from the following group: O, S, Se, NR and CR R ;

[0686] Each R A" R B" RC" R D" R E" and R F" Independently indicates monosubstituted to maximally substituted, or indicates no substitution;

[0687] R, R R R R A1' R A2' R A" R B" R C" R D" R E" R F" R G" R H" R I" R J" R K" R L" R M" and R N" Each of the substituents is independently hydrogen or a substituent selected from the generic substituents defined herein; and any two substituents may be linked or fused to form a ring.

[0688] In some embodiments of dopant groups 1 and 2 above, each unsubstituted aromatic carbon atom may be replaced by N to form a nitrogen heterocycle. In some embodiments, the maximum number of N atoms in a ring is 1 or 2. In some embodiments of dopant group 2 above, each Pt atom in the formula may be replaced by a Pd atom.

[0689] In some embodiments of OLEDs, 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-metallic complex. In some embodiments, the delayed fluorescence material is a Zn, Cu, Ag, or Au complex.

[0690] In some implementations of OLEDs, delayed fluorescence materials have the formula M(L 5 (L) 6 ), where M is Cu, Ag, or Au, L 5 and L 6 Different, and L 5 and L 6 Select independently from the following groups:

[0691] , , , ¸ , , , , , , , , , , , , , , , , , , , , ,and ;

[0692] in,

[0693] A 1 -A 9 Each is independently selected from C or N;

[0694] Each R P R Q and R U Independently indicates monosubstitution up to maximal substitution, or indicates no substitution;

[0695] Each R P R P R U R SA R SB R RA R RB R RC R RD R RE and R RF It is hydrogen alone, or a substituent selected from the generic substituents defined herein; any two substituents may be linked or fused to form a ring.

[0696] In some embodiments of OLEDs, the delayed fluorescence material comprises at least one donor structure portion selected from the group consisting of:

[0697] , , , , , , , , , , , , , , , , , , , ,and ,

[0698] Where Y T Y U Y V and Y W Each of the following groups is selected independently: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2.

[0699] In some of the above embodiments, any carbon ring atom in each phenyl ring of any of the above structures, up to a total of three carbon ring atoms, together with their substituents, may be replaced by N.

[0700] In some embodiments, the delayed fluorescence material comprises at least one acceptor structural moiety selected from the group consisting of: nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, azabenzo[9,10]phenanthrene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor structural moiety and the donor structural moiety described herein may be directly linked, or via a conjugated linker group or a non-conjugated linker group (such as sp...). 3 (Carbon or silicon atoms) are linked together.

[0701] In some embodiments, the fluorescent material comprises at least one chemical structural motif selected from the group consisting of:

[0702] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0703] Where Y F Y G Y H and Y I Each of the following is independently selected: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2; and

[0704] Where X F and X G Each is independently selected from C and N.

[0705] In some of the above embodiments, any carbon ring atom in each phenyl ring of any of the above structures, up to a total of three carbon ring atoms, together with their substituents, may be replaced by N.

[0706] f) HBL:

[0707] Hole blocking layers (HBLs) can be used to reduce the number of holes and / or excitons leaving the emitter layer. The presence of such a blocking layer in a device can lead to significantly higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, blocking layers can be used to confine emission to the desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (farthest from vacuum level) and / or higher triplet energy compared to one or more emitters closest to the HBL interface.

[0708] In some embodiments, the compound used in the HBL contains the same molecules or the same functional groups as the host material described above.

[0709] In some embodiments, the compound used in HBL comprises at least one structural moiety selected from the group consisting of:

[0710] , , , , ,and , where k is an integer from 1 to 20; L 101 It is another ligand, and k' is an integer from 1 to 3.

[0711] g) ETL:

[0712] An electron transport layer (ETL) can comprise a material capable of transporting electrons. The ETL 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 they are typically used for electron transport.

[0713] In some embodiments, the compound used in the ETL contains at least one of the following structural moieties in its molecule:

[0714] , , , , , , , , , , and fullerenes, where k is an integer from 1 to 20, X 101 To X 108 Selected from C or N; Z 101 Selected from the following groups: C, N, O, and S.

[0715] In some implementations, the metal complexes used in ETL contain, but are not limited to, the following general formula:

[0716] Wherein (ON) or (NN) are bidentate ligands of metals that coordinate with atoms O, N or N, N; L 101 It is another ligand; k' is an integer from 1 to the maximum number of ligands that can be bonded to the metal.

[0717] In some embodiments, the ETL material is selected from the group consisting of: anthracene-benzimidazole compounds, azircon[9,10]phenanthrene derivatives, anthracene-benzothiazole compounds, metal 8-hydroxyquinoline compounds, metal hydroxybenzoquinoline compounds, bathocuprine compounds, 5-membered electron-deficient heterocycles (e.g., triazoles, oxadiazoles, imidazoles, benzimidazoles), thiophene compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0718] h) Charge Generation Layer (CGL)

[0719] In tandem or stacked OLEDs, the bipolar current transport layer (CGL) plays a crucial role in performance. It consists of n-doped and p-doped layers, respectively, for injecting electrons and holes. Electrons and holes are supplied from the CGL and the electrodes. Electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; then, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductive dopants used in the transport layer.

[0720] In any of the compounds disclosed herein, hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in a compound is selected from the group consisting of 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. As used herein, the percentage of deuteration has its general meaning and includes the percentage of all possible hydrogen and deuterium atoms replaced by deuterium atoms. In some embodiments, the deuterium atom is attached to an aromatic ring. In some embodiments, the deuterium atom is attached to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atom is attached to a heteroatom, such as a Si or Ge atom.

[0721] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. Therefore, the claimed invention may include variations of the specific examples and preferred embodiments described herein, which will be apparent to those skilled in the art. It should be understood that various theories regarding why the invention works are not intended to be limiting.

[0722] E. Experimental Section

[0723] In the reaction route below, "Inventive Compound" means inventive compound, and "Comparative Compound" means comparative compound.

[0724]

[0725] In a 250 mL round-bottom flask, 4,4,5,5-tetramethyl-2-(3,3,5,5-tetramethylcyclohexyl-1-en-1-yl)-1,3,2-dioxaborhexacyclopentane (3.959 g, 1.1 equivalent, 14.98 mmol) and 7-chloro-4-(4-(trimethylsilyl)naphthyl-2-yl)benzo[4,5]thieno[3,2-d]pyrimidine (5.707 g, 1 equivalent, 13.62 mmol) were dissolved in 1,4-dioxane (40.000 mL) and 2M potassium carbonate (K2CO3) aqueous solution (13.62 mL). The solution was purged with nitrogen for 13 minutes, and then dicyclohexyl (2... 6 -dimethoxy-[1,1] [-biphenyl]-2-yl)phosphine (335.5 mg, 0.06 equivalent, 817.2 μmol) and palladium(II) acetate (91.74 mg, 0.03 equivalent, 408.6 μmol). The reaction mixture was heated at 94 °C. Stir for 22 hours. Cool the reaction mixture to room temperature (approximately 25°C). C) The combined organic layers were diluted with brine (50 mL) and ethyl acetate (50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give 10.01 g of green solid. The crude solid was purified by silica gel chromatography to give 4.3 g of product.

[0726]

[0727] In a 40 mL amber scintillation flask, cyclooctadiene iridium chloride dimer (Ir(COD)Cl2) (0.940 g, 1 equivalent, 1.40 mmol) was dissolved in 1,2-dichlorobenzene (17.00 mL). The solution was purged with nitrogen for 15 min, and then 7-(3,3,5,5-tetramethylcyclohexyl-1-en-1-yl)-4-(4-(trimethylsilyl)naphthyl-2-yl)benzo[4,5]thieno[3,2-d]pyrimidine (2.92 g, 4 equivalent, 5.60 mmol) was added. The mixture was then heated at 135 °C. Stir at C for 72 hours. Transfer the crude reaction solution to the next step. Add potassium (Z)-3,7-diethyl-6-oxonon-4-en-4-ol (889.2 mg, 3 equivalents, 3.551 mmol) to the crude reaction solution. Heat the reaction mixture at 35°C... The mixture was stirred at C for 72 hours. The crude reaction mixture was cooled to room temperature and purified by column chromatography to give 0.3 g of product as a red solid.

[0728]

[0729] Following the procedure for obtaining compound 1, compound 2 can be prepared using 4-(4-isopropylnaphthyl-2-yl)-6-methyl-7-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)benzo[4,5]thieno[3,2-d]pyrimidine as a starting material.

[0730]

[0731] Following the procedure for obtaining compound 1, compound 3 can be prepared using (E)-5-(3-methylbut-1-en-1-yl)benzo[6,7]chromeno[2,3,4-ij]isoquinoline as a starting material.

[0732]

[0733] 2-(3-bromo-4-(methyl-d3)phenyl)-4,5-di(methyl-d3)pyridine can react with 4,4,5,5-tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborhexacyclopentane under Suzuki coupling conditions to form 4,5-di(methyl-d3)-2-(3',3',5',5'-tetramethyl-6-(methyl-d3)-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-3-yl)pyridine, which can react with iridium(III) chloride (IrCl3) to form the 4-dimer of the inventive compound. The dimer can be treated in solution with silver trifluoromethanesulfonate (AgOTf) to form the trifluoromethanesulfonate derivative of compound 4 of the present invention, which reacts with 8-(4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)pyridin-2-yl)-2-(methyl-d3)benzofurano[2,3-b]pyridine to form compound 5 of the present invention.

[0734]

[0735] The trifluoromethanesulfonate intermediate can be reacted with 1-(3,5-diisopropyl-3'',3'',5'',5''-tetramethyl-2'',3'',4'',5''-tetrahydro-[1,1':4',1''-triphenyl]-4-yl)-2-(phenanthro[3,2-b]benzofuran-11-yl)-1H-benzo[d]imidazole to form compound 6 of the invention.

[0736]

[0737] The trifluoromethanesulfonate intermediate can be reacted with 11-(1-(3,5-diisopropyl-3'',3'',5'',5''-tetramethyl-2'',3'',4'',5''-tetrahydro-[1,1':4',1''-triphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-8-(methyl-d3)benzo[h]benzofuran[2,3-b]quinoline to form compound 7 of the invention.

[0738] The photoluminescence (PL) properties of the invented compound 1 and the comparative compound 1 were tested in polymethyl methacrylate (PMMA) films, and the results are shown in Table 1 below.

[0739]

[0740] Table 1. Photophysical properties of the inventive compound and the comparative compound

[0741]

[0742] Compound 1 exhibits a λmax at 625 nm, a 6 nm redshift compared to Comparative Compound 1. Based on the bandgap law, efficiency begins to decrease as the emitted color shifts towards a more saturated red. However, in this invention, despite the aforementioned redshift, Compound 1 exhibits the same photoluminescence quantum yield (PLQY). In summary, the inventive compounds are expected to improve the color purity of OLED devices by emitting more saturated red light with high efficiency.

[0743] The inventive compounds were evaluated computationally. Calculations were performed using the B3LYP function and the CEP-31G basis set. Geometric optimization was performed in vacuum. Excitation energies were obtained for these optimized geometries using time-dependent density functional theory (TDDFT). A continuous solvent model was applied to simulate tetrahydrofuran solvent in the TDDFT calculations. All calculations were performed using a Gaussian procedure. The results obtained using the aforementioned density functional theory (DFT) functional set and basis set are theoretical. Calculation protocols such as Gaussian16 using the B3LYP and CEP-31G protocols used herein rely on the assumption that "electronic effects are cumulative," thus a larger basis set can be used to extrapolate complete basis set (CBS) constraints. However, when the aim of the study is to understand the variations in HOMO, LUMO, S1, T1, bond dissociation energies, etc., of a range of structurally related compounds, such cumulative effects are expected to be similar. Therefore, although the absolute error caused by using B3LYP may be significant compared to other calculation methods, the relative differences between the HOMO, LUMO, S1, T1, and bond dissociation energies calculated using the B3LYP protocol are expected to reproduce the experiments well. See, for example, Hong et al., Chem. Mater. 2016, 28, 5791-98, 5792-93 and Supplementary Information (discussing the reliability of DFT calculations in the context of OLED materials). Furthermore, for iridium or platinum complexes applicable to OLEDs, the data obtained from DFT calculations correlate very well with actual experimental data. See Tavasli et al., J. Mater. Chem. 2012, 22, 6419-29, 6422 (showing a strong correlation between DFT calculations and actual data for various emitter complexes); Morello, GR, J. Mol. Model. 2017, 23:174 (studying various DFT functional sets and basis sets and concluding that the combination of B3LYP and CEP-31G is particularly accurate for emitter complexes). The excited-state transition characteristics are determined as a post-processing step following the aforementioned DFT and TDDFT calculations. This analysis allows the excited state to be decomposed into holes (i.e., the source of the excitation) and electrons (i.e., the final position of the excited state). Furthermore, since this analysis is performed on computational performance, it is objective and reproducible; see Mai et al., Coord. Chem. Rev. 2018, 361, 74-97 (discussing the theoretical basis for the decomposition of excited states in transition metal complexes).

[0744] The calculation results are shown in Table 2 below.

[0745] Table 2. DFT results for the inventive and comparative compounds

[0746]

[0747]

[0748]

[0749]

[0750] As shown in Table 2, compared to their corresponding comparative analogs, the compounds of the present invention, characterized by novel substitution, consistently exhibit lower T1 energies. These DFT results are in good agreement with the photophysical properties summarized in Table 1. Consequently, the compounds of the present invention are expected to exhibit more saturated red emission when used as emission dopants in organic electroluminescent devices, which is considered important for improving device performance.

Claims

1. A compound having a first ligand LA, wherein the first ligand LA comprises the structure of formula I: Equation I, in: Structural part A and structural part B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring; Z1-Z4 are each independently C or N; K is selected from the following group: direct bond, O, S, Se, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ); RA and RB each independently represent monosubstitution up to the maximum permissible substitution, or no substitution; Rα, Rβ, RA, and RB are each independently hydrogen, or substituents selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; At least one of the following conditions must be true: i) At least one RA or RB contains an olefinic structural moiety, wherein if the olefinic structural moiety forms part of a ring, the ring is not aromatic; or ii) At least one of structural moiety A or structural moiety B contains a non-aromatic ring having at least one olefinic structural moiety; LA is located in metal M; M is selected from the following groups: Os, Ir, Pd, Pt, Rh, Re, Ru, Cu, Ag, and Au; M can ligand other ligands; LA can be linked with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; Any two substituents can be linked or fused to form a ring; If M is Ir, then at least one of the following conditions holds: (1) K is not a direct key; (2) Both structural part A and structural part B are polycyclic fused ring systems; (3) Z4 is C, and structural part B is a polycyclic fused ring system; (4) The compound contains a ligand LB, which contains a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system; (5) Z4 is C, and structural part B is a single ring, while structural part A is a multi-ring containing at least two rings; and The first ligand LA is not: , , , , ,or .

2. The compound of claim 1, wherein structural moiety A is selected from the following list of cyclic structural moieties: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azirabenzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, azirabenzoxazole, benzothiophene, azirabenzothiophene, benzothiazole, azirabenzothiazole, benzoselenene, azirabenzoselenene, indene, azirain, indole, azirain Indole, benzimidazole, azabenzimidazole, benzobenzimidazole, azabenzimidazole, carbazole, azacarbazole, naphthemidazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene; and / or wherein structural part B is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, Oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, azabenzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenophene, azabenzoselenophene, indole, azaindole, benzimidazole, azabenzimidazole, benzobenzimidazole, azabenzimidazole, carbazole, azacarb Azole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene; and / or at least one of the RAs contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; and / or at least one of the RBs contains a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

3. The compound of claim 1, wherein Z1 is N and Z4 is C, or wherein Z1 is a carbene carbon and Z4 is C; and / or wherein Z2 and Z3 are each C or wherein Z2 is N; and / or wherein K is a direct bond, O or S; and / or wherein the metal M is Ir or Pt; or Wherein K is not a direct bond; and / or where structural moiety A and structural moiety B are both polycyclic fused ring systems; and / or where two RAs are linked or fused together to form a non-aromatic ring containing at least one olefinic structural moiety; and / or where two RBs are linked or fused together to form a non-aromatic ring containing at least one olefinic structural moiety.

4. The compound of claim 1, wherein Z4 is C, and structural moiety B is a polycyclic fused ring system having exactly two fused rings or at least four rings; and / or wherein the compound comprises a ligand LB, the ligand LB comprising a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system comprising at least four rings, wherein each ring of the polycyclic fused ring system of the structural moiety G is independently a 5- to 10-membered carbon ring or heterocyclic ring.

5. The compound of claim 1, wherein at least one RA or RB has the structure of formula III: Formula III, in: If the olefin structural portion is directly bonded to structural portion A or structural portion B, then the dashed bond indicates the bond connected to structural portion A or structural portion B; or the dashed bond indicates the bond connected to RA or RB respectively bonded to structural portion A or structural portion B. n is 0, 1, 2, 3, or 4; When n is 0, Equation III is directly bonded to structural part A or structural part B, or bonded to RA or RB respectively bonded to structural part A or structural part B; Each of R1, R2, R3, R4, and R5 is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; Any two substituents can be linked or fused to form a ring; and R1, R2, R3, R4, or R5 can be connected to or fused with adjacent RA or RB to form a ring.

6. The compound of claim 1, wherein the olefin structural portion forms part of a ring, which is achieved by using... The two carbon atoms of the label are attached to structural moiety A or structural moiety B, and the olefin structural moiety comprises or has a structure of formula IIIB: Formula IIIB, in, n1 and n2 are each independent integers from 0 to 20; RAB indicates monosubstitution up to the maximum permissible substitution, or no substitution; Each RAB is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and Any two substituents may optionally be linked or fused to form a ring.

7. The compound of claim 1, wherein the ligand LA is selected from the structures listed in A1 below: ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， , , ， ， , ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ; in: T is selected from the following groups: B, Al, Ga, and In; K1' is selected from the following group: single bond, O, S, NRe, PRe, BRe, CReRf and SiReRf; Each of Y1-Y118 and V1-V129 is independently selected from C and N; Each of Ya', Y' and Y'' is independently selected from the following group: BRe, BReRf, NRe, PRe, P(O)Re, O, S, Se, C=O, C=S, C=Se, C=NRe, C=CReRf, S=O, SO2, CReRf, SiReRf and GeReRf; The single bonds between Y24 and V1, Y37 and V1, Y56 and V1, Y24 and V7, Y37 and V7, and Y71' and V7 drawn by dashed lines can be arbitrarily present; The single bond groups drawn by the dashed lines Y8-W1-V1, Y32-W1-V1, Y8-W1-V7, and Y32-W1-V7 can be arbitrarily selected. When a single bond group exists, the respective groups V1, V7, Y8, and Y32 are carbon. W1 is selected from the following groups: direct bond, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR', and GeRR'. When the single bonds between Y8-W1-V1, Y32-W1-V1, Y8-W1-V7, and Y32-W1-V7 do not exist, then W1 also does not exist. The single bonds between Y8 and W2, and between W2 and V7, drawn by the dashed lines, are arbitrarily present. When they are present, V7 and Y8 are each carbon, and W2 is B, N, P, CR, SiR, or GeR. When the single bonds between Y8 and W2, and between W2 and V7, are not present, W2 is selected from the following group: direct bonds, BR, NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CRR', P(O)R, SiRR', and GeRR'. It is a connection point with one of V5-V8, V13-V16, or V25-V28; Each of Ra', Rb', Rc' and Rd' independently represents one to the maximum allowed number of substitutions, or represents no substitution; Each of R, R', Ra1, Rb1, Rc1, Rd1, Ra', Rb', Rc', Rd', Re and Rf is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; Any two substituents of R, R', Ra1, Rb1, Rc1, Rd1, Ra', Rb', Rc', Rd', Re, and Rf can fused or linked to form a ring or a polydentate ligand; and At least one of Ra' or Rb' is a structure containing formula III or formula IIIA, or has a structure of formula IIIC. The olefinic structural portion, wherein the structure of formula IIIC has formula P#, where # is an integer from 1 to 428, wherein each of P1 to P365 is selected from the structures defined in list A1 below; each of P366 to P428 is selected from the structures defined in list A2 below; or at least one ring of the above structures is fused to the structure of formula IIIB, or fused to the structures W1 to W23 defined in list A3 below; List A1 has the following structure: List A2 has the following structure: And list A3 has the following structure: , , , , , , , , , , , , , , , , , , , , , ,and .

8. The compound of claim 1, wherein the ligand LA is selected from LAa-n-(REA)(REB)(REC)(RED)(REE)(REF), where n is an integer from 1 to 150; REA is selected from P1-P428, each of REB, REC, RED, REE and REF is independently selected from U1-U126; and each of LAa-1-(P1)(U1)(U1)(U1)(U1) to LAa-150-(P428)(U126)(U126)(U126)(U126)(U126) is defined as in the following List 3: Where P1 to P428 have the structures defined in List A1 and List A2 below; and U1 to U126 have the structures defined in the following list C; List A1 has the following structure: List A2 has the following structure: And list C has the following structure: ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， , ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

9. The compound of claim 1, wherein the compound has the structural formula M(LA)p(LB)q(LC)r, wherein LB and LC are each bidentate ligands; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of metal M.

10. The compound of claim 9, wherein LB and LC are each independently selected from the structures listed in List 4 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ; in: T is selected from the following groups: B, Al, Ga, and In; K1' is selected from the following group: single bond, O, S, NRe, PRe, BRe, CReRf and SiReRf; Each of Y1-Y13 is independently selected from C and N; Y' is selected from the following groups: BRe, BReRf, NRe, PRe, P(O)Re, O, S, Se, C=O, C=S, C=Se, C=NRe, C=CReRf, S=O, SO2, CReRf, SiReRf and GeReRf; Re and Rf can fused or connected to form a ring; Ra, Rb, Rc, and Rd each independently represent one to the maximum allowed number of substitutions, or no substitutions; Each of Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, Rd, Re, and Rf is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boralkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and Any two substituents in Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, and Rd can be fused or linked to form a ring or a polydentate ligand.

11. The compound of claim 9, wherein the compound has the formula Ir(LA)3, Ir(LA)(LBk)2, Ir(LA)2(LBk), Ir(LA)2(LCj-I), Ir(LA)2(LCj-II), Ir(LA)(LBk)(LCj-I), or Ir(LA)(LBk)(LCj-II). Where LA conforms to formula I; Where k is an integer from 1 to 544, and each LBk has a structure defined in the following Listing 6: ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， , , , , , , , , ， ， ， ， ， ， , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， , ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and ; Each LCj-I has a formula based on The structure; and each LCj-II has a structure based on formula The structure, wherein for each LCj in LCj-I and LCj-II, R201 and R202 are each independently defined as shown in Listing 7 below: And RD1-RD246 have the structure shown in List D: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

12. The compound of claim 9, wherein the compound is selected from the structures listed in List 10: , , , , , , , , , , , , ， , ， , ， , . ， ， , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， ， ， , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,and .

13. The compound of claim 9, wherein the compound has the structure of formula IV: Formula IV, in: M1 is either Pd or Pt; Structural components E and F are each independently a monocyclic or polycyclic ring structure, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring; Z3 and Z4 are each independently C or N; K, K3, and K4 are each independently selected from the following group: direct bonds, O, and S, wherein at least two of them are direct bonds; L1, L2, and L3 are not present independently, or are selected from the group consisting of: direct bonds, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, aryl, heteroaryl, and combinations thereof, wherein at least one of L1 or L2 is present; RE and RF each independently represent zero, one, or up to the maximum allowed number of substitutions; Each of R, R', RE, and RF is independently hydrogen, or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and Two adjacent RA, RB, RC, RE, and RF can be connected or fused together to form a ring.

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

15. A compound, either in its neutral molecular form, or in its monovalent or polyvalent form, or in its monomeric or polymeric form, or in its macromolecular or supramolecular form, wherein said compound has a first ligand LA, the first ligand LA comprising the structure of formula I: Equation I, in: Structural part A and structural part B are each independently a monocyclic or polycyclic fused ring system, wherein each ring of the monocyclic or polycyclic fused ring system is independently a 5- to 10-membered carbon ring or heterocyclic ring; Z1-Z4 are each independently C or N; K is selected from the following group: direct bond, O, S, Se, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ); RA and RB each independently represent monosubstitution up to the maximum permissible substitution, or no substitution; Rα, Rβ, RA, and RB are each independently hydrogen, or substituents selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; At least one of the following conditions must be true: i) At least one RA or RB contains an olefinic structural moiety, wherein if the olefinic structural moiety forms part of a ring, the ring is not aromatic; or ii) At least one of structural moiety A or structural moiety B contains a non-aromatic ring having at least one olefinic structural moiety; LA is located in metal M; M is selected from the following groups: Os, Ir, Pd, Pt, Rh, Re, Ru, Cu, Ag, and Au; M can ligand other ligands; LA can be linked with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; Any two substituents can be linked or fused to form a ring; If M is Ir, then at least one of the following conditions holds: (1) K is not a direct key; (2) Both structural part A and structural part B are polycyclic fused ring systems; (3) Z4 is C, and structural part B is a polycyclic fused ring system; (4) The compound comprises a ligand LB, which comprises a structural moiety G, wherein the structural moiety G is coordinated to a metal M and is a polycyclic fused ring system, wherein each ring of the polycyclic fused ring system of the structural moiety G is independently a 5- to 10-membered carbon ring or a heterocyclic ring. (5) Z4 is C, and structural part B is a single ring, while structural part A is a multi-ring containing at least two rings; and The first ligand LA is not: , , , , ,or .

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