Organic electroluminescent materials and devices

Abstract

This application relates to organic electroluminescent materials and devices. An OLED having an emissive layer with a compound Ir(L A )2(L B ), L A has the structure, and L B has the structure. At least one of the B group or the D group is a polycyclic fused ring system.

Description

Cross-reference of related applications

[0001] This application claims priority to U.S. Provisional Application No. 63 / 774,324, filed March 19, 2025, pursuant to 35 USC § 119(e), the entire contents of which are incorporated herein by reference. Technical Field

[0002] 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 devices and consumer products. Background Technology

[0003] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly popular. Many of the materials used to manufacture these 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.

[0004] 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.

[0005] 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 the CIE coordinate system, well-known in the field. Summary of the Invention

[0006] In one aspect, this disclosure provides an organic electroluminescent device (OLED) comprising:

[0007] anode;

[0008] cathode; and

[0009] An emitting layer disposed between the anode and the cathode;

[0010] The emission layer includes the formula Ir(L) A )2(L B The first compound of );

[0011] Where L A Including I The structure, and

[0012] L B Included II The structure;

[0013] in:

[0014] Groups A, B, C, and D 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.

[0015] At least one of the B group or the D group is a polycyclic fused ring system;

[0016] Z 1 To Z 8 Each can be either C or N independently;

[0017] L 1 and L 2 Each of the following groups is independently selected: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CRR', S=O, SO2, CR, CRR', SiRR', and GeRR';

[0018] K 1 and K 2 Choose from the following groups: direct key, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R α (R) β ) and Si(R α (R) β );

[0019] R A R B R C and R D Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0020] Each R, R', R α R β R A R B R C and R DIndependently, 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof;

[0021] L A and L B They are different; and

[0022] Ir(L A The first triplet excited state energy of )3 is lower than that of Ir(L B The first triplet excited state energy of )3, or L A The molecular weight is greater than L B The molecular weight.

[0023] In another aspect, this disclosure provides an OLED comprising an anode;

[0024] cathode; and

[0025] An emitting layer disposed between the anode and the cathode;

[0026] The emission layer includes the formula Ir(L) A )2(L B The first compound of );

[0027] Where L A Including I The structure, and

[0028] L B Included II The structure;

[0029] in:

[0030] Groups A, B, C, and D 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.

[0031] At least one of the B group or the D group is a polycyclic fused ring system;

[0032] Z 1 To Z 8 Each can be either C or N independently;

[0033] L 1 and L 2Each of the following groups is independently selected: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CRR', S=O, SO2, CR, CRR', SiRR', and GeRR';

[0034] K 1 and K 2 Choose from the following groups: direct key, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R α (R) β ) and Si(R α (R) β );

[0035] R A R B R C and R D Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0036] Each R, R', R α R β R A R B R C and R D 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof;

[0037] L A and L B They are different;

[0038] Ir(L A The first triplet excited state energy of )3 is lower than that of Ir(L B The first triplet excited state energy of )3, or L A The molecular weight is greater than L B The molecular weight; and one or both of the following are true:

[0039] (1) Ir(L A )2(L B The photoluminescence spectrum of Ir(L) has an emission peak, which has a full width at half maximum (FWHM) (1); A (L) BThe photoluminescence spectrum of )2 has an emission peak, which has a full width at half maximum (FWHM) (2); and FWHM (2) - FWHM (1) is equal to or greater than 2 nm;

[0040] (2) Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.01.

[0041] In another aspect, this disclosure provides a consumer product comprising an OLED as described herein. Attached Figure Description

[0042] Figure 1 An organic light-emitting device is shown.

[0043] Figure 2 An inverted organic light-emitting device without an independent electron transport layer is demonstrated.

[0044] Figure 3 This demonstrates modeled data for p-polarized emission. Detailed Implementation

[0045] A. Terminology

[0046] Unless otherwise specified, the following terms as used herein are defined as follows:

[0047] 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 further away from the substrate. Unless specified that the first layer "contacts" the second layer, 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.

[0048] As used herein, “solution-handleable” means capable of dissolving, dispersing or transporting in and / or depositing from a liquid medium in the form of a solution or suspension.

[0049] As used herein, and as will generally be understood by those skilled in the art, if the 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 than" or "higher than" the second HOMO or LUMO level. Since 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 levels of a material are higher than the HOMO levels of the same material. "Higher" HOMO or LUMO levels appear to be closer to the top of this diagram than "lower" HOMO or LUMO levels.

[0050] As used herein, and as will generally be 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 the “higher” work function is more negative. On a conventional energy level diagram with the vacuum level at the top, the “higher” work function is illustrated as being farther 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.

[0051] This document may describe light emission regions by referring to the color of the light emitted by layers, materials, areas, and devices. Generally, as used herein, an emitting region that produces a particular color of light may include one or more emitting layers disposed in a stacked manner on top of each other.

[0052] 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 the highest emission spectral peak in 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.

[0053] 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. This color-changing layer can be configured to shift the wavelength of light emitted by the other layer by a defined amount, such as by the difference between the wavelength of the emitted light and the wavelength of the resulting light. Generally, there are two types of color-changing layers: color filters that modify the spectrum by removing light of unwanted wavelengths, and color-changing layers that convert higher-energy photons into lower-energy ones. For example, a "red" filter may be present to filter input light to remove light with wavelengths outside the approximately 580-700 nm range. The component of "color" refers to the component of light that produces or otherwise emits a specific color as described above when activated or used. For example, "a first emission region of a first color" and "a second emission region of a second color different from the first color" describe two emission regions that emit two different colors as described above when activated within the device.

[0054] As used herein, the light initially generated by a material, layer, or region is the exact opposite of the light ultimately emitted by the same or different structures, allowing the emitting materials, layers, and regions to be distinguished from each other and from other 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 produce blue light, which can be converted into red or green light by a color filter, quantum dot, or other structure, causing the entire emitting stack or subpixel to emit red or green light. In this case, the initial emitting material, region, or layer may be referred to as the "blue" component, even if the subpixel is the "red" or "green" component.

[0055] In some cases, the color of components, such as emission regions, subpixels, color-changing layers, etc., can preferably be described according to 1931 CIE coordinates. For example, a yellow emitting material may have multiple peak emission wavelengths, one in or near the edge of the "green" region and one in or near the edge of the "red" region, as previously described. Therefore, as used herein, each color item also corresponds to a shape in the 1931 CIE coordinate color space. The shape in the 1931 CIE color space is constructed by tracing the trajectory between two color points and any other interior points. For example, the interior shape parameters for red, green, blue, and yellow can be defined as follows:

[0056]

[0057] The terms “halogen,” “halogen,” and “halogen group” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0058] The term "acyl" refers to a substituted carbonyl group (-C(O)-R). s ).

[0059] The term "ester" refers to a substituted oxycarbonyl group (-OC(O)-R). s or -C(O)-OR s ) group.

[0060] The term "ether" refers to -OR s Group.

[0061] The terms "thio-" or "thioether" are used interchangeably and refer to -SR s Group.

[0062] The term "selenyl" refers to -SeR s Group.

[0063] The term "sulfinyl" refers to -S(O)-R s Group.

[0064] The term "sulfonyl" refers to -SO2-R s Group.

[0065] The term "phosphono" refers to a group containing at least one phosphorus atom bonded to the relevant structure. Common examples of phosphono 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.

[0066] The term "silyl group" refers to a group containing at least one silicon atom bonded to the relevant structure. Common examples of silyl groups include, but are not limited to, -Si(R s)3 groups, wherein each R s They can be the same or different.

[0067] 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.

[0068] The term "boronyl" refers to a group containing at least one boron atom bonded to the relevant structure. Common examples of boronyl 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.

[0069] In each of the above, R s It can be hydrogen or a substituent selected from the group of general substituents as 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 Choose from the following groups: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0070] 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 1 to 15 carbon atoms, preferably 1 to 9 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.

[0071] 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.

[0072] The terms "heteroalkyl" or "heterocyclic alkyl" refer to an alkyl or cycloalkyl group having at least one carbon atom substituted with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Furthermore, the heteroalkyl or heterocyclic alkyl group may be further substituted.

[0073] 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 originates from a carbon-carbon double bond bonded to the associated structure. A cycloalkenyl is essentially a cycloalkyl group comprising at least one carbon-carbon double bond in a cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom substituted by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Furthermore, alkenyl, cycloalkenyl, or heteroalkenyl groups may be further substituted.

[0074] 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, where one carbon atom originates from a carbon-carbon triple bond bonded to the relevant structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Furthermore, the alkynyl group may be further substituted.

[0075] 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, aralkyl groups may be further substituted.

[0076] 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. Heteroaromatic cyclic groups can be used interchangeably with heteroaryl groups. Preferred non-aromatic heterocyclic groups are non-aromatic heterocyclic groups containing 3 to 10 ring atoms, preferably non-aromatic heterocyclic groups containing 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines such as morpholino, piperidinyl, pyrrolyl, etc., and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Furthermore, the heterocyclic group may be further substituted or fused.

[0077] The term "aryl" refers to and includes both monocyclic and polycyclic aromatic hydrocarbon groups. A polycyclic aromatic hydrocarbon can have two or more rings, wherein two carbons are common to two adjacent rings (the rings are "fused"). Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty-four carbon atoms, six to eighteen carbon atoms, and more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, twelve, fourteen, or eighteen carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, pyrene, β-carotene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, and naphthalene. Furthermore, aryl groups can be further substituted or fused, such as, but not limited to, fluorene.

[0078] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom. Heteroatoms include, but are not limited to, O, S, Se, N, P, B, Si, Ge, and Se. In many cases, O, S, N, or B are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Polycyclic heterocyclic systems may have two or more aromatic rings, wherein two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is a heteroaryl. Polycyclic heteroaromatic ring systems may have one to six heteroatoms in each ring. Preferred heteroaryls are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, Indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, aziborane, 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, heteroaryl groups can be further substituted or fused.

[0079] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, and 5λ are included. 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene groups, and their corresponding aza analogs are of particular interest.

[0080] 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, thio, selenyl, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0081] 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, thioyl, and combinations thereof.

[0082] 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, thio, and combinations thereof.

[0083] 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.

[0084] In other cases, the most preferred general substituent is selected from the group consisting of: deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0085] In the absence of a specific definition of one or more substituents (e.g., R, R', R'', R), A R A R 1 In the case of R1, etc., each of the one or more substituents should be understood to independently represent hydrogen or a substituent selected from the group consisting of general substituents as defined herein. Similarly, each of the one or more substituents may optionally be coupled or fused with another substituent to form a ring. It should also be understood that any substituent selected from general substituents as defined herein may also be selected from preferred general substituents as defined herein, more preferred general substituents as defined herein, even more preferred general substituents as defined herein, or most preferred general substituents as defined herein.

[0086] 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 R represents zero or no substitution, 1 For example, it could be hydrogen atoms with all available valences in the ring atom, such as carbon atoms in benzene and nitrogen atoms in pyrrole, or simply none for ring atoms with fully saturated valences, such as nitrogen atoms 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.

[0087] As used herein, “combination thereof” 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.

[0088] The term "aza" in the phrases used herein, namely aza-dibenzofuran, aza-dibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic ring by a nitrogen atom. For example, and without limitation, azatriphenylene covers dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derived compounds described above will readily be contemplated by those skilled in the art, and all such analogs are intended to be covered by the terminology set forth herein.

[0089] 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.

[0090] Examples of suitable isotopes to be included in compounds of this disclosure include isotopes of hydrogen, for example... 2 H and 3 H; 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.

[0091] Certain isotopically labeled compounds disclosed herein, such as those doped 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) It is particularly suitable for this purpose due to its ease of incorporation and convenient detection methods.

[0092] Using heavier isotopes such as deuterium (i.e., 2 H) replacement can provide some advantages resulting from greater stability, and may therefore be preferred in some cases.

[0093] The isotopically labeled compounds disclosed herein 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.

[0094] Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterated organometallic complexes. Further references to Ming Yan et al., Tetrahedron 2015, 71, 1425-30, and Atzrodt et al., Angewandte Chemie Int. Ed. (Review) 2007, 46, 7744-65 (which are incorporated herein by reference in their entirety) describe efficient methods for the deuteration of methylene hydrogen in benzylamine and the replacement of aromatic cyclic hydrogens with deuterium, respectively.

[0095] As used herein, any specifically listed substituent, such as, but not limited to, methyl, phenyl, pyridyl, etc., includes its undeuterated, partially deuterated, and fully deuterated forms. Similarly, substituents, such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc., also include their undeuterated, partially deuterated, and fully deuterated forms. Unless otherwise specified, atoms in a chemical structure that are not completely filled with H or D should be considered to include their undeuterated, partially deuterated, and fully deuterated forms. For example, chemical structures This refers to C6H6, C6D6, C6H3D3, and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, but are not limited to, CD3, CD2C(CH3)3, C(CD3)3, and C6D5. Similarly, where the partially or fully defined atomic structure indicates that a particular position can be deuterated, the same atomic structure with one, two, or at most all deuterated atoms replaced by hydrogen can also be conceived.

[0096] It should be understood that when a molecular fragment is described as a substituent or additionally attached to another group, 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). As used herein, these different ways of naming substituents or attached fragments are considered equivalent.

[0097] In some cases, a pair of substituents in a molecule may join or fuse to form a ring. Preferred rings are five- to nine-membered carbon rings or heterocycles, including both cases where the ring formed by the pair of substituents is partially saturated and cases where the ring formed by the pair of substituents is partially unsaturated. In other cases, a pair of adjacent substituents may join or fuse to form a ring. As used herein, “adjacent” means that the two substituents involved may be adjacent to each other on the same ring, or on two neighboring rings having two closest available substituted positions (such as the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene).

[0098] B. OLEDs and devices disclosed herein

[0099] In one aspect, this disclosure provides an organic electroluminescent device (OLED) comprising:

[0100] anode;

[0101] cathode; and

[0102] An emitting layer disposed between the anode and the cathode;

[0103] The emission layer includes the formula Ir(L) A )2(L B The first compound of );

[0104] Where L A Including I The structure, and

[0105] L B Included II The structure;

[0106] in:

[0107] Groups A, B, C, and D 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.

[0108] At least one of the B group or the D group is a polycyclic fused ring system;

[0109] Z 1 To Z 8 Each can be either C or N independently;

[0110] L 1 and L 2 Each of the following groups is independently selected: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CRR', S=O, SO2, CR, CRR', SiRR', and GeRR';

[0111] K 1 and K 2 Choose from the following groups: direct key, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R α (R) β ) and Si(R α (R) β );

[0112] R A R B R C and R D Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0113] Each R, R', R α R β R A R B R C and R D 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof;

[0114] L A and L B They are different; and

[0115] Ir(L A The first triplet excited state energy of )3 is lower than that of Ir(L B The first triplet excited state energy of )3, or L A The molecular weight is greater than L B The molecular weight.

[0116] In some embodiments, at least one of the following conditions is true:

[0117] (1) Ir(L A )2(L B The photoluminescence spectrum of Ir(L) has an emission peak, which has a full width at half maximum (FWHM) (1); A (L) B The photoluminescence spectrum of )2 has an emission peak, which has a full width at half maximum (FWHM) (2); and FWHM (2) - FWHM (1) is equal to or greater than 2 nm;

[0118] (2) Ir(L A (L) B The ratio of 2's full width at quarter maximum (FWQM) to Ir(L) A )2(L B The FWQM is at least 2 nm larger;

[0119] (3) Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of 2 is at least 0.01;

[0120] (4) Ir(L A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max Larger than 1 nm;

[0121] (5) Ir(L A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of 2 is at least 3% greater;

[0122] (6) Ir(L A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio is at least 0.02 greater than that of the other two.

[0123] (7) At 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage must be at least 0.05 V; or

[0124] (8) The emission layer contains fluorescent dopants.

[0125] In some embodiments of Formula I, at least one R, R', R α R β R A R B R C Or R DThe group consisting of substituents as defined herein is selected. In some embodiments, at least one R is selected from the group consisting of substituents as defined herein. In some embodiments, at least one R' is selected from the group consisting of substituents as defined herein. In some embodiments, at least one R α Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R β Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R C Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R D Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R, R', R α R β R A R B R C Or R D Choose from the group of preferred general substituents as defined herein.

[0126] In some embodiments of Formula I, at least one R, R', R α R β R A R B R C and R D It is partially or fully deuterated. In some embodiments, at least one R or R' is partially or fully deuterated. In some embodiments, R α Or R β At least one of them is partially or fully deuterated. In some embodiments, at least one R A It is partially or fully deuterated. In some embodiments, at least one R B It is partially or fully deuterated. In some embodiments, at least one R C It is partially or fully deuterated. In some embodiments, at least one R D It is partially or completely deuterated.

[0127] Despite Z 1 and Z 2 The bonds between them are shown as single bonds, but it should be understood that said bonds can be any other bonds necessary to form the applicable ring of group A. This also applies to any other generalized ring or group structures disclosed herein, including Z. 3 -Z4 Z 5 -Z 6 and Z 7 -Z 8 .

[0128] In some embodiments, groups A, B, C, and D 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.

[0129] In some embodiments, groups A, B, C, and D 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.

[0130] In some embodiments, the emitter layer includes at least one of a hole transporter and an electron transporter.

[0131] In some embodiments, the emitter layer (EML) includes a hole transport element. In some embodiments, the EML includes an electron transport element. In some embodiments, the EML includes both a hole transport element and an electron transport element.

[0132] In some embodiments, each R, R', R α R β R A R B R C and R D It is hydrogen independently or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0133] In some embodiments, each R, R', R α R β R A R B R C and R D Independently, it is hydrogen or a substituent selected from the group of preferred general substituents as defined herein. In some embodiments, each R, R', R α R β R A R B R C and R D Substituents that are independently hydrogen or selected from the group consisting of more preferred general substituents as defined herein. In some embodiments, each R, R', R α R β R AR B R C and R D Substituents that are independently hydrogen or selected from the group consisting of even more preferred general substituents as defined herein. In some embodiments, each R, R', R α R β R A R B R C and R D Substituents that are independently hydrogen or selected from the group of most preferred general substituents as defined herein.

[0134] In some embodiments, exactly one of conditions (1) to (8) is true.

[0135] In some embodiments, condition (1) is true and FWHM(2) - FWHM(1) is equal to or greater than 2 nm. In some embodiments, FWHM(2) - FWHM(1) is equal to or greater than 3 nm. In some embodiments, FWHM(2) - FWHM(1) is equal to or greater than 5 nm. In some embodiments, FWHM(2) - FWHM(1) is equal to or greater than 8 nm. In some embodiments, FWHM(2) - FWHM(1) is equal to or greater than 10 nm.

[0136] In some embodiments, condition (2) is true, and Ir(L) A (L) B )2 quarter-height full width aspect ratio Ir(L A )2(L B The full width at least 2 nm is one-quarter of the height of Ir(L). In some embodiments, Ir(L) A (L) B )2 quarter-height full width aspect ratio Ir(L A )2(L B The full width at least 3 nm is one-quarter of the height of Ir(L). In some embodiments, Ir(L) A (L) B )2 quarter-height full width aspect ratio Ir(L A )2(L B The full width at least 5 nm is one-quarter of the height of Ir(L). In some embodiments, Ir(L) A (L) B )2 quarter-height full width aspect ratio Ir(L A )2(L B The full width at least 8 nm is one-quarter of the height of Ir(L). In some embodiments, Ir(L) A (L) B )2 quarter-height full width aspect ratio Ir(L A)2(L B (A quarter of the height of the full width is at least 10 nm.)

[0137] In some embodiments, condition (3) is true, and Ir(L) A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.01. In some embodiments, Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.02. In some embodiments, Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.03. In some embodiments, Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.05. In some embodiments, Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of 2 is at least 0.10.

[0138] In some embodiments, condition (4) is true, and Ir(L) A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max At least 1 nm in size. In some embodiments, Ir(L A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max At least 2 nm in size. In some embodiments, Ir(L A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max At least 3 nm in size. In some embodiments, Ir(L A (L) B )2 of λ max Compared to Ir(L)A )2(L B ) of λ max At least 5 nm in size. In some embodiments, Ir(L A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max At least 8 nm.

[0139] In some embodiments, condition (5) is true, and Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of Ir(L) is at least 3%. In some embodiments, Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of Ir(L) is at least 5%. In some embodiments, Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of Ir(L) is at least 8%. In some embodiments, Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of Ir(L) is at least 10%. In some embodiments, Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of Ir(L) is at least 15%. In some embodiments, Ir(L) A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of 2 is at least 25%.

[0140] In some embodiments, condition (6) is true, and Ir(LA)(L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio of Ir(L) is at least 0.02 greater. In some embodiments, Ir(L) A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L BThe vertical dipole ratio of Ir(L) is at least 0.03 greater. In some embodiments, Ir(L) A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio of Ir(L) is at least 0.05 greater. In some embodiments, Ir(L) A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio of Ir(L) is at least 0.10 greater. In some embodiments, Ir(L) A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio is at least 0.15 greater.

[0141] In some embodiments, condition (7) is true, and at 10 mA / cm 2 At that time, Ir(LA)(L B The voltage ratio of )2 to Ir(L) A )2(L B The voltage is at least 0.05 V. In some embodiments, at 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage is at least 0.08 V. In some embodiments, at 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage is at least 0.10 V. In some embodiments, at 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage is at least 0.15 V. In some embodiments, at 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage is at least 0.20 V. In some embodiments, at 10 mA / cm 2 At that time, Ir(L A (L) BThe voltage ratio of )2 to Ir(L) A )2(L B The voltage must be at least 0.25 V.

[0142] In some embodiments, condition (8) is true, and the emission layer contains a fluorescent dopant.

[0143] In some embodiments, two of conditions (1) to (8) are true.

[0144] In some embodiments, three of conditions (1) to (8) are true.

[0145] In some embodiments, four of conditions (1) through (8) are true.

[0146] In some embodiments, five of conditions (1) through (8) are true.

[0147] In some embodiments, seven of conditions (1) to (8) are true.

[0148] In some embodiments, conditions (1) and (2) are both true. In some embodiments, conditions (1) and (3) are both true. In some embodiments, conditions (1) and (4) are both true. In some embodiments, conditions (1) and (5) are both true. In some embodiments, conditions (1) and (6) are both true. In some embodiments, conditions (1) and (7) are both true. In some embodiments, conditions (1) and (8) are both true. In some embodiments, conditions (2) and (3) are both true. In some embodiments, conditions (2) and (4) are both true. In some embodiments, conditions (2) and (5) are both true. In some embodiments, conditions (2) and (6) are both true. In some embodiments, conditions (2) and (7) are both true. In some embodiments, conditions (2) and (8) are both true. In some embodiments, conditions (3) and (4) are both true. In some embodiments, conditions (3) and (5) are both true. In some embodiments, conditions (3) and (6) are both true. In some embodiments, conditions (3) and (7) are both true. In some embodiments, conditions (3) and (8) are both true. In some embodiments, conditions (1), (2) and (3) are all true.

[0149] In some embodiments, each of conditions (1) to (8) is true.

[0150] In some embodiments, group A is selected from the group consisting of the following list of cyclic groups: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenphene, aza-benzoselenphene Indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, carbazole, aza-carbazole, naphthemidazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, aza-dibenzosilylfluorene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, the aza variant includes an N on the benzo ring. In some embodiments, the aza variant includes an N on the benzo ring and said N is coordinated to a metal M.

[0151] In some embodiments, the A group is a monocyclic ring.

[0152] In some embodiments, the A group is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0153] In some embodiments, group A is benzene, pyrimidine, or pyridine. In some embodiments, group A is benzene. In some embodiments, group A is pyridine.

[0154] In some embodiments, group A is a polycyclic fused ring system.

[0155] In some embodiments, the A group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole. Benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0156] In some embodiments, group A is naphthalene, quinoline, benzofuran, aza-benzofuran, phenanthrene[3,2-b]benzofuran, benzothiophene, aza-benzothiophene, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, or aza-dibenzosilylfluorene. In some embodiments, group A is benzimidazole.

[0157] In some embodiments, the A group comprises exactly two fused rings.

[0158] In some embodiments, the B group is selected from the group consisting of the list of cyclic groups defined herein.

[0159] In some embodiments, the B group is a monocyclic ring.

[0160] In some embodiments, the B group is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0161] In some embodiments, the B group is benzene, pyrimidine, or pyridine. In some embodiments, the B group is benzene. In some embodiments, the B group is pyridine.

[0162] In some embodiments, the B group is a polycyclic fused ring system.

[0163] In some embodiments, the B group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole. Benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0164] In some embodiments, the B group is naphthalene, quinoline, benzofuran, aza-benzofuran, phenanthrene[3,2-b]benzofuran, benzothiophene, aza-benzothiophene, benzimidazole, aza-benzothiophene, benzobenzimidazole, aza-benzobenzimidazole, benzimidazole-derived carbene, aza-benzothiophene-derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, fluorene, dibenzosilfluorene, or aza-dibenzosilfluorene. In some embodiments, the B group is dibenzofuran. In some embodiments, the B group is aza-dibenzofuran. In some embodiments, the B group is fluorene. In some embodiments, the B group is dibenzosilfluorene.

[0165] In some embodiments, the B group is further cyclized by a B' group, wherein the B' group 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. In some embodiments, each ring of the monocyclic or polycyclic fused ring system of the B' group is a 5- or 6-membered carbon ring or heterocyclic ring. In some embodiments, each ring of the monocyclic or polycyclic fused ring system of the B' group is a 5- or 6-membered aryl or heteroaryl ring.

[0166] In some embodiments, the B' group is selected from the group consisting of the list of cyclic groups defined herein.

[0167] In some embodiments, the B' group is a monocyclic ring. In some embodiments, the B' group is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0168] In some embodiments, the B' group is benzene, pyridine, or oxazole. In some embodiments, the B' group is benzene. In some embodiments, the B' group is pyridine. In some embodiments, the B' group is oxazole.

[0169] In some embodiments, the B group is dibenzofuran and the B' group is pyridine. In some embodiments, the B group is azir-dibenzofuran and the B' group is benzene.

[0170] In some embodiments, the B' group is a polycyclic fused ring system.

[0171] In some embodiments, the B' group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiphene, aza-dibenzothiphene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, dibenzosilfluorene, aza-dibenzosilfluorene, phenanthridine, fluorene, and aza-fluorene.

[0172] In some embodiments, the B' group is naphthalene, quinoline, benzofuran, aza-benzofuran, benzothiophene, aza-benzothiophene, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, or aza-dibenzosilylfluorene. In some embodiments, the B' group is naphthalene. In some embodiments, the B' group is benzofuran.

[0173] In some embodiments, the B group is dibenzofuran and the B' group is naphthalene or benzofuran. In some embodiments, the B group is azir-dibenzofuran and the B' group is naphthalene.

[0174] In some embodiments, the C group is selected from the group consisting of the list of cyclic groups defined herein.

[0175] In some embodiments, the C group is a monocyclic ring.

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

[0177] In some embodiments, the C group is benzene, pyrimidine, or pyridine. In some embodiments, the C group is benzene. In some embodiments, the C group is pyridine.

[0178] In some embodiments, the C group is a polycyclic fused ring system.

[0179] In some embodiments, the C group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole. Benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0180] In some embodiments, the C group is naphthalene, quinoline, benzofuran, azir-benzofuran, phenanthrene[3,2-b]benzofuran, benzothiophene, azir-benzothiophene, benzimidazole, azir-benzothiophene, benzobenzimidazole, azir-benzobenzimidazole, benzimidazole-derived carbene, azir-benzothiophene-derived carbene, carbazole, azir-carbazole, dibenzofuran, azir-dibenzofuran, dibenzothiophene, azir-dibenzothiophene, fluorene, dibenzosilfluorene, or azir-dibenzosilfluorene. In some embodiments, the C group is benzimidazole.

[0181] In some embodiments, the D group is selected from the group consisting of the list of cyclic groups defined herein.

[0182] In some embodiments, the D group is a monocyclic ring.

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

[0184] In some embodiments, the D group is benzene, pyrimidine, or pyridine. In some embodiments, the D group is benzene. In some embodiments, the D group is pyridine.

[0185] In some embodiments, the D group is a polycyclic fused ring system.

[0186] In some embodiments, the D group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole. Benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

[0187] In some embodiments, the D group is naphthalene, quinoline, benzofuran, azir-benzofuran, phenanthrene[3,2-b]benzofuran, benzothiophene, azir-benzothiophene, benzimidazole, azir-benzothiophene, benzobenzimidazole, azir-benzobenzimidazole, benzimidazole-derived carbene, azir-benzothiophene-derived carbene, carbazole, azir-carbazole, dibenzofuran, azir-dibenzofuran, dibenzothiophene, azir-dibenzothiophene, fluorene, dibenzosilfluorene, or azir-dibenzosilfluorene.

[0188] In some embodiments, the D group is dibenzofuran. In some embodiments, the D group is azir-dibenzofuran. In some embodiments, the D group is fluorene. In some embodiments, the D group is dibenzosilylfluorene.

[0189] In some embodiments, the D group is further cyclized by a D' group, wherein the D' group 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. In some embodiments, each ring of the monocyclic or polycyclic fused ring system of the D' group is a 5- or 6-membered carbon ring or heterocyclic ring. In some embodiments, each ring of the monocyclic or polycyclic fused ring system of the D' group is a 5- or 6-membered aryl or heteroaryl ring.

[0190] In some embodiments, the D' group is selected from the group consisting of the list of cyclic groups defined herein.

[0191] In some embodiments, the D' group is a monocyclic ring. In some embodiments, the D' group is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0192] In some embodiments, the D' group is benzene, pyridine, or oxazole. In some embodiments, the D' group is benzene. In some embodiments, the D' group is pyridine. In some embodiments, the D' group is oxazole.

[0193] In some embodiments, the D group is dibenzofuran and the D' group is pyridine. In some embodiments, the D group is azir-dibenzofuran and the D' group is benzene.

[0194] In some embodiments, the D' group is a polycyclic fused ring system.

[0195] In some embodiments, the D' group is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiphene, aza-dibenzothiphene, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, dibenzosilfluorene, aza-dibenzosilfluorene, phenanthridine, fluorene, and aza-fluorene.

[0196] In some embodiments, the D' group is naphthalene, quinoline, benzofuran, aza-benzofuran, benzothiophene, aza-benzothiophene, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, or aza-dibenzosilylfluorene. In some embodiments, the D' group is naphthalene. In some embodiments, the D' group is benzofuran.

[0197] In some embodiments, the D group is dibenzofuran and the D' group is naphthalene or benzofuran. In some embodiments, the D group is azir-dibenzofuran and the D' group is naphthalene.

[0198] In some embodiments, the B group and the D group are each a polycyclic fused ring system.

[0199] In some embodiments, the A group and the C group are monocyclic or polycyclic rings having exactly two fused rings.

[0200] In some embodiments, the B group is a polycyclic fused ring system comprising at least three fused rings. In some embodiments, the B group is a polycyclic fused ring system comprising at least four fused rings. In some embodiments, the B group is a polycyclic fused ring system comprising at least five fused rings.

[0201] In some embodiments, the D group is a polycyclic fused ring system comprising at least three fused rings. In some embodiments, the D group is a polycyclic fused ring system comprising at least four fused rings. In some embodiments, the D group is a polycyclic fused ring system comprising at least five fused rings.

[0202] In some embodiments, at least one of group A, group B, group C, or group D may be an independent polycyclic fused ring structure. In some embodiments, at least one of group A, group B, group C, or group D 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 coordinated with a metal. In some embodiments, the polycyclic fused ring structure has two 6-membered rings. In some embodiments, at least one of group A, group B, group C, or group D may be independently selected from the group consisting of benzofuran, benzothiophene, benzoselenene, naphthalene, and their nitrogen heteromorphs.

[0203] In some embodiments, at least one of group A, group B, group C, or group D 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 with a ring coordinated to metal M, and the second 6-membered ring is fused with the 5-membered ring. In some embodiments, at least one of group A, group B, group C, or group D may independently be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenene, and their nitrogen heteromorphs. In some such embodiments, at least one of group A, group B, group C, or group D may independently be further substituted at the ortho or meta position of an O, S, or Se atom by a substituent selected from the group consisting of deuterium, fluorine, nitriles, 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 O, S, or Se) and a substituent at the 7-position (meta to O, S, or Se).

[0204] In some embodiments, at least one of group A, group B, group C, or group D 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 with a ring coordinated to metal M, the second 6-membered ring is fused with the 5-membered ring, and the third 6-membered ring is fused with 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, nitriles, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0205] In some embodiments, at least one of group A, group B, group C, or group D may independently be a polycyclic fused ring structure comprising at least five fused rings. In some embodiments, the polycyclic fused ring structure comprises four 6-membered rings and one 5-membered ring, or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments having one 5-membered ring, the 5-membered ring is fused with a ring coordinated to metal M, a second 6-membered ring is fused with the 5-membered ring, a third 6-membered ring is fused with the second 6-membered ring, and a fourth 6-membered ring is fused with the third 6-membered ring.

[0206] In some embodiments, at least one of the groups A, B, C, or D can independently be the aziridine form of the polycyclic fused ring described above. In some such embodiments, at least one of the groups A, B, C, or D can independently contain exactly one aziridine N atom. In some such embodiments, at least one of the groups A, B, C, or D contains exactly two aziridine N atoms, which may be in one ring or in two different rings. In some such embodiments, the ring having the aziridine N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring having the aziridine N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each of the adjacent positions of the aziridine N atom is substituted.

[0207] In some embodiments, Z 1 It is N, Z 2 It's C, Z 3 It is C, and Z 4 It's C.

[0208] In some embodiments, Z 1 It is carbene carbon, Z 2 It is N, Z 3 It is C, and Z 4 It's C.

[0209] In some embodiments, Z 1 and Z 4 All are N.

[0210] In some embodiments, Z 2 and Z 3 Both are C.

[0211] In some embodiments, Z 2 or Z 3 At least one of them is N. In some embodiments, Z 2 It is N. In some embodiments, Z 3 It is N.

[0212] In some embodiments, Z 5 It is N, Z 6 It's C, Z 7 It is C, and Z 8 It's C.

[0213] In some embodiments, Z 5 It is carbene carbon, Z 6 It is N, Z 7 It is C, and Z 8 It is N.

[0214] In some embodiments, Z 5 and Z 8 All are N.

[0215] In some embodiments, Z 6 and Z 7 Both are C.

[0216] In some embodiments, Z 6 or Z 7 At least one of them is N. In some embodiments, Z 6 It is N. In some embodiments, Z 7 It is N.

[0217] In some embodiments, K 1 It is a direct key.

[0218] In some embodiments, K 1 It is O, S, or Se. In some embodiments, K 1 It is O.

[0219] In some embodiments, K 1 Choose freely N(R) α ), P(R α ) and B(R α A group consisting of ).

[0220] In some embodiments, K 1 Choose freely C(R) α (R) β ) and Si(R α (R) β A group consisting of ).

[0221] In some embodiments, K 2 It is a direct key.

[0222] In some embodiments, K 2 It is O, S, or Se. In some embodiments, K 2 It is O.

[0223] In some embodiments, K 2Choose freely N(R) α ), P(R α ) and B(R α A group consisting of ).

[0224] In some embodiments, K 2 Choose freely C(R) α (R) β ) and Si(R α (R) β A group consisting of ).

[0225] In some embodiments, K 1 and K 2 They are all direct keys.

[0226] In some embodiments, L 1 It is a direct key.

[0227] In some embodiments, L 1 It is O, S, or Se.

[0228] In some embodiments, L 1 It is BR, NR, or PR. In some embodiments, L 1 It is NR.

[0229] In some embodiments, L 1 It is P(O)R, C=O, C=S, C=Se, C=NR', C=CRR', S=O or SO2.

[0230] In some embodiments, L 1 It is BRR', CRR', SiRR', or GeRR'.

[0231] In some embodiments, L 1 It's CR.

[0232] In some embodiments, L 2 It is a direct key.

[0233] In some embodiments, L 2 It is O, S, or Se.

[0234] In some embodiments, L 2 It is BR, NR, or PR. In some embodiments, L 2 It is NR.

[0235] In some embodiments, L 2 It is P(O)R, C=O, C=S, C=Se, C=NR', C=CRR', S=O or SO2.

[0236] In some embodiments, L 2It is BRR', CRR', SiRR', or GeRR'.

[0237] In some embodiments, L 2 It's CR.

[0238] In some embodiments, L 1 and L 2 They are all direct keys.

[0239] In some embodiments, the OLED compound comprises an electron-withdrawing group. In some embodiments, the Hammett constant of the electron-withdrawing group is greater than 0. In some embodiments, the Hammett constant of the electron-withdrawing group is equal to or greater than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.

[0240] In some embodiments, the first ligand L A 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 k2 Substituted 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, ketones, carboxylic acids, esters, nitriles, isonitriles, sulfinyl groups, sulfonyl groups, partially and fully fluorinated alkyl groups, partially and fully fluorinated aryl groups, partially and fully fluorinated heteroaryl groups, cyano-containing alkyl groups, cyano-containing aryl groups, cyano-containing heteroaryl groups, isocyanates, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0241] Each R k1 Indicates single substitution up to the maximum permissible substitution or no substitution;

[0242] Where Y G Choose from the following groups: 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

[0243] Where R k1 R k2 R k3 R e and R fEach of them is independently hydrogen or a substituent selected from the group of universal substituents defined herein.

[0244] In some embodiments, the first ligand L A Electron-withdrawing groups comprising structures selected from the following EWG2 list: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0245] In some embodiments, the first ligand L AElectron-withdrawing groups comprising structures selected from the following EWG3 list: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0246] In some embodiments, the first ligand L A Electron-withdrawing groups comprising structures selected from the following EWG4 list: , , , , , , , , , , , , , , , , , , , , , , , and .

[0247] In some embodiments, the first ligand L A Electron-withdrawing groups containing π-electron-deficient components are selected from the group consisting of structures listed in the following π-EWG list: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC. + N(R k2 3. BR k2 R k3 Substituted or unsubstituted 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, ketones, carboxylic acids, esters, nitriles, isonitriles, sulfinyl groups, sulfonyl groups, partially and fully fluorinated aryl groups, partially and fully fluorinated heteroaryl groups, cyano-containing aryl groups, cyano-containing heteroaryl groups, isocyanates, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and The variables are the same as those previously defined.

[0248] In some embodiments, the OLED compound comprises an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, the OLED compound comprises an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, the OLED compound comprises an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, the OLED compound comprises an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, the OLED compound comprises an electron-withdrawing group from the π-EWG list as defined herein.

[0249] In some embodiments, 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 electron-withdrawing groups from the list of π-EWG as defined herein.

[0250] In some embodiments, 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 B It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R BIt is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0251] In some embodiments, ligand L B It includes electron-withdrawing groups from the EWG1 list as defined herein. In some embodiments, ligand L B It contains electron-withdrawing groups from the EWG2 list as defined herein. In some embodiments, the ligand L B It contains electron-withdrawing groups from the EWG3 list as defined herein. In some embodiments, the ligand L B It contains electron-withdrawing groups from the EWG4 list as defined herein. In some embodiments, the ligand L B It includes electron-withdrawing groups from the list of π-EWG as defined herein.

[0252] In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R C It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0253] In some embodiments, at least one R D It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R D It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R D It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R D It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R D It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0254] In some embodiments, at least one R or R' is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R or R' is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R or R' is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R or R' is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R or R' is or contains an electron-withdrawing group from the π-EWG list as defined herein.

[0255] In some embodiments, at least one R α Or R β It is or contains an electron-withdrawing group 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 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 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 from the EWG4 list as defined herein. In some embodiments, at least one R α Or R β It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0256] In some embodiments, at least one R A It's not hydrogen.

[0257] In some embodiments, 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.

[0258] In some embodiments, at least one R A It includes substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0259] In some embodiments, at least one R A It contains electron-withdrawing groups.

[0260] In some embodiments, at least one R AIncludes electron-withdrawing groups selected from the group consisting of the EWG1 list as defined herein.

[0261] In some embodiments, at least one R A Included III The structure;

[0262] Ring F' is a 5- to 10-membered carbon ring or heterocyclic ring;

[0263] Where R F' Indicates monosubstituted to trisubstituted or unsubstituted;

[0264] Each R 1' R 2' and R F' 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; and

[0265] Where R 1' Or R 2' At least one of them is not hydrogen or deuterium.

[0266] In some embodiments, ring F' is a 5- or 6-membered carbon ring or a heterocyclic ring. In some embodiments, ring F' is a 5- or 6-membered aryl or heteroaryl ring.

[0267] In some embodiments, R 1' and R 2' Neither of them are hydrogen or deuterium.

[0268] In some embodiments, R 1' and R 2' Each of them is independently selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof.

[0269] In some embodiments, R 1' and R 2' They are the same. In some embodiments, R 1' and R 2' They are different.

[0270] In some embodiments, R 1' and R 2' Each of them contains at least one carbon atom. In some embodiments, R 1' and R 2' Each of them contains at least two carbon atoms. In some embodiments, R 1' and R2' Each of them contains at least three carbon atoms. In some embodiments, R 1' and R 2' Each of them contains at least four carbon atoms. In some embodiments, R 1' and R 2' Each of them contains at least five carbon atoms.

[0271] In some embodiments, at least one R F' It is neither hydrogen nor deuterium.

[0272] In some embodiments, at least one R F' Choose from the following groups: alkyl, cycloalkyl, aryl, heteroaryl, silalkyl, germanalkyl, and combinations thereof.

[0273] In some embodiments, ring F' is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0274] In some embodiments, at least one R A Included IIIA The structure, where X 1a X 2a and X 3a Each of them is either C or N.

[0275] In some embodiments, 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 electron-withdrawing groups from the list of π-EWG as defined herein.

[0276] In some embodiments, at least one R 1' It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 1' It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 1' It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R1' It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 1' It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0277] In some embodiments, at least one R 2' It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R 2' It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R 2' It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R 2' It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R 2' It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0278] In some embodiments, with X 2a R of the bond F' The group selected is free from alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof. In some embodiments, X 2a R of the bond F' It is an alkyl group. In some embodiments, it is related to X. 2a R of the bond F' It is aryl or heteroaryl. In some embodiments, it is related to X. 2a R of the bond F' It is silane. In some embodiments, with X 2a R of the bond F' It is a germanyl group.

[0279] In some embodiments, X 1a X 2a and X 3a Each of them is C.

[0280] In some embodiments, X 1a X 2a or X 3a At least one of them is N. In some embodiments, X 1a X 2a or X 3a One of them is N.

[0281] In some embodiments, R F' It is an aryl group.

[0282] In some embodiments, R F' It is benzene.

[0283] In some embodiments, at least one R having a structure of formula III or formula IIIA A Select the group consisting of the structures in List A below:

[0284] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and As used in this article, the symbol H(D) or (D)H indicates that the substituent can be H or D.

[0285] In some embodiments, two R A They are joined or fused together to form a ring.

[0286] In some embodiments, at least one R B It's not hydrogen.

[0287] In some embodiments, 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.

[0288] In some embodiments, at least one R B It includes substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0289] In some embodiments, at least one R B It contains electron-withdrawing groups.

[0290] In some embodiments, at least one R BIncludes electron-withdrawing groups selected from the group consisting of the EWG1 list as defined herein.

[0291] In some embodiments, two R B They are joined or fused together to form a ring.

[0292] In some embodiments, at least one R C It's not hydrogen.

[0293] In some embodiments, at least one R C It contains at least one carbon atom. In some embodiments, at least one R C It contains at least two carbon atoms. In some embodiments, at least one R C It contains at least three carbon atoms. In some embodiments, at least one R C It contains at least four carbon atoms.

[0294] In some embodiments, at least one R C It includes substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0295] In some embodiments, at least one R C It contains electron-withdrawing groups.

[0296] In some embodiments, at least one R C Includes electron-withdrawing groups selected from the group consisting of the EWG1 list as defined herein.

[0297] In some embodiments, at least one R C Included III Structure:

[0298] Ring F' is a 5- to 10-membered carbon ring or heterocyclic ring;

[0299] Where R F' Indicates monosubstituted to trisubstituted or unsubstituted;

[0300] Each R 1' R 2' and R F' 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; and

[0301] Where R 1' Or R 2' At least one of them is not hydrogen or deuterium.

[0302] In some embodiments, ring F' is a 5- or 6-membered carbon ring or a heterocyclic ring. In some embodiments, ring F' is a 5- or 6-membered aryl or heteroaryl ring.

[0303] In some embodiments, R 1' and R 2' Neither of them are hydrogen or deuterium.

[0304] In some embodiments, R 1' and R 2' Neither of them are hydrogen or deuterium.

[0305] In some embodiments, R 1' and R 2' Each of them is independently selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof.

[0306] In some embodiments, R 1' and R 2' They are the same. In some embodiments, R 1' and R 2' They are different.

[0307] In some embodiments, R 1' and R 2' Each of them contains at least one carbon atom. In some embodiments, R 1' and R 2' Each of them contains at least two carbon atoms. In some embodiments, R 1' and R 2' Each of them contains at least three carbon atoms. In some embodiments, R 1' and R 2' Each of them contains at least four carbon atoms. In some embodiments, R 1' and R 2' Each of them contains at least five carbon atoms.

[0308] In some embodiments, at least one R F' It is neither hydrogen nor deuterium.

[0309] In some embodiments, at least one R F' Choose from the following groups: alkyl, cycloalkyl, aryl, heteroaryl, silalkyl, germanalkyl, and combinations thereof.

[0310] In some embodiments, ring F' is selected from the group consisting of: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.

[0311] In some embodiments, at least one RC Included IIIA The structure, where X 1a X 2a and X 3a Each of them is either C or N.

[0312] In some embodiments, with X 2a R of the bond F' The group selected is free from alkyl, cycloalkyl, aryl, heteroaryl, silyl, germanyl, and combinations thereof. In some embodiments, X 2a R of the bond F' It is an alkyl group. In some embodiments, it is related to X. 2a R of the bond F' It is aryl or heteroaryl. In some embodiments, it is related to X. 2a R of the bond F' It is silane. In some embodiments, with X 2a R of the bond F' It is a germanyl group.

[0313] In some embodiments, X 1a X 2a and X 3a Each of them is C.

[0314] In some embodiments, X 1a X 2a or X 3a At least one of them is N. In some embodiments, X 1a X 2a or X 3a One of them is N.

[0315] In some embodiments, R F' It is an aryl group.

[0316] In some embodiments, R F' It is benzene.

[0317] In some embodiments, at least one R having a structure of formula III or formula IIIA C Choose a group consisting of structures as defined in List A in this document.

[0318] In some embodiments, at least one R D It's not hydrogen.

[0319] In some embodiments, at least one R D It contains at least one carbon atom. In some embodiments, at least one R D It contains at least two carbon atoms. In some embodiments, at least one R DIt contains at least three carbon atoms. In some embodiments, at least one R D It contains at least four carbon atoms.

[0320] In some embodiments, at least one R D It includes substituents selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0321] In some embodiments, at least one R D It contains electron-withdrawing groups.

[0322] In some embodiments, at least one R D Includes electron-withdrawing groups selected from the group consisting of the EWG1 list as defined herein.

[0323] In some embodiments, two R D They are joined or fused together to form a ring.

[0324] In some embodiments, at least one of R or R' is not hydrogen.

[0325] In some embodiments, at least one of R or R' contains at least one carbon atom. In some embodiments, at least one of R or R' contains at least two carbon atoms. In some embodiments, at least one of R or R' contains at least three carbon atoms. In some embodiments, at least one of R or R' contains at least four carbon atoms.

[0326] In some embodiments, at least one of R or R' comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0327] In some embodiments, at least one of R or R' contains an electron-withdrawing group.

[0328] In some embodiments, at least one of R or R' contains an electron-withdrawing group selected from the group consisting of the EWG1 list as defined herein.

[0329] In some embodiments, R and R' are joined or fused together to form a ring.

[0330] In some embodiments, R α Or R β At least one of them is not hydrogen.

[0331] In some embodiments, 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, Rα 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.

[0332] In some embodiments, 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.

[0333] In some embodiments, R α Or R β At least one of them contains an electron-withdrawing group.

[0334] In some embodiments, R α Or R β At least one of them contains an electron-withdrawing group selected from the group consisting of the EWG1 list as defined herein.

[0335] In some embodiments, R α and R β They are joined or fused together to form a ring.

[0336] In some embodiments, ligand L A Select the group consisting of the structures listed in List 1 below:

[0337] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0338] in:

[0339] X1 to X 19 Each of them is either carbon or nitrogen;

[0340] Y A Y B and Y C Each of the following groups is selected independently: BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO2,C=CR e R f C=NR e CR e R f P(O)R e SiR e R f and GeR e R f ;

[0341] R A1 R B1 R B2 and R B3 Each of these terms independently represents a single substitution up to the maximum possible number of substitutions or no substitutions;

[0342] R A1 R B1 R B2 R B3 Re and R f Each of them is independently hydrogen or a substituent selected from the group of universal substituents defined herein; and

[0343] Any two adjacent substituents can fused or joined to form a ring or a polydentate ligand.

[0344] In ligand L A In some embodiments selected from Listing 1, at least one R A1 R B1 R B2 Or R B3 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A1 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B1 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B2 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B3 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 Choose from the group of preferred general substituents as defined herein.

[0345] In ligand L A In some embodiments selected from Listing 1, X8 is C and connected to the top N-ring. In some embodiments, X9 is C and connected to the top N-ring. In some embodiments, X 10 It is C and connected to the top N-ring. In some embodiments, X 11 It is C and connected to the top N-ring. In some embodiments, Y B and Y C Each of them is an O.

[0346] In ligand L A In some embodiments selected from Listing 1, two R A1 The rings are joined to form a fused ring. In some such embodiments, the fused ring may be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbenes, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, or triazole. In some such embodiments, the fused ring may be benzene.

[0347] In ligand L A Selected from some embodiments in Listing 1, Y A It can be NR And R It is or contains a structure of Formula III or Formula IIIA as defined herein. In such embodiments, all those embodiments related to Formula III and / or Formula IIIA may be applied equivalently herein. In some embodiments, R Selected from List A as defined in this article.

[0348] In ligand L A In some embodiments selected from Listing 1, at least one R A1 R B1 R B2 Or R B3 It is partially or fully deuterated. In some embodiments, at least one R A1 It is partially or fully deuterated. In some embodiments, at least one R B1 It is partially or fully deuterated. In some embodiments, at least one R B2 It is partially or fully deuterated. In some embodiments, at least one R B3 It is partially or completely deuterated.

[0349] In ligand L A In some embodiments selected from Listing 1, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0350] In some embodiments,

[0351] ligand L ASelect the group consisting of the structures listed in List 2 below:

[0352] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , and ;

[0353] in:

[0354] Y A Y B and Y C Each of the following groups is selected independently: BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO2,C=CR e R f C=NR e CR e R f P(O)R e SiR e R f and GeR e R f ;

[0355] R A1 R B1 R B2 and R B3 Each of these terms independently represents a single substitution up to the maximum possible number of substitutions or no substitutions;

[0356] Each R A1 R B1 R B2 R B3 R e and R f Independently, it is hydrogen or a substituent selected from the group of universal substituents as defined herein; and

[0357] The two substituents may optionally join or fuse to form a ring.

[0358] In ligand L AIn some embodiments selected from Listing 2, at least one R A1 R B1 R B2 Or R B3 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A1 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B1 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B2 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B3 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 Choose from the group of preferred general substituents as defined herein.

[0359] In ligand L A Selected from some embodiments in Listing 2, two R A1 The ring is joined to form a fused ring. In some such embodiments, the fused ring may be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole-derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, or triazole. In some such embodiments, the fused ring may be benzene. In some embodiments, Y B and Y C Each of them is an O.

[0360] In ligand L A Selected from some embodiments in Listing 2, Y A It can be NR And R It is or contains a structure of formula III or formula IIIA. In such embodiments, all those formulas III and / or IIIA may be applied equivalently herein. In some embodiments, R Selected from List A as defined in this article.

[0361] In ligand L A In some embodiments selected from Listing 2, at least one R A1 R B1 R B2 Or R B3 It is partially or fully deuterated. In some embodiments, at least one R A1 It is partially or fully deuterated. In some embodiments, at least one R B1 It is partially or fully deuterated. In some embodiments, at least one R B2It is partially or fully deuterated. In some embodiments, at least one R B3 It is partially or completely deuterated.

[0362] In ligand L A In some embodiments selected from Listing 2, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A1 R B1 R B2 Or R B3 It is or contains electron-withdrawing groups from the list of π-EWG as defined herein.

[0363] In some embodiments, ligand L A Selected from L Ai (Rm)(Rn)(Ro)(Rp), where i is an integer from 1 to 148, and each Rm, Rn, Ro, and Rp is independently selected from a group consisting of R1 to R120; where L A1 (R1)(R1)(R1)(R1) to L A148 Each of (R120) is defined in the following Listing 3:

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381] Each of R1 to R120 has the structure defined in Listing B: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , and .

[0382] In some embodiments, L B It is either substituted or unsubstituted phenylpyridine.

[0383] In some embodiments, L B Select the group consisting of the structures in List 4 below:

[0384] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0385] in:

[0386] T can be freely selected from the following groups: B, Al, Ga, and In;

[0387] K 1' Choose from the following groups: single bond, O, S, NR e PRe BR e CR e R f and SiR e R f ;

[0388] Y 1 To Y 13 Each of them is independently selected from the group consisting of C and N;

[0389] Y' selects from the following groups: 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 ;

[0390] R e and R f They can be fused or joined to form rings;

[0391] Each R a R b R c and R d Independently represents single substitution up to the maximum permissible number of substitutions or no substitution;

[0392] 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, halogroup, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and

[0393] R a1 Rb1 R c1 R d1 R a R b R c and R d Any two substituents can fused or joined to form a ring or a polydentate ligand.

[0394] In some embodiments, L B Select independently the groups consisting of the structures in the following list 5:

[0395] : , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0396] in:

[0397] R a '、R b '、R c '、R d 'and R eEach can be used independently to indicate zero substitution, single substitution, or at most a maximum permissible number of substitutions to its associated ring;

[0398] R a '、R b '、R c '、R d 'and R e Each of these substituents is independently hydrogen or selected from the group consisting of: deuterium, halogroup, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, selenyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and

[0399] R a '、R b '、R c '、R d 'and R e The two substituents in ' can fused or joined to form a ring or a polydentate ligand.

[0400] In some embodiments, L B Include The structure is such that the variables are the same as previously defined. In some embodiments, Y 1a To Y 4a Each of them is independently carbon. In some embodiments, Y 1a To Y 4a At least one of them is N. In some embodiments, Y 1a To Y 4a One of them is N. In some embodiments, Y 1a It is N. In some embodiments, Y 2a It is N. In some embodiments, Y 3a It is N. In some embodiments, Y 4a It is N. In some embodiments, 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.

[0401] In some embodiments, Y 1a It is carbon and is connected to R a1 In some such embodiments, R a1 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R a1 The group of preferred general substituents as defined herein can be selected. In some such embodiments, R a1 It is a tertiary alkyl, silyl, or germanyl group. In some such embodiments, Ra1 It is a tertiary alkyl group. In some embodiments, Y 2a It is carbon and is connected to R a2 In some such embodiments, R a2 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R a2 The group of preferred general substituents as defined herein can be selected. 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 embodiments, R a3 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R a3 The group of preferred general substituents as defined herein can be selected. 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 embodiments, R a4 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R a4 The group of preferred general substituents as defined herein can be selected. 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.

[0402] In some embodiments, Y 3a It is C and R connected to it. a It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, Y 2a It is C and R connected to it a It is a tertiary alkyl, silyl, or germanyl group.

[0403] In some embodiments, Y 1a To Y 3a It is C, Y 4a It is N, and with Y 3a Connected R a3 It is a tertiary alkyl, silyl, or germanyl group. In some embodiments, Y 1a To Y 3a It is C, Y 4a It is N, and with Y 2a Connected R a2 It is a tertiary alkyl, silyl, or germanyl group.

[0404] In some embodiments, 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 embodiments, at least one pair of R a A pair of R b Or an R a And an R b Joining or fused into rings.

[0405] In some embodiments, R b1 Linked to C1 (carbon atom). In some such embodiments, R b1 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R b1 The group of preferred general substituents as defined herein can be selected. 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 embodiments, R b2 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R b2 The group of preferred general substituents as defined herein can be selected. 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 Linked to C3 (carbon atom). In some such embodiments, R b3 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R b3 The group of preferred general substituents as defined herein can be selected. 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 Linked to C4 (carbon atom). In some such embodiments, R b4 The group consisting of any of the general substituents defined herein is optional. In some such embodiments, R b4 The group of preferred general substituents as defined herein can be selected. In some such embodiments, R b4It 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.

[0406] In some embodiments, L A Selected from L Ai (Rm)(Rn)(Ro)(Rp), where i is an integer from 1 to 148, and each Rm, Rn, Ro, and Rp is independently selected from a group consisting of R1 to R120; where L A1 (R1)(R1)(R1)(R1) to L A148 (R120)(R120)(R120)(R120) and L B Each of them is selected from L Bk Where k is an integer from 1 to 547, and:

[0407] The first compound has the formula Ir(L) Ai (Rm)(Rn)(Ro)(Rp))2(L Bk ), and the first compound is selected from Ir(L A1 (R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A148 (R120)(R120)(R120)(R120))2(L B547 A group consisting of )

[0408] Each L Bk It has a structure as defined in Listing 6 below:

[0409] , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , and .

[0410] In some embodiments, the first compound is selected from only L Bk The group consisting of compounds that correspond to one of the following: L B1 L B30 L B31 L B109 L B110 L B112 L B113 L B114 L B125 L B127 L B138 L B140 L B149 L B150 L B170 L B171 L B172 L B174 L B208 L B241 L B312 L B315 L B356 L 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 L B476 L B542 L B543 L B544 LB545 L B546 and L B547 .

[0411] In some embodiments, the first compound is selected from only L Bk The group consisting of compounds that correspond to one of the following: L B1 L B30 L B31 L B125 L B138 L B171 L B172 L B356 L B357 L B367 L B371 L B382 L B455 L B456 L B542 L B543 L B544 L B545 L B546 and L B547 .

[0412] In some embodiments, L A Select the group consisting of structures from List 1, List 2, or List 3, and L B Select the group consisting of structures from List 4, List 5, or List 6. In some embodiments, L A Select the group consisting of the structures in list 1, and L B Choose freely L Bk A group consisting of structures. In some embodiments, L A Select the group consisting of the structures in list 2, and L B Choose freely L Bk A group consisting of structures. In some embodiments, L A L selected from List 3 Ai (Rm)(Rn)(Ro)(Rp), and L B Choose freely L Bk The group consisting of structures, where k is an integer from 1 to 547, and the first compound of the OLED has the formula Ir(L Ai (Rm)(Rn)(Ro)(Rp))2(L Bk ), which is composed of Ir(L A1 (R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A148 (R120)(R120)(R120)(R120)2(L B547 The compound composition of ).

[0413] In some embodiments, the first compound is selected from the group consisting of the structures listed in List 7:

[0414] and ;

[0415] Where R AA R BB R CC R DD R EE R FF R GG and R HH Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0416] Each R AA R BB R CC R DD R EE R FF R GG and R HH 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and

[0417] Any two substituents may optionally join or fuse to form a ring.

[0418] In some embodiments, the first compound is selected from the group consisting of the structures listed in List 8:

[0419] , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , and .

[0420] In some embodiments of the OLED, the first compound is partially or fully deuterated.

[0421] In some embodiments, this disclosure also provides a formula Ir(L) A )2(L B Compounds of ). In some such embodiments, L A It can be selected from List 1, List 2 or List 3, and L B It can be selected from Listing 4, Listing 5, or Listing 6. In some such embodiments, when L A When selected from List 1 or List 2, an R A And an R B Bonding. In some such embodiments, the compound may have the formula Ir(L Ai (Rm)(Rn)(Ro)(Rp))2(L Bk ), which is composed of Ir(L A1 (R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A148 (R120)(R120)(R120)(R120)2(L B547 The first compound may be selected from the compounds listed in 8. In some such embodiments, the first compound may be selected from the compounds listed in 8.

[0422] In some embodiments of OLEDs, the formula Ir(L) described herein A )2(L B The first compound is partially or fully deuterated. In some embodiments, the formula Ir(L) described herein is... A )2(L BThe first compound is fully deuterated. In some embodiments of OLEDs, the formula Ir(L) described herein... A )2(L B The first 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 general meaning and includes the percentage of all possible hydrogen atoms (e.g., hydrogen or deuterium positions) occupied by deuterium atoms in the compound. In some embodiments, the carbon atoms constituting the ring coordinated to the metal M are fully or partially deuterated. In some embodiments, the carbon atoms contained in the polycyclic system coordinated to the metal M are fully or partially deuterated. In some embodiments, the substituents attached to the monocyclic or fused polycyclic system coordinated to the metal M are fully or partially deuterated.

[0423] In some embodiments of OLEDs, the emission of the first compound at room temperature has a full width at half maximum (FWHM) equal to or less than 50, 45, 40, 35, 30, 25, 20, 15, 10, or 5 nm. A narrower FWHM means better color purity for OLED display applications.

[0424] In the case of M(L) as defined above A )2(L B In some embodiments of the hybrid compounds for OLEDs, ligand L A Having the first substituent R I The first substituent R I The first atom aI in ligand L A Of all the atoms, the one furthest from the metal M is ligand L. B Having a second substituent R II The second substituent R II The first atom α-II in ligand L B Of all the atoms, it is the farthest from the metal M.

[0425] In such heterocoordination compounds for OLEDs, vector V D1 and V D2 It can be defined as follows. V D1 Let V represent the direction from metal M to the first atom aI, and let V be the vector. D1 The value of D 1 This indicates that metal M and the first substituent R I The straight-line distance between the first atoms aI in V. D2 This represents the direction from metal M to the first atom a-II, and the vector V D2 The value of D2 This indicates that metal M and the second substituent R II The straight-line distance between the first atom a-II in the matrix.

[0426] In such heterocoordination compounds for OLEDs, a sphere with radius r is defined, its center being a metal M, and radius r is a factor that allows the sphere to enclose non-substituent R in the compound. I and R II The minimum radius of all atoms in a portion; and where D 1 Or D 2 At least one of them is at least 1.5 Å larger than the radius r. In some embodiments, D 1 Or D 2 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 and D 2 Both 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.

[0427] In some embodiments of such heterocoordination compounds for OLEDs, the first compound has a transition dipole moment axis, and the transition dipole moment axis is perpendicular to the vector V. D1 and V D2 The angle between them is defined, where the transition dipole moment axis and the vector V are intersected. D1 and V D2 At least one angle between them is less than 40°. In some embodiments, the transition dipole moment axis and the vector V are... D1 and V D2 At least one angle between them is less than 30°, 20°, 15°, or 10°. In some embodiments, the transition dipole moment axis is related to the vector V. D1 and V D2 The angles between them are all less than 20°. In some embodiments, the transition dipole moment axis and the vector V are... D1 and V D2 The angles between them are all less than 15° or 10°.

[0428] In some embodiments of such heterocoordination compounds for OLEDs, the first compound has a vertical dipole ratio (VDR) of 0.33 or less. In some embodiments of such heterocoordination compounds, the first compound has a VDR of 0.30, 0.25, 0.20, or 0.15 or less.

[0429] 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.

[0430] In some embodiments of OLEDs, 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 homogeneous (each ligand is the same). In some embodiments, the compound may be mixed (at least one ligand is different from the others). In some embodiments, when more than one ligand coordinated to a metal is present, the ligands may all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, each ligand may be different from all the other ligands. This also holds true in embodiments where a ligand coordinated to a metal may be linked to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Therefore, in the case where the ligands are linked together, in some embodiments 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.

[0431] The M / T ratio is a descriptor of the "narrowness" of a peak. M is the area of ​​the main peak, defined as the wavelength of the maximum peak (λ). max The integral of the area over ±15 nm. T is the total area of ​​the spectrum, defined as the integral over the entire spectrum. A high M / T means the dopant has a narrow line shape.

[0432] VDR (Vertical Dipole Ratio) is the overall average fraction of vertically oriented molecular dipoles of the luminescent compound in the emitting thin film sample, where "vertical" orientation is relative to the plane of the substrate surface on which the thin film sample is formed (i.e., perpendicular to the substrate surface plane). A similar concept is the horizontal dipole ratio (HDR), which is the overall average fraction of horizontally oriented molecular dipoles of the luminescent compound in the emitting thin film sample, where "horizontal" orientation is relative to the plane of the substrate surface on which the thin film sample is formed (i.e., parallel to the substrate surface plane). By definition, VDR + HDR = 1. VDR can be measured using angle-dependent and polarization-dependent photoluminescence measurements. The VDR of the emitting layer of the thin film test sample can be determined by comparing the measured emission modes of the photoexcited thin film test sample with polarization-dependent models. For example, Figure 3 Modeled data for p-polarized emission is presented. Modeled p-polarized photoluminescence (PL) of emitters with different VDRs is plotted. The modeled PL peak is observed around a 45-degree angle, where the peak PL is larger when the emitter's VDR is higher.

[0433] To measure the VDR value of a thin film test sample, an acceptor compound or sensitizer compound (depending on whether the VDR of the acceptor compound or sensitizer compound is being measured) can be used as the sole emitter in the thin film, and a reference host compound A can be used as the host to form the thin film test sample. Preferably, the reference host compound A is... Thin-film test samples are formed by thermally evaporating an emitter compound and a host compound on a substrate. For example, the emitter compound and host compound can be co-evaporated. In some embodiments, the doping level of the emitter compound in the host can be from 0.1 wt.% to 50 wt.%. In some embodiments, for a blue emitter, the doping level of the emitter compound in the host can be from 3 wt.% to 20 wt.%. In some embodiments, for red and green emitters, the doping level of the emitter compound in the host can be from 1 wt.% to 15 wt.%. The thickness of the thermally evaporated thin-film test sample can be from 50 to 1000 Å.

[0434] The quarter-high full width (FWQM) is used to evaluate the overall lineshape of the emission spectrum and assess color purity. The FWQM is measured at one-quarter of its maximum value. A narrower FWQM (smaller) corresponds to higher color purity.

[0435] In some embodiments, L A molecular weight ratio L BThe molecular weight is approximately 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, or 250. In some such embodiments, L A The molecular weight can be greater than 245 and L B The molecular weight can be no less than 155. In some such embodiments, L A The molecular weight can be greater than 270 and L B The molecular weight can be no less than 245.

[0436] In some embodiments, L A molecular weight ratio L B The molecular weight is greater than at least one methyl group. In some embodiments, L A molecular weight ratio L B The molecular weight is greater than that of at least two methyl groups. In some embodiments, L A molecular weight ratio L B The molecular weight is greater than three methyl groups. In some embodiments, L A molecular weight ratio L B The molecular weight is greater than that of at least one phenyl group. In some embodiments, L A molecular weight ratio L B The molecular weight is greater than at least two phenyl groups. In some embodiments, L A molecular weight ratio L B Its molecular weight is greater than that of at least one methyl group and one phenyl group.

[0437] C. Other aspects of the OLED disclosed herein

[0438] As described herein, this disclosure provides an OLED device comprising a first organic layer containing compounds as disclosed in the foregoing sections of this disclosure.

[0439] In some embodiments, the OLED comprises: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having the formula Ir(L) as described herein. A )2(L B The first compound of ).

[0440] 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 compound as described herein may be an emission dopant or a non-emission dopant.

[0441] In some embodiments, the organic layer may further comprise a body, wherein the body comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacrylidine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, silane, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo and aza-(5,9-dioxa-13b-boronanaphtho[3,2,1-de]anthracene).

[0442] In some embodiments, the subject may be selected from a group consisting of the following subject group 1 structures:

[0443] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0444] in:

[0445] Each of J1 to J6 is independently either C or N;

[0446] L' is a direct bond or an organic linking group;

[0447] Each Y AA Y BB Y CC and Y DD Independently select from the following groups: non-existent bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0448] R A' R B' R C' R D' R E'R F' and R G' Each of these terms independently represents monosubstituted, at most maximum substituted, or unsubstituted.

[0449] Each R, R', R A' R B' R C' R D' R E' R F' and R G' Substituents are independently hydrogen or selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring;

[0450] Furthermore, where possible, each unsubstituted aromatic carbon atom can be replaced by one or more N atoms to form a nitrogen-substituted ring.

[0451] 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, arylene, heteroarylene, and combinations thereof.

[0452] 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 Independently, it is O, S, or SiRR', or more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is substituted with N to form a nitrogen heterocycle.

[0453] In some embodiments, 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:

[0454] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

[0455] The structural diagrams of MG1 through MG27 are shown below:

[0456] , , , , , , , , , , , , , , , , , , , , , , , , , , In the MGb structure shown above, the positions of two bonds in the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are marked with numbers for identification purposes.

[0457] In some embodiments, the subject can be any of its nitrogen-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the subject has the formula EGa-MGb-EGc and is selected from the group consisting of h1 to h112 as defined in the following list of subjects group 2, wherein each of MGb, EGa, and EGc is defined as follows:

[0458]

[0459] 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, which indicates their bond position in the MGb structure.

[0460] In some embodiments, the organic layer may further comprise a body, wherein the body comprises a metal complex.

[0461] In some embodiments, the emitter layer may comprise two bodies: a first body and a second body. In some embodiments, the first body is a hole transport body and the second body is an electron transport body. In some embodiments, the first body is a hole transport body and the second body is a bipolar body. In some embodiments, the first body is an electron transport body and the second body is a bipolar body. In some embodiments, the first body and the second body may form an excimer complex. In some embodiments, the emitter layer may comprise a third body. In some embodiments, the third body is selected from the group consisting of: an insulating body (wide bandgap body), a hole transport body, and an electron transport body. In some embodiments, the third body forms an excimer complex with one of the first body and the second body, or with both of the first body and the second body. In some embodiments, the emitter layer may comprise a fourth body. In some embodiments, the fourth body is selected from the group consisting of: an insulating body (wide bandgap body), a hole transport body, and an electron transport body. In some embodiments, the fourth body forms an excimer complex with one of the first body, the second body, and the third body, with two of the first body, the second body, and the third body, or with each of the first body, the second body, and the third body. In some embodiments, 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 embodiments, 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 model 6201B potentiostat, using anhydrous dimethylformamide (DMF) solvent and tetrabutylammonium hexafluorophosphate as the supporting electrolyte. Glassy carbon, platinum wire, and silver wire are used as the working electrode, counter electrode, and reference electrode, respectively. 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).

[0462] 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 fluorescence and / or delayed fluorescence 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 fluorescence material. In some embodiments, emission may be generated by any one or all of the sensitizer, receptor, and final emitter. In some embodiments, 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.

[0463] As used herein, phosphorescence generally refers to photon emission when the electron spin quantum number changes, that is, 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, fluorescent emitters generally refer to photon emission when the electron spin quantum number remains constant, 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. There are two types of delayed fluorescence: 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. Without being bound by theory, it is assumed 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 A TADF emitter is a compound or excitopolymer complex of electron transport compounds. 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 linking an electron donor group (such as an amino or carbazole derivative) and an electron acceptor group (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). Donor-acceptor excitopolymer 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.

[0464] 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.

[0465] In some embodiments, the compounds of the present invention described herein are phosphorescent materials.

[0466] 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).

[0467] 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.

[0468] 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-carbamate 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, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene, 5λ 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5-oxa-9λ 2-aza-13b-boronazona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacridine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, 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.

[0469] In another aspect, the OLED of this disclosure may also include an emitting region comprising a compound or a composition of said compounds as disclosed in the foregoing compound section of this disclosure. In some embodiments, the emitting region may comprise Ir(L) as described herein. A )2(L B The emission region comprises a compound or a composition of said compounds. In some embodiments, the emission region comprises one or more organic layers, wherein at least one of said one or more organic layers 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 said one or more organic layers is formed by an emission system having a figure of merit (FOM) equal to or greater than a value selected from the group consisting of: 2.50, 2.55, 2.60, 2.65, 2.70, 2.75, 2.80, 2.85, 2.90, 2.95, 3.00, 5.00, 10.0, 15.0, and 20.0. The definition of FOM 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 said one or more organic layers comprises a compound or a composition of said compounds as disclosed in Parts A and D of this disclosure.

[0470] In some embodiments, the OLED or emitting region comprising 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 comprises at least one pixel, wherein the at least one pixel comprises a first sub-pixel and a second sub-pixel. The first sub-pixel comprises a first OLED, which comprises a first emitting region. The second sub-pixel comprises a second OLED, which comprises 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 embodiments comprising the compound of the present invention, as well as various combinations and sub-combinations of various device features and embodiments comprising the compound of the present invention, as disclosed herein.

[0471] In some embodiments, 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 embodiments, 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 light emitted; and the second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum: 400-500 nm, 500-600 nm, or 600-700 nm. max2 The light emitted. In some embodiments, the first emitting region comprises (if more than one) a first number of emitting layers deposited on top of another; and the second emitting region comprises (if more than one) a second number of emitting layers deposited on top of another; and the first number is different from the second number. In some embodiments, both the first emitting region and the second emitting region comprise phosphorescent materials that may be the same or different. In some embodiments, the first emitting region comprises phosphorescent material, while the second emitting region comprises fluorescent material. In some embodiments, both the first emitting region and the second emitting region comprise fluorescent materials that may be the same or different.

[0472] 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; wherein each of the N sub-pixels includes an emitting region; wherein the total number of emitting regions within 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 at least one pixel includes an emitting region identical to the first emitting region. In some embodiments, a full-color pixel arrangement may have multiple pixels including 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, external coupling, and color filter.

[0473] 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 pixelation 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 the stacked OLED comprise a sensitizer and an acceptor having various sensitization device features and various embodiments of the compounds of the invention disclosed herein. For example, the first emitting region is included in a sensitization device while the second emitting region is not included in a sensitization device; in some cases, both the first and second emitting regions are included in a sensitization device.

[0474] In some embodiments, the OLED can emit light from at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99%, or 100% of 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 the emitter material has a total nonradiative decay rate constant and a total radiative decay rate constant due to the presence of the reinforcement layer. 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.

[0475] In some embodiments, the OLED further includes an external coupling layer. In some embodiments, the external coupling layer is disposed above the enhancement layer on the side opposite the organic emitting layer. The external 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 external coupling layer. Examples of intermediary layers may be dielectric materials, including organic, inorganic, perovskite, and oxide materials, and may include stacks and / or mixtures of these materials.

[0476] The enhancement layer alters the effective properties of the medium in which the emitter material resides, thereby causing any or all of the following: reduced emissivity, altered emission profile, changes in emission intensity with angle, altered emitter material stability, altered OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, anode side, or both sides, or placing the enhancement layer itself as a CGL, produces an OLED device that utilizes any of the aforementioned effects. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, the OLED according to this disclosure may also include any other functional layers commonly found in OLEDs.

[0477] In some embodiments, the reinforcing layer may comprise 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 comprise at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, or Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the reinforcing layer is configured as a planar layer. In other embodiments, the reinforcing layer is characterized by wavelengths arranged periodically, quasi-periodically, or randomly, or by subwavelengths arranged periodically, quasi-periodically, or randomly.

[0478] In some embodiments, the outer coupling layer has a wavelength or subwavelength characteristic of being arranged periodically, quasi-periodically, or randomly. In some embodiments, the outer coupling layer may be composed of a plurality of nanoparticles. In some embodiments, the outer coupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, the outer coupling layer can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the plurality of nanoparticles, changing the thickness of a reinforcing layer, or changing the material of a reinforcing layer. The plurality of nanoparticles of the device may be formed from at least one of the following: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stack or layer of one or more materials and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outer coupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the outer coupling layer is formed by photolithography.

[0479] In some embodiments of the plasmonic device, 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.

[0480] In another aspect, this disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise compounds or combinations of such compounds as disclosed in the foregoing compound section of this disclosure.

[0481] In some embodiments, a consumer product includes an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise Ir(L) as described herein. A )2(L B The first compound of ).

[0482] 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. When excitons relax through photoemission mechanisms, light is emitted. 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.

[0483] 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 blocking layer (EBL) 130, an emission layer (EML) 135, a hole blocking layer (HBL) 140, an electron transport layer (ETL) 145, an electron injection layer (EIL) 150, a protective layer 155, a cathode 160, and a blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by sequentially depositing the layers. The properties and functions of these various layers, as well as the example materials, are described in more detail in columns 6-10 of US 7,279,704, which is incorporated herein by reference.

[0484] Further examples of each of these layers are available. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, 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 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, comprising composite cathodes having a thin layer of metal (e.g., Mg:Ag) having an overlying transparent, conductive, sputtered ITO layer, are disclosed in their entirety in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. Theories and uses of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. Descriptions of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0485] 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. The device 200 can be fabricated by sequentially depositing these layers. Because the most common OLED configuration has a cathode disposed above the anode, and the device 200 has a cathode 215 disposed below the anode 230, the device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 can be used in the corresponding layers of the device 200. Figure 2 Provide an example of how some layers can be omitted from the structure of device 100.

[0486] Figure 1 and 2The simple layered structures described herein are provided by way of 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, can 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 can 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.

[0487] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) containing 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. By another example, OLEDs 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 deviate from... Figure 1 and 2 The simple layered structure described herein. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the tabletop structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the recessed structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0488] Unless otherwise specified, any of the layers in the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet printing (as described in U.S. Patent Nos. 6,013,982 and 6,087,196, which are incorporated herein by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Patent No. 6,337,102 by Forrest et al., which are incorporated herein by reference in their entirety), and deposition via organic vapor jet printing (OVJP, also known as organic vapor jet deposition (OVJD)) (as described in U.S. Patent No. 7,431,968, which is incorporated herein by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably performed in 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 patterning via mask deposition, photolithography, and cold soldering (as described in U.S. Patents 6,294,398 and 6,468,819, which are incorporated herein by reference in their entirety) and some of the methods associated with deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to suit a particular deposition method. For example, branched or unbranched substituents, preferably containing at least three carbons, such as alkyl and aryl groups, may be used in small molecules to enhance their solution handling ability. Substituents having 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Materials with asymmetric structures may have better solution handling ability than materials with symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the solution handling ability of small molecules.

[0489] The device manufactured according to embodiments of this disclosure may optionally further include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage caused by exposure to harmful substances in an environment including moisture, vapors, and / or gases. The barrier layer may be deposited above, below, or adjacent to a substrate or electrode, or above any other part of the device, including edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed using various 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. Inorganic or organic compounds, or both, may be incorporated into the barrier layer. Preferred barrier layers comprise multiple alternative layers of materials including: polymeric and nonpolymeric materials; organic and inorganic materials; or mixtures of polymeric and nonpolymeric materials, an example of which is described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entirety.

[0490] The apparatus manufactured according to embodiments of this disclosure can be incorporated into a wide variety of electronic component modules (or units), which can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include displays, lighting devices (such as discrete light source devices or lighting panels), etc., which can be utilized by end-user product manufacturers. The electronic component module may optionally include driving electronics and / or a power supply. The apparatus 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. A consumer product incorporating an OLED is disclosed, wherein the OLED includes compounds of this disclosure in its organic layer. The consumer product should include any type of product containing one or more light sources and / or one or more of some type of visual display. Examples of the consumer products described include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external 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 tiled displays, theater or stadium screens, phototherapy devices, and signage. Various control mechanisms, including passive and active matrices, can be used to control the devices manufactured according to this disclosure. Many of the devices are intended for use in temperature ranges comfortable for humans, such as 18°C ​​to 30°C, and more preferably at room temperature (20-25°C), but can be used outside this temperature range (e.g., -40°C to +80°C).

[0491] Further details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0492] 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 herein. More generally, organic devices such as organic transistors can utilize the materials and structures described herein.

[0493] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer including carbon nanotubes. In some embodiments, the OLED further comprises one or more quantum dots. Such quantum dots may be in the emission layer or in other functional layers, such as conversion layers.

[0494] 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.

[0495] D. Other materials used in OLEDs

[0496] 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 themselves in the EML, or in combination with a wide variety of other emitters, hosts, transport layers, barrier 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.

[0497] a) Conductive dopants:

[0498] 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 group 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.

[0499] b) HIL / HTL:

[0500] 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 semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylhexacarbonitrile; metal complexes; and crosslinkable compounds.

[0501] Examples of aromatic amine derivatives used for HIL or HTL include (but are not limited to) the following general structures:

[0502] , , , and .

[0503] Ar 1 To Ar 9 Each of these is selected from: the group consisting of, for example, aromatic cyclic compounds such as: benzene, biphenyl, biphenylene, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azulene; and the group consisting of, for example, aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzene The group consisting of benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanopyridine, benzothiophenopyridine, thiophenopyridine, benzoselenopyridine, and selelenopyridine; and the 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 may be unsubstituted or may be substituted with the general substituents described above, and any two substituents may be joined or fused into a ring.

[0504] In some embodiments, each Ar1 To Ar 9 Independently comprising groups selected from the following groups:

[0505] , , , , , and ;

[0506] 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.

[0507] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0508] 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.

[0509] In some embodiments, (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... + The minimum oxidation potential in solution with / Fc coupling is less than about 0.6 V.

[0510] In some embodiments, the HIL / HTL material is selected from the group consisting of: phthalocyanine and porphyrin compounds, starburst triarylamine, 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 (such as 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.

[0511] c) EBL:

[0512] 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 result in generally 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 area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy compared to one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO level of the compound used in the EBL is shallower than the HOMO level of one or more of the bodies in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional groups as those used in one of the bodies described below.

[0513] d) Main body:

[0514] 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.

[0515] Examples of metal complexes used as the host preferably have the following general formula:

[0516]

[0517] 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.

[0518] In some embodiments, the metal complex is:

[0519]

[0520] (ON) is a bidentate ligand of a metal that coordinates with O and N atoms.

[0521] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbaene ligand.

[0522] In some embodiments, the host compound contains at least one selected from the group consisting of, for example, aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azurite; and aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, and oxazole. Thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziisoxazole, benzothiazazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, acridine, phenazine, phenothiazine, phenothiazine, azira-dibenzothiophene, azira-dibenzofuran, azira-dibenzoselenophene, azira-carbazole, azira-indole-carbazole, azira-triphenylene, azira-tetraphenylene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronazonaphtho[3,2,1-de]anthracene; and groups 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 each group may be unsubstituted or may be substituted with general substituents as described herein or may be further fused.

[0523] In some embodiments, the host compound comprises at least one group selected from the group consisting of:

[0524] , , , , , , , , , , , , , , , , , , , ,and , where k is an integer from 0 to 20 or from 1 to 20. X 101 To X 108 Independently selected from C or N. Z 101 and Z 102 It is independently selected from C, N, O, or S.

[0525] 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, alkyl-based compounds, aryltriphenylene compounds, polyfused heteroaryl compounds, donor-acceptor molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., pvk), spirofluorene compounds, spirofluorene-carbazole Zrazole compounds, indolocarbazole, 5-membered electron-deficient heterocycles (e.g., triazoles, oxadiazoles), tetraphenylene 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, aza-carbazole / dibenzofuran / dibenzothiophene compounds, and high triplet state organometallic complexes (e.g., metal-carbaene complexes).

[0526] e) Emitter material in EML:

[0527] One or more emitter materials may be used in conjunction with the compounds or devices disclosed herein. The emitter materials may be emittant or non-emittent in current devices as described herein. 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.

[0528] In some embodiments, the emitter material has the formula M(L) 1 ) x (L2 ) y (L 3 ) z ;

[0529] Where L 1 L 2 and L 3 They can be the same or different;

[0530] Where x is 1, 2, or 3;

[0531] Where y is 0, 1, or 2;

[0532] Where z is 0, 1, or 2;

[0533] Where x+y+z is the oxidation state of the metal M;

[0534] Where L 1 Select the group consisting of structures from the following list of ligands:

[0535] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0536] Each L 2 and L 3 Independent freedom of choice The group consisting of structures in the ligand list; where:

[0537] M is selected from the following groups: Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag, and Cu;

[0538] T can be freely selected from the following groups: B, Al, Ga, and In;

[0539] K 1' It is a direct key or a selection of the following groups: NR e PR e , O, S and Se;

[0540] Each Y 1 To Y 15 Independently select groups composed of free carbon and nitrogen;

[0541] Y' selects from the following groups: 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 ;

[0542] 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;

[0543] 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 hydrogen or a substituent selected from the group of universal substituents as defined herein; and

[0544] Any two substituents can fused or joined to form a ring or a polydentate ligand.

[0545] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 1:

[0546] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0547] in

[0548] X 96 To X 99 Each of them is independently C or N;

[0549] Each Y 100 Independently select the group consisting of NR'', O, S, and Se;

[0550] R 10a R 20a R 30a R 40a and R 50a Each of these terms independently represents monosubstituted, at most maximum substituted, or unsubstituted.

[0551] R, R', R'', R 10a R 11a R 12a R 13a R 20a R 30a R 40a R 50a R60 R 70 R 97 R 98 and R 99 Each of them is independently hydrogen or a substituent selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring.

[0552] In some embodiments, the emitter material is selected from the group consisting of the following dopant group 2:

[0553] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0554] in:

[0555] Each Y 100 Independently select the group consisting of NR'', O, S, and Se;

[0556] L is independently selected from the following groups: 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;

[0557] X 100 and X 200 Each time it appears, select from the following groups: O, S, Se, NR'' and CR''R''';

[0558] Each R A'' R B'' R C'' R D'' R E'' and R F'' Independently represent monosubstituted, at most maximum substituted, or unsubstituted;

[0559] R, R', R'', R''', R A1' R A2' R A'' R B'' R C'' R D'' RE'' R F'' R G'' R H'' R I'' R J'' R K'' R L'' R M'' and R N'' Each of them is independently hydrogen or a substituent selected from the group of general substituents as defined herein; and any two substituents may join or fuse to form a ring.

[0560] 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.

[0561] 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.

[0562] In some embodiments of OLEDs, the delayed fluorescence material has the formula M(L 5 (L) 6 ), where M is Cu, Ag, or Au, L 5 and L 6 Different, and L 5 and L 6 Choose independently from the following groups:

[0563] , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0564] Where A 1 - A 9 Each is independently selected from C or N;

[0565] Each R P R Q and R U Independently represent monosubstituted, at most maximum substituted, or unsubstituted;

[0566] Each R P R P R U R SA R SB R RA R RB R RC R RD R RE and R RF Substituents are independently hydrogen or selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring.

[0567] In some embodiments of OLEDs, the delayed fluorescence material includes at least one donor group selected from the group consisting of:

[0568] , , , , , , , , , , , , , , , , , , , and ;

[0569] 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.

[0570] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a total of up to three carbon ring atoms, together with their substituents, may be replaced by N.

[0571] In some embodiments, the delayed fluorescence material comprises at least one acceptor group selected from the group consisting of: nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor group and donor group as described herein may be directly linked, via a conjugated linker group or a non-conjugated linker group (such as sp...). 3 (Carbon or silicon atoms) are linked together.

[0572] In some embodiments, the fluorescent material comprises at least one chemical group selected from the group consisting of:

[0573] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0574] Where Y F Y G Y H and Y I Each of the following groups can be independently selected: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2;

[0575] Where X F and X G Each group is independently selected from the groups composed of C and N.

[0576] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a total of up to three carbon ring atoms, together with their substituents, may be replaced by N.

[0577] f)HBL:

[0578] Hole blocking layers (HBLs) can be used to reduce the number of holes and / or excitons leaving the emitter layer. The presence of such blocking layers in a device can result in generally 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.

[0579] In some embodiments, the compounds used in HBL contain the same molecules or the same functional groups as those used in the main body described above.

[0580] In some embodiments, the compound used in HBL contains at least one of the following groups selected from the group consisting of:

[0581] , , , , 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.

[0582] g)ETL:

[0583] An electron transport layer (ETL) may comprise a material capable of transporting electrons. The ETL may be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used, provided it is typically used for electron transport.

[0584] In some embodiments, the compounds used in the ETL contain at least one of the following groups in their molecules:

[0585] , , , , , , , , , and fullerenes; where k is an integer from 1 to 20, X 101 To X 108 Selected from C or N; Z 101 Choose a group consisting of C, N, O, and S.

[0586] In some embodiments, the metal complexes used in the ETL contain, but are not limited to, the following general formula:

[0587]

[0588] 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 value from 1 to the maximum number of ligands that can be bonded to the metal.

[0589] In some embodiments, the ETL material is selected from the group consisting of: anthracene-benzimidazole compounds, azirtriene 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.

[0590] h) Charge Generation Layer (CGL)

[0591] In tandem or stacked OLEDs, the conduction layer (CGL) plays a fundamental role in performance. It consists of an n-doped layer and a p-doped layer, respectively, for injecting electrons and holes. Electrons and holes are supplied by 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; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials contain n- and p-conductive dopants used in the transport layer.

[0592] 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.

[0593] 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 instance, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. The claimed invention may therefore include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that various theories regarding why the invention works are not intended to be limiting.

[0594] E. Experimental Section

[0595] Synthesis of Compound 1 of the present invention and Comparative Compound 1

[0596]

[0597] 2,6-Dimethylpyridine (521.4 mg, 4.866 mmol, 2.0 equivalent) was added to a suspension of 1 (2.110 g, 2.555 mmol, 1.05 equivalent) and 2 (1.072 g, 2.433 mmol, 1.0 equivalent) in 2-ethoxyethanol (50 mL). The reaction mixture was degassed with nitrogen for 10 min and then heated at 120 °C for 48 h with stirring. The solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography. The purified products were separated and concentrated under reduced pressure to give comparative compound 1 (0.806 g) and compound 1 of the present invention (0.367 g).

[0598] Synthesis of Compound 2 of the present invention and Comparative Compound 2

[0599]

[0600] 2,6-Dimethylpyridine (656.3 mg, 6.124 mmol, 2.0 equivalent) was added to a suspension of 1 (3.031 g, 3.674 mmol, 1.2 equivalent) and 3 (1.300 g, 3.062 mmol, 1.0 equivalent) in 2-ethoxyethanol (100 mL). The reaction mixture was degassed with nitrogen for 10 min and then heated at 122 °C for 60 h with stirring. The solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography. The purified products were separated and concentrated under reduced pressure to give comparative compound 2 (0.97 g) and compound 2 of the present invention (0.24 g).

[0601] Synthesis of Compound 3 of the present invention and Comparative Compound 3

[0602]

[0603] The suspensions of compounds 4 (2.50 g, 3.03 mmol, 1.0 equivalent) and 5 (2.033 g, 6.06 mmol, 2.0 equivalent) in methanol (140 mL) were degassed with nitrogen for 10 min, and then heated at 65 °C for 96 h with stirring. The solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography. The purified products were separated and concentrated under reduced pressure to give comparative compound 3 (0.64 g) and compound 3 of the present invention (0.68 g).

[0604] Synthesis of Compound 4 of the present invention and Comparative Compound 4

[0605]

[0606] The suspensions of 6 (1.310 g, 1.605 mmol, 1.0 equivalent) and 7 (1.421 g, 2.730 mmol, 1.7 equivalent) in 100 mL of 2-ethoxyethanol were degassed with nitrogen for 10 min and then heated at 110 °C for 18 h with stirring. The solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography. The purified products were separated and concentrated under reduced pressure to give comparative compound 4 (45 mg) and compound 4 of the present invention (571 mg).

[0607] Synthesis of Compound 5 of the present invention and Comparative Compound 5

[0608]

[0609] 2,6-Dimethylpyridine (620.2 mg, 5.788 mmol, 2.0 equivalent) was added to a suspension of 8 (2.629 g, 3.183 mmol, 1.1 equivalent) and 9 (1.727 g, 2.894 mmol, 1.0 equivalent) in 2-ethoxyethanol (95 mL). The reaction mixture was degassed with nitrogen for 10 min and then heated at 120 °C for 18 h with stirring. The solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography. The purified products were separated and concentrated under reduced pressure to give comparative compound 5 (2.225 g) and compound 5 of the present invention (0.011 g).

[0610] Device Examples

[0611] Through high vacuum (<10) -7 All example devices were manufactured using thermal evaporation. The anode was 800 Å indium tin oxide (ITO). The cathode consisted of 10 Å Liq (lithium 8-hydroxyquinoline) and 1,000 Å Al. Immediately after fabrication, all devices were sealed in a nitrogen glove box (<1 ppm H₂O and O₂) with an epoxy-sealed glass lid, and a desiccant was incorporated into the packaging. The organic stack of the device example consists of the following components sequentially from the ITO surface: 100 Å LG101 (purchased from LG Chem) as the hole injection layer (HIL); 400 Å HTM as the hole transport layer (HTL); a 400 Å thick emitter layer (EML); 50 Å EBM as the electron blocking layer (EBL); an emitter layer containing a 6:4 ratio of H-host (H1):E-host (H2) and 5 wt% green emitter; 50 Å H2 as the hole blocking layer (HBL); and 300 Å Liq (lithium 8-hydroxyquinoline) doped with 35% ETM as the ETL. The device structure is shown in Table 1. The chemical structures of the device materials are shown below.

[0612] , , , , , , .

[0613] Table 1. Materials and Thickness of Device Layers

[0614]

[0615] During manufacturing, the testing setup was used to measure electroluminescence (EL) and current density-voltage-luminance (JVL). For this purpose, a 2-channel Keysight B2902A SMU was used at 10 mA / cm². 2The current density was applied to the sample and measured using a Photo Research PR735 spectroradiometer. Emissivity (W / str / cm²) from 380 nm to 1080 nm was collected. 2 The total integrated photon count was then performed. The device was then placed under a large-area silicon photodiode for JVL scanning. The device was operating at 10 mA / cm². 2 The integrated photon counting is used to convert the photodiode current into photon counts. The voltage is scanned from 0 to 200 mA / cm². 2 The voltage. External quantum efficiency (EQE) using the total integral photon counting computational device.

[0616] All device results are summarized in Table 2 below. The voltage, lifetime (LE), and EQE of compounds 1-5 of the present invention are reported as relative values, each normalized relative to the corresponding comparative compound (i.e., compound 1 of the present invention to comparative compound 1, compound 2 of the present invention to comparative compound 2, compound 3 of the present invention to comparative compound 3, compound 4 of the present invention to comparative compound 4, and compound 5 of the present invention to comparative compound 5).

[0617] Table 2. Device Performance Results

[0618]

[0619] Definition of M / T: The M / T ratio is a descriptor for the "narrowness" of the emission peak, where M represents the area of ​​the main peak, which is defined as the maximum peak wavelength (λ). max M / T is the integral of the area of ​​the spectrum within ±15 nm, while T is the total area of ​​the spectrum, which is defined as the integral of the entire spectrum. The higher the M / T, the narrower the peak.

[0620] As shown in Table 2, the compounds of the present invention exhibit higher LE and EQE than the comparative compounds. Furthermore, the compounds of the present invention demonstrate enhanced M / T values ​​relative to their comparative counterparts. Enhanced M / T is a key feature for achieving high color purity in phosphorescent emitters. Typically, phosphorescent metal complexes exhibit M / T values ​​of 0.35 to 0.5, and even an incremental improvement of 0.01 M / T can lead to significant improvements in OLED performance. The presence of two fused-ring ligands (emitting ligands) and a single auxiliary ligand in the compounds of the present invention results in improved M / T and a relative increase in EQE and LE, indicating that this feature is indispensable for the generation of high-performance phosphorescent emitters. Given the expectation that experimental errors would lead to variable performance, the improvements reported here exceed expectations and are considered significant and unexpected.

Claims

1. An organic light-emitting diode (OLED) comprising: anode; cathode; and An emitting layer disposed between the anode and the cathode; The emission layer includes the formula Ir(L) A )2(L B The first compound of ); Where L A Including I The structure, and L B Included II The structure; in: Groups A, B, C, and D 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. At least one of the B group or the D group is a polycyclic fused ring system; Z 1 To Z 8 Each can be either C or N independently; L 1 and L 2 Each of the following groups is independently selected: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CRR', S=O, SO2, CR, CRR', SiRR', and GeRR'; K 1 and K 2 Choose from the following groups: direct key, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R α (R) β ) and Si(R α (R) β ); R A R B R C and R D Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R, R', R α R β R A R B R C and R D 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; L A and L B They are different; Ir(L A The first triplet excited state energy of )3 is lower than that of Ir(L B The first triplet excited state energy of )3, or L A The molecular weight is greater than L B The molecular weight; and At least one of the following conditions is true: (1) Ir(L A )2(L B The photoluminescence spectrum of Ir(L) has an emission peak, which has a full width at half maximum (FWHM) (1); A (L) B The photoluminescence spectrum of )2 has an emission peak, which has a full width at half maximum (FWHM) (2); and FWHM (2) - FWHM (1) is equal to or greater than 2 nm; (2) Ir(L A (L) B )2 quarter-height full width aspect ratio Ir(L A )2(L B The height of the entire width is at least 5 nm; (3) Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of 2 is at least 0.01; (4) Ir(L A (L) B )2 of λ max Compared to Ir(L) A )2(L B ) of λ max Larger than 1 nm; (5) Ir(L A )2(L B The external quantum efficiency ratio of Ir(L) is higher than that of Ir(L). A (L) B The external quantum efficiency of 2 is at least 3% greater; (6) Ir(L A (L) B The vertical dipole ratio of )2 is equal to that of Ir(L) A )2(L B The vertical dipole ratio is at least 0.02 greater than that of the other two. (7) At 10 mA / cm 2 At that time, Ir(L A (L) B The voltage ratio of )2 to Ir(L) A )2(L B The voltage must be at least 0.05 V; or (8) The emission layer contains a fluorescent dopant.

2. The OLED according to claim 1, wherein group A is selected from the group consisting of the following cyclic groups: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenene, aza - benzo[selenophene], indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzo[benzimidazole], aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, naphthemidazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, aza-dibenzosilylfluorene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene; or The C group is selected from the following groups: benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenene, aza-benzoselenene, indene, aza- Indole, indole, aza-indole, benzimidazole, aza-benzimidazole, benzobenzimidazole, aza-benzimidazole, benzimidazole-derived carbenes, aza-benzimidazole-derived carbenes, carbazole, aza-carbazole, naphthemidazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilylfluorene, aza-dibenzosilylfluorene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.

3. The OLED according to claim 1, wherein the B group 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, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenene, aza-benzoselenene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzobenzimidazole Imidazole, aza-benzobenzimidazole, benzimidazole-derived carbene, aza-benzimidazole-derived carbene, carbazole, aza-carbazole, naphzimidazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene; and / or wherein the B group is further cyclized by a B' group, wherein the B' group 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.

4. The OLED according to claim 1, wherein the D group 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, benzofuran, aza-benzofuran, phenanthro[3,2-b]benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenene, aza-benzoselenene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzobenzimidazole Imidazole, aza-benzobenzimidazole, benzimidazole-derived carbene, aza-benzobenzimidazole-derived carbene, carbazole, aza-carbazole, naphzimidazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, dibenzosilfluorene, aza-dibenzosilfluorene, quinoxaline, phthalazine, phenanthrene, aza-phenanthrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene; and / or wherein the D group is further cyclized by a D' group, wherein the D' group 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.

5. The OLED according to claim 1, wherein the B group is a polycyclic fused ring system comprising at least three fused rings.

6. The OLED according to claim 1, wherein Z 1 It is N, Z 2 It's C, Z 3 It is C, and Z 4 It is C, or Z among them. 1 It is carbene carbon, Z 2 It is N, Z 3 It is C, and Z 4 It is C; and / or Z. 5 It is N, Z 6 It's C, Z 7 It is C, and Z 8 It is C, or Z among them. 5 It is carbene carbon, Z 6 It is N, Z 7 It is C, and Z 8 It is N; and / or where K is. 1 It is a direct bond, O or S; and / or where K is a direct bond. 2 It is a direct bond, O or S; and / or where L is a direct bond. 1 It is a direct bond; and / or where L is a direct bond. 2 It is a direct key.

7. The OLED according to claim 1, wherein at least one R A Or an R C Included III The structure; Ring F' is a 5- to 10-membered carbon ring or heterocyclic ring; Where R F' Indicates monosubstituted to trisubstituted or unsubstituted; Each R 1' R 2' and R F' 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; and Where R 1' Or R 2' At least one of them is not hydrogen or deuterium.

8. The OLED according to claim 1, wherein the ligand L A Select the group consisting of the structures listed in List 1 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; in: X1 to X4 and X8 to X 19 Each of them is either carbon or nitrogen; Y A Y B and Y C Each of the following groups is selected independently: BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO2,C=CR e R f C=NR e CR e R f P(O)R e SiR e R f and GeR e R f ; R A1 R B1 R B2 and R B3 Each of these terms independently represents a single substitution up to the maximum possible number of substitutions or no substitutions; R A1 R B1 R B2 R B3 R e and R f Each of them is independently hydrogen or a substituent selected from the group of universal substituents defined herein; and Any two adjacent substituents can fused or joined to form a ring or a polydentate ligand.

9. The OLED according to claim 1, wherein the ligand L A Select the group consisting of the structures listed in List 2 below: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , and ; in: Y A Y B and Y C Each of the following groups is selected independently: BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,S=O,SO2,C=CR e R f C=NR e CR e R f P(O)R e SiR e R f and GeR e R f ; R A1 R B1 R B2 and R B3 Each of these terms independently represents a single substitution up to the maximum possible number of substitutions or no substitutions; Each R A1 R B1 R B2 R B3 R e and R f Independently, it is hydrogen or a substituent selected from the group of universal substituents as defined herein; and The two substituents may optionally join or fuse to form a ring.

10. The OLED according to claim 1, wherein the ligand L A Selected from L Ai (Rm)(Rn)(Ro)(Rp), where i is an integer from 1 to 148, and each Rm, Rn, Ro, and Rp is independently selected from a group consisting of R1 to R120; where L A1 (R1)(R1)(R1)(R1) to L A148 Each of (R120) is defined as shown in Listing 3 below: Each of R1 to R120 has the structure defined in Listing B: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

11. The OLED according to claim 1, wherein L B Select the group consisting of the structures listed in List 4 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and , in: T can be freely selected from the following groups: B, Al, Ga, and In; K 1' Choose from the following groups: single bond, O, S, NR e PR e BR e CR e R f and SiR e R f ; Y 1 To Y 13 Each of them is independently selected from the group consisting of C and N; Y' selects from the following groups: BR e BR e R f NR e PR e P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f and GeR e R f ; R e and R f They can be fused or joined to form rings; Each R a R b R c and R d Independently represents single substitution up to the maximum permissible number of substitutions or no substitution; R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogroup, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, selenalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and R a1 R b1 R c1 R d1 R a R b R c and R d Any two substituents can fused or joined to form a ring or a polydentate ligand.

12. The OLED according to claim 1, wherein L A Selected from L Ai (Rm)(Rn)(Ro)(Rp), where i is an integer from 1 to 148, and each Rm, Rn, Ro, and Rp is independently selected from a group consisting of R1 to R120; where L A1 (R1)(R1)(R1)(R1) to L A148 (R120)(R120)(R120)(R120) and L B Each of them is selected from L Bk Where k is an integer from 1 to 547, and: The first compound has the formula Ir(L Ai (Rm)(Rn)(Ro)(Rp))2(L Bk ), and the first compound is selected from Ir(L A1 (R1)(R1)(R1)(R1))2(L B1 ) to Ir(L A148 (R120)(R120)(R120)(R120))2(L B547 A group consisting of ) and Each L Bk It has a structure as defined in Listing 6 below: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

13. The OLED of claim 1, wherein the first compound is selected from the group consisting of structures listed in List 8: 、 、 、 、 、 、 、 、 、 、 、 、 、、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

14. An organic light-emitting device (OLED) comprising: anode; cathode; and An emitting layer disposed between the anode and the cathode; The emission layer includes the formula Ir(L) A )2(L B The first compound of ); Where L A Including I The structure, and L B Included II The structure; in: Groups A, B, C, and D 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. At least one of the B group or the D group is a polycyclic fused ring system; Z 1 To Z 8 Each can be either C or N independently; L 1 and L 2 Each of the following groups is independently selected: direct bond, BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR', C=CRR', S=O, SO2, CR, CRR', SiRR', and GeRR'; K 1 and K 2 Choose from the following groups: direct key, O, S, Se, N(R) α ), P(R α ), B(R) α ), C(R α (R) β ) and Si(R α (R) β ); R A R B R C and R D Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R, R', R α R β R A R B R C and R D 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, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; L A and L B They are different; Ir(L A The first triplet excited state energy of )3 is lower than that of Ir(L B The first triplet excited state energy of )3, or L A The molecular weight is greater than L B The molecular weight; and One or both of the following conditions are true: (1) Ir(L A )2(L B The photoluminescence spectrum of Ir(L) has an emission peak, which has a full width at half maximum (FWHM) (1); A (L) B The photoluminescence spectrum of )2 has an emission peak, which has a full width at half maximum (FWHM) (2); and FWHM (2) - FWHM (1) is equal to or greater than 2 nm; (2) Ir(L A )2(L B M / T ratio of Ir(L) A (L) B The M / T of )2 is at least 0.

01.

15. A consumer product comprising the OLED according to claim 1.

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