Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. Provided is an organic compound comprising two 6-membered aromatic rings bonded to each other via a direct bond as a central structure, in which a first ring of the two 6-membered aromatic rings comprises at least one nitrogen atom, but not more than three nitrogen atoms. Formulations comprising these organic compounds are also provided. Also provided are organic light emitting devices (OLEDs) and related consumer products using these organic compounds.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 63 / 593,595, filed on October 27, 2023, the entire contents of which are incorporated herein by reference. This application further claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 63 / 593,600, filed on October 27, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates generally to organic or metal coordination compounds and formulations and various uses thereof, including as emitters, hosts, sensitizers, charge transporters, or exciton transporters in devices such as organic light emitting diodes and related electronic devices and consumer products. Background Art

[0004] Optoelectronic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many materials used to manufacture the devices are relatively inexpensive, so organic optoelectronic devices have the potential to have cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) can make them more suitable for specific applications, such as manufacturing on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, organic scintillators, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

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

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

[0007] In one aspect, the present disclosure provides compounds comprising Formula I

[0008]

[0009] in

[0010] X 1 To X 3 are independently CR or N, and X 1 To X 3 At least one of them is N;

[0011] X 4 To X 6 independently C or N;

[0012] R A It is a single substitution to a maximum of substitutions allowed;

[0013] each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0014] Each R A are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, aryl substituted with CN, heteroaryl substituted with CN, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0015] R 1 To R 4 are independently selected from the group consisting of aryl, heteroaryl, silane and germyl, wherein each R 1 To R 4 is optionally further substituted; and

[0016] Any R 3 , R 4 and R A May be joined or fused to form a ring.

[0017] In another aspect, the present disclosure provides formulations of the compounds as described herein.

[0018] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound as described herein.

[0019] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound as described herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 An organic light emitting device is shown.

[0021] Figure 2 An inverted organic light-emitting device without a separate electron transport layer is demonstrated. DETAILED DESCRIPTION

[0022] A. Terminology

[0023] Unless otherwise specified, the following terms used herein are defined as follows:

[0024] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed "above" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, there may be other layers between the first and second layers. For example, a cathode may be described as being "disposed "above" an anode even though various organic layers are present between the cathode and the anode.

[0025] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0026] As used herein, and as will be generally understood by one skilled in the art, a first "Highest Occupied Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum energy level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram with the vacuum energy level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears closer to the top of this diagram than a "lower" HOMO or LUMO energy level.

[0027] As used herein, and as one skilled in the art would generally understand, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are typically measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being farther away from the vacuum level in a downward direction. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0028] Layers, materials, regions, and devices may be described herein with reference to the color of light they emit. Generally, as used herein, an emissive region described as producing a particular color of light may include one or more emissive layers disposed above each other in a stacked manner.

[0029] As used herein, a "NIR," "red," "green," "blue," or "yellow" layer, material, region, or device refers to a layer, material, region, or device that emits light in a wavelength range of about 700-1500 nm, 580-700 nm, 500-600 nm, 400-500 nm, or 540-600 nm, respectively, or a layer, material, region, or device having the highest emission spectrum peak in the corresponding wavelength region. In some arrangements, separate regions, layers, materials, or devices may provide separate "deep blue" and "light blue" emissions. As used herein, a "deep blue" emission component refers to an emission having a peak emission wavelength that is at least about 4 nm less than the peak emission wavelength of a "light blue" emission component. Typically, the peak emission wavelength of the "light blue" emission component is in the range of about 465-500 nm, and the peak emission wavelength of the "deep blue" emission component is in the range of about 400-470 nm, but these ranges may vary for some configurations.

[0030] In some arrangements, a color-changing layer is provided that converts, modifies or changes the color of light emitted by another layer to an emission having a different wavelength. This color-changing layer can be configured to shift the wavelength of light emitted by another layer by a defined amount, as measured by the difference between the wavelength of the emitted light and the wavelength of the resulting light. In general, there are two types of color-changing layers: color filters that modify the spectrum by removing light of non-desired wavelengths, and color-changing layers that convert higher energy photons into lower energy. For example, there may be a "red" filter to filter the input light to remove light with wavelengths outside the range of about 580-700nm. A component of "color" refers to a component that produces or otherwise emits light having a specific color as previously described when activated or used. For example, a "first emission region of a first color" and a "second emission region of a second color different from the first color" describe two emission regions that emit two different colors as previously described when activated within the device.

[0031] As used herein, emissive materials, layers, and regions may be distinguished from each other and from other structures based on the light that the material, layer, or region initially produces as opposed to the light that the same or different structure ultimately emits. Initial light generation is typically the result of a change in energy levels that results in photon emission. For example, an organic emissive material may initially produce blue light, which may be converted to red or green light by a color filter, quantum dots, or other structure, such that the complete emissive stack or sub-pixel emits red or green light. In this case, the initial emissive material, region, or layer may be referred to as the "blue" component, even if the sub-pixel is the "red" or "green" component.

[0032] In some cases, it may be preferred to describe the color of a component, such as the color of an emitting region, a sub-pixel, a color-changing layer, etc., in terms of 1931 CIE coordinates. For example, a yellow emitting material may have multiple peak emission wavelengths, one in or near the edge of a "green" region, and one in or near the edge of a "red" region, as previously described. Thus, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. Shapes in the 1931 CIE color space are constructed by tracing the trajectory between two color points and any other interior points. For example, the interior shape parameters for red, green, blue, and yellow may be defined as follows:

[0033]

[0034]

[0035] The terms "halo," "halogen," and "halo" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0036] The term "acyl" refers to a substituted carbonyl (-C(O)-R s ).

[0037] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0038] The term "ether" refers to -OR s Group.

[0039] The terms "thio" or "thioether" are used interchangeably and refer to -SR s Group.

[0040] The term "selenoalkyl" refers to -SeR s Group.

[0041] The term "sulfinyl" refers to -S(O)-R s Group.

[0042] The term "sulfonyl" refers to -SO2-R s Group.

[0043] The term "phosphino" refers to a group containing at least one phosphorus atom bonded to a related structure. Common examples of phosphino groups include, but are not limited to, -P(R s )2 group or -PO(R s )2 groups, wherein each R s Can be the same or different.

[0044] The term "silyl group" refers to a group containing at least one silicon atom bonded to the structure of interest. Common examples of silyl groups include, but are not limited to, -Si(R s )3 groups, wherein each R s Can be the same or different.

[0045] The term "germanyl" refers to a group containing at least one germanium atom bonded to an associated structure. Common examples of germanyl groups include, but are not limited to, -Ge(R s )3 groups, wherein each R s Can be the same or different.

[0046] The term "boryl" refers to a group containing at least one boron atom bonded to the structure of interest. Common examples of boryl groups include, but are not limited to, -B(R s )2 group or its Lewis adduct -B(R s )3 groups, wherein R s Can be the same or different.

[0047] In each of the above, R s It may be hydrogen or a substituent selected from the group consisting of general substituents defined in this application. s is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. More preferably, R s Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0048] The term "alkyl" refers to and includes straight and branched chain alkyl groups having alkyl carbon atoms bonded to the relevant structure. Preferred alkyl groups are those containing one to fifteen carbon atoms, preferably one to nine carbon atoms, and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. In addition, the alkyl group may be further substituted.

[0049] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spiroalkyl groups having cycloalkyl carbon atoms bonded to the relevant structure. Preferred cycloalkyl groups are cycloalkyl groups containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. In addition, the cycloalkyl group may be further substituted.

[0050] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge and Se, preferably O, S or N. In addition, the heteroalkyl or heterocycloalkyl group may be further substituted.

[0051] The term "alkenyl" refers to and includes straight and branched alkenyls.Alkenyl is essentially an alkyl group including at least one carbon-carbon double bond in the alkyl chain, wherein one carbon atom from the carbon-carbon double bond is bonded to a related structure.Cycloalkenyl is essentially a cycloalkyl group including at least one carbon-carbon double bond in a cycloalkyl ring.As used herein, the term "heteroalkenyl" refers to an alkenyl group in which at least one carbon atom is replaced by a heteroatom.Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge and Se, preferably O, S or N.Preferred alkenyl, cycloalkenyl or heteroalkenyl groups are those containing two to fifteen carbon atoms.In addition, alkenyl, cycloalkenyl or heteroalkenyl groups may be further substituted.

[0052] The term "alkynyl" refers to and includes straight and branched chain alkynyl groups. Alkyl groups are generally alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain, wherein one carbon atom from the carbon-carbon triple bond is bonded to the associated structure. Preferred alkynyl groups are alkynyl groups containing two to fifteen carbon atoms. In addition, alkynyl groups may be further substituted.

[0053] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group having an alkyl carbon atom bonded to the associated structure that is substituted with an aryl group. Additionally, the aralkyl group may be further substituted.

[0054] 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. Aromatic heterocyclic groups can be used interchangeably with heteroaryl. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 to 10 ring atoms, preferably 3 to 7 ring atoms, including at least one heteroatom, and include cyclic amines, such as morpholinyl, piperidinyl, pyrrolidinyl, etc., and cyclic ethers / thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. In addition, the heterocyclic group can be further substituted or fused.

[0055] The term "aryl" refers to and includes monocyclic and polycyclic aromatic hydrocarbon groups. Polycyclic rings may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"). Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty-four carbon atoms, six to eighteen carbon atoms, and more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons, twelve carbons, fourteen carbons, or eighteen carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene and naphthalene. In addition, the aryl group may be further substituted or fused, such as but not limited to, fluorene.

[0056] The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems that include 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 with 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Heteropolycyclic ring systems may have two or more aromatic rings in which two atoms are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is a heteroaryl. Heteropolycyclic aromatic ring systems may have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indole, oxazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenophenobenzodipyridine, azaborane, borazine, 5λ 2 ,9λ 2 -diaza-13b-boronaphtho[2,3,4-de]anthracene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 5λ 2 ,9λ 2 -diaza-13b-boronaphtho[2,3,4-de]anthracene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene. In addition, the heteroaryl group may be further substituted or fused.

[0057] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 5λ 2 ,9λ 2-diaza-13b-boronaphtho[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, and their respective aza analogs are of particular interest.

[0058] In many cases, the general substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenoanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0059] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0060] In some cases, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, aryl, heteroaryl, nitrile, thio, and combinations thereof.

[0061] In other cases, even more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, silane, aryl, heteroaryl, nitrile, and combinations thereof.

[0062] In other cases, the most preferred general substituents are selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0063] The terms "substituted" and "substituted" refer to the bonding of substituents other than H to the relevant positions, such as carbon or nitrogen. For example, when R 1 When it represents a single substitution, one R 1 must not be H (i.e., substituted). Similarly, when R 1 When it indicates disubstituted, the two R 1 must not be H. Similarly, when R 1 When it indicates zero or no substitution, R 1 For example, it can be hydrogen with all available valences of the ring atoms, such as the carbon atoms of benzene and the nitrogen atoms in pyrrole, or simply none for ring atoms with fully saturated valences, such as the nitrogen atoms in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences in the ring atoms.

[0064] As used herein, "combinations thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that a person of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloaralkyl. In one example, the term substitution includes a combination of two to four listed groups. In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0065] The "aza" designation in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the CH groups in the corresponding aromatic ring can be replaced by a nitrogen atom, for example and without any limitation, azatriphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.

[0066] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be easily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951 and U.S. Patent Application Publication No. US2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Review) 2007, 46, 7744-65 (which are incorporated by reference in their entirety) respectively describe the deuteration of methylene hydrogen in benzylamine and the effective way to replace aromatic ring hydrogen with deuterium.

[0067] As used herein, any specific listed substituent, such as but not limited to methyl, phenyl, pyridyl, etc., includes its non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituents such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc. also include their non-deuterated, partially deuterated, and fully deuterated forms. Unless otherwise specified, atoms in a chemical structure that do not have a valence fully filled by H or D should be considered to include their non-deuterated, partially deuterated, and fully deuterated forms. For example, the chemical structure It is meant to include C6H6, C6D6, C6H3D3 and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, but are not limited to, CD3, CD2C(CH3)3, C(CD3)3 and C6D5.

[0068] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name can be written as if it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0069] In some cases, a pair of substituents in a molecule can be optionally joined or fused to form a ring. Preferred rings are five to nine-membered carbocyclic or heterocyclic rings, including two cases in which a portion of the ring formed by the pair of substituents is saturated and a portion of the ring formed by the pair of substituents is unsaturated. In other cases, a pair of adjacent substituents can be optionally joined or fused to form a ring. As used herein, "adjacent" means that the two substituents involved can be adjacent to each other on the same ring, or on two adjacent rings with two closest available substitutable positions (such as 2, 2' positions in biphenyl or 1, 8 positions in naphthalene).

[0070] B. Compounds of the Disclosure

[0071] In one aspect, the present disclosure provides compounds comprising Formula I

[0072]

[0073] in

[0074] X 1 To X 3 are independently CR or N, and X 1 To X 3 At least one of them is N;

[0075] X 4 To X 6 independently C or N;

[0076] R A It is a single substitution to a maximum of substitutions allowed;

[0077] each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0078] Each R A are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, aryl substituted with CN, heteroaryl substituted with CN, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0079] R 1 To R 4 are independently selected from the group consisting of aryl, heteroaryl, silane and germyl, wherein each R 1 To R 4 is optionally further substituted; and

[0080] Any R 3 , R 4 and R A May be joined or fused to form a ring.

[0081] In some embodiments, each R is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0082] In some embodiments, R 3 and R 4 Neither R A Join to form a 5-membered ring.

[0083] In some embodiments, if R 1 and R 2 Each is an aryl group, then the compound contains a silane group, a germane group or a borane group.

[0084] In some embodiments, if X 1 To X 3 Each is N, then X 4 To X 6 None of them is N. In some embodiments, if R 1 To R 3Each is an unsubstituted fully or partially deuterated or non-deuterated carbazole, then at least one R A Not H or R 4 Not triphenylsilane, carbazole dibenzothiophene, dibenzofuran, benzene or N-phenylcarbazole or their fully or partially deuterated analogs.

[0085] In some embodiments, if R 1 To R 4 are each unsubstituted carbazole, then at least one R A Not H.

[0086] In some embodiments, each R is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0087] In some embodiments, each R A are independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, aryl substituted with CN, heteroaryl substituted with CN, isonitrile, thio, and combinations thereof.

[0088] In some embodiments, X 1 To X 3 At least one of them is N.

[0089] In some embodiments, X 1 To X 3 Exactly one of them is N.

[0090] In some embodiments, X 1 To X 3 At least two of them are N.

[0091] In some embodiments, X 1 To X 3 There are exactly two N in it.

[0092] In some embodiments, X 1 To X 3 All are N.

[0093] In some embodiments, X 4 To X 6 At least one of them is N.

[0094] In some embodiments, X 4 To X 6 All are CR.

[0095] In some embodiments, R 1 and R 2 At least one of the compounds is a substituted or unsubstituted carbazole.

[0096] In some embodiments, R 1 and R 2 All are substituted or unsubstituted carbazoles.

[0097] In some embodiments, R 3 and R 4 Each is selected from a substituted or unsubstituted aryl or heteroaryl group.

[0098] In some embodiments, R 3 and R 4 Each is selected from substituted or unsubstituted carbazole, substituted or unsubstituted benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bisbenzimidazolidinone) and aza modifications thereof.

[0099] In some embodiments, R 1 To R 4 At least one of the carbazoles is a substituted carbazole.

[0100] In some embodiments, R 1 To R 4 At least two of the carbazoles are substituted.

[0101] In some embodiments, R 1 To R 4 At least one of the compounds is unsubstituted carbazole.

[0102] In some embodiments, R 1 To R 4 At least two of them are unsubstituted carbazoles.

[0103] In some embodiments, at least one R A Not hydrogen.

[0104] In some embodiments, at least one R A is an aryl group or a heteroaryl group.

[0105] In some embodiments, all R A It's all hydrogen.

[0106] In some embodiments, the compound comprises at least one silane group.

[0107] In some embodiments, the compound comprises at least one tetraphenylsilyl group.

[0108] In some embodiments, the compound comprises at least two silane groups.

[0109] In some embodiments, the compound comprises at least two tetraphenylsilyl groups.

[0110] In some embodiments, the compound comprises at least three carbazole groups.

[0111] In some embodiments, the compound comprises at least four carbazole groups.

[0112] In some embodiments, the compounds are fully or partially deuterated.

[0113] In some embodiments, the compound does not comprise a moiety selected from Formula II, III, IV, V, VI, and VII:

[0114]

[0115]

[0116] wherein rings A, B and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0117] Wherein each X in Formula II, III, IV, V, VI and VII 7 To X 84 and X 201 To X 216 independently C or N;

[0118] Where Z 1 To Z 4 and Y E Each is independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR', PR, CR, C=X, CRR', SO, SO2, SiRR', GeRR', P(O)R, aryl, heteroaryl, alkyl, heterocycloalkyl and cycloalkyl;

[0119] wherein X is selected from the group consisting of O, S and CRR';

[0120] Where W 1 and W 2 Each independently selected from the group consisting of: O, S, Se, CRR', SiRR' and GeRR';

[0121] Where Z A independently C, Si or Ge;

[0122] Among them, each R AA , R BB , R C , R D , R E , R F , R G , RH , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W and R X represents mono-substitution to the maximum amount of substitution, or no substitution;

[0123] Among them, R, R', R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W and R X Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof.

[0124] In some embodiments, the compound does not comprise a moiety of Formula II as defined above.

[0125] In some embodiments, the compound does not comprise a moiety of Formula III as defined above.

[0126] In some embodiments, the compound does not comprise a moiety of Formula VI as defined above.

[0127] In some embodiments, the compound does not comprise a moiety of Formula V as defined above.

[0128] In some embodiments, the compound does not comprise a moiety of Formula VI as defined above.

[0129] In some embodiments, the compound does not comprise a moiety of Formula VII as defined above.

[0130] In some embodiments, R 1 To R 4 Each of is selected from substituted or unsubstituted carbazole, substituted or unsubstituted bisbenzimidazole imidazole, substituted or unsubstituted benzene ring, substituted or unsubstituted 6-membered heteroaromatic ring, substituted silane group or substituted germane group. In some embodiments, R 1 To R 4 Each of the following is selected from unsubstituted carbazole, fully or partially deuterated carbazole, unsubstituted bisbenzimidazolidazole, fully or partially deuterated bisbenzimidazolidazole, fully or partially deuterated benzene ring, carbazole or bisbenzimidazolidazole substituted with a group selected from alkyl, silane or nitrile, unsubstituted benzene ring, benzene ring substituted with alkyl, benzene ring fused with cycloalkyl, benzene ring substituted with one or more non-fused aromatic or heteroaromatic rings, benzene ring substituted with silane or germyl, unsubstituted 6-membered heteroaromatic ring, fully or partially deuterated a 6-membered heteroaromatic ring substituted with an alkyl group, a 6-membered heteroaromatic ring fused to a cycloalkyl group, a 6-membered heteroaromatic ring substituted with one or more non-fused aromatic or heteroaromatic rings, a 6-membered heteroaromatic ring substituted with a silyl or germyl group, a silyl or germyl group substituted with three aromatic or heteroaromatic rings, a silyl or germyl group substituted with two aromatic or heteroaromatic rings and an alkyl group, a silyl or germyl group substituted with one aromatic or heteroaromatic ring and two alkyl groups, or a silyl or germyl group substituted with three alkyl groups.

[0131] In some embodiments, R 1 To R 3 Each is an unsubstituted fully or partially deuterated or non-deuterated carbazole.

[0132] In some embodiments, at least one R A is not H. In some embodiments, at least one R A is selected from the group consisting of alkyl, aryl, heteroaryl, silane, germane and combinations thereof. In some embodiments, at least two R A In some embodiments, at least two R A In some embodiments, at least two R A In some embodiments, at least two R A In some embodiments, at least two R A In some embodiments, R 4is not triphenylsilane, carbazole, dibenzothiophene, dibenzofuran, benzene or N-phenylcarbazole or a fully or partially deuterated analog thereof. 4 is a substituted triphenylsilane, a substituted carbazole, a substituted dibenzothiophene, a substituted dibenzofuran, a substituted benzene or a substituted N-phenylcarbazole. In some embodiments, R 4 In some embodiments, R 4 Contains at least one nitrile group.

[0133] In some embodiments, R 1 To R 4 In some embodiments, two or more of R are not unsubstituted fully or partially deuterated or non-deuterated carbazoles. 1 To R 4 In some embodiments, two or more of R 3 and R 4 None of them is substituted or unsubstituted carbazole. In some embodiments, R 1 and R 2 In some embodiments, at least one of R 1 and R 2 At least one of is a substituted or unsubstituted 6-membered carbocyclic or heterocyclic ring. In some embodiments, R 3 and R 4 are substituted or unsubstituted 6-membered carbocyclic or heterocyclic rings. 1 To R 4 At least one of R comprises a silane group or a nitrile group. 1 To R 4 At least one of the compounds is a substituted or unsubstituted bisbenzimidazolidinone.

[0134] In some embodiments, the compound has a LUMO level < -2.65.

[0135] In some embodiments, the compound has a LUMO level of <-2.7.

[0136] In some embodiments, the compound has a LUMO level of <-2.75.

[0137] In some embodiments, the compound has a LUMO level of <-2.8.

[0138] In some embodiments, the compounds have a singlet-triplet energy gap of >0.2 eV.

[0139] In some embodiments, the compound has an anion reorganization energy of <0.7 eV.

[0140] In some embodiments, the compound has an anion reorganization energy of <0.6 eV.

[0141] In some embodiments, the compound is selected from the group consisting of:

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] Where X 7 To X 46 each independently is C or N;

[0149] R B To R G and R DD Each is a single substitution up to the maximum number of substitutions allowed;

[0150] Each R B , R C , R D , R E , R F , R G , R 5 , R 6 and R 7 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0151] Each R DD is deuterated or a fully or partially deuterated substituent.

[0152] In some embodiments, the compound is selected from the group consisting of compound W1-(Rm)(Rn)(Ro)(Rp), compound W2-(Rn)(Ro)(Rp)(Rq), and compound W3-(Rn)(Ro)(Rp)(Zk), wherein W1 is an integer from 1 to 4 and 33 to 38, wherein W2 is an integer from 5 to 23, wherein W3 is an integer from 24 to 32, m is an integer from 1 to 139, n, o, p, q are each an integer from 1 to 141, k is an integer from 1 to 84, each Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R141, wherein Zk is selected from the group consisting of Z1 to Z84. group; wherein each of compounds 1-(R1)(R1)(R1)(R1) to compounds 4-(R139)(R141)(R141)(R141), compounds 5-(R1)(R1)(R1)(R1) to compounds 23-(R141)(R141)(R141)(R141), compounds 24-(R1)(R1)(R1)(Z1) to compounds 32-(R141)(R141)(R141)(Z84) and compounds 33-(R1)(R1)(R1)(R1) to compounds 38-(R139)(R141)(R141)(R141) are defined as follows:

[0153]

[0154]

[0155]

[0156]

[0157] Where Z1 to Z84 are defined in List A below:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] Where R1 to R141 are defined in Table B below:

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] In some embodiments, the compound is selected from the group consisting of the structures in List C below:

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] In another aspect, the present disclosure provides compounds having a structure of Formula I*;

[0192]

[0193] wherein the compound is partially or fully deuterated;

[0194] Where X 1* , X 2* and X 3* Each is independently CR * or N;

[0195] Where X 1* , X 2* and X 3* At least two of them are N;

[0196] Where R * , R 1* , R 2* and R 3* are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0197] Where R 1* , R 2* and R 3* At least one of them has a structure of Formula II*:

[0198]

[0199] Where Z 1* and Z 2* Each is a group having a molecular weight (MW) ≥ 77 g / mol;

[0200] Wherein the dotted line ------- represents a direct bond, and the direct bond is connected to the X-containing 1* , X 2* and X 3* The ring carbon atoms contained in the ring of

[0201] wherein [X] represents a monocyclic ring containing one 5- to 10-membered carbocyclic or heterocyclic ring, or a polycyclic fused ring system containing at least two fused 5- to 10-membered carbocyclic or heterocyclic rings, and may be further substituted;

[0202] where Y 1* and Y 2* are all independently a single bond or a linking group;

[0203] Where Z 1* and Z 2* Essentially reside in the formula I* containing X 1* , X 2* and X 3* The rings are above and below the plane of the ring.

[0204] In some embodiments, X 1* To X 3* At least one of them is N.

[0205] In some embodiments, X 1* To X 3* Exactly one of them is N.

[0206] In some embodiments, X 1* To X 3* At least two of them are N.

[0207] In some embodiments, X 1* To X 3* There are exactly two N in it.

[0208] In some embodiments, X 1* To X 3* All are N.

[0209] In some embodiments, the compound of formula I* containing X 1* , X 2* and X 3* The center of mass of the ring is related to Z 1* and Z 2* The nearest intramolecular contact between each of

[0210] In some embodiments, R * , R 1* , R 2* and R 3* Each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0211] In some embodiments, Y 1* and Y 2* At least one of them is a single bond.

[0212] In some embodiments, Y 1* and Y 2* Exactly one of them is a single bond.

[0213] In some embodiments, Y 1* and Y2* All are single keys.

[0214] In some embodiments, the compounds are partially deuterated.

[0215] In some embodiments, the compounds are deuterated to have at least 2 deuterium atoms.

[0216] In some embodiments, the compound is deuterated to have at least 6 deuterium atoms.

[0217] In some embodiments, the compounds are deuterated with at least 10 deuterium atoms.

[0218] In some embodiments, the compound is deuterated to have at least 14 deuterium atoms.

[0219] In some embodiments, the compound is deuterated to have at least 18 deuterium atoms.

[0220] In some embodiments, the compounds are fully deuterated.

[0221] In some embodiments, Z 1* and Z 2* Each is independently a monocyclic ring containing one 5- to 10-membered carbocyclic or heterocyclic ring, or a polycyclic fused ring system containing at least two fused 5- to 10-membered carbocyclic or heterocyclic rings. 1 and Z 2 Monovalent saturated monocyclic alkyl groups are not included.

[0222] In some embodiments, R 1* , R 2* and R 3* At least one of is R**, wherein R** has Formula III:

[0223]

[0224] Some of them are 1 ' and Z 2 'Each independently is a monocyclic or polycyclic condensed ring system, wherein each ring in the monocyclic or polycyclic condensed ring system is independently a 5- to 10-membered carbocyclic or heterocyclic ring;

[0225] Where R Z1 ' and R Z2 ' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0226] In some embodiments, part Z 1* , Z 2* , Z 1 ' and Z 2 ' are each independently a monocyclic or fused polycyclic ring system containing one or more 5-membered or 6-membered carbocyclic or heterocyclic rings.

[0227] In some embodiments, Z 1* and Z 2* Each is independently selected from the group consisting of phenyl, carbazole, silane and tetraphenylene.

[0228] In some embodiments, R 1* , R 2* and R 3* There is exactly one of them having formula III.

[0229] In some embodiments, R 1* , R 2* and R 3* At least two of the compounds have formula III.

[0230] In some embodiments, R 1* , R 2* and R 3* There are exactly two of them with formula III.

[0231] In some embodiments, R 1* , R 2* and R 3* All three of have the formula III.

[0232] In some embodiments, [X] is a monocyclic or fused polycyclic ring system comprising one or more 5- or 6-membered carbocyclic or heterocyclic rings.

[0233] In some embodiments, [X] is a chemical moiety comprising at least one six-membered carbocyclic ring, silane, germane, or heterocyclic ring.

[0234] In some embodiments, [X] comprises a 6-membered ring.

[0235] In some embodiments, [X] is a 6-membered ring.

[0236] In some embodiments, [X] comprises a 6-membered aromatic ring.

[0237] In some embodiments, [X] is a 6-membered aromatic ring.

[0238] In some embodiments, [X] comprises a 6-membered carbocyclic aromatic ring.

[0239] In some embodiments, [X] is a 6-membered carbocyclic aromatic ring.

[0240] In some embodiments, [X] comprises at least one chemical moiety selected from the group consisting of the structures in Listing 1* below:

[0241]

[0242] where Y T , Y U , Y V and Y W Each independently selected from the group consisting of BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR' and GeRR';

[0243] Among them, each R T can be the same or different, and each R T is independently a donor, an acceptor group, an organic linker bonded to a donor, an organic linker bonded to an acceptor group, or a terminal group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an aryl group, a heteroaryl group, and combinations thereof; and

[0244] R and R' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof.

[0245] In some embodiments, R 1* Having the formula II*, Y 1* and Y 2* Same, and Z 1* and Z 2* same.

[0246] In some embodiments, R 1* Having the formula II*, Y 1* and Y 2* Same, and Z 1* and Z 2* Not the same.

[0247] In some embodiments, the compound comprises at least two carbazole groups.

[0248] In some embodiments, the compound comprises at least two fully deuterated carbazole groups.

[0249] In some embodiments, the compound comprises at least three carbazole groups.

[0250] In some embodiments, the compound comprises at least three fully deuterated carbazole groups.

[0251] In some embodiments, the compound comprises at least one silane group.

[0252] In some embodiments, the compound comprises at least one fully deuterated silyl group.

[0253] In some embodiments, the compound has a C2 axis of symmetry.

[0254] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS and wherein R** is closest to M in the compound TS One of the 10 atoms is directly bonded to the rest of the compound.

[0255] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS The mass center of R** is located at position M R Where; and where M TS To M R The distance is less than 2.0nm.

[0256] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS The mass center of R** is located at position M R Where; and where M TS To M R The distance is less than 1.5nm.

[0257] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS The mass center of R** is located at position M R Where; and where M TS To M R The distance is less than 1.0nm.

[0258] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 1 The center of mass is located at position M Z1 '; and where M TA To M Z1 'The distance is less than 2.0nm.

[0259] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 1 The center of mass is located at position MZ1 '; and where M TA To M Z1 'The distance is less than 1.5nm.

[0260] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 1 The center of mass is located at position M Z1 '; and where M TA To M Z1 'The distance is less than 1.0nm.

[0261] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 2 The center of mass is located at position M Z2 '; and where M TA To M Z2 'The distance is less than 2.0nm.

[0262] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 2 The center of mass is located at position M Z2 '; and where M TA To M Z2 'The distance is less than 1.5nm.

[0263] In some embodiments, the center of mass of the lowest triplet excited state spin density in the compound is located at position M TS Where Z 2 The center of mass is located at position M Z2 '; and where M TA To M Z2 'The distance is less than 1.0nm.

[0264] In some embodiments, the LUMO mass center in the compound is located at position M LA and wherein R* is closest to M in the compound LA One of the 10 atoms is directly bonded to the rest of the compound.

[0265] In some embodiments, the LUMO mass center in the compound is located at position M LA where the mass center of R* is located at position M R Where; and where M LA To M R The distance is less than 2.0nm.

[0266] In some embodiments, the LUMO mass center in the compound is located at position M LA where the mass center of R* is located at position M R Where; and where M LA To M R The distance is less than 1.5nm.

[0267] In some embodiments, the LUMO mass center in the compound is located at position M LA where the mass center of R* is located at position M R Where; and where M LA To M R The distance is less than 1.0nm.

[0268] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 1 The center of mass is located at position M Z1 '; and where M LA To M Z1 'The distance is less than 2.0nm.

[0269] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 1 The center of mass is located at position M Z1 '; and where M LA To M Z1 'The distance is less than 1.5nm.

[0270] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 1 The center of mass is located at position M Z1 '; and where M LA To M Z1 'The distance is less than 1.0nm.

[0271] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 2 The center of mass is located at position M Z2 '; and where M LA To M Z2 'The distance is less than 2.0nm.

[0272] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 2 The center of mass is located at position M Z2'; and where M LA To M Z2 'The distance is less than 1.5nm.

[0273] In some embodiments, the LUMO mass center in the compound is located at position M LA Where Z 2 The center of mass is located at position M Z2 '; and where M LA To M Z2 'The distance is less than 1.0nm.

[0274] It should be understood that the above parameters, such as the mass center of the lowest triplet excited state spin density of the compound, the HOMO mass center of the compound, the LUMO mass center of the compound, the mass center of the compound and the mass center of R*, and all the distances and the above parameters identified can be obtained via DFT calculations. The 10 atoms closest to the relevant positions identified above can also be calculated using DFT.

[0275] In some embodiments, [X] is a chemical moiety comprising at least 6 carbon atoms.

[0276] In some embodiments, [X] comprises at least one 6-membered aromatic ring.

[0277] In some embodiments, [X] is selected from the group consisting of a substituted or unsubstituted monocyclic ring, a substituted or unsubstituted polycyclic fused ring system, SiR P 、SiR P R Q ,GeR P ,GeR P R Q , BR P , BR P R Q , CR P R Q NR P and PR P , where R P Contains a 6-membered carbocyclic or heterocyclic ring, and R Q is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof.

[0278] In some embodiments, a monocyclic ring, R P and R QEach is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine and triazine; the single ring may be further substituted; R and R' may be further substituted or fused; wherein the polycyclic fused ring system is each selected from the group consisting of triphenylene, carbazole, indolecarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene and aza modifications thereof.

[0279] In some embodiments, R** is partially or fully deuterated.

[0280] In some embodiments, the compound comprises at least one substituent having a sphericity greater than or equal to 0.45.

[0281] In some embodiments, the compound comprises at least one substituent having a sphericity greater than or equal to 0.55.

[0282] In some embodiments, the compound comprises at least one substituent having a sphericity greater than or equal to 0.65.

[0283] In some embodiments, the compound comprises at least one substituent having a sphericity greater than or equal to 0.75.

[0284] In some embodiments, the compound comprises at least one substituent having a sphericity greater than or equal to 0.80.

[0285] Sphericity is a measure of the three dimensions of a bulky group. Sphericity is defined as the ratio between principal moments of inertia (PMI). Specifically, sphericity is the ratio of three times PMI1 to the sum of PMI1, PMI2 and PMI3, where PMI1 is the minimum principal moment of inertia, PMI2 is the second minimum principal moment of inertia, and PMI3 is the maximum principal moment of inertia. The sphericity of the lowest energy conformation of the structure can be calculated after optimizing the ground state using density functional theory. More detailed information can be found in paragraphs

[0054] to

[0059] of U.S. Application No. 18 / 062,110 (filed on December 6, 2022), the contents of which are incorporated herein by reference.

[0286] In some embodiments, the compound comprises a van der Waals volume greater than at least one substituent.

[0287] In some embodiments, the compound comprises a van der Waals volume greater than at least one substituent.

[0288] In some embodiments, the compound comprises a van der Waals volume greater than at least one substituent.

[0289] In some embodiments, the compound comprises a van der Waals volume greater than at least one substituent.

[0290] In some embodiments, the compound comprises a van der Waals volume greater than at least one substituent.

[0291] In some embodiments, the compound comprises at least one substituent having a molecular weight greater than 167 amu (atomic mass units).

[0292] In some embodiments, the compound comprises at least one substituent having a molecular weight greater than 187 amu.

[0293] In some embodiments, the compound comprises at least one substituent having a molecular weight greater than 259 amu. In some embodiments, the compound comprises at least one substituent having a molecular weight greater than 303 amu. In some embodiments, the compound comprises at least one substituent having a molecular weight greater than 305 amu. In some embodiments, R** is selected from the group consisting of the structures in the following list 2*:

[0294]

[0295]

[0296] wherein rings A, B and C are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0297] Z 1 To Z 4 Each is independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR', PR, CR, C=X, CRR', SO, SO2, SiRR', GeRR', P(O)R, aryl, heteroaryl, alkyl, heterocycloalkyl and cycloalkyl;

[0298] Each X 101 To X 173 independently C or N;

[0299] Z A Selected from the group consisting of C, Si and Ge;

[0300] Where W 1 and W 2 are each independently selected from the group consisting of: a direct bond, O, S, Se, CRR', SiRR', and GeRR';

[0301] Each Y aa and Y bbindependently selected from the group consisting of: O, S, Se, CRR', SiRR', GeRR', NR, BR and BRR';

[0302] Each Y E , Y cc and Y dd independently selected from the group consisting of: O, S, Se, CRR', SiRR', GeRR', BR and BRR';

[0303] Each Y ee and Y ff independently selected from the group consisting of CR, SiR, GeR, B and N;

[0304] Each Q A To Q E Independently represents a single substitution to the maximum number of substitutions allowed, or no substitution;

[0305] Each R, R', Q A To Q E are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; any two substituents may be joined or fused to form a ring; and

[0306] In each benzene ring in any of the above structures, any carbon ring atom up to a total of up to three carbon ring atoms together with their substituents may be replaced by N.

[0307] In some embodiments, R** is selected from the group consisting of the structures in List 3* below:

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319] In some embodiments, the compound is selected from the group consisting of the structures in Listing 4* below:

[0320]

[0321]

[0322]

[0323]

[0324] Where X 1 To X 45 each independently is C or N;

[0325] Among them, each R A , R AA , R B , R C , R D , R E , R F and R G Independently represents a single substitution to the maximum number of substitutions allowed, or no substitution;

[0326] Where R A , R AA , R B , R C , R D , R E and R F Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0327] In some embodiments, the compound is selected from the group consisting of the structures in Listing 5* below:

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336] In some embodiments, the compound is selected from the group consisting of the compounds in the following List 6*:

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362] In some embodiments, part Z 1 ' and part Z 2 ' can be independently a polycyclic condensed ring structure. In some embodiments, part Z 1 ' and part Z 2 At least one of the ' may independently be a 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 coordinate with the metal. In some embodiments, the polycyclic fused ring structure has two 6-membered rings. In some embodiments, part Z 1 ' and part Z 2 At least one of ' can be independently selected from the group consisting of benzofuran, benzothiophene, benzoselenophene, naphthalene and aza variants thereof.

[0363] In some embodiments, part Z 1 ' and part Z 2 At least one of the ' may independently be a polycyclic fused ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused ring structure has two 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to the metal M and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, part Z 1 ' and part Z 2 At least one of ' can be independently selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene and aza variants thereof. In some such embodiments, the moiety Z 1 ' and part Z 2 At least one of ' may be further substituted independently at the ortho or meta position to the O, S or Se atom with a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza variant 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).

[0364] In some embodiments, part Z 1 ' and part Z2 ' may independently be a polycyclic fused ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused ring structure comprises three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to a ring coordinated to the metal M, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted by a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0365] In some embodiments, part Z 1 ' and part Z 2 'At least one of them may independently be a polycyclic condensed ring structure comprising at least five condensed rings. In some embodiments, the polycyclic condensed ring structure comprises four 6-membered rings and one 5-membered ring, or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments with one 5-membered ring, the 5-membered ring is fused with a ring coordinated with a 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.

[0366] In some embodiments, part Z 1 ' and part Z 2 ' may independently be an aza form of the above polycyclic fused ring. In some such embodiments, part Z 1 ' and part Z 2 ' may independently contain exactly one nitrogen heteroatom. In some such embodiments, the moiety Z 1 ' and part Z 2 In some embodiments, at least one of the rings contains exactly two nitrogen-N atoms, which may be in one ring or in two different rings. In some such embodiments, the ring with the nitrogen-N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring with the nitrogen-N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each ortho position of the nitrogen-N atom is substituted.

[0367] In some embodiments, the compounds of Formula I described herein 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 deuteration percentage has its ordinary meaning and includes the percentage of all possible hydrogen atoms (e.g., hydrogen or deuterium positions) occupied by deuterium atoms. In some embodiments, one or more hole transport moieties are partially or completely deuterated. In some embodiments, one or more electron transport moieties are partially or completely deuterated. In some embodiments, one or more fused ring systems are partially or completely deuterated. In some embodiments, one or more non-fused rings are partially or completely deuterated. In some embodiments, one or more rings or fused rings containing one or more heteroatoms are partially or completely deuterated. In some embodiments, one or more fused or non-fused phenyl rings are partially or fully deuterated. In some embodiments, one or more alkyl or cycloalkyl groups are partially or fully deuterated.

[0368] In some embodiments, the compound consists essentially of Formula I.

[0369] In some embodiments, the compound has the structure of Formula I.

[0370] In yet another aspect of the present disclosure, a formulation comprising the novel compounds disclosed herein is described. The formulation may include one or more components disclosed herein selected from the group consisting of: a solvent, an emitter, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material.

[0371] The present disclosure encompasses any chemical structure comprising novel compounds of the present disclosure or their monovalent or multivalent variants. In other words, the compounds of the present invention or their monovalent or multivalent variants can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of: monomers, polymers, macromolecules and supramolecules (also referred to as supermolecules). As used herein, "monovalent variants of compounds" refer to the same part as the compound, but one of the hydrogens has been removed and replaced with a bond to the rest of the chemical structure. As used herein, "multivalent variants of compounds" refer to the same part as the compound, but more than one hydrogen has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecules, the compounds of the present invention can also be incorporated into supramolecular complexes without covalent bonds. As used in this context, the description that structure A includes part B means that structure A includes the structure of part B, and the structure of part B does not include H or D atoms that can be connected to part B. This is because at least one H or D on a given part structure must be replaced with a substituent so that part B can be a part of structure A, and after it becomes a part of structure A, one or more of the H or D on a given part B structure can be further substituted.

[0372] C. OLEDs and Devices of the Present Disclosure

[0373] In another aspect, the present disclosure also provides an OLED device comprising a first organic layer containing a compound as disclosed in the above compound section of the present disclosure.

[0374] In some embodiments, an OLED comprises: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound described herein.

[0375] In some embodiments, the organic layer may be an emission layer.In some embodiments, the organic layer is selected from the group consisting of: a HIL, a HTL, an EBL, an EML, a HBL, an ETL, and an EIL.

[0376] In some embodiments, the compound can be a host, and the first organic layer can be an emission layer comprising a phosphorescent or fluorescent emitter. As used herein, phosphorescence generally refers to photon emission when the electron spin quantum number changes, that is, the initial and final states of the emission have different electron spin quantum numbers, such as from T1 to S0 state. Most of the Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, if the excited complex formation involves a triplet emitter, such excited complexes can also emit phosphorescence. On the other hand, a fluorescent emitter generally refers to photon emission when the electron spin quantum number does not change, such as from S1 to S0 state, or from D1 to D0 state. The fluorescent emitter can be a delayed fluorescent or non-delayed fluorescent emitter. Depending on the spin state, the fluorescent emitter can be a singlet emitter or a doublet emitter or other multiplet emitter. It is believed that the internal quantum efficiency (IQE) of the fluorescent OLED can exceed the 25% spin statistical limit through delayed fluorescence. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the thermal population between the triplet and singlet excited states. Thermal energy can activate the triplet transition back to the singlet state. This type of delayed fluorescence is also known as TADF. E-type delayed fluorescence characteristics can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that TADF emission requires a small singlet-triplet energy gap (ΔE) of less than or equal to 400, 350, 300, 250, 200, 150, 100 or 50 meV. S-T ) compounds or excited complexes. There are two main types of TADF emitters, one is called donor-acceptor type TADF and the other is called multi-resonance (MR) TADF. Typically, a single compound donor-acceptor TADF compound is constructed by connecting an electron donor portion (such as an amino or carbazole derivative) and an electron acceptor portion (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). A donor-acceptor excited complex can be formed between a hole transport compound and an electron transport compound. Examples of MR-TADF materials include highly conjugated fused ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. Such materials may also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 of delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, such time may be greater than 10 microseconds and less than 100 microseconds.

[0377] In some embodiments, the compound is a host and the organic layer is an emissive layer comprising a phosphorescent or fluorescent material.

[0378] In some embodiments, the emissive dopant may be a phosphorescent or fluorescent material.

[0379] In some embodiments, the non-emissive dopant may also be a phosphorescent or fluorescent material.

[0380] 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.

[0381] In some embodiments, the phosphorescent material is an emitter that emits light within the OLED. In some embodiments, the phosphorescent material does not emit light within the OLED. In some embodiments, the phosphorescent material energy transfers its excited state to another material within the OLED. In some embodiments, the phosphorescent material participates in charge transport within the OLED. In some embodiments, the phosphorescent material is a sensitizer or a component of a sensitizer, and the OLED further comprises an acceptor. In some embodiments, the phosphorescent material forms an exciplex with another material (e.g., a host material, an emitter material) within the OLED.

[0382] In some embodiments, the non-delayed fluorescent material or delayed fluorescent material is an emitter that emits light in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material does not emit light in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material energy transfers its excited state to another material in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material participates in charge transport in the OLED. In some embodiments, the non-delayed fluorescent material or delayed fluorescent material is an acceptor, and the OLED further comprises a sensitizer.

[0383] In some embodiments, the compound may be an acceptor, and the OLED may further include a sensitizer selected from the group consisting of a delayed fluorescent material, a phosphorescent material, and combinations thereof.

[0384] In some embodiments, the compound can be a non-delayed fluorescent emitter, a delayed fluorescent emitter, or a component of an exciplex that is a non-delayed fluorescent emitter or a delayed fluorescent emitter. In some embodiments, the emission of the 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. Narrower FWHM means better color purity for OLED display applications.

[0385] In some embodiments, the compound is a host and the OLED comprises an acceptor as an emitter and a sensitizer selected from the group consisting of a delayed fluorescent material, a phosphorescent material, and combinations thereof; wherein the sensitizer transfers energy to the acceptor.

[0386] In some embodiments, the phosphorescent material may be a metal coordination complex having a metal-carbon bond, a metal-nitrogen bond, or a metal-oxygen bond. In some embodiments, the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag, and Cu. In some embodiments, the metal is Ir. In some embodiments, the metal is Pt. In some embodiments, the metal is Cu, Ag, or Au. In some embodiments, the phosphorescent material has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0387] Where L 1 , L 2 and L 3 Can be the same or different;

[0388] where x is 1, 2, or 3;

[0389] Where y is 0, 1 or 2;

[0390] where z is 0, 1 or 2;

[0391] Wherein x+y+z is the oxidation state of the metal M;

[0392] Where L 1 Selected from the group consisting of structures in the following ligand list:

[0393]

[0394]

[0395]

[0396] Among them, each L 2 and L 3 Independently selected from the group consisting of: and a structure in the ligand list; wherein:

[0397] M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Au, Ag and Cu;

[0398] T is selected from the group consisting of B, Al, Ga and In;

[0399] K 1 ' is a direct key or is selected from the group consisting of: NR e , PR e , O, S and Se;

[0400] Each Y 1 To Y 15 independently selected from the group consisting of: carbon and nitrogen;

[0401] Y'Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO2,CR e R f 、SiR e R f and GeR e R f ;

[0402] R e and R f capable of being fused or joined to form a ring;

[0403] Each R a , R b , R c and R d can independently represent a single substitution to the maximum possible number of substitutions, or no substitution;

[0404] Each R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0405] Any two of the substituents can be fused or joined to form a ring or to form a multidentate ligand.

[0406] In some embodiments, the phosphorescent material has a structure of Formula XI or Formula XII:

[0407]

[0408] in:

[0409] X 105 To X 111 and Z 102 To Z 104 each independently is C or N;

[0410] Where K 1 and K 2Each independently selected from the group consisting of: direct key, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β );L 1 and L 2 Each independently selected from the group consisting of a direct bond, O, S, Se, NR', BR', BR'R", PR', CR', C=O, C=NR', C=CR'R", C=S, CR'R", SO, SO2, P(O)R', SiR'R", and GeR'R". AA '、R BB '、R CC '、R DD '、R EE '、R EE0 , R EE1 and R EE2 , R', R", R α and R β R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; EE ' indicates single substitution to the maximum number of substitutions allowed, or no substitution; and

[0411] Any two substituents therein may be joined or fused to form a ring.

[0412] In some embodiments, R EE1 and R EE2 In some embodiments, at least one of R AA '、R BB '、R CC '、R DD '、R EE '、R EE0 , R EE1 and R EE2 In some embodiments, at least one of R EE1 and R EE2 In some embodiments, at least one of R EE1 and R EE2 All are aromatic.

[0413] In some embodiments, R EE1and R EE2 At least one of the R comprises a chemical group containing at least three 6-membered aromatic rings, wherein adjacent aromatic rings are not fused to each other. EE1 or R EE2 At least one of the R comprises a chemical group containing at least four 6-membered aromatic rings, wherein adjacent aromatic rings are not fused to each other. EE1 or R EE2 At least one of the R comprises a chemical group containing at least five 6-membered aromatic rings, wherein adjacent aromatic rings are not fused to each other. EE1 or R EE2 At least one of the R comprises a chemical group containing at least six 6-membered aromatic rings, wherein adjacent aromatic rings are not fused to each other. EE1 and R EE2 Each of the above independently comprises a chemical group comprising at least three to six 6-membered aromatic rings, wherein adjacent aromatic rings are not fused to each other.

[0414] In some embodiments, R EE1 or R EE2 At least one of the groups contains a group R W , where R W Having a structure selected from the group consisting of: Formula IIIA, ---Q A (R 1a )(R 2a ) a (R 3a ) b , Formula IIIB, Japanese formula XIIIC, in:

[0415] X 130 To X 138 Each of is independently C or N;

[0416] Y S , Y T and Y U each of which is independently CRR', SiRR' or GeRR';

[0417] n is an integer from 1 to 8,

[0418] When n is greater than 1, each Y S Can be the same or different;

[0419] Q A Selected from the group consisting of: C, Si, Ge, N, P, O, S, Se and B;

[0420] Each of a and b is independently 0 or 1;

[0421] If Q A If it is C, Si or Ge, then a+b=2;

[0422] If Q A If it is N or P, then a+b=1;

[0423] If Q A is B, then a+b can be 1 or 2;

[0424] If Q A If it is O, S or Se, then a+b=0;

[0425] R SS , R TT and R UU Each of the above independently represents a single substitution to the maximum permissible number of substitutions, or no substitution;

[0426] Each R, R', R 1a , R 2a , R 3a , R SS , R TT and R UU is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and

[0427] Any two substituents therein may be optionally fused or joined to form a ring.

[0428] In some embodiments, at least one Y S , Y T or Y U is SiRR' or GeRR'. In some embodiments, each Y S , Y T and Y U is CRR'. In some embodiments, R EE1 and R EE2 At least one of R comprises an aromatic ring fused to a non-aromatic ring. EE1 and R EE2 In some embodiments, the aromatic ring is a benzene ring and the non-aromatic ring is a cycloalkyl ring. In some embodiments, R EE1 and R EE2 At least one of is partially or fully deuterated. In some embodiments, R EE1 and R EE2 are partially or completely deuterated. In some embodiments, R EE1 and R EE2 One of the A Join to form a ring.

[0429] In some embodiments, the phosphorescent material has a structure of Formula XIV or XV:

[0430]

[0431] in

[0432] X 112 To X 119 are independently C or N; R EE3 are independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and any two substituents may be joined or fused to form a ring.

[0433] In some embodiments, X 12 To X 19 Each is C. In some embodiments, X 12 To X 19 One is N. In some embodiments, X 12 To X 19 Two of them are N. In some embodiments, X 12 To X 15 One is N. In some embodiments, X 16 To X 19 One of them is N.

[0434] In another aspect, the present disclosure also provides an organic electroluminescent device (OLED), comprising:

[0435] anode;

[0436] cathode; and

[0437] an emission layer disposed between the anode and the cathode;

[0438] wherein the emission layer comprises an emission dopant and a first host;

[0439] Wherein the first host has Formula I*:

[0440]

[0441] wherein the compound is partially or fully deuterated;

[0442] Where X 1* , X 2* and X 3* Each is independently CR * or N;

[0443] Where X 1* , X 2* and X 3*At least two of them are N;

[0444] Where R * , R 1* and R 2* are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0445] Where R 3* Having the structure of formula II*:

[0446]

[0447] Where Z 1* and Z 2* Each is a group having a molecular weight (MW) ≥ 77 g / mol;

[0448] Wherein the dotted line ------- represents a direct bond, and the direct bond is connected to the X-containing 1* , X 2* and X 3* The ring carbon atoms contained in the ring of

[0449] wherein [X] represents a monocyclic ring containing one 5- to 10-membered carbocyclic or heterocyclic ring, or a polycyclic fused ring system containing at least two fused 5- to 10-membered carbocyclic or heterocyclic rings, and may be further substituted;

[0450] where Y 1* and Y 2* are all independently a single bond or a linking group;

[0451] Where Z 1* and Z 2* Essentially reside in the formula I* containing X 1* , X 2* and X 3* The rings are above and below the plane of the ring.

[0452] In some embodiments, the first host is a compound disclosed herein.

[0453] In another aspect, the present disclosure also provides an organic electroluminescent device (OLED), comprising:

[0454] anode;

[0455] cathode; and

[0456] an emission layer disposed between the anode and the cathode;

[0457] wherein the emission layer comprises an emission dopant and a first host;

[0458] Wherein the first host has Formula IV*:

[0459]

[0460] wherein the first host is partially or fully deuterated;

[0461] Where X 1 ', X 2 ' and X 3 'Each independently is CR or N;

[0462] Where X 1 ', X 2 ' and X 3 At least two of ' are N;

[0463] Among them, R 11 , R 12 and R 13 are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0464] Where R 11 , R 12 and R 13 At least one of them contains Z 3 And R 11 , R 12 and R 13 At least one of them contains Z 4 ;

[0465] Where Z 3 and Z 4 Each is a group having a molecular weight (MW) ≥ 77 g / mol;

[0466] Where Z 3 Residing in the formula I* containing X 1 ', X 2 ' and X 3 'The ring is on one side of the triazine ring plane, Z 4 Residing in the formula I* containing X 1 ', X 2 ' and X 3 ' on the other side of the triazine ring plane; and

[0467] Which contains X 1 ', X 2 ' and X 3 The mass center of the triazine ring is 3 and Z 4 The nearest intramolecular contact between each of

[0468] In some embodiments, in the first host of Formula IV*, X 1 'To X 3 At least one of ' is N.

[0469] In some embodiments, in the first host of Formula IV*, X 1 'To X 3 ' Exactly one of them is N.

[0470] In some embodiments, in the first host of Formula IV*, X 1 'To X 3 At least two of them are N.

[0471] In some embodiments, in the first host of Formula IV*, X 1 'To X 3 There are exactly two N in '.

[0472] In some embodiments, in the first host of Formula IV*, X 1 'To X 3 'All are N.

[0473] In some embodiments, in the first host of Formula IV*, R, R 11 , R 12 and R 13 Each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0474] In some embodiments, in the first host of Formula IV*, the first host is partially deuterated.

[0475] In some embodiments, in the first host of Formula IV*, the first host is deuterated to have at least 2 deuterium atoms.

[0476] In some embodiments, in the first host of Formula IV*, the first host is deuterated to have at least 6 deuterium atoms.

[0477] In some embodiments, in the first host of Formula IV*, the first host is deuterated to have at least 10 deuterium atoms.

[0478] In some embodiments, in the first host of Formula IV*, the first host is deuterated to have at least 14 deuterium atoms.

[0479] In some embodiments, in the first host of Formula IV*, the first host is deuterated to have at least 18 deuterium atoms.

[0480] In some embodiments, in the first host of Formula IV*, the first host is fully deuterated.

[0481] In some embodiments, in the first host of Formula IV*, R 11 , R 12 and R 13 At least one of them contains Z 3 and Z 4 .

[0482] In some embodiments, in the first host of Formula IV*, R 11 Contains Z 3 And R 12 and R 13 At least one of them contains Z 4 .

[0483] In some embodiments, in the first host of Formula IV*, R 11 , R 12 and R 13 At least one of the groups comprises a silane group or a germanium group.

[0484] In some embodiments, in the first host of Formula IV*, the first host comprises at least one chemical moiety selected from the group consisting of the structures in List 1* defined herein;

[0485] where Y T , Y U , Y V and Y W Each independently selected from the group consisting of BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR' and GeRR';

[0486] Among them, each R T can be the same or different, and each R T is independently a donor, an acceptor group, an organic linker bonded to a donor, an organic linker bonded to an acceptor group, or a terminal group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an aryl group, a heteroaryl group, and combinations thereof; and

[0487] R and R' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof.

[0488] In some embodiments, in the first host of Formula IV*, the first host is selected from the structures consisting of the structures in List 4* defined herein and the following structures:

[0489]

[0490] Where X 1 To X 45 each independently is C or N;

[0491] Among them, each R A , R AA , R B , R C , R D , R E , R F and R G Independently represents a single substitution to the maximum number of substitutions allowed, or no substitution;

[0492] Where R A , R AA , R B , R C , R D , R E and R F Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0493] In some embodiments, in the first host of Formula IV*, the first host is selected from the structures consisting of the structures in List 5* defined herein and the following structures:

[0494]

[0495] In some embodiments, in the first host of Formula IV*, the first host is selected from the group consisting of compounds in List 6* as defined herein and the following compounds.

[0496]

[0497]

[0498] In some embodiments, the phosphorescent material has a structural formula selected from the group consisting of: Ir(L A )3、Ir(L A )(L B )2、Ir(L A )2(L B )、Ir(L A )2(L C )、Ir(L A )(L B )(L C ) and Pt(L A )(L B );

[0499] Where L A , L B and L C They are different from each other in Ir compounds;

[0500] Where L A and L B may be the same or different in the Pt compound; and

[0501] Where L A and L B Capable of linking to form a tetradentate ligand in the Pt compound.

[0502] In some embodiments, the phosphorescent material is selected from the group consisting of the following dopant group 1:

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509] in

[0510] X 96 To X 99 Each of is independently C or N;

[0511] Each Y 100 Independently selected from the group consisting of: NR", O, S and Se;

[0512] R 10a , R 20a , R 30a , R 40a and R 50a Each of the above independently represents mono- to maximal substitution, or no substitution;

[0513] R, R', R", R 10a , R 11a , R 12a , R 13a , R 20a , R 30a , R 40a , R 50a , R 60 , R 70 , R 97 , R 98 and R 99 Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; any two substituents can be joined or fused to form a ring.

[0514] In some embodiments, the phosphorescent material is selected from the group consisting of the following dopant group 2:

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523] in:

[0524] Each Y 100 Independently selected from the group consisting of: NR", O, S and Se;

[0525] L is independently selected from the group consisting of a direct bond, BR", BR"R"', NR", PR", O, S, Se, C=O, C=S, C=Se, C=NR", C=CR"R"', S=O, SO2, CR", CR"R"', SiR"R"', GeR"R"', alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

[0526] X 100 and X 200 at each occurrence selected from the group consisting of: O, S, Se, NR" and CR"R"';

[0527] Each R A" , R B" , R C" , R D" , R E" and R F" independently represents mono- to maximum-substitution, or no substitution;

[0528] R, R', R", R'', R A1 '、R A2 '、R A" , R B" , R C" , R D" , R E" , R F" , R G" , R H" , R I" , R J" , R K" , R L" , R M" and R N" Each of is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; any two substituents can be joined or fused to form a ring.

[0529] In some embodiments of the above dopant groups 1 and 2, each unsubstituted aromatic carbon atom may be replaced by N to form a nitrogen heterocycle. In some embodiments, the maximum number of N atoms in one ring is 1 or 2. In some embodiments of the above dopant group 2, each Pt atom in the formula may be replaced by a Pd atom.

[0530] In some embodiments of the OLED, the delayed fluorescent material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescent material is a metal complex. In some embodiments, the delayed fluorescent material is a non-metallic complex. In some embodiments, the delayed fluorescent material is a Zn, Cu, Ag or Au complex.

[0531] In some embodiments of OLEDs, the delayed fluorescent material has the formula M(L 5 )(L 6 ), where M is Cu, Ag or Au, L 5 and L 6 Different, and L 5 and L 6 Independently selected from the group consisting of:

[0532]

[0533]

[0534] Among them A 1 -A 9 are each independently selected from C or N;

[0535] Each R P , R Q and R U independently represents mono- to maximum-substitution, or no substitution;

[0536] Among them, each R P , R P , R U , R SA , R SB , R RA , R RB , R RC , R RD , R RE and R RF is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; any two substituents can be joined or fused to form a ring.

[0537] In some embodiments of the OLED, the delayed fluorescent material comprises at least one of the donor moieties selected from the group consisting of:

[0538]

[0539]

[0540] where Y T , Y U , Y V and Y W Each is independently selected from the group consisting of B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO2.

[0541] In some of the above embodiments, any carbon ring atom, up to a total of three carbon ring atoms together with their substituents, in each benzene ring of any of the above structures can be replaced by N.

[0542] In some embodiments, the delayed fluorescent material comprises at least one of an acceptor moiety selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor moiety and the donor moiety as described herein can be directly linked, via a conjugated linker or a non-conjugated linker (such as sp 3 carbon or silicon atoms).

[0543] In some embodiments, the fluorescent material comprises at least one of the chemical moieties selected from the group consisting of:

[0544]

[0545]

[0546] where Y F , Y G , Y H and Y I Each independently selected from the group consisting of: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O and SO2;

[0547] Where X F and X G are each independently selected from the group consisting of C and N.

[0548] In some of the above embodiments, any carbon ring atom, up to a total of three carbon ring atoms together with their substituents, in each benzene ring of any of the above structures can be replaced by N.

[0549] In another aspect, the OLED of the present disclosure may also include an emission region, the emission region containing a compound or a formulation of compounds as disclosed in the above compound section of the present disclosure. In some embodiments, the emission region may include a compound or a formulation of compounds according to [Replication Technical Solution 1]. In some embodiments, the emission region is composed of one or more organic layers, wherein at least one of the one or more organic layers has a minimum thickness selected from the group consisting of: 350, 400, 450, 500, 550, 600, 650 and In some embodiments, at least one of the one or more organic layers is formed of an emissive system having a figure of merit (FOM) equal to or greater than a value selected from the group consisting of: 2.50, 2.55, 2.60, 2.65, 2.70, 2.75, 2.80, 2.85, 2.90, 2.95, 3.00, 5.00, 10.0, 15.0, and 20.0. The definition of FOM can be found in U.S. Patent Application Publication No. 2023 / 0292605, and the entire contents are incorporated herein by reference. In some embodiments, at least one of the one or more organic layers comprises a compound or formulation of a compound as disclosed in Sections A and D of the present disclosure.

[0550] In some embodiments, the OLED or emission region comprising the compounds of the present invention disclosed herein can be incorporated into a full-color pixel arrangement of a device. The full-color pixel arrangement of such a device includes at least one pixel, wherein the at least one pixel includes a first sub-pixel and a second sub-pixel. The first sub-pixel includes a first OLED, which includes a first emission region. The second sub-pixel includes a second OLED, which includes a second emission region. In some embodiments, the first and / or second OLED, the first and / or second emission regions may be the same or different and each may independently have various device features and various embodiments of the compounds of the present invention included therein, as well as various combinations and sub-combinations of various device features and various embodiments of the compounds of the present invention included therein, as disclosed herein.

[0551] In some embodiments, the first emission region is configured to emit a signal having a peak wavelength λ max1 The second emission region is configured to emit light having a peak wavelength λ max2 In some embodiments, the peak wavelength λ max1 With λ max2 The difference between is at least 4 nm but within the same color. For example, light blue and dark blue light as described above. In some embodiments, the first emission region is configured to emit a light having a peak wavelength λ in one region of the visible spectrum of 400-500 nm, 500-600 nm, 600-700 nm. max1 and the second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum of 400-500nm, 500-600nm, 600-700nm max2light. In some embodiments, the first emission region comprises (if more than one) a first number of emission layers deposited one above the other; and the second emission region comprises (if more than one) a second number of emission layers deposited one above the other; and the first number is different from the second number. In some embodiments, both the first emission region and the second emission region comprise phosphorescent materials, which may be the same or different. In some embodiments, the first emission region comprises a phosphorescent material and the second emission region comprises a fluorescent material. In some embodiments, both the first emission region and the second emission region comprise fluorescent materials, which may be the same or different.

[0552] In some embodiments, at least one pixel of an OLED or an emissive region comprises a total of N subpixels; wherein the N subpixels comprise a first subpixel and a second subpixel; wherein each of the N subpixels comprises an emissive region; wherein the total number of emissive regions within at least one pixel is equal to or less than N-1. In some embodiments, the second emissive region is identical to the first emissive region; and each subpixel of at least one pixel comprises an emissive region that is identical to the first emissive region. In some embodiments, a full-color pixel arrangement may have a plurality of pixels comprising a first pixel region and a second pixel region; wherein at least one display feature in the first pixel region is different from a corresponding display feature in the second pixel region, and wherein at least one display feature is selected from the group consisting of: resolution, cavity mode, color, outcoupling, and color filter.

[0553] In some embodiments, the OLED is a stacked OLED comprising one or more charge generation layers (CGLs). In some embodiments, the OLED comprises a first electrode, a first emission region disposed above the first electrode, a first CGL disposed above the first emission region, a second emission region disposed above the first CGL, and a second electrode disposed above the second emission region. In some embodiments, the first emission region and / or the second emission region may have various device features as described above for pixelated devices. In some embodiments, the stacked OLED is configured to emit white. In some embodiments, one or more of the emission regions in the pixelated OLED or stacked OLED comprises a sensitizer and an acceptor having various sensitizing device features and various embodiments of the compounds of the present invention disclosed herein. For example, the first emission region is included in the sensitizing device, while the second emission region is not included in the sensitizing device; in some cases, both the first emission region and the second emission region are included in the sensitizing device.

[0554] In some embodiments, the OLED can emit light having at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99% or 100% from a plasmon mode. In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emission layer is used as an enhancement layer. The enhancement layer comprises a plasmon material exhibiting a surface plasmon resonance, the plasmon material non-radiatively couples to the emitter material, and transfers excited state energy from the emitter material to a non-radiative mode of a surface plasmon polariton. In some embodiments, the enhancement layer is disposed at a distance from the organic emission layer that does not exceed a threshold distance, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer. The threshold distance is the position where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. Another threshold distance is the distance at which the total radiative decay rate constant divided by the sum of the total non-radiative decay rate constant and the total radiative decay rate constant is equal to the photoluminescence yield of the emitting material in the absence of the enhancement layer.

[0555] In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on a side above the enhancement layer opposite to the organic emission layer. The outcoupling layer scatters energy from surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, energy is scattered from the surface plasmon mode of the device into other modes, such as but not limited to an organic waveguide mode, a substrate mode, or another waveguide mode. In some embodiments, one or more intermediate layers may be disposed between the enhancement layer and the outcoupling layer. Examples of intermediate layers may be dielectric materials, including organic, inorganic, perovskite, oxides, and may include stacks and / or mixtures of these materials.

[0556] The enhancement layer changes the effective properties of the medium in which the emitter material resides, causing any or all of the following: reduced emissivity, changed emission line shape, variation in emission intensity with angle, changed emitter material stability, changed OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both, or placing the enhancement layer itself as a CGL, produces an OLED device that utilizes any of the above effects. In addition to the specific functional layers described in the various OLED examples mentioned herein and shown in the figures, the OLED according to the present disclosure may also include any other functional layers commonly found in OLEDs.

[0557] In some embodiments, the enhancement layer may include a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. In some embodiments, the plasmonic material includes at least one metal. In such embodiments, the metal may include at least one of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, or Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the enhancement layer is configured as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or has sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged.

[0558] In some embodiments, the outcoupling layer has wavelength-sized features or sub-wavelength-sized features that are arranged periodically, quasi-periodically, or randomly. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles. In some embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the outcoupling layer may be adjusted by at least one of: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer, or changing the material of the enhancement layer. The plurality of nanoparticles of the device may be formed of at least one of: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layering of one or more materials, and / or a core of one type of material and coated with a shell of another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the outcoupling layer is formed by photolithography.

[0559] In some embodiments of plasmonic devices, the emitter and / or host compound used in the emissive layer has a vertical dipole ratio (VDR) of 0.33 or greater. In some such embodiments, the emitter and / or host compound has a VDR of 0.40, 0.50, 0.60, 0.70, or greater.

[0560] In yet another aspect, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound or a formulation of compounds as disclosed in the above compound section of the present disclosure.

[0561] 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 include technical solution 1 as described herein.

[0562] In general, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When an electric current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When electrons and holes are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair with an excited energy state. When the exciton relaxes through a light emission mechanism, light is emitted. In some cases, the exciton can be localized into an excimer or an excited complex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0563] Figure 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer (HIL) 120, a hole transport layer (HTL) 125, an electron blocking layer (EBL) 130, an emission layer (EML) 135, a hole blocking layer (HBL) 140, an electron transport layer (ETL) 145, an electron injection layer (EIL) 150, a protective layer 155, a cathode 160, and a barrier layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 can be manufactured by depositing the layers in sequence. The properties and functions of these various layers and example materials are described in more detail in US 7,279,704, columns 6-10, which are incorporated by reference.

[0564] More examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes comprising a composite cathode having a thin layer of a metal (e.g., Mg:Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0565] Figure 2 An inverted OLED 200 is shown. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 can be manufactured by depositing the layers in order. Because the most common OLED configuration has a cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 An example is provided of how some layers may be omitted from the structure of device 100 .

[0566] Figure 1 and 2The simple layered structures described in are provided by way of non-limiting examples, and it should be understood that embodiments of the present disclosure may be used in conjunction with various other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be obtained by combining the various layers described in different ways, or the layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than the specifically described materials may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it should be understood that a combination of materials may be used, such as a mixture of a host and a dopant, or more generally, a mixture. In addition, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, the OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, Figure 1 and 2 Multiple layers of said different organic materials.

[0567] Structures and materials not specifically described may also be used, such as OLEDs containing polymeric materials (PLEDs), such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of another example, an OLED having a single organic layer may be used. OLEDs may be stacked, such as described in U.S. Pat. No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from Figure 1 and 2 For example, the substrate may include angled reflective surfaces to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and / or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0568] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet (as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (as described in U.S. Pat. No. 6,337,102 to Forrest et al., incorporated by reference in their entirety), and deposition by organic vapor jet printing (OVJP, also referred to as organic vapor jet deposition (OVJD)) (as described in U.S. Pat. No. 7,431,968, incorporated by reference in their entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in nitrogen or an inert atmosphere. For other layers, preferred methods include thermal evaporation, sputtering, chemical vapor deposition, atomic layer deposition, and electron beam deposition. Preferred patterning methods include deposition through a mask, photolithography, and cold welding (as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety) and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to make it compatible with a specific deposition method. For example, branched or unbranched, preferably containing at least 3 carbons, such as alkyl and aryl substituents, may be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 or more carbons may be used, and 3 to 20 carbons are a preferred range. Materials having asymmetric structures may have better solution processability than materials having symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0569] The device manufactured according to the embodiment of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrode and the organic layer from exposure to harmful substances in an environment including moisture, vapor and / or gas, etc. The barrier layer can be deposited on the substrate, the electrode, under the substrate, the electrode, or beside the substrate, the electrode, or on any other part of the device (including the edge). The barrier layer may include a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques and may include a composition having a single phase and a composition having multiple phases. Any suitable material or material combination can be used for the barrier layer. The barrier layer may be combined with an inorganic compound or an organic compound or both. The preferred barrier layer includes a plurality of alternative layers of polymeric materials and non-polymeric materials; organic materials and inorganic materials; or a mixture of polymeric materials and non-polymeric materials, as described in an example in U.S. Patent No. 7,968,146, PCT Patent Application No. PCT / US2007 / 023098 and No. PCT / US2009 / 042829, which are incorporated herein by reference in their entirety.

[0570] The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of electronic component modules (or units), which can be incorporated into a variety of electronic products or intermediate components. Examples of the electronic products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels), etc. that can be utilized by end-user product manufacturers. The electronic component module may optionally include driving electronic devices and / or power supplies. The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of consumer products, and the consumer products have one or more electronic component modules (or units) incorporated therein. A consumer product comprising an OLED is disclosed, and the OLED includes a compound of the present disclosure in an organic layer in the OLED. The consumer product should include any kind of product containing one or more of one or more light sources and / or a certain type of visual display. Some examples of consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, phones, cellular phones, tablet computers, tablet phones, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices, and signage. Various control mechanisms can be used to control devices manufactured according to the present disclosure, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18°C ​​to 30°C, and more preferably at room temperature (20-25°C), but can be used outside this temperature range (e.g., -40°C to +80°C).

[0571] More details regarding OLEDs and the definitions set forth above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0572] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can employ the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0573] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes. In some embodiments, the OLED further comprises one or more quantum dots. These quantum dots can be in the emission layer, or in other functional layers, such as downconversion layers.

[0574] In some embodiments, the OLED comprises an RGB pixel arrangement or a white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of ​​at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0575] D. Other materials used in OLED

[0576] The materials described herein are various examples of specific layers that can be used in OLEDs. They can also be used in combination with a wide variety of other materials present in the device. For example, the host materials disclosed herein can be used by the host materials in the EML themselves, or in combination with a wide variety of other emitters, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds and devices disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0577] a) Conductive dopants:

[0578] The charge transport layer can be doped with a conductivity dopant to substantially change its charge carrier density, which in turn will change its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductivity dopant, and an n-type conductivity dopant is used in the electron transport layer. In some embodiments, the conductive dopant comprises at least one chemical moiety selected from the group consisting of: a cyano group, a fluorinated aryl or heteroaryl group, a fluorinated alkyl or cycloalkyl group, an alkylene group, a heteroaryl group, an amide, a benzodithiophene, and a highly conjugated heteroaryl group extended by a non-cyclic double bond.

[0579] b)HIL / HTL:

[0580] The hole injection / transport material used in the present disclosure is not particularly limited, and any compound can be used as long as the compound is generally used as a hole injection / transport material. Examples of the material include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolecarbazole derivatives; polymers containing fluorocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x ; p-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile; metal complexes; and crosslinkable compounds.

[0581] Examples of aromatic amine derivatives for use in HIL or HTL include, but are not limited to, the following general structure:

[0582]

[0583] Ar 1 To Ar 9 Each of the following is selected from the group consisting of aromatic hydrocarbon cyclic compounds: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units, which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are directly or via at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups. Ar 1 To Ar 9 Each of may be unsubstituted or may be substituted with a general substituent as described above, and any two substituents may be joined or fused to form a ring.

[0584] In some embodiments, each Ar 1 To Ar 9 independently comprising a portion selected from the group consisting of:

[0585]

[0586] Where k is an integer from 1 to 20; X 101 To X 108 is C or N; Z 101 is C, N, O or S.

[0587] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0588]

[0589] Where Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 The coordinating atoms of L are independently selected from C, N, O, P and S; 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0590] In some embodiments, (Y 101 -Y 102 ) is a 2-phenylpyridine or 2-phenylimidazole derivative. In some embodiments, (Y 101 -Y 102 ) is a carbene ligand. In some embodiments, Met is selected from Ir, Pt, Pd, Os, Cu and Zn. In some embodiments, the metal complex has a relative + / Fc coupling has a minimum oxidation potential in solution of less than about 0.6 V.

[0591] In some embodiments, the HIL / HTL material is selected from the group consisting of phthalocyanine and porphyrin compounds, starburst triarylamines, CF x Fluorocarbon polymers, conductive polymers (e.g., PEDOT:PSS, polyaniline, polythiophene), phosphonic acid and silane SAMs, triarylamine or polythiophene polymers containing conductive dopants, organic compounds containing conductive inorganic compounds (such as molybdenum oxide and tungsten oxide), n-type semiconductive organic complexes, metal organic metal complexes, crosslinkable compounds, polymers and copolymers based on polythiophene, triarylamines, triarylamines containing spirofluorene cores, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indolecarbazoles, isoindole compounds and metal carbene complexes.

[0592] c) EBL:

[0593] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can produce substantially higher efficiency and / or longer lifetimes than similar devices lacking a blocking layer. In addition, a blocking layer can be used to confine emission to desired areas of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO energy level of the compound used in the EBL is shallower than the HOMO energy level of one or more of the hosts in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional group as used in one of the hosts described below.

[0594] d) Other entities:

[0595] The light-emitting layer of the organic EL device of the present disclosure preferably contains at least a light-emitting material as a dopant, and a host material. Examples of host materials 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. In some embodiments, the emission layer may include two hosts: a first host and a second host. In some embodiments, the first host is a hole transport host, and the second host is an electron transport host. In some embodiments, the first host is a hole transport host, and the second host is a bipolar host. In some embodiments, the first host is an electron transport host, and the second host is a bipolar host. In some embodiments, the first host and the second host may form an exciplex. In some embodiments, the emission layer may include a third host. In some embodiments, the third host is selected from the group consisting of: an insulating host (wide bandgap host), a hole transport host, and an electron transport host. In some embodiments, the third host forms an exciplex with one of the first host and the second host or with both the first host and the second host. In some embodiments, the emission layer may include a fourth host. In some embodiments, the fourth host is selected from the group consisting of: an insulating host (wide bandgap host), a hole transport host, and an electron transport host. In some embodiments, the fourth host forms an excited complex with one of the first host, the second host and the third host, with two of the first host, the second host and the third host or with each of the first host, the second host and the third host. In some embodiments, the LUMO of the electron transport host is less than -2.4eV, less than -2.5eV, less than -2.6eV or less than -2.7eV. In some embodiments, the HOMO of the hole transport host is higher than -5.6eV, higher than -5.5eV, higher than -5.4eV or higher than -5.35eV. HOMO and LUMO values ​​can be determined using solution electrochemistry. A CH Instruments model 6201B potentiostat can be used to perform solution cyclic voltammetry and differential pulse voltammetry with anhydrous dimethylformamide (DMF) solvent and tetrabutylammonium hexafluorophosphate as supporting electrolytes. Glassy carbon, platinum wire and silver wire are used as working electrode, counter electrode and reference electrode, respectively. The electrochemical potential can be referenced to the internal ferrocene-ferrocenium redox couple (Fc / Fc+) by measuring the peak potential difference by differential pulse voltammetry.The corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were determined by reference to the cationic and anionic redox potentials of ferrocene (4.8 eV vs. vacuum) according to 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, J. Adv. Mater. 1995, 7, 551).

[0596] In some embodiments, the compounds of the invention described herein may be used as one of the subjects described above, and the compounds described below may be used as one or more of the other subjects described above.

[0597] Examples of metal complexes used as one or more other hosts preferably have the following general formula:

[0598]

[0599] Where Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 The coordinating atoms of L are independently selected from C, N, O, P and S; 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0600] In some embodiments, the metal complex is:

[0601]

[0602] where (ON) is a bidentate ligand with a metal coordinated to O and N atoms.

[0603] In some embodiments, Met is selected from Ir and Pt. In other embodiments, (Y 103 -Y 104 ) is a carbene ligand.

[0604] In some embodiments, the one or more other entities contain at least one selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene and azulene; a group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, aza -dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-carbazole, aza-indolocarbazole, aza-triphenylene, aza-tetraphenylene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene; and a group consisting of 2 to 10 cyclic structural units, the cyclic structural units are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are directly or via at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups. Each option in each group may be unsubstituted or may be substituted with a general substituent as described herein or may be further condensed.

[0605] In some embodiments, the one or more other bodies include at least one of the parts selected from the group consisting of:

[0606]

[0607]

[0608] Where k is an integer from 0 to 20 or from 1 to 20. 101 To X 108 Z is independently selected from C or N. 101 and Z 102 are independently selected from C, N, O or S.

[0609] In some embodiments, the one or more other hosts are selected from the group consisting of: aryl carbazoles, metal 8-hydroxyquinolinates (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic fused rings, zinc complexes, Compounds, aryltriphenylene compounds, poly-fused heteroaryl compounds, donor-acceptor molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., PVK), spirofluorene compounds, spirofluorene-carbazole compounds, indolecarbazole, 5-membered electron-deficient heterocycles (e.g., triazole, oxadiazole), tetraphenylene complexes, metal phenoxypyridine compounds, metal coordination complexes (e.g., Zn, Al containing N^N ligands), dibenzothiophene / dibenzofuran-carbazole compounds, silicon / germanium aromatic compounds, aromatic benzoyl esters, carbazoles connected by non-conjugated groups, aza-carbazole / dibenzofuran / dibenzothiophene compounds and high triplet metal organic metal complexes (e.g., metal-carbene complexes).

[0610] In some embodiments, the one or more other hosts comprise at least one chemical group selected from the group consisting of triphenylene, carbazole, indolecarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, azacyclohexaborane, oxaborabine, dihydroacridine, xanthene, dihydrobenzazasilane, dibenzooxasilane, phenoxazine, phenoxathiol, phenothiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrol, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, silane, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole and aza-(5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene).

[0611] In some embodiments, the one or more other bodies can be selected from the group consisting of structures in the following body group 1:

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618] in:

[0619] Each of J1 to J6 is independently C or N;

[0620] L' is a direct bond or an organic linker;

[0621] Each Y AA , Y BB , Y CC and Y DD independently selected from the group consisting of: absent, bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0622] R A '、R B '、R C '、R D '、R E '、R F ' and R G Each of ' independently represents mono-substituted to maximum substitution, or no substitution;

[0623] Each R, R', R A '、R B '、R C '、R D '、R E '、R F ' and R G ' is independently hydrogen or a substituent selected from the group consisting of general substituents as defined herein; any two substituents can be joined or fused to form a ring;

[0624] Also, where possible, each unsubstituted aromatic carbon atom is optionally replaced with N to form an aza-substituted ring.

[0625] In some embodiments, at least one of J1 to J3 is N, in some embodiments, at least two of J1 to J3 are N, and in some embodiments, all three of J1 to J3 are N. In some embodiments, each Y CC and Y DD Preferred are O, S and SiRR', and more preferred are O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen heterocycle.

[0626] In some embodiments, the host is selected from the group consisting of EG1-MG1-EG1 to EG53-MG27-EG53 of formula EGa-MGb-EGc, or when MGb is absent, EG1-EG1 to EG53-EG53 of formula EGa-EGc, wherein a is an integer from 1 to 53, b is an integer from 1 to 27, and c is an integer from 1 to 53. The structures of EG1 to EG53 are shown below:

[0627]

[0628]

[0629] The structures of MG1 to MG27 are shown below:

[0630]

[0631] In the MGb structures presented above, the two bonding positions in the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24, and MG25 are labeled with numbers for identification purposes.

[0632] In some embodiments, the host can be any of its aza-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the host has the formula EGa-MGb-Egc and is selected from the group consisting of h1 to h112 defined by the following Host Group 2 List, wherein each of MGb, EGa, and EGc is defined as follows:

[0633] h MGb EGa Ec h MGb EGa Ec h MGb EGa Ec h1 MG1 EG3 EG36 h39 MG13 3-EG17 9-EG4 h77 MG23 EG3 EG4 h2 MG1 EG8 EG12 h40 MG13 3-EG17 9-EG13 h78 MG23 EG3 EG5 h3 MG1 EG13 EG14 h41 MG13 3-EG17 9-EG31 h79 MG23 EG4 EG4 h4 MG1 EG13 EG18 h42 MG13 3-EG17 9-EG45 h80 MG23 EG4 EG5 h5 MG1 EG13 EG25 h43 MG13 3-EG17 9-EG46 h81 MG24 2-EG1 10-EG33 h6 MG1 EG13 EG36 h44 MG13 3-EG17 9-EG48 h82 MG24 2-EG4 10-EG36 h7 MG1 EG22 EG36 h45 MG13 3-EG17 9-EG49 h83 MG24 2-EG21 10-EG36 h8 MG1 EG25 EG46 h46 MG13 3-EG32 9-EG31 h84 MG24 2-EG23 10-EG36 h9 MG1 EG27 EG46 h47 MG13 3-EG44 9-EG3 h85 MG25 2-EG1 9-EG33 h10 MG1 EG27 EG48 h48 MG14 3-EG13 5-EG45 h86 MG25 2-EG3 9-EG36 h11 MG1 EG32 EG50 h49 MG14 3-EG23 5-EG45 h87 MG25 2-EG4 9-EG36 h12 MG1 EG35 EG46 h50 MG15 EG3 EG48 h88 MG25 2-EG17 9-EG27 h13 MG1 EG36 EG45 h51 MG15 EG17 EG31 h89 MG25 2-EG17 9-EG36 h14 MG1 EG36 EG49 h52 MG15 EG31 EG36 h90 MG25 2-EG21 9-EG36 h15 MG1 EG40 EG45 h53 MG16 EG17 EG17 h91 MG25 2-EG23 9-EG27 h16 MG2 EG3 EG36 h54 MG17 EG17 EG17 h92 MG25 2-EG23 9-EG36 h17 MG2 EG25 EG31 h55 MG18 EG16 EG24 h93 MG26 EG1 EG9 h18 MG2 EG31 EG33 h56 MG18 EG16 EG30 h94 MG26 EG1 EG10 h19 MG2 EG36 EG45 h57 MG18 EG20 EG41 h95 MG26 EG1 EG21 h20 MG2 EG36 EG46 h58 MG19 EG16 EG29 h96 MG26 EG1 EG23 h21 MG3 EG4 EG36 h59 MG20 EG1 EG31 h97 MG26 EG1 EG26 h22 MG3 EG34 EG45 h60 MG20 EG17 EG18 h98 MG26 EG3 EG3 h23 MG4 EG13 EG17 h61 MG21 EG23 EG23 h99 MG26 EG3 EG9 h24 MG5 EG13 EG45 h62 MG22 EG1 EG45 h100 MG26 EG3 EG23 h25 MG5 EG17 EG36 h63 MG22 EG1 EG46 h101 MG26 EG3 EG26 h26 MG5 EG18 EG36 h64 MG22 EG3 EG46 h102 MG26 EG4 EG10 h27 MG6 EG17 EG17 h65 MG22 EG4 EG46 h103 MG26 EG5 EG10 h28 MG7 EG43 EG45 h66 MG22 EG4 EG47 h104 MG26 EG6 EG10 h29 MG8 EG1 EG28 h67 MG22 EG9 EG45 h105 MG26 EG10 EG10 h30 MG8 EG6 EG7 h68 MG23 EG1 EG3 h106 MG26 EG10 EG14 h31 MG8 EG7 EG7 h69 MG23 EG1 EG6 h107 MG26 EG10 EG15 h32 MG8 EG7 EG11 h70 MG23 EG1 EG14 h108 MG27 EG52 EG53 h33 MG9 EG1 EG43 h71 MG23 EG1 EG18 h109 - EG13 EG18 h34 MG10 4-EG1 2-EG37 h72 MG23 EG1 EG19 h110 - EG17 EG31 h35 MG10 4-EG1 2-EG38 h73 MG23 EG1 EG23 h111 - EG17 EG50 h36 MG10 EG1 EG42 h74 MG23 EG1 EG51 h112 - EG40 EG45 h37 MG11 4-EG1 2-EG39 h75 MG23 EG2 EG18 h38 MG12 1-EG17 9-EG31 h76 MG23 EG3 EG3

[0634] In the above table, EGa and EGc structures bonded to one of the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are annotated with a numerical prefix indicating their bonding position in the MGb structure.

[0635] e) Emitter materials in EML:

[0636] One or more emitter materials may be used in combination with the compounds or devices disclosed herein. The emitter material may be emissive or non-emissive in the current device as described herein. Examples of emitter materials are not particularly limited, and any compound may be used as long as the compound is capable of producing emission in a conventional OLED device. Examples of suitable emitter materials include, but are not limited to, compounds capable of producing emission via phosphorescence, non-delayed fluorescence, delayed fluorescence (especially thermally activated delayed fluorescence, i.e., TADF (also known as E-type delayed fluorescence)), triplet-triplet annihilation, or a combination of these methods.

[0637] f)HBL:

[0638] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in substantially higher efficiency and / or longer lifetime than a similar device lacking the blocking layer. In addition, a blocking layer can be used to confine emission to a desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than one or more emitters closest to the HBL interface.

[0639] In some embodiments, the compounds used in HBL contain the same molecules or the same functional groups as used in the subjects described above.

[0640] In some embodiments, the compound used in the HBL comprises at least one of the following moieties selected from the group consisting of:

[0641]

[0642] Where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0643] g)ETL:

[0644] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.

[0645] In some embodiments, the compounds used in the ETL comprise at least one of the following moieties in the molecule:

[0646] and fullerene; wherein k is an integer from 1 to 20, X 101 To X 108 Selected from C or N; Z 101 Selected from the group consisting of C, N, O and S.

[0647] In some embodiments, the metal complex used in the ETL contains (but is not limited to) the following general formula:

[0648]

[0649] wherein (ON) or (NN) is a bidentate ligand having a metal coordinated to atoms O, N or N, N; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.

[0650] In some embodiments, the ETL material is selected from the group consisting of anthracene-benzimidazole compounds, azatriphenylene derivatives, anthracene-benzothiazole compounds, metal 8-hydroxyquinolinates, metal hydroxybenzoquinolinates, bathocuprine compounds, 5-membered electron-deficient heterocycles (e.g., triazole, oxadiazole, imidazole, benzimidazole), thiole compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0651] h) Charge Generation Layer (CGL)

[0652] In a tandem or stacked OLED, the CGL plays a fundamental role in the performance and consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and electrodes. The electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; then, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductivity dopants used in the transport layer.

[0653] In any compound disclosed herein, hydrogen atoms can be partially or completely deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99% and 100%. As used herein, the deuteration percentage has its common meaning and includes the percentage of all possible hydrogens and deuterium atoms replaced by deuterium atoms. In certain embodiments, the deuterium atom is connected to an aromatic ring. In certain embodiments, the deuterium atom is connected to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atom is connected to a heteroatom, such as a Si or Ge atom.

[0654] It should be understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the present invention. For example, other materials and structures may be used to replace many materials and structures described herein without departing from the spirit of the present invention. The present invention as required may therefore include variations of specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

[0655] Experimental data

[0656]

[0657] A suspension of carbazole-d8 (37.78 g, 215.6 mmol, 2.5 eq.), cesium carbonate (112.4 g, 344.9 mmol, 4.0 eq.) and 2-bromo-1,3-difluorobenzene-4,5,6-d3 (16.90 g, 86.22 mmol, 1.0 eq.) in N-methyl-2-pyrrolidone (180.0 mL) was bubbled with nitrogen for 10 minutes. After heating at 80 ° C. for 18 hours, the reaction mixture was cooled to room temperature and poured into water (3.5 L). The resulting solid was filtered and washed with water (1 L), then sublimed to remove excess carbazole. This crude brown material was adsorbed onto silica gel and purified by column chromatography eluting with dichloromethane and hexanes to afford 9,9'-(2-bromo-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (14.4 g, 33% yield) as a white solid.

[0658]

[0659] A solution of 9,9'-(2-bromo-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.0 g, 19.7 mmol, 1.0 eq) in anhydrous THF (100 mL) was bubbled with nitrogen for 15 minutes and cooled to -78 °C. A 2.5 M solution of n-butyl lithium in hexane (8.7 g, 21.7 mmol, 1.1 eq) was added dropwise over 10 minutes and the mixture was stirred at -78 °C for 1 hour. A solution of cyanuric chloride (5.5 g, 29.6 mmol, 1.5 eq) in anhydrous THF (20 mL) was then added and the mixture was slowly warmed to room temperature and stirred for 1 hour. The reaction mixture was then poured into methanol (400 mL). The resulting solid was filtered, washed with methanol (2 x 100 mL) and dried on the filter to afford 9,9'-(2-(4,6-dichloro-1,3,5-triazine-2-yl)-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.3 g, 90% yield) as a yellow solid.

[0660]

[0661] A solution of 9H-carbazole-d8 (2.9 g, 16.5 mmol, 0.95 eq) in anhydrous THF (150 mL) was bubbled with nitrogen for 15 minutes. A 60% dispersion of sodium hydride in mineral oil (0.83 g, 20.8 mmol, 1.2 eq) was added and the mixture was stirred for 30 minutes. The mixture was then cooled to -78 °C and 9,9'-(2-(4,6-dichloro-1,3,5-triazine-2-yl)-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.0 g, 17.4 mmol, 1.0 eq) was added in one portion. After stirring at -78 °C for 1 hour, the mixture was slowly warmed to room temperature. The reaction was quenched with saturated ammonium chloride (100 mL) and then diluted with water (500 mL). The mixture was then extracted with dichloromethane (2×500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was then recrystallized in a mixture of dichloromethane (100 mL) and methanol (130 mL) to give 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.1 g, 81% yield) as a yellow solid.

[0662]

[0663] A solution of 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazin-2-yl)-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (9.0 g, 12.6 mmol, 1.0 equiv), (phenyl-d5)boronic acid (2.4 g, 18.9 mmol, 1.5 equiv) and tripotassium phosphate (5.3 g, 25.2 mmol, 2.0 equiv) in a mixture of dioxane (80 mL) and water (16 mL) was bubbled with nitrogen for 15 minutes. 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.46 g, 0.63 mmol, 0.05 equiv) was added while continuing to bubble with nitrogen for an additional 5 minutes. After heating at 80 ° C overnight, the reaction mixture was cooled to room temperature and diluted with dichloromethane (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (250 mL). The combined organic layer was washed with saturated brine (250 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was eluted with dichloromethane and hexane and purified by column chromatography to give compound H1 (4.7 g, 49% yield) as a yellow solid.

[0664]

[0665] 9,9'-(2-(4,6-dichloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) was prepared in the same manner as 9,9'-(2-bromo-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8)

[0666] A suspension of 9,9'-(2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.0 g, 17.5 mmol, 1.0 equiv), 4,4,5,5-tetramethyl-2-(5,5,8,8-tetrakis(methyl-d3)-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-d7)-1,3,2-dioxaborolane (12.8 g, 38.4 mmol, 2.2 equiv) and potassium carbonate (9.66 g, 69.8 mmol, 4.0 equiv) in THF (120 mL) and water (20 mL) was bubbled with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (1.00 g, 0.87 mmol, 0.05 equiv) was added while bubbling nitrogen continuously for an additional 5 minutes. After heating at 70 °C for 18 hours, the reaction mixture was cooled to room temperature and poured into a mixture of methanol (500 mL) and water (200 mL). The resulting solid was filtered and washed with water (2 x 100 mL) and methanol (100 mL). This material was then purified by column chromatography eluting with dichloromethane and hexanes to give Compound H2 (6.6 g, 41% yield) as a white solid.

[0667]

[0668] 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) was prepared in the same manner as 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene-4,5,6-d3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8)

[0669] 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (8.5 g, 12.0 mmol, 1.0 equiv), 4,4,5,5-tetramethyl-2-(5,5,8,8-tetra(methyl-d3)-5,6,7 A suspension of 1,4-dioxane (80 mL) and water (20 mL) was bubbled with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium ( 0) (0.69 g, 0.59 mmol, 0.05 eq.) while bubbling nitrogen continuously for an additional 5 minutes. After heating at 80 °C for 18 hours, the reaction mixture was cooled to room temperature and poured into a mixture of methanol (500 mL) and water (100 mL). The resulting solid was filtered and washed with water (2 × 100 mL) and methanol (2 × 100 mL). This material was purified by column chromatography eluted with dichloromethane and hexane. The fractions containing the product were combined and concentrated under reduced pressure. The residue was ground with a mixture of dichloromethane (150 mL) and methanol (150 mL) at 35 °C for 1 hour. The warm suspension was filtered, washed with methanol (2 × 50 mL) and the solid was dried at 50 °C under high vacuum for 6 hours to give compound H3 (8.8 g, 83% yield) as a white solid.

[0670]

[0671] To a dry three-necked flask equipped with a magnetic stir bar, carbazole-d8 (9.0 g, 51.4 mmol, 1.0 equiv), copper (I) iodide (4.89 g, 25.7 mmol, 0.5 equiv), N1,N1,N2,N2-tetramethylethane-1,2-diamine (2.98 g, 25.7 mmol, 0.5 equiv) and tripotassium phosphate (35.5 g, 154 mmol, 3.0 equiv) were added in sequence. The flask was evacuated and backfilled with nitrogen. This evacuation and backfilling procedure was repeated twice. 1,3-Dibromobenzene-d4 (37.0 g, 154 mmol, 3.0 equiv) and toluene (285 mL) were added under a nitrogen atmosphere. After heating at 108 ° C overnight, additional potassium phosphate (35.5 g, 154 mmol, 3.0 equiv), copper (I) iodide (4.89 g, 25.7 mmol, 0.5 equiv) and N1, N1, N2, N2-tetramethylethane-1,2-diamine (2.98 g, 25.7 mmol, 0.5 equiv) were added, and the mixture was heated at 108 ° C overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (600 mL) and water (300 mL). The layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluted with dichloromethane and hexanes to give 9-(3-bromophenyl-2,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (4.5 g, 26% yield) as a colorless gum.

[0672] Hexane containing 2.5M n-butyl lithium (23.7 mL, 59.2 mmol, 1.1 eq) was added to a solution of 9-(3-bromophenyl-2,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (18.0 g, 53.9 mmol, 1.0 eq) in THF (180 mL) at -78 °C. After stirring for 1.5 hours, trimethyl borate (18.0 mL, 161.5 mmol, 3.0 eq) was added and the mixture was gradually warmed to room temperature overnight. The reaction mixture was quenched with water (300 mL) and extracted with ethyl acetate (600 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Hexanes (300 mL) were added to the residue to produce a white precipitate, which was filtered and dried under high vacuum at room temperature for 20 minutes to afford (3-(9H-carbazol-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (11.5 g, 71% yield) as a white solid.

[0673]

[0674] A suspension of 9,9'-(2-(4-(9H-carbazol-9-yl-d8)-6-chloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (12.0 g, 16.9 mmol, 1.0 equiv), (3-(9H-carbazol-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (6.057 g, 20.2 mmol, 1.2 equiv) and potassium carbonate (5.1 g, 37.1 mmol, 2.2 equiv) in THF (402 mL) and water (68 mL) was bubbled with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.69 mmol, 0.1 equiv) was added while continuing to bubble with nitrogen for an additional 5 min. After heating at 72 ° C for 18 hours, the reactant was cooled to room temperature, and the reaction mixture was diluted with dichloromethane (900mL), toluene (300mL) and water (150mL). The solution was filtered through a diatomaceous earth pad (50g) and washed with dichloromethane (300mL). The layers were separated, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was completely dissolved in a mixture of dichloromethane (400mL), tetrahydrofuran (200mL) and toluene (200mL) at 90 ° C for 10 minutes, cooled to room temperature, and then concentrated to about 200mL. The clear solution was left standing at room temperature for 10 minutes. The resulting solid was filtered and dried overnight at 35 ° C under vacuum to obtain compound H4 (7.0g, 45% yield) as an off-white solid.

[0675]

[0676] Step 1: To a 1000 mL round bottom flask was added 2-bromo-1,3,5-trifluorobenzene 591-1 (10 g, 1 Eq, 47 mmol), 9H carbazole (40 g, 5.0 Eq, 0.24 mol), cesium carbonate (93 g, 6 Eq, 0.28 mol) and 1-methyl-2-pyrrolidone (300.0 mL). The reaction mixture was then heated to 80 °C in an oil bath and stirred overnight. The reaction mixture was cooled to room temperature and poured into water (500 mL) and ethyl acetate (500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×300 mL). The organic layers were combined, dehydrated over anhydrous MgSO4 and filtered. The solvent was removed on a rotary evaporator under vacuum at 50 °C to give a solid product. The crude product was purified on silica gel using dichloromethane / heptane to give a white solid with excess carbazole. In a 1000mL round-bottom flask, the crude mixture was dissolved in anhydrous dichloromethane (500.0mL). The reaction mixture was then cooled to 0°C in an ice bath and stirred under nitrogen. Then, anhydrous pyridine (130.9g, 134mL, 30Eq, 1.655mol) was added, followed by acetyl chloride (86.61g, 79mL, 20Eq, 1.103mol). The reaction mixture was slowly warmed to room temperature and stirred overnight. Then, the reaction mixture was cooled to room temperature and poured into cold water (1000mL) and dichloromethane (500mL). The layers were separated, and the aqueous layer was extracted with dichloromethane (3×250mL). The organic layers were combined, washed with saturated NaHCO3, dehydrated and filtered through anhydrous MgSO4. At 50°C, under vacuum, the solvent was removed on a rotary evaporator to obtain a brown solid product. The crude product was purified on silica gel using ethyl acetate and heptane to give 9,9',9"-(2-bromobenzene-1,3,5-triyl)tris(9H-carbazole) (13.5 g, 52.3% yield) as a white solid.

[0677] Step 2: Into a 250 mL round bottom flask was added 9,9',9"-(2-bromobenzene-1,3,5-triyl)tris(9H-carbazole) 591-2 (5.000 g, 1 Eq, 7.662 mmol) and dissolved in anhydrous THF (80.00 mL) (clear solution) and purged with nitrogen for 5 minutes. The reaction mixture was then cooled to 0 °C (ice bath) and a hexane solution of n-butyllithium (589.0 mg, 3.678 mL, 2.500 molar concentration, 1.2 Eq, 9.194 mmol) was added dropwise over 5 minutes. A light yellow solution was observed. The mixture was stirred at 0 °C for 1 hour and 15 minutes. An aliquot was quickly quenched with water and extracted with dichloromethane. To the above reaction mixture was added 2,4,6-trichloro-1,3,5-triazine (5.651 g, 4 Eq, 30.65mmol) in anhydrous THF (20.00mL) as a colorless clear solution. A bright yellow solution was formed. The reaction mixture was stirred for another 5 minutes and the ice bath was removed. The reaction mixture was stirred at room temperature for 30 minutes, heated to 60°C and stirred overnight. The reaction mixture was cooled to room temperature, and water (100mL) and ethyl acetate (100mL) were added to separate the layers. The aqueous layer was extracted with ethyl acetate (3×100mL). The organics were combined and dehydrated and filtered over anhydrous MgSO4. The solvent was removed on a rotary evaporator under vacuum at 50°C. The crude product was purified on silica gel using dichloromethane and heptane to give a bright yellow solid 9,9',9"-(2-(4,6-dichloro-1,3,5-triazine-2-yl)benzene-1,3,5-triyl)tris(9H carbazole) (3.0g, 54.4% yield).

[0678] Step 3: To a 100 mL round-bottom flask was added 9,9',9"-(2-(4,6-dichloro-1,3,5-triazin-2-yl)benzene-1,3,5-triyl)tris(9H-carbazole) (5.300 g, 1 Eq, 7.344 mmol), 9H-carbazole (3.070 g, 2.5 Eq, 18.36 mmol), cesium carbonate (5.982 g, 2.5 Eq, 18.36 mmol) and 1-methyl-2-pyrrolidone (200.0 mL). The reaction mixture was stirred at 4 °C for 2 h. In an oil bath, heat to 100 ° C and stir overnight. The reaction mixture is cooled to room temperature, and water (100 mL) and ethyl acetate (200 mL) are added to the reaction mixture. Each layer is separated, and the aqueous layer is extracted with ethyl acetate (3×100 mL). The organic matter is combined and dried over anhydrous Na2SO4 and filtered. At 50 ° C, under vacuum, the solvent is removed on a rotary evaporator. Dichloromethane and heptane are used on silica gel to purify the crude product to obtain white solid compound H5 (4.2 g, 58.2% yield).

[0679]

[0680] At -78 ° C, hexane containing 2.5 M n-butyl lithium (1.08 g, 6.7 mL, 16.9 mmol, 1.2 eq) was added dropwise to a degassed solution of 2-bromo-1,3-bis(methyl-d3)benzene-4,5,6-d3 (3.00 g, 15.5 mmol, 1.1 eq) in anhydrous THF (70 mL). After stirring for 1 hour, methyl THF containing 1.9 M zinc (II) chloride (2.30 g, 8.88 mL, 16.9 mmol, 1.2 eq) was added dropwise at -78 ° C, and the reaction mixture was gradually warmed to room temperature and stirred for 1 hour. To the reaction mixture was added a degassed solution of 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.0 g, 14.1 mmol, 1.0 equiv) in THF (70 mL) followed by tetrakis(triphenylphosphine)palladium(0) (0.825 g, 0.714 mmol, 0.05 equiv). The reaction mixture was then heated at 90 °C for 2 days. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL) and water (200 mL). The layers were separated and the aqueous layer was washed with dichloromethane (3 x 100 mL). The combined organic layer was passed through a silica gel pad (100 g) and a diatomaceous earth pad (50 g) and rinsed with dichloromethane (300 mL). The filtrate was concentrated to about 100 mL and hexane (300 mL) was added. The resulting precipitate was treated with ultrasound at 40 ° C for 30 minutes, filtered and washed with hexane (100 mL) to give 9,9'-(2-(4-(2,6-bis(methyl-d3)phenyl-3,4,5-d3)-6-(9H-carbazole-9-yl-d8)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) compound H6 (11.01 g, 99% yield) as an off-white solid.

[0681]

[0682] A mixture of 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (12.3 g, 17.3 mmol, 1.2 eq) and sodium tert-butoxide (2.07 g, 21.6 mmol, 1.5 eq) in anhydrous m-xylene (144 mL) was bubbled with nitrogen for 5 minutes. 9H-1,9'-bicarbazole-d8 was added to the mixture. 15(5.00 g, 14.4 mmol, 1.0 equiv) and (methanesulfonate-κO)[2'-(methylamino-κN)-2-biphenyl-κC 2 [Tris(2-methyl-2-propyl)phosphine]palladium PdP(tBu)3-G4 (0.426 g, 0.719 mmol, 0.05 equiv) was added and bubbling continued for an additional 5 minutes. After heating at 120 °C for 16 hours, the reaction mixture was cooled to room temperature and concentrated to about 10 mL. The crude mixture was then purified on silica gel using dichloromethane / hexanes to afford 9-(4-(2,6-bis(9H-carbazole-9-yl-d8)phenyl)--6-(9H-carbazole-9-yl-d8)-1,3,5-triazine-2-yl)-9H-1,9'-bicarbazole-1',2,2',3,3',4,4',5,5',6,6',7,7',8,8'-d8 as an off-white solid. 15 Compound H7 (4.24 g, 29% yield).

[0683]

[0684] 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (6.26 g, 8.80 mmol, 1.0 equiv) and 2-([1,1':3',1"-terphenyl]-5'-yl-d 13 A mixture of 4-(4-(4-(4-piperidin-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (3.90 g, 10.6 mmol, 1.2 equiv) and potassium carbonate (2.68 g, 19.4 mmol, 2.2 equiv) in 1,4-dioxane (200 mL) and water (22.2 mL) was bubbled with nitrogen for 5 minutes.

[0685] Tetrakis(triphenylphosphine)palladium(0) (1.01 g, 0.88 mmol, 0.1 eq) was added, and bubbling was continued for an additional 5 minutes, followed by heating to 72 °C for 40 hours. The reaction mixture was cooled to room temperature and diluted with water (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate (10 g), filtered and concentrated under reduced pressure. The residue was purified on silica gel using dichloromethane / hexanes, followed by recrystallization in dichloromethane and methanol to afford 9,9'-(2-(4-([1,1':3',1"-terphenyl]-5'-yl-d as a white solid. 13)-6-(9H-carbazole-9-yl-d8)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) compound H8 (6.1 g, 75% yield).

[0686]

[0687] A mixture of 9,9'-(2-(4-(9H-carbazol-9-yl-d8)-6-chloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (2.02 g, 2.85 mmol, 1.0 equiv) and 2-(3,5-di-tert-butylphenyl-2,4,6-d3)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g, 3.13 mmol, 1.1 equiv) and potassium carbonate (0.87 g, 6.3 mmol, 2.2 equiv) in THF (60 mL) and water (10 mL) was bubbled with nitrogen for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.33 g, 0.285 mmol, 0.1 eq.) was added and bubbling continued for an additional 5 minutes. The reaction was then heated at 72 °C for 16 hours. The reaction was combined with other consumptions and the combined reaction mixture was diluted with water (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate (20 g), filtered and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel using dichloromethane / hexanes and then recrystallized in methanol to give 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-(3,5-di-tert-butylphenyl-2,4,6-d3)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) Compound H9 (1.9 g) as an off-white solid.

[0688]

[0689] A mixture of 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (5.00 g, 7.03 mmol, 1.0 equiv), tris(phenyl-d5)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-2,4,5,6-d4)silane (3.37 g, 8.43 mmol, 1.2 equiv) and potassium carbonate (2.137 g, 15.5 mmol, 2.2 equiv) in dioxane (63 mL) and water (7.0 mL) was bubbled with nitrogen for 5 minutes.

[0690] Tetrakis(triphenylphosphine)palladium(0) (0.812 g, 0.703 mmol, 0.1 eq.) was added while bubbling with nitrogen for an additional 5 minutes. The reactants were heated at 80 °C for 5.5 hours. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL) and water (125 mL). The layers were separated and the organic layer was concentrated under reduced pressure. The residue was purified using dichloromethane / hexane on silica gel to give 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-(3-(tri(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) compound H10 (4.55 g, 63% yield) as a yellow solid.

[0691]

[0692] A mixture of 9,9'-(2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (15.0 g, 26.2 mmol, 1.0 equiv), 4,4,5,5-tetramethyl-2-(5,5,8,8-tetrakis(methyl-d3)-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-d7)-1,3,2-dioxaborolane (3.93 g, 11.79 mmol, 0.45 equiv), potassium carbonate (7.241 g, 52.40 mmol, 2.0 equiv) in THF (524 mL) and water (58 mL) was bubbled with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.514 g, 1.31 mmol, 0.05 equiv) was added while bubbling continuously for 5 minutes. After heating overnight at 45 °C, the reaction mixture was cooled to room temperature and diluted with dichloromethane (600 mL) and water (150 mL). The layers were separated, and the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using dichloromethane / hexanes on silica gel to give 9,9'-(2-(4-chloro-6-(5,5,8,8-tetrakis(methyl-d3)-5,6,7,8-tetrahydronaphthalene-2-yl-1,3,4,6,6,7,7-d7)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (2.5 g, 31% yield) as an off-white solid.

[0693]

[0694] A mixture of 9,9'-(2-(4-chloro-6-(5,5,8,8-tetrakis(methyl-d3)-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-d7)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (2.4 g, 3.23 mmol, 1.0 equiv), potassium carbonate (0.98 g, 7.1 mmol, 2.2 equiv) and (3-(9H-carbazole-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (1.16 g, 3.873 mmol, 1.2 equiv) was added to tetrahydrofuran (77 mL) and water (13 mL) and the mixture was bubbled with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (373.0 mg, 322.8 μmol, 0.1 eq.) was added while bubbling continued for an additional 5 minutes. After heating at 72° C. overnight, the reaction mixture was cooled to room temperature and diluted with dichloromethane (600 mL) and water (150 mL). The layers were separated. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel using dichloromethane / hexanes to give 9,9'-(2-(4-(3-(9H-carbazole-9-yl-d8)phenyl-2,4,5,6-d4)-6-(5,5,8,8-tetrakis(methyl-d3)-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-d7)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) Compound H11 (2.8 g, 90% yield) as a white solid.

[0695]

[0696] A solution of 9,9'-(2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (6.00 g, 10.5 mmol, 1.00 equiv), tripotassium phosphate (8.90 g, 41.9 mmol, 4.00 equiv) and (phenyl-d5)boronic acid (5.32 g, 41.9 mmol, 4.0 equiv) in 1,4-dioxane (105 mL) was bubbled with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.21 g, 1.05 mmol, 0.10 equiv) was added and the reaction mixture was heated to 100 °C for 4 hours. The reaction mixture was cooled to room temperature and diluted with water (50 mL) and dichloromethane (50 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate (10 g), filtered and concentrated under reduced pressure. The residue was purified on silica gel using dichloromethane / hexanes to afford 9,9′-(2-(4,6-bis(phenyl-d5)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) Compound H12 (5.21 g, 75% yield) as an off-white solid.

[0697]

[0698] A mixture of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (40.0 g, 228 mmol, 1.0 equiv) and N-iodosuccinimide (53.9 g, 240 mmol, 1.1 equiv) in acetic acid (1200 mL) was stirred at room temperature for 15 hours. The reaction mixture was poured into water (1 L). The resulting precipitate was filtered. The brown residue was then dissolved in ethyl acetate (1200 mL) and washed sequentially with saturated sodium bicarbonate (1.0 L) and saturated sodium thiosulfate (300 mL). The organic layer was dried over sodium sulfate (60 g), filtered and concentrated under reduced pressure. The residue was suspended in ethyl acetate (60 mL), heated to dissolve all solids, and then recrystallized at -40 ° C overnight. The crystals were filtered and washed with cold dichloromethane (100 mL) to give 3-iodo-9-carbazole-1,2,4,5,6,7,8-d7 (19.0 g, 28% yield) as white crystals.

[0699] A solution of 3-iodo-9H-carbazole-1,2,4,5,6,7,8-d7 (18.8 g, 62.6 mmol, 1.0 eq) in N,N-dimethylformamide (418 mL) was bubbled with nitrogen for 10 minutes. Dicyanozinc (11.0 g, 94.0 mmol, 1.5 eq) and tetrakis(triphenylphosphine)palladium(0) (7.24 g, 6.26 mmol, 0.1 eq) were added while bubbling continued for an additional 5 minutes. After heating at 80 °C overnight, the reaction mixture was cooled to room temperature and poured into water (20 mL), resulting in a precipitate. The precipitate was filtered and the solid residue was suspended in dichloromethane (500 mL). The solid was filtered off from the suspension and washed with dichloromethane (500 mL), the filtrate was concentrated and purified on silica gel using dichloromethane to give 9H-carbazole-3-carbonitrile-1,2,4,5,6,7,8-d7 (2.4 g, 19% yield) as a white solid.

[0700]

[0701] A mixture of 9,9′-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.7 g, 15.1 mmol, 1.2 equiv) and sodium tert-butoxide (1.81 g, 18.8 mmol, 1.5 equiv) in anhydrous THF (200 mL) was bubbled with nitrogen for 5 min. 9H-carbazole-3-carbonitrile-1,2,4,5,6,7,8-d7 (2.50 g, 12.6 mmol, 1.0 equiv) and (methanesulfonate-κO)[2'-(methylamino-κN)-2-biphenyl-κC2][tri(2-methyl-2-propyl)phosphine]palladium (P(tBu)3Pd-G4) (0.367 g, 0.627 mmol, 0.05 equiv) were added while bubbling continued for an additional 5 minutes. After heating at 70 °C for 2 days, the reaction mixture was cooled to room temperature, diluted with dichloromethane (600 mL), and then filtered. The filtrate was passed through a pad of silica gel (60 g) topped with celite (30 g) and rinsed with dichloromethane (500 mL). The filtrate was concentrated under reduced pressure. The residue was purified on silica gel using dichloromethane / hexanes to give 9-(4-(2,6-bis(9H-carbazol-9-yl-d8)phenyl)-6-(9H-carbazol-9-yl-d8)-1,3,5-triazine-2-yl)-9H-carbazole-3-carbonitrile-1,2,4,5,6,7,8-d7 Compound H13 (9.60 g, 88% yield) as an off-white solid.

[0702]

[0703] A suspension of 9,9'-(2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (8.5 g, 12.0 mmol, 1.0 equiv), (3-(9H-carbazole-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (5.98 g, 17.9 mmol, 1.5 equiv) and potassium carbonate (4.8 g, 34.6 mmol, 2.2 equiv) in THF (300 mL) and water (50 mL) was bubbled with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.6 mmol, 0.1 equiv) was added while continuing to bubble with nitrogen for an additional 5 min. After heating at 72 ° C for 18 hours, the reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized twice in a mixture of ethanol (400 mL) and toluene (80 mL) at room temperature for 1 hour. The recrystallized material was further purified on silica gel using dichloromethane / hexane to obtain 9,9'-(2-(4,6-bis(3-(9H-carbazole-9-yl-d8)phenyl-2,4,5,6-d4)-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) compound H14 (7.3 g, 46% yield) as a white solid.

[0704]

[0705] At 0°C, 2.5 M n-butyl lithium in hexane (12.1 mL, 30.4 mmol, 1.2 eq.) was added dropwise to 9H-3,9-bicarbazole-d 15(8.79 g, 25.3 mmol, 1.0 equiv) in anhydrous THF (180 mL). The reaction mixture was stirred at the temperature for 15 minutes and then warmed to room temperature. A solution of 9,9'-(2-(4-(9H-carbazole-9-yl-d8)-6-chloro-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (18.0 g, 25.3 mmol, 1.0 equiv) in anhydrous THF (140 mL) was then added to the above solution. After stirring at room temperature for 16 hours, the reaction mixture was quenched with methanol (500 mL) to cause precipitation. The solid was collected by filtration and purified on silica gel using dichloromethane / hexanes to afford 9-(4-(2,6-bis(9H-carbazol-9-yl-d8)phenyl)-6-(9H-carbazol-9-yl-d8)-1,3,5-triazine-2-yl)-9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d8 as a yellow solid. 15 Compound H15 (10.7 g, 41% yield).

[0706]

[0707] Step 1: A mixture of 2-bromo-1,3-difluoro-4-iodobenzene (17.1 g, 53.7 mmol, 1.0 equiv), cesium carbonate (52.5 g, 161 mmol, 3.0 equiv) and 9H-carbazole-d8 (19.3 g, 110 mmol, 2.05 equiv) in N-methyl-2-pyrrolidone (540 mL) was stirred at 100 °C for 16 hours. The reaction mixture was cooled to room temperature and quenched with water (500 mL), causing precipitation. The white solid was filtered and dissolved in warm dichloromethane (700 mL). This solution was passed through a plug of silica (90 g), washed with additional dichloromethane (800 mL) and the filtrate was concentrated under reduced pressure. The solid was redissolved in warm dichloromethane (250 mL) and methanol (100 mL) was added. The solution was concentrated to remove most of the dichloromethane, causing precipitation. The precipitate was filtered and dried to give 9,9'-(2-bromo-4-iodo-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (19.4 g, 57% yield) as a white solid.

[0708] Step 2: A mixture of 9,9'-(2-bromo-4-iodo-1,3-phenylene)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (19.4 g, 30.8 mmol, 1.0 equiv), (phenyl-d5)boronic acid (4.31 g, 33.9 mmol, 1.1 equiv) and potassium carbonate (8.52 g, 61.7 mmol, 2.0 equiv) in toluene (300 mL) and water (60 mL) was bubbled with nitrogen for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.78 g, 1.54 mmol, 0.05 equiv) was added while bubbling continued for an additional 15 minutes. After heating at 80 °C for 16 hours, additional catalyst (0.250 g) was added and heating was continued for an additional 3 days. The reaction mixture was cooled to room temperature and diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated. The organic layer was concentrated under reduced pressure to give an orange solid. This material was purified on silica gel using dichloromethane / hexanes to give 9,9'-(3-bromo-[1,1'-biphenyl]-2,4-diyl-2',3',4',5',6'-d5)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (13.1 g, 73% yield) as an off-white solid.

[0709] Step 3: 2.5 M n-butyl lithium in hexane (2.42 mL, 6.06 mmol, 2.0 equiv) was added dropwise to a solution of 9,9'-(3-bromo-[1,1'-biphenyl]-2,4-diyl-2',3',4',5',6'-d5)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (1.77 g, 3.03 mmol, 1.0 equiv) in anhydrous THF (23 mL) at 0°C. After stirring at 0°C for 1 hour, 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (1.40 g, 3.03 mmol, 1.0 equiv) was added in one portion. The reaction mixture was slowly warmed to 50°C and stirred for 16 hours. The reaction mixture was cooled to room temperature, quenched with methanol and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The layers were separated and the organic layer was concentrated under reduced pressure to give 9,9'-(3-(4,6-bis(9H-carbazole-9-yl-d8)-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-2,4-diyl-2',3',4',5',6'-d5)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8 compound H16 (0.70 g, 25% yield) as a white solid.

[0710]

[0711] Step 1: To a 2L round bottom flask equipped with a septum and a stirring bar, 2-bromo-1,3-difluoro-5-iodobenzene (82.00 g, 1 Eq, 257.1 mmol), phenylboronic acid (31.35 g, 1 Eq, 257.1 mmol), potassium carbonate (106.6 g, 45.17 mL, 3 Eq, 771.4 mmol), dioxane (600.0 mL) and water (120.0 mL) were added. The mixture was bubbled with N2 for 60 minutes. Tetrakis(triphenylphosphine)palladium(0) (6.537 g, 0.022 Eq, 5.657 mmol) was added. The headspace of the flask was purged with N2 for 10 minutes. A new N2 balloon was attached. The reaction mixture was stirred at 90°C for 18 hours. It was then cooled to room temperature and diluted with EtOAc (400 mL) and water (400 mL). The phases were separated and the aqueous phase was back extracted with DCM (500 mL). The combined organic phases were briefly dried with MgSO4 and filtered. The filtrate was concentrated to give a dark syrupy residue. Purification by silica gel column chromatography eluting with heptane gave 4-bromo-3,5-difluoro-1,1'-biphenyl 54 g (yield 78%) as a white solid.

[0712] Step 2: 4-bromo-3,5-difluoro-1,1'-biphenyl (44.00 g, 1 Eq, 163.5 mmol), 9H-carbazole (56.05 g, 2.05 Eq, 335.2 mmol), cesium carbonate (133.2 g, 32.71 mL, 2.5 Eq, 408.8 mmol) and DMF (500.00 mL) were added to a 1 L flask. The reaction mixture was stirred vigorously at 110 ° C for 72 hours. It was cooled to room temperature and then poured into water (about 2.5 L). The suspension was stirred briefly, filtered and dried in air. The white solid crude product was stirred in MeOH (1.5 L) for 3 hours, filtered and dried in air to obtain a white solid. It was then stirred vigorously in DCM (100 mL) / MeOH (1000 mL) for 3 hours, filtered and dried under vacuum. 47 g (yield 51%) of 9,9′-(4-bromo-[1,1′-biphenyl]-3,5-diyl)bis(9H-carbazole) was obtained as a white solid.

[0713] Step 3: 9,9'-(4-bromo-[1,1'-biphenyl]-3,5-diyl)bis(9H-carbazole) (23.00 g, 1 Eq, 40.82 mmol) was added to a 1 L round bottom flask and stirred briefly in anhydrous THF (270.00 mL) to give a clear solution. The solution was purged with nitrogen for 5 minutes. The reaction mixture was then cooled to 0°C (ice bath) and a hexane solution of n-butyllithium (3.318 g, 30.61 mL, 1.6 molar concentration, 1.2 Eq, 48.98 mmol) was added dropwise over 15 minutes. A dark brown solution was observed. It was stirred at 0 to 5°C for 30 minutes. At 0 ° C, a colorless clear solution of 2,4,6-trichloro-1,3,5-triazine (15.05 g, 2 Eq, 81.63 mmol) in anhydrous THF (90.00 mL) was added dropwise to the above reaction mixture over 5 minutes. A bright yellow solution was formed. The reaction mixture was stirred for another 5 minutes and the ice bath was removed. The reaction mixture was stirred at room temperature for 30 minutes, heated to 60 ° C, and stirred for 18 hours. The reaction mixture was cooled to room temperature, water (200 mL) and ethyl acetate (200 mL) were added, and the layers were separated. The aqueous layer was extracted with DCM (3×200 mL). The organics were combined, dehydrated and filtered over anhydrous MgSO4. The solvent was removed under vacuum on a rotary evaporator. The crude product was purified on silica gel using dichloromethane / heptane to afford 9,9',9"-(2-(4,6-dichloro-1,3,5-triazin-2-yl)benzene-1,3,5-triyl)tris(9H-carbazole) (11 g, 43% yield) as a bright yellow solid.

[0714] Step 4: Into a 250 mL round bottom flask were added 9,9',9"-(2-(4,6-dichloro-1,3,5-triazin-2-yl)benzene-1,3,5-triyl)tris(9H-carbazole) (5.300 g, 1 Eq, 7.344 mmol), 9H-carbazole (4.428 g, 2.5 Eq, 26.48 mmol), cesium carbonate (10.35 g, 3 Eq, 31.78 mmol) and NMP (120.000 mL). The reaction mixture was heated to 100 °C in an oil bath and stirred for 48 hours. The reaction mixture was cooled to room temperature, and water (600 mL) and DCM (400 mL) were added to the reaction mixture. Approximately 20 g of NaCl is to help layer separation. Separate each layer, and extract the aqueous layer with DCM (400mL). Combine organic matter, dehydrate and filter through anhydrous Na2SO4. At 50 ℃, under vacuum, remove solvent on rotary evaporator. Use dichloromethane and heptane to purify crude product on silica gel to obtain yellow solid (5.3g). Add the above crude product (5.3g) and DCM (100.00mL) in a 500ml flask and stir briefly to obtain a yellow clear solution. After the solution is cooled with an ice bath, acetyl chloride (7.446g, 6.744mL, 16Eq, 94.85mmol) and pyridine (11.25g, 11.5mL, 24Eq, 142 .3mmol). Stir for 18 hours. Add additional acetyl chloride (7.446g, 6.744mL, 16Eq, 94.85mmol) and pyridine (11.25g, 11.5mL, 24Eq, 142.3mmol). Heat to 30°C and stir for 18 hours. The reaction mixture is cooled to room temperature and water (50mL) is added. The layers are separated and the aqueous layer is extracted with DCM (50mL). The organics are combined, dehydrated over anhydrous Na2SO4 and filtered. The solvent is removed on a rotary evaporator at 50°C under vacuum. The crude product is purified on silica gel using dichloromethane and heptane to obtain a light yellow solid compound H17 (4.5g, 60%).

[0715] The HOMO and LUMO values ​​of compounds H1 to H17 were determined using solution electrochemistry. Solution cyclic voltammetry and differential pulse voltammetry were performed using a CH Instruments model 6201B potentiostat with anhydrous dimethylformamide solvent and tetrabutylammonium hexafluorophosphate as the loading electrolyte. Glassy carbon and platinum and silver wires were used as working, counter and reference electrodes, respectively. The electrochemical potential was measured by measuring the peak potential difference using differential pulse voltammetry with an internal ferrocene-ferrocene salt redox pair (Fc / Fc+) as the internal standard. 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 J.) J.), Journal of Advanced Materials (J. Adv. Mater. 1995, 7, 551), the corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were determined by comparing the cation and anion redox potentials with those of a ferrocene reference (4.8 eV relative to vacuum).

[0716] The triplet energies of compounds H1 to H17 were measured and are shown in Table 1. T1 was obtained from the maximum peak of gated emission of frozen samples in 2-MeTHF at 77K. Gated emission spectra were collected on a Horiba Fluorolog-3 spectrofluorometer equipped with a xenon flash lamp (flash delay of 10 milliseconds and collection window of 50 milliseconds). RTλmax was obtained from the maximum peak of fluorescence emission of degassed solution samples in 2-MeTHF at room temperature, measured on a Horiba Fluorolog-3 spectrofluorometer equipped with a Synapse Plus CCD detector. All samples were excited at 300nm.

[0717] Table 1: Electrochemical and photophysical properties

[0718]

[0719]

[0720] OLED devices were fabricated using the E host of the present invention and comparative compound C1 as electron transport hosts. The device results are shown in Table 1, where the voltage was measured at 10 mA / cm 2 Measured below.

[0721]

[0722]

[0723] OLEDs were grown on glass substrates pre-coated with a 15-Ω / sq indium tin oxide (ITO) layer. Prior to any organic layer deposition or coating, the substrates were degreased with solvents and then treated with oxygen plasma at 100 mTorr, 50 W for 1.5 min and UV ozone for 5 min. The glass substrates were pre-coated with a 15-Ω / sq indium tin oxide (ITO) layer. The substrates were degreased with solvents and then treated with oxygen plasma at 100 mTorr, 50 W for 1.5 min and UV ozone for 5 min. The substrates were pre-coated with a 15-Ω / sq indium tin oxide (ITO) layer ... -6 The device is manufactured by thermal evaporation in a tray. The anode electrode is Indium tin oxide (ITO). All devices were packaged with glass lids and sealed with epoxy resin in a nitrogen glove box (H2O and O2 <1 ppm) immediately after fabrication, with a desiccant incorporated inside the package. Doping percentages are by volume.

[0724] The device shown in Table 1 has organic layers consisting of the following in order starting from the ITO surface: Compound 1 (HIL), Compound 2 (HTL), Compound 3 (EBL), H host doped with 40% E host and 12% emitter 1 (EML), Compound 4 (BL), Compound 5 doped with 35% of compound 6 (ETL), Compound 5 (EIL), followed by Al (cathode), wherein the E host is one of compounds H1 to H17 shown in Table 2. The voltages of device examples 1 to 12 are reported relative to the value of comparative example 1.

[0725] Table 2: Device performance

[0726] E-body CIE λmax(nm) Rel.V Example 1 Compound H1 (0.136,0.152) 460 0.84 Example 2 Compound H2 (0.132,0.137) 460 0.94 Example 3 Compound H3 (0.133,0.143) 460 0.91 Example 4 Compound H5 (0.139,0.161) 460 1.00 Example 5 Compound H8 (0.141,0.169) 461 0.86 Example 6 Compound H9 (0.133,0.133) 460 0.94 Example 7 Compound H11 (0.134,0.139) 461 0.82 Example 8 Compound H12 (0.134,0.146) 460 0.80 Example 9 Compound H13 (0.143,0.170) 460 0.96 Example 10 Compound H15 (0.137,0.142) 460 0.96 Example 11 Compound H16 (0.133,0.127) 460 1.01 Example 12 Compound H17 (0.145,0.191) 461 0.99 Comparative Example 1 Comparative Compound C1 (0.135,0.144) 460 1.00

[0727] The above data show that each of device examples 1 to 12 (including one of the present compound H1 to compound H17) exhibits similar or reduced voltages compared to a comparative device using a related analog (comparative compound C1). The voltage reduction of up to 20% for examples 1 to 12 exceeds any value attributable to experimental error, and the observed improvements are significant. Based on the fact that the devices have the same device structure and the only difference is the choice of substitution in the triazine host, the significant improvement in performance observed from the above data is unexpected. Without being bound by any theory, this improvement may be attributed to better delocalization of the LUMO achieved by substitution of the phenyltriazine core, substitution of carbazole, or expansion of the LUMO density using an aromatic ring.

Claims

1. A compound comprising formula I in X 1 To X 3 are independently CR or N, and X 1 To X 3 At least one of them is N; X 4 To X 6 independently C or N; R A It is a single substitution to a maximum of substitutions allowed; each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Each R A R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, aryl substituted with CN, heteroaryl substituted with CN, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; 1 To R 4 are independently selected from the group consisting of aryl, heteroaryl, silane and germyl, wherein each R 1 To R 4 is optionally further substituted; Any R 3 , R 4 and R A may be joined or fused to form a ring, provided that R 3 and R 4 Neither R A Join to form a 5-membered ring; The condition is that if R 1 and R 2 are each aryl, then the compound comprises a silane group, a germane group or a borane group; and The condition is that if X 1 To X 3 Each is N, then X 4 To X 6 None of them is N; and The condition is that if R 1 To R 3 are each unsubstituted fully or partially deuterated or non-deuterated carbazole, then at least one R A Not H or R 4 Not triphenylsilane, carbazole dibenzothiophene, dibenzofuran, benzene or N-phenylcarbazole or their fully or partially deuterated analogs.

2. The compound of claim 1, wherein each R is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof; and / or where X 1 To X 3 At least two of them are N.

3. The compound according to claim 1, wherein R 1 and R 2 At least one of which is substituted or unsubstituted carbazole; and / or wherein R 3 and R 4 Each is selected from substituted or unsubstituted aryl or heteroaryl; and / or wherein R 3 and R 4 Each is selected from substituted or unsubstituted carbazole, substituted or unsubstituted benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bisbenzimidazolidinone), and aza variants thereof.

4. The compound according to claim 1, wherein the compound comprises at least one silane group; and / or the compound is fully or partially deuterated; and / or wherein the compound has a LUMO energy level of <-2.

65.

5. The compound of claim 1, wherein the compound does not comprise a moiety selected from the group consisting of Formula II, III, IV, V, VI and VII: wherein rings A, B and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; Wherein each X in Formula II, III, IV, V, VI and VII 7 To X 84 and X 201 To X 216 independently C or N; Where Z 1 To Z 4 and Y E are each independently a direct bond or selected from the group consisting of: O, S, Se, NR, BR, BRR', PR, CR, C=X, CRR', SO, SO2, SiRR', GeRR', P(O)R, aryl, heteroaryl, alkyl, heterocycloalkyl, and cycloalkyl; wherein X is selected from the group consisting of O, S and CRR'; Where W 1 and W 2 Each independently selected from the group consisting of: O, S, Se, CRR', SiRR' and GeRR'; Where Z A independently C, Si or Ge; Among them, each R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W and R X represents mono-substitution to the maximum amount of substitution, or no substitution; Among them, R, R', R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W and R X Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof.

6. The compound according to claim 1, wherein R 1 To R 4 Each of the above is selected from substituted or unsubstituted carbazole, substituted or unsubstituted bisbenzimidazolidazole, substituted or unsubstituted benzene ring, substituted or unsubstituted 6-membered heteroaromatic ring, substituted silyl or substituted germyl, unsubstituted carbazole, fully or partially deuterated carbazole, unsubstituted bisbenzimidazolidazole, fully or partially deuterated bisbenzimidazolidazole, fully or partially deuterated benzene ring, carbazole or bisbenzimidazolidazole substituted with a group selected from alkyl, silyl or nitrile, unsubstituted benzene ring, benzene ring substituted with alkyl, benzene ring fused with cycloalkyl, substituted with one or more non-fused aromatic or heteroaromatic rings. a benzene ring substituted with a silyl or germyl group, a benzene ring substituted with a silyl or germyl group, an unsubstituted 6-membered heteroaromatic ring, a completely or partially deuterated 6-membered heteroaromatic ring, an alkyl group substituted with a 6-membered heteroaromatic ring, a 6-membered heteroaromatic ring fused with a cycloalkyl group, a 6-membered heteroaromatic ring substituted with one or more non-fused aromatic or heteroaromatic rings, a 6-membered heteroaromatic ring substituted with a silyl or germyl group, a silyl or germyl group substituted with three aromatic or heteroaromatic rings, a silyl or germyl group substituted with two aromatic or heteroaromatic rings and an alkyl group, a silyl or germyl group substituted with one aromatic or heteroaromatic ring and two alkyl groups, or a silyl or germyl group substituted with three alkyl groups.

7. A compound comprising the structure of Formula I*: wherein the compound is partially or fully deuterated; Where X 1* , X 2* and X 3* Each is independently CR * or N; Where X 1* , X 2* and X 3* At least two of them are N; Where R * , R 1* , R 2* and R 3* are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Where R 1* , R 2* and R 3* At least one of them has a structure of Formula II*: Where Z 1* and Z 2* Each is a group having a molecular weight (MW) ≥ 77 g / mol; Wherein the dotted line ------- represents a direct bond, and the direct bond is connected to the X-containing 1* , X 2* and X 3* The ring carbon atoms contained in the ring of wherein [X] represents a monocyclic ring containing one 5- to 10-membered carbocyclic or heterocyclic ring, or a polycyclic fused ring system containing at least two fused 5- to 10-membered carbocyclic or heterocyclic rings, and may be further substituted; where Y 1* and Y 2* are all independently a single bond or a linking group; Where Z 1* and Z 2* Essentially reside in the formula I* containing X 1* , X 2* and X 3* The rings are above and below the plane of the ring.

8. The compound of claim 1, wherein the compound is selected from the group consisting of: in X 7 To X 46 each independently is C or N; R B To R G and R DD Each is a single substitution up to the maximum number of substitutions allowed; Each R B , R C , R D , R E , R F , R G , R 5 , R 6 and R 7 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and Each R DD is deuterated or a fully or partially deuterated substituent.

9. The compound of claim 1, wherein the compound is selected from the group consisting of compound W1-(Rm)(Rn)(Ro)(Rp), compound W2-(Rn)(Ro)(Rp)(Rq), compound W3-(Rn)(Ro)(Rp)(Zk), wherein W1 is an integer from 1 to 4 and from 33 to 38, wherein W2 is an integer from 5 to 23, wherein W3 is an integer from 24 to 32, m is an integer from 1 to 139, n, o, p, q are each an integer from 1 to 141, k is an integer from 1 to 84, each of Rm, Rn, Ro, Rp and Rq is independently selected from the group consisting of R1 to R141, wherein Zk is selected from the group consisting of Z1 to Z 84; wherein each of compounds 1-(R1)(R1)(R1)(R1) to compounds 4-(R139)(R141)(R141)(R141), compounds 5-(R1)(R1)(R1)(R1) to compounds 23-(R141)(R141)(R141)(R141), compounds 24-(R1)(R1)(R1)(Z1) to compounds 32-(R141)(R141)(R141)(Z84) and compounds 33-(R1)(R1)(R1)(R1) to compounds 38-(R139)(R141)(R141)(R141) are defined as follows: wherein Z1 to Z84 are defined in List A as defined herein; wherein R1 to R141 are defined in List B as defined herein.

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

11. An organic light emitting device (OLED), comprising: anode; cathode; and An organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising Formula I: in X 1 To X 3 are independently CR or N, and X 1 To X 3 At least one of them is N; X 4 To X 6 independently C or N; R A It is a single substitution to a maximum of substitutions allowed; each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Each R A R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, aryl substituted with CN, heteroaryl substituted with CN, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; 1 To R 4 are independently selected from the group consisting of aryl, heteroaryl, silane and germyl, wherein each R 1 To R 4 is optionally further substituted; Any R 3 , R 4 and R A may be joined or fused to form a ring, provided that R 3 and R 4 Neither R A Join to form a 5-membered ring; The condition is that if R 1 and R 2 are each aryl, then the compound comprises a silane group, a germane group or a borane group; and The condition is that if X 1 To X 3 Each is N, then X 4 To X 6 None of them is N; and The condition is that if R 1 To R 3 are each unsubstituted fully or partially deuterated or non-deuterated carbazole, then at least one R A Not H or R 4 Not triphenylsilane, carbazole dibenzothiophene, dibenzofuran, benzene or N-phenylcarbazole or their fully or partially deuterated analogs.

12. The OLED of claim 11, wherein the compound is a host and the organic layer is an emissive layer comprising a phosphorescent material, and wherein the phosphorescent material is a luminescent material having the formula M(L 1 ) x (L 2 ) y (L 3 ) z Metal coordination complexes; Where L 1 , L 2 and L 3 Can be the same or different; where x is 1, 2, or 3; Where y is 0, 1 or 2; where z is 0, 1 or 2; Wherein x+y+z is the oxidation state of the metal M; Where L 1 Select from the group consisting of structures in the ligand list: Where L 2 and L 3 Independently selected from the group consisting of: and structures in the ligand list; where: T is selected from the group consisting of B, Al, Ga and In; K 1 ' is a direct key or selected from NR e , PR e , O, S and Se; Each Y 1 To Y 13 independently selected from the group consisting of carbon and nitrogen; Y'Select from the group consisting of: BR e NR e , PR e ,O,S,Se,C=O,S=O,SO2,CR e R f 、SiR e R f and GeR e R f ; R e With R f may be fused or joined to form a ring; Each R a , R b , R c and R d can independently represent a single substitution to the maximum possible number of substitutions, or no substitution; each R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, selenanyl, and combinations thereof; and Where R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d Any two of may be fused or joined to form a ring or to form a multidentate ligand.

13. The OLED according to claim 12, wherein the phosphorescent material has a structure of Formula XI or Formula XII: in: X 105 To X 111 and Z 102 To Z 104 each independently is C or N; Where K 1 and K 2 Each independently selected from the group consisting of: direct key, O, S, N (R α )、P(R α )、B(R α )、C(R α )(R β ) and Si(R α )(R β ); L 1 and L 2 Each is independently selected from the group consisting of: direct bond, O, S, Se, NR', BR', BR'R", PR', CR', C=O, C=NR', C=CR'R", C=S, CR'R", SO, SO2, P(O)R', SiR'R" and GeR'R"; Each R AA '、R BB '、R CC '、R DD '、R EE '、R EE0 , R EE1 and R EE2 , R', R", R α and R β are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, germanyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; R EE ' indicates single substitution to the maximum number of substitutions allowed, or no substitution; and wherein any two substituents may be joined or fused to form a ring; or Wherein the phosphorescent material has a structure of Formula XIV or XV: in X 112 To X 119 are independently C or N; R EE3 are independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and any two substituents may be joined or fused to form a ring.

14. The OLED of claim 11, wherein the compound is a host and the OLED comprises an acceptor as an emitter and a sensitizer selected from the group consisting of a delayed fluorescent material, a phosphorescent material, and a combination thereof; wherein the sensitizer transfers energy to the acceptor.

15. A consumer product comprising an organic light emitting device (OLED), the organic light emitting device comprising: anode; cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to claim 1.

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