Patent Application
20250115631
The present disclosure generally relates to organic or metal coordination compounds and formulations and their various uses including as emitters, sensitizers, charge transporters, or exciton transporters in devices such as organic light emitting diodes and related electronic devices and consumer products.
Opto-electronic devices that make use of organic materials are becoming increasingly desirable for various reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials.
OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting.
One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively, the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single emissive layer (EML) device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.
In one aspect, the present disclosure provides a compound comprising a structure of Formula I,
In another aspect, the present disclosure provides a formulation comprising a compound comprising a structure of Formula I described herein.
In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound comprising a structure of Formula I described herein.
In yet another aspect, the present disclosure provides a consumer product comprising an OLED with an organic layer comprising a compound comprising a structure of Formula I described herein.
Unless otherwise specified, the below terms used herein are defined as follows:
As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
As used herein, “solution processable” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
As used herein, and as would 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 ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum 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 such a diagram than a “lower” HOMO or LUMO energy level.
As used herein, and as would be generally understood by one skilled in the art, a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to 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 further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
Layers, materials, regions, and devices may be described herein in reference to the color of light they emit. In general, as used herein, an emissive region that is described as producing a specific color of light may include one or more emissive layers disposed over each other in a stack.
As used herein, a “NIR”, “red”, “green”, “blue”, “yellow” layer, material, region, or device refers to a layer, a material, a region, or a device that emits light in the wavelength range of about 700-1500 nm, 580-700 nm, 500-600 nm, 400-500 nm, 540-600 nm, respectively, or a layer, a material, a region, or a device that has a highest peak in its emission spectrum in the respective wavelength region. In some arrangements, separate regions, layers, materials, or devices may provide separate “deep blue” and “light blue” emissions. As used herein, the “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 the “light blue” emission component. Typically, a “light blue” emission component has a peak emission wavelength in the range of about 465-500 nm, and a “deep blue” emission component has a peak emission wavelength in the range of about 400-470 nm, though these ranges may vary for some configurations.
In some arrangements, a color altering layer that converts, modifies, or shifts the color of the light emitted by another layer to an emission having a different wavelength is provided. Such a color altering layer can be formulated to shift wavelength of the light emitted by the other layer by a defined amount, as measured by the difference in the wavelength of the emitted light and the wavelength of the resulting light. In general, there are two classes of color altering layers: color filters that modify a spectrum by removing light of unwanted wavelengths, and color changing layers that convert photons of higher energy to lower energy. For example, a “red” color filter can be present in order to filter an input light to remove light having a wavelength outside the range of about 580-700 nm. A component “of a color” refers to a component that, when activated or used, produces or otherwise emits light having a particular color as previously described. For example, a “first emissive region of a first color” and a “second emissive region of a second color different than the first color” describes two emissive regions that, when activated within a device, emit two different colors as previously described.
As used herein, emissive materials, layers, and regions may be distinguished from one another and from other structures based upon light initially generated by the material, layer or region, as opposed to light eventually emitted by the same or a different structure. The initial light generation typically is the result of an energy level change resulting in emission of a photon. For example, an organic emissive material may initially generate blue light, which may be converted by a color filter, quantum dot or other structure to red or green light, such that a complete emissive stack or sub-pixel emits the red or green light. In this case the initial emissive material, region, or layer may be referred to as a “blue” component, even though the sub-pixel is a “red” or “green” component.
In some cases, it may be preferable to describe the color of a component such as an emissive region, sub-pixel, color altering layer, or the like, in terms of 1931 CIE coordinates. For example, a yellow emissive material may have multiple peak emission wavelengths, one in or near an edge of the “green” region, and one within or near an edge of the “red” region as previously described. Accordingly, as used herein, each color term also corresponds to a shape in the 1931 CIE coordinate color space. The shape in 1931 CIE color space is constructed by following the locus between two color points and any additional interior points. For example, interior shape parameters for red, green, blue, and yellow may be defined as shown below:
In some cases The terms “halo,” “halogen,” and “halide” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.
The term “acyl” refers to a substituted carbonyl group (—C(O)—Rs).
The term “ester” refers to a substituted oxycarbonyl (—O—C(O)—Rs or —C(O)—O—Rs) group.
The term “ether” refers to an —ORs group.
The terms “sulfanyl” or “thio-ether” are used interchangeably and refer to a —SRs group.
The term “selenyl” refers to a —SeRs group.
The term “sulfinyl” refers to a —S(O)—Rs group.
The term “sulfonyl” refers to a —SO2—Rs group.
The term “phosphino” refers to a group containing at least one phosphorus atom bonded to the relevant structure. Common examples of phosphino groups include, but are not limited to, groups such as a —P(Rs)2 group or a —PO(Rs)2 group, wherein each Rs can be same or different.
The term “silyl” refers to a group containing at least one silicon atom bonded to the relevant structure. Common examples of silyl groups include, but are not limited to, groups such as a —Si(Rs)3 group, wherein each Rs can be same or different.
The term “germyl” refers to a group containing at least one germanium atom bonded to the relevant structure. Common examples of germyl groups include, but are not limited to, groups such as a —Ge(Rs)3 group, wherein each Rs can be same or different.
The term “boryl” refers to a group containing at least one boron atom bonded to the relevant structure. Common examples of boryl groups include, but are not limited to, groups such as a —B(Rs)2 group or its Lewis adduct —B(Rs)3 group, wherein Rs can be same or different.
In each of the above, Rs can be hydrogen or a substituent selected from the group consisting of the general substituents as defined in this application. Preferred Rs is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combination thereof. More preferably Rs is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.
The term “alkyl” refers to and includes both straight and branched chain alkyl groups having an alkyl carbon atom bonded to the relevant structure. Preferred alkyl groups are those containing from one to fifteen carbon atoms, preferably one to nine carbon atoms, and includes 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. Additionally, the alkyl group can be further substituted.
The term “cycloalkyl” refers to and includes monocyclic, polycyclic, and spiro alkyl groups having a ring alkyl carbon atom bonded to the relevant structure. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl group can be further substituted.
The terms “heteroalkyl” or “heterocycloalkyl” refer to an alkyl or a 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. Additionally, the heteroalkyl or heterocycloalkyl group can be further substituted.
The term “alkenyl” refers to and includes both straight and branched chain alkene groups. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain with one carbon atom from the carbon-carbon double bond that is bonded to the relevant structure. Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. The term “heteroalkenyl” as used herein refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably, O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl group can be further substituted.
The term “alkynyl” refers to and includes both straight and branched chain alkyne groups. Alkynyl groups are essentially alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain with one carbon atom from the carbon-carbon triple bond that is bonded to the relevant structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group can be further substituted.
The terms “aralkyl” or “arylalkyl” are used interchangeably and refer to an aryl-substituted alkyl group having an alkyl carbon atom bonded to the relevant structure. Additionally, the aralkyl group can be further substituted.
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. Hetero-aromatic cyclic groups may be used interchangeably with heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 10 ring atoms, preferably those containing 3 to 7 ring atoms, which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers/thio-ethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Additionally, the heterocyclic group can be further substituted or fused.
The term “aryl” refers to and includes both single-ring and polycyclic aromatic hydrocarbyl groups. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining 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. Especially preferred is an aryl group having six carbons, ten carbons, twelve carbons, fourteen carbons, or eighteen carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, and naphthalene. Additionally, the aryl group can be further substituted or fused, such as, without limitation, fluorene.
The term “heteroaryl” refers to and includes both single-ring aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. The heteroatoms include, but are not limited to O, S, Se, N, P, B, Si, Ge, and Se. In many instances, O, S, N, or B are the preferred heteroatoms. Hetero-single ring aromatic systems are preferably single rings with 5 or 6 ring atoms, and the ring can have from one to six heteroatoms. The hetero-polycyclic ring systems can have two or more aromatic rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl. The hetero-polycyclic aromatic ring systems can have from one to six heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenophenodipyridine, azaborine, borazine, 5λ2,9λ2-diaza-13b-boranaphtho[2,3,4-de]anthracene, 5,λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 5,λ2,9λ2-diaza-13b-boranaphtho[2,3,4-de]anthracene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene. Additionally, the heteroaryl group can be further substituted or fused.
Of the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 5λ2,9λ2-diaza-13b-boranaphtho[2,3,4-de]anthracene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and the respective aza-analogs of each thereof are of particular interest.
In many instances, the General Substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In some instances, the Preferred General Substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
In some instances, the More Preferred General Substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, aryl, heteroaryl, nitrile, sulfanyl, and combinations thereof.
In some instances, the Even More Preferred General Substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof.
In yet other instances, the Most Preferred General Substituents are selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
The terms “substituted” and “substitution” refer to a substituent other than H that is bonded to the relevant position, e.g., a carbon or nitrogen. For example, when R1 represents mono-substitution, then one R1 must be other than H (i.e., a substitution). Similarly, when R1 represents di-substitution, then two of R1 must be other than H. Similarly, when R1 represents zero or no substitution, R1, for example, can be a hydrogen for all available valencies of ring atoms, as in carbon atoms for benzene and the nitrogen atom in pyrrole, or simply represents nothing for ring atoms with fully filled valencies, e.g., the nitrogen atom in pyridine. The maximum number of substitutions possible in a ring structure will depend on the total number of available valencies in the ring atoms.
As used herein, “combinations thereof” indicates that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, an alkyl and deuterium can be combined to form a partial or fully deuterated alkyl group; a halogen and alkyl can be combined to form a halogenated alkyl substituent; and a halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. In one instance, the term substitution includes a combination of two to four of the listed groups. In another instance, the term substitution includes a combination of two to three groups. In yet another instance, the term substitution includes a combination of two groups. Preferred combinations of substituent groups are those that contain up to fifty atoms that are not hydrogen or deuterium, or those which include up to forty atoms that are not hydrogen or deuterium, or those that include up to thirty atoms that are not hydrogen or deuterium. In many instances, a preferred combination of substituent groups will include up to twenty atoms that are not hydrogen or deuterium.
The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective aromatic ring can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.
As used herein, “deuterium” refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, Patent Pub. No. WO 2006/095951, and U.S. Pat. Application Pub. No. US 2011/0037057, which are hereby incorporated by reference in their entireties, describe the making 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. (Reviews) 2007, 46, 7744-65, which are incorporated by reference in their entireties, describe the deuteration of the methylene hydrogens in benzyl amines and efficient pathways to replace aromatic ring hydrogens with deuterium, respectively.
As used herein, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. includes undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also include undeuterated, partially deuterated, and fully deuterated versions thereof. Unless otherwise specified, atoms in chemical structures without valences fully filled by H or D should be considered to include undeuterated, partially deuterated, and fully deuterated versions thereof. For example, the chemical structure of
implies to include C6H6, C6D6, C6H3D3, and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, without limitation, CD3, CD2C(CH3)3, C(CD3)3, and C6D5.
It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.
In some instances, a pair of substituents in the molecule can be optionally joined or fused into a ring. The preferred ring is a five to nine-membered carbocyclic or heterocyclic ring, includes both instances where the portion of the ring formed by the pair of substituents is saturated and where the portion of the ring formed by the pair of substituents is unsaturated. In yet other instances, a pair of adjacent substituents can be optionally joined or fused into a ring. As used herein, “adjacent” means that the two substituents involved can be on the same ring next to each other, or on two neighboring rings having the two closest available substitutable positions, such as 2, 2′ positions in a biphenyl, or 1, 8 position in a naphthalene.
The organometallic complexes described herein include a substituent at the 7-position of the benzimidazole moiety and exhibit higher PLQY values than equivalent compounds without a substituent at the 7-position of the benzimidazole moiety.
In one aspect, the present disclosure provides a compound comprising a structure of Formula I,
In some embodiments, if Y1 is O, S, or Se, then either A2, R4, and L3 are absent or A1, R3, and L2 are absent. In some embodiments, Y1 is O, S, or Se, and A2, R4, and L3 are absent. In some embodiments, Y1 is O, S, or Se, and A1, R3, and L2 are absent.
In some embodiments, the compound consists essentially Formula I. In some embodiments, the compound has a structure of Formula I.
In some embodiments, R1 and R2 are not joined or fused to form a ring.
In some embodiments, R1 is not joined or fused to X3 to form a 5-membered ring.
In some embodiments, R2 is not joined or fused to X6 to form a 5-membered ring.
In some embodiments, R is not joined or fused to X1 to form a 6-membered ring.
In some embodiments, if R2 is H, R1 is not selected from the group consisting of
except that R1 can be substituted or unsubstituted carbazole;
In some embodiments, the compound is not
In some embodiments, each R, R′, R*, R1, R2, R3, R4, RA, RB, RC, Rα, and Rβ is independently a hydrogen or a substituent selected from the group consisting of the Preferred General Substituents defined herein. In some embodiments, each R, R′, R*, R1, R2, R3, R4, RA, RB, RC, Rα, and RB is independently a hydrogen or a substituent selected from the group consisting of the More Preferred General Substituents defined herein. In some embodiments, each R, R′, R*, R1, R2, R3, R4, RA, RB, RC, Rα, and Rβ is independently a hydrogen or a substituent selected from the group consisting of the Most Preferred General Substituents defined herein.
In some embodiments of Formula I, at least one of R*, R1, R2, R3, R4, RA, RB, or RC is partially or fully deuterated. In some embodiments, R* is partially or fully deuterated. In some embodiments, R1 is partially or fully deuterated. In some embodiments, R2 is partially or fully deuterated. In some embodiments, R3 is partially or fully deuterated. In some embodiments, R4 is partially or fully deuterated. In some embodiments, at least one RA is partially or fully deuterated. In some embodiments, at least one RB is partially or fully deuterated. In some embodiments, at least one RC is partially or fully deuterated. In some embodiments, at least one Rα or Rβ is partially or fully deuterated.
In some embodiments, moiety C is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole derived carbene, aza-benzimidazole derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanathrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, the aza variant includes one N on a benzo ring. In some embodiments, the aza variant includes one N on a benzo ring and the N is bonded to the metal M.
In some embodiments, moiety C is a monocyclic ring. In some embodiments, moiety C is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole. In some embodiments, moiety C is benzene.
In some embodiments, moiety C is a polycyclic fused ring system. In some embodiments, moiety C is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole derived carbene, aza-benzimidazole derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanathrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.
In some embodiments, moiety C is carbazole or aza-carbazole. In some embodiments, moiety C is carbazole. In some embodiments, moiety C is aza-carbazole. In some such embodiments, Z2, X8, and X9 are all C. In some such embodiments, the N of the pyrrole ring forms a direct bond to A1.
In some embodiments, the compound has a structure of Formula II,
wherein:
In embodiments of Formula II, Y1 can be selected from the group consisting of C, N, P, and As. In some embodiments, Y1 is N.
In some embodiments, moiety D is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole derived carbene, aza-benzimidazole derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanathrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene. In some embodiments, the aza variant includes one N on a benzo ring. In some embodiments, the aza variant includes one N on a benzo ring and the N is bonded to the metal M.
In some embodiments, moiety D is a monocyclic ring. In some embodiments, moiety D is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole. In some embodiments, moiety D is pyridine. In some such embodiments, Y1 is N.
In some embodiments, moiety D is a polycyclic fused ring system. In some embodiments, moiety D is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, benzimidazole derived carbene, aza-benzimidazole derived carbene, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanathrene, anthracene, aza-anthracene, phenanthridine, fluorene, and aza-fluorene.
In some embodiments, moiety D is quinoline or isoquinoline. In some such embodiments, Y1 is N.
In some embodiments, each of moiety C and moiety D can independently be a polycyclic fused ring structure. In some embodiments, each of moiety C and moiety D can independently be a polycyclic fused ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused ring structure has two 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, each of moiety C and moiety D can independently be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and aza-variants thereof. In some such embodiments, each of moiety C and moiety D can independently be further substituted at the ortho- or meta-position of the O, S, or Se atom by a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza-variants contain exactly one N atom at the 6-position (ortho to the O, S, or Se) with a substituent at the 7-position (meta to the O, S, or Se).
In some embodiments, each of moiety C and moiety D can independently be a polycyclic fused ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused ring structure comprises three 6-membered rings and one 5-membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted by a substituent selected from the group consisting of deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, each of moiety C and moiety D can independently be a polycyclic fused ring structure comprising at least five fused rings. In some embodiments, the polycyclic fused ring structure comprises four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments with one 5-membered ring, the 5-membered ring is fused to the ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, the third 6-membered ring is fused to the second 6-membered ring, and the fourth 6-membered ring is fused to the third 6-membered ring.
In some embodiments, each of moiety C and moiety D can independently be an aza version of the polycyclic fused rings described above. In some such embodiments, each of moiety C and moiety D can independently contain exactly one aza N atom. In some such embodiments, each of moiety C and moiety D contains exactly two aza N atoms, which can be in one ring, or in two different rings. In some such embodiments, the ring having aza N atom is separated by at least two other rings from the metal M atom. In some such embodiments, the ring having aza N atom is separated by at least three other rings from the metal M atom. In some such embodiments, each of the ortho positions of the aza N atom is substituted.
In some embodiments, two of Z1, Z2, and Y1 are C, and the remaining one is N or carbene C. In some such embodiments, the remaining one is N.
In some embodiments, Z1 and Z2 are C, and Y1 is N or carbene C. In some such embodiments, Y1 is N.
In some embodiments, each of X1 to X9 is C.
In some embodiments, X4 and X5 are C.
In some embodiments, at least one of X4 or X5 is N. In some embodiments, exactly one of X4 or X5 is N. In some embodiments, X4 is N. In some embodiments, X5 is N.
In some embodiments, each of X1 to X4 is C.
In some embodiments, at least one of X1 to X4 is N. In some embodiments, exactly one of X1 to X4 is N. In some embodiments, at least one of X1 to X3 is N, and X4 is C.
In some embodiments, each of X5 to X7 is C.
In some embodiments, at least one of X5 to X7 is N. In some embodiments, exactly one of X5 to X7 is N. In some embodiments, at least one of X6 or X7 is N, and X5 is C.
In some embodiments, each of X8 and X9 is C.
In some embodiments, at least one of X8 or X9 is N. In some embodiments, exactly one of X8 or X9 is N. In some embodiments, X8 is N. In some embodiments, X9 is N.
In some embodiments, Y1 is C. In some embodiments, Y1 is N. In some embodiments, Y1 is P. In some embodiments, Y1 is As.
In some embodiments, Y1 is selected from the group consisting of O, S, and Se. In some such embodiments, A2, R4, and L3 are absent, while A1, R3, and L2 are absent in other embodiments. In some embodiments, Y1 is O. In some embodiments, Y1 is S. In some embodiments, Y1 is Se.
In some embodiments, one of the bonds is a single bond and other
bond is a double bond.
In some embodiments, K is a direct bond.
In some embodiments, K is O or S. In some embodiments, K is S. In some embodiments, K is S.
In some embodiments, K is N(Rα), P(Rα), or B(Rα).
In some embodiments, K is C(Rα)(Rβ) or Si(Rα)(Rβ).
In some embodiments, A1 and A2 are both C. In some embodiments, one of A1 or A2 is C, and the other one is selected from the group consisting of Si, B, Ge, S, N, P, and As. In some embodiments, neither A1 nor A2 is C. In some embodiments, at least one of A1 or A2 is N. In some embodiments, at least one of A1 or A2 is B, Ge, S, Si, P, or As. In some embodiments, A1 is C, Si, N, P, or As. In some embodiments, A2 is C, Si, N, P, or As. In some embodiments, each of A1 and A2 is independently C, Si, N, P, or As.
In some embodiments, A1 is absent.
In some embodiments, one of L1, L2, or L3 is not present. In some embodiments, L3 is not present. In some embodiments, L2 is not present. In some embodiments, L1 is not present.
In some embodiments, L1 is a direct bond.
In some embodiments, L1 is selected from the group consisting of O, S, and Se. In some embodiments, L1 is O.
In some embodiments, L1 is selected from the group consisting of BR, NR, and PR. In some such embodiments, the R is aryl or heteroaryl. In some such embodiments, the R is bonded or fused to RB or RC.
In some embodiments, L1 is selected from the group consisting of P(O)R, C═O, C=S, C=Se, C=NR′, C=CRR′, S═O, and SO2. In some embodiments, L1 is selected from the group consisting of BRR′, CRR′, SiRR′, and GeRR′. In some embodiments, L1 is CR.
In some embodiments, L2 is a direct bond.
In some embodiments, L2 is selected from the group consisting of O, S, and Se.
In some embodiments, L2 is selected from the group consisting of BR, NR, and PR. In some embodiments, L2 is NR.
In some embodiments, the R of L2 is aryl and is joined or fused to an RC; wherein a combination of moiety C and L2 forms a carbazole or aza-carbazole moiety. In some such embodiments, Z2 is C.
In some embodiments, L2 is selected from the group consisting of P(O)R, C═O, C=S, C=Se, C=NR′, C=CRR′, S=O, and SO2. In some embodiments, L2 is selected from the group consisting of BRR′, CRR′, SiRR′, and GeRR′. In some embodiments, L2 is CR.
In some embodiments, L3 is a direct bond.
In some embodiments, L3 is selected from the group consisting of O, S, and Se.
In some embodiments, L3 is selected from the group consisting of BR, NR, and PR. In some embodiments, L3 is selected from the group consisting of P(O)R, C═O, C=S, C=Se, C=NR′, C=CRR′, S=O, and SO2. In some embodiments, L3 is selected from the group consisting of BRR′, CRR′, SiRR′, and GeRR′. In some embodiments, L3 is CR.
In some embodiments, each of L1, L2, and L3 is present.
In some embodiments, L1 is O, L2 is NR, and L3 is absent. In some such embodiments, moiety C and L2 forms a carbazole or aza-carbazole. As an alternate definition, L2 is a direct bond and moiety C is carbazole or aza-carbazole and the N forms a direct bond with A1.
In some embodiments, Formula I comprises an electron-withdrawing group. In some embodiments, the electron-withdrawing group has a Hammett constant larger than 0. In some embodiments, the electron-withdrawing group has a Hammett constant equal or larger than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.
In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of the structures of the following EWG1 LIST: F, CF3, CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SFs, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, +N(Rk2)3, (Rk2)2CCN, (Rk2)2CCF3, CNC(CF3)2, BRk3Rk2, substituted or unsubstituted dibenzoborole, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridoxine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated alkyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing alkyl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,
In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of
In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of the structures of the following EWG3 LIST:
In some embodiments, Formula I comprises an electron-withdrawing group selected from the group consisting of the structures of the following EWG4 LIST:
In some embodiments, Formula I comprises an electron-withdrawing group that is a π-electron deficient electron-withdrawing group. In some embodiments, the π-electron deficient electron-withdrawing group is selected from the group consisting of the structures of the following Pi-EWG LIST: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SFs, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC, +N(Rk2)3, BRk2Rk3, substituted or unsubstituted dibenzoborole, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,
wherein the variables are the same as previously defined.
In some embodiments of Formula I, at least one RA is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RA is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RA is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RA is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RA is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, at least one RB is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RB is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RB is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RB is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RB is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, at least one RC is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RC is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RC is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RC is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RC is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, R1 is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, R1 is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, R1 is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, R1 is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, R1 is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, R2 is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, R2 is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, R2 is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, R2 is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, R2 is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, R3 is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, R3 is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, R3 is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, R3 is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, R3 is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, R4 is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, R4 is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, R4 is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, R4 is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, R4 is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula I, R* is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, R* is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, R* is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, R* is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, R* is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments, R1 is not H, GeMe3, or GePh3. In some embodiments, R1 comprises at least one C atom. In some embodiments, R1 comprises at least two C atoms. In some embodiments, R1 comprises at least three C atoms. In some embodiments, R1 comprises at least four C atoms. In some embodiments, R1 comprises at least six C atoms. In some embodiments, R1 comprises at least twelve C atoms.
In some embodiments, R1 comprises a moiety selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some embodiments, R1 comprises aryl or heteroaryl. In some embodiments, R1 comprises (i) an aryl or heteroaryl moiety comprising at least 12 ring atoms, or (ii) at least two aromatic moieties that are not fused together.
In some embodiments, R1 is H or is absent.
In some embodiments, R2 is not H, GeMe3, or GePh3.
In some embodiments, R2 comprises at least one C atom. In some embodiments, R2 comprises at least two C atoms. In some embodiments, R2 comprises at least three C atoms. In some embodiments, R2 comprises at least four C atoms. In some embodiments, R2 comprises at least six C atoms. In some embodiments, R2 comprises at least twelve C atoms.
In some embodiments, R2 comprises a moiety selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some embodiments, R2 comprises aryl or heteroaryl. In some embodiments, R2 comprises (i) an aryl or heteroaryl moiety comprising at least 12 ring atoms, or (ii) at least two aromatic moieties that are not fused together.
In some embodiments, R2 is H or is absent.
In some embodiments, L3 is not present, and R* comprises a moiety selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, L3 is not present, and R* comprises aryl or heteroaryl.
In some embodiments, L3 is not present, and R* comprises (i) an aryl or heteroaryl moiety comprising at least 12 ring atoms, or (ii) at least two aromatic moieties that are not fused together. In some such embodiments, L3 comprises at least three aromatic moieties that are not fused together.
In some embodiments, at least one RA is not hydrogen. In some embodiments, at least one RA comprises at least one C atom. In some embodiments, at least one RA comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, at least one RB is not hydrogen. In some embodiments, at least one RB comprises at least one C atom. In some embodiments, at least one RB comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, at least one RC is not hydrogen. In some embodiments, at least one RC comprises at least one C atom. In some embodiments, at least one RC comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, R3 is not hydrogen. In some embodiments, R3 comprises at least one C atom.
In some embodiments, R4 is not hydrogen. In some embodiments, R4 comprises at least one C atom.
In some embodiments, the compound has a structure of Formula II,
wherein:
In some embodiments, at least one RD is not hydrogen. In some embodiments, at least one RD comprises at least one C atom. In some embodiments, at least one RD comprises a substituent selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, the compound has a structure of Formula IIA:
wherein:
In some embodiments, no RE is joined or fused with REE1 or REE2 to form a ring.
In some embodiments, REE0 is selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof.
In some embodiments, REE1 is the same as REE2. In some embodiments, REE1 is different from REE2.
In some embodiments, at least one of REE1 or REE2 comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other. In some embodiments, at least one of REE1 or REE2 comprises a chemical group containing at least four 6-membered aromatic rings that are not fused next to each other. In some embodiments, at least one of REE1 or REE2 comprises a chemical group containing at least five 6-membered aromatic rings that are not fused next to each other. In some embodiments, at least one of REE1 or REE2 comprises a chemical group containing at least six 6-membered aromatic rings that are not fused next to each other. In some embodiments, each of REE1 and REE2 independently comprises a chemical group containing at least three to six 6-membered aromatic rings that are not fused next to each other.
In some embodiments, at least one of REE1 or REE2 comprises a group RW, where RW has a structure selected from the group consisting of: Formula IIIA, ---QA(R1a)(R2a)a(R3a)b, Formula IIIB,
wherein:
In some embodiments, at least one YS, YT, or YU is SiRR′ or GeRR′. In some embodiments, each YS, YT, and YU is CRR′.
In some embodiments, at least one of REE1 and REE2 comprises a group RW. In some embodiments, each of REE1 and REE2 comprises a group RW. In some embodiments, each of REE1 and REE2 comprises Formula IIIA. In some embodiments, each of REE1 and REE2 comprises Formula IIIB. In some embodiments, each of REE1 and REE2 comprises Formula IIIC. In some embodiments, either REE1 or REE2 comprises Formula IIIA, and the other one of REE1 and REE2 comprises Formula IIIB. In some embodiments, either REE1 or REE2 comprises Formula IIIA, and the other one of REE1 and REE2 comprises Formula IIIC. In some embodiments, either REE1 or REE2 comprises Formula IIIB, and the other one of REE1 and REE2 comprises Formula IIIC.
In some embodiments, REE1 has a molecular weight (MW) greater than 15 g/mol and REE2 has a molecular weight greater than that of REE1. In some embodiments, REE1 has a molecular weight (MW) greater than 56 g/mol and REE2 has a molecular weight greater than that of REE1. In some embodiments, REE1 has a molecular weight (MW) greater than 76 g/mol and REE2 has a molecular weight greater than that of REE1. In some embodiments, REE1 has a molecular weight (MW) greater than 81 g/mol and REE2 has a molecular weight greater than that of REE1. In some embodiments, REE1 or REE2 has a molecular weight (MW) greater than 165 g/mol. In some embodiments, REE1 or REE2 has a molecular weight (MW) greater than 166 g/mol. In some embodiments, REE1 or REE2 has a molecular weight (MW) greater than 182 g/mol.
In some embodiments, REE1 has one more 6-membered aromatic ring than REE2. In some embodiments, REE1 has two more 6-membered aromatic ring than REE2. In some embodiments, REE1 has three more 6-membered aromatic ring than REE2. In some embodiments, REE1 has four more 6-membered aromatic ring than REE2. In some embodiments, REE1 has five more 6-membered aromatic ring than REE2
In some embodiments, REE1 comprises at least one heteroatom and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises at least two heteroatoms and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises at least three heteroatoms and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises exactly one heteroatom and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises exactly two heteroatoms and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises exactly three heteroatoms and REE2 consists of hydrocarbon and deuterated variant thereof. In some embodiments, REE1 comprises exactly one heteroatom and REE2 comprises exactly one heteroatom that is different from the heteroatom in REE1. In some embodiments, REE1 comprises exactly one heteroatom and REE2 comprises exactly one heteroatom that is same as the heteroatom in REE1.
In some embodiments, REE1 comprises exactly two heteroatoms and REE2 comprises exactly one heteroatom. In some embodiments, REE1 comprises exactly two heteroatoms and REE2 comprises exactly two heteroatoms. In some embodiments, REE1 comprises exactly three heteroatoms and REE2 comprises exactly one heteroatom. In some embodiments, REE1 comprises exactly three heteroatoms and REE2 comprises exactly two heteroatoms. In some embodiments, REE1 comprises exactly three heteroatoms and REE2 comprises exactly three heteroatoms.
In some embodiments, at least one of REE1 and REE2 comprises an aromatic ring fused to a non-aromatic ring. In some embodiments, both REE1 and REE2 comprise an aromatic ring fused to a non-aromatic ring. In some embodiments, the aromatic ring is a phenyl ring and the non-aromatic ring is a cycloalkyl ring.
In some embodiments, at least one of REE1 and REE2 is partially or fully deuterated. In some embodiments, both REE1 and REE2 are partially or fully deuterated.
In some embodiments of Formula IIIB, at least one RSS is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RSS is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RSS is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RSS is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RSS is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula IIIB, at least one RTT is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RTT is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RTT is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RTT is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RTT is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula IIIC, at least one RUU is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one RUU is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one RUU is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one RUU is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one RUU is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments of Formula IIIA, at least one of R1a, R2a, or R3a is or comprises an electron-withdrawing group from the EWG1 LIST as defined herein. In some embodiments, at least one of R1a, R2a, or R3a is or comprises an electron-withdrawing group from the EWG2 LIST as defined herein. In some embodiments, at least one of R1a, R2a, or R3a is or comprises an electron-withdrawing group from the EWG3 LIST as defined herein. In some embodiments, at least one of R1a, R2a, or R3a is or comprises an electron-withdrawing group from the EWG4 LIST as defined herein. In some embodiments, at least one of R1a, R2a, or R3a is or comprises an electron-withdrawing group from the Pi-EWG LIST as defined herein.
In some embodiments, at least one RD is partially or fully deuterated.
In some embodiments, the compound has a structure of Formula X:
wherein
In some embodiments, X1′ to X11′ are each C. In some embodiments, one of X1′ to X11′ is N. In some embodiments, two of X1′ to X11′ are N. In some embodiments, one of X1′ to X4′ is N. In some embodiments, one of X5′ to X8 is N. In some embodiments, X10′ is N.
In some embodiments, the compound is selected from the group consisting of compounds having the formula of Pt(LA′)(Ly):
In some embodiments, each R, R′, RA′, RB′, RC, RD, RX, and RY is independently selected from the group consisting of the structures of the following LIST 3:
In some embodiments, wherein at least one of R, R′, RA′, RB′, RC, RD, RX, and RY is independently selected from the group consisting of the structures of the following LIST 4:
In some embodiments, the compound is selected from the group consisting of the compounds having the formula of Pt(LA′)(Ly):
wherein LA′ is selected from the group consisting of LA′i′-(Ri)(Rj)(Rk)(Rl), wherein i′ is an integer from 1 to 20, and Ri is selected from the group consisting of R4 to R442 and each of Rj, Rk, and Rl is independently selected from the group consisting of R1 to R442, wherein each of LA′1-(R4)(R1)(R1)(R1) to LA′10-(R442)(R442)(R442)(R442) is defined in the following LIST 5:
wherein Ly is selected from the group consisting of Lyj′-(Rs)(Rt)(Ru), wherein j′ is an integer from 1 to 33, and each of Rs, Rt, and Ru is independently selected from the group consisting of R1 to R442, wherein each of Ly1-(R1)(R1)(R1) to Ly33—(R442)(R442)(R442), is defined in the following LIST 6:
This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 63/586,046, filed on Sep. 28, 2023, the entire contents of which are incorporated herein by reference
| Number | Date | Country | |
|---|---|---|---|
| 63586046 | Sep 2023 | US |
