Patent Application
20240294562
The present disclosure generally relates to organometallic compounds and formulations and their various uses including as emitters in devices such as organic light emitting diodes and related electronic devices.
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 having a formula of Ir(LA)n(LB)m(LC)o, where LA has a structure of Formula IA,
LB has a structure of Formula IB,
and LC is a bidentate ligand. In formula Ir(LA)n(LB)m(LC)o, Formula IA, and Formula IB:
In another aspect, the present disclosure provides a formulation comprising a compound having a formula of Ir(LA)n(LB)m(LC)o as described herein.
In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound having a formula of Ir(LA)n(LB)m(LC)o as described herein.
In yet another aspect, the present disclosure provides a consumer product comprising an OLED with an organic layer comprising a compound having a formula of Ir(LA)n(LB)m(LC)o as described herein.
Unless otherwise specified, the below terms used herein are defined as follows:
As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
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.
A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
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.
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 radical (C(O)—Rs).
The term “ester” refers to a substituted oxycarbonyl (—O—C(O)—Rs or —C(O)—O—Rs) radical.
The term “ether” refers to an —OR, radical.
The terms “sulfanyl” or “thio-ether” are used interchangeably and refer to a —SR, radical.
The term “selenyl” refers to a —SeRs radical.
The term “sulfinyl” refers to a —S(O)—Rs radical.
The term “sulfonyl” refers to a —SO2—Rs radical.
The term “phosphino” refers to a —P(Rs)2 radical, wherein each Rs can be same or different.
The term “silyl” refers to a —Si(Rs)3 radical, wherein each Rs can be same or different.
The term “germyl” refers to a —Ge(Rs)3 radical, wherein each Rs can be same or different.
The term “boryl” refers to a —B(Rs)2 radical or its Lewis adduct —B(Rs)3 radical, 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 deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combination thereof. Preferred 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 radicals. Preferred alkyl groups are those containing from one to fifteen 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 may be optionally substituted.
The term “cycloalkyl” refers to and includes monocyclic, polycyclic, and spiro alkyl radicals. 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 may be optionally substituted.
The terms “heteroalkyl” or “heterocycloalkyl” refer to an alkyl or a cycloalkyl radical, 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 and Se, preferably, O, S or N. Additionally, the heteroalkyl or heterocycloalkyl group may be optionally substituted.
The term “alkenyl” refers to and includes both straight and branched chain alkene radicals. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. 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 radical 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, 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 may be optionally substituted.
The term “alkynyl” refers to and includes both straight and branched chain alkyne radicals. Alkynyl groups are essentially alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.
The terms “aralkyl” or “arylalkyl” are used interchangeably and refer to an alkyl group that is substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.
The term “heterocyclic group” refers to and includes aromatic and non-aromatic cyclic radicals containing at least one heteroatom. Optionally the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably, O, S, or N. Hetero-aromatic cyclic radicals may be used interchangeably with heteroaryl. Preferred hetero-non-aromatic cyclic groups are 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 may be optionally substituted.
The term “aryl” refers to and includes both single-ring aromatic hydrocarbyl groups and polycyclic aromatic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is an aromatic hydrocarbyl group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted.
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, N, P, B, Si, and Se. In many instances, O, S, or N 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 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, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. 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 carbon atoms, 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, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.
Of the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and the respective aza-analogs of each thereof are of particular interest.
The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted, or independently substituted, with one or more General Substituents.
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, aryl, heteroaryl, sulfanyl, and combinations thereof.
In yet other instances, the Most Preferred General Substituents are selected from the group consisting of deuterium, fluorine, 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 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.
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 instance, a pair of adjacent substituents can be optionally joined or fused into a ring. The preferred ring is a five, six, or seven-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. 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, as long as they can form a stable fused ring system.
In one aspect, the present disclosure provides a compound having a formula of Ir(LA)n(LB)m(LC)o, where LA has a structure of Formula IA,
LB has a structure of Formula IB,
and LC is a bidentate ligand. In formula Ir(LA)n(LB)m(LC)o, Formula IA, and Formula IB:
In some embodiments, the compound has a formula of Ir(LA)n(LB)m, having a structure of Formula II,
where m+n=3, and each of m and n is each independently 1 or 2.
In some embodiments, each R, R′, R″, R1, R2, R3, R4, and R5 is independently hydrogen or a substituent selected from the group consisting of the Preferred General Substituents. In some embodiments, each R, R′, R″, R1, R2, R3, R4, and R5 is independently hydrogen or a substituent selected from the group consisting of the More Preferred General Substituents. In some embodiments, each R, R′, R″, R1, R2, R3, R4, and R5 is independently hydrogen or a substituent selected from the group consisting of the Most Preferred General Substituents.
In some embodiments, the compound comprises an electron-withdrawing group. In some embodiments, LA comprises an electron-withdrawing group. In some embodiments, LB comprises an electron-withdrawing group. In some embodiments, LC comprises an electron-withdrawing group.
In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 comprises an electron-withdrawing group. In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group.
In some embodiments, the electron-withdrawing group comprises one or more highly electronegative elements, including but not limited to fluorine, oxygen, sulfur, nitrogen, chlorine, and bromine.
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, the electron-withdrawn group is selected from the group consisting of the structures of the following LIST EWG 1:
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, the electron-withdrawing group is selected from the group consisting of the structures of the following LIST EWG 2:
In some embodiments, the electron-withdrawing group is selected from the group consisting of the structures of the following LIST EWG 3:
In some embodiments, the electron-withdrawing group is selected from the group consisting of the structures of the following LIST EWG 4:
In some embodiments, the electron-withdrawing group is a n-electron deficient electron-withdrawing group. In some embodiments, the n-electron deficient electron-withdrawing group is selected from the group consisting of the structures of the following LIST Pi-EWG: 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, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one of R, R′, R″, R1, R2, R3, R4, or R5 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, LA comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, LA comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, LA comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, LA comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, LA comprises at least one electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, LB comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, LB comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, LB comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, LB comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, LB comprises at least one electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, LC comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, LC comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, LC comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, LC comprises at least one electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, LC comprises at least one electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, Z2 is N and Z1 is C.
In some embodiments, Z2 is a carbene carbon and Z1 is N. In some embodiments, Z3 is N and Z4 is C. In some embodiments, Z3 and Z4 are both C. In some embodiments, Z3 is a carbene carbon and Z4 is N.
In some embodiments, moiety B is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, 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-antracene, phenanthridine, fluorene, and aza-fluorene. In some such embodiments, the aza variant includes one N on a benzo ring. In some such embodiments, the aza variant includes one N on a benzo ring and the N is bonded to the metal M.
In some embodiments, moiety B is selected from the group consisting of pyridine, thiazole, benzothiazole, imidazole, and benzimidazole. In some embodiments, moiety B is pyridine.
In some embodiments, moiety B is a monocyclic ring. In some embodiments, moiety B is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.
In some embodiments, moiety B is a polycyclic fused ring system. In some embodiments, moiety B is selected from the group consisting of naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, 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-antracene, phenanthridine, fluorene, and aza-fluorene.
In some embodiments, moiety A is selected from the group consisting of imidazole, imidazole derived carbene, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, 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, and aza-benzimidazole derived carbene. In some embodiments, moiety A is selected from the group consisting of thiazole, benzothiazole, imidazole, imidazole derived carbene, benzimidazole. In some embodiments, moiety A is imidazole or benzimidazole.
In some embodiments, each of moiety A and moiety B can independently be a polycyclic fused ring structure. In some embodiments, each of moiety A and moiety B 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 Ir and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, each of moiety A and moiety B can independently be selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and aza-variants thereof. In some such embodiments, each of moiety A and moiety B 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 A and moiety B 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 A and moiety B 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 Ir, 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 A and moiety B can independently be an aza version of the polycyclic fused rings described above. In some such embodiments, each of moiety A and moiety B can independently contain exactly one aza N atom. In some such embodiments, each of moiety A and moiety B can contain 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 position of the aza N atom is substituted.
In some embodiments, Y is selected from the group consisting of O, S, and Se. In some embodiments, Y is O. In some embodiments, Y is S. In some embodiments, Y is Se.
In some embodiments, Y is selected from the group consisting of BR, NR, and PR. In some embodiments, Y is selected from the group consisting of P(O)R, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, and SO2. In some embodiments, Y is selected from the group consisting of CRR′, SiRR′, and GeRR′. In some embodiments, Y is CR.
In some embodiments, m is 1 and n is 2. In some embodiments, m is 2 and n is 1.
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, each of X5 to X8 is C. In some embodiments, at least one of X5 to X8 is N. In some embodiments, exactly one of X5 to X8 is N.
In some embodiments, each of X9 to X12 is C. In some embodiments, at least one of X9 to X12 is N. In some embodiments, exactly one of X9 to X12 is N.
In some embodiments, at least one of X1 to X12 is N. In some embodiments, exactly one of X1 to X12 is N.
In some embodiments, each of X1 to X12 is C.
In some embodiments, moiety D is bonded to Ir by a C—Ir bond. In some embodiments, moiety D is bonded to Ir by an N—Ir bond.
In some embodiments, moiety I is fused to ring D. In some embodiments, moiety I is fused to ring E.
In some embodiments, moiety I is fused to X9 and X10. In some embodiments, moiety I is fused to X10 and X11. In some embodiments, moiety I is fused to X11 and X12.
In some embodiments, moiety I is a heterocyclic ring. In some embodiments, moiety I is selected from the group consisting of pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, and triazole.
In some embodiments, moiety I is a heterocyclic fused ring system. In some embodiments, moiety I is selected from the group consisting of 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, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, aza-phenanathrene, aza-antracene, phenanthridine, and aza-fluorene.
In some embodiments, the ring of moiety I fused directly to ring D or ring E is carbocyclic.
In some embodiments where moiety I is a heterocyclic fused ring system, the heterocyclic fused ring system of moiety I includes exactly 2 fused rings. In some embodiments where moiety I is a heterocyclic fused ring system, the heterocyclic fused ring system of moiety I includes exactly 3 fused rings.
In some embodiments, at least one R1 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one R1 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one R1 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one R1 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one R1 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, at least one R2 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one R2 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one R2 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one R2 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one R2 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, at least one R3 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one R3 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one R3 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one R3 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one R3 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, at least one R4 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one R4 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one R4 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one R4 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one R4 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, at least one R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 1 as defined herein. In some embodiments, at least one R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 2 as defined herein. In some embodiments, at least one R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 3 as defined herein. In some embodiments, at least one R5 is an electron-withdrawing group selected from the group consisting of LIST EWG 4 as defined herein. In some embodiments, at least one R5 is an electron-withdrawing group selected from the group consisting of LIST Pi-EWG as defined herein.
In some embodiments, at least one R3 is not hydrogen or deuterium.
In some embodiments, at least one R3 comprises a cyclic group. In some embodiments, at least one R3 comprises cycloalkyl, aryl, heterocycloalkyl, or heteroaryl. In some embodiments, at least one R3 comprises benzene.
In some embodiments where R3 comprises a cyclic group, the cyclic group comprises a 5-membered or 6-membered cyclic group bonded directly to moiety A. In some such embodiments, the cyclic group is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, phenanthridine, and fluorene.
In some embodiments where R3 comprises a cyclic group, at least one position adjacent to the bond with moiety A is not hydrogen or deuterium. In some embodiments where R3 comprises a cyclic group, both positions adjacent to the bond with moiety A are not hydrogen or deuterium.
In some embodiments where R3 comprises a cyclic group, at least one position adjacent to the bond with moiety A is selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl. In some embodiments where R3 comprises a cyclic group, both positions adjacent to the bond with moiety A are independently selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl.
In some embodiments where R3 comprises a cyclic group, at least one position adjacent to the bond with moiety A is alkyl. In some embodiments where R3 comprises a cyclic group, both positions adjacent to the bond with moiety A are independently alkyl.
In some embodiments where R3 comprises a cyclic group, the cyclic group is a 6-membered ring and is further substituted by a second cyclic group. In some such embodiments, the second cyclic group is cycloalkyl, aryl, heterocycloalkyl, or heteroaryl. In some such embodiments, the second cyclic group is benzene or cyclohexane. In some such embodiments, the second cyclic group is benzene. In some such embodiments, the second cyclic group is bonded para to the bond between the cyclic group and moiety A.
In some embodiments where R3 comprises a cyclic group, at least one of the cyclic group and, when present, the second cyclic group is substituted by an electron-withdrawing group. In some embodiments, each electron-withdrawing group of R3 is independently selected from the group consisting of LIST EWG1 defined herein. In some embodiments, each electron-withdrawing group of R3 is independently selected from the group consisting of LIST EWG2 defined herein. In some embodiments, each electron-withdrawing group of R3 is independently selected from the group consisting of LIST EWG3 defined herein. In some embodiments, each electron-withdrawing group of R3 is independently selected from the group consisting of LIST EWG4 defined herein. In some embodiments, each electron-withdrawing group of R3 is independently selected from the group consisting of LIST PI-EWG defined herein. In some embodiments, each electron-withdrawing group is independently F or CF3.
In some embodiments, at least one R4 is not hydrogen or deuterium.
In some embodiments, at least one R4 comprises a cyclic group. In some embodiments, at least one R4 comprises cycloalkyl, aryl, heterocycloalkyl, or heteroaryl. In some embodiments, at least one R4 comprises benzene.
In some embodiments where R4 comprises a cyclic group, the cyclic group comprises a 5-membered or 6-membered cyclic group bonded directly to moiety B. In some such embodiments, the cyclic group is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, phenanthridine, and fluorene.
In some embodiments where R4 comprises a cyclic group, at least one position adjacent to the bond with moiety B is not hydrogen or deuterium. In some embodiments where R4 comprises a cyclic group, both positions adjacent to the bond with moiety B are not hydrogen or deuterium.
In some embodiments where R4 comprises a cyclic group, at least one position adjacent to the bond with moiety B is selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl. In some embodiments where R4 comprises a cyclic group, both positions adjacent to the bond with moiety B are independently selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl.
In some embodiments where R4 comprises a cyclic group, at least one position adjacent to the bond with moiety B is alkyl. In some embodiments where R4 comprises a cyclic group, both positions adjacent to the bond with moiety B are independently alkyl.
In some embodiments where R4 comprises a cyclic group, the cyclic group is a 6-membered ring and is further substituted by a second cyclic group. In some such embodiments, the second cyclic group is cycloalkyl, aryl, heterocycloalkyl, or heteroaryl. In some such embodiments, the second cyclic group is benzene or cyclohexane. In some such embodiments, the second cyclic group is benzene. In some such embodiments, the second cyclic group is bonded para to the bond between the cyclic group and moiety B.
In some embodiments where R4 comprises a cyclic group, at least one of the cyclic group and, when present, the second cyclic group is substituted by an electron-withdrawing group. In some embodiments, each electron-withdrawing group of R4 is independently selected from the group consisting of LIST EWG1 defined herein. In some embodiments, each electron-withdrawing group of R4 is independently selected from the group consisting of LIST EWG2 defined herein. In some embodiments, each electron-withdrawing group of R4 is independently selected from the group consisting of LIST EWG3 defined herein. In some embodiments, each electron-withdrawing group of R4 is independently selected from the group consisting of LIST EWG4 defined herein. In some embodiments, each electron-withdrawing group of R4 is independently selected from the group consisting of LIST PI-EWG defined herein. In some embodiments, each electron-withdrawing group of R4 is independently F or CF3.
In some embodiments, at least one R5 is not hydrogen or deuterium. In some embodiments, at least one R5 is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated, partially or fully fluorinated, and combinations thereof.
In some embodiments, two R5 are joined or fused together to form a ring. In some such embodiments, two R5 are joined or fused together to form a ring selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, triazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, aza-benzofuran, benzoxazole, aza-benzoxazole, benzothiophene, aza-benzothiophene, benzothiazole, aza-benzothiazole, benzoselenophene, aza-benzoselenophene, indene, aza-indene, indole, aza-indole, benzimidazole, aza-benzimidazole, carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, quinoxaline, phthalazine, phenanthrene, aza-phenanathrene, anthracene, aza-antracene, phenanthridine, fluorene, and aza-fluorene.
In some embodiments, moiety I is selected from the group consisting of pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, and phenanthridine.
In some embodiments, ligand LA is selected from the group consisting of the structures of the following LIST 1:
wherein:
In some embodiments where ligand LA is selected from LIST 1, at least one of RAA, or RDE is partially or fully deuterated. In some embodiments, at least one RAA is partially or fully deuterated. In some embodiments, at least one RDE is partially or fully deuterated.
In some embodiments where ligand LA is selected from LIST 1, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 1 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 2 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 3 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 4 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST Pi-EWG as defined herein.
In some embodiments where ligand LA is selected from LIST 1, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 1 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 2 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 3 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 4 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST Pi-EWG as defined herein.
In some embodiments, each of X13 to X16 is C. In some embodiments, at least one of X13 to X16 is N.
In some embodiments, each of T1 to T4 is C. In some embodiments, at least one of T1 to T4 is N.
In some embodiments, the ligand LA is selected from the group consisting of the structures of the following LIST 2:
wherein:
In some embodiments where ligand LA is selected from LIST 2, at least one of RAA, or RDE is partially or fully deuterated. In some embodiments, at least one RAA is partially or fully deuterated. In some embodiments, at least one RDE is partially or fully deuterated.
In some embodiments where ligand LA is selected from LIST 2, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 1 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 2 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 3 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST EWG 4 as defined herein. In some embodiments, at least one RAA is or comprises an electron-withdrawing group from the LIST Pi-EWG as defined herein.
In some embodiments where ligand LA is selected from LIST 2, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 1 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 2 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 3 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST EWG 4 as defined herein. In some embodiments, at least one RDE is or comprises an electron-withdrawing group from the LIST Pi-EWG as defined herein.
In some embodiments, each of X13 to X16 is C. In some embodiments, at least one of X13 to X16 is N.
In some embodiments of the compound that comprises one or more of R, R′, R″, R1, R2, R3, R4, R5, RAA, and RDE, at least one of the substituents R, R′, R″, R1, R2, R3, R4, R5, RAA, and RDE is partially or fully deuterated. In some embodiments of the compound that comprises at least one R′, at least one R′ is partially or fully deuterated. In some embodiments of the compound that comprises at least one R″, at least one R″ is partially or fully deuterated. In some embodiments of the compound that comprises at least one R1, at least one R1 is partially or fully deuterated. In some embodiments of the compound that comprises at least one R2, at least one R2 is partially or fully deuterated. In some embodiments that comprise at least one R3, the at least one R3 is partially or fully deuterated. In some embodiments of the compound that comprises at least one R4, at least one R4 is partially or fully deuterated. In some embodiments of the compound that comprises at least one R5, at least one R5 is partially or fully deuterated. In some embodiments of the compound that comprises at least one RAA, at least one RAA is partially or fully deuterated. In some embodiments of the compound that comprises at least one RDE, at least one RDE is partially or fully deuterated.
In some embodiments, ligand LA is selected from the group consisting of LAi, wherein i is an integer from 1 to 109, and each of LA1 to LA109 is defined in the following LIST 3:
In some embodiments, the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); and wherein LA, LB, and LC are different from each other.
In some embodiments, LB is a substituted or unsubstituted phenylpyridine, and LC is a substituted or unsubstituted acetylacetonate.
In some embodiments, LB and LC are each independently selected from the group consisting of the structures of the following LIST 4:
wherein:
In some embodiments, LB and LC are each independently selected from the group consisting of the structures of the following LIST 5:
In some embodiments, LA can be selected from LAi, wherein i is an integer from 1 to 90; and LB can be selected from LBk, wherein k is an integer from 1 to 474, wherein:
In some embodiments, the compound is selected from the group consisting of only those compounds whose LBk corresponds to one of the following: LB1, LB2, LB18, LB28, LB38, LB108, LB118, LB122, LB124, LB126, LB128, LB130, LB132, LB134, LB136, LB138, LB140, LB142, LB144, LB156, LB158, LB160, LB162, LB164, LB168, LB172, LB175, LB204, LB206, LB214, LB216, LB218, LB220, LB222, LB231, LB233, LB235, LB237, LB240, LB242, LB244, LB246, LB248, LB250, LB252, LB254, LB256, LB258, LB260, LB262, LB264, LB265, LB266, LB267, LB268, LB269, and LB270.
In some embodiments, the compound is selected from the group consisting of only those compounds whose LBk corresponds to one of the following: LB1, LB2, LB18, LB28, LB38, LB108, LB118, LB122, LB126, LB128, LB132, LB136, LB138, LB142, LB156, LB162, LB204, LB206, LB214, LB216, LB218, LB220, LB231, LB233, LB237, LB264, LB265, LB266, LB267, LB268, LB269, and LB270.
In some embodiments, LA is selected from the group consisting of the structures of LIST 1, LIST 2, and LIST 3, and LB is selected from the group consisting of the structures of LIST 4, LIST 5, and LIST 6. In some embodiments, LA is selected from the group consisting of the structures of LIST 1 and LB is selected from the group consisting of the structures of LIST 6. In some embodiments, LA is selected from the group consisting of the structures of LIST 2 and LB is selected from the group consisting of the structures of LIST 6. In some embodiments, LA is selected from LIST 3 of LAi consisting of LA1 to LA90 defined herein, wherein i is an integer from 1 to 90, and LB is selected from the group consisting of the structures of LIST 6 of LBk wherein k is an integer from 1 to 474.
In some embodiments, the compound can be Ir(LA)2(LB), Ir(LA)(LB)2, or Ir(LA)(LB)(LC). In some of these embodiments, LA can have a Formula IA as defined herein. In some of these embodiments, LB can have a Formula IB as defined herein. In some of these embodiments, LC can be selected from LIST 1, LIST 2, LIST 3, LIST 4, LIST 5, LIST 6, so long as it is not identical to either LA or LB in the same molecule. In some of these embodiments, LA can be selected from the group consisting of the structures of LIST 1, LIST 2, and LIST 3 as defined herein. In some of these embodiments, LB can be selected from the group consisting of the structures of LIST 4, LIST 5, and LIST 6 as defined herein. In some of these embodiments, the compound can be Ir(LAi)2(LB), Ir(LAi)(LB)2, Ir(LA)2(LBk), Ir(LA)(LBk)2, Ir(LAi)2(LBk) consisting of the compounds of Ir(LA1)2(LB1) to Ir(LA90)2(LB474), Ir(LAi)(LBk)2 consisting of the compounds of Ir(LA1)(LB1)2 to Ir(LA90)(LB474)2, Ir(LA)(LBk)(LC), Ir(LAi)(LB)(LC), or Ir(LAi(LBk)(LC).
In some embodiments, the compound is selected from the group consisting of the structures of the following LIST 7:
In some embodiments, the compound having a formula of Ir(LA)n(LB)m(LC)o as described herein can be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, percent deuteration has its ordinary meaning and includes the percent of possible hydrogen atoms (e.g., positions that are hydrogen or deuterium) that are replaced by deuterium atoms.
In some embodiments of heteroleptic compound having the formula of Ir(LA)n(LB)m(LC)o as defined above, the ligand LA has a first substituent RI, where the first substituent RI has a first atom a-I that is the farthest away from the metal M among all atoms in the ligand LA. Additionally, the ligand LB, if present, has a second substituent RII, where the second substituent RII has a first atom a-II that is the farthest away from the metal M among all atoms in the ligand LB. Furthermore, the ligand Lc, if present, has a third substituent RIII, where the third substituent RIII has a first atom a-III that is the farthest away from the metal M among all atoms in the ligand LC.
In such heteroleptic compounds, vectors VD1, VD2, and VD3 can be defined that are defined as follows. VD1 represents the direction from the metal M to the first atom a-I and the vector VD1 has a value D1 that represents the straight line distance between the metal M and the first atom a-I in the first substituent RI. VD2 represents the direction from the metal M to the first atom a-II and the vector VD2 has a value D2 that represents the straight line distance between the metal M and the first atom a-II in the second substituent RII. VD3 represents the direction from the metal M to the first atom a-III and the vector VD3 has a value D3 that represents the straight line distance between the metal M and the first atom a-III in the third substituent RIII.
This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Applications No. 63/497,148, filed on Apr. 19, 2023, No. 63/459,773, filed on Apr. 17, 2023, No. 63/459,415, filed on Apr. 14, 2023, No. 63/488,719, filed on Mar. 6, 2023, No. 63/484,004, filed on Feb. 9, 2023, and No. 63/482,344, filed on Jan. 31, 2023, the entire contents of which are incorporated herein by reference.
| Number | Date | Country | |
|---|---|---|---|
| 63482344 | Jan 2023 | US | |
| 63459415 | Apr 2023 | US | |
| 63484004 | Feb 2023 | US | |
| 63459773 | Apr 2023 | US | |
| 63488719 | Mar 2023 | US | |
| 63497148 | Apr 2023 | US |
