US20240025934A1 - Organic electroluminescent materials and devices - Google Patents

Organic electroluminescent materials and devices Download PDF

Info

Publication number
US20240025934A1
US20240025934A1 US18/357,242 US202318357242A US2024025934A1 US 20240025934 A1 US20240025934 A1 US 20240025934A1 US 202318357242 A US202318357242 A US 202318357242A US 2024025934 A1 US2024025934 A1 US 2024025934A1
Authority
US
United States
Prior art keywords
compound
group
ligand
ring
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
US18/357,242
Inventor
Pierre-Luc T. Boudreault
Eric A. MARGULIES
Bert Alleyne
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universal Display Corp
Original Assignee
Universal Display Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Universal Display Corp filed Critical Universal Display Corp
Priority to US18/357,242 priority Critical patent/US20240025934A1/en
Assigned to UNIVERSAL DISPLAY CORPORATION reassignment UNIVERSAL DISPLAY CORPORATION NUNC PRO TUNC ASSIGNMENT (SEE DOCUMENT FOR DETAILS). Assignors: MARGULIES, ERIC A., ALLEYNE, BERT, BOUDREAULT, PIERRE-LUC T.
Publication of US20240025934A1 publication Critical patent/US20240025934A1/en
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of 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. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • 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. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
  • 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.
  • 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 EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.
  • a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the following structure:
  • 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.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • 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.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • solution processible 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.
  • 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.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • 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.
  • 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.
  • a series of new phosphorescent metal complexes based on ligands containing naphthalene-pyridine derivatives are disclosed. Further functionalization of these moieties allows fine tuning of the properties of the fmal complexes, such as color of the light emission, the light emitting efficiency and emission lifetime.
  • a compound that comprises a ligand L A of Formula I
  • ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring; each R A , R B , and R C independently represents mono to the maximum allowable number of substitutions, or no substitution; each R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; at least one R A has the formula —CH 2 R or —CHRR′; each R C and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof; L A is complexed to a metal M; M is optionally coordinated to other ligands; the ligand L A is optionally linked with other ligands to comprise a tri
  • An OLED comprising the compound of the present disclosure in an organic layer therein is also disclosed.
  • a consumer product comprising the OLED is also disclosed.
  • FIG. 1 shows an organic light emitting device
  • FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
  • an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • the anode injects holes and the cathode injects electrons into the organic layer(s).
  • the injected holes and electrons each migrate toward the oppositely charged electrode.
  • an “exciton,” which is a localized electron-hole pair having an excited energy state is formed.
  • Light is emitted when the exciton relaxes via a photoemissive mechanism.
  • the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • the initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • FIG. 1 shows an organic light emitting device 100 .
  • Device 100 may include a substrate 110 , an anode 115 , a hole injection layer 120 , a hole transport layer 125 , an electron blocking layer 130 , an emissive layer 135 , a hole blocking layer 140 , an electron transport layer 145 , an electron injection layer 150 , a protective layer 155 , a cathode 160 , and a barrier layer 170 .
  • Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164 .
  • Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.
  • each of these layers are available.
  • a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety.
  • An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety.
  • An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • the theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No.
  • FIG. 2 shows an inverted OLED 200 .
  • the device includes a substrate 210 , a cathode 215 , an emissive layer 220 , a hole transport layer 225 , and an anode 230 .
  • Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230 , device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200 .
  • FIG. 2 provides one example of how some layers may be omitted from the structure of device 100 .
  • FIGS. 1 and 2 The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
  • the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
  • Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
  • hole transport layer 225 transports holes and injects holes into emissive layer 220 , and may be described as a hole transport layer or a hole injection layer.
  • an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2 .
  • OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety.
  • PLEDs polymeric materials
  • OLEDs having a single organic layer may be used.
  • OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety.
  • the OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2 .
  • the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • Other suitable deposition methods include spin coating and other solution based processes.
  • Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and organic vapor jet printing (OVJP). Other methods may also be used.
  • the materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
  • Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer.
  • a barrier layer One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc.
  • the barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge.
  • the barrier layer may comprise a single layer, or multiple layers.
  • the barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer.
  • the barrier layer may incorporate an inorganic or an organic compound or both.
  • the preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties.
  • the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time.
  • the weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95.
  • the polymeric material and the non-polymeric material may be created from the same precursor material.
  • the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
  • Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein.
  • a consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed.
  • Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays.
  • Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, a light therapy device, and a sign.
  • control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from ⁇ 40 degree C. to +80 degree C.
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • halo halogen
  • halide halogen
  • fluorine chlorine, bromine, and iodine
  • acyl refers to a substituted carbonyl radical (C(O)—R s ).
  • esters refers to a substituted oxycarbonyl (—O—C(O)—R s or —C(O)—O—R s ) radical.
  • ether refers to an —OR radical.
  • sulfanyl or “thio-ether” are used interchangeably and refer to a —SR s radical.
  • sulfinyl refers to a —S(O)—R s radical.
  • sulfonyl refers to a —SO 2 —R s radical.
  • phosphino refers to a —P(R s ) 3 radical, wherein each R s can be same or different.
  • sil refers to a —Si(R s ) 3 radical, wherein each R s can be same or different.
  • R 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 & is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.
  • 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 is optionally substituted.
  • 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 is optionally substituted.
  • heteroalkyl or “heterocycloalkyl” refer to an alkyl or a cycloalkyl radical, respectively, having at least one carbon atom replaced by a heteroatom.
  • the at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably, O, S or N.
  • the heteroalkyl or heterocycloalkyl group is optionally substituted.
  • 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.
  • heteroalkenyl refers to an alkenyl radical having at least one carbon atom replaced by a heteroatom.
  • 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 is optionally substituted.
  • alkynyl refers to and includes both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group is optionally substituted.
  • aralkyl or “arylalkyl” are used interchangeably and refer to an alkyl group that is substituted with an aryl group. Additionally, the aralkyl group is optionally substituted.
  • heterocyclic group refers to and includes aromatic and non-aromatic cyclic radicals containing at least one heteroatom.
  • 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.
  • 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 is optionally substituted.
  • 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, qui
  • 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.
  • 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.
  • the general substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
  • the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.
  • the more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
  • substitution refers to a substituent other than H that is bonded to the relevant position, e.g., a carbon or nitrogen.
  • R 1 when R 1 represents mono-substitution, then one R 1 must be other than H (i.e., a substitution).
  • R 1 when R 1 represents di-substitution, then two of R 1 must be other than H.
  • R 1 when R 1 represents no substitution, R 1 , 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.
  • substitution includes a combination of two to four of the listed groups.
  • substitution includes a combination of two to three groups.
  • 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.
  • aza-dibenzofuran i.e. aza-dibenzofuran, aza-dibenzothiophene, etc.
  • azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline.
  • 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.
  • 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.
  • “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.
  • a series of new phosphorescent metal complexes based on ligands containing naphthalene-pyridine derivatives are disclosed. Further functionalization of these moieties allows fine tuning of the properties of the final complexes, such as color of the light emission, the light emitting efficiency and emission lifetime.
  • the presence of the naphthalene moiety in the ligands allows bathochromic shift in the light emission by the phosphorescent metal complexes compared to the traditional phenylpyridine ligands. This shift enables tuning the emission peak wavelength, ⁇ MAX , of the metal complexes to be between yellow and red, i.e. amber/orange.
  • the ligands have to contain substituents, R A and R H , as aliphatic side chains or fluorinated aliphatic side chains.
  • the side chains allow fine tuning of the color of the emission of the metal complexes and also increases their external quantum efficiencies (EQEs).
  • EQEs external quantum efficiencies
  • the use of branched side chains can also lead to desired narrow emission line shape and improves the thermal properties of the final material by lowering the sublimation temperature.
  • a compound that comprises a ligand L A of Formula I
  • ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring; each R A , R B , and R C independently represents mono to the maximum allowable number of substitutions, or no substitution; each R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; at least one R A has the formula —CH 2 R or —CHRR′; each R C and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof; L A is complexed to a metal M; M is optionally coordinated to other ligands; the ligand L A is optionally linked with other ligands to comprise a tri
  • R and R′ is independently selected from the group consisting of alkyl, cycloalkyl, D variant, F variant, and combinations thereof.
  • each R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of the preferred general substituents defined above.
  • M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au. In some embodiments, M is Ir or Pt. In some embodiments, M is Ir(III) or Pt(II).
  • R is selected from the group consisting of alkyl, cycloalkyl, partially fluorinated variants thereof, partially or fully deuterated variants thereof, and combination thereof.
  • the compound comprises a substituted or unsubstituted acetylacetone ligand.
  • At least one R B comprises a cyclohexyl or tert-butyl group.
  • ring C is selected from the group consisting of benzene, pyridine, pyrimidine, pyrazine, and pyridazine. In some embodiments, ring C is a furan or thiofuran ring.
  • the ligand L A is selected from the group consisting of:
  • the ligand L A is selected from the group consisting of: L A1 through L A448 based on the structure of Formula II
  • R 1 , R 2 , and G are defined as:
  • R 1 , R 2 , and G are defined as:
  • R 1 , R 2 , and G are defined as:
  • R 1 , R 2 , and G are defined as:
  • R B1 to R B42 have the following structures:
  • the compound has a formula of M(L A ) x (L B ) y (L C ) z , wherein L A is selected from the group consisting of L A1 to L A179 , and L B and L C are each a bidentate ligand; and x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.
  • the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ), wherein L A , L B , and L C are as defined above; and wherein L A , L B , and L C are different from each other.
  • the compound has a formula of Pt(L A )(L B ); wherein L A , L B , and L C are as defined above, and wherein L A and L B can be same or different.
  • the L A and L B are connected to form a tetradentate ligand.
  • the compound having the formula of M(L A ) x (L B ) y (L C ) z defined above, L B and L C are each independently selected from the group consisting of:
  • each Y 1 to Y 3 are independently selected from the group consisting of carbon and nitrogen;
  • Y′ is selected from the group consisting of B R e , N R e , P R e , O, S, Se, C ⁇ O, S ⁇ O, SO 2 , CR e R f , SiR e R f , and GeR e R f , R e and R f are optionally fused or joined to form a ring;
  • each R a , R b , R c and R d may independently represent from mono substitution to the maximum possible number of substitutions, or no substitution;
  • each R a , R b , R c , R d , R e , and R f is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; and any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a
  • the compound having the formula of M(L A ) x (L B ) y (L C ) z defined above, L B and L C are each independently selected from the group consisting of:
  • each L Cj has a structure of Formula X
  • R 1 , R 2 , and R 3 are defined as:
  • an organic light emitting device comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode.
  • the organic layer comprises the compound comprising the ligand L A of Formula I
  • a consumer product also disclosed that comprises the OLED whose organic layer comprises the compound comprising the ligand L A of Formula I described herein.
  • the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.
  • the OLED further comprises a layer comprising a delayed fluorescent emitter.
  • the OLED comprises a RGB pixel arrangement or white plus color filter pixel arrangement.
  • the OLED is a mobile device, a hand held device, or a wearable device.
  • the OLED is a display panel having less than 10 inch diagonal or 50 square inch area.
  • the OLED is a display panel having at least 10 inch diagonal or 50 square inch area.
  • the OLED is a lighting panel.
  • the emissive region comprises the compound comprising the ligand L A of Formula I
  • the compound is an emissive dopant or a non-emissive dopant.
  • the emissive region further comprises a host, wherein the host contains at least one group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
  • the emissive region further comprises a host, wherein the host is selected from the group consisting of:
  • the compound can be an emissive dopant.
  • the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. application Ser. No. 15/700,352, published on Mar. 14, 2019 as U.S. patent application publication No. 2019/0081248, which is hereby incorporated by reference in its entirety), triplet-triplet annihilation, or combinations of these processes.
  • the emissive dopant can be a racemic mixture, or can be enriched in one enantiomer.
  • the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from others).
  • the ligands can all be the same in some embodiments. In some other embodiments, at least one ligand is different from the other ligand(s). In some embodiments, every ligand can be different from each other. This is also true in embodiments where a ligand being coordinated to a metal can be linked with other ligands being coordinated to that metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, where the coordinating ligands are being linked together, all of the ligands can be the same in some embodiments, and at least one of the ligands being linked can be different from the other ligand(s) in some other embodiments.
  • the compound can be used as a phosphorescent sensitizer in an OLED where one or multiple layers in the OLED contains an acceptor in the form of one or more fluorescent and/or delayed fluorescence emitters.
  • the compound can be used as one component of an exciplex to be used as a sensitizer.
  • the compound must be capable of energy transfer to the acceptor and the acceptor will emit the energy or further transfer energy to a final emitter.
  • the acceptor concentrations can range from 0.001% to 100%.
  • the acceptor could be in either the same layer as the phosphorescent sensitizer or in one or more different layers.
  • the acceptor is a TADF emitter.
  • the acceptor is a fluorescent emitter.
  • the emission can arise from any or all of the sensitizer, acceptor, and final emitter.
  • a formulation comprising the compound described herein is also disclosed.
  • the OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel.
  • the organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.
  • the organic layer can also include a host.
  • a host In some embodiments, two or more hosts are preferred.
  • the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport.
  • the host can include a metal complex.
  • the host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan.
  • Any substituent in the host can be an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH ⁇ CH—C n H 2n+1 , C ⁇ C—C n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n —Ar 1 , or the host has no substitutions.
  • n can range from 1 to 10; and Ar 1 and Ar 2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
  • the host can be an inorganic compound, for example a Zn containing inorganic material e.g. ZnS.
  • the host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
  • the host can include a metal complex.
  • the host can be, but is not limited to, a specific compound selected from the group consisting of:
  • a formulation that comprises the novel compound disclosed herein is described.
  • the formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, electron blocking material, hole blocking material, and an electron transport material, disclosed herein.
  • the present disclosure encompasses any chemical structure comprising the novel compound of the present disclosure, or a monovalent or polyvalent variant thereof.
  • the inventive compound, or a monovalent or polyvalent variant thereof can be a part of a larger chemical structure.
  • Such chemical structure can be selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule (also known as supermolecule).
  • a “monovalent variant of a compound” refers to a moiety that is identical to the compound except that one hydrogen has been removed and replaced with a bond to the rest of the chemical structure.
  • a “polyvalent variant of a compound” refers to a moiety that is identical to the compound except that more than one hydrogen has been removed and replaced with a bond or bonds to the rest of the chemical structure. In the instance of a supramolecule, the inventive compound can also be incorporated into the supramolecule complex without covalent bonds.
  • the materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device.
  • emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present.
  • the materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
  • a charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity.
  • the conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved.
  • Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.
  • Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.
  • aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
  • Each of Ar 1 to Ar 9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine
  • Each Ar may be unsubstituted or may be substituted by 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, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkeny
  • Ar 1 to Ar 9 is independently selected from the group consisting of:
  • k is an integer from 1 to 20;
  • X 101 to X 108 is C (including CH) or N;
  • Z 101 is NAr 1 , O, or S;
  • Ar 1 has the same group defined above.
  • metal complexes used in HIL or HTL include, but are not limited to the following general formula:
  • Met is a metal, which can have an atomic weight greater than 40;
  • (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 are independently selected from C, N, O, P, and S;
  • L 101 is an ancillary ligand;
  • k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and
  • k′+k′′ is the maximum number of ligands that may be attached to the metal.
  • (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another aspect, (Y 101 -Y 102 ) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc + /Fc couple less than about 0.6 V.
  • Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Ser.
  • An electron blocking layer may be used to reduce the number of electrons and/or excitons that leave the emissive layer.
  • the presence of such a blocking layer in a device may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer.
  • a blocking layer may be used to confine emission to a desired region of an OLED.
  • the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface.
  • the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface.
  • the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.
  • the light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material.
  • the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.
  • metal complexes used as host are preferred to have the following general formula:
  • Met is a metal
  • (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 are independently selected from C, N, O, P, and S
  • L 101 is an another ligand
  • k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal
  • k′+k′′ is the maximum number of ligands that may be attached to the metal.
  • the metal complexes are:
  • (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
  • Met is selected from Ir and Pt.
  • (Y 103 -Y 104 ) is a carbene ligand.
  • the host compound contains at least one of the following groups selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadia
  • Each option within each group may be unsubstituted or may be substituted by 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, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • the host compound contains at least one of the following groups in the molecule:
  • R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
  • k is an integer from 0 to 20 or 1 to 20.
  • X 101 to X 108 are independently selected from C (including CH) or N.
  • Z 101 and Z 102 are independently selected from NR 101 , O, or S.
  • Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S.
  • One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure.
  • the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials.
  • suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
  • Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No.
  • a hole blocking layer may be used to reduce the number of holes and/or excitons that leave the emissive layer.
  • the presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer.
  • a blocking layer may be used to confine emission to a desired region of an OLED.
  • the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than the emitter closest to the HBL interface.
  • the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
  • compound used in HBL contains the same molecule or the same functional groups used as host described above.
  • compound used in HBL contains at least one of the following groups in the molecule:
  • Electron transport layer may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.
  • compound used in ETL contains at least one of the following groups in the molecule:
  • R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
  • Ar 1 to Ar 3 has the similar definition as Ar's mentioned above.
  • k is an integer from 1 to 20.
  • X 101 to X 108 is selected from C (including CH) or N.
  • the metal complexes used in ETL contains, but not limit to the following general formula:
  • (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L 101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
  • Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S.
  • the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually.
  • Typical CGL materials include n and p conductivity dopants used in the transport layers.
  • the hydrogen atoms can be partially or fully deuterated.
  • any specifically listed substituent such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof.
  • classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.
  • the reaction mixture was then cooled to room temperature and diluted with water (50 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2 ⁇ 100 mL). The combined organic layers were washed with brine (2 ⁇ 100 mL), dried over by sodium sulfate, filtered and concentrated under reduced pressure.
  • the crude product was dissolved in 50% dichloromethane in hexane and passed through a pad of basic alumina (30 g), rinsing with 50% dichloromethane in hexane (50 mL). The product (4.4 g) was recrystallized from methanol to give 2-(4-cyclohexylnaphthalen-2-yl)pyridine (4.21 g, 83% yield) as a white solid.
  • Powdered potassium carbonate (1.2 g, 8.4 mmol) was added and the reaction mixture stirred at room temperature in the dark for 5 hours.
  • DIUF Water 25 mL was added, the slurry was stirred for 1 hour, filtered, and the solid was washed with water (3 ⁇ 5 mL) and ethanol (3 ⁇ 5 mL) then air-dried.
  • the orange solid ( ⁇ 2 g) was loaded onto a column of silica gel (50 g), eluting with 1:1 dichloromethane and hexanes (250 mL). The cleanest product fractions were concentrated and the solid was dried in a vacuum oven at 50° C.
  • the reaction mixture was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2 ⁇ 100 mL). The combined organic layers were washed with brine (2 ⁇ 100 mL), dried over by sodium sulfate, filtered and concentrated under reduced pressure.
  • the crude product was dissolved in 50% dichloromethane in hexane and passed through a pad of basic alumina (30 g), rinsing with 50% dichloromethane in hexane (50 mL), and the filtrate was concentrated under reduced pressure.
  • reaction mixture was cooled to ⁇ 50° C., filtered, the solids washed with water (30 mL) then air-dried for 10 minutes to give the compound CC3, di-p-chloro-tetrakis[(2-(4-cyclohexylnaphthalen-2-yl)-4-(trifluoromethyl) pyridine-2-yl)]diiridium(III) (5.5 g, crude) as a reddish solid.
  • the reaction mixture was cooled to room temperature and diluted with water (5 mL) and ethyl acetate (60 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (2 ⁇ 60 mL). The combined organic layers were washed with saturated brine (2 ⁇ 60 mL), dried over sodium sulfate, filtered and concentrate under reduced pressure.
  • the impure product (6.74 g) was chromatograph-ed on silica gel, eluting with 33-66% dichloromethane in hexane. Product fractions were concentrated under reduced pressure and the solid recrystallized from methanol to give 4-(tert-butyl)-2-(4-cyclohexylnaphthalen-2-yl)pyridine (2.6 g, 89% yield).
  • the reaction mixture was cooled to room temperature, filtered and the solids washed with water (50 mL) and ethanol (100 mL).
  • the solids were dissolved in dichloromethane (30 mL), adsorbed onto silica gel (50 g) and purified by chromatography, eluting with 0-5% ethyl acetate in heptanes, to give 2-(4-cyclohexylnaphthalen-2-yl)-4-(3,3,3-trifluoro-2,2-dimethyl-propyl)pyridine (7.0 g, 85% yield) as a white solid.
  • All example devices were fabricated by high vacuum ( ⁇ 10-7 Torr) thermal evaporation.
  • the anode electrode was 1150 ⁇ of indium tin oxide (ITO).
  • the cathode consisted of 10 ⁇ of Liq (8-hydroxyquinoline lithium) followed by 1,000 ⁇ of A1. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box ( ⁇ 1 ppm of H 2 O and O 2 ) immediately after fabrication, and a moisture getter was incorporated inside the package.
  • the organic stack of the device examples consisted of sequentially, from the ITO surface, 100 ⁇ of LG101 (purchased from LG chem) as the hole injection layer (HIL); 400 ⁇ of HTM as a hole transporting layer (HTL); 300 ⁇ of an emissive layer (EML) containing Compound H as a host, a stability dopant (SD) (18%), and Comparative Compound 1, 2, 3, and 4 (CC1, CC2, CC3, CC4) or Compound C88,222 as the emitter (3%); 100 ⁇ of Compound H as a blocking layer; and 350 ⁇ of Liq (8-hydroxyquinoline lithium) doped with 40% of ETM as the ETL.
  • the emitter was selected to provide the desired color, efficiency and lifetime.
  • the stability dopant (SD) was added to the electron-transporting host to help transport positive charge in the emissive layer.
  • the Comparative Example devices were fabricated similarly to the device examples except that Comparative Compounds were used as the emitters in the EML. Table 1 below provides the materials used for the device layers and the layer thickness.
  • the device performance data are summarized in Table 2 below.
  • the maximum wavelength of emission ( ⁇ max ) is very comparable for all comparative compounds (589, 584, 584 nm) and Compound C88,222 (589 nm).
  • the exception is Compound CC3 where a CF3 pendant group was added on the pyridine (631 nm), showing that electron-withdrawing groups on the pyridine lead to bathochromic shift of the emission from an orange color to a deep red color (much lower energy). Since device performance can only be compared with the similar emitting color, it is not suitable to compare CC3 with others tested here except the large color change.
  • the line shape of the emission (FHWM) is similar going from comparative compounds with similar emitting colors to Compound C88,222.
  • the EQE of Compound C88,222 (1.00) was much higher than the EQE of all Comparative Compounds with similar emitting colors (CC1—0.74, CC2—0.81, CC4—0.81).
  • the addition of flexible branched side chains on pyridine units can be responsible this increase in efficiency.
  • the device lifetime (LT 95% at 80 mA/cm 2 ) was also better in the case of Compound C88,222 (1.00) compared to the Comparative Compounds with similar emitting colors (CC1—0.28, CC2—0.44, CC4—C0.34).

Abstract

A compound is disclosed that includes a ligand LA of Formula Iwhere ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring; each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution; LA is complexed to a metal M; M is optionally coordinated to other ligands; the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and any two substituents of RB and RC may be joined or fused together to form a ring.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • This application is a continuation of U.S. patent application Ser. No. 16/442,839, filed Jun. 17, 2019, which claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 62/696,383, filed Jul. 11, 2018, the entire contents of which are incorporated herein by reference.
    • FIELD
  • The present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.
    • BACKGROUND
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of 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. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • 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. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
  • 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 EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.
  • One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the following structure:
  • Figure US20240025934A1-20240125-C00002
  • In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.
  • 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 processible” 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.
  • More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.
    • SUMMARY
  • A series of new phosphorescent metal complexes based on ligands containing naphthalene-pyridine derivatives are disclosed. Further functionalization of these moieties allows fine tuning of the properties of the fmal complexes, such as color of the light emission, the light emitting efficiency and emission lifetime.
  • A compound is disclosed that comprises a ligand LA of Formula I
  • Figure US20240025934A1-20240125-C00003
  • where ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring; each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution; each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; at least one RA has the formula —CH2R or —CHRR′; each RC and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof; LA is complexed to a metal M; M is optionally coordinated to other ligands; the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and any two substituents of RB and RC may be joined or fused together to form a ring.
  • An OLED comprising the compound of the present disclosure in an organic layer therein is also disclosed.
  • A consumer product comprising the OLED is also disclosed.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 shows an organic light emitting device.
  • FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
    •  DETAILED DESCRIPTION
  • Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.
  • FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.
  • More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.
  • FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
  • The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2 .
  • Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2 . For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
  • Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and organic vapor jet printing (OVJP). Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise a single layer, or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
  • Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. A consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, a light therapy device, and a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.
  • The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.
  • 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 —SRs 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)3 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.
  • In each of the above, R 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 & 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 is 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 is 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 is 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 is optionally substituted.
  • The term “alkynyl” refers to and includes both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group is 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 is 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 is 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 is 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, 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, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
  • In some instances, the 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 more 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 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.
  • A series of new phosphorescent metal complexes based on ligands containing naphthalene-pyridine derivatives are disclosed. Further functionalization of these moieties allows fine tuning of the properties of the final complexes, such as color of the light emission, the light emitting efficiency and emission lifetime.
  • The presence of the naphthalene moiety in the ligands allows bathochromic shift in the light emission by the phosphorescent metal complexes compared to the traditional phenylpyridine ligands. This shift enables tuning the emission peak wavelength, λMAX, of the metal complexes to be between yellow and red, i.e. amber/orange. The ligands have to contain substituents, RA and RH, as aliphatic side chains or fluorinated aliphatic side chains. The side chains allow fine tuning of the color of the emission of the metal complexes and also increases their external quantum efficiencies (EQEs). The use of branched side chains can also lead to desired narrow emission line shape and improves the thermal properties of the final material by lowering the sublimation temperature.
  • There are significant challenges in developing amber/orange emitting metal complexes. For metal complexes containing diketone-based ancillary ligands, they are usually not stable enough to be commercially viable. For heteroleptic metal complexes, the emission is broad and their EQE are low. The novel ligands disclosed herein exhibit improvements in these categories making them attractive options for amber/orange emitting OLEDs.
  • A compound is disclosed that comprises a ligand LA of Formula I
  • Figure US20240025934A1-20240125-C00004
  • where ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring; each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution; each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; at least one RA has the formula —CH2R or —CHRR′; each RC and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof; LA is complexed to a metal M; M is optionally coordinated to other ligands; the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and any two substituents of RB and RC may be joined or fused together to form a ring.
  • In some embodiments, R and R′ is independently selected from the group consisting of alkyl, cycloalkyl, D variant, F variant, and combinations thereof.
  • In some embodiments of the compound, each RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of the preferred general substituents defined above.
  • In some embodiments, M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au. In some embodiments, M is Ir or Pt. In some embodiments, M is Ir(III) or Pt(II).
  • In some embodiments, R is selected from the group consisting of alkyl, cycloalkyl, partially fluorinated variants thereof, partially or fully deuterated variants thereof, and combination thereof.
  • In some embodiments, the compound comprises a substituted or unsubstituted acetylacetone ligand.
  • In some embodiments, at least one RB comprises a cyclohexyl or tert-butyl group.
  • In some embodiments, ring C is selected from the group consisting of benzene, pyridine, pyrimidine, pyrazine, and pyridazine. In some embodiments, ring C is a furan or thiofuran ring.
  • In some embodiments of the compound, the ligand LA is selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00005
    Figure US20240025934A1-20240125-C00006
  • In some embodiments of the compound, the ligand LA is selected from the group consisting of: LA1 through LA448 based on the structure of Formula II
  • Figure US20240025934A1-20240125-C00007
  • in which R1, R2, and G are defined as:
  • Ligand R1 R2 G
    LA1 RB3 H RC2
    LA2 RB4 H RC2
    LA3 RB5 H RC2
    LA4 RB18 H RC2
    LA5 RB43 H RC2
    LA6 RA3 H RC2
    LA7 RA34 H RC2
    LA8 RA57 H RC2
    LA9 RB3 F RC2
    LA10 RB4 F RC2
    LA11 RB5 F RC2
    LA12 RB18 F RC2
    LA13 RB43 F RC2
    LA14 RA3 F RC2
    LA15 RA34 F RC2
    LA16 RA57 F RC2
    LA17 RB3 RB1 RC2
    LA18 RB4 RB1 RC2
    LA10 RB5 RB1 RC2
    LA20 RB18 RB1 RC2
    LA21 RB43 RB1 RC2
    LA22 RA3 RB1 RC2
    LA23 RA34 RB1 RC2
    LA24 RA57 RB1 RC2
    LA25 RB3 RA74 RC2
    LA26 RB4 RA74 RC2
    LA27 RB5 RA74 RC2
    LA28 RB18 RA74 RC2
    LA29 RB43 RA74 RC2
    LA30 RA3 RA74 RC2
    LA31 RA34 RA74 RC2
    LA32 RA57 RA74 RC2
    LA33 RB3 H RC5
    LA34 RB4 H RC5
    LA35 RB5 H RC5
    LA36 RB18 H RC5
    LA37 RB43 H RC5
    LA38 RA3 H RC5
    LA39 RA34 H RC5
    LA40 RA57 H RC5
    LA41 RB3 F RC5
    LA42 RB4 F RC5
    LA43 RB5 F RC5
    LA44 RB18 F RC5
    LA45 RB43 F RC5
    LA46 RA3 F RC5
    LA47 RA34 F RC5
    LA48 RA57 F RC5
    LA49 RB3 RB1 RC5
    LA50 RB4 RB1 RC5
    LA51 RB5 RB1 RC5
    LA52 RB18 RB1 RC5
    LA53 RB43 RB1 RC5
    LA54 RA3 RB1 RC5
    LA55 RA34 RB1 RC5
    LA56 RA57 RB1 RC5
    LA57 RB3 RA74 RC5
    LA58 RB4 RA74 RC5
    LA59 RB5 RA74 RC5
    LA60 RB18 RA74 RC5
    LA61 RB43 RA74 RC5
    LA62 RA3 RA74 RC5
    LA63 RA34 RA74 RC5
    LA64 RA57 RA74 RC5
    LA65 RB3 H RC6
    LA66 RB4 H RC6
    LA67 RB5 H RC6
    LA68 RB18 H RC6
    LA69 RB43 H RC6
    LA70 RA3 H RC6
    LA71 RA34 H RC6
    LA72 RA57 H RC6
    LA73 RB3 F RC6
    LA74 RB4 F RC6
    LA75 RB5 F RC6
    LA76 RB18 F RC6
    LA77 RB43 F RC6
    LA78 RA3 F RC6
    LA79 RA34 F RC6
    LA80 RA57 F RC6
    LA81 RB3 RB1 RC6
    LA82 RB4 RB1 RC6
    LA83 RB5 RB1 RC6
    LA84 RB18 RB1 RC6
    LA85 RB43 RB1 RC6
    LA86 RA3 RB1 RC6
    LA87 RA34 RB1 RC6
    LA88 RA57 RB1 RC6
    LA89 RB3 RA74 RC6
    LA90 RB4 RA74 RC6
    LA91 RB5 RA74 RC6
    LA92 RB18 RA74 RC6
    LA93 RB43 RA74 RC6
    LA94 RA3 RA74 RC6
    LA95 RA34 RA74 RC6
    LA96 RA57 RA74 RC6
    LA97 RB3 H RC7
    LA98 RB4 H RC7
    LA99 RB5 H RC7
    LA100 RB18 H RC7
    LA101 RB43 H RC7
    LA102 RA3 H RC7
    LA103 RA34 H RC7
    LA104 RA57 H RC7
    LA105 RB3 F RC7
    LA106 RB4 F RC7
    LA107 RB5 F RC7
    LA108 RB18 F RC7
    LA109 RB43 F RC7
    LA110 RA3 F RC7
    LA111 RA34 F RC7
    LA112 RA57 F RC7
    LA113 RB3 RB1 RC7
    LA114 RB4 RB1 RC7
    LA115 RB5 RB1 RC7
    LA116 RB18 RB1 RC7
    LA117 RB43 RB1 RC7
    LA118 RA3 RB1 RC7
    LA119 RA34 RB1 RC7
    LA120 RA57 RB1 RC7
    LA121 RB3 RA74 RC7
    LA122 RB4 RA74 RC7
    LA123 RB5 RA74 RC7
    LA124 RB18 RA74 RC7
    LA125 RB43 RA74 RC7
    LA126 RA3 RA74 RC7
    LA127 RA34 RA74 RC7
    LA128 RA57 RA74 RC7
    LA129 RB3 H RC10
    LA130 RB4 H RC10
    LA131 RB5 H RC10
    LA132 RB18 H RC10
    LA133 RB43 H RC10
    LA134 RA3 H RC10
    LA135 RA34 H RC10
    LA136 RA57 H RC10
    LA137 RB3 F RC10
    LA138 RB4 F RC10
    LA139 RB5 F RC10
    LA140 RB18 F RC10
    LA141 RB43 F RC10
    LA142 RA3 F RC10
    LA143 RA34 F RC10
    LA144 RA57 F RC10
    LA145 RB3 RB1 RC10
    LA146 RB4 RB1 RC10
    LA147 RB5 RB1 RC10
    LA148 RB18 RB1 RC10
    LA149 RB43 RB1 RC10
    LA150 RA3 RB1 RC10
    LA151 RA34 RB1 RC10
    LA152 RA57 RB1 RC10
    LA153 RB3 RA74 RC10
    LA154 RB4 RA74 RC10
    LA155 RB5 RA74 RC10
    LA156 RB18 RA74 RC10
    LA157 RB43 RA74 RC10
    LA158 RA3 RA74 RC10
    LA159 RA34 RA74 RC10
    LA160 RA57 RA74 RC10
    LA161 RB3 H RC11
    LA162 RB4 H RC11
    LA163 RB5 H RC11
    LA164 RB18 H RC11
    LA165 RB43 H RC11
    LA166 RA3 H RC11
    LA167 RA34 H RC11
    LA168 RA57 H RC11
    LA169 RB3 F RC11
    LA170 RB4 F RC11
    LA171 RB5 F RC11
    LA172 RB18 F RC11
    LA173 RB43 F RC11
    LA174 RA3 F RC11
    LA175 RA34 F RC11
    LA176 RA57 F RC11
    LA177 RB3 RB1 RC11
    LA178 RB4 RB1 RC11
    LA179 RB5 RB1 RC11
    LA180 RB18 RB1 RC11
    LA181 RB43 RB1 RC11
    LA182 RA3 RB1 RC11
    LA183 RA34 RB1 RC11
    LA184 RA57 RB1 RC11
    LA185 RB3 RA74 RC11
    LA186 RB4 RA74 RC11
    LA187 RB5 RA74 RC11
    LA188 RB18 RA74 RC11
    LA189 RB43 RA74 RC11
    LA190 RA3 RA74 RC11
    LA191 RA34 RA74 RC11
    LA192 RA57 RA74 RC11
    LA193 RB3 H RC13
    LA194 RB4 H RC13
    LA195 RB5 H RC13
    LA196 RB18 H RC13
    LA197 RB43 H RC13
    LA198 RA3 H RC13
    LA199 RA34 H RC13
    LA200 RA57 H RC13
    LA201 RB3 F RC13
    LA202 RB4 F RC13
    LA203 RB5 F RC13
    LA204 RB18 F RC13
    LA205 RB43 F RC13
    LA206 RA3 F RC13
    LA207 RA34 F RC13
    LA208 RA57 F RC13
    LA209 RB3 RB1 RC13
    LA210 RB4 RB1 RC13
    LA211 RB5 RB1 RC13
    LA212 RB18 RB1 RC13
    LA213 RB43 RB1 RC13
    LA214 RA3 RB1 RC13
    LA215 RA34 RB1 RC13
    LA216 RA57 RB1 RC13
    LA217 RB3 RA74 RC13
    LA218 RB4 RA74 RC13
    LA219 RB5 RA74 RC13
    LA220 RB18 RA74 RC13
    LA221 RB43 RA74 RC13
    LA222 RA3 RA74 RC13
    LA223 RA34 RA74 RC13
    LA224 RA57 RA74 RC13
    LA225 RB3 H RC17
    LA226 RB4 H RC17
    LA227 RB5 H RC17
    LA228 RB18 H RC17
    LA229 RB43 H RC17
    LA230 RA3 H RC17
    LA231 RA34 H RC17
    LA232 RA57 H RC17
    LA233 RB3 F RC17
    LA234 RB4 F RC17
    LA235 RB5 F RC17
    LA236 RB18 F RC17
    LA237 RB43 F RC17
    LA238 RA3 F RC17
    LA239 RA34 F RC17
    LA240 RA57 F RC17
    LA241 RB3 RB1 RC17
    LA242 RB4 RB1 RC17
    LA243 RB5 RB1 RC17
    LA244 RB18 RB1 RC17
    LA245 RB43 RB1 RC17
    LA246 RA3 RB1 RC17
    LA247 RA34 RB1 RC17
    LA248 RA57 RB1 RC17
    LA249 RB3 RA74 RC17
    LA250 RB4 RA74 RC17
    LA251 RB5 RA74 RC17
    LA252 RB18 RA74 RC17
    LA253 RB43 RA74 RC17
    LA254 RA3 RA74 RC17
    LA255 RA34 RA74 RC17
    LA256 RA57 RA74 RC17
    LA257 RB3 H RC20
    LA258 RB4 H RC20
    LA259 RB5 H RC20
    LA260 RB18 H RC20
    LA261 RB43 H RC20
    LA262 RA3 H RC20
    LA263 RA34 H RC20
    LA264 RA57 H RC20
    LA265 RB3 F RC20
    LA266 RB4 F RC20
    LA267 RB5 F RC20
    LA268 RB18 F RC20
    LA269 RB43 F RC20
    LA270 RA3 F RC20
    LA271 RA34 F RC20
    LA272 RA57 F RC20
    LA273 RB3 RB1 RC20
    LA274 RB4 RB1 RC20
    LA275 RB5 RB1 RC20
    LA276 RB18 RB1 RC20
    LA277 RB43 RB1 RC20
    LA278 RA3 RB1 RC20
    LA279 RA34 RB1 RC20
    LA280 RA57 RB1 RC20
    LA281 RB3 RA74 RC20
    LA282 RB4 RA74 RC20
    LA283 RB5 RA74 RC20
    LA284 RB18 RA74 RC20
    LA285 RB43 RA74 RC20
    LA286 RA3 RA74 RC20
    LA287 RA34 RA74 RC20
    LA288 RA57 RA74 RC20
    LA289 RB3 H RC24
    LA290 RB4 H RC24
    LA291 RB5 H RC24
    LA292 RB18 H RC24
    LA293 RB43 H RC24
    LA294 RA3 H RC24
    LA295 RA34 H RC24
    LA296 RA57 H RC24
    LA297 RB3 F RC24
    LA298 RB4 F RC24
    LA299 RB5 F RC24
    LA300 RB18 F RC24
    LA301 RB43 F RC24
    LA302 RA3 F RC24
    LA303 RA34 F RC24
    LA304 RA57 F RC24
    LA305 RB3 RB1 RC24
    LA306 RB4 RB1 RC24
    LA307 RB5 RB1 RC24
    LA308 RB18 RB1 RC24
    LA309 RB43 RB1 RC24
    LA310 RA3 RB1 RC24
    LA311 RA34 RB1 RC24
    LA312 RA57 RB1 RC24
    LA313 RB3 RA74 RC24
    LA314 RB4 RA74 RC24
    LA315 RB5 RA74 RC24
    LA316 RB18 RA74 RC24
    LA317 RB43 RA74 RC24
    LA318 RA3 RA74 RC24
    LA319 RA34 RA74 RC24
    LA320 RA57 RA74 RC24
    LA321 RB3 H RC27
    LA322 RB4 H RC27
    LA323 RB5 H RC27
    LA324 RB18 H RC27
    LA325 RB43 H RC27
    LA326 RA3 H RC27
    LA327 RA34 H RC27
    LA328 RA57 H RC27
    LA329 RB3 F RC27
    LA330 RB4 F RC27
    LA331 RB5 F RC27
    LA332 RB18 F RC27
    LA333 RB43 F RC27
    LA334 RA3 F RC27
    LA335 RA34 F RC27
    LA336 RA57 F RC27
    LA337 RB3 RB1 RC27
    LA338 RB4 RB1 RC27
    LA339 RB5 RB1 RC27
    LA340 RB18 RB1 RC27
    LA341 RB43 RB1 RC27
    LA342 RA3 RB1 RC27
    LA343 RA34 RB1 RC27
    LA344 RA57 RB1 RC27
    LA345 RB3 RA74 RC27
    LA346 RB4 RA74 RC27
    LA347 RB5 RA74 RC27
    LA348 RB18 RA74 RC27
    LA349 RB43 RA74 RC27
    LA350 RA3 RA74 RC27
    LA351 RA34 RA74 RC27
    LA352 RA57 RA74 RC27
    LA353 RB3 H RC31
    LA354 RB4 H RC31
    LA355 RB5 H RC31
    LA356 RB18 H RC31
    LA357 RB43 H RC31
    LA358 RA3 H RC31
    LA359 RA34 H RC31
    LA360 RA57 H RC31
    LA361 RB3 F RC31
    LA362 RB4 F RC31
    LA363 RB5 F RC31
    LA364 RB18 F RC31
    LA365 RB43 F RC31
    LA366 RA3 F RC31
    LA367 RA34 F RC31
    LA368 RA57 F RC31
    LA369 RB3 RB1 RC31
    LA370 RB4 RB1 RC31
    LA371 RB5 RB1 RC31
    LA372 RB18 RB1 RC31
    LA373 RB43 RB1 RC31
    LA374 RA3 RB1 RC31
    LA375 RA34 RB1 RC31
    LA376 RA57 RB1 RC31
    LA377 RB3 RA74 RC31
    LA378 RB4 RA74 RC31
    LA379 RB5 RA74 RC31
    LA380 RB18 RA74 RC31
    LA381 RB43 RA74 RC31
    LA382 RA3 RA74 RC31
    LA383 RA34 RA74 RC31
    LA384 RA57 RA74 RC31
    LA385 RB3 H RC34
    LA386 RB4 H RC34
    LA387 RB5 H RC34
    LA388 RB18 H RC34
    LA389 RB43 H RC34
    LA390 RA3 H RC34
    LA391 RA34 H RC34
    LA392 RA57 H RC34
    LA393 RB3 F RC34
    LA394 RB4 F RC34
    LA395 RB5 F RC34
    LA396 RB18 F RC34
    LA397 RB43 F RC34
    LA398 RA3 F RC34
    LA399 RA34 F RC34
    LA400 RA57 F RC34
    LA401 RB3 RB1 RC34
    LA402 RB4 RB1 RC34
    LA403 RB5 RB1 RC34
    LA404 RB18 RB1 RC34
    LA405 RB43 RB1 RC34
    LA406 RA3 RB1 RC34
    LA407 RA34 RB1 RC34
    LA408 RA57 RB1 RC34
    LA409 RB3 RA74 RC34
    LA410 RB4 RA74 RC34
    LA411 RB5 RA74 RC34
    LA412 RB18 RA74 RC34
    LA413 RB43 RA74 RC34
    LA414 RA3 RA74 RC34
    LA415 RA34 RA74 RC34
    LA416 RA57 RA74 RC34
    LA417 RB3 H RC38
    LA418 RB4 H RC38
    LA419 RB5 H RC38
    LA420 RB18 H RC38
    LA421 RB43 H RC38
    LA422 RA3 H RC38
    LA423 RA34 H RC38
    LA424 RA57 H RC38
    LA425 RB3 F RC38
    LA426 RB4 F RC38
    LA427 RB5 F RC38
    LA428 RB18 F RC38
    LA429 RB43 F RC38
    LA430 RA3 F RC38
    LA431 RA34 F RC38
    LA432 RA57 F RC38
    LA433 RB3 RB1 RC38
    LA434 RB4 RB1 RC38
    LA435 RB5 RB1 RC38
    LA436 RB18 RB1 RC38
    LA437 RB43 RB1 RC38
    LA438 RA3 RB1 RC38
    LA439 RA34 RB1 RC38
    LA440 RA57 RB1 RC38
    LA441 RB3 RA74 RC38
    LA442 RB4 RA74 RC38
    LA443 RB5 RA74 RC38
    LA444 RB18 RA74 RC38
    LA445 RB43 RA74 RC38
    LA446 RA3 RA74 RC38
    LA447 RA34 RA74 RC38
    LA448 RA57 RA74 RC38,

    LA449 through LA896 based on a structure of Formula II
  • Figure US20240025934A1-20240125-C00008
  • in which R1, R2, and G are defined as:
  • Ligand R1 R2 G
    LA449 H RB3 RC2
    LA450 H RB4 RC2
    LA451 H RB5 RC2
    LA452 H RB18 RC2
    LA453 H RB43 RC2
    LA454 H RA3 RC2
    LA455 H RA34 RC2
    LA456 H RA57 RC2
    LA457 F RB3 RC2
    LA458 F RB4 RC2
    LA459 F RB5 RC2
    LA460 F RB18 RC2
    LA461 F RB43 RC2
    LA462 F RA3 RC2
    LA463 F RA34 RC2
    LA464 F RA57 RC2
    LA465 RB1 RB3 RC2
    LA466 RB1 RB4 RC2
    LA467 RB1 RB5 RC2
    LA468 RB1 RB18 RC2
    LA469 RB1 RB43 RC2
    LA470 RB1 RA3 RC2
    LA471 RB1 RA34 RC2
    LA472 RB1 RA57 RC2
    LA473 RA74 RB3 RC2
    LA474 RA74 RB4 RC2
    LA475 RA74 RB5 RC2
    LA476 RA74 RB18 RC2
    LA477 RA74 RB43 RC2
    LA478 RA74 RA3 RC2
    LA479 RA74 RA34 RC2
    LA480 RA74 RA57 RC2
    LA481 H RB3 RC5
    LA482 H RB4 RC5
    LA483 H RB5 RC5
    LA484 H RB18 RC5
    LA485 H RB43 RC5
    LA486 H RA3 RC5
    LA487 H RA34 RC5
    LA488 H RA57 RC5
    LA489 F RB3 RC5
    LA490 F RB4 RC5
    LA491 F RB5 RC5
    LA492 F RB18 RC5
    LA493 F RB43 RC5
    LA494 F RA3 RC5
    LA495 F RA34 RC5
    LA496 F RA57 RC5
    LA497 RB1 RB3 RC5
    LA498 RB1 RB4 RC5
    LA499 RB1 RB5 RC5
    LA500 RB1 RB18 RC5
    LA501 RB1 RB43 RC5
    LA502 RB1 RA3 RC5
    LA503 RB1 RA34 RC5
    LA504 RB1 RA57 RC5
    LA505 RA74 RB3 RC5
    LA506 RA74 RB4 RC5
    LA507 RA74 RB5 RC5
    LA508 RA74 RB18 RC5
    LA509 RA74 RB43 RC5
    LA510 RA74 RA3 RC5
    LA511 RA74 RA34 RC5
    LA512 RA74 RA57 RC5
    LA513 H RB3 RC6
    LA514 H RB4 RC6
    LA515 H RB5 RC6
    LA516 H RB18 RC6
    LA517 H RB43 RC6
    LA518 H RA3 RC6
    LA519 H RA34 RC6
    LA520 H RA57 RC6
    LA521 F RB3 RC6
    LA522 F RB4 RC6
    LA523 F RB5 RC6
    LA524 F RB18 RC6
    LA525 F RB43 RC6
    LA526 F RA3 RC6
    LA527 F RA34 RC6
    LA528 F RA57 RC6
    LA529 RB1 RB3 RC6
    LA530 RB1 RB4 RC6
    LA531 RB1 RB5 RC6
    LA532 RB1 RB18 RC6
    LA533 RB1 RB43 RC6
    LA534 RB1 RA3 RC6
    LA535 RB1 RA34 RC6
    LA536 RB1 RA57 RC6
    LA537 RA74 RB3 RC6
    LA538 RA74 RB4 RC6
    LA539 RA74 RB5 RC6
    LA540 RA74 RB18 RC6
    LA541 RA74 RB43 RC6
    LA542 RA74 RA3 RC6
    LA543 RA74 RA34 RC6
    LA544 RA74 RA57 RC6
    LA545 H RB3 RC7
    LA546 H RB4 RC7
    LA547 H RB5 RC7
    LA548 H RB18 RC7
    LA549 H RB43 RC7
    LA550 H RA3 RC7
    LA551 H RA34 RC7
    LA552 H RA57 RC7
    LA553 F RB3 RC7
    LA554 F RB4 RC7
    LA555 F RB5 RC7
    LA556 F RB18 RC7
    LA557 F RB43 RC7
    LA558 F RA3 RC7
    LA559 F RA34 RC7
    LA560 F RA57 RC7
    LA561 RB1 RB3 RC7
    LA562 RB1 RB4 RC7
    LA563 RB1 RB5 RC7
    LA564 RB1 RB18 RC7
    LA565 RB1 RB43 RC7
    LA566 RB1 RA3 RC7
    LA567 RB1 RA34 RC7
    LA568 RB1 RA57 RC7
    LA569 RA74 RB3 RC7
    LA570 RA74 RB4 RC7
    LA571 RA74 RB5 RC7
    LA572 RA74 RB18 RC7
    LA573 RA74 RB43 RC7
    LA574 RA74 RA3 RC7
    LA575 RA74 RA34 RC7
    LA576 RA74 RA57 RC7
    LA577 H RB3 RC10
    LA578 H RB4 RC10
    LA579 H RB5 RC10
    LA580 H RB18 RC10
    LA581 H RB43 RC10
    LA582 H RA3 RC10
    LA583 H RA34 RC10
    LA584 H RA57 RC10
    LA585 F RB3 RC10
    LA586 F RB4 RC10
    LA587 F RB5 RC10
    LA588 F RB18 RC10
    LA589 F RB43 RC10
    LA590 F RA3 RC10
    LA591 F RA34 RC10
    LA592 F RA57 RC10
    LA593 RB1 RB3 RC10
    LA594 RB1 RB4 RC10
    LA595 RB1 RB5 RC10
    LA596 RB1 RB18 RC10
    LA597 RB1 RB43 RC10
    LA598 RB1 RA3 RC10
    LA599 RB1 RA34 RC10
    LA600 RB1 RA57 RC10
    LA601 RA74 RB3 RC10
    LA602 RA74 RB4 RC10
    LA603 RA74 RB5 RC10
    LA604 RA74 RB18 RC10
    LA605 RA74 RB43 RC10
    LA606 RA74 RA3 RC10
    LA607 RA74 RA34 RC10
    LA608 RA74 RA57 RC10
    LA609 H RB3 RC11
    LA610 H RB4 RC11
    LA611 H RB5 RC11
    LA612 H RB18 RC11
    LA613 H RB43 RC11
    LA614 H RA3 RC11
    LA615 H RA34 RC11
    LA616 H RA57 RC11
    LA617 F RB3 RC11
    LA618 F RB4 RC11
    LA619 F RB5 RC11
    LA620 F RB18 RC11
    LA621 F RB43 RC11
    LA622 F RA3 RC11
    LA623 F RA34 RC11
    LA624 F RA57 RC11
    LA625 RB1 RB3 RC11
    LA626 RB1 RB4 RC11
    LA627 RB1 RB5 RC11
    LA628 RB1 RB18 RC11
    LA629 RB1 RB43 RC11
    LA630 RB1 RA3 RC11
    LA631 RB1 RA34 RC11
    LA632 RB1 RA57 RC11
    LA633 RA74 RB3 RC11
    LA634 RA74 RB4 RC11
    LA635 RA74 RB5 RC11
    LA636 RA74 RB18 RC11
    LA637 RA74 RB43 RC11
    LA638 RA74 RA3 RC11
    LA639 RA74 RA34 RC11
    LA640 RA74 RA57 RC11
    LA641 H RB3 RC13
    LA642 H RB4 RC13
    LA643 H RB5 RC13
    LA644 H RB18 RC13
    LA645 H RB43 RC13
    LA646 H RA3 RC13
    LA647 H RA34 RC13
    LA648 H RA57 RC13
    LA649 F RB3 RC13
    LA650 F RB4 RC13
    LA651 F RB5 RC13
    LA652 F RB18 RC13
    LA653 F RB43 RC13
    LA654 F RA3 RC13
    LA655 F RA34 RC13
    LA656 F RA57 RC13
    LA657 RB1 RB3 RC13
    LA658 RB1 RB4 RC13
    LA659 RB1 RB5 RC13
    LA660 RB1 RB18 RC13
    LA661 RB1 RB43 RC13
    LA662 RB1 RA3 RC13
    LA663 RB1 RA34 RC13
    LA664 RB1 RA57 RC13
    LA665 RA74 RB3 RC13
    LA666 RA74 RB4 RC13
    LA667 RA74 RB5 RC13
    LA668 RA74 RB18 RC13
    LA669 RA74 RB43 RC13
    LA670 RA74 RA3 RC13
    LA671 RA74 RA34 RC13
    LA672 RA74 RA57 RC13
    LA673 H RB3 RC17
    LA674 H RB4 RC17
    LA675 H RB5 RC17
    LA676 H RB18 RC17
    LA677 H RB43 RC17
    LA678 H RA3 RC17
    LA679 H RA34 RC17
    LA680 H RA57 RC17
    LA681 F RB3 RC17
    LA682 F RB4 RC17
    LA683 F RB5 RC17
    LA684 F RB18 RC17
    LA685 F RB43 RC17
    LA686 F RA3 RC17
    LA687 F RA34 RC17
    LA688 F RA57 RC17
    LA689 RB1 RB3 RC17
    LA690 RB1 RB4 RC17
    LA691 RB1 RB5 RC17
    LA692 RB1 RB18 RC17
    LA693 RB1 RB43 RC17
    LA694 RB1 RA3 RC17
    LA695 RB1 RA34 RC17
    LA696 RB1 RA57 RC17
    LA697 RA74 RB3 RC17
    LA698 RA74 RB4 RC17
    LA699 RA74 RB5 RC17
    LA700 RA74 RB18 RC17
    LA701 RA74 RB43 RC17
    LA702 RA74 RA3 RC17
    LA703 RA74 RA34 RC17
    LA704 RA74 RA57 RC17
    LA705 H RB3 RC20
    LA706 H RB4 RC20
    LA707 H RB5 RC20
    LA708 H RB18 RC20
    LA709 H RB43 RC20
    LA710 H RA3 RC20
    LA711 H RA34 RC20
    LA712 H RA57 RC20
    LA713 F RB3 RC20
    LA714 F RB4 RC20
    LA715 F RB5 RC20
    LA716 F RB18 RC20
    LA717 F RB43 RC20
    LA718 F RA3 RC20
    LA719 F RA34 RC20
    LA720 F RA57 RC20
    LA721 RB1 RB3 RC20
    LA722 RB1 RB4 RC20
    LA723 RB1 RB5 RC20
    LA724 RB1 RB18 RC20
    LA725 RB1 RB43 RC20
    LA726 RB1 RA3 RC20
    LA727 RB1 RA34 RC20
    LA728 RB1 RA57 RC20
    LA729 RA74 RB3 RC20
    LA730 RA74 RB4 RC20
    LA731 RA74 RB5 RC20
    LA732 RA74 RB18 RC20
    LA733 RA74 RB43 RC20
    LA734 RA74 RA3 RC20
    LA735 RA74 RA34 RC20
    LA736 RA74 RA57 RC20
    LA737 H RB3 RC24
    LA738 H RB4 RC24
    LA739 H RB5 RC24
    LA740 H RB18 RC24
    LA741 H RB43 RC24
    LA742 H RA3 RC24
    LA743 H RA34 RC24
    LA744 H RA57 RC24
    LA745 F RB3 RC24
    LA746 F RB4 RC24
    LA747 F RB5 RC24
    LA748 F RB18 RC24
    LA749 F RB43 RC24
    LA750 F RA3 RC24
    LA751 F RA34 RC24
    LA752 F RA57 RC24
    LA753 RB1 RB3 RC24
    LA754 RB1 RB4 RC24
    LA755 RB1 RB5 RC24
    LA756 RB1 RB18 RC24
    LA757 RB1 RB43 RC24
    LA758 RB1 RA3 RC24
    LA759 RB1 RA34 RC24
    LA760 RB1 RA57 RC24
    LA761 RA74 RB3 RC24
    LA762 RA74 RB4 RC24
    LA763 RA74 RB5 RC24
    LA764 RA74 RB18 RC24
    LA765 RA74 RB43 RC24
    LA766 RA74 RA3 RC24
    LA767 RA74 RA34 RC24
    LA768 RA74 RA57 RC24
    LA769 H RB3 RC27
    LA770 H RB4 RC27
    LA771 H RB5 RC27
    LA772 H RB18 RC27
    LA773 H RB43 RC27
    LA774 H RA3 RC27
    LA775 H RA34 RC27
    LA776 H RA57 RC27
    LA777 F RB3 RC27
    LA778 F RB4 RC27
    LA779 F RB5 RC27
    LA780 F RB18 RC27
    LA781 F RB43 RC27
    LA782 F RA3 RC27
    LA783 F RA34 RC27
    LA784 F RA57 RC27
    LA785 RB1 RB3 RC27
    LA786 RB1 RB4 RC27
    LA787 RB1 RB5 RC27
    LA788 RB1 RB18 RC27
    LA789 RB1 RB43 RC27
    LA790 RB1 RA3 RC27
    LA791 RB1 RA34 RC27
    LA792 RB1 RA57 RC27
    LA793 RA74 RB3 RC27
    LA794 RA74 RB4 RC27
    LA795 RA74 RB5 RC27
    LA796 RA74 RB18 RC27
    LA797 RA74 RB43 RC27
    LA798 RA74 RA3 RC27
    LA799 RA74 RA34 RC27
    LA800 RA74 RA57 RC27
    LA801 H RB3 RC31
    LA802 H RB4 RC31
    LA803 H RB5 RC31
    LA804 H RB18 RC31
    LA805 H RB43 RC31
    LA806 H RA3 RC31
    LA807 H RA34 RC31
    LA808 H RA57 RC31
    LA809 F RB3 RC31
    LA810 F RB4 RC31
    LA811 F RB5 RC31
    LA812 F RB18 RC31
    LA813 F RB43 RC31
    LA814 F RA3 RC31
    LA815 F RA34 RC31
    LA816 F RA57 RC31
    LA817 RB1 RB3 RC31
    LA818 RB1 RB4 RC31
    LA819 RB1 RB5 RC31
    LA820 RB1 RB18 RC31
    LA821 RB1 RB43 RC31
    LA822 RB1 RA3 RC31
    LA823 RB1 RA34 RC31
    LA824 RB1 RA57 RC31
    LA825 RA74 RB3 RC31
    LA826 RA74 RB4 RC31
    LA827 RA74 RB5 RC31
    LA828 RA74 RB18 RC31
    LA829 RA74 RB43 RC31
    LA830 RA74 RA3 RC31
    LA831 RA74 RA34 RC31
    LA832 RA74 RA57 RC31
    LA833 H RB3 RC34
    LA834 H RB4 RC34
    LA835 H RB5 RC34
    LA836 H RB18 RC34
    LA837 H RB43 RC34
    LA838 H RA3 RC34
    LA839 H RA34 RC34
    LA840 H RA57 RC34
    LA841 F RB3 RC34
    LA842 F RB4 RC34
    LA843 F RB5 RC34
    LA844 F RB18 RC34
    LA845 F RB43 RC34
    LA846 F RA3 RC34
    LA847 F RA34 RC34
    LA848 F RA57 RC34
    LA849 RB1 RB3 RC34
    LA850 RB1 RB4 RC34
    LA851 RB1 RB5 RC34
    LA852 RB1 RB18 RC34
    LA853 RB1 RB43 RC34
    LA854 RB1 RA3 RC34
    LA855 RB1 RA34 RC34
    LA856 RB1 RA57 RC34
    LA857 RA74 RB3 RC34
    LA858 RA74 RB4 RC34
    LA859 RA74 RB5 RC34
    LA860 RA74 RB18 RC34
    LA861 RA74 RB43 RC34
    LA862 RA74 RA3 RC34
    LA863 RA74 RA34 RC34
    LA864 RA74 RA57 RC34
    LA865 H RB3 RC38
    LA866 H RB4 RC38
    LA867 H RB5 RC38
    LA868 H RB18 RC38
    LA869 H RB43 RC38
    LA870 H RA3 RC38
    LA871 H RA34 RC38
    LA872 H RA57 RC38
    LA873 F RB3 RC38
    LA874 F RB4 RC38
    LA875 F RB5 RC38
    LA876 F RB18 RC38
    LA877 F RB43 RC38
    LA878 F RA3 RC38
    LA879 F RA34 RC38
    LA880 F RA57 RC38
    LA881 RB1 RB3 RC38
    LA882 RB1 RB4 RC38
    LA883 RB1 RB5 RC38
    LA884 RB1 RB18 RC38
    LA885 RB1 RB43 RC38
    LA886 RB1 RA3 RC38
    LA887 RB1 RA34 RC38
    LA888 RB1 RA57 RC38
    LA889 RA74 RB3 RC38
    LA890 RA74 RB4 RC38
    LA891 RA74 RB5 RC38
    LA892 RA74 RB18 RC38
    LA893 RA74 RB43 RC38
    LA894 RA74 RA3 RC38
    LA895 RA74 RA34 RC38
    LA896 RA74 RA57 RC38,

    LA897 through LA1344 based on a structure of Formula II
  • Figure US20240025934A1-20240125-C00009
  • in which R1, R2, and G are defined as:
  • Ligand R1 R2 G
    LA897 RB3 RB3 RC2
    LA898 RB4 RB4 RC2
    LA899 RB5 RB5 RC2
    LA900 RB18 RB18 RC2
    LA901 RB43 RB43 RC2
    LA902 RA3 RA3 RC2
    LA903 RA34 RA34 RC2
    LA904 RA57 RA57 RC2
    LA905 RB3 RB7 RC2
    LA906 RB4 RB7 RC2
    LA907 RB5 RB7 RC2
    LA908 RB18 RB7 RC2
    LA909 RB43 RB7 RC2
    LA910 RA3 RB7 RC2
    LA911 RA34 RB7 RC2
    LA912 RA57 RB7 RC2
    LA913 RB3 RA3 RC2
    LA914 RB4 RA3 RC2
    LA915 RB5 RA3 RC2
    LA916 RB18 RA3 RC2
    LA917 RB43 RA3 RC2
    LA918 RA3 RA3 RC2
    LA919 RA34 RA3 RC2
    LA920 RA57 RA3 RC2
    LA921 RB3 RA34 RC2
    LA922 RB4 RA34 RC2
    LA923 RB5 RA34 RC2
    LA924 RB18 RA34 RC2
    LA925 RB43 RA34 RC2
    LA926 RA3 RA34 RC2
    LA927 RA34 RA34 RC2
    LA928 RA57 RA34 RC2
    LA929 RB3 RB3 RC5
    LA930 RB4 RB4 RC5
    LA931 RB5 RB5 RC5
    LA932 RB18 RB18 RC5
    LA933 RB43 RB43 RC5
    LA934 RA3 RA3 RC5
    LA935 RA34 RA34 RC5
    LA936 RA57 RA57 RC5
    LA937 RB3 RB7 RC5
    LA938 RB4 RB7 RC5
    LA939 RB5 RB7 RC5
    LA940 RB18 RB7 RC5
    LA941 RB43 RB7 RC5
    LA942 RA3 RB7 RC5
    LA943 RA34 RB7 RC5
    LA944 RA57 RB7 RC5
    LA945 RB3 RA3 RC5
    LA946 RB4 RA3 RC5
    LA947 RB5 RA3 RC5
    LA948 RB18 RA3 RC5
    LA949 RB43 RA3 RC5
    LA950 RA3 RA3 RC5
    LA951 RA34 RA3 RC5
    LA952 RA57 RA3 RC5
    LA953 RB3 RA34 RC5
    LA954 RB4 RA34 RC5
    LA955 RB5 RA34 RC5
    LA956 RB18 RA34 RC5
    LA957 RB43 RA34 RC5
    LA958 RA3 RA34 RC5
    LA959 RA34 RA34 RC5
    LA960 RA57 RA34 RC5
    LA961 RB3 RB3 RC6
    LA962 RB4 RB4 RC6
    LA963 RB5 RB5 RC6
    LA964 RB18 RB18 RC6
    LA965 RB43 RB43 RC6
    LA966 RA3 RA3 RC6
    LA967 RA34 RA34 RC6
    LA968 RA57 RA57 RC6
    LA969 RB3 RB7 RC6
    LA970 RB4 RB7 RC6
    LA971 RB5 RB7 RC6
    LA972 RB18 RB7 RC6
    LA973 RB43 RB7 RC6
    LA974 RA3 RB7 RC6
    LA975 RA34 RB7 RC6
    LA976 RA57 RB7 RC6
    LA977 RB3 RA3 RC6
    LA978 RB4 RA3 RC6
    LA979 RB5 RA3 RC6
    LA980 RB18 RA3 RC6
    LA981 RB43 RA3 RC6
    LA982 RA3 RA3 RC6
    LA983 RA34 RA3 RC6
    LA984 RA57 RA3 RC6
    LA985 RB3 RA34 RC6
    LA986 RB4 RA34 RC6
    LA987 RB5 RA34 RC6
    LA988 RB18 RA34 RC6
    LA989 RB43 RA34 RC6
    LA990 RA3 RA34 RC6
    LA991 RA34 RA34 RC6
    LA992 RA57 RA34 RC6
    LA993 RB3 RB3 RC7
    LA994 RB4 RB4 RC7
    LA995 RB5 RB5 RC7
    LA996 RB18 RB18 RC7
    LA997 RB43 RB43 RC7
    LA998 RA3 RA3 RC7
    LA999 RA34 RA34 RC7
    LA1000 RA57 RA57 RC7
    LA1001 RB3 RB7 RC7
    LA1002 RB4 RB7 RC7
    LA1003 RB5 RB7 RC7
    LA1004 RB18 RB7 RC7
    LA1005 RB43 RB7 RC7
    LA1006 RA3 RB7 RC7
    LA1007 RA34 RB7 RC7
    LA1008 RA57 RB7 RC7
    LA1009 RB3 RA3 RC7
    LA1010 RB4 RA3 RC7
    LA1011 RB5 RA3 RC7
    LA1012 RB18 RA3 RC7
    LA1013 RB43 RA3 RC7
    LA1014 RA3 RA3 RC7
    LA1015 RA34 RA3 RC7
    LA1016 RA57 RA3 RC7
    LA1017 RB3 RA34 RC7
    LA1018 RB4 RA34 RC7
    LA1019 RB5 RA34 RC7
    LA1020 RB18 RA34 RC7
    LA1021 RB43 RA34 RC7
    LA1022 RA3 RA34 RC7
    LA1023 RA34 RA34 RC7
    LA1024 RA57 RA34 RC7
    LA1025 RB3 RB3 RC10
    LA1026 RB4 RB4 RC10
    LA1027 RB5 RB5 RC10
    LA1028 RB18 RB18 RC10
    LA1029 RB43 RB43 RC10
    LA1030 RA3 RA3 RC10
    LA1031 RA34 RA34 RC10
    LA1032 RA57 RA57 RC10
    LA1033 RB3 RB7 RC10
    LA1034 RB4 RB7 RC10
    LA1035 RB5 RB7 RC10
    LA1036 RB18 RB7 RC10
    LA1037 RB43 RB7 RC10
    LA1038 RA3 RB7 RC10
    LA1039 RA34 RB7 RC10
    LA1040 RA57 RB7 RC10
    LA1041 RB3 RA3 RC10
    LA1042 RB4 RA3 RC10
    LA1043 RB5 RA3 RC10
    LA1044 RB18 RA3 RC10
    LA1045 RB43 RA3 RC10
    LA1046 RA3 RA3 RC10
    LA1047 RA34 RA3 RC10
    LA1048 RA57 RA3 RC10
    LA1049 RB3 RA34 RC10
    LA1050 RB4 RA34 RC10
    LA1051 RB5 RA34 RC10
    LA1052 RB18 RA34 RC10
    LA1053 RB43 RA34 RC10
    LA1054 RA3 RA34 RC10
    LA1055 RA34 RA34 RC10
    LA1056 RA57 RA34 RC10
    LA1057 RB3 RB3 RC11
    LA1058 RB4 RB4 RC11
    LA1059 RB5 RB5 RC11
    LA1060 RB18 RB18 RC11
    LA1061 RB43 RB43 RC11
    LA1062 RA3 RA3 RC11
    LA1063 RA34 RA34 RC11
    LA1064 RA57 RA57 RC11
    LA1065 RB3 RB7 RC11
    LA1066 RB4 RB7 RC11
    LA1067 RB5 RB7 RC11
    LA1068 RB18 RB7 RC11
    LA1069 RB43 RB7 RC11
    LA1070 RA3 RB7 RC11
    LA1071 RA34 RB7 RC11
    LA1072 RA57 RB7 RC11
    LA1073 RB3 RA3 RC11
    LA1074 RB4 RA3 RC11
    LA1075 RB5 RA3 RC11
    LA1076 RB18 RA3 RC11
    LA1077 RB43 RA3 RC11
    LA1078 RA3 RA3 RC11
    LA1079 RA34 RA3 RC11
    LA1080 RA57 RA3 RC11
    LA1081 RB3 RA34 RC11
    LA1082 RB4 RA34 RC11
    LA1083 RB5 RA34 RC11
    LA1084 RB18 RA34 RC11
    LA1085 RB43 RA34 RC11
    LA1086 RA3 RA34 RC11
    LA1087 RA34 RA34 RC11
    LA1088 RA57 RA34 RC11
    LA1089 RB3 RB3 RC13
    LA1090 RB4 RB4 RC13
    LA1091 RB5 RB5 RC13
    LA1092 RB18 RB18 RC13
    LA1093 RB43 RB43 RC13
    LA1094 RA3 RA3 RC13
    LA1095 RA34 RA34 RC13
    LA1096 RA57 RA57 RC13
    LA1097 RB3 RB7 RC13
    LA1098 RB4 RB7 RC13
    LA1099 RB5 RB7 RC13
    LA1100 RB18 RB7 RC13
    LA1101 RB43 RB7 RC13
    LA1102 RA3 RB7 RC13
    LA1103 RA34 RB7 RC13
    LA1104 RA57 RB7 RC13
    LA1105 RB3 RA3 RC13
    LA1106 RB4 RA3 RC13
    LA1107 RB5 RA3 RC13
    LA1108 RB18 RA3 RC13
    LA1109 RB43 RA3 RC13
    LA1110 RA3 RA3 RC13
    LA1111 RA34 RA3 RC13
    LA1112 RA57 RA3 RC13
    LA1113 RB3 RA34 RC13
    LA1114 RB4 RA34 RC13
    LA1115 RB5 RA34 RC13
    LA1116 RB18 RA34 RC13
    LA1117 RB43 RA34 RC13
    LA1118 RA3 RA34 RC13
    LA1119 RA34 RA34 RC13
    LA1120 RA57 RA34 RC13
    LA1121 RB3 RB3 RC17
    LA1122 RB4 RB4 RC17
    LA1123 RB5 RB5 RC17
    LA1124 RB18 RB18 RC17
    LA1125 RB43 RB43 RC17
    LA1126 RA3 RA3 RC17
    LA1127 RA34 RA34 RC17
    LA1128 RA57 RA57 RC17
    LA1129 RB3 RB7 RC17
    LA1130 RB4 RB7 RC17
    LA1131 RB5 RB7 RC17
    LA1132 RB18 RB7 RC17
    LA1133 RB43 RB7 RC17
    LA1134 RA3 RB7 RC17
    LA1135 RA34 RB7 RC17
    LA1136 RA57 RB7 RC17
    LA1137 RB3 RA3 RC17
    LA1138 RB4 RA3 RC17
    LA1139 RB5 RA3 RC17
    LA1140 RB18 RA3 RC17
    LA1141 RB43 RA3 RC17
    LA1142 RA3 RA3 RC17
    LA1143 RA34 RA3 RC17
    LA1144 RA57 RA3 RC17
    LA1145 RB3 RA34 RC17
    LA1146 RB4 RA34 RC17
    LA1147 RB5 RA34 RC17
    LA1148 RB18 RA34 RC17
    LA1149 RB43 RA34 RC17
    LA1150 RA3 RA34 RC17
    LA1151 RA34 RA34 RC17
    LA1152 RA57 RA34 RC17
    LA1153 RB3 RB3 RC20
    LA1154 RB4 RB4 RC20
    LA1155 RB5 RB5 RC20
    LA1156 RB18 RB18 RC20
    LA1157 RB43 RB43 RC20
    LA1158 RA3 RA3 RC20
    LA1159 RA34 RA34 RC20
    LA1160 RA57 RA57 RC20
    LA1161 RB3 RB7 RC20
    LA1162 RB4 RB7 RC20
    LA1163 RB5 RB7 RC20
    LA1164 RB18 RB7 RC20
    LA1165 RB43 RB7 RC20
    LA1166 RA3 RB7 RC20
    LA1167 RA34 RB7 RC20
    LA1168 RA57 RB7 RC20
    LA1169 RB3 RA3 RC20
    LA1170 RB4 RA3 RC20
    LA1171 RB5 RA3 RC20
    LA1172 RB18 RA3 RC20
    LA1173 RB43 RA3 RC20
    LA1174 RA3 RA3 RC20
    LA1175 RA34 RA3 RC20
    LA1176 RA57 RA3 RC20
    LA1177 RB3 RA34 RC20
    LA1178 RB4 RA34 RC20
    LA1179 RB5 RA34 RC20
    LA1180 RB18 RA34 RC20
    LA1181 RB43 RA34 RC20
    LA1182 RA3 RA34 RC20
    LA1183 RA34 RA34 RC20
    LA1184 RA57 RA34 RC20
    LA1185 RB3 RB3 RC24
    LA1186 RB4 RB4 RC24
    LA1187 RB5 RB5 RC24
    LA1188 RB18 RB18 RC24
    LA1189 RB43 RB43 RC24
    LA1190 RA3 RA3 RC24
    LA1191 RA34 RA34 RC24
    LA1192 RA57 RA57 RC24
    LA1193 RB3 RB7 RC24
    LA1194 RB4 RB7 RC24
    LA1195 RB5 RB7 RC24
    LA1196 RB18 RB7 RC24
    LA1197 RB43 RB7 RC24
    LA1198 RA3 RB7 RC24
    LA1199 RA34 RB7 RC24
    LA1200 RA57 RB7 RC24
    LA1201 RB3 RA3 RC24
    LA1202 RB4 RA3 RC24
    LA1203 RB5 RA3 RC24
    LA1204 RB18 RA3 RC24
    LA1205 RB43 RA3 RC24
    LA1206 RA3 RA3 RC24
    LA1207 RA34 RA3 RC24
    LA1208 RA57 RA3 RC24
    LA1209 RB3 RA34 RC24
    LA1210 RB4 RA34 RC24
    LA1211 RB5 RA34 RC24
    LA1212 RB18 RA34 RC24
    LA1213 RB43 RA34 RC24
    LA1214 RA3 RA34 RC24
    LA1215 RA34 RA34 RC24
    LA1216 RA57 RA34 RC24
    LA1217 RB3 RB3 RC27
    LA1218 RB4 RB4 RC27
    LA1219 RB5 RB5 RC27
    LA1220 RB18 RB18 RC27
    LA1221 RB43 RB43 RC27
    LA1222 RA3 RA3 RC27
    LA1223 RA34 RA34 RC27
    LA1224 RA57 RA57 RC27
    LA1225 RB3 RB7 RC27
    LA1226 RB4 RB7 RC27
    LA1227 RB5 RB7 RC27
    LA1228 RB18 RB7 RC27
    LA1229 RB43 RB7 RC27
    LA1230 RA3 RB7 RC27
    LA1231 RA34 RB7 RC27
    LA1232 RA57 RB7 RC27
    LA1233 RB3 RA3 RC27
    LA1234 RB4 RA3 RC27
    LA1235 RB5 RA3 RC27
    LA1236 RB18 RA3 RC27
    LA1237 RB43 RA3 RC27
    LA1238 RA3 RA3 RC27
    LA1239 RA34 RA3 RC27
    LA1240 RA57 RA3 RC27
    LA1241 RB3 RA34 RC27
    LA1242 RB4 RA34 RC27
    LA1243 RB5 RA34 RC27
    LA1244 RB18 RA34 RC27
    LA1245 RB43 RA34 RC27
    LA1246 RA3 RA34 RC27
    LA1247 RA34 RA34 RC27
    LA1248 RA57 RA34 RC27
    LA1249 RB3 RB3 RC31
    LA1250 RB4 RB4 RC31
    LA1251 RB5 RB5 RC31
    LA1252 RB18 RB18 RC31
    LA1253 RB43 RB43 RC31
    LA1254 RA3 RA3 RC31
    LA1255 RA34 RA34 RC31
    LA1256 RA57 RA57 RC31
    LA1257 RB3 RB7 RC31
    LA1258 RB4 RB7 RC31
    LA1259 RB5 RB7 RC31
    LA1260 RB18 RB7 RC31
    LA1261 RB43 RB7 RC31
    LA1262 RA3 RB7 RC31
    LA1263 RA34 RB7 RC31
    LA1264 RA57 RB7 RC31
    LA1265 RB3 RA3 RC31
    LA1266 RB4 RA3 RC31
    LA1267 RB5 RA3 RC31
    LA1268 RB18 RA3 RC31
    LA1269 RB43 RA3 RC31
    LA1270 RA3 RA3 RC31
    LA1271 RA34 RA3 RC31
    LA1272 RA57 RA3 RC31
    LA1273 RB3 RA34 RC31
    LA1274 RB4 RA34 RC31
    LA1275 RB5 RA34 RC31
    LA1276 RB18 RA34 RC31
    LA1277 RB43 RA34 RC31
    LA1278 RA3 RA34 RC31
    LA1279 RA34 RA34 RC31
    LA1280 RA57 RA34 RC31
    LA1281 RB3 RB3 RC34
    LA1282 RB4 RB4 RC34
    LA1283 RB5 RB5 RC34
    LA1284 RB18 RB18 RC34
    LA1285 RB43 RB43 RC34
    LA1286 RA3 RA3 RC34
    LA1287 RA34 RA34 RC34
    LA1288 RA57 RA57 RC34
    LA1289 RB3 RB7 RC34
    LA1290 RB4 RB7 RC34
    LA1291 RB5 RB7 RC34
    LA1292 RB18 RB7 RC34
    LA1293 RB43 RB7 RC34
    LA1294 RA3 RB7 RC34
    LA1295 RA34 RB7 RC34
    LA1296 RA57 RB7 RC34
    LA1297 RB3 RA3 RC34
    LA1298 RB4 RA3 RC34
    LA1299 RB5 RA3 RC34
    LA1300 RB18 RA3 RC34
    LA1301 RB43 RA3 RC34
    LA1302 RA3 RA3 RC34
    LA1303 RA34 RA3 RC34
    LA1304 RA57 RA3 RC34
    LA1305 RB3 RA34 RC34
    LA1306 RB4 RA34 RC34
    LA1307 RB5 RA34 RC34
    LA1308 RB7 RA34 RC34
    LA1309 RB13 RA34 RC34
    LA1310 RA3 RA34 RC34
    LA1311 RA34 RA34 RC34
    LA1312 RA57 RA34 RC34
    LA1313 RB3 RB3 RC38
    LA1314 RB4 RB4 RC38
    LA1315 RB5 RB5 RC38
    LA1316 RB18 RB18 RC38
    LA1317 RB43 RB43 RC38
    LA1318 RA3 RA3 RC38
    LA1319 RA34 RA34 RC38
    LA1320 RA57 RA57 RC38
    LA1321 RB3 RB7 RC38
    LA1322 RB4 RB7 RC38
    LA1323 RB5 RB7 RC38
    LA1324 RB18 RB7 RC38
    LA1325 RB43 RB7 RC38
    LA1326 RA3 RB7 RC38
    LA1327 RA34 RB7 RC38
    LA1328 RA57 RB7 RC38
    LA1329 RB3 RA3 RC38
    LA1330 RB4 RA3 RC38
    LA1331 RB5 RA3 RC38
    LA1332 RB18 RA3 RC38
    LA1333 RB43 RA3 RC38
    LA1334 RA3 RA3 RC38
    LA1335 RA34 RA3 RC38
    LA1336 RA57 RA3 RC38
    LA1337 RB3 RA34 RC38
    LA1338 RB4 RA34 RC38
    LA1339 RB5 RA34 RC38
    LA1340 RB18 RA34 RC38
    LA1341 RB43 RA34 RC38
    LA1342 RA3 RA34 RC38
    LA1343 RA34 RA34 RC38
    LA1344 RA57 RA34 RC38,

    LA1345 through LA1792 based on a structure of Formula II
  • Figure US20240025934A1-20240125-C00010
  • in which R1, R2, and G are defined as:
  • Ligand R1 R2 G
    LA1345 RB13 RB3 RC2
    LA1346 RB13 RB4 RC2
    LA1347 RB13 RB5 RC2
    LA1348 RB13 RB18 RC2
    LA1349 RB13 RB43 RC2
    LA1350 RB13 RA3 RC2
    LA1351 RB13 RA34 RC2
    LA1352 RB13 RA57 RC2
    LA1353 RB7 RB3 RC2
    LA1354 RB7 RB4 RC2
    LA1355 RB7 RB5 RC2
    LA1356 RB7 RB18 RC2
    LA1357 RB7 RB43 RC2
    LA1358 RB7 RA3 RC2
    LA1359 RB7 RA34 RC2
    LA1360 RB7 RA57 RC2
    LA1361 RA3 RB3 RC2
    LA1362 RA3 RB4 RC2
    LA1363 RA3 RB5 RC2
    LA1364 RA3 RB18 RC2
    LA1365 RA3 RB43 RC2
    LA1366 RA3 RA3 RC2
    LA1367 RA3 RA34 RC2
    LA1368 RA3 RA57 RC2
    LA1369 RA34 RB3 RC2
    LA1370 RA34 RB4 RC2
    LA1371 RA34 RB5 RC2
    LA1372 RA34 RB18 RC2
    LA1373 RA34 RB43 RC2
    LA1374 RA34 RA3 RC2
    LA1375 RA34 RA34 RC2
    LA1376 RA34 RA57 RC2
    LA1377 RB13 RB3 RC5
    LA1378 RB13 RB4 RC5
    LA1379 RB13 RB5 RC5
    LA1380 RB13 RB18 RC5
    LA1381 RB13 RB43 RC5
    LA1382 RB13 RA3 RC5
    LA1383 RB13 RA34 RC5
    LA1384 RB13 RA57 RC5
    LA1385 RB7 RB3 RC5
    LA1386 RB7 RB4 RC5
    LA1387 RB7 RB5 RC5
    LA1388 RB7 RB18 RC5
    LA1389 RB7 RB43 RC5
    LA1390 RB7 RA3 RC5
    LA1391 RB7 RA34 RC5
    LA1392 RB7 RA57 RC5
    LA1393 RA3 RB3 RC5
    LA1394 RA3 RB4 RC5
    LA1395 RA3 RB5 RC5
    LA1396 RA3 RB18 RC5
    LA1397 RA3 RB43 RC5
    LA1398 RA3 RA3 RC5
    LA1399 RA3 RA34 RC5
    LA1400 RA3 RA57 RC5
    LA1401 RA34 RB3 RC5
    LA1402 RA34 RB4 RC5
    LA1403 RA34 RB5 RC5
    LA1404 RA34 RB18 RC5
    LA1405 RA34 RB43 RC5
    LA1406 RA34 RA3 RC5
    LA1407 RA34 RA34 RC5
    LA1408 RA34 RA57 RC5
    LA1409 RB13 RB3 RC6
    LA1410 RB13 RB4 RC6
    LA1411 RB13 RB5 RC6
    LA1412 RB13 RB18 RC6
    LA1413 RB13 RB43 RC6
    LA1414 RB13 RA3 RC6
    LA1415 RB13 RA34 RC6
    LA1416 RB13 RA57 RC6
    LA1417 RB7 RB3 RC6
    LA1418 RB7 RB4 RC6
    LA1419 RB7 RB5 RC6
    LA1420 RB7 RB18 RC6
    LA1421 RB7 RB43 RC6
    LA1422 RB7 RA3 RC6
    LA1423 RB7 RA34 RC6
    LA1424 RB7 RA57 RC6
    LA1425 RA3 RB3 RC6
    LA1426 RA3 RB4 RC6
    LA1427 RA3 RB5 RC6
    LA1428 RA3 RB18 RC6
    LA1429 RA3 RB43 RC6
    LA1430 RA3 RA3 RC6
    LA1431 RA3 RA34 RC6
    LA1432 RA3 RA57 RC6
    LA1433 RA34 RB3 RC6
    LA1434 RA34 RB4 RC6
    LA1435 RA34 RB5 RC6
    LA1436 RA34 RB18 RC6
    LA1437 RA34 RB43 RC6
    LA1438 RA34 RA3 RC6
    LA1439 RA34 RA34 RC6
    LA1440 RA34 RA57 RC6
    LA1441 RB13 RB3 RC7
    LA1442 RB13 RB4 RC7
    LA1443 RB13 RB5 RC7
    LA1444 RB13 RB18 RC7
    LA1445 RB13 RB43 RC7
    LA1446 RB13 RA3 RC7
    LA1447 RB13 RA34 RC7
    LA1448 RB13 RA57 RC7
    LA1449 RB7 RB3 RC7
    LA1450 RB7 RB4 RC7
    LA1451 RB7 RB5 RC7
    LA1452 RB7 RB18 RC7
    LA1453 RB7 RB43 RC7
    LA1454 RB7 RA3 RC7
    LA1455 RB7 RA34 RC7
    LA1456 RB7 RA57 RC7
    LA1457 RA3 RB3 RC7
    LA1458 RA3 RB4 RC7
    LA1459 RA3 RB5 RC7
    LA1460 RA3 RB18 RC7
    LA1461 RA3 RB43 RC7
    LA1462 RA3 RA3 RC7
    LA1463 RA3 RA34 RC7
    LA1464 RA3 RA57 RC7
    LA1465 RA34 RB3 RC7
    LA1466 RA34 RB4 RC7
    LA1467 RA34 RB5 RC7
    LA1468 RA34 RB18 RC7
    LA1469 RA34 RB43 RC7
    LA1470 RA34 RA3 RC7
    LA1471 RA34 RA34 RC7
    LA1472 RA34 RA57 RC7
    LA1473 RB13 RB3 RC10
    LA1474 RB13 RB4 RC10
    LA1475 RB13 RB5 RC10
    LA1476 RB13 RB18 RC10
    LA1477 RB13 RB43 RC10
    LA1478 RB13 RA3 RC10
    LA1479 RB13 RA34 RC10
    LA1480 RB13 RA57 RC10
    LA1481 RB7 RB3 RC10
    LA1482 RB7 RB4 RC10
    LA1483 RB7 RB5 RC10
    LA1484 RB7 RB18 RC10
    LA1485 RB7 RB43 RC10
    LA1486 RB7 RA3 RC10
    LA1487 RB7 RA34 RC10
    LA1488 RB7 RA57 RC10
    LA1489 RA3 RB3 RC10
    LA1490 RA3 RB4 RC10
    LA1491 RA3 RB5 RC10
    LA1492 RA3 RB18 RC10
    LA1493 RA3 RB43 RC10
    LA1494 RA3 RA3 RC10
    LA1495 RA3 RA34 RC10
    LA1496 RA3 RA57 RC10
    LA1497 RA34 RB3 RC10
    LA1498 RA34 RB4 RC10
    LA1499 RA34 RB5 RC10
    LA1500 RA34 RB18 RC10
    LA1501 RA34 RB43 RC10
    LA1502 RA34 RA3 RC10
    LA1503 RA34 RA34 RC10
    LA1504 RA34 RA57 RC10
    LA1505 RB13 RB3 RC11
    LA1506 RB13 RB4 RC11
    LA1507 RB13 RB5 RC11
    LA1508 RB13 RB18 RC11
    LA1509 RB13 RB43 RC11
    LA1510 RB13 RA3 RC11
    LA1511 RB3 RA34 RC11
    LA1512 RB13 RA57 RC11
    LA1513 RB7 RB3 RC11
    LA1514 RB7 RB4 RC11
    LA1515 RB7 RB5 RC11
    LA1516 RB7 RB18 RC11
    LA1517 RB7 RB43 RC11
    LA1518 RB7 RA3 RC11
    LA1519 RB7 RA34 RC11
    LA1520 RB7 RA57 RC11
    LA1521 RA3 RB3 RC11
    LA1522 RA3 RB4 RC11
    LA1523 RA3 RB5 RC11
    LA1524 RA3 RB18 RC11
    LA1525 RA3 RB43 RC11
    LA1526 RA3 RA3 RC11
    LA1527 RA3 RA34 RC11
    LA1528 RA3 RA57 RC11
    LA1529 RA34 RB3 RC11
    LA1530 RA34 RB4 RC11
    LA1531 RA34 RB5 RC11
    LA1532 RA34 RB18 RC11
    LA1533 RA34 RB43 RC11
    LA1534 RA34 RA3 RC11
    LA1535 RA34 RA34 RC11
    LA1536 RA34 RA57 RC11
    LA1537 RB13 RB3 RC13
    LA1538 RB13 RB4 RC13
    LA1539 RB13 RB5 RC13
    LA1540 RB13 RB18 RC13
    LA1541 RB13 RB43 RC13
    LA1542 RB13 RA3 RC13
    LA1543 RB13 RA34 RC13
    LA1544 RB13 RA57 RC13
    LA1545 RB7 RB3 RC13
    LA1546 RB7 RB4 RC13
    LA1547 RB7 RB5 RC13
    LA1548 RB7 RB18 RC13
    LA1549 RB7 RB43 RC13
    LA1550 RB7 RA3 RC13
    LA1551 RB7 RA34 RC13
    LA1552 RB7 RA57 RC13
    LA1553 RA3 RB3 RC13
    LA1554 RA3 RB4 RC13
    LA1555 RA3 RB5 RC13
    LA1556 RA3 RB18 RC13
    LA1557 RA3 RB43 RC13
    LA1558 RA3 RA3 RC13
    LA1559 RA3 RA34 RC13
    LA1560 RA3 RA57 RC13
    LA1561 RA34 RB3 RC13
    LA1562 RA34 RB4 RC13
    LA1563 RA34 RB5 RC13
    LA1564 RA34 RB18 RC13
    LA1565 RA34 RB43 RC13
    LA1566 RA34 RA3 RC13
    LA1567 RA34 RA34 RC13
    LA1568 RA34 RA57 RC13
    LA1569 RB13 RB3 RC17
    LA1570 RB13 RB4 RC17
    LA1571 RB13 RB5 RC17
    LA1572 RB13 RB18 RC17
    LA1573 RB13 RB43 RC17
    LA1574 RB13 RA3 RC17
    LA1575 RB13 RA34 RC17
    LA1576 RB13 RA57 RC17
    LA1577 RB7 RB3 RC17
    LA1578 RB7 RB4 RC17
    LA1579 RB7 RB5 RC17
    LA1580 RB7 RB18 RC17
    LA1581 RB7 RB43 RC17
    LA1582 RB7 RA3 RC17
    LA1583 RB7 RA34 RC17
    LA1584 RB7 RA57 RC17
    LA1585 RA3 RB3 RC17
    LA1586 RA3 RB4 RC17
    LA1587 RA3 RB5 RC17
    LA1588 RA3 RB18 RC17
    LA1589 RA3 RB43 RC17
    LA1590 RA3 RA3 RC17
    LA1591 RA3 RA34 RC17
    LA1592 RA3 RA57 RC17
    LA1593 RA34 RB3 RC17
    LA1594 RA34 RB4 RC17
    LA1595 RA34 RB5 RC17
    LA1596 RA34 RB18 RC17
    LA1597 RA34 RB43 RC17
    LA1598 RA34 RA3 RC17
    LA1599 RA34 RA34 RC17
    LA1600 RA34 RA57 RC17
    LA1601 RB13 RB3 RC20
    LA1602 RB13 RB4 RC20
    LA1603 RB13 RB5 RC20
    LA1604 RB13 RB18 RC20
    LA1605 RB13 RB43 RC20
    LA1606 RB13 RA3 RC20
    LA1607 RB13 RA34 RC20
    LA1608 RB13 RA57 RC20
    LA1609 RB7 RB3 RC20
    LA1610 RB7 RB4 RC20
    LA1611 RB7 RB5 RC20
    LA1612 RB7 RB18 RC20
    LA1613 RB7 RB43 RC20
    LA1614 RB7 RA3 RC20
    LA1615 RB7 RA34 RC20
    LA1616 RB7 RA57 RC20
    LA1617 RA3 RB3 RC20
    LA1618 RA3 RB4 RC20
    LA1619 RA3 RB5 RC20
    LA1620 RA3 RB18 RC20
    LA1621 RA3 RB43 RC20
    LA1622 RA3 RA3 RC20
    LA1623 RA3 RA34 RC20
    LA1624 RA3 RA57 RC20
    LA1625 RA34 RB3 RC20
    LA1626 RA34 RB4 RC20
    LA1627 RA34 RB5 RC20
    LA1628 RA34 RB18 RC20
    LA1629 RA34 RB43 RC20
    LA1630 RA34 RA3 RC20
    LA1631 RA34 RA34 RC20
    LA1632 RA34 RA57 RC20
    LA1633 RB13 RB3 RC24
    LA1634 RB13 RB4 RC24
    LA1635 RB13 RB5 RC24
    LA1636 RB13 RB18 RC24
    LA1637 RB13 RB43 RC24
    LA1638 RB13 RA3 RC24
    LA1639 RB13 RA34 RC24
    LA1640 RB13 RA57 RC24
    LA1641 RB7 RB3 RC24
    LA1642 RB7 RB4 RC24
    LA1643 RB7 RB5 RC24
    LA1644 RB7 RB18 RC24
    LA1645 RB7 RB43 RC24
    LA1646 RB7 RA3 RC24
    LA1647 RB7 RA34 RC24
    LA1648 RB7 RA57 RC24
    LA1649 RA3 RB3 RC24
    LA1650 RA3 RB4 RC24
    LA1651 RA3 RB5 RC24
    LA1652 RA3 RB18 RC24
    LA1653 RA3 RB43 RC24
    LA1654 RA3 RA3 RC24
    LA1655 RA3 RA34 RC24
    LA1656 RA3 RA57 RC24
    LA1657 RA34 RB3 RC24
    LA1658 RA34 RB4 RC24
    LA1659 RA34 RB5 RC24
    LA1660 RA34 RB18 RC24
    LA1661 RA34 RB43 RC24
    LA1662 RA34 RA3 RC24
    LA1663 RA34 RA34 RC24
    LA1664 RA34 RA57 RC24
    LA1665 RB13 RB3 RC27
    LA1666 RB13 RB4 RC27
    LA1667 RB13 RB5 RC27
    LA1668 RB13 RB18 RC27
    LA1669 RB13 RB43 RC27
    LA1670 RB13 RA3 RC27
    LA1671 RB13 RA34 RC27
    LA1672 RB13 RA57 RC27
    LA1673 RB7 RB3 RC27
    LA1674 RB7 RB4 RC27
    LA1675 RB7 RB5 RC27
    LA1676 RB7 RB18 RC27
    LA1677 RB7 RB43 RC27
    LA1678 RB7 RA3 RC27
    LA1679 RB7 RA34 RC27
    LA1680 RB7 RA57 RC27
    LA1681 RA3 RB3 RC27
    LA1682 RA3 RB4 RC27
    LA1683 RA3 RB5 RC27
    LA1684 RA3 RB18 RC27
    LA1685 RA3 RB43 RC27
    LA1686 RA3 RA3 RC27
    LA1687 RA3 RA34 RC27
    LA1688 RA3 RA57 RC27
    LA1689 RA34 RB3 RC27
    LA1690 RA34 RB4 RC27
    LA1691 RA34 RB5 RC27
    LA1692 RA34 RB18 RC27
    LA1693 RA34 RB43 RC27
    LA1694 RA34 RA3 RC27
    LA1695 RA34 RA34 RC27
    LA1696 RA34 RA57 RC27
    LA1697 RB13 RB3 RC31
    LA1698 RB13 RB4 RC31
    LA1699 RB13 RB5 RC31
    LA1700 RB13 RB18 RC31
    LA1701 RB13 RB43 RC31
    LA1702 RB13 RA3 RC31
    LA1703 RB13 RA34 RC31
    LA1704 RB13 RA57 RC31
    LA1705 RB7 RB3 RC31
    LA1706 RB7 RB4 RC31
    LA1707 RB7 RB5 RC31
    LA1708 RB7 RB18 RC31
    LA1709 RB7 RB43 RC31
    LA1710 RB7 RA3 RC31
    LA1711 RB7 RA34 RC31
    LA1712 RB7 RA57 RC31
    LA1713 RA3 RB3 RC31
    LA1714 RA3 RB4 RC31
    LA1715 RA3 RB5 RC31
    LA1716 RA3 RB18 RC31
    LA1717 RA3 RB43 RC31
    LA1718 RA3 RA3 RC31
    LA1719 RA3 RA34 RC31
    LA1720 RA3 RA57 RC31
    LA1721 RA34 RB3 RC31
    LA1722 RA34 RB4 RC31
    LA1723 RA34 RB5 RC31
    LA1724 RA34 RB18 RC31
    LA1725 RA34 RB43 RC31
    LA1726 RA34 RA3 RC31
    LA1727 RA34 RA34 RC31
    LA1728 RA34 RA57 RC31
    LA1729 RB13 RB3 RC34
    LA1730 RB13 RB4 RC34
    LA1731 RB13 RB5 RC34
    LA1732 RB13 RB18 RC34
    LA1733 RB13 RB43 RC34
    LA1734 RB13 RA3 RC34
    LA1735 RB13 RA34 RC34
    LA1736 RB13 RA57 RC34
    LA1737 RB7 RB3 RC34
    LA1738 RB7 RB4 RC34
    LA1739 RB7 RB5 RC34
    LA1740 RB7 RB18 RC34
    LA1741 RB7 RB43 RC34
    LA1742 RB7 RA3 RC34
    LA1743 RB7 RA34 RC34
    LA1744 RB7 RA57 RC34
    LA1745 RA3 RB3 RC34
    LA1746 RA3 RB4 RC34
    LA1747 RA3 RB5 RC34
    LA1748 RA3 RB18 RC34
    LA1749 RA3 RB43 RC34
    LA1750 RA3 RA3 RC34
    LA1751 RA3 RA34 RC34
    LA1752 RA3 RA57 RC34
    LA1753 RA34 RB3 RC34
    LA1754 RA34 RB4 RC34
    LA1755 RA34 RB5 RC34
    LA1756 RA34 RB7 RC34
    LA1757 RA34 RB13 RC34
    LA1758 RA34 RA3 RC34
    LA1759 RA34 RA34 RC34
    LA1760 RA34 RA57 RC34
    LA1761 RB13 RB3 RC38
    LA1762 RB13 RB4 RC38
    LA1763 RB13 RB5 RC38
    LA1764 RB3 RB18 RC38
    LA1765 RB13 RB43 RC38
    LA1766 RB13 RA3 RC38
    LA1767 RB13 RA34 RC38
    LA1768 RB13 RA57 RC38
    LA1769 RB7 RB3 RC38
    LA1770 RB7 RB4 RC38
    LA1771 RB7 RB5 RC38
    LA1772 RB7 RB18 RC38
    LA1773 RB7 RB43 RC38
    LA1774 RB7 RA3 RC38
    LA1775 RB7 RA34 RC38
    LA1776 RB7 RA57 RC38
    LA1777 RA3 RB3 RC38
    LA1778 RA3 RB4 RC38
    LA1779 RA3 RB5 RC38
    LA1780 RA3 RB18 RC38
    LA1781 RA3 RB43 RC38
    LA1782 RA3 RA3 RC38
    LA1783 RA3 RA34 RC38
    LA1784 RA3 RA57 RC38
    LA1785 RA34 RB3 RC38
    LA1786 RA34 RB4 RC38
    LA1787 RA34 RB5 RC38
    LA1788 RA34 RB18 RC38
    LA1789 RA34 RB43 RC38
    LA1790 RA34 RA3 RC38
    LA1791 RA34 RA34 RC38
    LA1792 RA34 RA57 RC38,

    wherein RA1 to RA74 have the following structures:
  • Figure US20240025934A1-20240125-C00011
    Figure US20240025934A1-20240125-C00012
    Figure US20240025934A1-20240125-C00013
    Figure US20240025934A1-20240125-C00014
    Figure US20240025934A1-20240125-C00015
    Figure US20240025934A1-20240125-C00016
  • wherein RB1 to RB42 have the following structures:
  • Figure US20240025934A1-20240125-C00017
    Figure US20240025934A1-20240125-C00018
    Figure US20240025934A1-20240125-C00019
    Figure US20240025934A1-20240125-C00020
    Figure US20240025934A1-20240125-C00021
      • wherein RC1 to RC42 have the following structures:
  • Figure US20240025934A1-20240125-C00022
    Figure US20240025934A1-20240125-C00023
    Figure US20240025934A1-20240125-C00024
    Figure US20240025934A1-20240125-C00025
    Figure US20240025934A1-20240125-C00026
    Figure US20240025934A1-20240125-C00027
    Figure US20240025934A1-20240125-C00028
  • In some embodiments, the compound has a formula of M(LA)x(LB)y(LC)z, wherein LA is selected from the group consisting of LA1 to LA179, and LB and LC are each a bidentate ligand; and x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M. 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), wherein LA, LB, and LC are as defined above; and wherein LA, LB, and LC are different from each other. In some embodiments, the compound has a formula of Pt(LA)(LB); wherein LA, LB, and LC are as defined above, and wherein LA and LB can be same or different. In some embodiments of the compound having the formula Pt(LA)(LB), the LA and LB are connected to form a tetradentate ligand.
  • In some embodiments, the compound having the formula of M(LA)x(LB)y(LC)z defined above, LB and LC are each independently selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00029
    Figure US20240025934A1-20240125-C00030
    Figure US20240025934A1-20240125-C00031
  • where each Y1 to Y3 are independently selected from the group consisting of carbon and nitrogen; Y′ is selected from the group consisting of B Re, N Re, P Re, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf, Re and Rf are optionally fused or joined to form a ring; each Ra, Rb, Rc and Rd may independently represent from mono substitution to the maximum possible number of substitutions, or no substitution; each Ra, Rb, Rc, Rd, Re, and Rf is independently a hydrogen or a substituent selected from the group consisting of the general substituents defined above; and any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
  • In some embodiments, the compound having the formula of M(LA)x(LB)y(LC)z defined above, LB and LC are each independently selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00032
    Figure US20240025934A1-20240125-C00033
    Figure US20240025934A1-20240125-C00034
  • In some embodiments of the compound having 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, the compound is Compound Ax having the formula Ir(LA)3, the Compound By having the formula Ir(LA)(LB)2, or the Compound Cz having the formula Ir(LA)2(LC);
      • where LA is selected from the group consisting of LAi, where i is an integer from 1 to 1792;
      • where LB is selected from the group consisting of LBk, where k is an integer from 1 to 468;
      • where LC is selected from the group consisting of LCj, where j is an integer from 1 to 1260;
      • where x=i, y=468i+k−468, and z=1260i+j−1260;
      • where each LBk has the following structure:
  • Figure US20240025934A1-20240125-C00035
    Figure US20240025934A1-20240125-C00036
    Figure US20240025934A1-20240125-C00037
    Figure US20240025934A1-20240125-C00038
    Figure US20240025934A1-20240125-C00039
    Figure US20240025934A1-20240125-C00040
    Figure US20240025934A1-20240125-C00041
    Figure US20240025934A1-20240125-C00042
    Figure US20240025934A1-20240125-C00043
    Figure US20240025934A1-20240125-C00044
    Figure US20240025934A1-20240125-C00045
    Figure US20240025934A1-20240125-C00046
    Figure US20240025934A1-20240125-C00047
    Figure US20240025934A1-20240125-C00048
    Figure US20240025934A1-20240125-C00049
    Figure US20240025934A1-20240125-C00050
    Figure US20240025934A1-20240125-C00051
    Figure US20240025934A1-20240125-C00052
    Figure US20240025934A1-20240125-C00053
    Figure US20240025934A1-20240125-C00054
    Figure US20240025934A1-20240125-C00055
    Figure US20240025934A1-20240125-C00056
    Figure US20240025934A1-20240125-C00057
    Figure US20240025934A1-20240125-C00058
    Figure US20240025934A1-20240125-C00059
    Figure US20240025934A1-20240125-C00060
    Figure US20240025934A1-20240125-C00061
  • Figure US20240025934A1-20240125-C00062
    Figure US20240025934A1-20240125-C00063
    Figure US20240025934A1-20240125-C00064
    Figure US20240025934A1-20240125-C00065
    Figure US20240025934A1-20240125-C00066
    Figure US20240025934A1-20240125-C00067
    Figure US20240025934A1-20240125-C00068
    Figure US20240025934A1-20240125-C00069
    Figure US20240025934A1-20240125-C00070
    Figure US20240025934A1-20240125-C00071
    Figure US20240025934A1-20240125-C00072
    Figure US20240025934A1-20240125-C00073
    Figure US20240025934A1-20240125-C00074
    Figure US20240025934A1-20240125-C00075
    Figure US20240025934A1-20240125-C00076
    Figure US20240025934A1-20240125-C00077
    Figure US20240025934A1-20240125-C00078
    Figure US20240025934A1-20240125-C00079
    Figure US20240025934A1-20240125-C00080
    Figure US20240025934A1-20240125-C00081
    Figure US20240025934A1-20240125-C00082
    Figure US20240025934A1-20240125-C00083
    Figure US20240025934A1-20240125-C00084
    Figure US20240025934A1-20240125-C00085
    Figure US20240025934A1-20240125-C00086
    Figure US20240025934A1-20240125-C00087
    Figure US20240025934A1-20240125-C00088
    Figure US20240025934A1-20240125-C00089
    Figure US20240025934A1-20240125-C00090
    Figure US20240025934A1-20240125-C00091
    Figure US20240025934A1-20240125-C00092
    Figure US20240025934A1-20240125-C00093
    Figure US20240025934A1-20240125-C00094
    Figure US20240025934A1-20240125-C00095
    Figure US20240025934A1-20240125-C00096
    Figure US20240025934A1-20240125-C00097
  • Figure US20240025934A1-20240125-C00098
    Figure US20240025934A1-20240125-C00099
    Figure US20240025934A1-20240125-C00100
    Figure US20240025934A1-20240125-C00101
    Figure US20240025934A1-20240125-C00102
    Figure US20240025934A1-20240125-C00103
    Figure US20240025934A1-20240125-C00104
    Figure US20240025934A1-20240125-C00105
    Figure US20240025934A1-20240125-C00106
    Figure US20240025934A1-20240125-C00107
    Figure US20240025934A1-20240125-C00108
    Figure US20240025934A1-20240125-C00109
    Figure US20240025934A1-20240125-C00110
    Figure US20240025934A1-20240125-C00111
    Figure US20240025934A1-20240125-C00112
    Figure US20240025934A1-20240125-C00113
    Figure US20240025934A1-20240125-C00114
    Figure US20240025934A1-20240125-C00115
    Figure US20240025934A1-20240125-C00116
    Figure US20240025934A1-20240125-C00117
    Figure US20240025934A1-20240125-C00118
    Figure US20240025934A1-20240125-C00119
    Figure US20240025934A1-20240125-C00120
    Figure US20240025934A1-20240125-C00121
    Figure US20240025934A1-20240125-C00122
    Figure US20240025934A1-20240125-C00123
    Figure US20240025934A1-20240125-C00124
    Figure US20240025934A1-20240125-C00125
    Figure US20240025934A1-20240125-C00126
    Figure US20240025934A1-20240125-C00127
    Figure US20240025934A1-20240125-C00128
    Figure US20240025934A1-20240125-C00129
  • and each LCj has a structure of Formula X
  • Figure US20240025934A1-20240125-C00130
  • in which R1, R2, and R3 are defined as:
  • Ligand R1 R2 R3
    LC1 RD1 RD1 H
    LC2 RD2 RD2 H
    LC3 RD3 RD3 H
    LC4 RD4 RD4 H
    LC5 RD5 RD5 H
    LC6 RD6 RD6 H
    LC7 RD7 RD7 H
    LC8 RD8 RD8 H
    LC9 RD9 RD9 H
    LC10 RD10 RD10 H
    LC11 RD11 RD11 H
    LC12 RD12 RD12 H
    LC13 RD13 RD13 H
    LC14 RD14 RD14 H
    LC15 RD15 RD15 H
    LC16 RD16 RD16 H
    LC17 RD17 RD17 H
    LC18 RD18 RD18 H
    LC19 RD19 RD19 H
    LC20 RD20 RD20 H
    LC21 RD21 RD21 H
    LC22 RD22 RD22 H
    LC23 RD23 RD23 H
    LC24 RD24 RD24 H
    LC25 RD25 RD25 H
    LC26 RD26 RD26 H
    LC27 RD27 RD27 H
    LC28 RD28 RD28 H
    LC29 RD29 RD29 H
    LC30 RD30 RD30 H
    LC31 RD31 RD31 H
    LC32 RD32 RD32 H
    LC33 RD33 RD33 H
    LC34 RD34 RD34 H
    LC35 RD35 RD35 H
    LC36 RD40 RD40 H
    LC37 RD41 RD41 H
    LC38 RD42 RD42 H
    LC39 RD64 RD64 H
    LC40 RD66 RD66 H
    LC41 RD68 RD68 H
    LC42 RD76 RD76 H
    LC43 RD1 RD2 H
    LC44 RD1 RD3 H
    LC45 RD1 RD4 H
    LC46 RD1 RD5 H
    LC47 RD1 RD6 H
    LC48 RD1 RD7 H
    LC49 RD1 RD8 H
    LC50 RD1 RD9 H
    LC51 RD1 RD10 H
    LC52 RD1 RD11 H
    LC53 RD1 RD12 H
    LC54 RD1 RD13 H
    LC55 RD1 RD14 H
    LC56 RD1 RD15 H
    LC57 RD1 RD16 H
    LC58 RD1 RD17 H
    LC59 RD1 RD18 H
    LC60 RD1 RD19 H
    LC61 RD1 RD20 H
    LC62 RD1 RD21 H
    LC63 RD1 RD22 H
    LC64 RD1 RD23 H
    LC65 RD1 RD24 H
    LC66 RD1 RD25 H
    LC67 RD1 RD26 H
    LC68 RD1 RD27 H
    LC69 RD1 RD28 H
    LC70 RD1 RD29 H
    LC71 RD1 RD30 H
    LC72 RD1 RD31 H
    LC73 RD1 RD32 H
    LC74 RD1 RD33 H
    LC75 RD1 RD34 H
    LC76 RD1 RD35 H
    LC77 RD1 RD40 H
    LC78 RD1 RD41 H
    LC79 RD1 RD42 H
    LC80 RD1 RD64 H
    LC81 RD1 RD66 H
    LC82 RD1 RD68 H
    LC83 RD1 RD76 H
    LC84 RD2 RD1 H
    LC85 RD2 RD3 H
    LC86 RD2 RD4 H
    LC87 RD2 RD5 H
    LC88 RD2 RD6 H
    LC89 RD2 RD7 H
    LC90 RD2 RD8 H
    LC91 RD2 RD9 H
    LC92 RD2 RD10 H
    LC93 RD2 RD11 H
    LC94 RD2 RD12 H
    LC95 RD2 RD13 H
    LC96 RD2 RD14 H
    LC97 RD2 RD15 H
    LC98 RD2 RD16 H
    LC99 RD2 RD17 H
    LC100 RD2 RD18 H
    LC101 RD2 RD19 H
    LC102 RD2 RD20 H
    LC103 RD2 RD21 H
    LC104 RD2 RD22 H
    LC105 RD2 RD23 H
    LC106 RD2 RD24 H
    LC107 RD2 RD25 H
    LC108 RD2 RD26 H
    LC109 RD2 RD27 H
    LC110 RD2 RD28 H
    LC111 RD2 RD29 H
    LC112 RD2 RD30 H
    LC113 RD2 RD31 H
    LC114 RD2 RD32 H
    LC115 RD2 RD33 H
    LC116 RD2 RD34 H
    LC117 RD2 RD35 H
    LC118 RD2 RD40 H
    LC119 RD2 RD41 H
    LC120 RD2 RD42 H
    LC121 RD2 RD64 H
    LC122 RD2 RD66 H
    LC123 RD2 RD68 H
    LC124 RD2 RD76 H
    LC125 RD3 RD4 H
    LC126 RD3 RD5 H
    LC127 RD3 RD6 H
    LC128 RD3 RD7 H
    LC129 RD3 RD8 H
    LC130 RD3 RD9 H
    LC131 RD3 RD10 H
    LC132 RD3 RD11 H
    LC133 RD3 RD12 H
    LC134 RD3 RD13 H
    LC135 RD3 RD14 H
    LC136 RD3 RD15 H
    LC137 RD3 RD16 H
    LC138 RD3 RD17 H
    LC139 RD3 RD18 H
    LC140 RD3 RD19 H
    LC141 RD3 RD20 H
    LC142 RD3 RD21 H
    LC143 RD3 RD22 H
    LC144 RD3 RD23 H
    LC145 RD3 RD24 H
    LC146 RD3 RD25 H
    LC147 RD3 RD26 H
    LC148 RD3 RD27 H
    LC149 RD3 RD28 H
    LC150 RD3 RD29 H
    LC151 RD3 RD30 H
    LC152 RD3 RD31 H
    LC153 RD3 RD32 H
    LC154 RD3 RD33 H
    LC155 RD3 RD34 H
    LC156 RD3 RD35 H
    LC157 RD3 RD40 H
    LC158 RD3 RD41 H
    LC159 RD3 RD42 H
    LC160 RD3 RD64 H
    LC161 RD3 RD66 H
    LC162 RD3 RD68 H
    LC163 RD3 RD76 H
    LC164 RD4 RD5 H
    LC165 RD4 RD6 H
    LC166 RD4 RD7 H
    LC167 RD4 RD8 H
    LC168 RD4 RD9 H
    LC169 RD4 RD10 H
    LC170 RD4 RD11 H
    LC171 RD4 RD12 H
    LC172 RD4 RD13 H
    LC173 RD4 RD14 H
    LC174 RD4 RD15 H
    LC175 RD4 RD16 H
    LC176 RD4 RD17 H
    LC177 RD4 RD18 H
    LC178 RD4 RD19 H
    LC179 RD4 RD20 H
    LC180 RD4 RD21 H
    LC181 RD4 RD22 H
    LC182 RD4 RD23 H
    LC183 RD4 RD24 H
    LC184 RD4 RD25 H
    LC185 RD4 RD26 H
    LC186 RD4 RD27 H
    LC187 RD4 RD28 H
    LC188 RD4 RD29 H
    LC189 RD4 RD30 H
    LC190 RD4 RD31 H
    LC191 RD4 RD32 H
    LC192 RD4 RD33 H
    LC193 RD4 RD34 H
    LC194 RD4 RD35 H
    LC195 RD4 RD40 H
    LC196 RD4 RD41 H
    LC197 RD4 RD42 H
    LC198 RD4 RD64 H
    LC199 RD4 RD66 H
    LC200 RD4 RD68 H
    LC201 RD4 RD76 H
    LC202 RD4 RD1 H
    LC203 RD7 RD5 H
    LC204 RD7 RD6 H
    LC205 RD7 RD8 H
    LC206 RD7 RD9 H
    LC207 RD7 RD10 H
    LC208 RD7 RD11 H
    LC209 RD7 RD12 H
    LC210 RD7 RD13 H
    LC211 RD7 RD14 H
    LC212 RD7 RD15 H
    LC213 RD7 RD16 H
    LC214 RD7 RD17 H
    LC215 RD7 RD18 H
    LC216 RD7 RD19 H
    LC217 RD7 RD20 H
    LC218 RD7 RD21 H
    LC219 RD7 RD22 H
    LC220 RD7 RD23 H
    LC221 RD7 RD24 H
    LC222 RD7 RD25 H
    LC223 RD7 RD26 H
    LC224 RD7 RD27 H
    LC225 RD7 RD28 H
    LC226 RD7 RD29 H
    LC227 RD7 RD30 H
    LC228 RD7 RD31 H
    LC229 RD7 RD32 H
    LC230 RD7 RD33 H
    LC231 RD7 RD34 H
    LC232 RD7 RD35 H
    LC233 RD7 RD40 H
    LC234 RD7 RD41 H
    LC235 RD7 RD42 H
    LC236 RD7 RD64 H
    LC237 RD7 RD66 H
    LC238 RD7 RD68 H
    LC239 RD7 RD76 H
    LC240 RD8 RD5 H
    LC241 RD8 RD6 H
    LC242 RD8 RD9 H
    LC243 RD8 RD10 H
    LC244 RD8 RD11 H
    LC245 RD8 RD12 H
    LC246 RD8 RD13 H
    LC247 RD8 RD14 H
    LC248 RD8 RD15 H
    LC249 RD8 RD16 H
    LC250 RD8 RD17 H
    LC251 RD8 RD18 H
    LC252 RD8 RD19 H
    LC253 RD8 RD20 H
    LC254 RD8 RD21 H
    LC255 RD8 RD22 H
    LC256 RD8 RD23 H
    LC257 RD8 RD24 H
    LC258 RD8 RD25 H
    LC259 RD8 RD26 H
    LC260 RD8 RD27 H
    LC261 RD8 RD28 H
    LC262 RD8 RD29 H
    LC263 RD8 RD30 H
    LC264 RD8 RD31 H
    LC265 RD8 RD32 H
    LC266 RD8 RD33 H
    LC267 RD8 RD34 H
    LC268 RD8 RD35 H
    LC269 RD8 RD40 H
    LC270 RD8 RD41 H
    LC271 RD8 RD42 H
    LC272 RD8 RD64 H
    LC273 RD8 RD66 H
    LC274 RD8 RD68 H
    LC275 RD8 RD76 H
    LC276 RD11 RD5 H
    LC277 RD11 RD6 H
    LC278 RD11 RD9 H
    LC279 RD11 RD10 H
    LC280 RD11 RD12 H
    LC281 RD11 RD13 H
    LC282 RD11 RD14 H
    LC283 RD11 RD15 H
    LC284 RD11 RD16 H
    LC285 RD11 RD17 H
    LC286 RD11 RD18 H
    LC287 RD11 RD19 H
    LC288 RD11 RD20 H
    LC289 RD11 RD21 H
    LC290 RD11 RD22 H
    LC291 RD11 RD23 H
    LC292 RD11 RD24 H
    LC293 RD11 RD25 H
    LC294 RD11 RD26 H
    LC295 RD11 RD27 H
    LC296 RD11 RD28 H
    LC297 RD11 RD29 H
    LC298 RD11 RD30 H
    LC299 RD11 RD31 H
    LC300 RD11 RD32 H
    LC301 RD11 RD33 H
    LC302 RD11 RD34 H
    LC303 RD11 RD35 H
    LC304 RD11 RD40 H
    LC305 RD11 RD41 H
    LC306 RD11 RD42 H
    LC307 RD11 RD64 H
    LC308 RD11 RD66 H
    LC309 RD11 RD68 H
    LC310 RD11 RD76 H
    LC311 RD13 RD5 H
    LC312 RD13 RD6 H
    LC313 RD13 RD9 H
    LC314 RD13 RD10 H
    LC315 RD13 RD12 H
    LC316 RD13 RD14 H
    LC317 RD13 RD15 H
    LC318 RD13 RD16 H
    LC319 RD13 RD17 H
    LC320 RD13 RD18 H
    LC321 RD13 RD19 H
    LC322 RD13 RD20 H
    LC323 RD13 RD21 H
    LC324 RD13 RD22 H
    LC325 RD13 RD23 H
    LC326 RD13 RD24 H
    LC327 RD13 RD25 H
    LC328 RD13 RD26 H
    LC329 RD13 RD27 H
    LC330 RD13 RD28 H
    LC331 RD13 RD29 H
    LC332 RD13 RD30 H
    LC333 RD13 RD31 H
    LC334 RD13 RD32 H
    LC335 RD13 RD33 H
    LC336 RD13 RD34 H
    LC337 RD13 RD35 H
    LC338 RD13 RD40 H
    LC339 RD13 RD41 H
    LC340 RD13 RD42 H
    LC341 RD13 RD64 H
    LC342 RD13 RD66 H
    LC343 RD13 RD68 H
    LC344 RD13 RD76 H
    LC345 RD14 RD5 H
    LC346 RD14 RD6 H
    LC347 RD14 RD9 H
    LC348 RD14 RD10 H
    LC349 RD14 RD12 H
    LC350 RD14 RD15 H
    LC351 RD14 RD16 H
    LC352 RD14 RD17 H
    LC353 RD14 RD18 H
    LC354 RD14 RD19 H
    LC355 RD14 RD20 H
    LC356 RD14 RD21 H
    LC357 RD14 RD22 H
    LC358 RD14 RD23 H
    LC359 RD14 RD24 H
    LC360 RD14 RD25 H
    LC361 RD14 RD26 H
    LC362 RD14 RD27 H
    LC363 RD14 RD28 H
    LC364 RD14 RD29 H
    LC365 RD14 RD30 H
    LC366 RD14 RD31 H
    LC367 RD14 RD32 H
    LC368 RD14 RD33 H
    LC369 RD14 RD34 H
    LC370 RD14 RD35 H
    LC371 RD14 RD40 H
    LC372 RD14 RD41 H
    LC373 RD14 RD42 H
    LC374 RD14 RD64 H
    LC375 RD14 RD66 H
    LC376 RD14 RD68 H
    LC377 RD14 RD76 H
    LC378 RD22 RD5 H
    LC379 RD22 RD6 H
    LC380 RD22 RD9 H
    LC381 RD22 RD10 H
    LC382 RD22 RD12 H
    LC383 RD22 RD15 H
    LC384 RD22 RD16 H
    LC385 RD22 RD17 H
    LC386 RD22 RD18 H
    LC387 RD22 RD19 H
    LC388 RD22 RD20 H
    LC389 RD22 RD21 H
    LC390 RD22 RD23 H
    LC391 RD22 RD24 H
    LC392 RD22 RD25 H
    LC393 RD22 RD26 H
    LC394 RD22 RD27 H
    LC395 RD22 RD28 H
    LC396 RD22 RD29 H
    LC397 RD22 RD30 H
    LC398 RD22 RD31 H
    LC399 RD22 RD32 H
    LC400 RD22 RD33 H
    LC401 RD22 RD34 H
    LC402 RD22 RD35 H
    LC403 RD22 RD40 H
    LC404 RD22 RD41 H
    LC405 RD22 RD42 H
    LC406 RD22 RD64 H
    LC407 RD22 RD66 H
    LC408 RD22 RD68 H
    LC409 RD22 RD76 H
    LC410 RD26 RD5 H
    LC411 RD26 RD6 H
    LC412 RD26 RD9 H
    LC413 RD26 RD10 H
    LC414 RD26 RD12 H
    LC415 RD26 RD15 H
    LC416 RD26 RD16 H
    LC417 RD26 RD17 H
    LC418 RD26 RD18 H
    LC419 RD26 RD19 H
    LC420 RD26 RD20 H
    LC421 RD26 RD21 H
    LC422 RD26 RD23 H
    LC423 RD26 RD24 H
    LC424 RD26 RD25 H
    LC425 RD26 RD27 H
    LC426 RD26 RD28 H
    LC427 RD26 RD29 H
    LC428 RD26 RD30 H
    LC429 RD26 RD31 H
    LC430 RD26 RD32 H
    LC431 RD26 RD33 H
    LC432 RD26 RD34 H
    LC433 RD26 RD35 H
    LC434 RD26 RD40 H
    LC435 RD26 RD41 H
    LC436 RD26 RD42 H
    LC437 RD26 RD64 H
    LC438 RD26 RD66 H
    LC439 RD26 RD68 H
    LC440 RD26 RD76 H
    LC441 RD35 RD5 H
    LC442 RD35 RD6 H
    LC443 RD35 RD9 H
    LC444 RD35 RD10 H
    LC445 RD35 RD12 H
    LC446 RD35 RD15 H
    LC447 RD35 RD16 H
    LC448 RD35 RD17 H
    LC449 RD35 RD18 H
    LC450 RD35 RD19 H
    LC451 RD35 RD20 H
    LC452 RD35 RD21 H
    LC453 RD35 RD23 H
    LC454 RD35 RD24 H
    LC455 RD35 RD25 H
    LC456 RD35 RD27 H
    LC457 RD35 RD28 H
    LC458 RD35 RD29 H
    LC459 RD35 RD30 H
    LC460 RD35 RD31 H
    LC461 RD35 RD32 H
    LC462 RD35 RD33 H
    LC463 RD35 RD34 H
    LC464 RD35 RD40 H
    LC465 RD35 RD41 H
    LC466 RD35 RD42 H
    LC467 RD35 RD64 H
    LC468 RD35 RD66 H
    LC469 RD35 RD68 H
    LC470 RD35 RD76 H
    LC471 RD40 RD5 H
    LC472 RD40 RD6 H
    LC473 RD40 RD9 H
    LC474 RD40 RD10 H
    LC475 RD40 RD12 H
    LC476 RD40 RD15 H
    LC477 RD40 RD16 H
    LC478 RD40 RD17 H
    LC479 RD40 RD18 H
    LC480 RD40 RD19 H
    LC481 RD40 RD20 H
    LC482 RD40 RD21 H
    LC483 RD40 RD23 H
    LC484 RD40 RD24 H
    LC485 RD40 RD25 H
    LC486 RD40 RD27 H
    LC487 RD40 RD28 H
    LC488 RD40 RD29 H
    LC489 RD40 RD30 H
    LC490 RD40 RD31 H
    LC491 RD40 RD32 H
    LC492 RD40 RD33 H
    LC493 RD40 RD34 H
    LC494 RD40 RD41 H
    LC495 RD40 RD42 H
    LC496 RD40 RD64 H
    LC497 RD40 RD66 H
    LC498 RD40 RD68 H
    LC499 RD40 RD76 H
    LC500 RD41 RD5 H
    LC501 RD41 RD6 H
    LC502 RD41 RD9 H
    LC503 RD41 RD10 H
    LC504 RD41 RD12 H
    LC505 RD41 RD15 H
    LC506 RD41 RD16 H
    LC507 RD41 RD17 H
    LC508 RD41 RD18 H
    LC509 RD41 RD19 H
    LC510 RD41 RD20 H
    LC511 RD41 RD21 H
    LC512 RD41 RD23 H
    LC513 RD41 RD24 H
    LC514 RD41 RD25 H
    LC515 RD41 RD27 H
    LC516 RD41 RD28 H
    LC517 RD41 RD29 H
    LC518 RD41 RD30 H
    LC519 RD41 RD31 H
    LC520 RD41 RD32 H
    LC521 RD41 RD33 H
    LC522 RD41 RD34 H
    LC523 RD41 RD42 H
    LC524 RD41 RD64 H
    LC525 RD41 RD66 H
    LC526 RD41 RD68 H
    LC527 RD41 RD76 H
    LC528 RD64 RD5 H
    LC529 RD64 RD6 H
    LC530 RD64 RD9 H
    LC531 RD64 RD10 H
    LC532 RD64 RD12 H
    LC533 RD64 RD15 H
    LC534 RD64 RD16 H
    LC535 RD64 RD17 H
    LC536 RD64 RD18 H
    LC537 RD64 RD19 H
    LC538 RD64 RD20 H
    LC539 RD64 RD21 H
    LC540 RD64 RD23 H
    LC541 RD64 RD24 H
    LC542 RD64 RD25 H
    LC543 RD64 RD27 H
    LC544 RD64 RD28 H
    LC545 RD64 RD29 H
    LC546 RD64 RD30 H
    LC547 RD64 RD31 H
    LC548 RD64 RD32 H
    LC549 RD64 RD33 H
    LC550 RD64 RD34 H
    LC551 RD64 RD42 H
    LC552 RD64 RD64 H
    LC553 RD64 RD66 H
    LC554 RD64 RD68 H
    LC555 RD64 RD76 H
    LC556 RD66 RD5 H
    LC557 RD66 RD6 H
    LC558 RD66 RD9 H
    LC559 RD66 RD10 H
    LC560 RD66 RD12 H
    LC561 RD66 RD15 H
    LC562 RD66 RD16 H
    LC563 RD66 RD17 H
    LC564 RD66 RD18 H
    LC565 RD66 RD19 H
    LC566 RD66 RD20 H
    LC567 RD66 RD21 H
    LC568 RD66 RD23 H
    LC569 RD66 RD24 H
    LC570 RD66 RD25 H
    LC571 RD66 RD27 H
    LC572 RD66 RD28 H
    LC573 RD66 RD29 H
    LC574 RD66 RD30 H
    LC575 RD66 RD31 H
    LC576 RD66 RD32 H
    LC577 RD66 RD33 H
    LC578 RD66 RD34 H
    LC579 RD66 RD42 H
    LC580 RD66 RD68 H
    LC581 RD66 RD76 H
    LC582 RD68 RD5 H
    LC583 RD68 RD6 H
    LC584 RD68 RD9 H
    LC585 RD68 RD10 H
    LC586 RD68 RD12 H
    LC587 RD68 RD15 H
    LC588 RD68 RD16 H
    LC589 RD68 RD17 H
    LC590 RD68 RD18 H
    LC591 RD68 RD19 H
    LC592 RD68 RD20 H
    LC593 RD68 RD21 H
    LC594 RD68 RD23 H
    LC595 RD68 RD24 H
    LC596 RD68 RD25 H
    LC597 RD68 RD27 H
    LC598 RD68 RD28 H
    LC599 RD68 RD29 H
    LC600 RD68 RD30 H
    LC601 RD68 RD31 H
    LC602 RD68 RD32 H
    LC603 RD68 RD33 H
    LC604 RD68 RD34 H
    LC605 RD68 RD42 H
    LC606 RD68 RD76 H
    LC607 RD76 RD5 H
    LC608 RD76 RD6 H
    LC609 RD76 RD9 H
    LC610 RD76 RD10 H
    LC611 RD76 RD12 H
    LC612 RD76 RD15 H
    LC613 RD76 RD16 H
    LC614 RD76 RD17 H
    LC615 RD76 RD18 H
    LC616 RD76 RD19 H
    LC617 RD76 RD20 H
    LC618 RD76 RD21 H
    LC619 RD76 RD23 H
    LC620 RD76 RD24 H
    LC621 RD76 RD25 H
    LC622 RD76 RD27 H
    LC623 RD76 RD28 H
    LC624 RD76 RD29 H
    LC625 RD76 RD30 H
    LC626 RD76 RD31 H
    LC627 RD76 RD32 H
    LC628 RD76 RD33 H
    LC629 RD76 RD34 H
    LC630 RD76 RD42 H
    LC631 RD1 RD1 RD1
    LC632 RD2 RD2 RD1
    LC633 RD3 RD3 RD1
    LC634 RD4 RD4 RD1
    LC635 RD5 RD5 RD1
    LC636 RD6 RD6 RD1
    LC637 RD7 RD7 RD1
    LC638 RD8 RD8 RD1
    LC639 RD9 RD9 RD1
    LC640 RD10 RD10 RD1
    LC641 RD11 RD11 RD1
    LC642 RD12 RD12 RD1
    LC643 RD13 RD13 RD1
    LC644 RD14 RD14 RD1
    LC645 RD15 RD15 RD1
    LC646 RD16 RD16 RD1
    LC647 RD17 RD17 RD1
    LC648 RD18 RD18 RD1
    LC649 RD19 RD19 RD1
    LC650 RD20 RD20 RD1
    LC651 RD21 RD21 RD1
    LC652 RD22 RD22 RD1
    LC653 RD23 RD23 RD1
    LC654 RD24 RD24 RD1
    LC655 RD25 RD25 RD1
    LC656 RD26 RD26 RD1
    LC657 RD27 RD27 RD1
    LC658 RD28 RD28 RD1
    LC659 RD29 RD29 RD1
    LC660 RD30 RD30 RD1
    LC661 RD31 RD31 RD1
    LC662 RD32 RD32 RD1
    LC663 RD33 RD33 RD1
    LC664 RD34 RD34 RD1
    LC665 RD35 RD35 RD1
    LC666 RD40 RD40 RD1
    LC667 RD41 RD41 RD1
    LC668 RD42 RD42 RD1
    LC669 RD64 RD64 RD1
    LC670 RD66 RD66 RD1
    LC671 RD68 RD68 RD1
    LC672 RD76 RD76 RD1
    LC673 RD1 RD2 RD1
    LC674 RD1 RD3 RD1
    LC675 RD1 RD4 RD1
    LC676 RD1 RD5 RD1
    LC677 RD1 RD6 RD1
    LC678 RD1 RD7 RD1
    LC679 RD1 RD8 RD1
    LC680 RD1 RD9 RD1
    LC681 RD1 RD10 RD1
    LC682 RD1 RD11 RD1
    LC683 RD1 RD12 RD1
    LC684 RD1 RD13 RD1
    LC685 RD1 RD14 RD1
    LC686 RD1 RD15 RD1
    LC687 RD1 RD16 RD1
    LC688 RD1 RD17 RD1
    LC689 RD1 RD8 RD1
    LC690 RD1 RD9 RD1
    LC691 RD1 RD20 RD1
    LC692 RD1 RD21 RD1
    LC693 RD1 RD22 RD1
    LC694 RD1 RD23 RD1
    LC695 RD1 RD24 RD1
    LC696 RD1 RD25 RD1
    LC697 RD1 RD26 RD1
    LC698 RD1 RD27 RD1
    LC699 RD1 RD28 RD1
    LC700 RD1 RD29 RD1
    LC701 RD1 RD30 RD1
    LC702 RD1 RD31 RD1
    LC703 RD1 RD32 RD1
    LC704 RD1 RD33 RD1
    LC705 RD1 RD34 RD1
    LC706 RD1 RD35 RD1
    LC707 RD1 RD40 RD1
    LC708 RD1 RD41 RD1
    LC709 RD1 RD42 RD1
    LC710 RD1 RD64 RD1
    LC711 RD1 RD66 RD1
    LC712 RD1 RD68 RD1
    LC713 RD1 RD76 RD1
    LC714 RD2 RD1 RD1
    LC715 RD2 RD3 RD1
    LC716 RD2 RD4 RD1
    LC717 RD2 RD5 RD1
    LC718 RD2 RD6 RD1
    LC719 RD2 RD7 RD1
    LC720 RD2 RD8 RD1
    LC721 RD2 RD9 RD1
    LC722 RD2 RD10 RD1
    LC723 RD2 RD11 RD1
    LC724 RD2 RD12 RD1
    LC725 RD2 RD13 RD1
    LC726 RD2 RD14 RD1
    LC727 RD2 RD15 RD1
    LC728 RD2 RD16 RD1
    LC729 RD2 RD17 RD1
    LC730 RD2 RD18 RD1
    LC731 RD2 RD19 RD1
    LC732 RD2 RD20 RD1
    LC733 RD2 RD21 RD1
    LC734 RD2 RD22 RD1
    LC735 RD2 RD23 RD1
    LC736 RD2 RD24 RD1
    LC737 RD2 RD25 RD1
    LC738 RD2 RD26 RD1
    LC739 RD2 RD27 RD1
    LC740 RD2 RD28 RD1
    LC741 RD2 RD29 RD1
    LC742 RD2 RD30 RD1
    LC743 RD2 RD31 RD1
    LC744 RD2 RD32 RD1
    LC745 RD2 RD33 RD1
    LC746 RD2 RD34 RD1
    LC747 RD2 RD35 RD1
    LC748 RD2 RD40 RD1
    LC749 RD2 RD41 RD1
    LC750 RD2 RD42 RD1
    LC751 RD2 RD64 RD1
    LC752 RD2 RD66 RD1
    LC753 RD2 RD68 RD1
    LC754 RD2 RD76 RD1
    LC755 RD3 RD4 RD1
    LC756 RD3 RD5 RD1
    LC757 RD3 RD6 RD1
    LC758 RD3 RD7 RD1
    LC759 RD3 RD8 RD1
    LC760 RD3 RD9 RD1
    LC761 RD3 RD10 RD1
    LC762 RD3 RD11 RD1
    LC763 RD3 RD12 RD1
    LC764 RD3 RD13 RD1
    LC765 RD3 RD14 RD1
    LC766 RD3 RD15 RD1
    LC767 RD3 RD6 RD1
    LC768 RD3 RD17 RD1
    LC769 RD3 RD18 RD1
    LC770 RD3 RD19 RD1
    LC771 RD3 RD20 RD1
    LC772 RD3 RD21 RD1
    LC773 RD3 RD22 RD1
    LC774 RD3 RD23 RD1
    LC775 RD3 RD24 RD1
    LC776 RD3 RD25 RD1
    LC777 RD3 RD26 RD1
    LC778 RD3 RD27 RD1
    LC779 RD3 RD28 RD1
    LC780 RD3 RD29 RD1
    LC781 RD3 RD30 RD1
    LC782 RD3 RD31 RD1
    LC783 RD3 RD32 RD1
    LC784 RD3 RD33 RD1
    LC785 RD3 RD34 RD1
    LC786 RD3 RD35 RD1
    LC787 RD3 RD40 RD1
    LC788 RD3 RD41 RD1
    LC789 RD3 RD42 RD1
    LC790 RD3 RD64 RD1
    LC791 RD3 RD66 RD1
    LC792 RD3 RD68 RD1
    LC793 RD3 RD76 RD1
    LC794 RD4 RD5 RD1
    LC795 RD4 RD6 RD1
    LC796 RD4 RD7 RD1
    LC797 RD4 RD8 RD1
    LC798 RD4 RD9 RD1
    LC799 RD4 RD10 RD1
    LC800 RD4 RD11 RD1
    LC801 RD4 RD12 RD1
    LC802 RD4 RD13 RD1
    LC803 RD4 RD14 RD1
    LC804 RD4 RD15 RD1
    LC805 RD4 RD16 RD1
    LC806 RD4 RD17 RD1
    LC807 RD4 RD18 RD1
    LC808 RD4 RD19 RD1
    LC809 RD4 RD20 RD1
    LC810 RD4 RD21 RD1
    LC811 RD4 RD22 RD1
    LC812 RD4 RD23 RD1
    LC813 RD4 RD24 RD1
    LC814 RD4 RD25 RD1
    LC815 RD4 RD26 RD1
    LC816 RD4 RD27 RD1
    LC817 RD4 RD28 RD1
    LC818 RD4 RD29 RD1
    LC819 RD4 RD30 RD1
    LC820 RD4 RD31 RD1
    LC821 RD4 RD32 RD1
    LC822 RD4 RD33 RD1
    LC823 RD4 RD34 RD1
    LC824 RD4 RD35 RD1
    LC825 RD4 RD40 RD1
    LC826 RD4 RD41 RD1
    LC827 RD4 RD42 RD1
    LC828 RD4 RD64 RD1
    LC829 RD4 RD66 RD1
    LC830 RD4 RD68 RD1
    LC831 RD4 RD76 RD1
    LC832 RD4 RD1 RD1
    LC833 RD7 RD5 RD1
    LC834 RD7 RD6 RD1
    LC835 RD7 RD8 RD1
    LC836 RD7 RD9 RD1
    LC837 RD7 RD10 RD1
    LC838 RD7 RD11 RD1
    LC839 RD7 RD12 RD1
    LC840 RD7 RD13 RD1
    LC841 RD7 RD14 RD1
    LC842 RD7 RD15 RD1
    LC843 RD7 RD16 RD1
    LC844 RD7 RD17 RD1
    LC845 RD7 RD18 RD1
    LC846 RD7 RD19 RD1
    LC847 RD7 RD20 RD1
    LC848 RD7 RD21 RD1
    LC849 RD7 RD22 RD1
    LC850 RD7 RD23 RD1
    LC851 RD7 RD24 RD1
    LC852 RD7 RD25 RD1
    LC853 RD7 RD26 RD1
    LC854 RD7 RD27 RD1
    LC855 RD7 RD28 RD1
    LC856 RD7 RD29 RD1
    LC857 RD7 RD30 RD1
    LC858 RD7 RD31 RD1
    LC859 RD7 RD32 RD1
    LC860 RD7 RD33 RD1
    LC861 RD7 RD34 RD1
    LC862 RD7 RD35 RD1
    LC863 RD7 RD40 RD1
    LC864 RD7 RD41 RD1
    LC865 RD7 RD42 RD1
    LC866 RD7 RD64 RD1
    LC867 RD7 RD66 RD1
    LC868 RD7 RD68 RD1
    LC869 RD7 RD76 RD1
    LC870 RD8 RD5 RD1
    LC871 RD8 RD6 RD1
    LC872 RD8 RD9 RD1
    LC873 RD8 RD10 RD1
    LC874 RD8 RD11 RD1
    LC875 RD8 RD12 RD1
    LC876 RD8 RD13 RD1
    LC877 RD8 RD14 RD1
    LC878 RD8 RD15 RD1
    LC879 RD8 RD16 RD1
    LC880 RD8 RD17 RD1
    LC881 RD8 RD18 RD1
    LC882 RD8 RD19 RD1
    LC883 RD8 RD20 RD1
    LC884 RD8 RD21 RD1
    LC885 RD8 RD22 RD1
    LC886 RD8 RD23 RD1
    LC887 RD8 RD24 RD1
    LC888 RD8 RD25 RD1
    LC889 RD8 RD26 RD1
    LC890 RD8 RD27 RD1
    LC891 RD8 RD28 RD1
    LC892 RD8 RD29 RD1
    LC893 RD8 RD30 RD1
    LC894 RD8 RD31 RD1
    LC895 RD8 RD32 RD1
    LC896 RD8 RD33 RD1
    LC897 RD8 RD34 RD1
    LC898 RD8 RD35 RD1
    LC899 RD8 RD40 RD1
    LC900 RD8 RD41 RD1
    LC901 RD8 RD42 RD1
    LC902 RD8 RD64 RD1
    LC903 RD8 RD66 RD1
    LC904 RD8 RD68 RD1
    LC905 RD8 RD76 RD1
    LC906 RD11 RD5 RD1
    LC907 RD11 RD6 RD1
    LC908 RD11 RD9 RD1
    LC909 RD11 RD10 RD1
    LC910 RD11 RD12 RD1
    LC911 RD11 RD13 RD1
    LC912 RD11 RD14 RD1
    LC913 RD11 RD15 RD1
    LC914 RD11 RD16 RD1
    LC915 RD11 RD17 RD1
    LC916 RD11 RD18 RD1
    LC917 RD11 RD19 RD1
    LC918 RD11 RD20 RD1
    LC919 RD11 RD21 RD1
    LC920 RD11 RD22 RD1
    LC921 RD11 RD23 RD1
    LC922 RD11 RD24 RD1
    LC923 RD11 RD25 RD1
    LC924 RD11 RD26 RD1
    LC925 RD11 RD27 RD1
    LC926 RD11 RD28 RD1
    LC927 RD11 RD29 RD1
    LC928 RD11 RD30 RD1
    LC929 RD11 RD31 RD1
    LC930 RD11 RD32 RD1
    LC931 RD11 RD33 RD1
    LC932 RD11 RD34 RD1
    LC933 RD11 RD35 RD1
    LC934 RD11 RD40 RD1
    LC935 RD11 RD41 RD1
    LC936 RD11 RD42 RD1
    LC937 RD11 RD64 RD1
    LC938 RD11 RD66 RD1
    LC939 RD11 RD68 RD1
    LC940 RD11 RD76 RD1
    LC941 RD13 RD5 RD1
    LC942 RD13 RD6 RD1
    LC943 RD13 RD9 RD1
    LC944 RD13 RD10 RD1
    LC945 RD13 RD12 RD1
    LC946 RD13 RD14 RD1
    LC947 RD13 RD15 RD1
    LC948 RD13 RD16 RD1
    LC949 RD13 RD17 RD1
    LC950 RD13 RD18 RD1
    LC951 RD13 RD19 RD1
    LC952 RD13 RD20 RD1
    LC953 RD13 RD21 RD1
    LC954 RD13 RD22 RD1
    LC955 RD13 RD23 RD1
    LC956 RD13 RD24 RD1
    LC957 RD13 RD25 RD1
    LC958 RD13 RD26 RD1
    LC959 RD13 RD27 RD1
    LC960 RD13 RD28 RD1
    LC961 RD13 RD29 RD1
    LC962 RD13 RD30 RD1
    LC963 RD13 RD31 RD1
    LC964 RD13 RD32 RD1
    LC965 RD13 RD33 RD1
    LC966 RD13 RD34 RD1
    LC967 RD13 RD35 RD1
    LC968 RD13 RD40 RD1
    LC969 RD13 RD41 RD1
    LC970 RD13 RD42 RD1
    LC971 RD13 RD64 RD1
    LC972 RD13 RD66 RD1
    LC973 RD13 RD68 RD1
    LC974 RD13 RD76 RD1
    LC975 RD14 RD5 RD1
    LC976 RD14 RD6 RD1
    LC977 RD14 RD9 RD1
    LC978 RD14 RD10 RD1
    LC979 RD14 RD12 RD1
    LC980 RD14 RD15 RD1
    LC981 RD14 RD16 RD1
    LC982 RD14 RD17 RD1
    LC983 RD14 RD18 RD1
    LC984 RD14 RD19 RD1
    LC985 RD14 RD20 RD1
    LC986 RD14 RD21 RD1
    LC987 RD14 RD22 RD1
    LC988 RD14 RD23 RD1
    LC989 RD14 RD24 RD1
    LC990 RD14 RD25 RD1
    LC991 RD14 RD26 RD1
    LC992 RD14 RD27 RD1
    LC993 RD14 RD28 RD1
    LC994 RD14 RD29 RD1
    LC995 RD14 RD30 RD1
    LC996 RD14 RD31 RD1
    LC997 RD14 RD32 RD1
    LC998 RD14 RD33 RD1
    LC999 RD14 RD34 RD1
    LC1000 RD14 RD35 RD1
    LC1001 RD14 RD40 RD1
    LC1002 RD14 RD41 RD1
    LC1003 RD14 RD42 RD1
    LC1004 RD14 RD64 RD1
    LC1005 RD14 RD66 RD1
    LC1006 RD14 RD68 RD1
    LC1007 RD14 RD76 RD1
    LC1008 RD22 RD5 RD1
    LC1009 RD22 RD6 RD1
    LC1010 RD22 RD9 RD1
    LC1011 RD22 RD10 RD1
    LC1012 RD22 RD12 RD1
    LC1013 RD22 RD15 RD1
    LC1014 RD22 RD16 RD1
    LC1015 RD22 RD17 RD1
    LC1016 RD22 RD18 RD1
    LC1017 RD22 RD19 RD1
    LC1018 RD22 RD20 RD1
    LC1019 RD22 RD21 RD1
    LC1020 RD22 RD23 RD1
    LC1021 RD22 RD24 RD1
    LC1022 RD22 RD25 RD1
    LC1023 RD22 RD26 RD1
    LC1024 RD22 RD27 RD1
    LC1025 RD22 RD28 RD1
    LC1026 RD22 RD29 RD1
    LC1027 RD22 RD30 RD1
    LC1028 RD22 RD31 RD1
    LC1029 RD22 RD32 RD1
    LC1030 RD22 RD33 RD1
    LC1031 RD22 RD34 RD1
    LC1032 RD22 RD35 RD1
    LC1033 RD22 RD40 RD1
    LC1034 RD22 RD41 RD1
    LC1035 RD22 RD42 RD1
    LC1036 RD22 RD64 RD1
    LC1037 RD22 RD66 RD1
    LC1038 RD22 RD68 RD1
    LC1039 RD22 RD76 RD1
    LC1040 RD26 RD5 RD1
    LC1041 RD26 RD6 RD1
    LC1042 RD26 RD9 RD1
    LC1043 RD26 RD10 RD1
    LC1044 RD26 RD12 RD1
    LC1045 RD26 RD15 RD1
    LC1046 RD26 RD16 RD1
    LC1047 RD26 RD17 RD1
    LC1048 RD26 RD18 RD1
    LC1049 RD26 RD19 RD1
    LC1050 RD26 RD20 RD1
    LC1051 RD26 RD21 RD1
    LC1052 RD26 RD23 RD1
    LC1053 RD26 RD24 RD1
    LC1054 RD26 RD25 RD1
    LC1055 RD26 RD27 RD1
    LC1056 RD26 RD28 RD1
    LC1057 RD26 RD29 RD1
    LC1058 RD26 RD30 RD1
    LC1059 RD26 RD31 RD1
    LC1060 RD26 RD32 RD1
    LC1061 RD26 RD33 RD1
    LC1062 RD26 RD34 RD1
    LC1063 RD26 RD35 RD1
    LC1064 RD26 RD40 RD1
    LC1065 RD26 RD41 RD1
    LC1066 RD26 RD42 RD1
    LC1067 RD26 RD64 RD1
    LC1068 RD26 RD66 RD1
    LC1069 RD26 RD68 RD1
    LC1070 RD26 RD76 RD1
    LC1071 RD35 RD5 RD1
    LC1072 RD35 RD6 RD1
    LC1073 RD35 RD9 RD1
    LC1074 RD35 RD10 RD1
    LC1075 RD35 RD12 RD1
    LC1076 RD35 RD15 RD1
    LC1077 RD35 RD16 RD1
    LC1078 RD35 RD17 RD1
    LC1079 RD35 RD18 RD1
    LC1080 RD35 RD19 RD1
    LC1081 RD35 RD20 RD1
    LC1082 RD35 RD21 RD1
    LC1083 RD35 RD23 RD1
    LC1084 RD35 RD24 RD1
    LC1085 RD35 RD25 RD1
    LC1086 RD35 RD27 RD1
    LC1087 RD35 RD28 RD1
    LC1088 RD35 RD29 RD1
    LC1089 RD35 RD30 RD1
    LC1090 RD35 RD31 RD1
    LC1091 RD35 RD32 RD1
    LC1092 RD35 RD33 RD1
    LC1093 RD35 RD34 RD1
    LC1094 RD35 RD40 RD1
    LC1095 RD35 RD41 RD1
    LC1096 RD35 RD42 RD1
    LC1097 RD35 RD64 RD1
    LC1098 RD35 RD66 RD1
    LC1099 RD35 RD68 RD1
    LC1100 RD35 RD76 RD1
    LC1101 RD40 RD5 RD1
    LC1102 RD40 RD6 RD1
    LC1103 RD40 RD9 RD1
    LC1104 RD40 RD10 RD1
    LC1105 RD40 RD12 RD1
    LC1106 RD40 RD15 RD1
    LC1107 RD40 RD16 RD1
    LC1108 RD40 RD17 RD1
    LC1109 RD40 RD8 RD1
    LC1110 RD40 RD9 RD1
    LC1111 RD40 RD20 RD1
    LC1112 RD40 RD21 RD1
    LC1113 RD40 RD23 RD1
    LC1114 RD40 RD24 RD1
    LC1115 RD40 RD25 RD1
    LC1116 RD40 RD27 RD1
    LC1117 RD40 RD28 RD1
    LC1118 RD40 RD29 RD1
    LC1119 RD40 RD30 RD1
    LC1120 RD40 RD31 RD1
    LC1121 RD40 RD32 RD1
    LC1122 RD40 RD33 RD1
    LC1123 RD40 RD34 RD1
    LC1124 RD40 RD41 RD1
    LC1125 RD40 RD42 RD1
    LC1126 RD40 RD64 RD1
    LC1127 RD40 RD66 RD1
    LC1128 RD40 RD68 RD1
    LC1129 RD40 RD76 RD1
    LC1130 RD41 RD5 RD1
    LC1131 RD41 RD6 RD1
    LC1132 RD41 RD9 RD1
    LC1133 RD41 RD10 RD1
    LC1134 RD41 RD12 RD1
    LC1135 RD41 RD15 RD1
    LC1136 RD41 RD16 RD1
    LC1137 RD41 RD17 RD1
    LC1138 RD41 RD18 RD1
    LC1139 RD41 RD19 RD1
    LC1140 RD41 RD20 RD1
    LC1141 RD41 RD21 RD1
    LC1142 RD41 RD23 RD1
    LC1143 RD41 RD24 RD1
    LC1144 RD41 RD25 RD1
    LC1145 RD41 RD27 RD1
    LC1146 RD41 RD28 RD1
    LC1147 RD41 RD29 RD1
    LC1148 RD41 RD30 RD1
    LC1149 RD41 RD31 RD1
    LC1150 RD41 RD32 RD1
    LC1151 RD41 RD33 RD1
    LC1152 RD41 RD34 RD1
    LC1153 RD41 RD42 RD1
    LC1154 RD41 RD64 RD1
    LC1155 RD41 RD66 RD1
    LC1156 RD41 RD68 RD1
    LC1157 RD41 RD76 RD1
    LC1158 RD64 RD5 RD1
    LC1159 RD64 RD6 RD1
    LC1160 RD64 RD9 RD1
    LC1161 RD64 RD10 RD1
    LC1162 RD64 RD12 RD1
    LC1163 RD64 RD15 RD1
    LC1164 RD64 RD16 RD1
    LC1165 RD64 RD17 RD1
    LC1166 RD64 RD18 RD1
    LC1167 RD64 RD19 RD1
    LC1168 RD64 RD20 RD1
    LC1169 RD64 RD21 RD1
    LC1170 RD64 RD23 RD1
    LC1171 RD64 RD24 RD1
    LC1172 RD64 RD25 RD1
    LC1173 RD64 RD27 RD1
    LC1174 RD64 RD28 RD1
    LC1175 RD64 RD29 RD1
    LC1176 RD64 RD30 RD1
    LC1177 RD64 RD31 RD1
    LC1178 RD64 RD32 RD1
    LC1179 RD64 RD33 RD1
    LC1180 RD64 RD34 RD1
    LC1181 RD64 RD42 RD1
    LC1182 RD64 RD64 RD1
    LC1183 RD64 RD66 RD1
    LC1184 RD64 RD68 RD1
    LC1185 RD64 RD76 RD1
    LC1186 RD66 RD5 RD1
    LC1187 RD66 RD6 RD1
    LC1188 RD66 RD9 RD1
    LC1189 RD66 RD10 RD1
    LC1190 RD66 RD12 RD1
    LC1191 RD66 RD15 RD1
    LC1192 RD66 RD16 RD1
    LC1193 RD66 RD17 RD1
    LC1194 RD66 RD18 RD1
    LC1195 RD66 RD19 RD1
    LC1196 RD66 RD20 RD1
    LC1197 RD66 RD21 RD1
    LC1198 RD66 RD23 RD1
    LC1199 RD66 RD24 RD1
    LC1200 RD66 RD25 RD1
    LC1201 RD66 RD27 RD1
    LC1202 RD66 RD28 RD1
    LC1203 RD66 RD29 RD1
    LC1204 RD66 RD30 RD1
    LC1205 RD66 RD31 RD1
    LC1206 RD66 RD32 RD1
    LC1207 RD66 RD33 RD1
    LC1208 RD66 RD34 RD1
    LC1209 RD66 RD42 RD1
    LC1210 RD66 RD68 RD1
    LC1211 RD66 RD76 RD1
    LC1212 RD68 RD5 RD1
    LC1213 RD68 RD6 RD1
    LC1214 RD68 RD9 RD1
    LC1215 RD68 RD10 RD1
    LC1216 RD68 RD12 RD1
    LC1217 RD68 RD15 RD1
    LC1218 RD68 RD16 RD1
    LC1219 RD68 RD17 RD1
    LC1220 RD68 RD18 RD1
    LC1221 RD68 RD19 RD1
    LC1222 RD68 RD20 RD1
    LC1223 RD68 RD21 RD1
    LC1224 RD68 RD23 RD1
    LC1225 RD68 RD24 RD1
    LC1226 RD68 RD25 RD1
    LC1227 RD68 RD27 RD1
    LC1228 RD68 RD28 RD1
    LC1229 RD68 RD29 RD1
    LC1230 RD68 RD30 RD1
    LC1231 RD68 RD31 RD1
    LC1232 RD68 RD32 RD1
    LC1233 RD68 RD33 RD1
    LC1234 RD68 RD34 RD1
    LC1235 RD68 RD42 RD1
    LC1236 RD68 RD76 RD1
    LC1237 RD76 RD5 RD1
    LC1238 RD76 RD6 RD1
    LC1239 RD76 RD9 RD1
    LC1240 RD76 RD10 RD1
    LC1241 RD76 RD12 RD1
    LC1242 RD76 RD15 RD1
    LC1243 RD76 RD16 RD1
    LC1244 RD76 RD17 RD1
    LC1245 RD76 RD18 RD1
    LC1246 RD76 RD19 RD1
    LC1247 RD76 RD20 RD1
    LC1248 RD76 RD21 RD1
    LC1249 RD76 RD23 RD1
    LC1250 RD76 RD24 RD1
    LC1251 RD76 RD25 RD1
    LC1252 RD76 RD27 RD1
    LC1253 RD76 RD28 RD1
    LC1254 RD76 RD29 RD1
    LC1255 RD76 RD30 RD1
    LC1256 RD76 RD31 RD1
    LC1257 RD76 RD32 RD1
    LC1258 RD76 RD33 RD1
    LC1259 RD76 RD34 RD1
    LC1260 RD76 RD42 RD1,

    where RD1 to RD21 have the following structures:
  • Figure US20240025934A1-20240125-C00131
    Figure US20240025934A1-20240125-C00132
    Figure US20240025934A1-20240125-C00133
    Figure US20240025934A1-20240125-C00134
    Figure US20240025934A1-20240125-C00135
    Figure US20240025934A1-20240125-C00136
    Figure US20240025934A1-20240125-C00137
    Figure US20240025934A1-20240125-C00138
    Figure US20240025934A1-20240125-C00139
  • According to another aspect, an organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode is disclosed. The organic layer comprises the compound comprising the ligand LA of Formula I
  • Figure US20240025934A1-20240125-C00140
  • described herein.
  • A consumer product also disclosed that comprises the OLED whose organic layer comprises the compound comprising the ligand LA of Formula I described herein.
  • In some embodiments, the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.
  • In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises a RGB pixel arrangement or white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a hand held device, or a wearable device. In some embodiments, the OLED is a display panel having less than 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a display panel having at least 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a lighting panel.
  • An emissive region in an OLED is also disclosed. The emissive region comprises the compound comprising the ligand LA of Formula I
  • Figure US20240025934A1-20240125-C00141
  • described herein.
  • In some embodiments of the emissive region, the compound is an emissive dopant or a non-emissive dopant. In some embodiments, the emissive region further comprises a host, wherein the host contains at least one group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
  • In some embodiments, the emissive region further comprises a host, wherein the host is selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00142
    Figure US20240025934A1-20240125-C00143
    Figure US20240025934A1-20240125-C00144
    Figure US20240025934A1-20240125-C00145
    Figure US20240025934A1-20240125-C00146
    Figure US20240025934A1-20240125-C00147
  • and combinations thereof.
  • In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. application Ser. No. 15/700,352, published on Mar. 14, 2019 as U.S. patent application publication No. 2019/0081248, which is hereby incorporated by reference in its entirety), triplet-triplet annihilation, or combinations of these processes. In some embodiments, the emissive dopant can be a racemic mixture, or can be enriched in one enantiomer. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from others).
  • When there are more than one ligand coordinated to a metal, the ligands can all be the same in some embodiments. In some other embodiments, at least one ligand is different from the other ligand(s). In some embodiments, every ligand can be different from each other. This is also true in embodiments where a ligand being coordinated to a metal can be linked with other ligands being coordinated to that metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, where the coordinating ligands are being linked together, all of the ligands can be the same in some embodiments, and at least one of the ligands being linked can be different from the other ligand(s) in some other embodiments.
  • In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED where one or multiple layers in the OLED contains an acceptor in the form of one or more fluorescent and/or delayed fluorescence emitters. In some embodiments, the compound can be used as one component of an exciplex to be used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor and the acceptor will emit the energy or further transfer energy to a final emitter. The acceptor concentrations can range from 0.001% to 100%. The acceptor could be in either the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can arise from any or all of the sensitizer, acceptor, and final emitter.
  • According to another aspect, a formulation comprising the compound described herein is also disclosed.
  • The OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.
  • The organic layer can also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡C—CnH2n+1, Ar1, Ar1-Ar2, and CnH2n—Ar1, or the host has no substitutions. In the preceding substituents n can range from 1 to 10; and Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. The host can be an inorganic compound, for example a Zn containing inorganic material e.g. ZnS.
  • The host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The host can include a metal complex. The host can be, but is not limited to, a specific compound selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00148
    Figure US20240025934A1-20240125-C00149
    Figure US20240025934A1-20240125-C00150
    Figure US20240025934A1-20240125-C00151
    Figure US20240025934A1-20240125-C00152
    Figure US20240025934A1-20240125-C00153
  • and combinations thereof.
    Additional information on possible hosts is provided below.
  • In yet another aspect of the present disclosure, a formulation that comprises the novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, electron blocking material, hole blocking material, and an electron transport material, disclosed herein.
  • The present disclosure encompasses any chemical structure comprising the novel compound of the present disclosure, or a monovalent or polyvalent variant thereof. In other words, the inventive compound, or a monovalent or polyvalent variant thereof, can be a part of a larger chemical structure. Such chemical structure can be selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule (also known as supermolecule). As used herein, a “monovalent variant of a compound” refers to a moiety that is identical to the compound except that one hydrogen has been removed and replaced with a bond to the rest of the chemical structure. As used herein, a “polyvalent variant of a compound” refers to a moiety that is identical to the compound except that more than one hydrogen has been removed and replaced with a bond or bonds to the rest of the chemical structure. In the instance of a supramolecule, the inventive compound can also be incorporated into the supramolecule complex without covalent bonds.
  • Combination with Other Materials
  • The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
    • Conductivity Dopants:
  • A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.
  • Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.
  • Figure US20240025934A1-20240125-C00154
    Figure US20240025934A1-20240125-C00155
    Figure US20240025934A1-20240125-C00156
    • HIL/HTL:
      • A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoOX; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.
  • Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
  • Figure US20240025934A1-20240125-C00157
  • Each of Ar1 to Ar9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by 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, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • In one aspect, Ar1 to Ar9 is independently selected from the group consisting of:
  • Figure US20240025934A1-20240125-C00158
  • wherein k is an integer from 1 to 20; X101 to X108 is C (including CH) or N; Z101 is NAr1, O, or S; Ar1 has the same group defined above.
  • Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:
  • Figure US20240025934A1-20240125-C00159
  • wherein Met is a metal, which can have an atomic weight greater than 40; (Y101-Y102) is a bidentate ligand, Y101 and Y102 are independently selected from C, N, O, P, and S; L101 is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.
  • In one aspect, (Y101-Y102) is a 2-phenylpyridine derivative. In another aspect, (Y101-Y102) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc+/Fc couple less than about 0.6 V.
  • Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Ser. No. 06/517,957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, U.S. Pat. Nos. 5,061,569, 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.
  • Figure US20240025934A1-20240125-C00160
    Figure US20240025934A1-20240125-C00161
    Figure US20240025934A1-20240125-C00162
    Figure US20240025934A1-20240125-C00163
    Figure US20240025934A1-20240125-C00164
    Figure US20240025934A1-20240125-C00165
    Figure US20240025934A1-20240125-C00166
    Figure US20240025934A1-20240125-C00167
    Figure US20240025934A1-20240125-C00168
    Figure US20240025934A1-20240125-C00169
    Figure US20240025934A1-20240125-C00170
    Figure US20240025934A1-20240125-C00171
    Figure US20240025934A1-20240125-C00172
    Figure US20240025934A1-20240125-C00173
    Figure US20240025934A1-20240125-C00174
    Figure US20240025934A1-20240125-C00175
    Figure US20240025934A1-20240125-C00176
  • An electron blocking layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.
    • Host:
  • The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.
  • Examples of metal complexes used as host are preferred to have the following general formula:
  • Figure US20240025934A1-20240125-C00177
  • wherein Met is a metal; (Y103-Y104) is a bidentate ligand, Y103 and Y104 are independently selected from C, N, O, P, and S; L101 is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.
  • In one aspect, the metal complexes are:
  • Figure US20240025934A1-20240125-C00178
  • wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
  • In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y103-Y104) is a carbene ligand.
  • In one aspect, the host compound contains at least one of the following groups selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by 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, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • In one aspect, the host compound contains at least one of the following groups in the molecule:
  • Figure US20240025934A1-20240125-C00179
    Figure US20240025934A1-20240125-C00180
  • wherein R101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20. X101 to X108 are independently selected from C (including CH) or N. Z101 and Z102 are independently selected from NR101, O, or S.
  • Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, U.S. Pat. No. 9,466,803,
  • Figure US20240025934A1-20240125-C00181
    Figure US20240025934A1-20240125-C00182
    Figure US20240025934A1-20240125-C00183
    Figure US20240025934A1-20240125-C00184
    Figure US20240025934A1-20240125-C00185
    Figure US20240025934A1-20240125-C00186
    Figure US20240025934A1-20240125-C00187
    Figure US20240025934A1-20240125-C00188
    Figure US20240025934A1-20240125-C00189
    Figure US20240025934A1-20240125-C00190
    Figure US20240025934A1-20240125-C00191
    Figure US20240025934A1-20240125-C00192
    Figure US20240025934A1-20240125-C00193
    Figure US20240025934A1-20240125-C00194
    • Additional Emitters:
  • One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
  • Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No. 06/916,554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, U.S. Pat. Nos. 6,303,238, 6,413,656, 6,653,654, 6,670,645, 6,687,266, 6,835,469, 6,921,915, 7,279,704, 7,332,232, 7,378,162, 7,534,505, 7,675,228, 7,728,137, 7,740,957, 7,759,489, 7,951,947, 8,067,099, 8,592,586, 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.
  • Figure US20240025934A1-20240125-C00195
    Figure US20240025934A1-20240125-C00196
    Figure US20240025934A1-20240125-C00197
    Figure US20240025934A1-20240125-C00198
    Figure US20240025934A1-20240125-C00199
    Figure US20240025934A1-20240125-C00200
    Figure US20240025934A1-20240125-C00201
    Figure US20240025934A1-20240125-C00202
    Figure US20240025934A1-20240125-C00203
    Figure US20240025934A1-20240125-C00204
    Figure US20240025934A1-20240125-C00205
    Figure US20240025934A1-20240125-C00206
    Figure US20240025934A1-20240125-C00207
    Figure US20240025934A1-20240125-C00208
    Figure US20240025934A1-20240125-C00209
    Figure US20240025934A1-20240125-C00210
    Figure US20240025934A1-20240125-C00211
    Figure US20240025934A1-20240125-C00212
    Figure US20240025934A1-20240125-C00213
    Figure US20240025934A1-20240125-C00214
    Figure US20240025934A1-20240125-C00215
    • HBL:
  • A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
  • In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.
  • In another aspect, compound used in HBL contains at least one of the following groups in the molecule:
  • Figure US20240025934A1-20240125-C00216
  • wherein k is an integer from 1 to 20; L101 is an another ligand, k′ is an integer from 1 to 3.
    • ETL:
  • Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.
  • In one aspect, compound used in ETL contains at least one of the following groups in the molecule:
  • Figure US20240025934A1-20240125-C00217
  • wherein R101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar1 to Ar3 has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X101 to X108 is selected from C (including CH) or N.
  • In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:
  • Figure US20240025934A1-20240125-C00218
  • wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
  • Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S. Pat. Nos. 6,656,612, 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,
  • Figure US20240025934A1-20240125-C00219
    Figure US20240025934A1-20240125-C00220
    Figure US20240025934A1-20240125-C00221
    Figure US20240025934A1-20240125-C00222
    Figure US20240025934A1-20240125-C00223
    Figure US20240025934A1-20240125-C00224
    Figure US20240025934A1-20240125-C00225
    Figure US20240025934A1-20240125-C00226
    Figure US20240025934A1-20240125-C00227
    • Charge Generation Layer (CGL)
  • In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.
  • In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.
    • EXPERIMENTAL
  • All reactions were carried out under nitrogen protection unless specified otherwise. All solvents for reactions were anhydrous and used as received from the commercial sources.
    • Synthesis of Comparative Compound 1 (CC1) Synthesis of 2-(4-Cyclohexylnaphthalen-2-yl)pyridine
  • Figure US20240025934A1-20240125-C00228
  • A mixture of 2-bromo-pyridine (2.8 g, 17.72 mmol), 2-(4-cyclohexyinaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.44 g, 22.12 mmol) and 2M aqueous potassium carbonate (17.5 mL, 35 mmol) in 1,4-dioxane (80 ml) was sparged with nitrogen for 10 minutes. Bis(triphenylphosphine)palladium(II) dichloride (0.375 g, 0.534 mmol) was added and sparging continued for 10 more minutes. The reaction mixture was heated at reflux overnight (˜16 hrs). The reaction mixture was then cooled to room temperature and diluted with water (50 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×100 mL), dried over by sodium sulfate, filtered and concentrated under reduced pressure. The crude product was dissolved in 50% dichloromethane in hexane and passed through a pad of basic alumina (30 g), rinsing with 50% dichloromethane in hexane (50 mL). The product (4.4 g) was recrystallized from methanol to give 2-(4-cyclohexylnaphthalen-2-yl)pyridine (4.21 g, 83% yield) as a white solid.
    • Synthesis of CC1
  • Figure US20240025934A1-20240125-C00229
  • (A) A solution of 2-(4-cyclohexylnaphthalen-2-yl)pyridine (1.2 g, 4.2 mmol) in triethyl phosphate (16 mL) was sparged with nitrogen for 10 minutes. Iridium(III) chloride hydrate (862 mg, 2.33 mmol) was added and the reaction mixture stirred at 120° C. for 25 hours. The cooled reaction mixture was diluted with DIUF water (16 mL), filtered and the solid was washed with ethanol (3×10 mL). The solid was air-dried to give di-μ-chloro-tetrakis[(2-(4-cyclohexylnaphth-1′yl)-pyridin-1-yl)]diiridium(III) as an orange solid (2.11 g, >100% yield). (B) A suspension of di-μ-chloro-tetrakis[(2-(4-cyclohexylnaphth-1′yl)-pyridin-1-yl)]diiridium(III) (2.11 g, 1.16 mmol) and acetylacetone (630 mg, 6.3 mmol) in ethanol (25 mL) was sparged with nitrogen for 10 minutes. Powdered potassium carbonate (1.2 g, 8.4 mmol) was added and the reaction mixture stirred at room temperature in the dark for 5 hours. DIUF Water (25 mL) was added, the slurry was stirred for 1 hour, filtered, and the solid was washed with water (3×5 mL) and ethanol (3×5 mL) then air-dried. The orange solid (˜2 g) was loaded onto a column of silica gel (50 g), eluting with 1:1 dichloromethane and hexanes (250 mL). The cleanest product fractions were concentrated and the solid was dried in a vacuum oven at 50° C. to give the compound CC1, bis[(2-(4-cyclohexylnaphthyl-1′-yl)-pyridin-1-yl)]-(2,4-pentanedionato-k2O,O′)iridium(II) (0.81 mg, 40% yield) as an orange solid.
    • Synthesis of Comparative Compound 2 (CC2) Synthesis of 2-(4-cyclohexylnaphthalen-2-yl)-4-methylpyridine
  • Figure US20240025934A1-20240125-C00230
  • A mixture of 2-bromo-4-methylpyridine (3.8 g, 22.09 mmol), 2-(4-cyclohexylnaphhalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.29 g, 27.6 mmol) and 2M aqueous potassium carbonate (17.5 mL, 35 mmol) in 1,4-dioxane (80 mL) was sparged with nitrogen for 10 minutes. Bis(triphenylphosphine) palladium(II) dichloride (0.543 g, 0.773 mmol) was added and sparging continued for 10 more minutes. The reaction mixture was heated at reflux overnight (˜ 16 hours). The reaction mixture was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×100 mL), dried over by sodium sulfate, filtered and concentrated under reduced pressure. The crude product was dissolved in 50% dichloromethane in hexane and passed through a pad of basic alumina (30 g), rinsing with 50% dichloromethane in hexane (50 mL), and the filtrate was concentrated under reduced pressure. The crude product was purified with 120 g silica gel column, eluting with 33 to 66% dichloromethane in hexanes The product (4.4 g) was recrystallized from methanol to give 2-(4-cyclohexylnaphthalen-2-yl)-4-methylpyridine (6.2 g, 93% yield) as an off-white solid.
    • Synthesis of CC2
  • Figure US20240025934A1-20240125-C00231
  • (A) A solution of 2-(4-cyclohexylnaphthalen-2-yl)-4-methylpyridine (3.32 g, 11.0 mmol) in 2-ethoxyethanol (120 mL) and DIUF water (30 mL) was sparged with nitrogen for 5 minutes. Iridium(III) chloride hydrate (1.58 g, 5.0 mmol) was added and sparging continued for an additional 5 minutes, then the reaction mixture was heated at 90° C. overnight (˜16 hours). The reaction mixture was cooled to −50° C., filtered, washing the solids with water (2×40 mL). The solid was air-dried for 10 minutes to give di-p-chloro-tetrakis[(2-(4-cyclohexylnaphthalen-2-yl)-4-methylpyridine-2-yl)]diiridium(III) (3.1 g, crude) as a orangish solid. (B) A solution of crude di-p-chloro-tetrakis[(2-(4-cyclohexylnaphthalen-2-yl)-4-*methylpyridine-2-yl)]diiridium(III) (3.07 g, 3.7 mmol) and pentane-2,4-dione (0.74 g, 7.4 mmol) in 2-ethoxyethanol (60 mL) was sparged with nitrogen for 5 minutes, powdered potassium carbonate (1.02 g, 6.0 mmol) was added and sparging continued for 3 additional minutes. The reaction mixture was stirred at room temperature overnight (˜16 hours) in a flask wrapped in aluminum foil to exclude light. DIUF water (60 mL) was added, the suspension was stirred for 30 minutes and the resulting red solid was filtered. The red solid was suspended in dichloromethane (10 mL), loaded directly onto a column of silica gel and the column eluted with 40% dichloro-methane in hexanes. Product fractions were concentrated under reduced pressure and the solid was dried at 50° C. under high vacuum to give the compound CC2, bis[(2-(4-cyclohexylnaphthalen-2-yl)-4-methylpyridine-2-yl)]-(pentane-2,4-dio-nato-k2O,O′)iridium(III) (0.95 g, 22% yield) as an orange solid.
    • Synthesis of Comparative Compound 3 (CC3) Synthesis of 2-(4-Cyclohexylnaphthalen-2-yl)-4-(trifluoromethyl)pyridine
  • Figure US20240025934A1-20240125-C00232
  • 2.0M aq. potassium carbonate (23 mL, 44.2 mmol) was added to a solution of 2-bromo-4-(trifluoromethyl)pyridine (5.0 g, 22.1 mmol), (1-cyclohexylnaphalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.3 g, 27.7 mmol) and trans-dichlorobis(triphenylphosphine)palladium(II) (470 mg, 0.66 mmol) in 1,4-dioxane (100 mL) and the reaction mixture was sparged with nitrogen for 10 minutes. The mixture was heated at reflux for 18 hours before it was cooled to room temperature, saturated brine (20 mL) was added and the layers were separated. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was chromatographed on silica gel, eluting with 30% dichloromethane in heptanes then increasing to 100% dichloromethane to ensure complete elution of product. The product fractions were concentrated under reduced pressure to give 2-(4-cyclo-hexylnaphthalen-2-yl)-4-(trifluoromethyl)pyridine (5.8 g, 75% yield) as a white solid.
    • Synthesis of CC3
  • Figure US20240025934A1-20240125-C00233
  • (A) A solution of 2-(4-cyclohexylnaphthalen-2-yl)-4-(trifluoromethyl)pyridine (3.91 g, 11.0 mmol) in 2-ethoxy-ethanol (120 mL) and DIUF water (30 mL) was sparged with nitrogen for 5 minutes. Iridium(III) chloride hydrate (1.58 g, 5.0 mmol) was added, sparging continued for 5 minutes, then the reaction mixture heated at 90° C. for 7 hours. The reaction mixture was cooled to −50° C., filtered, the solids washed with water (30 mL) then air-dried for 10 minutes to give the compound CC3, di-p-chloro-tetrakis[(2-(4-cyclohexylnaphthalen-2-yl)-4-(trifluoromethyl) pyridine-2-yl)]diiridium(III) (5.5 g, crude) as a reddish solid. (B) A solution of crude di-p-chloro-tetrakis[(2-(4-cyclohexylnaphthalen-2-yl)-4-(trifluoromethyl) pyridine-2-yl)]diiridium(III) (2.81 g, 3.0 mmol) and pentane-2,4-dione (0.6 g, 6.0 mmol) in 2-ethoxyethanol (60 mL) was sparged with nitrogen for 5 minutes. Powdered potassium carbonate (0.829 g, 6.0 mmol) was added and sparging continued for 3 additional minutes. The reaction mixture was stirred at room temperature overnight. DIUF water (60 mL) was added, the suspension stirred for 30 minutes and the solid filtered. The sticky solid was slurried in methanol (40 mL) for 10 minutes, filtered and the solid washed methanol (40 mL). The red solid was loaded onto a column of silica gel and the column eluted with 30% dichloromethane in hexanes. Product fractions were concentrated under reduced pressure and the solid was dried at 50° C. under high vacuum to give the compound CC3, bis[(2-(4-cyclohexyl-naphthalen-2-yl)-4-(trifluoromethyl)pyridine-2-yl)]-(pentane-2,4-dionato-k2O,O′)iridium(III) (1.4 g, 47% overall yield) as a red solid.
    • Synthesis of Comparative Compound 4 (CC4) Synthesis of 4-(tert-Butyl)-2-(4-cyclohexylnaphthalen-2-yl)pyridine
  • Figure US20240025934A1-20240125-C00234
  • A mixture of 4-(tert-butyl)-2-chloropyridine (1.45 g, 8.55 mmol), 2-(4-cyclohexyl-naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.65 g, 10.85 mmol), and 2M aq. potassium carbonate (7.5 mL, 15 mmol) in 1,4-dioxane (40 mL) was sparged with nitrogen for 10 minutes. Bis(triphenyl-phosphine)palladium(II) dichloride (0.240 g, 0.342 mmol) was added and sparging continued for 10 additional minutes, and the reaction mixture was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and diluted with water (5 mL) and ethyl acetate (60 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (2×60 mL). The combined organic layers were washed with saturated brine (2×60 mL), dried over sodium sulfate, filtered and concentrate under reduced pressure. The impure product (6.74 g) was chromatograph-ed on silica gel, eluting with 33-66% dichloromethane in hexane. Product fractions were concentrated under reduced pressure and the solid recrystallized from methanol to give 4-(tert-butyl)-2-(4-cyclohexylnaphthalen-2-yl)pyridine (2.6 g, 89% yield).
    • Synthesis of CC4
  • Figure US20240025934A1-20240125-C00235
  • A mixture of 4-(tert-butyl)-2-(4-cyclohexylnaphthalen-2-yl)pyridine (1.0 g, 145.8 mmol) and triethyl phosphate (6 mL) was sparged with nitrogen for 10 minutes. Iridium(III) chloride hydrate (0.46 g, 1.46 mmol) was added and sparging continued for 5 additional minutes. The reaction mixture was heated at 125° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with methanol (6 mL). Powdered potassium carbonate (0.6 g, 4.37 mmol) and acetylacetone (0.29 g, 2.91 mmol) were added and the reaction mixture stirred at 40° C. for 1 hour. Water (15 mL) was added, the suspension stirred for 30 minutes, filtered and the solid washed with water (3×2 mL) and methanol (3×2 mL). The orange solid was chromatographed on silica gel, eluting with 0-50% dichloromethane in heptane over 45 minutes. Product fractions were concentrated under reduced pressure the residue (0.68 g) triturated with hot hexanes to give the compound CC4, bis[(2-(4-cyclohexylnaphthalen-2-yl)-4-tert-butylpyridin-2-yl)]-(2,4-pentanedionato-k2O,O′)iridium(II) (0.55 g, 39% yield) as an orange solid.
    • Synthesis of Compound C88,222 Synthesis of 2-(4-cyclohexyl-naphthalen-2-yl)-4-(3,3,3-trifluoro-2,2-dimethylpropyl)pyridine
  • Figure US20240025934A1-20240125-C00236
  • (A) A 2 L, four-neck flask was flushed with nitrogen and charged with 2-chloro-4-iodo-pyridine (25.2 g, 105 mmol) in anhydrous tetrahydrofuran (500 mL) while sparging was continued during the addition. Palladium(II) acetate (0.71 g, 3.1 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxy-biphenyl (SPhos) (2.6 g, 6.3 mmol) were added, the mixture was cooled to −1° C., then sparging was discontinued. 0.8M (3,3,3-trifluoro-2,2-dimethylpropyl)zinc(II) bromide in tetrahydrofuran (155 mL, 124 mmol) was added dropwise to the reaction mixture over 30 minutes while maintaining the temperature at below 2° C. The reaction mixture was cooled in an ice bath and 25% sodium hydroxide (200 mL) added dropwise. The layers were separated and the aqueous phase extracted with methyl tert-butyl ether. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure giving a yellow-brown oil. The crude product (33.5 g) was chromatographed on silica gel, eluting with 0-10% ethyl acetate in heptanes, to give 2-chloro-4-(3,3,3-trifluoro-2,2-dimethylpropyl)pyridine (23.0 g, 92% yield) as a yellow oil. (B) A 500 mL four-neck flask was charged with 2-chloro-4-(3,3,3-trifluoro-2,2-dimethylpropyl)pyridine (4.75 g, 20 mmol), 2-(4-cyclohexylnaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.4 g, 22 mmol), 2M aq. potassium carbonate (20 mL, 40 mmol) and ethanol (300 mL) and the mixture was sparged with nitrogen for 10 minutes. SilicaCat DPP-Pd (2.0 g, 0.6 mmol) was added and sparging continued for additional 5 minutes. The reaction mixture was heated at reflux for 19 hours. The reaction mixture was cooled to room temperature, filtered and the solids washed with water (50 mL) and ethanol (100 mL). The solids were dissolved in dichloromethane (30 mL), adsorbed onto silica gel (50 g) and purified by chromatography, eluting with 0-5% ethyl acetate in heptanes, to give 2-(4-cyclohexylnaphthalen-2-yl)-4-(3,3,3-trifluoro-2,2-dimethyl-propyl)pyridine (7.0 g, 85% yield) as a white solid.
    • Synthesis of Compound C88,222
  • Figure US20240025934A1-20240125-C00237
  • (C) A mixture of 2-(4-cyclohexylnaphthalen-2-yl)-4-(3,3,3-trifluoro-2,2-dimethylpropyl)pyridine (4.07 g, 9.9 mmol), 2-ethoxyethanol (120 mL) and DIUF water (30 mL) was sparged with nitrogen for 5 minutes. Iridium(III) chloride hydrate (1.42 g, 4.5 mmol) was added, sparging continued for 5 minutes and the reaction mixture was heated at 90° C. for 48 hours. The reaction mixture was cooled to −60° C., filtered under reduced pressure and the solids washed with water (2×30 mL). The solid was air-dried for 5 minutes to give di-p-chloro-tetrakis[(4-(4-cyclo-hexylnaphthalen-2-yl)-4-(3,3,3-trifluoro-2,2-dimethylpropyl)pyridin-2-yl]-diridium(III) (4.0 g) as an orange solid. (D) A solution of di-p-chloro-tetrakis[(4-(4-cyclohexylnaphthalen-2-yl)-4-(3,3,3-tri-fluoro-2,2-dimethylpropyl)pyridin-2-yl]diiridium(III) (4.08 g, 3.9 mmol) and pentane-2,4-dione (0.78 g, 7.8 mmol) in 2-ethoxyethanol (100 mL) was sparged with nitrogen for 5 minutes. Powdered potassium carbonate (1.08 g, 7.8 mmol) was added and sparging continued for additional 5 minutes. The mixture was stirred at 50° C. for 24 hours. DIUF water (100 mL) was added, the suspension was stirred for 30 minutes, filtered and the slightly sticky solid washed with water (30 mL). The solid was slurried in methanol (50 mL) for 10 minutes, filtered and the solid washed with methanol (50 mL). The red solid was dissolved/suspended in 30% dichloromethane in hexanes (20 mL) and stirred at 35° C. for 30 minutes. The slurry was loaded directly onto a column of silica gel, eluting with 30-40% dichloromethane in hexanes. Product containing fractions were concentrated under reduced pressure and dried at 50° C. in a vacuum oven to give the compound C88,222, [(2-(4-cyclohexyl-naphthalen-2-yl)-4-(3,3,3-tri-fluoro-2,2-dimethylpropyl)pyridin-2-yl]-(2,4-pentanedionato-k2O,O′)iridium(III) (1.8 g, 36% yield over 2 steps) as a red solid.
  • Device Examples
  • All example devices were fabricated by high vacuum (<10-7 Torr) thermal evaporation. The anode electrode was 1150 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (8-hydroxyquinoline lithium) followed by 1,000 Å of A1. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package. The organic stack of the device examples consisted of sequentially, from the ITO surface, 100 Å of LG101 (purchased from LG chem) as the hole injection layer (HIL); 400 Å of HTM as a hole transporting layer (HTL); 300 Å of an emissive layer (EML) containing Compound H as a host, a stability dopant (SD) (18%), and Comparative Compound 1, 2, 3, and 4 (CC1, CC2, CC3, CC4) or Compound C88,222 as the emitter (3%); 100 Å of Compound H as a blocking layer; and 350 Å of Liq (8-hydroxyquinoline lithium) doped with 40% of ETM as the ETL. The emitter was selected to provide the desired color, efficiency and lifetime. The stability dopant (SD) was added to the electron-transporting host to help transport positive charge in the emissive layer. The Comparative Example devices were fabricated similarly to the device examples except that Comparative Compounds were used as the emitters in the EML. Table 1 below provides the materials used for the device layers and the layer thickness.
  • TABLE 1
    Device layer materials and thicknesses
    Layer Material Thickness [Å]
    Anode ITO 1150
    HIL HATCN 100
    HTL HTM 450
    EML Compound H:SD 400
    18%:Emitter 3%
    ETL Liq:ETM 40% 350
    EIL Liq 10
    Cathode Al 1000
  • The device performance data are summarized in Table 2 below. The maximum wavelength of emission (λmax) is very comparable for all comparative compounds (589, 584, 584 nm) and Compound C88,222 (589 nm). The exception is Compound CC3 where a CF3 pendant group was added on the pyridine (631 nm), showing that electron-withdrawing groups on the pyridine lead to bathochromic shift of the emission from an orange color to a deep red color (much lower energy). Since device performance can only be compared with the similar emitting color, it is not suitable to compare CC3 with others tested here except the large color change. The line shape of the emission (FHWM) is similar going from comparative compounds with similar emitting colors to Compound C88,222. The EQE of Compound C88,222 (1.00) was much higher than the EQE of all Comparative Compounds with similar emitting colors (CC1—0.74, CC2—0.81, CC4—0.81). The addition of flexible branched side chains on pyridine units can be responsible this increase in efficiency. Finally, the device lifetime (LT95% at 80 mA/cm2) was also better in the case of Compound C88,222 (1.00) compared to the Comparative Compounds with similar emitting colors (CC1—0.28, CC2—0.44, CC4—C0.34).
  • TABLE 2
    Performance of the devices made with Comparative and Inventive Compounds.
    λ At 10 mA/cm2
    Device 1931 CIE max FWHM Voltage EQE At 80 mA/cm2
    Example Emitter X y [nm] [nm] [au] [au] LT95% [au]
    Example 1 Compound 0.58 0.42 589 1.00 1.00 1.00 1.00
    C88, 222
    CE1 Comparative 0.58 0.42 589 1.03 1.03 0.74 0.28
    Compound 1
    CE2 Comparative 0.57 0.43 584 1.03 1.03 0.81 0.44
    Compound 2
    CE3 Comparative 0.66 0.34 631 1.26 1.00 0.65 1.14
    Compound 3
    CE4 Comparative 0.57 0.43 584 1.06 1.03 0.81 0.34
    Compound 4
  • The chemical structures for the materials used in the experimental OLED devices are shown below:
  • Figure US20240025934A1-20240125-C00238
    Figure US20240025934A1-20240125-C00239
    Figure US20240025934A1-20240125-C00240
  • It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

Claims (20)

We claim:
1. A compound comprising:
a ligand LA of Formula I
Figure US20240025934A1-20240125-C00241
wherein ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring;
wherein each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution;
wherein each RA, RB, and RC is independently a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA has the formula —CH2R or —CHRR′;
wherein each R and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
wherein LA is complexed to a metal M;
wherein M is optionally coordinated to other ligands;
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein any two substituents of RB and RC may be joined or fused together to form a ring.
2. The compound of claim 1, wherein each RA, RB, and RC is independently selected from the group consisting of a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
3. The compound of claim 1, wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au.
4. The compound of claim 1, wherein R is selected from the group consisting of alkyl, cycloalkyl, partially fluorinated variants thereof, partially or fully deuterated variants thereof, and combination thereof.
5. The compound of claim 1, wherein at least one RB comprises a cyclohexyl or tert-butyl group.
6. The compound of claim 1, wherein ring C is selected from the group consisting of benzene, pyridine, pyrimidine, pyrazine, and pyridazine.
7. The compound of claim 1, wherein ring C is a furan or thiofuran ring.
8. The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
Figure US20240025934A1-20240125-C00242
Figure US20240025934A1-20240125-C00243
9. The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
LA1 through LA448 based on a structure of Formula II
Figure US20240025934A1-20240125-C00244
which R1, R2, and G are defined as:
Ligand R1 R2 G LA1 RB3 H RC2 LA2 RB4 H RC2 LA3 RB5 H RC2 LA4 RB18 H RC2 LA5 RB43 H RC2 LA6 RA3 H RC2 LA7 RA34 H RC2 LA8 RA57 H RC2 LA9 RB3 F RC2 LA10 RB4 F RC2 LA11 RB5 F RC2 LA12 RB18 F RC2 LA13 RB43 F RC2 LA14 RA3 F RC2 LA15 RA34 F RC2 LA16 RA57 F RC2 LA17 RB3 RB1 RC2 LA18 RB4 RB1 RC2 LA10 RB5 RB1 RC2 LA20 RB18 RB1 RC2 LA21 RB43 RB1 RC2 LA22 RA3 RB1 RC2 LA23 RA34 RB1 RC2 LA24 RA57 RB1 RC2 LA25 RB3 RA74 RC2 LA26 RB4 RA74 RC2 LA27 RB5 RA74 RC2 LA28 RB18 RA74 RC2 LA29 RB43 RA74 RC2 LA30 RA3 RA74 RC2 LA31 RA34 RA74 RC2 LA32 RA57 RA74 RC2 LA33 RB3 H RC5 LA34 RB4 H RC5 LA35 RB5 H RC5 LA36 RB18 H RC5 LA37 RB43 H RC5 LA38 RA3 H RC5 LA39 RA34 H RC5 LA40 RA57 H RC5 LA41 RB3 F RC5 LA42 RB4 F RC5 LA43 RB5 F RC5 LA44 RB18 F RC5 LA45 RB43 F RC5 LA46 RA3 F RC5 LA47 RA34 F RC5 LA48 RA57 F RC5 LA49 RB3 RB1 RC5 LA50 RB4 RB1 RC5 LA51 RB5 RB1 RC5 LA52 RB18 RB1 RC5 LA53 RB43 RB1 RC5 LA54 RA3 RB1 RC5 LA55 RA34 RB1 RC5 LA56 RA57 RB1 RC5 LA57 RB3 RA74 RC5 LA58 RB4 RA74 RC5 LA59 RB5 RA74 RC5 LA60 RB18 RA74 RC5 LA61 RB43 RA74 RC5 LA62 RA3 RA74 RC5 LA63 RA34 RA74 RC5 LA64 RA57 RA74 RC5 LA65 RB3 H RC6 LA66 RB4 H RC6 LA67 RB5 H RC6 LA68 RB18 H RC6 LA69 RB43 H RC6 LA70 RA3 H RC6 LA71 RA34 H RC6 LA72 RA57 H RC6 LA73 RB3 F RC6 LA74 RB4 F RC6 LA75 RB5 F RC6 LA76 RB18 F RC6 LA77 RB43 F RC6 LA78 RA3 F RC6 LA79 RA34 F RC6 LA80 RA57 F RC6 LA81 RB3 RB1 RC6 LA82 RB4 RB1 RC6 LA83 RB5 RB1 RC6 LA84 RB18 RB1 RC6 LA85 RB43 RB1 RC6 LA86 RA3 RB1 RC6 LA87 RA34 RB1 RC6 LA88 RA57 RB1 RC6 LA89 RB3 RA74 RC6 LA90 RB4 RA74 RC6 LA91 RB5 RA74 RC6 LA92 RB18 RA74 RC6 LA93 RB43 RA74 RC6 LA94 RA3 RA74 RC6 LA95 RA34 RA74 RC6 LA96 RA57 RA74 RC6 LA97 RB3 H RC7 LA98 RB4 H RC7 LA99 RB5 H RC7 LA100 RB18 H RC7 LA101 RB43 H RC7 LA102 RA3 H RC7 LA103 RA34 H RC7 LA104 RA57 H RC7 LA105 RB3 F RC7 LA106 RB4 F RC7 LA107 RB5 F RC7 LA108 RB18 F RC7 LA109 RB43 F RC7 LA110 RA3 F RC7 LA111 RA34 F RC7 LA112 RA57 F RC7 LA113 RB3 RB1 RC7 LA114 RB4 RB1 RC7 LA115 RB5 RB1 RC7 LA116 RB18 RB1 RC7 LA117 RB43 RB1 RC7 LA118 RA3 RB1 RC7 LA119 RA34 RB1 RC7 LA120 RA57 RB1 RC7 LA121 RB3 RA74 RC7 LA122 RB4 RA74 RC7 LA123 RB5 RA74 RC7 LA124 RB18 RA74 RC7 LA125 RB43 RA74 RC7 LA126 RA3 RA74 RC7 LA127 RA34 RA74 RC7 LA128 RA57 RA74 RC7 LA129 RB3 H RC10 LA130 RB4 H RC10 LA131 RB5 H RC10 LA132 RB18 H RC10 LA133 RB43 H RC10 LA134 RA3 H RC10 LA135 RA34 H RC10 LA136 RA57 H RC10 LA137 RB3 F RC10 LA138 RB4 F RC10 LA139 RB5 F RC10 LA140 RB18 F RC10 LA141 RB43 F RC10 LA142 RA3 F RC10 LA143 RA34 F RC10 LA144 RA57 F RC10 LA145 RB3 RB1 RC10 LA146 RB4 RB1 RC10 LA147 RB5 RB1 RC10 LA148 RB18 RB1 RC10 LA149 RB43 RB1 RC10 LA150 RA3 RB1 RC10 LA151 RA34 RB1 RC10 LA152 RA57 RB1 RC10 LA153 RB3 RA74 RC10 LA154 RB4 RA74 RC10 LA155 RB5 RA74 RC10 LA156 RB18 RA74 RC10 LA157 RB43 RA74 RC10 LA158 RA3 RA74 RC10 LA159 RA34 RA74 RC10 LA160 RA57 RA74 RC10 LA161 RB3 H RC11 LA162 RB4 H RC11 LA163 RB5 H RC11 LA164 RB18 H RC11 LA165 RB43 H RC11 LA166 RA3 H RC11 LA167 RA34 H RC11 LA168 RA57 H RC11 LA169 RB3 F RC11 LA170 RB4 F RC11 LA171 RB5 F RC11 LA172 RB18 F RC11 LA173 RB43 F RC11 LA174 RA3 F RC11 LA175 RA34 F RC11 LA176 RA57 F RC11 LA177 RB3 RB1 RC11 LA178 RB4 RB1 RC11 LA179 RB5 RB1 RC11 LA180 RB18 RB1 RC11 LA181 RB43 RB1 RC11 LA182 RA3 RB1 RC11 LA183 RA34 RB1 RC11 LA184 RA57 RB1 RC11 LA185 RB3 RA74 RC11 LA186 RB4 RA74 RC11 LA187 RB5 RA74 RC11 LA188 RB18 RA74 RC11 LA189 RB43 RA74 RC11 LA190 RA3 RA74 RC11 LA191 RA34 RA74 RC11 LA192 RA57 RA74 RC11 LA193 RB3 H RC13 LA194 RB4 H RC13 LA195 RB5 H RC13 LA196 RB18 H RC13 LA197 RB43 H RC13 LA198 RA3 H RC13 LA199 RA34 H RC13 LA200 RA57 H RC13 LA201 RB3 F RC13 LA202 RB4 F RC13 LA203 RB5 F RC13 LA204 RB18 F RC13 LA205 RB43 F RC13 LA206 RA3 F RC13 LA207 RA34 F RC13 LA208 RA57 F RC13 LA209 RB3 RB1 RC13 LA210 RB4 RB1 RC13 LA211 RB5 RB1 RC13 LA212 RB18 RB1 RC13 LA213 RB43 RB1 RC13 LA214 RA3 RB1 RC13 LA215 RA34 RB1 RC13 LA216 RA57 RB1 RC13 LA217 RB3 RA74 RC13 LA218 RB4 RA74 RC13 LA219 RB5 RA74 RC13 LA220 RB18 RA74 RC13 LA221 RB43 RA74 RC13 LA222 RA3 RA74 RC13 LA223 RA34 RA74 RC13 LA224 RA57 RA74 RC13 LA225 RB3 H RC17 LA226 RB4 H RC17 LA227 RB5 H RC17 LA228 RB18 H RC17 LA229 RB43 H RC17 LA230 RA3 H RC17 LA231 RA34 H RC17 LA232 RA57 H RC17 LA233 RB3 F RC17 LA234 RB4 F RC17 LA235 RB5 F RC17 LA236 RB18 F RC17 LA237 RB43 F RC17 LA238 RA3 F RC17 LA239 RA34 F RC17 LA240 RA57 F RC17 LA241 RB3 RB1 RC17 LA242 RB4 RB1 RC17 LA243 RB5 RB1 RC17 LA244 RB18 RB1 RC17 LA245 RB43 RB1 RC17 LA246 RA3 RB1 RC17 LA247 RA34 RB1 RC17 LA248 RA57 RB1 RC17 LA249 RB3 RA74 RC17 LA250 RB4 RA74 RC17 LA251 RB5 RA74 RC17 LA252 RB18 RA74 RC17 LA253 RB43 RA74 RC17 LA254 RA3 RA74 RC17 LA255 RA34 RA74 RC17 LA256 RA57 RA74 RC17 LA257 RB3 H RC20 LA258 RB4 H RC20 LA259 RB5 H RC20 LA260 RB18 H RC20 LA261 RB43 H RC20 LA262 RA3 H RC20 LA263 RA34 H RC20 LA264 RA57 H RC20 LA265 RB3 F RC20 LA266 RB4 F RC20 LA267 RB5 F RC20 LA268 RB18 F RC20 LA269 RB43 F RC20 LA270 RA3 F RC20 LA271 RA34 F RC20 LA272 RA57 F RC20 LA273 RB3 RB1 RC20 LA274 RB4 RB1 RC20 LA275 RB5 RB1 RC20 LA276 RB18 RB1 RC20 LA277 RB43 RB1 RC20 LA278 RA3 RB1 RC20 LA279 RA34 RB1 RC20 LA280 RA57 RB1 RC20 LA281 RB3 RA74 RC20 LA282 RB4 RA74 RC20 LA283 RB5 RA74 RC20 LA284 RB18 RA74 RC20 LA285 RB43 RA74 RC20 LA286 RA3 RA74 RC20 LA287 RA34 RA74 RC20 LA288 RA57 RA74 RC20 LA289 RB3 H RC24 LA290 RB4 H RC24 LA291 RB5 H RC24 LA292 RB18 H RC24 LA293 RB43 H RC24 LA294 RA3 H RC24 LA295 RA34 H RC24 LA296 RA57 H RC24 LA297 RB3 F RC24 LA298 RB4 F RC24 LA299 RB5 F RC24 LA300 RB18 F RC24 LA301 RB43 F RC24 LA302 RA3 F RC24 LA303 RA34 F RC24 LA304 RA57 F RC24 LA305 RB3 RB1 RC24 LA306 RB4 RB1 RC24 LA307 RB5 RB1 RC24 LA308 RB18 RB1 RC24 LA309 RB43 RB1 RC24 LA310 RA3 RB1 RC24 LA311 RA34 RB1 RC24 LA312 RA57 RB1 RC24 LA313 RB3 RA74 RC24 LA314 RB4 RA74 RC24 LA315 RB5 RA74 RC24 LA316 RB18 RA74 RC24 LA317 RB43 RA74 RC24 LA318 RA3 RA74 RC24 LA319 RA34 RA74 RC24 LA320 RA57 RA74 RC24 LA321 RB3 H RC27 LA322 RB4 H RC27 LA323 RB5 H RC27 LA324 RB18 H RC27 LA325 RB43 H RC27 LA326 RA3 H RC27 LA327 RA34 H RC27 LA328 RA57 H RC27 LA329 RB3 F RC27 LA330 RB4 F RC27 LA331 RB5 F RC27 LA332 RB18 F RC27 LA333 RB43 F RC27 LA334 RA3 F RC27 LA335 RA34 F RC27 LA336 RA57 F RC27 LA337 RB3 RB1 RC27 LA338 RB4 RB1 RC27 LA339 RB5 RB1 RC27 LA340 RB18 RB1 RC27 LA341 RB43 RB1 RC27 LA342 RA3 RB1 RC27 LA343 RA34 RB1 RC27 LA344 RA57 RB1 RC27 LA345 RB3 RA74 RC27 LA346 RB4 RA74 RC27 LA347 RB5 RA74 RC27 LA348 RB18 RA74 RC27 LA349 RB43 RA74 RC27 LA350 RA3 RA74 RC27 LA351 RA34 RA74 RC27 LA352 RA57 RA74 RC27 LA353 RB3 H RC31 LA354 RB4 H RC31 LA355 RB5 H RC31 LA356 RB18 H RC31 LA357 RB43 H RC31 LA358 RA3 H RC31 LA359 RA34 H RC31 LA360 RA57 H RC31 LA361 RB3 F RC31 LA362 RB4 F RC31 LA363 RB5 F RC31 LA364 RB18 F RC31 LA365 RB43 F RC31 LA366 RA3 F RC31 LA367 RA34 F RC31 LA368 RA57 F RC31 LA369 RB3 RB1 RC31 LA370 RB4 RB1 RC31 LA371 RB5 RB1 RC31 LA372 RB18 RB1 RC31 LA373 RB43 RB1 RC31 LA374 RA3 RB1 RC31 LA375 RA34 RB1 RC31 LA376 RA57 RB1 RC31 LA377 RB3 RA74 RC31 LA378 RB4 RA74 RC31 LA379 RB5 RA74 RC31 LA380 RB18 RA74 RC31 LA381 RB43 RA74 RC31 LA382 RA3 RA74 RC31 LA383 RA34 RA74 RC31 LA384 RA57 RA74 RC31 LA385 RB3 H RC34 LA386 RB4 H RC34 LA387 RB5 H RC34 LA388 RB18 H RC34 LA389 RB43 H RC34 LA390 RA3 H RC34 LA391 RA34 H RC34 LA392 RA57 H RC34 LA393 RB3 F RC34 LA394 RB4 F RC34 LA395 RB5 F RC34 LA396 RB18 F RC34 LA397 RB43 F RC34 LA398 RA3 F RC34 LA399 RA34 F RC34 LA400 RA57 F RC34 LA401 RB3 RB1 RC34 LA402 RB4 RB1 RC34 LA403 RB5 RB1 RC34 LA404 RB18 RB1 RC34 LA405 RB43 RB1 RC34 LA406 RA3 RB1 RC34 LA407 RA34 RB1 RC34 LA408 RA57 RB1 RC34 LA409 RB3 RA74 RC34 LA410 RB4 RA74 RC34 LA411 RB5 RA74 RC34 LA412 RB18 RA74 RC34 LA413 RB43 RA74 RC34 LA414 RA3 RA74 RC34 LA415 RA34 RA74 RC34 LA416 RA57 RA74 RC34 LA417 RB3 H RC38 LA418 RB4 H RC38 LA419 RB5 H RC38 LA420 RB18 H RC38 LA421 RB43 H RC38 LA422 RA3 H RC38 LA423 RA34 H RC38 LA424 RA57 H RC38 LA425 RB3 F RC38 LA426 RB4 F RC38 LA427 RB5 F RC38 LA428 RB18 F RC38 LA429 RB43 F RC38 LA430 RA3 F RC38 LA431 RA34 F RC38 LA432 RA57 F RC38 LA433 RB3 RB1 RC38 LA434 RB4 RB1 RC38 LA435 RB5 RB1 RC38 LA436 RB18 RB1 RC38 LA437 RB43 RB1 RC38 LA438 RA3 RB1 RC38 LA439 RA34 RB1 RC38 LA440 RA57 RB1 RC38 LA441 RB3 RA74 RC38 LA442 RB4 RA74 RC38 LA443 RB5 RA74 RC38 LA444 RB18 RA74 RC38 LA445 RB43 RA74 RC38 LA446 RA3 RA74 RC38 LA447 RA34 RA74 RC38 LA448 RA57 RA74 RC38,
LA449 through LA896 based on a structure of Formula II
Figure US20240025934A1-20240125-C00245
in which R1, R2, and G are defined as:
Ligand R1 R2 G LA449 H RB3 RC2 LA450 H RB4 RC2 LA451 H RB5 RC2 LA452 H RB18 RC2 LA453 H RB43 RC2 LA454 H RA3 RC2 LA455 H RA34 RC2 LA456 H RA57 RC2 LA457 F RB3 RC2 LA458 F RB4 RC2 LA459 F RB5 RC2 LA460 F RB18 RC2 LA461 F RB43 RC2 LA462 F RA3 RC2 LA463 F RA34 RC2 LA464 F RA57 RC2 LA465 RB1 RB3 RC2 LA466 RB1 RB4 RC2 LA467 RB1 RB5 RC2 LA468 RB1 RB18 RC2 LA469 RB1 RB43 RC2 LA470 RB1 RA3 RC2 LA471 RB1 RA34 RC2 LA472 RB1 RA57 RC2 LA473 RA74 RB3 RC2 LA474 RA74 RB4 RC2 LA475 RA74 RB5 RC2 LA476 RA74 RB18 RC2 LA477 RA74 RB43 RC2 LA478 RA74 RA3 RC2 LA479 RA74 RA34 RC2 LA480 RA74 RA57 RC2 LA481 H RB3 RC5 LA482 H RB4 RC5 LA483 H RB5 RC5 LA484 H RB18 RC5 LA485 H RB43 RC5 LA486 H RA3 RC5 LA487 H RA34 RC5 LA488 H RA57 RC5 LA489 F RB3 RC5 LA490 F RB4 RC5 LA491 F RB5 RC5 LA492 F RB18 RC5 LA493 F RB43 RC5 LA494 F RA3 RC5 LA495 F RA34 RC5 LA496 F RA57 RC5 LA497 RB1 RB3 RC5 LA498 RB1 RB4 RC5 LA499 RB1 RB5 RC5 LA500 RB1 RB18 RC5 LA501 RB1 RB43 RC5 LA502 RB1 RA3 RC5 LA503 RB1 RA34 RC5 LA504 RB1 RA57 RC5 LA505 RA74 RB3 RC5 LA506 RA74 RB4 RC5 LA507 RA74 RB5 RC5 LA508 RA74 RB18 RC5 LA509 RA74 RB43 RC5 LA510 RA74 RA3 RC5 LA511 RA74 RA34 RC5 LA512 RA74 RA57 RC5 LA513 H RB3 RC6 LA514 H RB4 RC6 LA515 H RB5 RC6 LA516 H RB18 RC6 LA517 H RB43 RC6 LA518 H RA3 RC6 LA519 H RA34 RC6 LA520 H RA57 RC6 LA521 F RB3 RC6 LA522 F RB4 RC6 LA523 F RB5 RC6 LA524 F RB18 RC6 LA525 F RB43 RC6 LA526 F RA3 RC6 LA527 F RA34 RC6 LA528 F RA57 RC6 LA529 RB1 RB3 RC6 LA530 RB1 RB4 RC6 LA531 RB1 RB5 RC6 LA532 RB1 RB18 RC6 LA533 RB1 RB43 RC6 LA534 RB1 RA3 RC6 LA535 RB1 RA34 RC6 LA536 RB1 RA57 RC6 LA537 RA74 RB3 RC6 LA538 RA74 RB4 RC6 LA539 RA74 RB5 RC6 LA540 RA74 RB18 RC6 LA541 RA74 RB43 RC6 LA542 RA74 RA3 RC6 LA543 RA74 RA34 RC6 LA544 RA74 RA57 RC6 LA545 H RB3 RC7 LA546 H RB4 RC7 LA547 H RB5 RC7 LA548 H RB18 RC7 LA549 H RB43 RC7 LA550 H RA3 RC7 LA551 H RA34 RC7 LA552 H RA57 RC7 LA553 F RB3 RC7 LA554 F RB4 RC7 LA555 F RB5 RC7 LA556 F RB18 RC7 LA557 F RB43 RC7 LA558 F RA3 RC7 LA559 F RA34 RC7 LA560 F RA57 RC7 LA561 RB1 RB3 RC7 LA562 RB1 RB4 RC7 LA563 RB1 RB5 RC7 LA564 RB1 RB18 RC7 LA565 RB1 RB43 RC7 LA566 RB1 RA3 RC7 LA567 RB1 RA34 RC7 LA568 RB1 RA57 RC7 LA569 RA74 RB3 RC7 LA570 RA74 RB4 RC7 LA571 RA74 RB5 RC7 LA572 RA74 RB18 RC7 LA573 RA74 RB43 RC7 LA574 RA74 RA3 RC7 LA575 RA74 RA34 RC7 LA576 RA74 RA57 RC7 LA577 H RB3 RC10 LA578 H RB4 RC10 LA579 H RB5 RC10 LA580 H RB18 RC10 LA581 H RB43 RC10 LA582 H RA3 RC10 LA583 H RA34 RC10 LA584 H RA57 RC10 LA585 F RB3 RC10 LA586 F RB4 RC10 LA587 F RB5 RC10 LA588 F RB18 RC10 LA589 F RB43 RC10 LA590 F RA3 RC10 LA591 F RA34 RC10 LA592 F RA57 RC10 LA593 RB1 RB3 RC10 LA594 RB1 RB4 RC10 LA595 RB1 RB5 RC10 LA596 RB1 RB18 RC10 LA597 RB1 RB43 RC10 LA598 RB1 RA3 RC10 LA599 RB1 RA34 RC10 LA600 RB1 RA57 RC10 LA601 RA74 RB3 RC10 LA602 RA74 RB4 RC10 LA603 RA74 RB5 RC10 LA604 RA74 RB18 RC10 LA605 RA74 RB43 RC10 LA606 RA74 RA3 RC10 LA607 RA74 RA34 RC10 LA608 RA74 RA57 RC10 LA609 H RB3 RC11 LA610 H RB4 RC11 LA611 H RB5 RC11 LA612 H RB18 RC11 LA613 H RB43 RC11 LA614 H RA3 RC11 LA615 H RA34 RC11 LA616 H RA57 RC11 LA617 F RB3 RC11 LA618 F RB4 RC11 LA619 F RB5 RC11 LA620 F RB18 RC11 LA621 F RB43 RC11 LA622 F RA3 RC11 LA623 F RA34 RC11 LA624 F RA57 RC11 LA625 RB1 RB3 RC11 LA626 RB1 RB4 RC11 LA627 RB1 RB5 RC11 LA628 RB1 RB18 RC11 LA629 RB1 RB43 RC11 LA630 RB1 RA3 RC11 LA631 RB1 RA34 RC11 LA632 RB1 RA57 RC11 LA633 RA74 RB3 RC11 LA634 RA74 RB4 RC11 LA635 RA74 RB5 RC11 LA636 RA74 RB18 RC11 LA637 RA74 RB43 RC11 LA638 RA74 RA3 RC11 LA639 RA74 RA34 RC11 LA640 RA74 RA57 RC11 LA641 H RB3 RC13 LA642 H RB4 RC13 LA643 H RB5 RC13 LA644 H RB18 RC13 LA645 H RB43 RC13 LA646 H RA3 RC13 LA647 H RA34 RC13 LA648 H RA57 RC13 LA649 F RB3 RC13 LA650 F RB4 RC13 LA651 F RB5 RC13 LA652 F RB18 RC13 LA653 F RB43 RC13 LA654 F RA3 RC13 LA655 F RA34 RC13 LA656 F RA57 RC13 LA657 RB1 RB3 RC13 LA658 RB1 RB4 RC13 LA659 RB1 RB5 RC13 LA660 RB1 RB18 RC13 LA661 RB1 RB43 RC13 LA662 RB1 RA3 RC13 LA663 RB1 RA34 RC13 LA664 RB1 RA57 RC13 LA665 RA74 RB3 RC13 LA666 RA74 RB4 RC13 LA667 RA74 RB5 RC13 LA668 RA74 RB18 RC13 LA669 RA74 RB43 RC13 LA670 RA74 RA3 RC13 LA671 RA74 RA34 RC13 LA672 RA74 RA57 RC13 LA673 H RB3 RC17 LA674 H RB4 RC17 LA675 H RB5 RC17 LA676 H RB18 RC17 LA677 H RB43 RC17 LA678 H RA3 RC17 LA679 H RA34 RC17 LA680 H RA57 RC17 LA681 F RB3 RC17 LA682 F RB4 RC17 LA683 F RB5 RC17 LA684 F RB18 RC17 LA685 F RB43 RC17 LA686 F RA3 RC17 LA687 F RA34 RC17 LA688 F RA57 RC17 LA689 RB1 RB3 RC17 LA690 RB1 RB4 RC17 LA691 RB1 RB5 RC17 LA692 RB1 RB18 RC17 LA693 RB1 RB43 RC17 LA694 RB1 RA3 RC17 LA695 RB1 RA34 RC17 LA696 RB1 RA57 RC17 LA697 RA74 RB3 RC17 LA698 RA74 RB4 RC17 LA699 RA74 RB5 RC17 LA700 RA74 RB18 RC17 LA701 RA74 RB43 RC17 LA702 RA74 RA3 RC17 LA703 RA74 RA34 RC17 LA704 RA74 RA57 RC17 LA705 H RB3 RC20 LA706 H RB4 RC20 LA707 H RB5 RC20 LA708 H RB18 RC20 LA709 H RB43 RC20 LA710 H RA3 RC20 LA711 H RA34 RC20 LA712 H RA57 RC20 LA713 F RB3 RC20 LA714 F RB4 RC20 LA715 F RB5 RC20 LA716 F RB18 RC20 LA717 F RB43 RC20 LA718 F RA3 RC20 LA719 F RA34 RC20 LA720 F RA57 RC20 LA721 RB1 RB3 RC20 LA722 RB1 RB4 RC20 LA723 RB1 RB5 RC20 LA724 RB1 RB18 RC20 LA725 RB1 RB43 RC20 LA726 RB1 RA3 RC20 LA727 RB1 RA34 RC20 LA728 RB1 RA57 RC20 LA729 RA74 RB3 RC20 LA730 RA74 RB4 RC20 LA731 RA74 RB5 RC20 LA732 RA74 RB18 RC20 LA733 RA74 RB43 RC20 LA734 RA74 RA3 RC20 LA735 RA74 RA34 RC20 LA736 RA74 RA57 RC20 LA737 H RB3 RC24 LA738 H RB4 RC24 LA739 H RB5 RC24 LA740 H RB18 RC24 LA741 H RB43 RC24 LA742 H RA3 RC24 LA743 H RA34 RC24 LA744 H RA57 RC24 LA745 F RB3 RC24 LA746 F RB4 RC24 LA747 F RB5 RC24 LA748 F RB18 RC24 LA749 F RB43 RC24 LA750 F RA3 RC24 LA751 F RA34 RC24 LA752 F RA57 RC24 LA753 RB1 RB3 RC24 LA754 RB1 RB4 RC24 LA755 RB1 RB5 RC24 LA756 RB1 RB18 RC24 LA757 RB1 RB43 RC24 LA758 RB1 RA3 RC24 LA759 RB1 RA34 RC24 LA760 RB1 RA57 RC24 LA761 RA74 RB3 RC24 LA762 RA74 RB4 RC24 LA763 RA74 RB5 RC24 LA764 RA74 RB18 RC24 LA765 RA74 RB43 RC24 LA766 RA74 RA3 RC24 LA767 RA74 RA34 RC24 LA768 RA74 RA57 RC24 LA769 H RB3 RC27 LA770 H RB4 RC27 LA771 H RB5 RC27 LA772 H RB18 RC27 LA773 H RB43 RC27 LA774 H RA3 RC27 LA775 H RA34 RC27 LA776 H RA57 RC27 LA777 F RB3 RC27 LA778 F RB4 RC27 LA779 F RB5 RC27 LA780 F RB18 RC27 LA781 F RB43 RC27 LA782 F RA3 RC27 LA783 F RA34 RC27 LA784 F RA57 RC27 LA785 RB1 RB3 RC27 LA786 RB1 RB4 RC27 LA787 RB1 RB5 RC27 LA788 RB1 RB18 RC27 LA789 RB1 RB43 RC27 LA790 RB1 RA3 RC27 LA791 RB1 RA34 RC27 LA792 RB1 RA57 RC27 LA793 RA74 RB3 RC27 LA794 RA74 RB4 RC27 LA795 RA74 RB5 RC27 LA796 RA74 RB18 RC27 LA797 RA74 RB43 RC27 LA798 RA74 RA3 RC27 LA799 RA74 RA34 RC27 LA800 RA74 RA57 RC27 LA801 H RB3 RC31 LA802 H RB4 RC31 LA803 H RB5 RC31 LA804 H RB18 RC31 LA805 H RB43 RC31 LA806 H RA3 RC31 LA807 H RA34 RC31 LA808 H RA57 RC31 LA809 F RB3 RC31 LA810 F RB4 RC31 LA811 F RB5 RC31 LA812 F RB18 RC31 LA813 F RB43 RC31 LA814 F RA3 RC31 LA815 F RA34 RC31 LA816 F RA57 RC31 LA817 RB1 RB3 RC31 LA818 RB1 RB4 RC31 LA819 RB1 RB5 RC31 LA820 RB1 RB18 RC31 LA821 RB1 RB43 RC31 LA822 RB1 RA3 RC31 LA823 RB1 RA34 RC31 LA824 RB1 RA57 RC31 LA825 RA74 RB3 RC31 LA826 RA74 RB4 RC31 LA827 RA74 RB5 RC31 LA828 RA74 RB18 RC31 LA829 RA74 RB43 RC31 LA830 RA74 RA3 RC31 LA831 RA74 RA34 RC31 LA832 RA74 RA57 RC31 LA833 H RB3 RC34 LA834 H RB4 RC34 LA835 H RB5 RC34 LA836 H RB18 RC34 LA837 H RB43 RC34 LA838 H RA3 RC34 LA839 H RA34 RC34 LA840 H RA57 RC34 LA841 F RB3 RC34 LA842 F RB4 RC34 LA843 F RB5 RC34 LA844 F RB18 RC34 LA845 F RB43 RC34 LA846 F RA3 RC34 LA847 F RA34 RC34 LA848 F RA57 RC34 LA849 RB1 RB3 RC34 LA850 RB1 RB4 RC34 LA851 RB1 RB5 RC34 LA852 RB1 RB18 RC34 LA853 RB1 RB43 RC34 LA854 RB1 RA3 RC34 LA855 RB1 RA34 RC34 LA856 RB1 RA57 RC34 LA857 RA74 RB3 RC34 LA858 RA74 RB4 RC34 LA859 RA74 RB5 RC34 LA860 RA74 RB18 RC34 LA861 RA74 RB43 RC34 LA862 RA74 RA3 RC34 LA863 RA74 RA34 RC34 LA864 RA74 RA57 RC34 LA865 H RB3 RC38 LA866 H RB4 RC38 LA867 H RB5 RC38 LA868 H RB18 RC38 LA869 H RB43 RC38 LA870 H RA3 RC38 LA871 H RA34 RC38 LA872 H RA57 RC38 LA873 F RB3 RC38 LA874 F RB4 RC38 LA875 F RB5 RC38 LA876 F RB18 RC38 LA877 F RB43 RC38 LA878 F RA3 RC38 LA879 F RA34 RC38 LA880 F RA57 RC38 LA881 RB1 RB3 RC38 LA882 RB1 RB4 RC38 LA883 RB1 RB5 RC38 LA884 RB1 RB18 RC38 LA885 RB1 RB43 RC38 LA886 RB1 RA3 RC38 LA887 RB1 RA34 RC38 LA888 RB1 RA57 RC38 LA889 RA74 RB3 RC38 LA890 RA74 RB4 RC38 LA891 RA74 RB5 RC38 LA892 RA74 RB18 RC38 LA893 RA74 RB43 RC38 LA894 RA74 RA3 RC38 LA895 RA74 RA34 RC38 LA896 RA74 RA57 RC38,
LA897 through LA1344 based on a structure of Formula II
Figure US20240025934A1-20240125-C00246
in which R1, R2, and G are defined as:
Ligand R1 R2 G LA897 RB3 RB3 RC2 LA898 RB4 RB4 RC2 LA899 RB5 RB5 RC2 LA900 RB18 RB18 RC2 LA901 RB43 RB43 RC2 LA902 RA3 RA3 RC2 LA903 RA34 RA34 RC2 LA904 RA57 RA57 RC2 LA905 RB3 RB7 RC2 LA906 RB4 RB7 RC2 LA907 RB5 RB7 RC2 LA908 RB18 RB7 RC2 LA909 RB43 RB7 RC2 LA910 RA3 RB7 RC2 LA911 RA34 RB7 RC2 LA912 RA57 RB7 RC2 LA913 RB3 RA3 RC2 LA914 RB4 RA3 RC2 LA915 RB5 RA3 RC2 LA916 RB18 RA3 RC2 LA917 RB43 RA3 RC2 LA918 RA3 RA3 RC2 LA919 RA34 RA3 RC2 LA920 RA57 RA3 RC2 LA921 RB3 RA34 RC2 LA922 RB4 RA34 RC2 LA923 RB5 RA34 RC2 LA924 RB18 RA34 RC2 LA925 RB43 RA34 RC2 LA926 RA3 RA34 RC2 LA927 RA34 RA34 RC2 LA928 RA57 RA34 RC2 LA929 RB3 RB3 RC5 LA930 RB4 RB4 RC5 LA931 RB5 RB5 RC5 LA932 RB18 RB18 RC5 LA933 RB43 RB43 RC5 LA934 RA3 RA3 RC5 LA935 RA34 RA34 RC5 LA936 RA57 RA57 RC5 LA937 RB3 RB7 RC5 LA938 RB4 RB7 RC5 LA939 RB5 RB7 RC5 LA940 RB18 RB7 RC5 LA941 RB43 RB7 RC5 LA942 RA3 RB7 RC5 LA943 RA34 RB7 RC5 LA944 RA57 RB7 RC5 LA945 RB3 RA3 RC5 LA946 RB4 RA3 RC5 LA947 RB5 RA3 RC5 LA948 RB18 RA3 RC5 LA949 RB43 RA3 RC5 LA950 RA3 RA3 RC5 LA951 RA34 RA3 RC5 LA952 RA57 RA3 RC5 LA953 RB3 RA34 RC5 LA954 RB4 RA34 RC5 LA955 RB5 RA34 RC5 LA956 RB18 RA34 RC5 LA957 RB43 RA34 RC5 LA958 RA3 RA34 RC5 LA959 RA34 RA34 RC5 LA960 RA57 RA34 RC5 LA961 RB3 RB3 RC6 LA962 RB4 RB4 RC6 LA963 RB5 RB5 RC6 LA964 RB18 RB18 RC6 LA965 RB43 RB43 RC6 LA966 RA3 RA3 RC6 LA967 RA34 RA34 RC6 LA968 RA57 RA57 RC6 LA969 RB3 RB7 RC6 LA970 RB4 RB7 RC6 LA971 RB5 RB7 RC6 LA972 RB18 RB7 RC6 LA973 RB43 RB7 RC6 LA974 RA3 RB7 RC6 LA975 RA34 RB7 RC6 LA976 RA57 RB7 RC6 LA977 RB3 RA3 RC6 LA978 RB4 RA3 RC6 LA979 RB5 RA3 RC6 LA980 RB18 RA3 RC6 LA981 RB43 RA3 RC6 LA982 RA3 RA3 RC6 LA983 RA34 RA3 RC6 LA984 RA57 RA3 RC6 LA985 RB3 RA34 RC6 LA986 RB4 RA34 RC6 LA987 RB5 RA34 RC6 LA988 RB18 RA34 RC6 LA989 RB43 RA34 RC6 LA990 RA3 RA34 RC6 LA991 RA34 RA34 RC6 LA992 RA57 RA34 RC6 LA993 RB3 RB3 RC7 LA994 RB4 RB4 RC7 LA995 RB5 RB5 RC7 LA996 RB18 RB18 RC7 LA997 RB43 RB43 RC7 LA998 RA3 RA3 RC7 LA999 RA34 RA34 RC7 LA1000 RA57 RA57 RC7 LA1001 RB3 RB7 RC7 LA1002 RB4 RB7 RC7 LA1003 RB5 RB7 RC7 LA1004 RB18 RB7 RC7 LA1005 RB43 RB7 RC7 LA1006 RA3 RB7 RC7 LA1007 RA34 RB7 RC7 LA1008 RA57 RB7 RC7 LA1009 RB3 RA3 RC7 LA1010 RB4 RA3 RC7 LA1011 RB5 RA3 RC7 LA1012 RB18 RA3 RC7 LA1013 RB43 RA3 RC7 LA1014 RA3 RA3 RC7 LA1015 RA34 RA3 RC7 LA1016 RA57 RA3 RC7 LA1017 RB3 RA34 RC7 LA1018 RB4 RA34 RC7 LA1019 RB5 RA34 RC7 LA1020 RB18 RA34 RC7 LA1021 RB43 RA34 RC7 LA1022 RA3 RA34 RC7 LA1023 RA34 RA34 RC7 LA1024 RA57 RA34 RC7 LA1025 RB3 RB3 RC10 LA1026 RB4 RB4 RC10 LA1027 RB5 RB5 RC10 LA1028 RB18 RB18 RC10 LA1029 RB43 RB43 RC10 LA1030 RA3 RA3 RC10 LA1031 RA34 RA34 RC10 LA1032 RA57 RA57 RC10 LA1033 RB3 RB7 RC10 LA1034 RB4 RB7 RC10 LA1035 RB5 RB7 RC10 LA1036 RB18 RB7 RC10 LA1037 RB43 RB7 RC10 LA1038 RA3 RB7 RC10 LA1039 RA34 RB7 RC10 LA1040 RA57 RB7 RC10 LA1041 RB3 RA3 RC10 LA1042 RB4 RA3 RC10 LA1043 RB5 RA3 RC10 LA1044 RB18 RA3 RC10 LA1045 RB43 RA3 RC10 LA1046 RA3 RA3 RC10 LA1047 RA34 RA3 RC10 LA1048 RA57 RA3 RC10 LA1049 RB3 RA34 RC10 LA1050 RB4 RA34 RC10 LA1051 RB5 RA34 RC10 LA1052 RB18 RA34 RC10 LA1053 RB43 RA34 RC10 LA1054 RA3 RA34 RC10 LA1055 RA34 RA34 RC10 LA1056 RA57 RA34 RC10 LA1057 RB3 RB3 RC11 LA1058 RB4 RB4 RC11 LA1059 RB5 RB5 RC11 LA1060 RB18 RB18 RC11 LA1061 RB43 RB43 RC11 LA1062 RA3 RA3 RC11 LA1063 RA34 RA34 RC11 LA1064 RA57 RA57 RC11 LA1065 RB3 RB7 RC11 LA1066 RB4 RB7 RC11 LA1067 RB5 RB7 RC11 LA1068 RB18 RB7 RC11 LA1069 RB43 RB7 RC11 LA1070 RA3 RB7 RC11 LA1071 RA34 RB7 RC11 LA1072 RA57 RB7 RC11 LA1073 RB3 RA3 RC11 LA1074 RB4 RA3 RC11 LA1075 RB5 RA3 RC11 LA1076 RB18 RA3 RC11 LA1077 RB43 RA3 RC11 LA1078 RA3 RA3 RC11 LA1079 RA34 RA3 RC11 LA1080 RA57 RA3 RC11 LA1081 RB3 RA34 RC11 LA1082 RB4 RA34 RC11 LA1083 RB5 RA34 RC11 LA1084 RB18 RA34 RC11 LA1085 RB43 RA34 RC11 LA1086 RA3 RA34 RC11 LA1087 RA34 RA34 RC11 LA1088 RA57 RA34 RC11 LA1089 RB3 RB3 RC13 LA1090 RB4 RB4 RC13 LA1091 RB5 RB5 RC13 LA1092 RB18 RB18 RC13 LA1093 RB43 RB43 RC13 LA1094 RA3 RA3 RC13 LA1095 RA34 RA34 RC13 LA1096 RA57 RA57 RC13 LA1097 RB3 RB7 RC13 LA1098 RB4 RB7 RC13 LA1099 RB5 RB7 RC13 LA1100 RB18 RB7 RC13 LA1101 RB43 RB7 RC13 LA1102 RA3 RB7 RC13 LA1103 RA34 RB7 RC13 LA1104 RA57 RB7 RC13 LA1105 RB3 RA3 RC13 LA1106 RB4 RA3 RC13 LA1107 RB5 RA3 RC13 LA1108 RB18 RA3 RC13 LA1109 RB43 RA3 RC13 LA1110 RA3 RA3 RC13 LA1111 RA34 RA3 RC13 LA1112 RA57 RA3 RC13 LA1113 RB3 RA34 RC13 LA1114 RB4 RA34 RC13 LA1115 RB5 RA34 RC13 LA1116 RB18 RA34 RC13 LA1117 RB43 RA34 RC13 LA1118 RA3 RA34 RC13 LA1119 RA34 RA34 RC13 LA1120 RA57 RA34 RC13 LA1121 RB3 RB3 RC17 LA1122 RB4 RB4 RC17 LA1123 RB5 RB5 RC17 LA1124 RB18 RB18 RC17 LA1125 RB43 RB43 RC17 LA1126 RA3 RA3 RC17 LA1127 RA34 RA34 RC17 LA1128 RA57 RA57 RC17 LA1129 RB3 RB7 RC17 LA1130 RB4 RB7 RC17 LA1131 RB5 RB7 RC17 LA1132 RB18 RB7 RC17 LA1133 RB43 RB7 RC17 LA1134 RA3 RB7 RC17 LA1135 RA34 RB7 RC17 LA1136 RA57 RB7 RC17 LA1137 RB3 RA3 RC17 LA1138 RB4 RA3 RC17 LA1139 RB5 RA3 RC17 LA1140 RB18 RA3 RC17 LA1141 RB43 RA3 RC17 LA1142 RA3 RA3 RC17 LA1143 RA34 RA3 RC17 LA1144 RA57 RA3 RC17 LA1145 RB3 RA34 RC17 LA1146 RB4 RA34 RC17 LA1147 RB5 RA34 RC17 LA1148 RB18 RA34 RC17 LA1149 RB43 RA34 RC17 LA1150 RA3 RA34 RC17 LA1151 RA34 RA34 RC17 LA1152 RA57 RA34 RC17 LA1153 RB3 RB3 RC20 LA1154 RB4 RB4 RC20 LA1155 RB5 RB5 RC20 LA1156 RB18 RB18 RC20 LA1157 RB43 RB43 RC20 LA1158 RA3 RA3 RC20 LA1159 RA34 RA34 RC20 LA1160 RA57 RA57 RC20 LA1161 RB3 RB7 RC20 LA1162 RB4 RB7 RC20 LA1163 RB5 RB7 RC20 LA1164 RB18 RB7 RC20 LA1165 RB43 RB7 RC20 LA1166 RA3 RB7 RC20 LA1167 RA34 RB7 RC20 LA1168 RA57 RB7 RC20 LA1169 RB3 RA3 RC20 LA1170 RB4 RA3 RC20 LA1171 RB5 RA3 RC20 LA1172 RB18 RA3 RC20 LA1173 RB43 RA3 RC20 LA1174 RA3 RA3 RC20 LA1175 RA34 RA3 RC20 LA1176 RA57 RA3 RC20 LA1177 RB3 RA34 RC20 LA1178 RB4 RA34 RC20 LA1179 RB5 RA34 RC20 LA1180 RB18 RA34 RC20 LA1181 RB43 RA34 RC20 LA1182 RA3 RA34 RC20 LA1183 RA34 RA34 RC20 LA1184 RA57 RA34 RC20 LA1185 RB3 RB3 RC24 LA1186 RB4 RB4 RC24 LA1187 RB5 RB5 RC24 LA1188 RB18 RB18 RC24 LA1189 RB43 RB43 RC24 LA1190 RA3 RA3 RC24 LA1191 RA34 RA34 RC24 LA1192 RA57 RA57 RC24 LA1193 RB3 RB7 RC24 LA1194 RB4 RB7 RC24 LA1195 RB5 RB7 RC24 LA1196 RB18 RB7 RC24 LA1197 RB43 RB7 RC24 LA1198 RA3 RB7 RC24 LA1199 RA34 RB7 RC24 LA1200 RA57 RB7 RC24 LA1201 RB3 RA3 RC24 LA1202 RB4 RA3 RC24 LA1203 RB5 RA3 RC24 LA1204 RB18 RA3 RC24 LA1205 RB43 RA3 RC24 LA1206 RA3 RA3 RC24 LA1207 RA34 RA3 RC24 LA1208 RA57 RA3 RC24 LA1209 RB3 RA34 RC24 LA1210 RB4 RA34 RC24 LA1211 RB5 RA34 RC24 LA1212 RB18 RA34 RC24 LA1213 RB43 RA34 RC24 LA1214 RA3 RA34 RC24 LA1215 RA34 RA34 RC24 LA1216 RA57 RA34 RC24 LA1217 RB3 RB3 RC27 LA1218 RB4 RB4 RC27 LA1219 RB5 RB5 RC27 LA1220 RB18 RB18 RC27 LA1221 RB43 RB43 RC27 LA1222 RA3 RA3 RC27 LA1223 RA34 RA34 RC27 LA1224 RA57 RA57 RC27 LA1225 RB3 RB7 RC27 LA1226 RB4 RB7 RC27 LA1227 RB5 RB7 RC27 LA1228 RB18 RB7 RC27 LA1229 RB43 RB7 RC27 LA1230 RA3 RB7 RC27 LA1231 RA34 RB7 RC27 LA1232 RA57 RB7 RC27 LA1233 RB3 RA3 RC27 LA1234 RB4 RA3 RC27 LA1235 RB5 RA3 RC27 LA1236 RB18 RA3 RC27 LA1237 RB43 RA3 RC27 LA1238 RA3 RA3 RC27 LA1239 RA34 RA3 RC27 LA1240 RA57 RA3 RC27 LA1241 RB3 RA34 RC27 LA1242 RB4 RA34 RC27 LA1243 RB5 RA34 RC27 LA1244 RB18 RA34 RC27 LA1245 RB43 RA34 RC27 LA1246 RA3 RA34 RC27 LA1247 RA34 RA34 RC27 LA1248 RA57 RA34 RC27 LA1249 RB3 RB3 RC31 LA1250 RB4 RB4 RC31 LA1251 RB5 RB5 RC31 LA1252 RB18 RB18 RC31 LA1253 RB43 RB43 RC31 LA1254 RA3 RA3 RC31 LA1255 RA34 RA34 RC31 LA1256 RA57 RA57 RC31 LA1257 RB3 RB7 RC31 LA1258 RB4 RB7 RC31 LA1259 RB5 RB7 RC31 LA1260 RB18 RB7 RC31 LA1261 RB43 RB7 RC31 LA1262 RA3 RB7 RC31 LA1263 RA34 RB7 RC31 LA1264 RA57 RB7 RC31 LA1265 RB3 RA3 RC31 LA1266 RB4 RA3 RC31 LA1267 RB5 RA3 RC31 LA1268 RB18 RA3 RC31 LA1269 RB43 RA3 RC31 LA1270 RA3 RA3 RC31 LA1271 RA34 RA3 RC31 LA1272 RA57 RA3 RC31 LA1273 RB3 RA34 RC31 LA1274 RB4 RA34 RC31 LA1275 RB5 RA34 RC31 LA1276 RB18 RA34 RC31 LA1277 RB43 RA34 RC31 LA1278 RA3 RA34 RC31 LA1279 RA34 RA34 RC31 LA1280 RA57 RA34 RC31 LA1281 RB3 RB3 RC34 LA1282 RB4 RB4 RC34 LA1283 RB5 RB5 RC34 LA1284 RB18 RB18 RC34 LA1285 RB43 RB43 RC34 LA1286 RA3 RA3 RC34 LA1287 RA34 RA34 RC34 LA1288 RA57 RA57 RC34 LA1289 RB3 RB7 RC34 LA1290 RB4 RB7 RC34 LA1291 RB5 RB7 RC34 LA1292 RB18 RB7 RC34 LA1293 RB43 RB7 RC34 LA1294 RA3 RB7 RC34 LA1295 RA34 RB7 RC34 LA1296 RA57 RB7 RC34 LA1297 RB3 RA3 RC34 LA1298 RB4 RA3 RC34 LA1299 RB5 RA3 RC34 LA1300 RB18 RA3 RC34 LA1301 RB43 RA3 RC34 LA1302 RA3 RA3 RC34 LA1303 RA34 RA3 RC34 LA1304 RA57 RA3 RC34 LA1305 RB3 RA34 RC34 LA1306 RB4 RA34 RC34 LA1307 RB5 RA34 RC34 LA1308 RB7 RA34 RC34 LA1309 RB13 RA34 RC34 LA1310 RA3 RA34 RC34 LA1311 RA34 RA34 RC34 LA1312 RA57 RA34 RC34 LA1313 RB3 RB3 RC38 LA1314 RB4 RB4 RC38 LA1315 RB5 RB5 RC38 LA1316 RB18 RB18 RC38 LA1317 RB43 RB43 RC38 LA1318 RA3 RA3 RC38 LA1319 RA34 RA34 RC38 LA1320 RA57 RA57 RC38 LA1321 RB3 RB7 RC38 LA1322 RB4 RB7 RC38 LA1323 RB5 RB7 RC38 LA1324 RB18 RB7 RC38 LA1325 RB43 RB7 RC38 LA1326 RA3 RB7 RC38 LA1327 RA34 RB7 RC38 LA1328 RA57 RB7 RC38 LA1329 RB3 RA3 RC38 LA1330 RB4 RA3 RC38 LA1331 RB5 RA3 RC38 LA1332 RB18 RA3 RC38 LA1333 RB43 RA3 RC38 LA1334 RA3 RA3 RC38 LA1335 RA34 RA3 RC38 LA1336 RA57 RA3 RC38 LA1337 RB3 RA34 RC38 LA1338 RB4 RA34 RC38 LA1339 RB5 RA34 RC38 LA1340 RB18 RA34 RC38 LA1341 RB43 RA34 RC38 LA1342 RA3 RA34 RC38 LA1343 RA34 RA34 RC38 LA1344 RA57 RA34 RC38,
LA1345 through LA1792 based on a structure of Formula II
Figure US20240025934A1-20240125-C00247
in which R1, R2, and G are defined as:
Ligand R1 R2 G LA1345 RB13 RB3 RC2 LA1346 RB13 RB4 RC2 LA1347 RB13 RB5 RC2 LA1348 RB13 RB18 RC2 LA1349 RB13 RB43 RC2 LA1350 RB13 RA3 RC2 LA1351 RB13 RA34 RC2 LA1352 RB13 RA57 RC2 LA1353 RB7 RB3 RC2 LA1354 RB7 RB4 RC2 LA1355 RB7 RB5 RC2 LA1356 RB7 RB18 RC2 LA1357 RB7 RB43 RC2 LA1358 RB7 RA3 RC2 LA1359 RB7 RA34 RC2 LA1360 RB7 RA57 RC2 LA1361 RA3 RB3 RC2 LA1362 RA3 RB4 RC2 LA1363 RA3 RB5 RC2 LA1364 RA3 RB18 RC2 LA1365 RA3 RB43 RC2 LA1366 RA3 RA3 RC2 LA1367 RA3 RA34 RC2 LA1368 RA3 RA57 RC2 LA1369 RA34 RB3 RC2 LA1370 RA34 RB4 RC2 LA1371 RA34 RB5 RC2 LA1372 RA34 RB18 RC2 LA1373 RA34 RB43 RC2 LA1374 RA34 RA3 RC2 LA1375 RA34 RA34 RC2 LA1376 RA34 RA57 RC2 LA1377 RB13 RB3 RC5 LA1378 RB13 RB4 RC5 LA1379 RB13 RB5 RC5 LA1380 RB13 RB18 RC5 LA1381 RB13 RB43 RC5 LA1382 RB13 RA3 RC5 LA1383 RB13 RA34 RC5 LA1384 RB13 RA57 RC5 LA1385 RB7 RB3 RC5 LA1386 RB7 RB4 RC5 LA1387 RB7 RB5 RC5 LA1388 RB7 RB18 RC5 LA1389 RB7 RB43 RC5 LA1390 RB7 RA3 RC5 LA1391 RB7 RA34 RC5 LA1392 RB7 RA57 RC5 LA1393 RA3 RB3 RC5 LA1394 RA3 RB4 RC5 LA1395 RA3 RB5 RC5 LA1396 RA3 RB18 RC5 LA1397 RA3 RB43 RC5 LA1398 RA3 RA3 RC5 LA1399 RA3 RA34 RC5 LA1400 RA3 RA57 RC5 LA1401 RA34 RB3 RC5 LA1402 RA34 RB4 RC5 LA1403 RA34 RB5 RC5 LA1404 RA34 RB18 RC5 LA1405 RA34 RB43 RC5 LA1406 RA34 RA3 RC5 LA1407 RA34 RA34 RC5 LA1408 RA34 RA57 RC5 LA1409 RB13 RB3 RC6 LA1410 RB13 RB4 RC6 LA1411 RB13 RB5 RC6 LA1412 RB13 RB18 RC6 LA1413 RB13 RB43 RC6 LA1414 RB13 RA3 RC6 LA1415 RB13 RA34 RC6 LA1416 RB13 RA57 RC6 LA1417 RB7 RB3 RC6 LA1418 RB7 RB4 RC6 LA1419 RB7 RB5 RC6 LA1420 RB7 RB18 RC6 LA1421 RB7 RB43 RC6 LA1422 RB7 RA3 RC6 LA1423 RB7 RA34 RC6 LA1424 RB7 RA57 RC6 LA1425 RA3 RB3 RC6 LA1426 RA3 RB4 RC6 LA1427 RA3 RB5 RC6 LA1428 RA3 RB18 RC6 LA1429 RA3 RB43 RC6 LA1430 RA3 RA3 RC6 LA1431 RA3 RA34 RC6 LA1432 RA3 RA57 RC6 LA1433 RA34 RB3 RC6 LA1434 RA34 RB4 RC6 LA1435 RA34 RB5 RC6 LA1436 RA34 RB18 RC6 LA1437 RA34 RB43 RC6 LA1438 RA34 RA3 RC6 LA1439 RA34 RA34 RC6 LA1440 RA34 RA57 RC6 LA1441 RB13 RB3 RC7 LA1442 RB13 RB4 RC7 LA1443 RB13 RB5 RC7 LA1444 RB13 RB18 RC7 LA1445 RB13 RB43 RC7 LA1446 RB13 RA3 RC7 LA1447 RB13 RA34 RC7 LA1448 RB13 RA57 RC7 LA1449 RB7 RB3 RC7 LA1450 RB7 RB4 RC7 LA1451 RB7 RB5 RC7 LA1452 RB7 RB18 RC7 LA1453 RB7 RB43 RC7 LA1454 RB7 RA3 RC7 LA1455 RB7 RA34 RC7 LA1456 RB7 RA57 RC7 LA1457 RA3 RB3 RC7 LA1458 RA3 RB4 RC7 LA1459 RA3 RB5 RC7 LA1460 RA3 RB18 RC7 LA1461 RA3 RB43 RC7 LA1462 RA3 RA3 RC7 LA1463 RA3 RA34 RC7 LA1464 RA3 RA57 RC7 LA1465 RA34 RB3 RC7 LA1466 RA34 RB4 RC7 LA1467 RA34 RB5 RC7 LA1468 RA34 RB18 RC7 LA1469 RA34 RB43 RC7 LA1470 RA34 RA3 RC7 LA1471 RA34 RA34 RC7 LA1472 RA34 RA57 RC7 LA1473 RB13 RB3 RC10 LA1474 RB13 RB4 RC10 LA1475 RB13 RB5 RC10 LA1476 RB13 RB18 RC10 LA1477 RB13 RB43 RC10 LA1478 RB13 RA3 RC10 LA1479 RB13 RA34 RC10 LA1480 RB13 RA57 RC10 LA1481 RB7 RB3 RC10 LA1482 RB7 RB4 RC10 LA1483 RB7 RB5 RC10 LA1484 RB7 RB18 RC10 LA1485 RB7 RB43 RC10 LA1486 RB7 RA3 RC10 LA1487 RB7 RA34 RC10 LA1488 RB7 RA57 RC10 LA1489 RA3 RB3 RC10 LA1490 RA3 RB4 RC10 LA1491 RA3 RB5 RC10 LA1492 RA3 RB18 RC10 LA1493 RA3 RB43 RC10 LA1494 RA3 RA3 RC10 LA1495 RA3 RA34 RC10 LA1496 RA3 RA57 RC10 LA1497 RA34 RB3 RC10 LA1498 RA34 RB4 RC10 LA1499 RA34 RB5 RC10 LA1500 RA34 RB18 RC10 LA1501 RA34 RB43 RC10 LA1502 RA34 RA3 RC10 LA1503 RA34 RA34 RC10 LA1504 RA34 RA57 RC10 LA1505 RB13 RB3 RC11 LA1506 RB13 RB4 RC11 LA1507 RB13 RB5 RC11 LA1508 RB13 RB18 RC11 LA1509 RB13 RB43 RC11 LA1510 RB13 RA3 RC11 LA1511 RB3 RA34 RC11 LA1512 RB13 RA57 RC11 LA1513 RB7 RB3 RC11 LA1514 RB7 RB4 RC11 LA1515 RB7 RB5 RC11 LA1516 RB7 RB18 RC11 LA1517 RB7 RB43 RC11 LA1518 RB7 RA3 RC11 LA1519 RB7 RA34 RC11 LA1520 RB7 RA57 RC11 LA1521 RA3 RB3 RC11 LA1522 RA3 RB4 RC11 LA1523 RA3 RB5 RC11 LA1524 RA3 RB18 RC11 LA1525 RA3 RB43 RC11 LA1526 RA3 RA3 RC11 LA1527 RA3 RA34 RC11 LA1528 RA3 RA57 RC11 LA1529 RA34 RB3 RC11 LA1530 RA34 RB4 RC11 LA1531 RA34 RB5 RC11 LA1532 RA34 RB18 RC11 LA1533 RA34 RB43 RC11 LA1534 RA34 RA3 RC11 LA1535 RA34 RA34 RC11 LA1536 RA34 RA57 RC11 LA1537 RB13 RB3 RC13 LA1538 RB13 RB4 RC13 LA1539 RB13 RB5 RC13 LA1540 RB13 RB18 RC13 LA1541 RB13 RB43 RC13 LA1542 RB13 RA3 RC13 LA1543 RB13 RA34 RC13 LA1544 RB13 RA57 RC13 LA1545 RB7 RB3 RC13 LA1546 RB7 RB4 RC13 LA1547 RB7 RB5 RC13 LA1548 RB7 RB18 RC13 LA1549 RB7 RB43 RC13 LA1550 RB7 RA3 RC13 LA1551 RB7 RA34 RC13 LA1552 RB7 RA57 RC13 LA1553 RA3 RB3 RC13 LA1554 RA3 RB4 RC13 LA1555 RA3 RB5 RC13 LA1556 RA3 RB18 RC13 LA1557 RA3 RB43 RC13 LA1558 RA3 RA3 RC13 LA1559 RA3 RA34 RC13 LA1560 RA3 RA57 RC13 LA1561 RA34 RB3 RC13 LA1562 RA34 RB4 RC13 LA1563 RA34 RB5 RC13 LA1564 RA34 RB18 RC13 LA1565 RA34 RB43 RC13 LA1566 RA34 RA3 RC13 LA1567 RA34 RA34 RC13 LA1568 RA34 RA57 RC13 LA1569 RB13 RB3 RC17 LA1570 RB13 RB4 RC17 LA1571 RB13 RB5 RC17 LA1572 RB13 RB18 RC17 LA1573 RB13 RB43 RC17 LA1574 RB13 RA3 RC17 LA1575 RB13 RA34 RC17 LA1576 RB13 RA57 RC17 LA1577 RB7 RB3 RC17 LA1578 RB7 RB4 RC17 LA1579 RB7 RB5 RC17 LA1580 RB7 RB18 RC17 LA1581 RB7 RB43 RC17 LA1582 RB7 RA3 RC17 LA1583 RB7 RA34 RC17 LA1584 RB7 RA57 RC17 LA1585 RA3 RB3 RC17 LA1586 RA3 RB4 RC17 LA1587 RA3 RB5 RC17 LA1588 RA3 RB18 RC17 LA1589 RA3 RB43 RC17 LA1590 RA3 RA3 RC17 LA1591 RA3 RA34 RC17 LA1592 RA3 RA57 RC17 LA1593 RA34 RB3 RC17 LA1594 RA34 RB4 RC17 LA1595 RA34 RB5 RC17 LA1596 RA34 RB18 RC17 LA1597 RA34 RB43 RC17 LA1598 RA34 RA3 RC17 LA1599 RA34 RA34 RC17 LA1600 RA34 RA57 RC17 LA1601 RB13 RB3 RC20 LA1602 RB13 RB4 RC20 LA1603 RB13 RB5 RC20 LA1604 RB13 RB18 RC20 LA1605 RB13 RB43 RC20 LA1606 RB13 RA3 RC20 LA1607 RB13 RA34 RC20 LA1608 RB13 RA57 RC20 LA1609 RB7 RB3 RC20 LA1610 RB7 RB4 RC20 LA1611 RB7 RB5 RC20 LA1612 RB7 RB18 RC20 LA1613 RB7 RB43 RC20 LA1614 RB7 RA3 RC20 LA1615 RB7 RA34 RC20 LA1616 RB7 RA57 RC20 LA1617 RA3 RB3 RC20 LA1618 RA3 RB4 RC20 LA1619 RA3 RB5 RC20 LA1620 RA3 RB18 RC20 LA1621 RA3 RB43 RC20 LA1622 RA3 RA3 RC20 LA1623 RA3 RA34 RC20 LA1624 RA3 RA57 RC20 LA1625 RA34 RB3 RC20 LA1626 RA34 RB4 RC20 LA1627 RA34 RB5 RC20 LA1628 RA34 RB18 RC20 LA1629 RA34 RB43 RC20 LA1630 RA34 RA3 RC20 LA1631 RA34 RA34 RC20 LA1632 RA34 RA57 RC20 LA1633 RB13 RB3 RC24 LA1634 RB13 RB4 RC24 LA1635 RB13 RB5 RC24 LA1636 RB13 RB18 RC24 LA1637 RB13 RB43 RC24 LA1638 RB13 RA3 RC24 LA1639 RB13 RA34 RC24 LA1640 RB13 RA57 RC24 LA1641 RB7 RB3 RC24 LA1642 RB7 RB4 RC24 LA1643 RB7 RB5 RC24 LA1644 RB7 RB18 RC24 LA1645 RB7 RB43 RC24 LA1646 RB7 RA3 RC24 LA1647 RB7 RA34 RC24 LA1648 RB7 RA57 RC24 LA1649 RA3 RB3 RC24 LA1650 RA3 RB4 RC24 LA1651 RA3 RB5 RC24 LA1652 RA3 RB18 RC24 LA1653 RA3 RB43 RC24 LA1654 RA3 RA3 RC24 LA1655 RA3 RA34 RC24 LA1656 RA3 RA57 RC24 LA1657 RA34 RB3 RC24 LA1658 RA34 RB4 RC24 LA1659 RA34 RB5 RC24 LA1660 RA34 RB18 RC24 LA1661 RA34 RB43 RC24 LA1662 RA34 RA3 RC24 LA1663 RA34 RA34 RC24 LA1664 RA34 RA57 RC24 LA1665 RB13 RB3 RC27 LA1666 RB13 RB4 RC27 LA1667 RB13 RB5 RC27 LA1668 RB13 RB18 RC27 LA1669 RB13 RB43 RC27 LA1670 RB13 RA3 RC27 LA1671 RB13 RA34 RC27 LA1672 RB13 RA57 RC27 LA1673 RB7 RB3 RC27 LA1674 RB7 RB4 RC27 LA1675 RB7 RB5 RC27 LA1676 RB7 RB18 RC27 LA1677 RB7 RB43 RC27 LA1678 RB7 RA3 RC27 LA1679 RB7 RA34 RC27 LA1680 RB7 RA57 RC27 LA1681 RA3 RB3 RC27 LA1682 RA3 RB4 RC27 LA1683 RA3 RB5 RC27 LA1684 RA3 RB18 RC27 LA1685 RA3 RB43 RC27 LA1686 RA3 RA3 RC27 LA1687 RA3 RA34 RC27 LA1688 RA3 RA57 RC27 LA1689 RA34 RB3 RC27 LA1690 RA34 RB4 RC27 LA1691 RA34 RB5 RC27 LA1692 RA34 RB18 RC27 LA1693 RA34 RB43 RC27 LA1694 RA34 RA3 RC27 LA1695 RA34 RA34 RC27 LA1696 RA34 RA57 RC27 LA1697 RB13 RB3 RC31 LA1698 RB13 RB4 RC31 LA1699 RB13 RB5 RC31 LA1700 RB13 RB18 RC31 LA1701 RB13 RB43 RC31 LA1702 RB13 RA3 RC31 LA1703 RB13 RA34 RC31 LA1704 RB13 RA57 RC31 LA1705 RB7 RB3 RC31 LA1706 RB7 RB4 RC31 LA1707 RB7 RB5 RC31 LA1708 RB7 RB18 RC31 LA1709 RB7 RB43 RC31 LA1710 RB7 RA3 RC31 LA1711 RB7 RA34 RC31 LA1712 RB7 RA57 RC31 LA1713 RA3 RB3 RC31 LA1714 RA3 RB4 RC31 LA1715 RA3 RB5 RC31 LA1716 RA3 RB18 RC31 LA1717 RA3 RB43 RC31 LA1718 RA3 RA3 RC31 LA1719 RA3 RA34 RC31 LA1720 RA3 RA57 RC31 LA1721 RA34 RB3 RC31 LA1722 RA34 RB4 RC31 LA1723 RA34 RB5 RC31 LA1724 RA34 RB18 RC31 LA1725 RA34 RB43 RC31 LA1726 RA34 RA3 RC31 LA1727 RA34 RA34 RC31 LA1728 RA34 RA57 RC31 LA1729 RB13 RB3 RC34 LA1730 RB13 RB4 RC34 LA1731 RB13 RB5 RC34 LA1732 RB13 RB18 RC34 LA1733 RB13 RB43 RC34 LA1734 RB13 RA3 RC34 LA1735 RB13 RA34 RC34 LA1736 RB13 RA57 RC34 LA1737 RB7 RB3 RC34 LA1738 RB7 RB4 RC34 LA1739 RB7 RB5 R34 LA1740 RB7 RB18 RC34 LA1741 RB7 RB43 RC34 LA1742 RB7 RA3 RC34 LA1743 RB7 RA34 RC34 LA1744 RB7 RA57 RC34 LA1745 RA3 RB3 RC34 LA1746 RA3 RB4 RC34 LA1747 RA3 RB5 RC34 LA1748 RA3 RB18 RC34 LA1749 RA3 RB43 RC34 LA1750 RA3 RA3 RC34 LA1751 RA3 RA34 RC34 LA1752 RA3 RA57 RC34 LA1753 RA34 RB3 RC34 LA1754 RA34 RB4 RC34 LA1755 RA34 RB5 RC34 LA1756 RA34 RB7 RC34 LA1757 RA34 RB13 RC34 LA1758 RA34 RA3 RC34 LA1759 RA34 RA34 RC34 LA1760 RA34 RA57 RC34 LA1761 RB13 RB3 RC38 LA1762 RB13 RB4 RC38 LA1763 RB13 RB5 RC38 LA1764 RB3 RB18 RC38 LA1765 RB13 RB43 RC38 LA1766 RB13 RA3 RC38 LA1767 RB13 RA34 RC38 LA1768 RB13 RA57 RC38 LA1769 RB7 RB3 RC38 LA1770 RB7 RB4 RC38 LA1771 RB7 RB5 RC38 LA1772 RB7 RB18 RC38 LA1773 RB7 RB43 RC38 LA1774 RB7 RA3 RC38 LA1775 RB7 RA34 RC38 LA1776 RB7 RA57 RC38 LA1777 RA3 RB3 RC38 LA1778 RA3 RB4 RC38 LA1779 RA3 RB5 RC38 LA1780 RA3 RB18 RC38 LA1781 RA3 RB43 RC38 LA1782 RA3 RA3 RC38 LA1783 RA3 RA34 RC38 LA1784 RA3 RA57 RC38 LA1785 RA34 RB3 RC38 LA1786 RA34 RB4 RC38 LA1787 RA34 RB5 RC38 LA1788 RA34 RB18 RC38 LA1789 RA34 RB43 RC38 LA1790 RA34 RA3 RC38 LA1791 RA34 RA34 RC38 LA1792 RA34 RA57 RC38,
wherein RA1 to RA74 have the following structures:
Figure US20240025934A1-20240125-C00248
Figure US20240025934A1-20240125-C00249
Figure US20240025934A1-20240125-C00250
Figure US20240025934A1-20240125-C00251
Figure US20240025934A1-20240125-C00252
Figure US20240025934A1-20240125-C00253
wherein RB1 to RB42 have the following structures:
Figure US20240025934A1-20240125-C00254
Figure US20240025934A1-20240125-C00255
Figure US20240025934A1-20240125-C00256
Figure US20240025934A1-20240125-C00257
Figure US20240025934A1-20240125-C00258
wherein RC1 to RC42 have the following structures:
Figure US20240025934A1-20240125-C00259
Figure US20240025934A1-20240125-C00260
Figure US20240025934A1-20240125-C00261
Figure US20240025934A1-20240125-C00262
Figure US20240025934A1-20240125-C00263
Figure US20240025934A1-20240125-C00264
Figure US20240025934A1-20240125-C00265
10. The compound of claim 1, wherein the compound has a formula of M(LA)x(LB)y(LC)z wherein LB and LC are each a bidentate ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.
11. The compound of claim 10, wherein 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), wherein LA, LB, and LC are different from each other, or the compound has a formula of Pt(LA)(LB), wherein LA and LB can be same or different.
12. The compound of claim 10, wherein LB and LC are each independently selected from the group consisting of:
Figure US20240025934A1-20240125-C00266
Figure US20240025934A1-20240125-C00267
Figure US20240025934A1-20240125-C00268
wherein
each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of B Re, N Re, P Re, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
wherein Re and Rf are optionally fused or joined to form a ring;
wherein each Ra, Rb, Re, and Rd may independently represent from mono substitution to the maximum possible number of substitutions, or no substitution;
wherein each Ra, Rb, Re, Rd, Re and Rf is independently a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
wherein any two adjacent substituents of Ra, Rb, Re, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
13. The compound of claim 9, wherein the compound is Compound Ax having the formula Ir(LA)3, the Compound By having the formula Ir(LA)(LB)2, or the Compound Cz having the formula Ir(LA)2(LC);
wherein LA is selected from the group consisting of LAi, wherein i is an integer from 1 to 1792;
wherein LB is selected from the group consisting of LBk, wherein k is an integer from 1 to 468;
wherein LC is selected from the group consisting of LCj, wherein j is an integer from 1 to 1260;
wherein x=i, y=468+k−468, and z=12601+j−1260;
wherein each LBk has the following structure:
Figure US20240025934A1-20240125-C00269
Figure US20240025934A1-20240125-C00270
Figure US20240025934A1-20240125-C00271
Figure US20240025934A1-20240125-C00272
Figure US20240025934A1-20240125-C00273
Figure US20240025934A1-20240125-C00274
Figure US20240025934A1-20240125-C00275
Figure US20240025934A1-20240125-C00276
Figure US20240025934A1-20240125-C00277
Figure US20240025934A1-20240125-C00278
Figure US20240025934A1-20240125-C00279
Figure US20240025934A1-20240125-C00280
Figure US20240025934A1-20240125-C00281
Figure US20240025934A1-20240125-C00282
Figure US20240025934A1-20240125-C00283
Figure US20240025934A1-20240125-C00284
Figure US20240025934A1-20240125-C00285
Figure US20240025934A1-20240125-C00286
Figure US20240025934A1-20240125-C00287
Figure US20240025934A1-20240125-C00288
Figure US20240025934A1-20240125-C00289
Figure US20240025934A1-20240125-C00290
Figure US20240025934A1-20240125-C00291
Figure US20240025934A1-20240125-C00292
Figure US20240025934A1-20240125-C00293
Figure US20240025934A1-20240125-C00294
Figure US20240025934A1-20240125-C00295
Figure US20240025934A1-20240125-C00296
Figure US20240025934A1-20240125-C00297
Figure US20240025934A1-20240125-C00298
Figure US20240025934A1-20240125-C00299
Figure US20240025934A1-20240125-C00300
Figure US20240025934A1-20240125-C00301
Figure US20240025934A1-20240125-C00302
Figure US20240025934A1-20240125-C00303
Figure US20240025934A1-20240125-C00304
Figure US20240025934A1-20240125-C00305
Figure US20240025934A1-20240125-C00306
Figure US20240025934A1-20240125-C00307
Figure US20240025934A1-20240125-C00308
Figure US20240025934A1-20240125-C00309
Figure US20240025934A1-20240125-C00310
Figure US20240025934A1-20240125-C00311
Figure US20240025934A1-20240125-C00312
Figure US20240025934A1-20240125-C00313
Figure US20240025934A1-20240125-C00314
Figure US20240025934A1-20240125-C00315
Figure US20240025934A1-20240125-C00316
Figure US20240025934A1-20240125-C00317
Figure US20240025934A1-20240125-C00318
Figure US20240025934A1-20240125-C00319
Figure US20240025934A1-20240125-C00320
Figure US20240025934A1-20240125-C00321
Figure US20240025934A1-20240125-C00322
Figure US20240025934A1-20240125-C00323
Figure US20240025934A1-20240125-C00324
Figure US20240025934A1-20240125-C00325
Figure US20240025934A1-20240125-C00326
Figure US20240025934A1-20240125-C00327
Figure US20240025934A1-20240125-C00328
Figure US20240025934A1-20240125-C00329
Figure US20240025934A1-20240125-C00330
Figure US20240025934A1-20240125-C00331
Figure US20240025934A1-20240125-C00332
Figure US20240025934A1-20240125-C00333
Figure US20240025934A1-20240125-C00334
Figure US20240025934A1-20240125-C00335
Figure US20240025934A1-20240125-C00336
Figure US20240025934A1-20240125-C00337
Figure US20240025934A1-20240125-C00338
Figure US20240025934A1-20240125-C00339
Figure US20240025934A1-20240125-C00340
Figure US20240025934A1-20240125-C00341
Figure US20240025934A1-20240125-C00342
Figure US20240025934A1-20240125-C00343
Figure US20240025934A1-20240125-C00344
Figure US20240025934A1-20240125-C00345
Figure US20240025934A1-20240125-C00346
Figure US20240025934A1-20240125-C00347
Figure US20240025934A1-20240125-C00348
Figure US20240025934A1-20240125-C00349
Figure US20240025934A1-20240125-C00350
Figure US20240025934A1-20240125-C00351
Figure US20240025934A1-20240125-C00352
Figure US20240025934A1-20240125-C00353
Figure US20240025934A1-20240125-C00354
Figure US20240025934A1-20240125-C00355
Figure US20240025934A1-20240125-C00356
Figure US20240025934A1-20240125-C00357
Figure US20240025934A1-20240125-C00358
Figure US20240025934A1-20240125-C00359
Figure US20240025934A1-20240125-C00360
Figure US20240025934A1-20240125-C00361
Figure US20240025934A1-20240125-C00362
Figure US20240025934A1-20240125-C00363
and
wherein each LCj has a structure of Formula X
Figure US20240025934A1-20240125-C00364
in which R1, R2, and R3 are defined as:
Ligand R1 R2 R3 LC1 RD1 RD1 H LC2 RD2 RD2 H LC3 RD3 RD3 H LC4 RD4 RD4 H LC5 RD5 RD5 H LC6 RD6 RD6 H LC7 RD7 RD7 H LC8 RD8 RD8 H LC9 RD9 RD9 H LC10 RD10 RD10 H LC11 RD11 RD11 H LC12 RD12 RD12 H LC13 RD13 RD13 H LC14 RD14 RD14 H LC15 RD15 RD15 H LC16 RD16 RD16 H LC17 RD17 RD17 H LC18 RD18 RD18 H LC19 RD19 RD19 H LC20 RD20 RD20 H LC21 RD21 RD21 H LC22 RD22 RD22 H LC23 RD23 RD23 H LC24 RD24 RD24 H LC25 RD25 RD25 H LC26 RD26 RD26 H LC27 RD27 RD27 H LC28 RD28 RD28 H LC29 RD29 RD29 H LC30 RD30 RD30 H LC31 RD31 RD31 H LC32 RD32 RD32 H LC33 RD33 RD33 H LC34 RD34 RD34 H LC35 RD35 RD35 H LC36 RD40 RD40 H LC37 RD41 RD41 H LC38 RD42 RD42 H LC39 RD64 RD64 H LC40 RD66 RD66 H LC41 RD68 RD68 H LC42 RD76 RD76 H LC43 RD1 RD2 H LC44 RD1 RD3 H LC45 RD1 RD4 H LC46 RD1 RD5 H LC47 RD1 RD6 H LC48 RD1 RD7 H LC49 RD1 RD8 H LC50 RD1 RD9 H LC51 RD1 RD10 H LC52 RD1 RD11 H LC53 RD1 RD12 H LC54 RD1 RD13 H LC55 RD1 RD14 H LC56 RD1 RD15 H LC57 RD1 RD16 H LC58 RD1 RD17 H LC59 RD1 RD18 H LC60 RD1 RD19 H LC61 RD1 RD20 H LC62 RD1 RD21 H LC63 RD1 RD22 H LC64 RD1 RD23 H LC65 RD1 RD24 H LC66 RD1 RD25 H LC67 RD1 RD26 H LC68 RD1 RD27 H LC69 RD1 RD28 H LC70 RD1 RD29 H LC71 RD1 RD30 H LC72 RD1 RD31 H LC73 RD1 RD32 H LC74 RD1 RD33 H LC75 RD1 RD34 H LC76 RD1 RD35 H LC77 RD1 RD40 H LC78 RD1 RD41 H LC79 RD1 RD42 H LC80 RD1 RD64 H LC81 RD1 RD66 H LC82 RD1 RD68 H LC83 RD1 RD76 H LC84 RD2 RD1 H LC85 RD2 RD3 H LC86 RD2 RD4 H LC87 RD2 RD5 H LC88 RD2 RD6 H LC89 RD2 RD7 H LC90 RD2 RD8 H LC91 RD2 RD9 H LC92 RD2 RD10 H LC93 RD2 RD11 H LC94 RD2 RD12 H LC95 RD2 RD13 H LC96 RD2 RD14 H LC97 RD2 RD15 H LC98 RD2 RD16 H LC99 RD2 RD17 H LC100 RD2 RD18 H LC101 RD2 RD19 H LC102 RD2 RD20 H LC103 RD2 RD21 H LC104 RD2 RD22 H LC105 RD2 RD23 H LC106 RD2 RD24 H LC107 RD2 RD25 H LC108 RD2 RD26 H LC109 RD2 RD27 H LC110 RD2 RD28 H LC111 RD2 RD29 H LC112 RD2 RD30 H LC113 RD2 RD31 H LC114 RD2 RD32 H LC115 RD2 RD33 H LC116 RD2 RD34 H LC117 RD2 RD35 H LC118 RD2 RD40 H LC119 RD2 RD41 H LC120 RD2 RD42 H LC121 RD2 RD64 H LC122 RD2 RD66 H LC123 RD2 RD68 H LC124 RD2 RD76 H LC125 RD3 RD4 H LC126 RD3 RD5 H LC127 RD3 RD6 H LC128 RD3 RD7 H LC129 RD3 RD8 H LC130 RD3 RD9 H LC131 RD3 RD10 H LC132 RD3 RD11 H LC133 RD3 RD12 H LC134 RD3 RD13 H LC135 RD3 RD14 H LC136 RD3 RD15 H LC137 RD3 RD16 H LC138 RD3 RD17 H LC139 RD3 RD18 H LC140 RD3 RD19 H LC141 RD3 RD20 H LC142 RD3 RD21 H LC143 RD3 RD22 H LC144 RD3 RD23 H LC145 RD3 RD24 H LC146 RD3 RD25 H LC147 RD3 RD26 H LC148 RD3 RD27 H LC149 RD3 RD28 H LC150 RD3 RD29 H LC151 RD3 RD30 H LC152 RD3 RD31 H LC153 RD3 RD32 H LC154 RD3 RD33 H LC155 RD3 RD34 H LC156 RD3 RD35 H LC157 RD3 RD40 H LC158 RD3 RD41 H LC159 RD3 RD42 H LC160 RD3 RD64 H LC161 RD3 RD66 H LC162 RD3 RD68 H LC163 RD3 RD76 H LC164 RD4 RD5 H LC165 RD4 RD6 H LC166 RD4 RD7 H LC167 RD4 RD8 H LC168 RD4 RD9 H LC169 RD4 RD10 H LC170 RD4 RD11 H LC171 RD4 RD12 H LC172 RD4 RD13 H LC173 RD4 RD14 H LC174 RD4 RD15 H LC175 RD4 RD16 H LC176 RD4 RD17 H LC177 RD4 RD18 H LC178 RD4 RD19 H LC179 RD4 RD20 H LC180 RD4 RD21 H LC181 RD4 RD22 H LC182 RD4 RD23 H LC183 RD4 RD24 H LC184 RD4 RD25 H LC185 RD4 RD26 H LC186 RD4 RD27 H LC187 RD4 RD28 H LC188 RD4 RD29 H LC189 RD4 RD30 H LC190 RD4 RD31 H LC191 RD4 RD32 H LC192 RD4 RD33 H LC193 RD4 RD34 H LC194 RD4 RD35 H LC195 RD4 RD40 H LC196 RD4 RD41 H LC197 RD4 RD42 H LC198 RD4 RD64 H LC199 RD4 RD66 H LC200 RD4 RD68 H LC201 RD4 RD76 H LC202 RD4 RD1 H LC203 RD7 RD5 H LC204 RD7 RD6 H LC205 RD7 RD8 H LC206 RD7 RD9 H LC207 RD7 RD10 H LC208 RD7 RD11 H LC209 RD7 RD12 H LC210 RD7 RD13 H LC211 RD7 RD14 H LC212 RD7 RD15 H LC213 RD7 RD16 H LC214 RD7 RD17 H LC215 RD7 RD18 H LC216 RD7 RD19 H LC217 RD7 RD20 H LC218 RD7 RD21 H LC219 RD7 RD22 H LC220 RD7 RD23 H LC221 RD7 RD24 H LC222 RD7 RD25 H LC223 RD7 RD26 H LC224 RD7 RD27 H LC225 RD7 RD28 H LC226 RD7 RD29 H LC227 RD7 RD30 H LC228 RD7 RD31 H LC229 RD7 RD32 H LC230 RD7 RD33 H LC231 RD7 RD34 H LC232 RD7 RD35 H LC233 RD7 RD40 H LC234 RD7 RD41 H LC235 RD7 RD42 H LC236 RD7 RD64 H LC237 RD7 RD66 H LC238 RD7 RD68 H LC239 RD7 RD76 H LC240 RD8 RD5 H LC241 RD8 RD6 H LC242 RD8 RD9 H LC243 RD8 RD10 H LC244 RD8 RD11 H LC245 RD8 RD12 H LC246 RD8 RD13 H LC247 RD8 RD14 H LC248 RD8 RD15 H LC249 RD8 RD16 H LC250 RD8 RD17 H LC251 RD8 RD18 H LC252 RD8 RD19 H LC253 RD8 RD20 H LC254 RD8 RD21 H LC255 RD8 RD22 H LC256 RD8 RD23 H LC257 RD8 RD24 H LC258 RD8 RD25 H LC259 RD8 RD26 H LC260 RD8 RD27 H LC261 RD8 RD28 H LC262 RD8 RD29 H LC263 RD8 RD30 H LC264 RD8 RD31 H LC265 RD8 RD32 H LC266 RD8 RD33 H LC267 RD8 RD34 H LC268 RD8 RD35 H LC269 RD8 RD40 H LC270 RD8 RD41 H LC271 RD8 RD42 H LC272 RD8 RD64 H LC273 RD8 RD66 H LC274 RD8 RD68 H LC275 RD8 RD76 H LC276 RD11 RD5 H LC277 RD11 RD6 H LC278 RD11 RD9 H LC279 RD11 RD10 H LC280 RD11 RD12 H LC281 RD11 RD13 H LC282 RD11 RD14 H LC283 RD11 RD15 H LC284 RD11 RD16 H LC285 RD11 RD17 H LC286 RD11 RD18 H LC287 RD11 RD19 H LC288 RD11 RD20 H LC289 RD11 RD21 H LC290 RD11 RD22 H LC291 RD11 RD23 H LC292 RD11 RD24 H LC293 RD11 RD25 H LC294 RD11 RD26 H LC295 RD11 RD27 H LC296 RD11 RD28 H LC297 RD11 RD29 H LC298 RD11 RD30 H LC299 RD11 RD31 H LC300 RD11 RD32 H LC301 RD11 RD33 H LC302 RD11 RD34 H LC303 RD11 RD35 H LC304 RD11 RD40 H LC305 RD11 RD41 H LC306 RD11 RD42 H LC307 RD11 RD64 H LC308 RD11 RD66 H LC309 RD11 RD68 H LC310 RD11 RD76 H LC311 RD13 RD5 H LC312 RD13 RD6 H LC313 RD13 RD9 H LC314 RD13 RD10 H LC315 RD13 RD12 H LC316 RD13 RD14 H LC317 RD13 RD15 H LC318 RD13 RD16 H LC319 RD13 RD17 H LC320 RD13 RD18 H LC321 RD13 RD19 H LC322 RD13 RD20 H LC323 RD13 RD21 H LC324 RD13 RD22 H LC325 RD13 RD23 H LC326 RD13 RD24 H LC327 RD13 RD25 H LC328 RD13 RD26 H LC329 RD13 RD27 H LC330 RD13 RD28 H LC331 RD13 RD29 H LC332 RD13 RD30 H LC333 RD13 RD31 H LC334 RD13 RD32 H LC335 RD13 RD33 H LC336 RD13 RD34 H LC337 RD13 RD35 H LC338 RD13 RD40 H LC339 RD13 RD41 H LC340 RD13 RD42 H LC341 RD13 RD64 H LC342 RD13 RD66 H LC343 RD13 RD68 H LC344 RD13 RD76 H LC345 RD14 RD5 H LC346 RD14 RD6 H LC347 RD14 RD9 H LC348 RD14 RD10 H LC349 RD14 RD12 H LC350 RD14 RD15 H LC351 RD14 RD16 H LC352 RD14 RD17 H LC353 RD14 RD18 H LC354 RD14 RD19 H LC355 RD14 RD20 H LC356 RD14 RD21 H LC357 RD14 RD22 H LC358 RD14 RD23 H LC359 RD14 RD24 H LC360 RD14 RD25 H LC361 RD14 RD26 H LC362 RD14 RD27 H LC363 RD14 RD28 H LC364 RD14 RD29 H LC365 RD14 RD30 H LC366 RD14 RD31 H LC367 RD14 RD32 H LC368 RD14 RD33 H LC369 RD14 RD34 H LC370 RD14 RD35 H LC371 RD14 RD40 H LC372 RD14 RD41 H LC373 RD14 RD42 H LC374 RD14 RD64 H LC375 RD14 RD66 H LC376 RD14 RD68 H LC377 RD14 RD76 H LC378 RD22 RD5 H LC379 RD22 RD6 H LC380 RD22 RD9 H LC381 RD22 RD10 H LC382 RD22 RD12 H LC383 RD22 RD15 H LC384 RD22 RD16 H LC385 RD22 RD17 H LC386 RD22 RD18 H LC387 RD22 RD19 H LC388 RD22 RD20 H LC389 RD22 RD21 H LC390 RD22 RD23 H LC391 RD22 RD24 H LC392 RD22 RD25 H LC393 RD22 RD26 H LC394 RD22 RD27 H LC395 RD22 RD28 H LC396 RD22 RD29 H LC397 RD22 RD30 H LC398 RD22 RD31 H LC399 RD22 RD32 H LC400 RD22 RD33 H LC401 RD22 RD34 H LC402 RD22 RD35 H LC403 RD22 RD40 H LC404 RD22 RD41 H LC405 RD22 RD42 H LC406 RD22 RD64 H LC407 RD22 RD66 H LC408 RD22 RD68 H LC409 RD22 RD76 H LC410 RD26 RD5 H LC411 RD26 RD6 H LC412 RD26 RD9 H LC413 RD26 RD10 H LC414 RD26 RD12 H LC415 RD26 RD15 H LC416 RD26 RD16 H LC417 RD26 RD17 H LC418 RD26 RD18 H LC419 RD26 RD19 H LC420 RD26 RD20 H LC421 RD26 RD21 H LC422 RD26 RD23 H LC423 RD26 RD24 H LC424 RD26 RD25 H LC425 RD26 RD27 H LC426 RD26 RD28 H LC427 RD26 RD29 H LC428 RD26 RD30 H LC429 RD26 RD31 H LC430 RD26 RD32 H LC431 RD26 RD33 H LC432 RD26 RD34 H LC433 RD26 RD35 H LC434 RD26 RD40 H LC435 RD26 RD41 H LC436 RD26 RD42 H LC437 RD26 RD64 H LC438 RD26 RD66 H LC439 RD26 RD68 H LC440 RD26 RD76 H LC441 RD35 RD5 H LC442 RD35 RD6 H LC443 RD35 RD9 H LC444 RD35 RD10 H LC445 RD35 RD12 H LC446 RD35 RD15 H LC447 RD35 RD16 H LC448 RD35 RD17 H LC449 RD35 RD18 H LC450 RD35 RD19 H LC451 RD35 RD20 H LC452 RD35 RD21 H LC453 RD35 RD23 H LC454 RD35 RD24 H LC455 RD35 RD25 H LC456 RD35 RD27 H LC457 RD35 RD28 H LC458 RD35 RD29 H LC459 RD35 RD30 H LC460 RD35 RD31 H LC461 RD35 RD32 H LC462 RD35 RD33 H LC463 RD35 RD34 H LC464 RD35 RD40 H LC465 RD35 RD41 H LC466 RD35 RD42 H LC467 RD35 RD64 H LC468 RD35 RD66 H LC469 RD35 RD68 H LC470 RD35 RD76 H LC471 RD40 RD5 H LC472 RD40 RD6 H LC473 RD40 RD9 H LC474 RD40 RD10 H LC475 RD40 RD12 H LC476 RD40 RD15 H LC477 RD40 RD16 H LC478 RD40 RD17 H LC479 RD40 RD18 H LC480 RD40 RD19 H LC481 RD40 RD20 H LC482 RD40 RD21 H LC483 RD40 RD23 H LC484 RD40 RD24 H LC485 RD40 RD25 H LC486 RD40 RD27 H LC487 RD40 RD28 H LC488 RD40 RD29 H LC489 RD40 RD30 H LC490 RD40 RD31 H LC491 RD40 RD32 H LC492 RD40 RD33 H LC493 RD40 RD34 H LC494 RD40 RD41 H LC495 RD40 RD42 H LC496 RD40 RD64 H LC497 RD40 RD66 H LC498 RD40 RD68 H LC499 RD40 RD76 H LC500 RD41 RD5 H LC501 RD41 RD6 H LC502 RD41 RD9 H LC503 RD41 RD10 H LC504 RD41 RD12 H LC505 RD41 RD15 H LC506 RD41 RD16 H LC507 RD41 RD17 H LC508 RD41 RD18 H LC509 RD41 RD19 H LC510 RD41 RD20 H LC511 RD41 RD21 H LC512 RD41 RD23 H LC513 RD41 RD24 H LC514 RD41 RD25 H LC515 RD41 RD27 H LC516 RD41 RD28 H LC517 RD41 RD29 H LC518 RD41 RD30 H LC519 RD41 RD31 H LC520 RD41 RD32 H LC521 RD41 RD33 H LC522 RD41 RD34 H LC523 RD41 RD42 H LC524 RD41 RD64 H LC525 RD41 RD66 H LC526 RD41 RD68 H LC527 RD41 RD76 H LC528 RD64 RD5 H LC529 RD64 RD6 H LC530 RD64 RD9 H LC531 RD64 RD10 H LC532 RD64 RD12 H LC533 RD64 RD15 H LC534 RD64 RD16 H LC535 RD64 RD17 H LC536 RD64 RD18 H LC537 RD64 RD19 H LC538 RD64 RD20 H LC539 RD64 RD21 H LC540 RD64 RD23 H LC541 RD64 RD24 H LC542 RD64 RD25 H LC543 RD64 RD27 H LC544 RD64 RD28 H LC545 RD64 RD29 H LC546 RD64 RD30 H LC547 RD64 RD31 H LC548 RD64 RD32 H LC549 RD64 RD33 H LC550 RD64 RD34 H LC551 RD64 RD42 H LC552 RD64 RD64 H LC553 RD64 RD66 H LC554 RD64 RD68 H LC555 RD64 RD76 H LC556 RD66 RD5 H LC557 RD66 RD6 H LC558 RD66 RD9 H LC559 RD66 RD10 H LC560 RD66 RD12 H LC561 RD66 RD15 H LC562 RD66 RD16 H LC563 RD66 RD17 H LC564 RD66 RD18 H LC565 RD66 RD19 H LC566 RD66 RD20 H LC567 RD66 RD21 H LC568 RD66 RD23 H LC569 RD66 RD24 H LC570 RD66 RD25 H LC571 RD66 RD27 H LC572 RD66 RD28 H LC573 RD66 RD29 H LC574 RD66 RD30 H LC575 RD66 RD31 H LC576 RD66 RD32 H LC577 RD66 RD33 H LC578 RD66 RD34 H LC579 RD66 RD42 H LC580 RD66 RD68 H LC581 RD66 RD76 H LC582 RD68 RD5 H LC583 RD68 RD6 H LC584 RD68 RD9 H LC585 RD68 RD10 H LC586 RD68 RD12 H LC587 RD68 RD15 H LC588 RD68 RD16 H LC589 RD68 RD17 H LC590 RD68 RD18 H LC591 RD68 RD19 H LC592 RD68 RD20 H LC593 RD68 RD21 H LC594 RD68 RD23 H LC595 RD68 RD24 H LC596 RD68 RD25 H LC597 RD68 RD27 H LC598 RD68 RD28 H LC599 RD68 RD29 H LC600 RD68 RD30 H LC601 RD68 RD31 H LC602 RD68 RD32 H LC603 RD68 RD33 H LC604 RD68 RD34 H LC605 RD68 RD42 H LC606 RD68 RD76 H LC607 RD76 RD5 H LC608 RD76 RD6 H LC609 RD76 RD9 H LC610 RD76 RD10 H LC611 RD76 RD12 H LC612 RD76 RD15 H LC613 RD76 RD16 H LC614 RD76 RD17 H LC615 RD76 RD18 H LC616 RD76 RD19 H LC617 RD76 RD20 H LC618 RD76 RD21 H LC619 RD76 RD23 H LC620 RD76 RD24 H LC621 RD76 RD25 H LC622 RD76 RD27 H LC623 RD76 RD28 H LC624 RD76 RD29 H LC625 RD76 RD30 H LC626 RD76 RD31 H LC627 RD76 RD32 H LC628 RD76 RD33 H LC629 RD76 RD34 H LC630 RD76 RD42 H LC631 RD1 RD1 RD1 LC632 RD2 RD2 RD1 LC633 RD3 RD3 RD1 LC634 RD4 RD4 RD1 LC635 RD5 RD5 RD1 LC636 RD6 RD6 RD1 LC637 RD7 RD7 RD1 LC638 RD8 RD8 RD1 LC639 RD9 RD9 RD1 LC640 RD10 RD10 RD1 LC641 RD11 RD11 RD1 LC642 RD12 RD12 RD1 LC643 RD13 RD13 RD1 LC644 RD14 RD14 RD1 LC645 RD15 RD15 RD1 LC646 RD16 RD16 RD1 LC647 RD17 RD17 RD1 LC648 RD18 RD18 RD1 LC649 RD19 RD19 RD1 LC650 RD20 RD20 RD1 LC651 RD21 RD21 RD1 LC652 RD22 RD22 RD1 LC653 RD23 RD23 RD1 LC654 RD24 RD24 RD1 LC655 RD25 RD25 RD1 LC656 RD26 RD26 RD1 LC657 RD27 RD27 RD1 LC658 RD28 RD28 RD1 LC659 RD29 RD29 RD1 LC660 RD30 RD30 RD1 LC661 RD31 RD31 RD1 LC662 RD32 RD32 RD1 LC663 RD33 RD33 RD1 LC664 RD34 RD34 RD1 LC665 RD35 RD35 RD1 LC666 RD40 RD40 RD1 LC667 RD41 RD41 RD1 LC668 RD42 RD42 RD1 LC669 RD64 RD64 RD1 LC670 RD66 RD66 RD1 LC671 RD68 RD68 RD1 LC672 RD76 RD76 RD1 LC673 RD1 RD2 RD1 LC674 RD1 RD3 RD1 LC675 RD1 RD4 RD1 LC676 RD1 RD5 RD1 LC677 RD1 RD6 RD1 LC678 RD1 RD7 RD1 LC679 RD1 RD8 RD1 LC680 RD1 RD9 RD1 LC681 RD1 RD10 RD1 LC682 RD1 RD11 RD1 LC683 RD1 RD12 RD1 LC684 RD1 RD13 RD1 LC685 RD1 RD14 RD1 LC686 RD1 RD15 RD1 LC687 RD1 RD16 RD1 LC688 RD1 RD17 RD1 LC689 RD1 RD8 RD1 LC690 RD1 RD9 RD1 LC691 RD1 RD20 RD1 LC692 RD1 RD21 RD1 LC693 RD1 RD22 RD1 LC694 RD1 RD23 RD1 LC695 RD1 RD24 RD1 LC696 RD1 RD25 RD1 LC697 RD1 RD26 RD1 LC698 RD1 RD27 RD1 LC699 RD1 RD28 RD1 LC700 RD1 RD29 RD1 LC701 RD1 RD30 RD1 LC702 RD1 RD31 RD1 LC703 RD1 RD32 RD1 LC704 RD1 RD33 RD1 LC705 RD1 RD34 RD1 LC706 RD1 RD35 RD1 LC707 RD1 RD40 RD1 LC708 RD1 RD41 RD1 LC709 RD1 RD42 RD1 LC710 RD1 RD64 RD1 LC711 RD1 RD66 RD1 LC712 RD1 RD68 RD1 LC713 RD1 RD76 RD1 LC714 RD2 RD1 RD1 LC715 RD2 RD3 RD1 LC716 RD2 RD4 RD1 LC717 RD2 RD5 RD1 LC718 RD2 RD6 RD1 LC719 RD2 RD7 RD1 LC720 RD2 RD8 RD1 LC721 RD2 RD9 RD1 LC722 RD2 RD10 RD1 LC723 RD2 RD11 RD1 LC724 RD2 RD12 RD1 LC725 RD2 RD13 RD1 LC726 RD2 RD14 RD1 LC727 RD2 RD15 RD1 LC728 RD2 RD16 RD1 LC729 RD2 RD17 RD1 LC730 RD2 RD18 RD1 LC731 RD2 RD19 RD1 LC732 RD2 RD20 RD1 LC733 RD2 RD21 RD1 LC734 RD2 RD22 RD1 LC735 RD2 RD23 RD1 LC736 RD2 RD24 RD1 LC737 RD2 RD25 RD1 LC738 RD2 RD26 RD1 LC739 RD2 RD27 RD1 LC740 RD2 RD28 RD1 LC741 RD2 RD29 RD1 LC742 RD2 RD30 RD1 LC743 RD2 RD31 RD1 LC744 RD2 RD32 RD1 LC745 RD2 RD33 RD1 LC746 RD2 RD34 RD1 LC747 RD2 RD35 RD1 LC748 RD2 RD40 RD1 LC749 RD2 RD41 RD1 LC750 RD2 RD42 RD1 LC751 RD2 RD64 RD1 LC752 RD2 RD66 RD1 LC753 RD2 RD68 RD1 LC754 RD2 RD76 RD1 LC755 RD3 RD4 RD1 LC756 RD3 RD5 RD1 LC757 RD3 RD6 RD1 LC758 RD3 RD7 RD1 LC759 RD3 RD8 RD1 LC760 RD3 RD9 RD1 LC761 RD3 RD10 RD1 LC762 RD3 RD11 RD1 LC763 RD3 RD12 RD1 LC764 RD3 RD13 RD1 LC765 RD3 RD14 RD1 LC766 RD3 RD15 RD1 LC767 RD3 RD6 RD1 LC768 RD3 RD17 RD1 LC769 RD3 RD18 RD1 LC770 RD3 RD19 RD1 LC771 RD3 RD20 RD1 LC772 RD3 RD21 RD1 LC773 RD3 RD22 RD1 LC774 RD3 RD23 RD1 LC775 RD3 RD24 RD1 LC776 RD3 RD25 RD1 LC777 RD3 RD26 RD1 LC778 RD3 RD27 RD1 LC779 RD3 RD28 RD1 LC780 RD3 RD29 RD1 LC781 RD3 RD30 RD1 LC782 RD3 RD31 RD1 LC783 RD3 RD32 RD1 LC784 RD3 RD33 RD1 LC785 RD3 RD34 RD1 LC786 RD3 RD35 RD1 LC787 RD3 RD40 RD1 LC788 RD3 RD41 RD1 LC789 RD3 RD42 RD1 LC790 RD3 RD64 RD1 LC791 RD3 RD66 RD1 LC792 RD3 RD68 RD1 LC793 RD3 RD76 RD1 LC794 RD4 RD5 RD1 LC795 RD4 RD6 RD1 LC796 RD4 RD7 RD1 LC797 RD4 RD8 RD1 LC798 RD4 RD9 RD1 LC799 RD4 RD10 RD1 LC800 RD4 RD11 RD1 LC801 RD4 RD12 RD1 LC802 RD4 RD13 RD1 LC803 RD4 RD14 RD1 LC804 RD4 RD15 RD1 LC805 RD4 RD16 RD1 LC806 RD4 RD17 RD1 LC807 RD4 RD18 RD1 LC808 RD4 RD19 RD1 LC809 RD4 RD20 RD1 LC810 RD4 RD21 RD1 LC811 RD4 RD22 RD1 LC812 RD4 RD23 RD1 LC813 RD4 RD24 RD1 LC814 RD4 RD25 RD1 LC815 RD4 RD26 RD1 LC816 RD4 RD27 RD1 LC817 RD4 RD28 RD1 LC818 RD4 RD29 RD1 LC819 RD4 RD30 RD1 LC820 RD4 RD31 RD1 LC821 RD4 RD32 RD1 LC822 RD4 RD33 RD1 LC823 RD4 RD34 RD1 LC824 RD4 RD35 RD1 LC825 RD4 RD40 RD1 LC826 RD4 RD41 RD1 LC827 RD4 RD42 RD1 LC828 RD4 RD64 RD1 LC829 RD4 RD66 RD1 LC830 RD4 RD68 RD1 LC831 RD4 RD76 RD1 LC832 RD4 RD1 RD1 LC833 RD7 RD5 RD1 LC834 RD7 RD6 RD1 LC835 RD7 RD8 RD1 LC836 RD7 RD9 RD1 LC837 RD7 RD10 RD1 LC838 RD7 RD11 RD1 LC839 RD7 RD12 RD1 LC840 RD7 RD13 RD1 LC841 RD7 RD14 RD1 LC842 RD7 RD15 RD1 LC843 RD7 RD16 RD1 LC844 RD7 RD17 RD1 LC845 RD7 RD18 RD1 LC846 RD7 RD19 RD1 LC847 RD7 RD20 RD1 LC848 RD7 RD21 RD1 LC849 RD7 RD22 RD1 LC850 RD7 RD23 RD1 LC851 RD7 RD24 RD1 LC852 RD7 RD25 RD1 LC853 RD7 RD26 RD1 LC854 RD7 RD27 RD1 LC855 RD7 RD28 RD1 LC856 RD7 RD29 RD1 LC857 RD7 RD30 RD1 LC858 RD7 RD31 RD1 LC859 RD7 RD32 RD1 LC860 RD7 RD33 RD1 LC861 RD7 RD34 RD1 LC862 RD7 RD35 RD1 LC863 RD7 RD40 RD1 LC864 RD7 RD41 RD1 LC865 RD7 RD42 RD1 LC866 RD7 RD64 RD1 LC867 RD7 RD66 RD1 LC868 RD7 RD68 RD1 LC869 RD7 RD76 RD1 LC870 RD8 RD5 RD1 LC871 RD8 RD6 RD1 LC872 RD8 RD9 RD1 LC873 RD8 RD10 RD1 LC874 RD8 RD11 RD1 LC875 RD8 RD12 RD1 LC876 RD8 RD13 RD1 LC877 RD8 RD14 RD1 LC878 RD8 RD15 RD1 LC879 RD8 RD16 RD1 LC880 RD8 RD17 RD1 LC881 RD8 RD18 RD1 LC882 RD8 RD19 RD1 LC883 RD8 RD20 RD1 LC884 RD8 RD21 RD1 LC885 RD8 RD22 RD1 LC886 RD8 RD23 RD1 LC887 RD8 RD24 RD1 LC888 RD8 RD25 RD1 LC889 RD8 RD26 RD1 LC890 RD8 RD27 RD1 LC891 RD8 RD28 RD1 LC892 RD8 RD29 RD1 LC893 RD8 RD30 RD1 LC894 RD8 RD31 RD1 LC895 RD8 RD32 RD1 LC896 RD8 RD33 RD1 LC897 RD8 RD34 RD1 LC898 RD8 RD35 RD1 LC899 RD8 RD40 RD1 LC900 RD8 RD41 RD1 LC901 RD8 RD42 RD1 LC902 RD8 RD64 RD1 LC903 RD8 RD66 RD1 LC904 RD8 RD68 RD1 LC905 RD8 RD76 RD1 LC906 RD11 RD5 RD1 LC907 RD11 RD6 RD1 LC908 RD11 RD9 RD1 LC909 RD11 RD10 RD1 LC910 RD11 RD12 RD1 LC911 RD11 RD13 RD1 LC912 RD11 RD14 RD1 LC913 RD11 RD15 RD1 LC914 RD11 RD16 RD1 LC915 RD11 RD17 RD1 LC916 RD11 RD18 RD1 LC917 RD11 RD19 RD1 LC918 RD11 RD20 RD1 LC919 RD11 RD21 RD1 LC920 RD11 RD22 RD1 LC921 RD11 RD23 RD1 LC922 RD11 RD24 RD1 LC923 RD11 RD25 RD1 LC924 RD11 RD26 RD1 LC925 RD11 RD27 RD1 LC926 RD11 RD28 RD1 LC927 RD11 RD29 RD1 LC928 RD11 RD30 RD1 LC929 RD11 RD31 RD1 LC930 RD11 RD32 RD1 LC931 RD11 RD33 RD1 LC932 RD11 RD34 RD1 LC933 RD11 RD35 RD1 LC934 RD11 RD40 RD1 LC935 RD11 RD41 RD1 LC936 RD11 RD42 RD1 LC937 RD11 RD64 RD1 LC938 RD11 RD66 RD1 LC939 RD11 RD68 RD1 LC940 RD11 RD76 RD1 LC941 RD13 RD5 RD1 LC942 RD13 RD6 RD1 LC943 RD13 RD9 RD1 LC944 RD13 RD10 RD1 LC945 RD13 RD12 RD1 LC946 RD13 RD14 RD1 LC947 RD13 RD15 RD1 LC948 RD13 RD16 RD1 LC949 RD13 RD17 RD1 LC950 RD13 RD18 RD1 LC951 RD13 RD19 RD1 LC952 RD13 RD20 RD1 LC953 RD13 RD21 RD1 LC954 RD13 RD22 RD1 LC955 RD13 RD23 RD1 LC956 RD13 RD24 RD1 LC957 RD13 RD25 RD1 LC958 RD13 RD26 RD1 LC959 RD13 RD27 RD1 LC960 RD13 RD28 RD1 LC961 RD13 RD29 RD1 LC962 RD13 RD30 RD1 LC963 RD13 RD31 RD1 LC964 RD13 RD32 RD1 LC965 RD13 RD33 RD1 LC966 RD13 RD34 RD1 LC967 RD13 RD35 RD1 LC968 RD13 RD40 RD1 LC969 RD13 RD41 RD1 LC970 RD13 RD42 RD1 LC971 RD13 RD64 RD1 LC972 RD13 RD66 RD1 LC973 RD13 RD68 RD1 LC974 RD13 RD76 RD1 LC975 RD14 RD5 RD1 LC976 RD14 RD6 RD1 LC977 RD14 RD9 RD1 LC978 RD14 RD10 RD1 LC979 RD14 RD12 RD1 LC980 RD14 RD15 RD1 LC981 RD14 RD16 RD1 LC982 RD14 RD17 RD1 LC983 RD14 RD18 RD1 LC984 RD14 RD19 RD1 LC985 RD14 RD20 RD1 LC986 RD14 RD21 RD1 LC987 RD14 RD22 RD1 LC988 RD14 RD23 RD1 LC989 RD14 RD24 RD1 LC990 RD14 RD25 RD1 LC991 RD14 RD26 RD1 LC992 RD14 RD27 RD1 LC993 RD14 RD28 RD1 LC994 RD14 RD29 RD1 LC995 RD14 RD30 RD1 LC996 RD14 RD31 RD1 LC997 RD14 RD32 RD1 LC998 RD14 RD33 RD1 LC999 RD14 RD34 RD1 LC1000 RD14 RD35 RD1 LC1001 RD14 RD40 RD1 LC1002 RD14 RD41 RD1 LC1003 RD14 RD42 RD1 LC1004 RD14 RD64 RD1 LC1005 RD14 RD66 RD1 LC1006 RD14 RD68 RD1 LC1007 RD14 RD76 RD1 LC1008 RD22 RD5 RD1 LC1009 RD22 RD6 RD1 LC1010 RD22 RD9 RD1 LC1011 RD22 RD10 RD1 LC1012 RD22 RD12 RD1 LC1013 RD22 RD15 RD1 LC1014 RD22 RD16 RD1 LC1015 RD22 RD17 RD1 LC1016 RD22 RD18 RD1 LC1017 RD22 RD19 RD1 LC1018 RD22 RD20 RD1 LC1019 RD22 RD21 RD1 LC1020 RD22 RD23 RD1 LC1021 RD22 RD24 RD1 LC1022 RD22 RD25 RD1 LC1023 RD22 RD26 RD1 LC1024 RD22 RD27 RD1 LC1025 RD22 RD28 RD1 LC1026 RD22 RD29 RD1 LC1027 RD22 RD30 RD1 LC1028 RD22 RD31 RD1 LC1029 RD22 RD32 RD1 LC1030 RD22 RD33 RD1 LC1031 RD22 RD34 RD1 LC1032 RD22 RD35 RD1 LC1033 RD22 RD40 RD1 LC1034 RD22 RD41 RD1 LC1035 RD22 RD42 RD1 LC1036 RD22 RD64 RD1 LC1037 RD22 RD66 RD1 LC1038 RD22 RD68 RD1 LC1039 RD22 RD76 RD1 LC1040 RD26 RD5 RD1 LC1041 RD26 RD6 RD1 LC1042 RD26 RD9 RD1 LC1043 RD26 RD10 RD1 LC1044 RD26 RD12 RD1 LC1045 RD26 RD15 RD1 LC1046 RD26 RD16 RD1 LC1047 RD26 RD17 RD1 LC1048 RD26 RD18 RD1 LC1049 RD26 RD19 RD1 LC1050 RD26 RD20 RD1 LC1051 RD26 RD21 RD1 LC1052 RD26 RD23 RD1 LC1053 RD26 RD24 RD1 LC1054 RD26 RD25 RD1 LC1055 RD26 RD27 RD1 LC1056 RD26 RD28 RD1 LC1057 RD26 RD29 RD1 LC1058 RD26 RD30 RD1 LC1059 RD26 RD31 RD1 LC1060 RD26 RD32 RD1 LC1061 RD26 RD33 RD1 LC1062 RD26 RD34 RD1 LC1063 RD26 RD35 RD1 LC1064 RD26 RD40 RD1 LC1065 RD26 RD41 RD1 LC1066 RD26 RD42 RD1 LC1067 RD26 RD64 RD1 LC1068 RD26 RD66 RD1 LC1069 RD26 RD68 RD1 LC1070 RD26 RD76 RD1 LC1071 RD35 RD5 RD1 LC1072 RD35 RD6 RD1 LC1073 RD35 RD9 RD1 LC1074 RD35 RD10 RD1 LC1075 RD35 RD12 RD1 LC1076 RD35 RD15 RD1 LC1077 RD35 RD16 RD1 LC1078 RD35 RD17 RD1 LC1079 RD35 RD18 RD1 LC1080 RD35 RD19 RD1 LC1081 RD35 RD20 RD1 LC1082 RD35 RD21 RD1 LC1083 RD35 RD23 RD1 LC1084 RD35 RD24 RD1 LC1085 RD35 RD25 RD1 LC1086 RD35 RD27 RD1 LC1087 RD35 RD28 RD1 LC1088 RD35 RD29 RD1 LC1089 RD35 RD30 RD1 LC1090 RD35 RD31 RD1 LC1091 RD35 RD32 RD1 LC1092 RD35 RD33 RD1 LC1093 RD35 RD34 RD1 LC1094 RD35 RD40 RD1 LC1095 RD35 RD41 RD1 LC1096 RD35 RD42 RD1 LC1097 RD35 RD64 RD1 LC1098 RD35 RD66 RD1 LC1099 RD35 RD68 RD1 LC1100 RD35 RD76 RD1 LC1101 RD40 RD5 RD1 LC1102 RD40 RD6 RD1 LC1103 RD40 RD9 RD1 LC1104 RD40 RD10 RD1 LC1105 RD40 RD12 RD1 LC1106 RD40 RD15 RD1 LC1107 RD40 RD16 RD1 LC1108 RD40 RD17 RD1 LC1109 RD40 RD8 RD1 LC1110 RD40 RD9 RD1 LC1111 RD40 RD20 RD1 LC1112 RD40 RD21 RD1 LC1113 RD40 RD23 RD1 LC1114 RD40 RD24 RD1 LC1115 RD40 RD25 RD1 LC1116 RD40 RD27 RD1 LC1117 RD40 RD28 RD1 LC1118 RD40 RD29 RD1 LC1119 RD40 RD30 RD1 LC1120 RD40 RD31 RD1 LC1121 RD40 RD32 RD1 LC1122 RD40 RD33 RD1 LC1123 RD40 RD34 RD1 LC1124 RD40 RD41 RD1 LC1125 RD40 RD42 RD1 LC1126 RD40 RD64 RD1 LC1127 RD40 RD66 RD1 LC1128 RD40 RD68 RD1 LC1129 RD40 RD76 RD1 LC1130 RD41 RD5 RD1 LC1131 RD41 RD6 RD1 LC1132 RD41 RD9 RD1 LC1133 RD41 RD10 RD1 LC1134 RD41 RD12 RD1 LC1135 RD41 RD15 RD1 LC1136 RD41 RD16 RD1 LC1137 RD41 RD17 RD1 LC1138 RD41 RD18 RD1 LC1139 RD41 RD19 RD1 LC1140 RD41 RD20 RD1 LC1141 RD41 RD21 RD1 LC1142 RD41 RD23 RD1 LC1143 RD41 RD24 RD1 LC1144 RD41 RD25 RD1 LC1145 RD41 RD27 RD1 LC1146 RD41 RD28 RD1 LC1147 RD41 RD29 RD1 LC1148 RD41 RD30 RD1 LC1149 RD41 RD31 RD1 LC1150 RD41 RD32 RD1 LC1151 RD41 RD33 RD1 LC1152 RD41 RD34 RD1 LC1153 RD41 RD42 RD1 LC1154 RD41 RD64 RD1 LC1155 RD41 RD66 RD1 LC1156 RD41 RD68 RD1 LC1157 RD41 RD76 RD1 LC1158 RD64 RD5 RD1 LC1159 RD64 RD6 RD1 LC1160 RD64 RD9 RD1 LC1161 RD64 RD10 RD1 LC1162 RD64 RD12 RD1 LC1163 RD64 RD15 RD1 LC1164 RD64 RD16 RD1 LC1165 RD64 RD17 RD1 LC1166 RD64 RD18 RD1 LC1167 RD64 RD19 RD1 LC1168 RD64 RD20 RD1 LC1169 RD64 RD21 RD1 LC1170 RD64 RD23 RD1 LC1171 RD64 RD24 RD1 LC1172 RD64 RD25 RD1 LC1173 RD64 RD27 RD1 LC1174 RD64 RD28 RD1 LC1175 RD64 RD29 RD1 LC1176 RD64 RD30 RD1 LC1177 RD64 RD31 RD1 LC1178 RD64 RD32 RD1 LC1179 RD64 RD33 RD1 LC1180 RD64 RD34 RD1 LC1181 RD64 RD42 RD1 LC1182 RD64 RD64 RD1 LC1183 RD64 RD66 RD1 LC1184 RD64 RD68 RD1 LC1185 RD64 RD76 RD1 LC1186 RD66 RD5 RD1 LC1187 RD66 RD6 RD1 LC1188 RD66 RD9 RD1 LC1189 RD66 RD10 RD1 LC1190 RD66 RD12 RD1 LC1191 RD66 RD15 RD1 LC1192 RD66 RD16 RD1 LC1193 RD66 RD17 RD1 LC1194 RD66 RD18 RD1 LC1195 RD66 RD19 RD1 LC1196 RD66 RD20 RD1 LC1197 RD66 RD21 RD1 LC1198 RD66 RD23 RD1 LC1199 RD66 RD24 RD1 LC1200 RD66 RD25 RD1 LC1201 RD66 RD27 RD1 LC1202 RD66 RD28 RD1 LC1203 RD66 RD29 RD1 LC1204 RD66 RD30 RD1 LC1205 RD66 RD31 RD1 LC1206 RD66 RD32 RD1 LC1207 RD66 RD33 RD1 LC1208 RD66 RD34 RD1 LC1209 RD66 RD42 RD1 LC1210 RD66 RD68 RD1 LC1211 RD66 RD76 RD1 LC1212 RD68 RD5 RD1 LC1213 RD68 RD6 RD1 LC1214 RD68 RD9 RD1 LC1215 RD68 RD10 RD1 LC1216 RD68 RD12 RD1 LC1217 RD68 RD15 RD1 LC1218 RD68 RD16 RD1 LC1219 RD68 RD17 RD1 LC1220 RD68 RD18 RD1 LC1221 RD68 RD19 RD1 LC1222 RD68 RD20 RD1 LC1223 RD68 RD21 RD1 LC1224 RD68 RD23 RD1 LC1225 RD68 RD24 RD1 LC1226 RD68 RD25 RD1 LC1227 RD68 RD27 RD1 LC1228 RD68 RD28 RD1 LC1229 RD68 RD29 RD1 LC1230 RD68 RD30 RD1 LC1231 RD68 RD31 RD1 LC1232 RD68 RD32 RD1 LC1233 RD68 RD33 RD1 LC1234 RD68 RD34 RD1 LC1235 RD68 RD42 RD1 LC1236 RD68 RD76 RD1 LC1237 RD76 RD5 RD1 LC1238 RD76 RD6 RD1 LC1239 RD76 RD9 RD1 LC1240 RD76 RD10 RD1 LC1241 RD76 RD12 RD1 LC1242 RD76 RD15 RD1 LC1243 RD76 RD16 RD1 LC1244 RD76 RD17 RD1 LC1245 RD76 RD18 RD1 LC1246 RD76 RD19 RD1 LC1247 RD76 RD20 RD1 LC1248 RD76 RD21 RD1 LC1249 RD76 RD23 RD1 LC1250 RD76 RD24 RD1 LC1251 RD76 RD25 RD1 LC1252 RD76 RD27 RD1 LC1253 RD76 RD28 RD1 LC1254 RD76 RD29 RD1 LC1255 RD76 RD30 RD1 LC1256 RD76 RD31 RD1 LC1257 RD76 RD32 RD1 LC1258 RD76 RD33 RD1 LC1259 RD76 RD34 RD1 LC1260 RD76 RD42 RD1,
wherein RD1 to RD21 have the following structures
Figure US20240025934A1-20240125-C00365
Figure US20240025934A1-20240125-C00366
Figure US20240025934A1-20240125-C00367
Figure US20240025934A1-20240125-C00368
Figure US20240025934A1-20240125-C00369
Figure US20240025934A1-20240125-C00370
Figure US20240025934A1-20240125-C00371
Figure US20240025934A1-20240125-C00372
Figure US20240025934A1-20240125-C00373
14. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, a compound comprising:
a ligand LA of Formula I
Figure US20240025934A1-20240125-C00374
wherein ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring;
wherein each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution;
wherein each RA, RB, and RC is independently a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA has the formula —CH2R or —CHRR′;
wherein each R and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
wherein LA is complexed to a metal M;
wherein M is optionally coordinated to other ligands;
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein any two substituents of RB and RC may be joined or fused together to form a ring.
15. The OLED of claim 14, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
16. The OLED of claim 14, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
17. The OLED of claim 16, wherein the host is selected from the group consisting of:
Figure US20240025934A1-20240125-C00375
Figure US20240025934A1-20240125-C00376
Figure US20240025934A1-20240125-C00377
Figure US20240025934A1-20240125-C00378
Figure US20240025934A1-20240125-C00379
Figure US20240025934A1-20240125-C00380
and combinations thereof.
18. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising:
a ligand LA of Formula I
Figure US20240025934A1-20240125-C00381
wherein ring C is a 5-membered or a 6-membered carbocyclic or heterocyclic ring;
wherein each RA, RB, and RC independently represents mono to the maximum allowable number of substitutions, or no substitution;
wherein each RA, RB, and RC is independently a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA has the formula —CH2R or —CHRR′;
wherein each R and R′ is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
wherein LA is complexed to a metal M;
wherein M is optionally coordinated to other ligands;
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein any two substituents of RB and RC may be joined or fused together to form a ring.
19. A formulation comprising a compound according to claim 1.
20. A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises a compound of claim 1 or a monovalent or polyvalent variant thereof.
US18/357,242 2018-07-11 2023-07-24 Organic electroluminescent materials and devices Pending US20240025934A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US18/357,242 US20240025934A1 (en) 2018-07-11 2023-07-24 Organic electroluminescent materials and devices

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862696383P 2018-07-11 2018-07-11
US16/442,839 US11753425B2 (en) 2018-07-11 2019-06-17 Organic electroluminescent materials and devices
US18/357,242 US20240025934A1 (en) 2018-07-11 2023-07-24 Organic electroluminescent materials and devices

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US16/442,839 Continuation US11753425B2 (en) 2018-07-11 2019-06-17 Organic electroluminescent materials and devices

Publications (1)

Publication Number Publication Date
US20240025934A1 true US20240025934A1 (en) 2024-01-25

Family

ID=69140110

Family Applications (2)

Application Number Title Priority Date Filing Date
US16/442,839 Active 2040-03-28 US11753425B2 (en) 2018-07-11 2019-06-17 Organic electroluminescent materials and devices
US18/357,242 Pending US20240025934A1 (en) 2018-07-11 2023-07-24 Organic electroluminescent materials and devices

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US16/442,839 Active 2040-03-28 US11753425B2 (en) 2018-07-11 2019-06-17 Organic electroluminescent materials and devices

Country Status (4)

Country Link
US (2) US11753425B2 (en)
JP (2) JP2020007302A (en)
KR (1) KR20200006935A (en)
CN (1) CN110713498A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113292579A (en) * 2020-02-24 2021-08-24 环球展览公司 Organic electroluminescent material and device

Family Cites Families (132)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769292A (en) 1987-03-02 1988-09-06 Eastman Kodak Company Electroluminescent device with modified thin film luminescent zone
GB8909011D0 (en) 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
EP0650955B1 (en) 1993-11-01 1998-08-19 Hodogaya Chemical Co., Ltd. Amine compound and electro-luminescence device comprising same
US5707745A (en) 1994-12-13 1998-01-13 The Trustees Of Princeton University Multicolor organic light emitting devices
US5703436A (en) 1994-12-13 1997-12-30 The Trustees Of Princeton University Transparent contacts for organic devices
US6939625B2 (en) 1996-06-25 2005-09-06 Nôrthwestern University Organic light-emitting diodes and methods for assembly and enhanced charge injection
US5844363A (en) 1997-01-23 1998-12-01 The Trustees Of Princeton Univ. Vacuum deposited, non-polymeric flexible organic light emitting devices
US6013982A (en) 1996-12-23 2000-01-11 The Trustees Of Princeton University Multicolor display devices
US6091195A (en) 1997-02-03 2000-07-18 The Trustees Of Princeton University Displays having mesa pixel configuration
US5834893A (en) 1996-12-23 1998-11-10 The Trustees Of Princeton University High efficiency organic light emitting devices with light directing structures
US6303238B1 (en) 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
US6337102B1 (en) 1997-11-17 2002-01-08 The Trustees Of Princeton University Low pressure vapor phase deposition of organic thin films
US6087196A (en) 1998-01-30 2000-07-11 The Trustees Of Princeton University Fabrication of organic semiconductor devices using ink jet printing
US6528187B1 (en) 1998-09-08 2003-03-04 Fuji Photo Film Co., Ltd. Material for luminescence element and luminescence element using the same
US6830828B2 (en) 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6097147A (en) 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
US6294398B1 (en) 1999-11-23 2001-09-25 The Trustees Of Princeton University Method for patterning devices
US6458475B1 (en) 1999-11-24 2002-10-01 The Trustee Of Princeton University Organic light emitting diode having a blue phosphorescent molecule as an emitter
KR100377321B1 (en) 1999-12-31 2003-03-26 주식회사 엘지화학 Electronic device comprising organic compound having p-type semiconducting characteristics
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
JP2002050860A (en) 2000-08-04 2002-02-15 Toray Eng Co Ltd Method and device for mounting
US6579630B2 (en) 2000-12-07 2003-06-17 Canon Kabushiki Kaisha Deuterated semiconducting organic compounds used for opto-electronic devices
JP3812730B2 (en) 2001-02-01 2006-08-23 富士写真フイルム株式会社 Transition metal complex and light emitting device
JP4307000B2 (en) 2001-03-08 2009-08-05 キヤノン株式会社 Metal coordination compound, electroluminescent element and display device
JP4310077B2 (en) 2001-06-19 2009-08-05 キヤノン株式会社 Metal coordination compound and organic light emitting device
WO2003001616A2 (en) 2001-06-20 2003-01-03 Showa Denko K.K. Light emitting material and organic light-emitting device
US7071615B2 (en) 2001-08-20 2006-07-04 Universal Display Corporation Transparent electrodes
US7250226B2 (en) 2001-08-31 2007-07-31 Nippon Hoso Kyokai Phosphorescent compound, a phosphorescent composition and an organic light-emitting device
US7431968B1 (en) 2001-09-04 2008-10-07 The Trustees Of Princeton University Process and apparatus for organic vapor jet deposition
US6835469B2 (en) 2001-10-17 2004-12-28 The University Of Southern California Phosphorescent compounds and devices comprising the same
US7166368B2 (en) 2001-11-07 2007-01-23 E. I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
US6863997B2 (en) 2001-12-28 2005-03-08 The Trustees Of Princeton University White light emitting OLEDs from combined monomer and aggregate emission
KR100691543B1 (en) 2002-01-18 2007-03-09 주식회사 엘지화학 New material for transporting electron and organic electroluminescent display using the same
US20030230980A1 (en) 2002-06-18 2003-12-18 Forrest Stephen R Very low voltage, high efficiency phosphorescent oled in a p-i-n structure
US7189989B2 (en) 2002-08-22 2007-03-13 Fuji Photo Film Co., Ltd. Light emitting element
AU2003261758A1 (en) 2002-08-27 2004-03-19 Fujitsu Limited Organometallic complexes, organic el devices, and organic el displays
US6687266B1 (en) 2002-11-08 2004-02-03 Universal Display Corporation Organic light emitting materials and devices
JP4365199B2 (en) 2002-12-27 2009-11-18 富士フイルム株式会社 Organic electroluminescence device
JP4365196B2 (en) 2002-12-27 2009-11-18 富士フイルム株式会社 Organic electroluminescence device
KR101391117B1 (en) 2003-03-24 2014-04-30 유니버시티 오브 써던 캘리포니아 Phenyl-pyrazole complexes of ir
US7090928B2 (en) 2003-04-01 2006-08-15 The University Of Southern California Binuclear compounds
KR101162933B1 (en) 2003-04-15 2012-07-05 메르크 파텐트 게엠베하 Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
US7029765B2 (en) 2003-04-22 2006-04-18 Universal Display Corporation Organic light emitting devices having reduced pixel shrinkage
KR101032355B1 (en) 2003-05-29 2011-05-03 신닛테츠가가쿠 가부시키가이샤 Organic electroluminescent element
JP2005011610A (en) 2003-06-18 2005-01-13 Nippon Steel Chem Co Ltd Organic electroluminescent element
US20050025993A1 (en) 2003-07-25 2005-02-03 Thompson Mark E. Materials and structures for enhancing the performance of organic light emitting devices
TWI390006B (en) 2003-08-07 2013-03-21 Nippon Steel Chemical Co Organic EL materials with aluminum clamps
DE10338550A1 (en) 2003-08-19 2005-03-31 Basf Ag Transition metal complexes with carbene ligands as emitters for organic light-emitting diodes (OLEDs)
US20060269780A1 (en) 2003-09-25 2006-11-30 Takayuki Fukumatsu Organic electroluminescent device
JP4822687B2 (en) 2003-11-21 2011-11-24 富士フイルム株式会社 Organic electroluminescence device
US7332232B2 (en) 2004-02-03 2008-02-19 Universal Display Corporation OLEDs utilizing multidentate ligand systems
KR100882172B1 (en) 2004-03-11 2009-02-06 미쓰비시 가가꾸 가부시키가이샤 Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same, and method for manufacturing organic electroluminescent device and method for producing charge-transporting film
TW200531592A (en) 2004-03-15 2005-09-16 Nippon Steel Chemical Co Organic electroluminescent device
JP4869565B2 (en) 2004-04-23 2012-02-08 富士フイルム株式会社 Organic electroluminescence device
US7491823B2 (en) 2004-05-18 2009-02-17 The University Of Southern California Luminescent compounds with carbene ligands
US7393599B2 (en) 2004-05-18 2008-07-01 The University Of Southern California Luminescent compounds with carbene ligands
US7445855B2 (en) 2004-05-18 2008-11-04 The University Of Southern California Cationic metal-carbene complexes
US7534505B2 (en) 2004-05-18 2009-05-19 The University Of Southern California Organometallic compounds for use in electroluminescent devices
US7154114B2 (en) 2004-05-18 2006-12-26 Universal Display Corporation Cyclometallated iridium carbene complexes for use as hosts
US7279704B2 (en) 2004-05-18 2007-10-09 The University Of Southern California Complexes with tridentate ligands
WO2005123873A1 (en) 2004-06-17 2005-12-29 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
EP1893718B1 (en) 2004-06-28 2018-10-03 UDC Ireland Limited Electroluminescent metal complexes with triazoles and benotriazoles
US20060008670A1 (en) 2004-07-06 2006-01-12 Chun Lin Organic light emitting materials and devices
WO2006009024A1 (en) 2004-07-23 2006-01-26 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
DE102004057072A1 (en) 2004-11-25 2006-06-01 Basf Ag Use of Transition Metal Carbene Complexes in Organic Light Emitting Diodes (OLEDs)
EP1859656B1 (en) 2004-12-30 2013-07-17 E.I. Du Pont De Nemours And Company Organometallic complexes
WO2006082742A1 (en) 2005-02-04 2006-08-10 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
KR100803125B1 (en) 2005-03-08 2008-02-14 엘지전자 주식회사 Red phosphorescent compounds and organic electroluminescence devices using the same
JP5125502B2 (en) 2005-03-16 2013-01-23 コニカミノルタホールディングス株式会社 Organic electroluminescence element material, organic electroluminescence element
DE102005014284A1 (en) 2005-03-24 2006-09-28 Basf Ag Use of compounds containing aromatic or heteroaromatic rings containing groups via carbonyl groups as matrix materials in organic light-emitting diodes
WO2006103874A1 (en) 2005-03-29 2006-10-05 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
GB2439030B (en) 2005-04-18 2011-03-02 Konica Minolta Holdings Inc Organic electroluminescent device, display and illuminating device
US7807275B2 (en) 2005-04-21 2010-10-05 Universal Display Corporation Non-blocked phosphorescent OLEDs
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US9051344B2 (en) 2005-05-06 2015-06-09 Universal Display Corporation Stability OLED materials and devices
JP4533796B2 (en) 2005-05-06 2010-09-01 富士フイルム株式会社 Organic electroluminescence device
EP1888708B1 (en) 2005-05-31 2012-11-21 Universal Display Corporation Triphenylene hosts in phosphorescent light emitting diodes
KR101010846B1 (en) 2005-06-07 2011-01-25 신닛테츠가가쿠 가부시키가이샤 Organic metal complex and organic electroluminescent device using same
US7638072B2 (en) 2005-06-27 2009-12-29 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
JP5076891B2 (en) 2005-07-01 2012-11-21 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
WO2007028417A1 (en) 2005-09-07 2007-03-15 Technische Universität Braunschweig Triplett emitter having condensed five-membered rings
JP4887731B2 (en) 2005-10-26 2012-02-29 コニカミノルタホールディングス株式会社 Organic electroluminescence element, display device and lighting device
WO2007063754A1 (en) 2005-12-01 2007-06-07 Nippon Steel Chemical Co., Ltd. Compound for organic electroluminescent element and organic electroluminescent element
US20090295276A1 (en) 2005-12-01 2009-12-03 Tohru Asari Organic Electroluminescent Device
KR102103062B1 (en) 2006-02-10 2020-04-22 유니버셜 디스플레이 코포레이션 METAL COMPLEXES OF CYCLOMETALLATED IMIDAZO[1,2-f]PHENANTHRIDINE AND DIIMIDAZO[1,2-A:1',2'-C]QUINAZOLINE LIGANDS AND ISOELECTRONIC AND BENZANNULATED ANALOGS THEREOF
JP4823730B2 (en) 2006-03-20 2011-11-24 新日鐵化学株式会社 Luminescent layer compound and organic electroluminescent device
JP4994688B2 (en) 2006-03-27 2012-08-08 昭和電工株式会社 Organic light emitting device using compound having carrier transport property and phosphorescent property
CN101432272B (en) 2006-04-26 2013-02-27 出光兴产株式会社 Aromatic amine derivative and organic electroluminescent element using same
JP5432523B2 (en) 2006-05-11 2014-03-05 出光興産株式会社 Organic electroluminescence device
JP5081821B2 (en) 2006-06-02 2012-11-28 出光興産株式会社 Material for organic electroluminescence device and organic electroluminescence device using the same
JP5139297B2 (en) 2006-08-23 2013-02-06 出光興産株式会社 Aromatic amine derivatives and organic electroluminescence devices using them
JP5589251B2 (en) 2006-09-21 2014-09-17 コニカミノルタ株式会社 Organic electroluminescence element material
JP4388590B2 (en) 2006-11-09 2009-12-24 新日鐵化学株式会社 Compound for organic electroluminescence device and organic electroluminescence device
EP2085382B1 (en) 2006-11-24 2016-04-20 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
US8119255B2 (en) 2006-12-08 2012-02-21 Universal Display Corporation Cross-linkable iridium complexes and organic light-emitting devices using the same
US8778508B2 (en) 2006-12-08 2014-07-15 Universal Display Corporation Light-emitting organometallic complexes
DE602008004738D1 (en) 2007-02-23 2011-03-10 Basf Se ELECTROLUMINESCENT METAL COMPLEXES WITH BENZOTRIAZOLENE
JP5677836B2 (en) 2007-04-26 2015-02-25 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Silanes containing phenothiazine-S-oxide or phenothiazine-S, S-dioxide groups and their use in OLEDs
WO2008156879A1 (en) 2007-06-20 2008-12-24 Universal Display Corporation Blue phosphorescent imidazophenanthridine materials
CN101720330B (en) 2007-06-22 2017-06-09 Udc爱尔兰有限责任公司 Light emitting cu (I) complex compound
KR101577465B1 (en) 2007-07-05 2015-12-14 바스프 에스이 Organic light-emitting diodes comprising carbene-transition metal complex emitters, and at least one compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophene s-oxides and disilyldibenzothiophene s,s-dioxides
JP5295957B2 (en) 2007-07-07 2013-09-18 出光興産株式会社 Naphthalene derivative, material for organic EL element, and organic EL element using the same
WO2009008205A1 (en) 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and material for organic electroluminescent device
US8221907B2 (en) 2007-07-07 2012-07-17 Idemitsu Kosan Co., Ltd. Chrysene derivative and organic electroluminescent device using the same
US8779655B2 (en) 2007-07-07 2014-07-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
US20090045731A1 (en) 2007-07-07 2009-02-19 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
WO2009008100A1 (en) 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element prepared by using the material
US8080658B2 (en) 2007-07-10 2011-12-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent element and organic electroluminescent element employing the same
WO2009018009A1 (en) 2007-07-27 2009-02-05 E. I. Du Pont De Nemours And Company Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles
EP3159333B1 (en) 2007-08-08 2020-04-22 Universal Display Corporation Benzo-fused thiophene or furan compounds comprising a triphenylene group
JP2009040728A (en) 2007-08-09 2009-02-26 Canon Inc Organometallic complex and organic light-emitting element using the same
KR101642030B1 (en) 2007-10-17 2016-07-25 바스프 에스이 Transition metal complexes comprising bridged carbene ligands and the use thereof in oleds
US20090101870A1 (en) 2007-10-22 2009-04-23 E. I. Du Pont De Nemours And Company Electron transport bi-layers and devices made with such bi-layers
US7914908B2 (en) 2007-11-02 2011-03-29 Global Oled Technology Llc Organic electroluminescent device having an azatriphenylene derivative
DE102007053771A1 (en) 2007-11-12 2009-05-14 Merck Patent Gmbh Organic electroluminescent devices
US8222637B2 (en) 2007-11-15 2012-07-17 Idemitsu Kosan Co., Ltd. Benzochrysene derivative and organic electroluminescence device using the same
EP2221897A4 (en) 2007-11-22 2012-08-08 Idemitsu Kosan Co Organic el element and solution containing organic el material
US8759819B2 (en) 2007-11-22 2014-06-24 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
WO2009100991A1 (en) 2008-02-12 2009-08-20 Basf Se Electroluminescent metal complexes with dibenzo[f,h]quinoxalines
TWI532822B (en) 2011-04-29 2016-05-11 半導體能源研究所股份有限公司 Light-emitting device, electronic device, and lighting device utilizing phosphorescence
TWI455942B (en) 2011-12-23 2014-10-11 Semiconductor Energy Lab Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
KR20150022529A (en) * 2013-08-23 2015-03-04 삼성디스플레이 주식회사 Organic light emitting device
US9929353B2 (en) * 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) * 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US9397302B2 (en) * 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
KR20160109596A (en) 2015-03-12 2016-09-21 고려대학교 산학협력단 Metal complex for dopant of a light emitting layer and blue phosphorescent organic light emitting device comprising the same
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11744141B2 (en) * 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
KR102125962B1 (en) * 2018-01-17 2020-06-23 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same

Also Published As

Publication number Publication date
KR20200006935A (en) 2020-01-21
JP2024014870A (en) 2024-02-01
US20200017536A1 (en) 2020-01-16
US11753425B2 (en) 2023-09-12
CN110713498A (en) 2020-01-21
JP2020007302A (en) 2020-01-16

Similar Documents

Publication Publication Date Title
US11239434B2 (en) Organic electroluminescent materials and devices
US11697662B2 (en) Organic electroluminescent materials and devices
US10862055B2 (en) Organic electroluminescent materials and devices
EP3613751B1 (en) Organic electroluminescent materials and devices
US11839141B2 (en) Organic electroluminescent materials and devices
US20230354692A1 (en) Organic electroluminescent materials and devices
US11844267B2 (en) Organic electroluminescent materials and devices
US20210095196A1 (en) Organic electroluminescent materials and devices
US20240025934A1 (en) Organic electroluminescent materials and devices
US20210217970A1 (en) Organic electroluminescent materials and devices
US11937503B2 (en) Organic electroluminescent materials and devices
US20230257407A1 (en) Organic electroluminescent materials and devices
US11925103B2 (en) Organic electroluminescent materials and devices
US20230092059A1 (en) Organic electroluminescent materials and devices
US20220275013A1 (en) Organic electroluminescent materials and devices
US11296283B2 (en) Organic electroluminescent materials and devices
US11459349B2 (en) Organic electroluminescent materials and devices
US11623936B2 (en) Organic electroluminescent materials and devices
US11827651B2 (en) Organic electroluminescent materials and devices
US20220194974A1 (en) Organic electroluminescent materials and devices
US20230263048A1 (en) Organic electroluminescent materials and devices

Legal Events

Date Code Title Description
AS Assignment

Owner name: UNIVERSAL DISPLAY CORPORATION, NEW JERSEY

Free format text: NUNC PRO TUNC ASSIGNMENT;ASSIGNORS:BOUDREAULT, PIERRE-LUC T.;MARGULIES, ERIC A.;ALLEYNE, BERT;SIGNING DATES FROM 20190612 TO 20190617;REEL/FRAME:064352/0556

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION