Organic electroluminescent materials and devices

Abstract

To provide a metal complex having a ligand useful in a light-emitting dopant of a red color, and provide a good external quantum efficiency, a good color, and a long life to an organic light-emitting device (OLED).SOLUTION: The present invention provides an organic layer containing a chemical compound that contains ligand LA expressed by the following structural formula (I), and a host.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The claimed invention was made by, for the benefit of, and / or in connection with one or more of the following parties to a university-corporation collaborative research agreement: University of Michigan, Princeton University, University of Southern California, and the Regents of Universal Display Corporation, which agreement was in effect on or before the date the claimed invention was made, and the claimed invention was made as a result of activities conducted within the scope of said agreement.

[0002] The present invention relates to metal complexes with novel ligands. The compounds are useful in organic light-emitting devices (OLEDs), particularly as emissive dopants. The incorporation of these novel ligands provides red phosphorescent materials with good external quantum efficiency, good color, and long lifetime. [Background technology]

[0003] Optoelectronic devices that utilize organic materials are becoming increasingly desirable for several reasons. Because many of the materials used to fabricate such devices are relatively inexpensive, organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as flexibility, may make them well suited for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting devices, organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic light-emitting layer emits light can generally be easily tuned with appropriate dopants.

[0004] OLEDs utilize thin organic films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Patent Nos. 5,623,999; 5,723,999; and 5,723,999, which are incorporated herein by reference in their entireties.

[0005] One application of phosphorescent molecules is in full-color displays. Industry standards for such displays require pixels adapted to emit specific colors, referred to as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Color can be measured using CIE coordinates, which are well known in the art.

[0006] An example of a green emitting molecule has the following structure: [ka] The compound is tris(2-phenylpyridine)iridium, denoted as Ir(ppy)3, having the formula:

[0007] In this figure and later figures herein, we depict the coordination bond from nitrogen to the metal (here Ir) as a straight line.

[0008] As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" can actually be quite large. Small molecules can contain repeating 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 can be incorporated into polymers, for example, as pendant groups on a polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of dendrimers, which consist of a series of chemical shells built on the core moiety. The core moiety of a dendrimer can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

[0009] As used herein, "top" means furthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as "disposed over" a second layer, the first layer is disposed further from the substrate. There may be other layers between the first and second layers, 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 may be various organic layers in between.

[0010] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium, either in the form of a solution or suspension.

[0011] A ligand may be referred to as "photoactive" if it is considered to directly contribute to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" if it is considered not to contribute to the photoactive properties of the emissive material, although the ancillary ligand may modify the properties of the photoactive ligand.

[0012] As used herein, and as would generally be understood by one of ordinary skill 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. Because ionization potentials (IPs) are measured as negative energies relative to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram, with the vacuum 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.

[0013] As used herein, and as will generally be understood by those 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 being farther 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.

[0014] Further details on OLEDs and the above definitions can be found in US Pat. No. 6,223,999, which is incorporated herein by reference in its entirety. Summary of the Invention

[0015] The present invention provides compounds comprising metal complexes having novel ligand structures, which can be used in organic light-emitting devices, and in particular, can be useful as phosphorescent dopants in such devices.

[0016] The present invention provides a ligand L represented by the following formula (I): A The present invention provides a compound comprising: [ka] wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where: The wavy line represents the bond to ring B; R 1 and R 3 each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted, or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of is nitrogen; Y 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3, R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; Said L A is coordinated to the metal M, Said L A optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; The M is optionally coordinated to another ligand.

[0017] In some embodiments, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

[0018] In some embodiments, M is Ir.

[0019] In some embodiments, Y 1 is selected from the group consisting of NR', O, S, and CR'R''.

[0020] In some embodiments, Y 1 is O.

[0021] In some embodiments, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 One of them is nitrogen.

[0022] In some embodiments, X 1 , X2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 Two of them are nitrogen.

[0023] In some embodiments, X 1 , X 2 , X 3 , and X 4 One of the is nitrogen; X 5 , X 6 , X 7 , and X 8 One of them is nitrogen.

[0024] In some embodiments, X 1 , X 2 , X 3 , and X 4 One of the is nitrogen; X 5 , X 6 , X 7 , and X 8 is carbon.

[0025] In some embodiments, X 2 is nitrogen; X 1 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is carbon.

[0026] In some embodiments, A is phenyl.

[0027] In some embodiments, L A teeth, [ka] is selected from the group consisting of:

[0028] In some embodiments, the compound is a compound represented by formula (III-A): [ka] (In the formula, L B is a bidentate ligand and n is 1, 2, or 3.

[0029] In some embodiments, L A L A1 ~L A960 is selected from the group consisting of:

[0030] In some embodiments, L B L B1 ~L B41 is selected from the group consisting of:

[0031] In some embodiments, L B L B42 ~L B45 is selected from the group consisting of:

[0032] In some embodiments, the compound has the formula (IV): [ka] and is selected from the group consisting of Compound 1 to Compound 960 listed in Table 1.

[0033] In some embodiments, the compound has the formula (V): [ka] and is selected from the group consisting of Compounds 961 to 5760 listed in Table 2.

[0034] In some embodiments, the compound has the formula (VI): [ka] and is selected from the group consisting of Compounds 5761 to 7680 listed in Table 3.

[0035] In some embodiments, the compound is [ka] is selected from the group consisting of:

[0036] The present invention also provides an organic light-emitting device, comprising: an anode; a cathode; an organic layer disposed between the anode and the cathode; The organic layer contains a ligand L represented by the following formula (I): A The compound includes: [ka] wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where: The wavy line represents the bond to ring B; R 1 and R 3 each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted, or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5, X 6 , X 7 , and X 8 at least one of is nitrogen; Y 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; Said L A is coordinated to the metal M, Said L A is optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; The M is optionally coordinated to other ligands.

[0037] The present invention also provides a ligand L represented by the following formula (I): A A composition comprising a compound comprising: [ka] wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where: The wavy line represents the bond to ring B; R 1 and R 3each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted, or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of is nitrogen; Y 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; Said L A is coordinated to the metal M, Said L A optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; The M is optionally coordinated to another ligand. [Brief explanation of the drawings]

[0038] The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and, together with the description, serve to further explain the principles of the invention and to enable one skilled in the relevant art to make and use the invention.

[0039] [Figure 1] FIG. 1 shows an organic light-emitting device.

[0040] [Figure 2] FIG. 2 shows an inverted organic light-emitting device that does not have a separate electron transport layer.

[0041] [Figure 3] FIG. 3 shows a compound of formula (IA). DETAILED DESCRIPTION OF THE INVENTION

[0042] 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 migrate to the oppositely charged electrode, respectively. When an electron and hole localize on the same molecule, an "exciton," a localized electron-hole pair with an excited energy state, is formed. Light is emitted via a photoemissive mechanism when the exciton relaxes. In some cases, the exciton may be localized on an excimer or exciplex. Non-radiative mechanisms, such as thermal relaxation, can also occur but are generally considered undesirable.

[0043] Early OLEDs used emissive molecules that emitted light from their singlet state ("fluorescence"), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a time frame of less than 10 nanoseconds.

[0044] More recently, OLEDs have been demonstrated that have emissive materials that emit light from triplet states ("phosphorescence"). Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Vol. 395, No. 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"), which are incorporated by reference in their entireties. Phosphorescence is described in further detail in U.S. Pat. No. 7,279,704, columns 5-6, which are incorporated by reference.

[0045] FIG. 1 shows an organic light-emitting device 100. The drawing is not necessarily 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 further detail in U.S. Pat. No. 7,279,704, cols. 6-10, which is incorporated by reference.

[0046] Further examples are available for each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin layer of metal, such as Mg:Ag, with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their 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 can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0047] 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 can be fabricated by depositing the layers described, in order. Because the most common OLED configuration has the cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 is sometimes 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 an example of how some layers can be omitted from the structure of device 100.

[0048] The simple layer structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and it is understood that embodiments of the present invention can be used in conjunction 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. A functional OLED may be achieved by combining the various layers described in various 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. While many of the examples provided herein describe various layers as including a single material, it is understood that combinations of materials, such as mixtures of hosts and dopants, or more generally, mixtures, may be used. Layers may also 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 some embodiments, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials, for example, as described with respect to Figures 1 and 2.

[0049] Structures and materials not specifically described may also be used, such as OLEDs (PLEDs) composed of polymeric materials, such as those disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. As a further example, an OLED 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. OLED structures may deviate from the simple layered structures illustrated in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces to improve outcoupling, such as mesa structures as described in U.S. Pat. No. 6,091,195 to Forrest et al. and / or recessed structures as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0050] Unless otherwise specified, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include deposition by thermal evaporation, such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties; inkjet deposition; organic vapor phase deposition (OVPD), such as that described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety; and organic vapor jet printing (OVJP), such as that 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 performed in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition via masks, such as those described in U.S. Patent Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, deposition via cold welding, and patterning associated with some deposition methods, such as inkjet and OVJP. Other methods may also be used. The material to be deposited may be modified to be compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least three carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents with 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures, because asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

[0051] Devices fabricated according to embodiments of the present invention may further include 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, vapors, and / or gases. The barrier layer may be deposited over, under, or adjacent to the substrate, the electrode, or any other portion of the device, including the edges. The barrier layer may include 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 and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds, or both. Preferred barrier layers include mixtures of polymeric and non-polymeric materials, as described in U.S. Pat. No. 7,968,146 and PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entireties. To be considered a "mixture," the polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and / or simultaneously. The weight ratio of polymeric to non-polymeric materials can be in the range of 95:5 to 5:95. The polymeric and non-polymeric materials can be made from the same precursor materials. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0052] Devices fabricated in accordance with embodiments of the present invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, heads-up displays, fully transparent displays, flexible displays, laser printers, telephones, mobile phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, cars, large area walls, theater or stadium screens, or billboards. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices fabricated in accordance with the present invention. Many of the devices are intended for use within a temperature range comfortable to humans, such as 18°C ​​to 30°C, and more preferably room temperature (20-25°C), although they can also be used outside this temperature range, e.g., between -40°C and +80°C.

[0053] 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 use the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.

[0054] As used herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine, and iodine.

[0055] As used herein, the term "alkyl" refers to both straight-chain and branched-chain alkyl groups. Preferred alkyl groups are those containing 1 to 15 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. Furthermore, the alkyl groups may be optionally substituted.

[0056] As used herein, the term "cycloalkyl" refers to a cyclic alkyl group. Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, etc. Furthermore, the cycloalkyl groups may be substituted.

[0057] As used herein, the term "alkenyl" refers to both straight-chain and branched-chain alkenyl groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkenyl groups may be substituted.

[0058] As used herein, the term "alkynyl" refers to both straight-chain and branched-chain alkyne groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkynyl groups may be substituted.

[0059] As used herein, the term "aralkyl" or "arylalkyl" refers to an alkyl group having an aromatic group as a substituent. Additionally, the aralkyl group may be optionally substituted.

[0060] As used herein, the term "heterocyclic group" refers to a non-aromatic ring group. Preferred heterocyclic groups have at least one heteroatom containing 3 or 7 ring atoms, and include cyclic amines such as morpholino, piperidino, and pyrrolidino, and cyclic ethers such as tetrahydrofuran and tetrahydropyran. Furthermore, the heterocyclic group may be substituted.

[0061] As used herein, "aryl" or "aromatic group" refers to monocyclic and polycyclic ring systems. Polycyclic rings can have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), and at least one of the rings is aromatic, e.g., the other rings are cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Additionally, the aryl group may be substituted.

[0062] As used herein, "heteroaryl" refers to a monocyclic heteroaromatic group containing one to three heteroatoms, such as, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, and pyrimidine. The term heteroaryl also includes polycyclic heteroaromatic systems having two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), at least one of which is heteroaryl, and the other rings can be, for example, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Furthermore, the heteroaryl may be optionally substituted.

[0063] The alkyl, the cycloalkyl, the alkenyl, the alkynyl, the aralkyl, the heterocycle, the aryl, and the heteroaryl may be substituted with one or more substituents selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0064] As used herein, the term "substituted" indicates that a substituent other than hydrogen is attached to the associated carbon or nitrogen atom. Thus, for example, R 1 is monosubstituted, R 1 must be other than hydrogen. Similarly, R 1 is disubstituted, R 1 Two of the R must be non-hydrogen. 1 If represents unsubstituted, R 1 is hydrogen at all substitution positions.

[0065] The term "aza" in the fragments described herein, such as aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C—H groups in each fragment can be replaced with a nitrogen atom; for example, but not by way of limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Those skilled in the art can easily imagine other nitrogen analogs of the above-described aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0066] It is understood that when a molecular fragment is described as a substituent or as being attached to another moiety, the name may be described as either the fragment (e.g., naphthyl, dibenzofuryl) or the entire molecule (naphthalene, dibenzofuran). Different designations of the substituent or attached fragment are considered equivalent herein.

[0067] Provided herein are novel classes of compounds that include ligands with novel structures. These compounds can be used in phosphorescent organic light-emitting devices. In some embodiments, these compounds are used as emissive dopants in the emissive layer. The ligands provided herein can be used to tailor the properties of the compounds to provide more desirable properties. Incorporation of the ligands provided herein results in red phosphorescent materials with good external quantum efficiency, good color, and long lifetime.

[0068] In some embodiments, the ligand L is represented by formula (I): A The present invention provides a compound comprising: [ka] In the compound of formula (I), ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where the wavy line represents the bond to ring B; R 1 and R 3 each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of Y is nitrogen; 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; L A is coordinated to the metal M; L A is optionally linked to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and M is optionally coordinated to other ligands.

[0069] In some embodiments, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

[0070] In some embodiments, M is Ir.

[0071] In some embodiments, Y 1 is selected from the group consisting of NR', O, S, and CR'R''.

[0072] In some embodiments, Y 1 is O.

[0073] In some embodiments, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 One of them is nitrogen.

[0074] In some embodiments, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 Two of them are nitrogen.

[0075] In some embodiments, X 1 , X 2 , X 3 , and X 4 One of the is nitrogen; X 5 , X 6 , X 7 , and X 8 One of them is nitrogen.

[0076] In some embodiments, X 1 , X 2 , X 3 , and X 4 One of the is nitrogen; X5 , X 6 , X 7 , and X 8 is carbon.

[0077] In some embodiments, X 2 is nitrogen and X 1 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is carbon.

[0078] In some embodiments, A is phenyl.

[0079] In some embodiments, L A teeth, [ka] is selected from the group consisting of:

[0080] In some embodiments, the compound has formula (IA). [ka] In the compound of formula (IA), L is a ligand; A when n2 is 2 or more, L may be the same or different; ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II), [ka] where the wavy line represents the bond to ring B; R 1 and R 3 each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of Y is nitrogen; 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring (which may be further substituted); M is a metal; n1 is an integer from 1 to 6; n2 is an integer from 0 to 3; and n1 + n2 is an integer from 1 to 6.

[0081] In some embodiments, L is L B is.

[0082] In some embodiments, the compound has formula (III): [ka] (In the formula, L B is a bidentate ligand and n is 1, 2, or 3.

[0083] In some embodiments, the compound has formula (III-A): [ka] (In the formula, L B is a bidentate ligand and n is 1, 2, or 3.

[0084] In some embodiments, L A is shown below A1 ~L A960 is selected from the group consisting of: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0085] In some embodiments, L B is selected from the group consisting of: [ka] [ka]

[0086] In some embodiments, L B is selected from the group consisting of: [ka]

[0087] In some embodiments, the compound has formula (IV): [ka] and are selected from the group consisting of Compounds 1 to 960 listed in Table 1. Note that, like Table 1-1, each column in the following Tables 1-2 to 1-10 is written from left to right as "Compound Number," "L A ”, “Compound number”, “L A ”, “Compound number”, “L A ", "Compound No.", and "L A " means. [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10]

[0088] In some embodiments, the compound has formula (V): [ka] and selected from the group consisting of Compounds 961 to 5760 listed in Table 2. Note that, like Table 2-1, each column in the following Tables 2-2 to 2-54 is written from left to right as "Compound Number," "L A ","L B ”, “Compound number”, “L A ","L B ”, “Compound number”, “L A " and "L B " means. [Table 2-1] [Table 2-2] Table 2-3 Table 2-4 Table 2-5 Table 2-6 Table 2-7 Table 2-8 Table 2-9 Table 2-10 Table 2-11 Table 2-12 Table 2-13 Table 2-14 Table 2-15 Table 2-16 Table 2-17 Table 2-18 Table 2-19 Table 2-20 Table 2-21 Table 2-22 Table 2-23 Table 2-24 Table 2-25 Table 2-26 Table 2-27 Table 2-28 Table 2-29 Table 2-30 Table 2-31 Table 2-32 Table 2-33 Table 2-34 Table 2-35 Table 2-36 Table 2-37 Table 2-38 Table 2-39 Table 2-40 Table 2-41 Table 2-42 Table 2-43 Table 2-44 Table 2-45 Table 2-46 Table 2-47 Table 2-48 Table 2-49 Table 2-50 Table 2-51 Table 2-52 Table 2-53 [Table 2-54] [Table 2-55] [Table 2-56] [Table 2-57] [Table 2-58] [Table 2-59] [Table 2-60] [Table 2-61] [Table 2-62] [Table 2-63]

[0089] In some embodiments, the compound has formula (VI): [ka] and selected from the group consisting of Compounds 5761 to 7680 listed in Table 3. Note that, like Table 3-1, each column in the following Tables 3-2 to 3-26 is written from left to right as "Compound Number," "L A ","L B ”, “Compound number”, “L A ","L B ”, “Compound number”, “L A " and "L B " means. [Table 3-1] Table 3-2 Table 3-3 Table 3-4 Table 3-5 Table 3-6 Table 3-7 Table 3-8 Table 3-9 Table 3-10 Table 3-11 Table 3-12 Table 3-13 Table 3-14 Table 3-15 Table 3-16 Table 3-17 Table 3-18 [Table 3-19] [Table 3-20] [Table 3-21] [Table 3-22] [Table 3-23] [Table 3-24] [Table 3-25] [Table 3-26]

[0090] In some embodiments, the compound is selected from the group consisting of: [ka]

[0091] In some embodiments, a first organic light emitting device is provided, the first organic light emitting device comprising: an anode; a cathode; an organic layer disposed between the anode and the cathode, the organic layer comprising a ligand L represented by formula (I): A and an organic layer containing a compound comprising: [ka] Ligand L represented by formula (I) A wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where the wavy line represents the bond to ring B; R 1 and R 3 each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2 represents mono- or di-substituted or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of Y is nitrogen; 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring (which may be further substituted); L A is coordinated to the metal M; L A is optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and M is optionally coordinated to other ligands.

[0092] In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (IA). In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (III). In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (III-A). In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (IV). In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (V). In some embodiments, a first organic light emitting device comprises an organic layer comprising a compound of Formula (VI).

[0093] In some embodiments, the organic layer of the device is an emissive layer and contains a ligand L of formula (I): A The compound comprising is an emissive dopant. In some embodiments, the compound of Formula (IA) is an emissive dopant. In some embodiments, the compound of Formula (III) is an emissive dopant. In some embodiments, the compound of Formula (III-A) is an emissive dopant. In some embodiments, the compound of Formula (IV) is an emissive dopant. In some embodiments, the compound of Formula (V) is an emissive dopant. In some embodiments, the compound of Formula (VI) is an emissive dopant.

[0094] In some embodiments, the ligand L of formula (I) A The compound comprising is a phosphorescent dopant. In some embodiments, the compound of Formula (IA) is a phosphorescent dopant. In some embodiments, the compound of Formula (III) is a phosphorescent dopant. In some embodiments, the compound of Formula (III-A) is a phosphorescent dopant. In some embodiments, the compound of Formula (IV) is a phosphorescent dopant. In some embodiments, the compound of Formula (V) is a phosphorescent dopant. In some embodiments, the compound of Formula (VI) is a phosphorescent dopant.

[0095] In some embodiments, the organic layer of the device is an emissive layer and contains a ligand L of formula (I): A The compound comprising is a non-emissive dopant. In some embodiments, the compound of Formula (IA) is a non-emissive dopant. In some embodiments, the compound of Formula (III) is a non-emissive dopant. In some embodiments, the compound of Formula (III-A) is a non-emissive dopant. In some embodiments, the compound of Formula (IV) is a non-emissive dopant. In some embodiments, the compound of Formula (V) is a non-emissive dopant. In some embodiments, the compound of Formula (VI) is a non-emissive dopant.

[0096] In some embodiments, the device is a consumer product. In some embodiments, the device is an organic light emitting device. In some embodiments, the device includes a lighting panel.

[0097] In some embodiments, the organic layer further comprises a host.

[0098] In some embodiments, the host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan; Any substituent in the host may be C n H 2n+1 , O.C. n H 2n+1 , OAr1, N(C n H 2n+1 )2, N(Ar1)(Ar2), CH=CH-C n H 2n+1 , C≡CC n H 2n+1 , Ar1, Ar1-Ar2, and C n H 2n -Ar1 is a non-fused substituent independently selected from the group consisting of, or may be unsubstituted; In the foregoing substituents, n can range from 1 to 10; Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0099] In some embodiments, the host can be a compound containing at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene, hi some embodiments, the host is a metal complex.

[0100] The host can be a specific compound selected from the group consisting of: [ka]

[0101] In some embodiments, the compounds described herein are provided in compositions together with other materials present in the device, for example, the compounds of the present invention may be provided in compositions in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, or other layers.

[0102] In some embodiments, the ligand L is represented by formula (I): A A composition comprising a compound comprising: [ka] The ligand L of formula (I) A wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): [ka] where the wavy line represents the bond to ring B; R 1 and R 3 each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted; R 2represents mono- or di-substituted or unsubstituted; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 at least one of Y is nitrogen; 1 is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R'', SiR'R'', and GeR'R''; R 1 , R 2 , R 3 R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring (which may be further substituted); L A is coordinated to the metal M; L A is optionally linked to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and M is optionally coordinated to other ligands.

[0103] In some embodiments, the composition comprises a compound of Formula (IA). In some embodiments, the composition comprises a compound of Formula (III). In some embodiments, the composition comprises a compound of Formula (III-A). In some embodiments, the composition comprises a compound of Formula (IV). In some embodiments, the composition comprises a compound of Formula (V). In some embodiments, the composition comprises a compound of Formula (VI). Combination with other materials

[0104] The materials described herein as useful for a particular layer in an organic light-emitting device can be used in combination with a wide variety of other materials present in the device. For example, the emissive dopants disclosed herein can 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 referenced below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that may be useful in combination. HIL / HTL:

[0105] The hole injection / transport material used in the embodiments of the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injection / transport material. Examples of such materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorocarbons; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembly monomers derived from compounds such as phosphonic acid and silane derivatives; MoO x p-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds.

[0106] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structures: [ka]

[0107] Ar 1 From Ar 9are a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; 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, indole, and aromatic heterocyclic compounds such as oxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and 2 to 10 cyclic structural units of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, which are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic cyclic group. wherein each Ar is further substituted with substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0108] In some embodiments, Ar 1 From Ar 9teeth, [ka] are independently selected from the group consisting of:

[0109] k is an integer from 1 to 20; X 101 From X 108 is C (including CH) or N; Z 101 is NAr 1 , O, or S; Ar 1 has the same radical as defined above.

[0110] Examples of metal complexes used in the HIL or HTL include, but are not limited to, those of the following general formula: [ka]

[0111] Met is a metal; (Y 101 -Y 102 ) is a bidentate ligand, and Y 101 and Y 102 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k'' is the maximum number of ligands that can be attached to the metal.

[0112] In some embodiments, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative.

[0113] In some embodiments, (Y 101 -Y 102 ) is a carbene ligand.

[0114] In some embodiments, Met is selected from Ir, Pt, Os, and Zn.

[0115] In a further embodiment, the metal complex is +For the / Fc couple, it has a minimum oxidation potential of less than about 0.6 V in solution. host:

[0116] The light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may also contain a host material that uses the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is higher than that of the dopant. In the table below, preferred host materials for devices emitting each color are classified, but any host material may be used with any dopant as long as the triplet criterion is met.

[0117] Examples of metal complexes used as host materials preferably have the following general formula: [ka]

[0118] Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, and Y 103 and Y 104 are independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k'' is the maximum number of ligands that can be attached to the metal.

[0119] In some embodiments, the metal complex is: [ka]

[0120] where (ON) is a bidentate ligand with the metal coordinated to atoms O and N.

[0121] In some embodiments, Met is selected from Ir and Pt.

[0122] In a further embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0123] Examples of organic compounds used as the host material include the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; 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, and indole. and aromatic heterocyclic compounds such as benzofuropyridine, 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 aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which may be the same or different groups and which are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic cyclic group. Each group is further substituted with substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0124] In some embodiments, the host compound contains at least one of the following groups in the molecule: [ka]

[0125] In the formula, R 101 From R 107 is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above.

[0126] k is an integer from 1 to 20; k''' is an integer from 0 to 20.

[0127] X 101 From X 108 is selected from C (including CH) or N.

[0128] Z 101 and Z 102 is NR 101 , O, or S. HBL:

[0129] A hole-blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the light-emitting layer. The presence of such a blocking layer in a device can result in significantly higher efficiency compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine light emission to desired regions of an OLED.

[0130] In some embodiments, the compound used in the HBL comprises the same molecule as that used as the host described above.

[0131] In some embodiments, the compound used in the HBL contains at least one of the following groups in the molecule: [ka]

[0132] k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3. ETL:

[0133] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound typically used to transport electrons may be used.

[0134] In some embodiments, the compound used in the ETL contains at least one of the following groups in the molecule: [ka]

[0135] R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above.

[0136] Ar 1 From Ar 3has the same definition as that of Ar mentioned above.

[0137] k is an integer between 1 and 20.

[0138] X 101 From X 108 is selected from C (including CH) or N.

[0139] In some embodiments, the metal complex used in the ETL comprises, but is not limited to, the following general formula: [ka]

[0140] (ON) or (NN) is a bidentate ligand with the metal coordinated to atoms O, N or N, N; L 101 is another ligand; and k' is an integer value between 1 and the maximum number of ligands that can be attached to the metal.

[0141] In any of the above-mentioned compounds used in each layer of an OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically recited substituent, such as, but not limited to, methyl, phenyl, pyridyl, etc., includes undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, substituent classes, such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc., also include undeuterated, partially deuterated, and fully deuterated versions thereof.

[0142] In addition to and / or in combination with the materials disclosed herein, many hole injection materials, hole transport materials, host materials, dopant materials, exciton / hole blocking layer materials, electron transport and electron injection materials can be used in OLEDs. Non-limiting examples of materials that can be used in combination with the materials disclosed herein in OLEDs are listed in Table 4 below. Table 4 lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials. [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] [Table 4-5] [Table 4-6] [Table 4-7] [Table 4-8] [Table 4-9] [Table 4-10] [Table 4-11] [Table 4-12] [Table 4-13] [Table 4-14] [Table 4-15] [Table 4-16] [Table 4-17] [Table 4-18] [Table 4-19] [Table 4-20] [Table 4-21] [Table 4-22] [Example]

[0143] All reactions were carried out under nitrogen unless otherwise specified. All solvents for reactions were anhydrous and used as received from commercial sources. Example 1 Synthesis of compound 2881 Synthesis of 4-phenylbenzofuro[3,2-d]pyrimidine

[0144] [ka]

[0145] 4-Chlorobenzofuro[3,2-d]pyrimidine (3.50 g, 17.1 mmol), phenylboronic acid (2.61 g, 21.4 mmol), and K2CO3 (4.73 g, 34.2 mmol) were dissolved in toluene (95 mL) and water (19 mL). The reaction mixture was degassed by bubbling nitrogen through for 15 minutes. Pd(PPh3)4 (0.99 g, 0.86 mol) was then added, and the mixture was heated to reflux overnight. Upon completion of the reaction, it was cooled to room temperature, extracted with toluene, and washed with water. The crude product was purified by column chromatography using heptane / ethyl acetate (starting with 90 / 10 and slowly increasing to 75 / 25). The mobile phase was changed to heptane / ethyl acetate / dichloromethane (65 / 25 / 10). The collected fractions were triturated with methanol to give 4-phenylbenzofuro[3,2-d]pyrimidine (3.2 g, 76% yield). Synthesis of compound 2881

[0146] [ka]

[0147] The iridium intermediate (2.01 g, 2.71 mmol) and 4-phenylbenzofuro[3,2-d]pyrimidine (2.00 g, 8.12 mmol) were diluted with ethanol (27 mL) and heated to reflux for 36 h. When the HPLC timer expired, the reaction mixture was cooled to room temperature. The solid was filtered through a pad of Celite and washed with methanol. The collection flask was then replaced, and the solid on the Celite was washed with dichloromethane. The crude product was purified by column chromatography using heptane / ethyl acetate (80 / 20) and then dichloromethane / ethyl acetate (60 / 40). The collected fractions were recrystallized three times from dichloromethane / methanol to give compound 2881 (1.2 g, 57% yield). Example 2 Synthesis of compound 6857 Synthesis of 4-(3,5-dimethylphenyl)benzofuro[3,2-d]pyrimidine

[0148] [ka]

[0149] 4-Chlorobenzofuro[3,2-d]pyrimidine (4.75 g, 23.2 mmol), (3,5-dimethylphenyl)boronic acid (4.35 g, 29.0 mmol), and K2CO3 (6.42 g, 46.4 mmol) were dissolved in toluene (130 mL) and water (26 mL). Pd(PPh3)4 (1.34 g, 1.16 mmol) was added, and the mixture was degassed by bubbling with nitrogen. The mixture was heated to 80 °C overnight. When the reaction was complete as determined by gas chromatography-mass spectrometry (GCMS), the mixture was cooled to room temperature, extracted with toluene, and washed with water. The crude material was coated onto Celite and purified by column chromatography using heptane / ethyl acetate (80 / 20). The product was recrystallized from heptane to give 4-(3,5-dimethylphenyl)benzofuro[3,2-d]pyrimidine (4.4 g, 69% yield) as white crystals. Synthesis of Ir(III) dimer

[0150] [ka]

[0151] 4-(3,5-Dimethylphenyl)benzofuro[3,2-d]pyrimidine (2.00 g, 7.29 mmol) was solubilized in ethoxyethanol (23 mL) and water (8 mL) and degassed by bubbling with nitrogen for 15 minutes. Iridium chloride (0.90 g, 2.43 mmol) was added to the slurry (the ligand is sparingly soluble), and the reaction was heated to 105 °C under nitrogen for 24 hours. After cooling to room temperature, the solid was filtered, washed with methanol, and dried to give the Ir(III) dimer (2.4 g, 128% yield) as an orange powder. The crude dimer contained free ligand, resulting in a higher-than-theoretical yield. The Ir(III) dimer was used without further purification. Synthesis of compound 6857

[0152] [ka]

[0153] Ir(III) dimer (2.4 g, 1.24 mmol) and 3,7-diethylnonane-4,6-dione (2.63 g, 12.4 mmol) were added to a round-bottom flask. The mixture was diluted with ethoxyethanol (40 mL), degassed by bubbling with nitrogen, and K2CO3 (1.71 g, 12.4 mmol) was added. The mixture was stirred at room temperature for 1 hour and then heated at 90 °C overnight. The reaction mixture was diluted with dichloromethane and filtered through a pad of Celite. The crude product was then purified by column chromatography using heptane / dichloromethane (90 / 10). The red solid was recrystallized from a mixture of dichloromethane and heptane to give compound 6857 (0.40 g, 17% yield). Device Example

[0154] All example devices were placed in high vacuum (<10 -7 The devices were fabricated by thermal evaporation at 1000 Å (2000 ft) at room temperature. The anode electrode was 1,200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of LiF and 1,000 Å of Al. All devices were encapsulated immediately after fabrication in a nitrogen glove box (H2O and O2 <1 ppm) with a glass lid sealed with epoxy resin, and a moisture getter was placed inside the package.

[0155] The organic stack for the device examples consisted of, in order, an ITO surface, 100 Å of LG101 (purchased from LG Chem) as the hole injection layer (HIL), 400 Å of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD) as the hole transport layer (HTL), 400 Å of a compound of the present invention doped with BAlq as a host as the light emitting layer (EML), 100 Å of BAlq as the blocking layer (BL), and 450 Å of Alq (tris-8-hydroxyquinoline aluminum) as the ETL.

[0156] The device results and data obtained from these devices are summarized in Tables 5 and 6. As used herein, NPD, Alq3, BAlq have the following structures: [ka] [Table 5] [Table 6]

[0157] Table 6 summarizes the device performance. The driving voltage (V), luminous efficiency (LE), external quantum efficiency (EQE), and power efficiency (PE) were measured at 1,000 nits. Both examples exhibited red emission. Device Example 1 exhibited an sRGB red color with a CIE of (0.65, 0.35) and a good EQE (15%). Device Example 2 exhibited a very deep red color with a CIE of (0.68, 0.32) and a good EQE (14%). These devices can be used as red emitters in display and lighting applications. The compounds disclosed in WO2010118029, which have only one nitrogen atom at the top of the ligand, can only emit colors in the green-yellow range and cannot achieve the desired red color in the present invention. Therefore, these compounds were not useful as red emitters.

[0158] 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 can be substituted with other materials and structures without departing from the spirit of the invention. Thus, the present invention as claimed may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It is understood that various theories as to why the invention works are not intended to be limiting. [Prior art documents] [Patent documents]

[0159] [Patent Document 1] U.S. Patent No. 5,844,363 [Patent Document 2] U.S. Patent No. 6,303,238 [Patent Document 3] U.S. Patent No. 5,707,745 [Patent Document 4] U.S. Patent No. 7,279,704 [Explanation of symbols]

[0160] 100 Organic Light-Emitting Devices 110 Substrate 115 Anode 120 Hole injection layer 125 Hole transport layer 130 Electron Blocking Layer 135 Light-emitting layer 140 Hole Blocking Layer 145 Electron transport layer 150 Electron injection layer 155 Protective layer 160 cathode 162 First conductive layer 164 Second Conductive Layer 170 Barrier Layer 200 Inverted OLED, device 210 Substrate 215 cathode 220 Light-emitting layer 225 Hole transport layer 230 Anode

Claims

1. A ligand L represented by the following formula (I): Ａ 1. A material for use in an OLED, comprising: 【Chemistry 1】 (In formula (I), ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): 【Chemistry 2】 where: The wavy line represents the bond to ring B; R １ and R ３ each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted; R ２ represents mono- or di-substituted, or unsubstituted; X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , and X ８ are each independently carbon or nitrogen; X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , and X ８ at least one of is nitrogen; Y １ is S; R １ , R ２ , R ３ , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; The ligand L Ａ is coordinated to the metal M, The ligand L Ａ is optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; The M is optionally coordinated to other ligands.

2. 10. The material for use in an OLED according to claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. 2. The material for use in an OLED according to claim 1, wherein ring A is phenyl.

4. L Ａ 10. The material for use in an OLED according to claim 1, wherein is selected from the group consisting of: 【Transformation 3】

5. 2. The material for use in an OLED according to claim 1, wherein the compound is represented by the following formula (III-A): 【Chemistry 4】 (In the formula, L Ｂ is a bidentate ligand and n is 1, 2, or 3; L Ａ is the L shown below Ａ２ 、L Ａ６ 、L Ａ１０ 、L Ａ１４ 、L Ａ１８ 、L Ａ２２ 、L Ａ２６ 、L Ａ３０ 、L Ａ３４ 、L Ａ３８ 、L Ａ４２ 、L Ａ４６ 、L Ａ５０ 、L Ａ５４ 、L Ａ５８ 、L Ａ６２ 、L Ａ６６ 、L Ａ７０ 、L Ａ７４ 、L Ａ７８ 、L Ａ８２ 、L Ａ８６ 、L Ａ９０ 、L Ａ９４ 、L Ａ９８ 、L Ａ１０２ 、L Ａ１０６ 、L Ａ１１０ 、L Ａ１１４ 、L Ａ１１８ 、L Ａ１２２ 、L Ａ１２６ 、L Ａ１３０ 、L Ａ１３４ 、L Ａ１３８ 、L Ａ１４２ 、L Ａ１４６ 、L Ａ１５０ 、L Ａ１５４ 、L Ａ１５８ 、L Ａ１６２ 、L Ａ１６６ 、L Ａ１７０ 、L Ａ１７４ 、L Ａ１７８ 、L Ａ１８２ 、L Ａ１８６ 、L Ａ１９０ 、L Ａ１９４ 、L Ａ１９８ 、L Ａ２０２ 、L Ａ２０６ 、L Ａ２１０ 、L Ａ２１４ 、L Ａ２１８ 、L Ａ２２２ [[ID=​​​​​​​​​​​​​​​​​​ Ａ２６２ L Ａ２６６ L Ａ２７０ L Ａ２７４ L Ａ２７８ L Ａ２８２ L Ａ２８６ L Ａ２９０ L Ａ２９４ L Ａ２９８ L Ａ３０２ L Ａ３０６ L Ａ３１０ L Ａ３１４ L Ａ３１８ L Ａ３２２ L Ａ３２６ L Ａ３３０ L Ａ３３４ L Ａ３３８ L Ａ３４２ L Ａ３４６ L Ａ３５０ L Ａ３５４ L Ａ３５８ L Ａ３６２ L Ａ３６６ L Ａ３７０ L Ａ３７４ L Ａ３７８ L Ａ３８２ L Ａ３８６ L Ａ３９０ L Ａ３９４ L Ａ３９８ L Ａ４０２ L Ａ４０６ L Ａ４１０ L Ａ４１４ L Ａ４１８ L Ａ４２２ L Ａ４２６ L Ａ４３０ L Ａ４３４ L Ａ４３８ L Ａ４４２ L Ａ４４６ L Ａ４５０ L Ａ４５４ L Ａ４５８ L Ａ４６２ L Ａ４６６ L Ａ４７０ L Ａ４７４ L Ａ４７８ L Ａ４８２ L Ａ４８６ L Ａ４９０ L Ａ４９４ L Ａ４９８ L Ａ５０２ L Ａ５０６ L Ａ５１０ L Ａ５１４ L Ａ５１８ L Ａ５２２ L Ａ５２６ L Ａ５３０ L Ａ５３４ L Ａ５３８ L Ａ５４２ L Ａ５４６ L Ａ５５０ L Ａ５５４ L Ａ５５８ L Ａ５６２ L Ａ５６６ L Ａ５７０ L Ａ５７４ L Ａ５７８ L Ａ５８２ L Ａ５８６ L Ａ５９０ L Ａ５９４ L Ａ５９８ L Ａ６０２ L Ａ６０６ L Ａ６０１０ L Ａ６１４ L Ａ６１８ L Ａ６２２ L Ａ６２６ L Ａ６３０ L Ａ６３４ L Ａ６３８ L Ａ６４２ L Ａ６４６ L Ａ６５０ L Ａ６５４ L Ａ６５８ L Ａ６６２ L Ａ６６６ L Ａ６７０ L Ａ６７４ L Ａ６７８ L Ａ６８２ L Ａ６８６ L Ａ６９０ L Ａ６９４ L Ａ６９８ L Ａ７０２ L Ａ７０６ L Ａ７１０ L Ａ７１４ L Ａ７１８ L Ａ７２２ L Ａ７２６ L Ａ７３０ L Ａ７３４ L Ａ７３８ L Ａ７４２ L Ａ７４６ L Ａ７５０ L Ａ７５４ L Ａ７５８ L Ａ７６２ L Ａ７６６ L Ａ７７０ L Ａ７７４ L Ａ７７８ L Ａ７８２ L Ａ７８６ L Ａ７９０ L Ａ７９４ , L Ａ７９８ , L Ａ８０２ , L Ａ８０６ , L Ａ８１０ , L Ａ８１４ , L Ａ８１８ , L Ａ８２２ , L Ａ８２６ , L Ａ８３０ , L Ａ８３４ , L Ａ８３８ , L0000240, L Ａ８４６ , L Ａ８５０ , L Ａ８５４ , L Ａ８５８ , L Ａ８６２ , L Ａ８６６ , L Ａ８７０ , L Ａ８７４ , L Ａ８７８ , L Ａ８８２ , L Ａ８８６ , L Ａ８９０ , L Ａ８９４ , L Ａ８９８ , L Ａ９０２ , L Ａ９０６ , L Ａ９１０ , L Ａ９１４ , L Ａ９１８ , L Ａ９２２ , L Ａ９２６ , L Ａ９３０ , L Ａ９３４ , L Ａ９３８ , L Ａ９４２ , L Ａ９４６ , L Ａ９５０ , L Ａ９５４ and L Ａ９５８ is selected from the group consisting of.) 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】

6. A ligand L represented by the following formula (I): Ａ An organic layer comprising a compound comprising: 【Chemistry 26】 (In formula (I), ring A is a 5- or 6-membered carbocyclic or heterocyclic ring; R is fused to ring B and is represented by formula (II): 【Chemistry 27】 where: The wavy line represents the bond to ring B; R １ and R ３ each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted; R ２ represents mono- or di-substituted, or unsubstituted; X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , and X ８ are each independently carbon or nitrogen; X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , and X ８ at least one of is nitrogen; Y １ is S; R １ , R ２ , R ３ , R', and R'' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or any two adjacent substituents are optionally joined to form a ring, which may be further substituted; The ligand L Ａ is coordinated to the metal M, The ligand L Ａ is optionally combined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; The M is optionally coordinated to other ligands.

7. 7. The organic layer of claim 6, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

8. The organic layer according to claim 6 , wherein ring A is phenyl.

9. L Ａ 7. The organic layer of claim 6, wherein is selected from the group consisting of: 【Chemistry 28】

10. 7. The organic layer according to claim 6, wherein the compound is represented by the following formula (III-A): 【Chemistry 29】 (In the formula, L Ｂ is a bidentate ligand and n is 1, 2, or 3; L Ａ is the L shown below Ａ２ L Ａ６ L Ａ１０ L Ａ１４ L Ａ１８ L Ａ２２ L Ａ２６ L Ａ３０ L Ａ３４ L Ａ３８ L Ａ４２ L Ａ４６ L Ａ５０ L Ａ５４ L Ａ５８ L Ａ６２ L Ａ６６ L Ａ７０ L Ａ７４ L Ａ７８ L Ａ８２ L Ａ８６ L Ａ９０ L Ａ９４ L Ａ９８ L Ａ１０２ L Ａ１０６ L Ａ１１０ L Ａ１１４ L Ａ１１８ L Ａ１２２ L Ａ１２６ L Ａ１３０ L Ａ１３４ L Ａ１３８ L Ａ１４２ L Ａ１４６ L Ａ１５０ L Ａ１５４ L Ａ１５８ L Ａ１６２ L Ａ１６６ L Ａ１７０ L Ａ１７４ L Ａ１７８ L Ａ１８２ L Ａ１８６ L Ａ１９０ L Ａ１９４ L Ａ１９８ L Ａ２０２ L Ａ２０６ L Ａ２１０ L Ａ２１４ L Ａ２１８ L Ａ２２２ L Ａ２２６ L Ａ２３０ L Ａ２３４ L Ａ２３８ L Ａ２４２ L Ａ２４６ L Ａ２５０ L Ａ２５４ L Ａ２５８ L Ａ２６２ L Ａ２６６ L Ａ２７０ L Ａ２７４ L Ａ２７８ L Ａ２８２ L Ａ２８６ L Ａ２９０ L Ａ２９４ L Ａ２９８ L Ａ３０２ L Ａ３０６ L Ａ３１０ L Ａ３１４ L Ａ３１８ L Ａ３２２ L Ａ３２６ L Ａ３３０ L Ａ３３４ L Ａ３３８ L Ａ３４２ L Ａ３４６ L Ａ３５０ L Ａ３５４ L Ａ３５８ L Ａ３６２ L Ａ３６６ L Ａ３７０ L Ａ３７４ L Ａ３７８ L Ａ３８２ L Ａ３８６ L Ａ３９０ L Ａ３９４ L Ａ３９８ L Ａ４０２ L Ａ４０６ L Ａ４１０ L Ａ４１４ L Ａ４１８ L Ａ４２２ L Ａ４２６ L Ａ４３０ L Ａ４３４ L Ａ４３８ L Ａ４４２ L Ａ４４６ L Ａ４５０ L Ａ４５４ L Ａ４５８ L Ａ４６２ L Ａ４６６ L Ａ４７０ L Ａ４７４ L Ａ４７８ L Ａ４８２ L Ａ４８６ L Ａ４９０ L Ａ４９４ L Ａ４９８ L Ａ５０２ L Ａ５０６ L Ａ５１０ L Ａ５１４ L Ａ５１８ L Ａ５２２ L Ａ５２６ L Ａ５３０ L Ａ５３４ L Ａ５３８ L Ａ５４２ L Ａ５４６ L Ａ５５０ L Ａ５５４ L Ａ５５８ L Ａ５６２ L Ａ５６６ L Ａ５７０ L Ａ５７４ L Ａ５７８ L Ａ５８２ L Ａ５８６ L Ａ５９０ L Ａ５９４ L Ａ５９８ L Ａ６０２ L Ａ６０６ L Ａ６０１０ L Ａ６１４ L Ａ６１８ L Ａ６２２ L Ａ６２６ L Ａ６３０ L Ａ６３４ L Ａ６３８ L Ａ６４２ L Ａ６４６ L Ａ６５０ L Ａ６５４ L Ａ６５８ L Ａ６６２ L Ａ６６６ L Ａ６７０ L Ａ６７４ L Ａ６７８ L Ａ６８２ L Ａ６８６ L Ａ６９０ L Ａ６９４ L Ａ６９８ L Ａ７０２ L Ａ７０６ L Ａ７１０ L Ａ７１４ L Ａ７１８ L Ａ７２２ L Ａ７２６ L Ａ７３０ L Ａ７３４ L Ａ７３８ L Ａ７４２ L Ａ７４６ L Ａ７５０ L Ａ７５４ L Ａ７５８ L Ａ７６２ L Ａ７６６ L Ａ７７０ L Ａ７７４ L Ａ７７８ L Ａ７８２ L Ａ７８６ L Ａ７９０ L Ａ７９４ , L Ａ７９８ , L Ａ８０２ , L Ａ８０６ , L Ａ８１０ , L Ａ８１４ , L Ａ８１８ , L Ａ８２２ , L Ａ８２６ , L Ａ８３０ , L Ａ８３４ , L Ａ８３８ , L Ａ８４２ , L Ａ８４６ , L Ａ８５０ , L Ａ８５４ , L Ａ８５８ , L Ａ８６２ , L Ａ８６６ , L Ａ８７０ , L Ａ８７４ , L Ａ８７８ , L Ａ８８２ , L Ａ８８６ , L Ａ８９０ , L Ａ８９４ , L Ａ８９８ , L Ａ９０２ , L Ａ９０６ , L Ａ９１０ , L Ａ９１４ , L Ａ９１８ , L Ａ９２２ , L Ａ９２６ , L Ａ９３０ , L Ａ９３４ , L Ａ９３８ , L Ａ９４２ , L Ａ９４６ , L Ａ９５０ , L Ａ９５４ and L Ａ９５８ is selected from the group consisting of.) 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50]

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