Organic Electroluminescent Materials and Devices

Abstract

To provide organic luminescent compounds and composition and their various uses including as emitters in devices such as organic light emitting diodes and related consumer products.SOLUTION: Provided are multicyclic organic luminescent compounds having a ligand represented by the formula in the figure. Also provided are OLEDs and related consumer products that contain an organic layer having these organic luminescent compounds.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] Cross - reference to Related Applications This application claims priority to U.S. Provisional Application No. 62 / 880,389, filed on July 30, 2019, under 35 U.S.C. § 119(e), and the entire disclosure thereof is incorporated herein by reference in its entirety.

[0002] The present disclosure relates to compounds and compositions, and their various uses including emitters in devices such as organic light - emitting diodes and related consumer products.

Background Art

[0003] Optoelectronic devices that utilize organic materials are becoming increasingly desirable for various reasons. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost - advantages over inorganic devices. In addition, due to the inherent properties of organic materials such as flexibility, the materials can be well - suited for specific applications such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light - emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

[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, lighting, and backlighting.

[0005] One use of the phosphorescent luminescent molecule is a full-color display. 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. Alternatively, the OLED can be designed to emit white light. Conventional liquid crystal display emission from a white backlight is filtered using absorption filters to produce red, green, and blue emission. Similar techniques can also be used with OLEDs. The white OLED can be either a single emitting layer (EML) device or a stacked structure. Colors can be measured using CIE coordinates well known in the art.

Summary of the Invention

[0006] In one aspect, the present disclosure provides a compound comprising a ligand L of formula I shown below A

Chemical Formula

[0007] In another aspect, the present disclosure provides a composition comprising the ligand L of formula I described herein A The composition can also include the ligand L A together with other ligands preferably selected from the ligands described herein, although these other ligands can also be selected from ligands known in the art.

[0008] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising the ligand L of formula I described herein A The OLED having the organic layer can also include the ligand L A together with other ligands preferably selected from the ligands described herein, although these other ligands can also be selected from ligands known in the art.

[0009] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising the ligand L of formula I described herein A The consumer product comprising the OLED having the organic layer can also include the ligand L A together with other ligands preferably selected from the ligands described herein, although these other ligands can also be selected from ligands known in the art. BRIEF DESCRIPTION OF THE DRAWINGS

[0010]

Figure 1

[0011]

Figure 2

[0012]

Figure 3

BEST MODE FOR CARRYING OUT THE INVENTION

[0013] A. Terms Unless otherwise specified, the following terms used in this specification are defined as follows.

[0014] As used herein, the term "organic" includes polymeric materials 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 molecule" can actually be quite large. Small molecules can include repeating units in some situations. For example, using a long-chain alkyl group as a substituent does not exclude a molecule from the "small molecule" class. Small molecules may be incorporated into a polymer, for example, as a pendant group on a polymer backbone or as part of the backbone. Small molecules can also serve as the core part of a dendrimer consisting of a series of chemical shells constructed on a core part. The core part of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. The dendrimer may be a "small molecule", and all dendrimers currently used in the field of OLEDs are considered to be small molecules.

[0015] As used herein, "top" means the farthest part from the substrate, while "bottom" means the closest part to the substrate. When the first layer is described as being "disposed on" the second layer, the first layer is disposed farther from the substrate. There may be other layers between the first layer and the second layer unless it is specified that the first layer is "in contact with" the second layer. For example, even if there are various organic layers in between, the cathode may be described as being "disposed on" the anode.

[0016] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in either solution or suspension form and / or capable of being deposited from such a medium.

[0017] A ligand may be termed "photoactive" if it is considered to directly contribute to the photoactive properties of a luminescent material. A ligand may be termed "auxiliary" if it is considered not to contribute to the photoactive properties of the luminescent material, although an auxiliary ligand may be able to modify the properties of a photoactive ligand.

[0018] As used herein, as generally understood by those skilled in the art, the first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater" or "higher" than the second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). In 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 to be closer to the top of such a diagram than a "lower" HOMO or LUMO energy level.

[0019] As used herein, and as will be generally understood by one of ordinary skill in the art, if the first work function has a higher absolute value, the first work function is "greater than" or "higher than" the second work function. Since work functions are generally measured as negative numbers relative to the vacuum level, this means that the "higher" work function is more negative. In a conventional energy level diagram with the vacuum level at the top, the "higher" work function is illustrated as being further away in the downward direction from the vacuum level. Thus, the definitions of the HOMO and LUMO energy levels follow a convention different from that of the work function.

[0020] The terms "halo", "halogen", and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0021] The term "acyl" refers to a substituted carbonyl group (C(O)-R s ).

[0022] The term "ester" refers to a substituted oxycarbonyl (-O-C(O)-R s or -C(O)-O-R s ).

[0023] The term "ether" refers to an -OR s group.

[0024] The terms "sulfanyl" or "thioether" are used interchangeably and refer to an -SR s group.

[0025] The term "sulfinyl" refers to an -S(O)-R s group.

[0026] The term "sulfonyl" refers to an -SO 2 -R s group.

[0027] The term "phosphino" refers to -P(R s )3 refers to a group, and each R s may be the same or different.

[0028] The term "silyl" refers to a -Si(R s ) 3 group, and each R s may be the same or different.

[0029] The term "boryl" refers to a -B(R s ) 2 group, or its Lewis adduct -B(R s ) 3 group, and R s may be the same or different.

[0030] In each of the above, R s is 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 combinations thereof. Preferred R s is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0031] The term "alkyl" refers to and includes both straight-chain and branched-chain alkyl groups. Preferred alkyl groups include those containing from 1 to 15 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, and 2,2-dimethylpropyl. Further, the alkyl group may be optionally substituted.

[0032] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Further, the cycloalkyl group may be optionally substituted.

[0033] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl group or a cycloalkyl group having at least one carbon atom substituted by a heteroatom, respectively. Optionally, at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Further, the heteroalkyl group or the heterocycloalkyl group may be optionally substituted.

[0034] The term "alkenyl" refers to and includes both straight-chain and branched-chain alkene groups. An alkenyl group is essentially an alkyl group containing at least one carbon-carbon double bond in the alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group containing at least one carbon-carbon double bond in the cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group having at least one carbon atom substituted by a heteroatom. Optionally, 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 2 to 15 carbon atoms. Further, the alkenyl, cycloalkenyl, or heteroalkenyl group may be optionally substituted.

[0035] The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne groups. An alkynyl group is essentially an alkyl group containing at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Further, the alkynyl group may be optionally substituted.

[0036] The term "aralkyl" or "arylalkyl" is used interchangeably and refers to an alkyl group substituted with an aryl group. Further, the aralkyl group may be optionally substituted.

[0037] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. A heteroaromatic cyclic group may be used interchangeably with heteroaryl. Preferred hetero non-aromatic cyclic groups include those containing 3 to 7 ring atoms, containing at least one heteroatom, and including cyclic amines such as morpholino, piperidino, pyrrolidino, and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, and tetrahydrothiophene. Further, the heterocyclic group may be optionally substituted.

[0038] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycycle can have two or more rings in which two adjacent rings (the rings are "fused") share two carbons, and at least one of the rings is an aromatic hydrocarbyl group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl. Preferred aryl groups are those containing 6 to 30 carbon atoms, preferably those containing 6 to 20 carbon atoms, and more preferably those containing 6 to 12 carbon atoms. Particularly preferred are aryl groups having 6 carbons, aryl groups having 10 carbons, or aryl groups having 12 carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, etc., and phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene are preferred. Further, the aryl group may be optionally substituted.

[0039] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems containing at least one heteroatom. Examples of heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many instances, O, S, or N are preferred heteroatoms. The hetero monocyclic aromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring can have 1 to 6 heteroatoms. The hetero polycyclic ring system can have two or more rings in which two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is heteroaryl. For example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. The hetero polycyclic aromatic ring system can have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, preferably those containing 3 to 20 carbon atoms, and more preferably those containing 3 to 12 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. Among them, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and their aza analogs are preferred. Further, the heteroaryl group may be optionally substituted.

[0040] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole groups, and their respective aza analogs are of particular interest.

[0041] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl are independently unsubstituted or independently substituted with one or more common substituents.

[0042] In many instances, said 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, boryl, and combinations thereof.

[0043] In some instances, 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, boryl, and combinations thereof.

[0044] In some instances, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

[0045] In still other instances, most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0046] The terms “substituted” and “substitution” refer to substituents other than H bonded to the relevant position (e.g., carbon or nitrogen). For example, when R 1 represents monosubstitution, one R 1 must be other than H (i.e., substitution). Similarly, when R 1 represents disubstitution, two of R 1 must be other than H. Similarly, when R 1 represents zero or unsubstituted, R 1It can be hydrogen at the available valences of the ring atoms, such as in the case of carbon atoms in benzene and nitrogen atoms in pyrrole, or it can represent nothing in the case of ring atoms with fully satisfied valences (e.g., nitrogen in pyridine). The maximum number of possible substitutions in the ring structure depends on the total number of available valences at the ring atoms.

[0047] As used herein, "these combinations" indicates that one or more members of the applied list are combined to form known or chemically stable arrangements that can be envisioned by those skilled in the art from the applied list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. In one example, the term substitution includes combinations of 2 to 4 of the listed groups. In another example, the term substitution includes combinations of 2 to 3 groups. In yet another example, the term substitution includes combinations of 2 groups. Preferred combinations of substituents are those containing up to 50 atoms other than hydrogen or deuterium, or those containing up to 40 atoms other than hydrogen or deuterium, or those containing up to 30 atoms other than hydrogen or deuterium. In many examples, preferred combinations of substituents contain up to 20 atoms other than hydrogen or deuterium.

[0048] The name "aza" in the fragments described herein, such as in aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in each aromatic ring can be replaced by a nitrogen atom. For example, without limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Those skilled in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and it is intended that all such analogs are encompassed by the terms described herein.

[0049] 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. Patent No. 8,557,400, International Publication No. WO2006 / 095951, and U.S. Patent Application Publication No. 2011 / 0037057, which are incorporated herein by reference in their entireties, describe the preparation of organometallic complexes substituted with deuterium. Further references are made by Tetrahedron 2015, 71, 1425 - 30 (Ming Yan et al.) and Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744 - 65 (Atzrodt et al.), which are incorporated herein by reference in their entireties, and describe efficient routes for deuterating methylene hydrogens in benzylamine and substituting aromatic ring hydrogens with deuterium, respectively.

[0050] When a molecular fragment is described as a substituent or as being attached to another moiety, it should be understood that its name may be described as a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). It is understood that in this specification, these are considered equivalent even if the ways of representing substituents or linking fragments are different.

[0051] In one example, a pair of adjacent substituents can optionally bond or condense to form a ring. Preferred rings are 5 - membered, 6 - membered, or 7 - membered carbocyclic or heterocyclic rings, including both examples where the ring portion formed by the pair of substituents is saturated and examples where the ring portion formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that as long as a stable fused ring system can be formed, two relevant substituents can be adjacent to each other on the same ring or on two adjacent rings having the two closest available substitutable positions, such as the 2 - position and 2'- position in biphenyl and the 1 - position and 8 - position in naphthalene. B. Compounds of the Present Disclosure

[0052] The present disclosure provides a compound comprising a ligand L of formula I represented below A [Chemical formula] Formula I wherein X 1 ~X 4 are each independently C or N; X 1a ~X 4a are each independently C or N; at least two of X 1 ~X 4 are C; the X 1 ~X 4 that binds to ring A is C; Z is C or N; R 1 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, and combinations thereof; ring C is a fused ring structure comprising three or more fused hetero rings or carbocyclic rings; R A , R B , and R C each represent zero, mono, or up to the maximum number of substitutions allowed in the relevant ring; each R A , R B , and R C is independently hydrogen or a substituent selected from the group of general substituents defined herein, and any two substituents can be bonded to each other or condensed to form a ring. The ligand L A can complex with a metal M. The metal M can be Os, Ir, Pd, Pt, Cu, Ag, or Au. The ligand L A can combine with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. The other ligands can be preferably selected from the ligands described herein. The other ligands can also be selected from ligands known in the art.

[0053] In some embodiments, each R A ​can be, independently, hydrogen or a substituent selected from the group consisting of preferred general substituents defined herein.

[0054] In some embodiments, each R A can be, independently, hydrogen or a substituent selected from the group consisting of more preferred general substituents defined herein.

[0055] In some embodiments, each R B can be, independently, hydrogen or a substituent selected from the group consisting of preferred general substituents defined herein.

[0056] In some embodiments, each R B can be, independently, hydrogen or a substituent selected from the group consisting of more preferred general substituents defined herein.

[0057] In some embodiments, each R C can be, independently, hydrogen or a substituent selected from the group consisting of preferred general substituents defined herein.

[0058] In some embodiments, each R C can be, independently, hydrogen or a substituent selected from the group consisting of more preferred general substituents defined herein.

[0059] In some embodiments, X 1 ~X 4 can each be C.

[0060] In some embodiments, R 1 can be a partially or fully deuterated alkyl group. In some embodiments, R 1 can be a CD 3 group.

[0061] In some embodiments, at least one R A is an alkyl group that is partially or fully deuterated. In some embodiments, at least one R A is a CD 3 group.

[0062] In some embodiments, X 1a ~X 4a are each C. In some embodiments, at least one of X 1a ~X 4a is N. In some embodiments, at least two of X 1a ~X 4a are N. In some embodiments, ring A is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, and triazine.

[0063] In some embodiments, Z can be C.

[0064] In some embodiments, ring C can independently include rings selected from 5-membered rings and 6-membered rings. In some embodiments, ring C can include two 6-membered rings and one 5-membered ring. In some embodiments, ring C can include three 6-membered rings and one 5-membered ring. In some embodiments, ring C can include two 6-membered rings and two 5-membered rings.

[0065] In some embodiments, X 2 can be attached to ring A.

[0066] In some embodiments, X 3 can be attached to ring A.

[0067] In some embodiments, ring A can be 2,6-disubstituted.

[0068] In one embodiment, the present disclosure provides a ligand of formula II below. [Chemical formula] Formula II In the formula, X is selected from the group consisting of O, S, Se, NR, CRR', and SiRR'; R and R' are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; X 5 ~X 12 are each independently C or N; X that forms a bond with M 5 ~X 12 is C; the two R C substituents can be bonded to each other or condensed to form a ring.

[0069] In some embodiments of Formula II, X can be O.

[0070] In some embodiments of Formula II, X 5 ~X 12 can each be C. In some embodiments, at least one of X 5 ~X 12 is N. In some embodiments, at least one of X 9 ~X 12 is N. In some embodiments, X 9 is N, and X 5 ~X 8 and X 10 ~X 12 are C. In some embodiments, the maximum number of N atoms that can be bonded to each other within the ring is 2.

[0071] In some embodiments of Formula II, the two R CThe substituents can be bonded to each other to form a 5- or 6-membered aromatic ring which may be further condensed and substituted. In some embodiments, the 6-membered aromatic ring is selected from the group consisting of benzene, pyridine, pyrimidine, pyrazine, pyridazine, and triazine. In some embodiments, the 6-membered aromatic ring is benzene. In some embodiments of Formula II, two R C The substituents can be bonded to each other to form a substituted or unsubstituted group selected from the group consisting of furan, thiophene, pyrrole, cyclopentadiene, and their benzo-variants.

[0072] In some of the above embodiments, ligand L A can be selected from the group consisting of the following.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0073] In some of the above embodiments, ligand L A is of formula L Ai-N-MDefined in a first LA list having, where i is an integer from 1 to 14, N is an integer from 1 to a maximum of 7, and M is an integer from 1 to 649; each L Ai-N 's structure is defined as follows.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0074] In some embodiments, the present disclosure provides a compound of formula M(L A ) x (L B ) y (L C ) z wherein L A is a compound described herein, and L B and L C are each bidentate ligands; 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 metal M.

[0075] In some embodiments, M(L A ) x (L B ) y (L C ) z is 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 different from each other.

[0076] In some embodiments, M(L A ) x (L B ) y (L C ) z can be a compound of the formula Pt(L A )(L B ), where L A and L B may be the same or different. In some embodiments, L A and L B are joined to form a tetradentate ligand.

[0077] In some embodiments of the compound of the formula M(L A ) x (L B ) y (L C ) z , L B and L C can each independently be selected from the group consisting of the following.

Chemical formula

Chemical formula

[0078] In some embodiments of the compound of formula M(L A ) x (L B ) y (L C ) z L B and L C can each independently be selected from the group consisting of the following.

Chemical formula

Chemical formula

Chemical formula

[0079] In some embodiments of the compound of general formula M(L A ) x (L B ) y (L C ) z the compound has compound A-i-N-M having formula Ir(L Ai-N-M ) 3 , compound B-i-N-M-k having formula Ir(L Ai-N-M )(L Bk ) 2 , compound Ir(L Ai-N-M ) 2 (LBk )-containing compound C-i-N-M-k, formula Ir(L Ai-N-M )(L Cj-I ) 2 )-containing compound D-i-N-M-j-I, or formula Ir(L Ai-N-M )(L Cj-II ) 2 )-containing compound E-i-N-M-j-II, selected from the group consisting of, wherein i is an integer from 1 to 14, N is an integer from 1 to a maximum of 5, M is an integer from 1 to 649, k is an integer from 1 to 264, j is an integer from 1 to 768; L B1 ~L B264 has a structure defined in the first LB list shown below. [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] L C is selected from the first LC list group consisting of the following. The following: [Chemical formula] having a structure based onCj-I ; and the following: [Chemical formula] L having a structure based on Cj-II ; wherein j is an integer from 1 to 768, and L Cj-I and L Cj-II for each L in Cj in, R 1’ and R 2’ are defined as shown in the following first LC list. [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] wherein R D1 ~R D192 have the following structure. [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

[0080] Formula M(L A ) x (L B )y (L C ) z In some embodiments of the compound of (L B ), L B1 is L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B32 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B58 , L B160 , L B162 , L B164 , L B168 , L B172 , L B175 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B222 , L B231 , L B233 , L B235 , L B237 , L B240 , L B242 , L B244 , L B246 , L B248 , L B250 , L B252 , L B254 , L B256 , L B258 , L B260 , L B262 , L B263 , and L B264 and can be selected from the group consisting of.

[0081] In some embodiments, L B is L B1 , L B2 , L B18 , L B28, L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B132 , L B136 , L B138 , L B142 , L B156 , L B162 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , and L B237 can be selected from the group consisting of.

[0082] L A and L B are defined as above in the formula M(L A ) x (L B ) y (L C ) z In some embodiments of the compounds having, L C is defined such that its corresponding R 1 and R 2 are selected from the following structures: L Cj-I and L Cj-II can be selected only from the second LC list group consisting of: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D18 , R D20 , R D22 , R D37 , R D40 , R D41 , R D42 , R D43 , R D48 , R D49 , R D50 , R D54 , R D55 , R D58 , R D59, R D78 , R D79 , R D81 , R D87 , R D88 , R D89 , R D93 , R D116 , R D117 , R D118 , R D119 , R D120 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D147 , R D149 , R D151 , R D154 , R D155 , R D161 , R D175 , and R D190 .

[0083] In some embodiments, L C is defined such that its corresponding R 1 and R 2 are selected from a third LC list group consisting only of L Cj-I and L Cj-II : R D1 , R D3 , R D4 , R D5 , R D9 , R D17 , R D22 , R D43 , R D50 , R D78 , R D116 , R D118 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D149 , R D151 , R D154 , R D155 , and R D190 .

[0084] L A and L B is defined as above by formula M(L A ) x (L B ) y (L C ) z In some embodiments of the compounds having C L can be selected from a fourth LC list group consisting of the following.

Chemical formula

Chemical formula

[0085] Formula M(L A ) x (L B ) y (L C ) z In some embodiments of the compounds having A L is selected from the group consisting of the structures defined in the first LA list described above, and L B is selected from the group consisting of the structures defined in the first LB list described above, and L C is selected from the group consisting of the structures defined in the first LC list described above.

[0086] In some embodiments, the compound is a compound A-i-N-M having the formula Ir(L Ai-N-M ) 3 , a compound B-i-N-M-k having the formula Ir(L Ai-N-M )(L Bk ) 2 , a compound C-i-N-M-k having the formula Ir(L Ai-N-M ) 2 (L Bk ), a compound D-i-N-M-j-I having the formula Ir(L Ai-N-M )(L Cj-I ) 2 , or a compound having the formula Ir(L Ai-N-M )(L Cj-II ) 2Selected from the group consisting of compound E-i-N-M-j-II having, wherein i is an integer from 1 to 14, N is an integer from 1 to a maximum of 5, M is an integer from 1 to 649, k is an integer from 1 to 264, j is an integer from 1 to 768; each L Ai-N-M 、L Bk 、L Cj-I 、and L Cj-II are defined as above.

[0087] In some embodiments, the compound is selected from the group of compound lists consisting of the following.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0088] In another aspect, the present disclosure also provides an OLED device including a first organic layer containing the compound disclosed in the compound section of the present disclosure.

[0089] In some embodiments, the OLED includes an organic layer containing a compound of Formula I shown below.

Chemical formula

[0090] In some embodiments, the OLED includes an organic layer containing a compound of Formula II shown below.

Chemical Formula

[0091] In some embodiments, the OLED can include an organic layer containing a compound of L described herein. Ax-N

[0092] In some embodiments, the OLED can include an organic layer containing a compound of the formula M(L A ) x (L B ) y (L C ) z wherein L A is a compound described herein, and L B and L C are each bidentate ligands; 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.

[0093] In some embodiments, the OLED can include an organic layer containing a compound of M(L A ) x (L B ) y (L C ) z which can have the formula Ir(L A ) 3 , the formula Ir(L A )(L B ) 2 , or the formula Ir(L A ) 2 (L C ) and wherein L A , L B , and L C can have the structures described herein. In some embodiments, L B can be a compound selected from the group consisting of L B1 ~L B263 described herein. In some embodiments, LC can be selected from the group consisting of structures defined in the LC list described herein.

[0094] In some embodiments, the OLED is Ir(L A ) 3 , Ir(L A )(L B ), 2 Ir(L A ), 2 (L B ), A Ir(L 2 (L C ), A and B Ir(L C )(L A )(L B ) C ; L

[0095] In some embodiments, the OLED is M(L A ) x (L B ) y (L C ) z and can include an organic layer having a compound of A Pt(L B )(L A ), B wherein L A and L B may be the same or different. In some embodiments, L

[0096]

[0097] In some embodiments, the organic layer can be a light-emitting layer, and the compounds described herein can be light-emitting dopants or non-light-emitting dopants.In some embodiments, the organic layer may further include a host, the host includes triphenylene containing benzo-fused thiophene or benzo-fused furan, and any substituent in the host is independently 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 、C n H 2n -Ar 1 selected from the group consisting of non-condensed substituents, or can be unsubstituted, n is 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.

[0098] In some embodiments, the organic layer may further include a host, the host includes at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0099] In some embodiments, the host can be selected from a host group selected from the group consisting of the following.

Chemical formula

[0100] In some embodiments, the organic layer can further include a host, and the host includes a metal complex.

[0101] In some embodiments, the compounds described herein can be sensitizers, and the device can further include an acceptor, and the acceptor can be selected from a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0102] In yet another aspect, the OLEDs of the present disclosure can also include a light-emitting region including the compounds disclosed in the compound section of the present disclosure.

[0103] In some embodiments, the light-emitting region can include a compound including the ligand L of Formula I A [Chemical] Formula I wherein X 1 ~X 4 are each independently C or N; X 1a ~X 4a are each independently C or N; at least two of X 1 ~X 4 are C; the X 1 ~X 4 bonded to ring A are C; Z is C or N; R 1 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, and combinations thereof; C is a fused ring structure including three or more fused hetero rings or carbocyclic rings; R A , R B , and R​C represents, respectively, zero, mono, or up to the maximum number of substitutions allowed in the relevant ring; each R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of common substituents defined herein, and any two substituents can be bonded or fused to each other to form a ring.

[0104] In yet another aspect, the present disclosure also provides a consumer product comprising an organic light emitting device (OLED) having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound disclosed in the compound section of the present disclosure.

[0105] In some embodiments, the consumer product comprises an organic light emitting device (OLED) having an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer can comprise a compound comprising a ligand L of Formula I A .

Chemical formula

[0106] In some embodiments, the consumer product is a flat panel display, computer monitor, medical monitor, television, bulletin board, indoor or outdoor lighting and / or signaling light, head-up display, fully or partially transparent display, flexible display, laser printer, telephone, mobile phone, tablet, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay with a diagonal less than 2 inches, 3-D display, virtual reality or augmented reality display, vehicle, video wall including multiple displays arranged side by side, theater or stadium screen, phototherapy device, and signboard.

[0107] Generally, an OLED includes 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 move to the oppositely charged electrodes, respectively. When an electron and a hole are localized on the same molecule, an "exciton", which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted via a photoelectron emission mechanism when the exciton relaxes. In some cases, the exciton can be localized on an excimer or an exciplex. Non-radiative mechanisms such as thermal relaxation may occur, but are generally considered undesirable.

[0108] Materials and configurations of some OLEDs are described in U.S. Patent No. 5,844,363, U.S. Patent No. 6,303,238, and U.S. Patent No. 5,707,745, which are incorporated herein by reference in their entirety.

[0109] Initial OLEDs used luminescent molecules (“fluorescence”) that emit light from their singlet state, as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated herein by reference in its entirety. Fluorescent emission generally occurs within a time frame of less than 10 nanoseconds.

[0110] More recently, OLEDs having a luminescent material (“phosphorescence”) that emits light from the triplet state 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”), which are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in U.S. Patent No. 7,279,704, paragraphs 5 - 6, which is incorporated herein by reference.

[0111] FIG. 1 shows an organic light emitting device 100. The figure is not necessarily to scale. Device 100 can include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, a light emitting 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 composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by depositing the described layers in sequence. The properties and functions of these various layers, as well as examples of materials, are described in more detail in US7,279,704, paragraphs 6 - 10, which are incorporated herein by reference.

[0112] For each of these layers, further examples are available. For example, the flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety, F 4 -TCNQ doped at a molar ratio of 50:1 with m-MTDATA. Examples of the light-emitting material and the host material are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety, Li doped at a molar ratio of 1:1 with BPhen. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties, disclose examples of cathodes including a composite cathode having a thin layer of a metal such as Mg:Ag having a transparent, conductive, sputter-deposited ITO layer thereon. The theory and use of the blocking layer 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 herein by reference in their entireties. Examples of the injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0113] Figure 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, a light-emitting layer 220, a hole transport layer 225, and an anode 230. The device 200 can be fabricated by depositing the described layers in sequence. Since the most common OLED configuration has a cathode disposed on top of the anode and device 200 has a cathode 215 disposed under the anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described for device 100 may be used in the corresponding layers of device 200. Figure 2 provides an example of how some layers can be omitted from the structure of device 100.

[0114] The simple layer structures illustrated in FIGS. 1 and 2 are provided as non-limiting examples, and it is understood that embodiments of the present disclosure can 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 can be realized by combining the various layers described in various ways, or the layers can 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 the 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. Also, the layers may have various sub-layers. The names given to the various layers herein are not intended to be limiting. For example, in device 200, the hole transport layer 225 transports holes and injects holes into the light-emitting 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 the cathode and the anode. The organic layer may include a single layer or may further include multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.

[0115] OLEDs (PLEDs), etc., composed of polymer materials such as those disclosed in U.S. Patent No. 5,247,190 to Friend, which is incorporated by reference in its entirety, may be used with structures and materials not specifically described. As a further example, an OLED having a single organic layer may be used. The OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 to Forrest, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layer structure illustrated in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces for improving outcoupling, such as mesa structures described in U.S. Patent No. 6,091,195 to Forrest, which is incorporated by reference in its entirety, and / or recessed structures described in U.S. Patent No. 5,834,893 to Bulovic, which is incorporated by reference in its entirety.

[0116] Unless otherwise specified, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated herein by reference in their entirety, inkjet, organic vapor deposition (OVPD) such as those described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated herein by reference in its entirety, and organic vapor jet printing (OVJP) such as those described in U.S. Pat. No. 7,431,968, which is incorporated herein 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 a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include masks such as those described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated herein by reference in their entirety, deposition via cold welding, and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may be used. The materials to be deposited can be modified to be compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups that are branched or unbranched and preferably contain at least 3 carbons can be used in small molecules to enhance the ability to undergo solution processing. Substituents having 20 or more carbons can be used, and a range of 3 to 20 carbons is preferred. Materials having an asymmetric structure can have better solution processability than those having a symmetric structure, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents can be used to enhance the ability of small molecules to undergo solution processing.

[0117] Devices fabricated in accordance with embodiments of the present disclosure 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 an environment containing moisture, vapor, and / or gas, etc. The barrier layer can be deposited on the substrate, above, below, or adjacent to the electrodes, or on any other part of the device including the edges. The barrier layer may include a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques and can 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 materials and non-polymeric materials as described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are hereby incorporated by reference in their entirety. For the mixture 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 the polymeric material to the non-polymeric material can range from 95:5 to 5:95. The polymeric material and the non-polymeric material can be made from the same precursor material. In one example, the mixture of the polymeric material and the non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0118] Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into various electrical products or intermediate components. Such electrical products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels, etc.) that can be utilized by end-user product manufacturers. Such electronic component modules can optionally include drive electronics and / or power supplies. Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of consumer products having one or more incorporated electronic component modules (or units). Consumer products including OLEDs containing the compounds of the present disclosure in the organic layers of the OLEDs are disclosed. Such consumer products include any type of product including one or more light sources and / or one or more certain types of visual displays. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, bulletin boards, indoor or outdoor lighting and / or lights for signal transmission, head-up displays, fully or partially transparent displays, flexible displays, bendable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays arranged side by side, theater or stadium screens, phototherapy devices, and billboards. Various control mechanisms including passive matrix and active matrix can be used to control the devices fabricated in accordance with the present disclosure. Many of the devices are intended for use within a temperature range comfortable for humans, such as from 18 degrees Celsius to 30 degrees Celsius, more preferably room temperature (20 - 25 °C), but can also be used outside this temperature range, for example, from -40 degrees Celsius to +80 °C.

[0119] Further details regarding OLEDs, and the definitions described above, can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0120] 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 utilize the materials and structures. More generally, organic devices such as organic transistors may utilize the materials and structures.

[0121] In some embodiments, the OLED has one or more properties selected from the group consisting of being flexible, bendable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further includes a layer including carbon nanotubes.

[0122] In some embodiments, the OLED further includes a layer including a delayed fluorescence emitter. In some embodiments, the OLED includes an RGB pixel array or a white and color filter pixel array. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal less than 10 inches or an area less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is an illumination panel.

[0123] In some embodiments, the compound can be a luminescent dopant. In some embodiments, the compound can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. Application No. 15 / 700,352, which is incorporated herein by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the luminescent 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 the others). When more than one ligand coordinates to the metal, in some embodiments, all of these ligands can be identical. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, all of the ligands can be different from each other. This also applies to embodiments where the ligands coordinating to the metal can bind to other ligands coordinating to the same metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, when the coordinating ligands are bound to each other, in some embodiments, all of the ligands can be identical, and in some other embodiments, at least one of the bound ligands can be different from the other ligands.

[0124] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, and one or more layers in the OLED can include an acceptor in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound can be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor, and the acceptor emits energy or further transfers the energy to a final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in 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 occur from any or all of the sensitizer, the acceptor, and the final emitter.

[0125] According to another aspect, a composition comprising the compounds described herein is also disclosed.

[0126] The OLEDs disclosed herein can be incorporated into one or more of consumer products, electronic component modules, and lighting panels. The organic layer can be a light-emitting layer, and in some embodiments, the compound can be a light-emitting dopant, and in other embodiments, the compound can be a non-light-emitting dopant.

[0127] In still another aspect of the present disclosure, a composition comprising the novel compounds disclosed herein is described. The composition can also include one or more components selected from the group consisting of solvents, hosts, hole injection materials, hole transport materials, electron blocking materials, hole blocking materials, and electron transport materials disclosed herein.

[0128] This disclosure encompasses any chemical structure that includes the novel compounds of this disclosure, or monovalent or polyvalent variants thereof. In other words, the inventive compounds or their monovalent or polyvalent variants can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermolecules). As used herein, a "monovalent variant of a compound" refers to a moiety that is identical to the said compound except that one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. As used herein, a "polyvalent variant of a compound" refers to a moiety that is identical to the said compound except that more than one hydrogen has been removed and replaced with bonds to the remainder of the chemical structure. In the example of a supramolecule, the inventive compound can also be incorporated into the supramolecular complex without covalent bonds. D. Combinations of the Compounds of the Present Disclosure with Other Materials

[0129] The materials described herein as useful in certain layers 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 combination 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 can be useful in combination with the compounds disclosed herein, and one of ordinary skill in the art can readily access the literature to identify other materials that can be useful in combination. a) Conductive (electrically conductive) dopants:

[0130] The charge transport layer is doped with a conductive dopant, which greatly changes the density of charge carriers and thereby its conductivity. The conductivity can be increased by generating charge carriers in the matrix material or depending on the type of dopant, and a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant, and an n-type conductive dopant is used in the electron transport layer.

[0131] Non-limiting examples of conductive dopants that can be used in an OLED in combination with the materials disclosed herein are illustrated below along with the documents disclosing these materials. EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012

Chemical formula

Chemical formula

[0132] The hole injection / transport materials used in the present disclosure are 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 materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorinated hydrocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; MoO xMetal oxide derivatives such as; p-type semiconductor organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds, but not limited thereto.

[0133] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structures. [Chemical formula]

[0134] Ar 1 from Ar 9Each of them 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, azulene, etc.; 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, etc.; and the same or different types of groups selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and 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, and are selected from the group consisting of 2 to 10 cyclic structural units bonded to each other. Each Ar can be unsubstituted or 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 acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0135] In one embodiment, Ar 1 from Ar9 is [Chemical formula] (wherein k is an integer from 1 to 20; X 101 to X 108 is C (including C(CH)) or N; Z 101 is NAr 1 O, or S; Ar 1 has the same group as defined above.) is independently selected from the group consisting of

[0136] Examples of the metal complexes used in HIL or HTL include, but are not limited to, the following general formula [Chemical formula] wherein Met is a metal that can have an atomic weight greater than 40; (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 an auxiliary ligand; k' is an integer value from 1 to the maximum number of ligands that can bind to the metal; and k'+k'' is the maximum number of ligands that can bind to the metal

[0137] In one embodiment, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another embodiment, (Y 101 -Y 102 ) is a carbene ligand. In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex has a minimum oxidation potential of less than about 0.6 V in solution with respect to the Fc + / Fc couple

[0138] Non-limiting examples of HIL materials and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the documents that disclose these 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, US06517957, 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, US5061569, US5639914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018 [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] c) EBL:

[0139] The electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons emitted from the light-emitting layer. The presence of such a blocking layer in the device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. Also, the blocking layer can be used to limit light emission to a desired region of the 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 the EBL contains the same molecule or the same functional group as that used as one of the hosts described below. d) Host:

[0140] 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 contain a host material using the metal complex as a dopant material. The host material is not particularly limited, and any metal complex or organic compound can be used as long as the triplet energy of the host is greater than that of the dopant. Any host material can be used together with any dopant as long as the triplet criterion is satisfied.

[0141] Examples of metal complexes used as host materials preferably have the following general formula.

Chemical formula

[0142] In one aspect, the metal complex is the following complex.

Chemical formula

[0143] In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y 103 -Y 104 ) is a carbene ligand.

[0144] In one aspect, the host compound comprises at least one 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; 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 same or different types of groups selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and composed of 2 to 10 cyclic structural units directly or bonded to each other 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 option within each group can be unsubstituted or 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 acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0145] In one embodiment, the host compound contains at least one of the following groups in the molecule.

Chemical formula

Chemical formula

[0146] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the documents disclosing these 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, US7154114, 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, US9466803

Chem.

Chem.

Chem.

Chem.

[0147] One or more additional emitter dopants can be used in combination with the compounds of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compound can be used as long as the compound is typically used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can generate light through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0148] Non-limiting examples of emitter materials that can be used in an OLED in combination with the materials disclosed herein are exemplified below along with the documents disclosing these materials. CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, US06699599, US06916554, 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, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US7332232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586, US8871361, 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,

Chem.

Chem.

Chem.

Chem.

[0149] Using a hole blocking layer (HBL), the number of holes and / or excitons emitted from the light emitting layer can be reduced. The presence of such a blocking layer in the device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. Also, the use of a blocking layer can limit the light emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (farther 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 (farther from the vacuum level) and / or higher triplet energy than one or more of the hosts closest to the HBL interface.

[0150] In one aspect, the compound used in the HBL contains the same molecule or the same functional group as when used in the host described above.

[0151] In another aspect, the compound used in the HBL contains at least one of the following groups in the molecule. [Chemistry] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3. g) ETL:

[0152] The electron transport layer (ETL) may include materials capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or may be doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is typically used for transporting electrons.

[0153] In one aspect, the compound used in the ETL contains at least one of the following groups in the molecule.

Chemical formula

[0154] In another aspect, the metal complex used in the ETL contains, but is not limited to, the following general formula.

Chemical formula

[0155] Non-limiting examples of ETL materials that can be used in an OLED, in combination with the materials disclosed herein, are exemplified below together with the documents disclosing these 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, US6656612, US8415031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535

Chem.

Chem.

Chem.

[0156] In tandem or stacked OLEDs, the CGL plays an important role in performance and consists of an n-doped layer and a p-doped layer for electron and hole injection, respectively. Electrons and holes are supplied from the CGL and the electrodes. The consumed electrons and holes in the CGL are replenished by the electrons and holes injected from the cathode and anode, respectively, and then the bipolar current gradually reaches a stable state. Typical CGL materials include n-type and p-type conductive dopants used in the transport layer.

[0157] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically mentioned substituents such as, but not limited to, methyl, phenyl, pyridyl, etc. can be in their non-deuterated, partially deuterated, and fully deuterated versions. Similarly, classes of substituents such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc. can also be in their non-deuterated, partially deuterated, and fully deuterated versions. It is understood that the various embodiments described herein are merely by way of example and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the invention. Accordingly, the invention as claimed can 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 the various theories as to why the invention works are not intended to be limiting. Experiment

[0158] Scheme

[0159] Example of the Invention Ir(L B26 ) 2 (L A3-1-1 ) Synthesis

Chemical Formula

[0160] Process 1

Chem.

[0161] Process 2

Chem.

[0162] Process 3 [Chemical Structure] 5-(methyl-d 3 )-2-(naphtho[1,2-b]benzofuran-10-yl)-4-(2,4,5-tris(methyl-d 3)Synthesis of (phenyl)pyridine: 5-Methyl-2-(naphtho[1,2-b]benzofuran-10-yl)-4-(2,4,5-trimethylphenyl)pyridine (3.27 g, 7.65 mmol) and ((methyl-d3)sulfinyl)methane-d3 (25 ml, 356 mmol) were added to a 100 ml three-necked round-bottom flask. Subsequently, the air in the flask was degassed three times and replaced with nitrogen. Sodium 2-methylpropane-2-olate (0.368 g, 3.82 mmol) was added, and the operations of degassing and nitrogen replacement were repeated. The reaction mixture was heated to 90 °C under nitrogen. Subsequently, the reaction mixture was transferred to a 500 ml three-necked round-bottom flask, and 175 mL of DMSO-d6 was further added. The operations of degassing and nitrogen replacement were repeated three times. The reaction mixture was heated to 90 °C under nitrogen. At this time, most of the substances were in solution, and the color of the mixture changed from tan to brown. The flask and the oil bath were covered with aluminum foil; cooled; D 2 O was added and stirred; diluted with water; extracted twice with dichloromethane; the organic matter was washed with a 10% LiCl solution; washed with brine; then dried over magnesium sulfate; filtered; and evaporated to obtain a yellow solid (wt. = 5.23 g). The crude material was purified using a silica gel plug eluted with dichloromethane.

[0163] Process 4 [Chemical formula] Synthesis of Examples of the Invention: The triflate salt (1.9 g, 2.430 mmol), 5-(methyl-d3)-2-(naphtho[1,2-b]benzofuran-10-yl)-4-(2,4,5-tris(methyl-d3)phenyl)pyridine (1.923 g, 4.37 mmol), DMF (50 ml), and 2-ethoxyethanol (50.0 ml) were added to a 500 ml round-bottom flask. The flask was degassed three times and replaced with nitrogen. The reaction mixture was heated at 100 °C (oil bath) overnight (~16 hours). The reaction was heated at 100 °C for 2.5 weeks. The reaction mixture was diluted with methanol; filtered through a Celite pad; washed with methanol; the material was recovered by washing the Celite with DCM; the DCM was evaporated to obtain a solid. The crude material was purified by column chromatography eluting with 70% toluene / heptane and then pure toluene. 1 g (41%) of the product was obtained.

[0164] Synthesis of Comparative Examples

Chemical Formula

[0165] Device Examples

[0166] All of the example devices were fabricated by thermal evaporation under high vacuum (<10 -7 Torr). The anode electrode was 800 Å indium tin oxide (ITO). The cathode consisted of 10 Å Liq (lithium 8-hydroxyquinolate) and 1,000 Å Al. All of the devices were immediately, after fabrication, placed in a nitrogen glove box (<1 ppm H 2 O and O 2)Among them, it was encapsulated with a glass lid sealed with an epoxy resin, and a moisture getter was placed in the package. The organic laminate of the device example consisted of, in order from the ITO surface, 100 Å of HAT-CN as a hole injection layer (HIL); 450 Å of HTM as a hole transport layer (HTL); and a light emitting layer (EML) having a thickness of 400 Å. The light emitting layer contained an H-host (H1):E-host (H2) in a 6:4 ratio and 12 wt% of a green emitter. As the ETL, it was 350 Å of Liq (lithium 8-hydroxyquinoline) doped with 40% of ETM. The schematic structure of each device is shown in Table 1. The chemical structures of the device materials are shown below. [Chemical formula] [Chemical formula]

[0167] After fabrication, the electroluminescence (EL) and current density-voltage-luminance (J-V-L) characteristics of each device were measured, and the lifetime test was performed at DC 80 mA / cm 2 and the LT95 was calculated at 1,000 nits (nits). From the LT95 data, an acceleration factor of 1.8 was assumed. The device data was normalized with respect to the comparative example and is shown in Table 2.

[0168] Table 1: Schematic of device structure [Table 1] Table 2: Device performance data [Table 2]

[0169] Comparison of device performance data between the examples and comparative examples of the present invention - Both the efficiency and lifetime of the examples of the present invention are significantly higher than those of the comparative examples. It is presumed that the orientation of the transition dipole moment of the molecule is better when the aryl substitution is partially twisted than when it is simply methyl. This concept is shown in Figure 3.

Description of Symbols

[0170] 100 Organic light-emitting device 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 Protection 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 compound characterized by containing a first ligand L selected from the group consisting of the following formulas Ａ ​ 【Chemical 1】 【Chemical 2】 (R １ is an alkyl group which may be partially or fully deuterated; R Ａ , R Ｂ , and R Ｃ each represents zero, mono, or up to the maximum allowable number of substitutions; Each R Ａ , R Ｂ , and R Ｃ is independently hydrogen, or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; X and Y are each independently selected from the group consisting of O, S, Se, NR, CRR', and SiRR'; R and R' are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R Ｄ represents from zero, mono, up to the maximum number of substitutions tolerated in the relevant ring; Each R Ｄ is, independently, hydrogen, or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; The ligand L Ａ coordinates with the metal Ir; The ligand L Ａ can combine with other ligands to form a three-, four-, five-, or six-coordinate ligand.) However, when the ligand L Ａ is represented by the following formula, the case where X is CRR' is excluded. 【Chemical Formula 3】

2. The compound according to claim 1, wherein X is O.

3. the ligand L Ａ is of the formula L Ａｉ－Ｎ－Ｍ which is defined by the formula, where i is an integer from 1 to 14, N is an integer from 1 to a maximum of 7, M is an integer from 1 to 649; each L Ａｉ－Ｎ is a compound of claim 1 as defined below. [Chemical Formula 4] 【Chemical Formula 5】 【Chemical Formula 6】 【Chemical Formula 7】 (In the formula, each L Ａｉ－Ｎ for, the substituent R １ , R Ａ , and R Ｂ are defined in the following table as a series of M.) 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical 11】 【Chemical 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 (wherein the substituents A to Z'' are defined as follows.) 【Chemical 17】 【Chemical 18】

4. wherein the compound has the formula Ir(L Ａ ), ｘ (L Ｂ ), ｙ (L Ｃ ), ｚ wherein L Ｂ and L Ｃ are each bidentate ligands; 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 of claim 1.

5. The compound has the formula Ir(L Ａｉ－Ｎ－Ｍ ) ３ Compounds Ai-NM having the formula Ir(L Ａｉ－Ｎ－Ｍ ) (L Ｂｋ ) ２ Compounds Bi-NM-k having the formula Ir(L Ａｉ－Ｎ－Ｍ ) ２ (L Ｂｋ ), compounds Ci-NM-k having the formula Ir(L Ａｉ－Ｎ－Ｍ ) (L Ｃｊ－Ｉ ) ２ or the compound Di-NM-j-I having the formula Ir(L Ａｉ－Ｎ－Ｍ ) (L Ｃｊ－ＩＩ ) ２ wherein i is an integer from 1 to 14, N is an integer from 1 up to 7, M is an integer from 1 to 649, k is an integer from 1 to 264, and j is an integer from 1 to 768; Ｂ１ ~L Ｂ２６４ 4. The compound of claim 3 having the structure shown below: 【Chemical 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical 24】 【Chemical 25】 【Chemical 26】 【Chemical 27】 (wherein, L Ｃｊ－Ｉ is as follows: 【Chemical Formula 28】 has a structure based on; L Ｃｊ－ＩＩ is as follows: 【Chemical 29】 has a structure based on; wherein, L Ｃｊ－Ｉ and L Ｃｊ－ＩＩ For each L in Ｃｊ In, R １’ and R ２’ are defined as shown below.) 【Chemical Formula 30】 【Chemical 31】 【Chemical Formula 32】 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 (wherein, R Ｄ１ to R Ｄ１９２ have the following structures.) 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemical 40】

6. Ir(L Ａ )(L ｘ )(L Ｂ )(L ｙ )(L Ｃ )(L ｚ ), wherein L Ｂ is L Ｂ１ to L Ｂ２６４ as defined in claim 5, and L Ｃ is L Ｃｊ－Ｉ or L Ｃｊ－ＩI as defined in claim 5, the compound according to claim 4.

7. Ir(L Ａ )(L ｘ )(L Ｂ )(L ｙ )(L Ｃ )(L ｚ ), where z is 0 and L Ｂ is L Ｂ１ 、 L Ｂ２ 、 L Ｂ１８ 、 L Ｂ２８ 、 L Ｂ３８ 、 L Ｂ１０８ 、 L Ｂ１１８ 、 L Ｂ１２２ 、 L Ｂ１２４ 、 L Ｂ１２６ 、 L Ｂ１２８ 、 L Ｂ１３０ 、 L Ｂ３２ 、 L Ｂ１３４ 、 L Ｂ１３６ 、 L Ｂ１３８ 、 L Ｂ１４０ 、 L Ｂ１４２ 、 L Ｂ１４４ 、 L Ｂ１５６ 、 L Ｂ５８ 、 L Ｂ１６０ 、 L Ｂ１６２ 、 L Ｂ１６４ 、 L Ｂ１６８ 、 L Ｂ１７２ 、 L Ｂ１７５ 、 L Ｂ２０４ 、 L Ｂ２０６ 、 L Ｂ２１４ 、 L Ｂ２１６ 、 L Ｂ２１８ 、 L Ｂ２２０ 、 L Ｂ２２２ 、 L Ｂ２３１ 、 L Ｂ２３３ 、 L Ｂ２３５ 、 L Ｂ２３７ 、 L Ｂ２４０ 、 L Ｂ２４２ 、 L Ｂ２４４ 、 L Ｂ２４６ 、 L Ｂ２４８ 、 L Ｂ２５０ 、 L Ｂ２５２ 、 L Ｂ２５４ 、 L Ｂ２５６ 、 L Ｂ２５８ 、 L Ｂ２６０ 、 L Ｂ２６２ 、 L Ｂ２６３ 、 and L Ｂ２６４ 、 The compound according to claim 4, selected from the group consisting of

8. An organic light-emitting device (OLED), comprising an anode; a cathode; and an organic layer disposed between the anode and the cathode and containing the compound according to claim 1.

9. A consumer product comprising an organic light-emitting device (OLED), wherein the organic light-emitting device (OLED) has an anode; has a cathode; and an organic layer disposed between the anode and the cathode and containing the compound according to claim 1.

10. The compound according to claim 1, characterized in that the compound is selected from the group consisting of the following. 【Chemical Formula 41】 【Chemical 42】 【Chemical 43】 【Chemical 44】 【Chemical 45】 【Chemical Formula 46】

Images