Organic electroluminescent materials and devices

Abstract

This application relates to organic electroluminescent materials and devices. The invention provides organometallic compounds having ligands L of formula I A : Formulations comprising these organometallic compounds are also provided. In addition, OLEDs and related consumer products utilizing these organometallic compounds are provided.

Description

[0001] This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 63 / 082,649, filed September 24, 2020, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD

[0002] The present disclosure relates generally to organometallic compounds and formulations and various uses thereof, including as emitters in devices such as organic light emitting diodes and related electronic devices. BACKGROUND

[0003] Opto-electronic devices that make use of organic materials are becoming increasingly important for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential to be lower cost than alternative devices that use inorganic materials. In addition, the inherent properties of organic materials, such as their flexibility, can make them well suited for particular applications, such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic light emitting detectors.

[0004] OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in the display, lighting, and back-lighting applications.

[0005] One application for phosphorescent emission is full color displays. Industry standards for such displays require appropriate red, green, and blue emitters to produce a full color display. Alternatively, an OLED can be designed to emit white light. In conventional liquid crystal displays, color filters are used to produce red, green, and blue pixels. The same technology can be used for OLEDs. A white OLED can be used with a color filter to produce red, green, and blue sub-pixels. Alternatively, a single white OLED can be designed and fabricated to have different efficiencies for different colors of light. These different efficiencies can be produced by positioning the single OLED to emit light through different colors of optical interference layers. SUMMARY

[0006] In one aspect, the present disclosure provides a compound comprising a ligand L of Formula I: A

[0007]

[0008] wherein each of Part A and Part B is independently a monocyclic or polycyclic ring structure containing a 5- and / or 6-membered carbocyclic and / or heterocyclic ring; each of Z 1 -Z 4 is independently C or N, each of Z 3 and Z 4 ​at least one of A and B is C; K 1 and K 2 each independently is a direct bond, O, or S; X 1 -X 7 each of A, B, and C is independently C or N, X 3 or X 7 at least one of A, B, and C is N; represents a single or double bond;

[0009] two wavy lines represent the point of attachment to two adjacent ring carbon atoms of moiety B; the maximum number of N atoms that can be connected to each other is two; R A , R B , and R C each represents zero, one, or up to the maximum number of allowed substitutions for the ring to which it is attached; R A , R B , and R C each independently is hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and any two adjacent R A , R B , or R C may be connected or fused to form a ring, wherein ligand L A is coordinated to M via the two indicated dashed lines; wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and wherein ligand L A may be connected to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0010] In another aspect, the present disclosure provides a formulation comprising a compound of Formula I ligand L A as described herein.

[0011] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound of Formula I ligand L A as described herein.

[0012] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of Formula I ligand L A as described herein. BRIEF DESCRIPTION OF DRAWINGS

[0013] Figure 1 An organic light emitting device is shown.

[0014] Figure 2 An inverted organic light emitting device without a separate electron transport layer is shown.

[0015] Figure 3Several emission spectra of representative compounds of the disclosure are shown under a variety of conditions. DETAILED DESCRIPTION

[0016] A. Terminology

[0017] The following terms are defined as follows unless otherwise indicated:

[0018] As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic light emitting devices. Small molecules can also be used to fabricate organic light emitting devices. A small molecule is a molecule that is not a polymer, and small molecules can actually be quite large. In some cases, small molecules can include repeating units. For example, a small molecule can include a long chain alkyl group as a substituent, which can not be removed from the "small molecule" category. Small molecules can also be incorporated into polymers, for example, as a pendent group linear or side chain on a polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built off of a core moiety. A core moiety can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and all dendrimers currently in use in the OLED

[0019] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as "disposed on" a second layer, the first layer is disposed farther from the substrate than is the second layer. Unless stated to the contrary, there can be intervening layers between the first and second layers. For example, a cathode can be described as "disposed on" an anode, even though various organic layers are between the cathode and the anode.

[0020] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium, either in solution or suspension form.

[0021] A ligand can be referred to as "photosensitizing" when it is believed to directly contribute to the photoactive properties of an emissive material. A ligand can be referred to as "auxiliary" when it is believed not to contribute to the photoactive properties of an emissive material, although an auxiliary ligand can alter the properties of a photosensitizing ligand.

[0022] As used herein, and as will be generally 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. Since ionization potential (IP) is measured as a negative energy with respect to the vacuum energy level, a higher HOMO energy level corresponds to a smaller absolute value of IP (a less negative IP). Similarly, a higher LUMO energy level corresponds to a smaller absolute value of electron affinity (EA) (a less negative EA). On a conventional energy level diagram with the vacuum energy level at the top, a LUMO energy level of a material is higher than a HOMO energy level of the same material. A "higher" HOMO or LUMO energy level is thus represented by a closer proximity to the top of such diagram than by a "lower" HOMO or LUMO energy level.

[0023] As used herein, and as will be generally understood by one of ordinary skill 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. Since work functions are typically measured as negative numbers with respect to the vacuum energy level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum energy level at the top, a "higher" work function is thus illustrated as being further from the vacuum energy level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow different conventions than work functions.

[0024] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluoro, chloro, bromo, and iodo.

[0025] The term "acyl" refers to a substituted carbonyl (C(O)-R s ).

[0026] The term "ester" refers to a substituted oxycarbonyl (-O-C(O)-R s or -C(O)-O-R s ) group.

[0027] The term "ether" refers to an -OR s group.

[0028] The terms "sulfide" or "sulfur ether" are used interchangeably and refer to an -SR s group.

[0029] The term "seleno" refers to a -SeR s group.

[0030] The term "sulfanyl" refers to -S(R s groups.

[0031] The term "sulfonyl" refers to -SO2-R s groups.

[0032] The term "phosphinyl" refers to -P(R s )2groups, wherein each R s may be the same or different.

[0033] The term "silyl" refers to -Si(R s )3groups, wherein each R s may be the same or different.

[0034] The term "germyl" refers to -Ge(R s )3groups, wherein each R s may be the same or different.

[0035] The term "silyl" refers to -Si(R s )3groups, wherein each R s may be the same or different. s

[0036] In each of the above, R s may be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferably, R s is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0037] The term "alkyl" refers to and includes straight-chain and branched-chain alkyl groups. Preferred alkyl groups are alkyl groups containing one to fifteen carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group can be optionally substituted.

[0038] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spirocyclic alkyl groups. Preferred cycloalkyl groups are cycloalkyl groups containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl group can be optionally substituted.

[0039] ​The terms "heteroalkyl" or "heterocyclic alkyl" refer to alkyl or cycloalkyl groups having at least one carbon atom substituted with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Additionally, the heteroalkyl or heterocyclic alkyl group may optionally be substituted.

[0040] The term "alkenyl" refers to and includes both straight-chain and branched alkenyl groups. An alkenyl group is essentially an alkyl group comprising at least one carbon-carbon double bond in an alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group comprising at least one carbon-carbon double bond in a cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group in which at least one carbon atom is replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Additionally, alkenyl, cycloalkenyl, or heteroalkenyl groups may optionally be substituted.

[0041] The term "alkynyl" refers to and includes both straight-chain and branched alkynyl groups. An alkynyl group is essentially an alkyl group comprising at least one carbon-carbon triple bond in an alkyl chain. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may optionally be substituted.

[0042] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group that has been substituted with an aryl group. Additionally, aralkyl groups may optionally be substituted.

[0043] 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. Aromatic heterocyclic groups are used interchangeably with heteroaryl groups. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 to 7 ring atoms, including at least one heteroatom, and include cyclic amines such as morpholino, piperidinyl, pyrrolyl, etc., and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Additionally, the heterocyclic group may be optionally substituted.

[0044] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. A polycyclic system may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group; for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group can be optionally substituted.

[0045] The term "heteroaryl" means and includes both monocyclic aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many cases, O, S, or N are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the ring can have one to six heteroatoms. Heteropolycyclic systems can have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl, for example the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclo, and / or heteroaryl. Heteropolycyclic aromatic ring systems can have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolo-dipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indooxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phthalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, phenoxazine, benzofuropyridine, furopyridine, benzothienopyridine, thienopyridine, benzoselenophenopyridine, and selenophenopyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazylene, and nitrogen heteroanalogues thereof. Additionally, the heteroaryl group can be optionally substituted.

[0046] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and their respective nitrogen heteroanalogues are of particular interest.

[0047] The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl as used herein are independently unsubstituted or independently substituted by one or more of the generic substituents.

[0048] In many cases, preferred general substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

[0049] In some cases, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, thio, and combinations thereof.

[0050] In some cases, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, thio, and combinations thereof.

[0051] In other cases, most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0052] The terms "substituted" and "substitution" mean that a substituent other than H is bonded to the relevant position, e.g., carbon or nitrogen. For example, when R 1 represents mono-substitution, then one R 1 must be other than H (i.e., substitution). Similarly, when R 1 represents di-substitution, then two R 1 must be other than H. Similarly, when R 1 represents zero or no substitution, R 1 For example, can be the available valence number of hydrogens of a ring atom, such as the carbon atoms of benzene and the nitrogen atom in pyrrole, or for a ring atom with a fully saturated valence number, simply none, such as the nitrogen atom in pyridine. The maximum number of substitutions possible in a ring structure will depend on the total number of available valences in the ring atoms.

[0053] As used herein, "combination thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art would envision from the applicable 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 haloalkyl substituent; and halogen, alkyl, and aryl can be combined to form a haloaralkyl group. In one example, the term substituted includes combinations of two to four of the listed groups. In another example, the term substituted includes combinations of two to three groups. In yet another example, the term substituted includes combinations of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0054] The "aza" designation in fragments described herein, i.e., aza-dibenzofurans, aza-dibenzothiophenes, and the like, means that one or more of the C-H groups in the corresponding aromatic ring can be replaced with a nitrogen atom, for example and without any limitation, aza-triphenylenes encompass dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.

[0055] 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, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057, which are incorporated herein by reference in their entirety, describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Review) 2007, 46, 7744-65, which are incorporated by reference in their entirety, respectively, describe efficient routes to deuterate methylene hydrogens in benzyl amines and replace aromatic ring hydrogens with deuterium.

[0056] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were an entire molecule (e.g., benzene, naphthalene, dibenzofuran). These different ways of naming substituents or attached fragments are considered equivalent as used herein.

[0057] In some instances, a pair of adjacent substituents can optionally be joined or fused into a ring. Preferred rings are five-, six-, or seven-membered carbocyclic or heterocyclic rings, including both instances in which a portion of the ring formed by the pair of substituents is saturated and in which a portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two substituents in question can be next to each other on the same ring, or on two adjacent rings having the two closest available substitutable positions (such as the 2,2' positions in biphenyl or the 1,8 positions in naphthalene), so long as they can form a stable fused ring system.

[0058] B. Compounds of the Disclosure

[0059] In one aspect, the present disclosure provides a compound comprising a ligand L of Formula I A

[0060]

[0061] wherein:

[0062] each of Part A and Part B is independently a monocyclic or polycyclic ring structure containing a 5- and / or 6-membered carbocyclic and / or heterocyclic ring;

[0063] Z 1 each of Z 4 is independently C or N, wherein at least one of Z 3 and Z 4 is C;

[0064] K 1 each of K 2 is independently a direct bond, O, or S;

[0065] X 1 each of X 7 is independently C or N, wherein at least one of X 3 or X 7 is N;

[0066] represents a single or double bond;

[0067] two wavy lines represent the point of attachment to two adjacent carbon atoms of Part B;

[0068] the maximum number of N atoms that can be connected to each other is two;

[0069] each of R A , R B , and R C represents zero, one, or up to the maximum allowed number of substitutions to its connected ring;

[0070] each R A , R​B and R C independently is hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and

[0071] any two adjacent R A , R B or R C may be joined or fused to form a ring,

[0072] wherein ligand L A is coordinated to M via two indicated dashed lines;

[0073] wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag and Au; and

[0074] wherein ligand L A may be joined to other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

[0075] It should be appreciated that the present disclosure also encompasses the following structures or variations thereof:

[0076]

[0077] In some embodiments, each of R A , R B and R C may independently be 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, sulfido, and combinations thereof.

[0078] In some embodiments, one of Z 1 and Z 2 may be C and the other can be N. In some embodiments, Z 1 and Z 2 may both be C. In some embodiments, Z 3 and Z 4 may both be C. In some embodiments, one of Z 3 and Z 4 may be C and the other can be N.

[0079] In some embodiments, each of X 1 and X 2 may be C. In some embodiments, one of X 1 and X 2 may be C and the other can be N. In some embodiments, one of X 3 or X 7 may be N and the rest can be C. In some embodiments, X 3 -X7 two of X can be N, and the rest can be C. In some embodiments, X 1 -X 7 three of X can be N, and the rest can be C. In some embodiments, X 3 may be N, X 6 may be N, and X 7 may be C. In some embodiments, X 3 may be C, X 4 may be N, and X 7 may be N. In some embodiments, X 5 and X 6 may both be C, and two R C substituents can be linked together to form a 6-membered ring fused to X 5 and X 6 . In some embodiments, X 4 and X 5 may both be C, and two R C substituents can be linked together to form a 6-membered ring fused to X 4 and X 5 . In some embodiments, X 1 and X 2 may both be C, and two R C substituents can be linked together to form a 6-membered ring fused to X 1 and X 2 .

[0080] In some embodiments, moiety A can be a monocyclic 5- or 6-membered aromatic ring. In some embodiments, moiety A can be a bicyclic, tricyclic, or tetracyclic fused ring structure containing 5- and / or 6-membered aromatic rings. In some embodiments, moiety B can be a monocyclic 5- or 6-membered aromatic ring. In some embodiments, moiety B can be a bicyclic, tricyclic, or tetracyclic fused ring structure containing 5- and / or 6-membered aromatic rings.

[0081] In some embodiments, two R A substituents can be linked to form a 5- or 6-membered aromatic ring. In some embodiments, two R B substituents can be linked to form a 5- or 6-membered aromatic ring. In some embodiments, the 5- and 6-membered aromatic rings can be selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, N-heterocyclic carbene, and thiazole.

[0082] In some embodiments, M can be Ir or Pt. In some embodiments, M can be Ir, and the compound can comprise one substituted or unsubstituted phenyl-pyridine ligand. In some embodiments, M can be Ir, and the compound can comprise one substituted or unsubstituted acetylacetonate ligand.

[0083] In some embodiments, the ligand L A is optionally selected from the group consisting of the structures in List 1 below:

[0084]

[0085]

[0086]

[0087] wherein each of moieties A1, B1, B2, and C1is independently a monocyclic ring comprising a 5- or 6-membered carbocyclic or heterocyclic ring.

[0088] In some embodiments, the ligand L A is optionally selected from the group consisting of the structures in List 2 below:

[0089]

[0090]

[0091] wherein:

[0092] T is B, Al, Ga, In;

[0093] Y 1 is independently selected from the group consisting of carbon and nitrogen; 13

[0094] Y' is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , and GeR e R f ;

[0095] each R a and R b independently represents zero, one, or up to the maximum allowed number of substitutions to the ring to which it is attached;

[0096] R a1 , R b1 , R c1 , R d1 , R a , R b , R e , and R f ​Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogroup, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, oxoboryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; general substituents as defined herein; and

[0097] Any two adjacent R A R B R C R a R b R e and R f They can fused or connected to form rings or form polydentate ligands.

[0098] In some embodiments, ligand L A The following groups can be freely composed of structures from List 3:

[0099]

[0100]

[0101] Where R A and R B Same as previously defined.

[0102] In some embodiments, ligand L A Can be L Ai-N-m or L Ai'-N'-m Where i is an integer from 1 to 7, i' is an integer from 8 to 23, N is an integer from 1 to 10, N' is an integer from 1 to 7, and m is an integer from 1 to 649; where each L Ai-N The structure is defined as shown in Listing 4 below:

[0103]

[0104]

[0105]

[0106] Each L Ai'-N' The structure is defined as shown in Listing 5 below:

[0107]

[0108]

[0109]

[0110] as well as

[0111]

[0112] and L Ai-N-m and L Ai'-N'-m substituents J 1 , J 2 , R a1 , R a2 , R b1 and R b2 are as defined in the following table for each m:

[0113]

[0114]

[0115]

[0116] wherein in the definition of substituents R a1 , R a2 , R b1 and R b2 , A = Me, B = CD3, and L = H.

[0117] In some embodiments, the compound can have the formula M(L A ) p (L B ) q (L C ) r wherein L B and L C are each bidentate ligands; and wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p + q + r is the oxidation state of the metal M.

[0118] In some embodiments, the compound can have a formula selected from the group consisting of: Ir(L A )3, Ir(L A )(L B )2, Ir(L A )2(L B ), Ir(L A )2(L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other.

[0119] In some embodiments, the compound can have the formula Pt(L A )(L B ); and wherein L A and L B may be the same or different. In some embodiments, L A and L B are connected to form a tetradentate ligand.

[0120] In some embodiments, L B and L C may each independently be selected from the group consisting of:

[0121]

[0122]

[0123] wherein:

[0124] T is B, Al, Ga, In;

[0125] each of Y 1 through Y 13 is independently selected from the group consisting of carbon and nitrogen;

[0126] Y' is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , and GeR e R f ;

[0127] R e and R f may be fused or connected to form a ring;

[0128] each R a , R b , R c , and R d independently represents zero, one, or up to the maximum allowed number of substitutions to the ring to which it is attached;

[0129] R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R feach of R, R, and R is independently hydrogen or a substituent selected from the group consisting of deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; a general substituent as defined herein; and

[0130] any two adjacent R a , R b , R c , R d , R e , and R f may be fused or linked to form a ring or to form a polydentate ligand.

[0131] In some embodiments, L B and L C may each independently be selected from the group consisting of:

[0132]

[0133]

[0134]

[0135] wherein:

[0136] R a , R b , and R c independently represent zero, one, or up to the maximum allowed number of substitutions to their attached ring;

[0137] R a1 , R b1 , R c1 , R a , R b , R c , R N , R a , R b , and R c independently are hydrogen or a substituent selected from the group consisting of deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and

[0138] any two adjacent R a , R b , and R cmay be fused or linked to form a ring or form a polydentate ligand.

[0139] In some embodiments, when the compound is of formula Ir(L Ai-N-m )3, i is an integer from 1 to 7; N is an integer from 1 to 10, m is an integer from 1 to 649; and the compound is selected from the group consisting of Ir(L A1-1-1 )3 to Ir(L A7-10-649 )3;

[0140] when the compound is of formula Ir(L Ai'-N'-m )3, i' is an integer from 8 to 23, N' is an integer from 1 to 7, m is an integer from 1 to 649; and the compound is selected from the group consisting of Ir(L A8-1-1 )3 to Ir(L A23-7-649 )3;

[0141] when the compound is of formula Ir(L Ai-N-m )(L Bk )2, i is an integer from 1 to 7; N is an integer from 1 to 10, m is an integer from 1 to 649, k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-1-1 )(L B1 )2 to Ir((L A7-10-649 )(L B324 )2;

[0142] when the compound is of formula Ir(L Ai'-N'-m )(L Bk )2, i' is an integer from 8 to 23, N' is an integer from 1 to 7, m is an integer from 1 to 649, k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A8-1-1 )(L B1 )2 to Ir(L A23-7-649 )(L B324 )2;

[0143] when the compound is of formula Ir(L Ai-N-m )2(L Bk ), i is an integer from 1 to 7; N is an integer from 1 to 10, m is an integer from 1 to 649, k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-1-1 )2(L B1 ) to Ir((L A7-10-649 )2(L B324 );

[0144] when the compound is of formula Ir(L Ai'-N'-m )2(L BkWhen i' is an integer from 8 to 23, N' is an integer from 1 to 7, m is an integer from 1 to 649, and k is an integer from 1 to 324; and the compound is selected from Ir(L A8-1-1 )2(L B1 ) to Ir(L A23-7-649 (L) B324 A group consisting of )

[0145] When the compound has the formula Ir(L) Ai-N-m )2(L Cj-I When i is an integer from 1 to 7; N is an integer from 1 to 10; m is an integer from 1 to 649; and j is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1-1 )2(L C1-I ) to Ir((L A7-10-649 )2(L C1416-I) Groups formed;

[0146] When the compound has the formula Ir(L) Ai'-N'-m )2(L Cj-I When i' is an integer from 8 to 23, N' is an integer from 1 to 7, m is an integer from 1 to 649, and j is an integer from 1 to 1416; and the compound is selected from Ir(L A8-1-1 )2(L C1-I ) to Ir(L A23-7-649 )2(L C1416-I A group consisting of )

[0147] When the compound has the formula Ir(L) Ai-N-m )2(L Cj-II When i is an integer from 1 to 7; N is an integer from 1 to 10; m is an integer from 1 to 649; and j is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1-1 )2(L C1-II ) to Ir((L A7-10-649 )2(L C1416-II) Groups formed;

[0148] When the compound has the formula Ir(L) Ai'-N'-m )2(L Cj-II When i' is an integer from 8 to 23, N' is an integer from 1 to 7, m is an integer from 1 to 649, and j is an integer from 1 to 1416; and the compound is selected from Ir(L A8-1-1 )2(L C1-II ) to Ir(L A23-7-649 )2(L C1416-II A group consisting of )

[0149] Among them, each L Ai-N-m and each L Ai'-N'-mhaving the structure as defined herein;

[0150] wherein each L Bk having the structure as defined below in List 6:

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] and

[0162] wherein each L Cj-I having the structure based on the following formula: and

[0163] each L Cj-II having the structure based on the following formula: wherein for each L Cj-I and L Cj-II R Cj and R 201 and R 202 are each independently as defined below in List 7:

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] wherein R D1 to R D246 have the following structure:

[0174]

[0175]

[0176]

[0177]

[0178]

[0179] In some embodiments, the compound can have the formula Ir(L Ai-N-m )(L Bk )2, Ir(L Ai'-N'-m )(L Bk )2, Ir(L Ai-N-m )2(L Bk ), or Ir(L Ai'-N'-m )2(L Bk ), wherein the compound is selected from the group consisting of those compounds whose L Bk ligands correspond to one of the following:

[0180] 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 B132 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B158 , L B160 , L B162 , L B164 , L B168 , LB172 , 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 B264 , L B265 , L B266 , L B267 , L B268 , L B269 , and L B270 .

[0181] In some embodiments, the compound can have the formula Ir(L Ai-N-m )(L Bk )2, Ir(L Ai'-N'-m )(L Bk )2, Ir(L Ai-N-m )2(L Bk ), or Ir(L Ai'-N'-m )2(L Bk ), wherein the compound is selected from the group consisting of those compounds whose L Bk ligands correspond to one of the following:

[0182] L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B126 , L B128 , L B132 , L B136 , L B138 , L B142 , L B156 , L B162 , L B204 , LB206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , L B 237 , L B264 , L B265 , L B266 , L B267 , L B268 , L B269 and L B270 .

[0183] In some embodiments, the compound can have the formula Ir(L Ai-N-m )2(L Cj-I ), Ir(L Ai'-N'-m )2(L Cj-I ), Ir(L Ai-N-m )2(L Cj-II ), or Ir(L Ai'-N'-m )2(L Cj-II ), wherein the compound is selected only from the group of those compounds having L Cj-I or L Cj-II ligands, the respective R 201 and R 202 definitions of which are one of the following structures:

[0184] 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 , RD117 , 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 R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 and R D246 .

[0185] In some embodiments, the compound can have the formula Ir(L Ai-N-m )2(L Cj-I ), Ir(L Ai'-N'-m )2(L Cj-I ), Ir(L Ai-N-m )2(L Cj-II ), or Ir(L Ai'-N'-m )2(L Cj-II ), wherein the compound is only selected from the group of those compounds having L Cj-I or L Cj-II ligands with the corresponding R 201 and R 202 definitions as one of the following structures:

[0186] R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D22 , R D43R 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 R D190 R D193 R D200 R D201 R D206 R D210 R D214 R D215 R D216 R D218 R D219 R D220 R D227 R D237 R D241 R D242 R D245 R D246 .

[0187] In some embodiments, the compound can have the formula Ir(L Ai-N-m )2(L Cj-I ) or Ir(L Ai'-N'-m )2(L Cj-I ), and the compound is selected from the group consisting of those compounds whose ligands L Cj-I have one of the following structures:

[0188]

[0189]

[0190] In some embodiments of the compound, the compound can have Ir(L A )(L Bk )2, Ir(L A )2(L Bk ), the formula Ir(L A )2(L Cj-I ), the formula Ir(L A )2(L Cj-II ), Ir(L A )(L Bk )(L Cj-I ), or Ir(LA )(L Bk )(L Cj-II ), wherein L A is a ligand as defined herein, k is an integer from 1 to 324, each L Bk is as defined herein, j is an integer from 1 to 1416, wherein each L Cj-I and each L Cj-II is as defined herein.

[0191] In some embodiments, the compound can be selected from the group consisting of the following structures in List 8:

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] In some embodiments, the compound can have Formula II:

[0198]

[0199] wherein:

[0200] M 1 is Pd or Pt;

[0201] moieties E and F are each independently a monocyclic or polycyclic ring structure comprising a 5- and / or 6-membered carbocyclic or heterocyclic ring;

[0202] Z 5 and Z 6 are each independently C or N;

[0203] K 1 , K 2 , K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein two are direct bonds;

[0204] L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, no bond, O, S, C=NR', C=CR'R", CR'R', SiRR', BR, BR'R', and NR, wherein at least one of L 1 and L 2 is present;

[0205] X 8 -X 10 each independently C or N;

[0206] R E and R F each independently represents zero, one or up to the maximum allowed number of substitutions to the ring to which it is attached;

[0207] R E and R F each independently is hydrogen or a substituent selected from the group consisting of deuterium, fluoro, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, oxygen boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof;

[0208] where chemically feasible, any two adjacent R A , R B , R C , R E or R F may be joined or fused together to form a ring; and

[0209] the remaining variables are all the same as defined above.

[0210] In some embodiments, both moiety E and moiety F can be 6-membered aromatic rings. In some embodiments, moiety F can be a 5- or 6-membered heteroaromatic ring.

[0211] In some embodiments, Z 5 may be N and Z 6 may be C. In some embodiments, Z 5 may be C and Z 6 may be N.

[0212] In some embodiments, L 1 may be O or CRR'. In some embodiments, L 2 may be a direct bond. In some embodiments, L 2 may be NR.

[0213] In some embodiments, K 1 , K 2 , K 3 , and K 4 may all be direct bonds. In some embodiments, one of K 1 , K 2 , K 3 , or K 4 may be O. In some embodiments, one of K 1 or K 2 may be O.

[0214] In some embodiments, X 8 -X 10 may each be C.

[0215] In some embodiments, the compound can be selected from the group consisting of the following structures in List 9:

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] wherein:

[0222] R x and R y are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;

[0223] R G is independently at each occurrence hydrogen or a substituent selected from the group consisting of deuterium, fluoro, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof; and

[0224] the remaining variables are all the same as defined previously.

[0225] In some embodiments, the compound can be selected from the group consisting of the following structures in List 10:

[0226]

[0227]

[0228]

[0229]

[0230] In some embodiments, the ligand L of Formula I described herein AThe compound of Formula I can be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, percentage deuterated has its ordinary meaning and includes the percentage of possible hydrogen atoms (e.g., the position of hydrogen, deuterium, or halogen) that are replaced with deuterium atoms.

[0231] C. OLEDs and devices of the disclosure

[0232] In another aspect, the present disclosure also provides an OLED device comprising an organic layer containing a compound as disclosed in the above compound section of the present disclosure.

[0233] In some embodiments, the OLED comprises: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand L A of Formula I:

[0234]

[0235] wherein each of Part A and Part B is independently a monocyclic or polycyclic ring structure containing 5- and / or 6-membered carbocyclic and / or heterocyclic rings; Z 1 -Z 4 each of Z 3 and Z 4 is independently C or N, at least one of Z 1 and Z 2 is C; K 1 and K 7 are each independently a direct bond, O, or S; X 3 each of X 7 is independently C or N, at least one of X represents a single or double bond;

[0236] two wavy lines represent the points of attachment to two adjacent ring carbons of Part B; the maximum number of N atoms that can be connected to each other is two; R A , R B , and R C each represent zero, one, or up to the maximum number of allowed substitutions for the ring to which it is attached; R A , R B , and R C are each independently hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and any two adjacent R A , R B , or R C may be connected or fused to form a ring, wherein the ligand L Acoordinated via two designated dashed lines to M; wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and wherein the ligand L A may be connected to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0237] In some embodiments, the organic layer can be an emissive layer and the compound as described herein can be an emissive dopant or a non-emissive dopant.

[0238] In some embodiments, the organic layer can further comprise a host, wherein the host comprises a benzo-fused thiophene or benzo-fused furan containing triphenylene, wherein any substituents in the host are independently selected non-fused substituents from the group consisting of C n H 2n+1 , OC 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, C n H 2n -Ar1, or no substitution, wherein n is 1 to 10; and wherein Ar1and Ar2are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0239] In some embodiments, the organic layer can further comprise a host, wherein the host comprises at least one chemical moiety selected from the group consisting of naphthalene, fluorene, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boratryphenyl- anthracene, aza-fluorene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza- dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b- boratryphenyl-anthracene).

[0240] In some embodiments, the host can be selected from the group consisting of:

[0241]

[0242] and combinations thereof.

[0243] In some embodiments, the organic layer can further comprise a host, wherein the host comprises a metal complex.

[0244] In some embodiments, the compound as described herein can be a sensitizer; wherein the device can further comprise an acceptor; and wherein the acceptor can be selected from the group consisting of a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0245] In yet another aspect, the OLED of the present disclosure can also comprise an emissive region containing a compound as disclosed in the above compound section of the present disclosure.

[0246] In some embodiments, the emissive region can comprise a compound comprising a ligand L A of formula I:

[0247]

[0248] wherein each of Part A and Part B is independently a monocyclic or polycyclic ring structure containing a 5- and / or 6-membered carbocyclic and / or heterocyclic ring; each of Z 1 -Z 4 is independently C or N, at least one of Z 3 and Z 4 is C; each of K 1 and K 2 is independently a direct bond, O, or S; each of X 1 -X 7 is independently C or N, at least one of X 3 or X 7 is N; represents a single or double bond; two wavy lines represent the points of attachment to two adjacent ring carbon atoms of Part B; the maximum number of N atoms that can be connected to each other is two; each of R A , R B , and R C represents zero, one, or up to the maximum allowed number of substitutions to its connected ring; each R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and any two adjacent R A , R B , or R C may be connected or fused to form a ring, wherein ligand L A coordinates to M via the two indicated dashed lines; wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and wherein ligand L A may be connected to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0249] In some embodiments, at least one of the anode, the cathode, or a new layer disposed above the organic emissive layer acts as an enhancement layer. The enhancement layer comprises a plasmonic material that exhibits surface plasmon resonance, which non-radiatively couples to the emitter material and transfers excitation state energy from the emitter material to non-radiative modes of the surface plasmon polaritons. The enhancement layer is disposed at a distance from the organic emissive layer that does not exceed a threshold distance, where due to the presence of the enhancement layer, the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant, and the threshold distance is where the total non-radiative decay rate constant equals the total radiative decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer on the opposite side of the organic emissive layer. In some embodiments, the outcoupling layer is disposed on the emissive layer opposite the enhancement layer, but still able to outcouple energy from the surface plasmon modes of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is scattered as photons into free space. In other embodiments, the energy is scattered from the surface plasmon modes of the device into other modes, such as but not limited to organic waveguide modes, substrate modes, or another waveguide mode. If the energy is scattered into non-free space modes of the OLED, other outcoupling schemes can be incorporated to extract the energy into free space. In some embodiments, one or more intervening layers can be disposed between the enhancement layer and the outcoupling layer. Examples of intervening layers can be dielectric materials, including organic, inorganic, perovskite, oxide, and can include stacks and / or mixtures of these materials.

[0250] The enhancement layer changes the effective properties of the medium in which the emitter material resides, resulting in any or all of the following: reduced emissivity, altered emission line shape, emission intensity variation with angle, altered stability of the emitter material, altered efficiency of the OLED, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both, results in an OLED device that takes advantage of any of the effects described above. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, the OLEDs according to the present disclosure can also include any other functional layers commonly found in OLEDs.

[0251] The enhancement layer can comprise a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmonic material is a material in which the real part of the permittivity crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material includes at least one metal. In such embodiments, the metal can include at least one of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. In general, a metamaterial is a medium composed of different materials in which the overall behavior is different from the sum of its material parts. In particular, we define an optically active metamaterial as a material that simultaneously has a negative permittivity and a negative permeability. On the other hand, a hyperbolic metamaterial is an anisotropic medium in which the permittivity or permeability has different signs for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are strictly distinguished from many other photonic structures, such as Distributed Bragg Reflectors ("DBRs"), because on the length scale of optical wavelengths, the medium should exhibit homogeneity in the direction of propagation. Using terminology that will be understood by those skilled in the art: the permittivity of a metamaterial in the direction of propagation can be described using an effective medium approximation. Plasmonic materials and metamaterials provide methods for controlling the propagation of light, which can enhance OLED performance in a variety of ways.

[0252] In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has periodically, quasi-periodically, or randomly arranged wavelength-sized features, or has periodically, quasi-periodically, or randomly arranged subwavelength-sized features. In some embodiments, the wavelength-sized features and the subwavelength-sized features have sharp edges.

[0253] In some embodiments, the outcoupling layer has wavelength-sized features arranged periodically, quasi-periodically, or randomly, or has subwavelength-sized features arranged periodically, quasi-periodically, or randomly. In some embodiments, the outcoupling layer can be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the outcoupling can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material or additional layers disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer, and / or changing the material of the enhancement layer. The plurality of nanoparticles of the device can be formed of at least one of the following: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or a hierarchy of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, where the metal is selected from the group consisting of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. The plurality of nanoparticles can have additional layers disposed on them. In some embodiments, the outcoupling layer can be used to adjust the polarization of the emission. Changing the size and periodicity of the outcoupling layer can select the type of polarization that is preferentially outcoupled to air. In some embodiments, the outcoupling layer also serves as an electrode for the device.

[0254] 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 can comprise a compound as disclosed in the above compound moieties of the present disclosure.

[0255] In some embodiments, the consumer product comprises an OLED having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer can comprise a compound comprising a ligand L A of Formula I:

[0256]

[0257] wherein each of Part A and Part B is independently a monocyclic or polycyclic ring structure containing a 5- and / or 6-membered carbocyclic and / or heterocyclic ring; each of Z 1 -Z 4 is independently C or N, at least one of Z 3 and Z 4 is C; K 1 and K 2each independently is a direct bond, O, or S; X 1 - X 7 each independently is C or N, X 3 or X 7 at least one of which is N; represents a single or double bond; two wavy lines represent the point of attachment to two adjacent ring carbon atoms of moiety B; the maximum number of N atoms that can be connected to each other is two; R A , R B , and R C each represents zero, one, or up to the maximum allowed number of substitutions to the ring to which it is attached; each R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and any two adjacent R A , R B , or R C may be connected or fused to form a ring, wherein the ligand L A is coordinated to M via the two indicated dashed lines; wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and wherein the ligand L A may be connected to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

[0258] In some embodiments, the consumer product can be one of the following products: flat panel display, computer monitor, medical monitor, television, sign, light for interior or exterior illumination and / or signaling, heads-up display, fully or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, 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 or augmented reality display, vehicle, video wall comprising a plurality of displays tiled together, theater or stadium screen, phototherapy device, and sign.

[0259] 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 each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an "exciton," which is a localized electron-hole pair having an excited energy state, is formed. When the exciton relaxes, it releases energy that can be in the form of light. In some cases, the exciton can localize on an excimer or an exciplex. Non-radiative mechanisms (such as thermal relaxation), which do not generate light, can also occur. However, it is generally desired that the exciton relaxes through an electric dipole transition, which emits light.

[0260] Certain OLED materials and configurations are described in U.S. Patents 5,844,363, 6,303,238 and 5,707,745, which are incorporated herein by reference in their entirety.

[0261] Early OLEDs used emitting molecules that emitted light from a single state (“fluorescence”), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated herein by reference in its entirety. Fluorescence emission typically occurs within timeframes of less than 10 nanoseconds.

[0262] Recently, OLEDs with emitting materials that emit light from the triplet state (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, Vol. 395, pp. 151-154, 1998 (“Baldo-I”); and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Applied Physics Letters, Vol. 75, pp. 3, 4-6 (1999) (“Baldo-II”), are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in columns 5-6 of U.S. Patent No. 7,279,704, which is incorporated herein by reference.

[0263] Figure 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emission 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 blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by sequentially depositing the layers. The properties and functions of these various layers and exemplary materials are described in more detail in columns 6-10 of US 7,279,704, which is incorporated herein by reference.

[0264] More examples of each of these layers can be found. 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 transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of light emitting 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 transport layer is BPhen doped with Li in a 1:1 molar ratio, 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, incorporated by reference in their entirety, disclose examples of cathodes, including composite cathodes with a thin layer of metal (such as Mg:Ag) having an overlying transparent, conductive, sputter-deposited ITO layer. The theory and application 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 entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. Descriptions of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0265] Figure 2 An inverted OLED 200 is shown. 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 sequentially. Because the most commonly used OLED configuration has a cathode disposed over the anode, and device 200 has a cathode 215 disposed under the anode 230, device 200 can be referred to as an "inverted" OLED. Similar materials as those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 One example of how some layers can be omitted from the structure of device 100 is provided.

[0266] Figure 1 and 2The simple layered structures described herein are provided by way of non-limiting examples, and it should be understood that embodiments of this disclosure can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the various layers described in different 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 examples provided herein describe various layers as comprising a single material, it should be understood that combinations of materials, such as mixtures of host and dopant, or more generally, mixtures, can be used. Furthermore, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emitter layer 220, and can be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, regarding Figure 1 and 2 Multiple layers of the different organic materials mentioned above.

[0267] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) containing polymeric materials, as disclosed in, for example, U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. By another example, OLEDs with a single organic layer can be used. OLEDs can be stacked, for example, as described in, U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. OLED structures can be deviated from... Figure 1 and 2 The simple layered structure described herein. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the tabletop structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the recessed structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0268] Unless otherwise described, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, ink-jet (as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties), organic vapor phase deposition (OVPD) as described in U.S. Pat. No. 6,337,102 to Fogarty, et al., and deposition by organic vapor jet printing (OVJP), as described in U.S. Pat. No. 7,431,968. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably conducted in a nitrogen or inert atmospheric to minimize oxidation and other damage to the material deposited. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (as described in U.S. Pat. Nos. 6,294,398 and 6,468,819 which are incorporated by reference in their entireties), and patterning associated with

[0269] Devices fabricated in accordance with embodiments of the disclosure can further optionally include a barrier layer. One use of a barrier layer is to protect the electrodes and organic layer from the deleterious effects of exposure to moisture, vapors, and / or gases. Barrier layers can be deposited on the substrate, electrode(s), on the substrate, electrode(s) or on any other portion of the device, including the edges. A barrier layer can include a single layer or multiple layers. Barrier layers can be formed by various known chemical vapor deposition techniques and can include compositions that are in a single phase or in multiple phases. Any suitable materials or combinations of materials can be used for the barrier layer. The barrier layer can be comprised of an inorganic compound or an organic compound or both. Preferred barrier layers comprise a mixture of polymeric 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 incorporated herein by reference in their entirety. To be considered a "mixture," the aforementioned polymeric and non-polymeric materials making up the barrier layer should be deposited under the same reaction conditions and / or simultaneously deposited. The weight ratio of polymeric material to non-polymeric material can range from 95:5 to 5:95. The polymeric and non-polymeric materials can be produced from the same precursor material. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0270] Devices made in accordance with embodiments of the disclosure can be incorporated into a wide variety of electronic assembly modules (or units) that can be incorporated into a wide variety of electronic products or intermediate assemblies. Examples of the electronic products or intermediate assemblies include display screens, lighting devices (such as discrete light source devices or lighting panels), etc. that can be utilized by end- user product manufacturers. The electronic assembly modules can optionally include driving electronics and / or power supplies. Devices made in accordance with embodiments of the disclosure can be incorporated into a wide variety of consumer products that have one or more electronic assembly modules (or units) incorporated therein. A consumer product is disclosed that includes an OLED that includes a compound of the disclosure in an organic layer in the OLED. The consumer product should include any kind of product that includes one or more of one or more light sources and / or some type of visual display. Some examples of the consumer product include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and / or signaling, heads-up displays, fully transparent or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays (displays less than 2 inches in diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls that contain multiple displays tiled together, theater or stadium screens, light therapy devices, and signs. Devices made in accordance with the disclosure can be controlled using a variety of control mechanisms, including passive matrix and active matrix. It is intended that many of the devices be used in temperature ranges that are comfortable for humans, such as 18 °C to 30 °C, and more preferably at room temperature (20-25 °C), but can be used outside this temperature range (e.g., -40 °C to +80 °C).

[0271] 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.

[0272] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can employ the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0273] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

[0274] In some embodiments, the OLED further comprises a layer comprising a delayed fluorescence emitter. In some embodiments, the OLED comprises an RGB pixel arrangement or a white plus color filter pixel arrangement. 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.

[0275] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also known 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 emissive dopant can be a racemic mixture, or can be enriched in one enantiomer. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from the others). In some embodiments, when there is more than one ligand coordinated to the metal, the ligands can all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, each ligand can be different from each other. This also holds true in embodiments where a ligand coordinated to the metal can be connected to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Thus, where the coordinated ligands are connected together, in some embodiments all of the ligands can be the same, and in some other embodiments at least one of the connected ligands can be different from the other ligand(s).

[0276] In some embodiments, the compounds can be used as phosphorescence sensitizers in OLEDs where one or more layers in the OLED contain acceptors in the form of one or more fluorescent and / or delayed fluorescence emitters. In some embodiments, the compounds can be used as one component of an excited state complex to be used as a sensitizer. As a phosphorescence sensitizer, the compound must be able to transfer energy to an acceptor and the acceptor will emit energy or further transfer 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 phosphorescence 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, emission can be produced by any or all of the sensitizer, acceptor, and final emitter.

[0277] According to another aspect, there is also disclosed a formulation comprising a compound described herein.

[0278] 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 an emissive layer and the compounds can be emissive dopants in some embodiments, while the compounds can be non-emissive dopants in other embodiments.

[0279] In yet another aspect of the application, a formulation comprising a novel compound disclosed herein is described. The formulation can include one or more components disclosed herein selected from the group consisting of a solvent, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material.

[0280] The present disclosure encompasses any chemical structure comprising a novel compound of the present disclosure or a monovalent or multivalent variant thereof. In other words, the compound of the present application or a monovalent or multivalent variant thereof 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, “monovalent variant of a compound” refers to a moiety that is identical to the compound but for one hydrogen having been removed and replaced with a bond to the rest of the chemical structure. As used herein, “multivalent variant of a compound” refers to a moiety that is identical to the compound but for more than one hydrogen having been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecules, the compound of the present application can also be incorporated into a supramolecular complex without a covalent bond.

[0281] D. Combinations of the compounds of the present disclosure with other materials

[0282] Materials described herein as useful for particular layers in an organic light emitting device can be used in combination with a wide variety of other materials present in devices. 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 can be present. The materials described or referenced below are non-limiting examples supplied to enable practitioners to practice the methods disclosed herein and are in no way intended to limit the scope of materials that can be used in conjunction with the compounds disclosed herein.

[0283] a) Conductive dopants:

[0284] Charge transport layers can be doped with conductive dopants to substantially alter their charge carrier density, which in turn, will alter their conductivity. The conductivity is increased by the creation of charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of a semiconductor can also be achieved. Hole transport layers can be doped with p-type conductive dopants, and n-type conductive dopants are used in electron transport layers.

[0285] Non-limiting examples of conductive dopants that can be used in combination with the materials disclosed herein for use in OLEDs are exemplified below along with references that disclose those materials: EP 0 161 749 3, EP 0 196 813 1, EP 2 020 694, EP 2 684 932, US 2005 0139810, US 2007 0160905, US 2009 0177167, US 2010 288362, WO 06081780, WO 2009 003455, WO 2009 008277, WO 2009 011327, WO 2014 009310, US 2007 252140, US 2015 060804, US 2015 0123047, and US 2012 146012.

[0286]

[0287]

[0288] b) HIL / HTL:

[0289] The hole injection / transport material used in the present disclosure is not particularly limited, and any compound can be used as long as the compound is generally used as a hole injection / transport material. Examples of the material include, but are not limited to: phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; fluorocarbon-containing polymers; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO xp-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylhexacarbonitrile; metal complexes; and crosslinkable compounds.

[0290] Examples of aromatic amine derivatives used for HIL or HTL include (but are not limited to) the following general structures:

[0291]

[0292] Ar 1 To Ar 9 Each of these is selected from the group consisting of, for example, aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, Perylene and azurite; the group consisting of, for example, aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benziisoxazole, benzothiazole, quinoline, isoquinoline, zoline, quinazoline Quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenepyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. Each Ar may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0293] In one aspect, Ar 1 To Ar 9 Choose independently from the following groups:

[0294]

[0295] Where k is an integer from 1 to 20; X 101 To X 108 It is C (including CH) or N; Z 101 It is NAr 1, O or S; Ar 1 having the same groups defined above.

[0296] Examples of metal complexes used in the HIL or HTL include, but are not limited to, the following general formula:

[0297]

[0298] where Met is a metal having an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 are independently selected from C, N, O, P and S; L 101 is an ancillary ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k' + k" is the maximum number of ligands that can be attached to the metal.

[0299] In one aspect, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another aspect, (Y 101 -Y 102 ) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os and Zn. In another aspect, the metal complex has a minimum oxidation potential in solution of less than about 0.6 V vs. Fc + / Fc coupling.

[0300] Non-limiting examples of HIL and HTL materials that can be combined with the materials disclosed herein for use in OLEDs are illustrated below along with references disclosing those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, 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.

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308] c) EBL:

[0309] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer in a device can result in a device that has a generally higher efficiency and / or a longer lifetime compared to a similar device lacking the blocking layer. Further, the blocking layer can be used to confine the emission to a desired area of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a 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 a 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 used in one of the hosts described below.

[0310] d) Host:

[0311] The light-emitting layer of the organic EL device of the present disclosure preferably contains at least a metal complex as a light-emitting material, and can contain a host material that uses a metal complex as a dopant material. Examples of the host material are 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 with any dopant as long as the triplet criterion is satisfied.

[0312] Examples of the metal complex used as the host preferably have the following general formula:

[0313]

[0314] wherein Met is a metal; (Y 103 -Y 104) is a bidentate ligand, Y 103 and Y 104 are independently selected from C, N, O, P, and S; L 101 is 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.

[0315] In one aspect, the metal complex is:

[0316]

[0317] where (O-N) is a bidentate ligand having a metal coordinated to O and N atoms.

[0318] In another aspect, Met is selected from Ir and Pt. In another aspect, (Y 103 -Y 104 ) is a carbene ligand.

[0319] In one aspect, the host compound contains at least one from the following groups selected from the group consisting of aromatic hydrocarbon cyclic compounds consisting of, for example, benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, lewis, phenanthrene, fluorene, pyrene, pyrene, and azulene; aromatic heterocyclic compounds consisting of, for example, dibenzothiophene, dibenzofurane, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolo-dipyridal, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indooxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, phenoxazine, benzofuropyridine, furopyridal, benzothienopyridine, thienopyridal, benzoselenophenopyridine, and selenophenopyridal; and a group consisting of 2 to 10 cyclic structural units that are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic ring groups and are bonded to each other directly or via at least one of oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units, and aliphatic ring groups. Each option in each group can be unsubstituted or can be substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0320] In one aspect, the host compound contains at least one of the following groups in the molecule:

[0321]

[0322]

[0323] wherein R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has similar definition as Ar mentioned above. k is an integer from 0 to 20 or 1 to 20. X 101 is independently selected from C (including CH) or N. Z 108 is independently selected from C (including CH) or N. Z 101 is independently selected from C (including CH) or N. Z 102 is independently selected from NR 101 , O, or S.

[0324] Non-limiting examples of host materials that can be combined with the materials disclosed herein for use in OLEDs are exemplified below along with references disclosing those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803,

[0325]

[0326]

[0327]

[0328]

[0329]

[0330] e) Other emitters:

[0331] One or more other emitter dopants can be used in conjunction with the compounds of the present application. Examples of other emitter dopants are not particularly limited, and any compound can be used as long as the compound is generally used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0332] Non-limiting examples of emitter materials that can be combined with the materials disclosed herein for use in OLEDs are illustrated below along with references disclosing those 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.

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339] f) HBL:

[0340] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the emission layer. The presence of such a blocking layer in a device can result in substantially higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. Furthermore, the blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or a higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the HBL interface.

[0341] In one aspect, the compounds used in the HBL contain the same molecule or the same functional group as used in the hosts described above.

[0342] In another aspect, the compounds used in the HBL contain at least one of the following groups in the molecule:

[0343] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0344] g) ETL:

[0345] An electron transport layer (ETL) can include a material capable of transporting electrons. The electron transport layer can be intrinsic (undoped) or doped. Doping can be used to enhance the conductivity. Examples of ETL materials are not particularly limited and can use any metal complex or organic compound as long as it is typically used to transport electrons.

[0346] In one aspect, the compounds used in the ETL contain at least one of the following groups in the molecule:

[0347]

[0348] where R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thioether, sulfido, sulfinyl, sulfonyl, phosphino, and combinations thereof, which when an aryl or heteroaryl group, has analogous definitions to that of Ar. Ar 1To Ar 3 It has a similar definition to Ar mentioned above. k is an integer from 1 to 20. X 101 To X 108 Selected from C (including CH) or N.

[0349] In another aspect, the metal complexes used in ETL contain (but are not limited to) the following general formula:

[0350]

[0351] Wherein (ON) or (NN) are bidentate ligands of metals that coordinate with atoms O, N or N, N; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bonded to the metal.

[0352] Non-limiting examples of ETL materials that can be used in OLEDs with the material combinations disclosed herein are illustrated below, along with references to those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US20 10108990, US2011156017, US2011210320, US2012193612, US2012214993, US201401 4925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO20 07111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO201110 5373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

[0353]

[0354]

[0355]

[0356] h) Charge generation layer (CGL)

[0357] In a tandem or stacked OLED, the CGL plays an essential role in performance, which consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. The electrons and holes consumed in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the ambipolar current gradually reaches a steady state. Typical CGL materials include n and p conductivity dopants used in transport layers.

[0358] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. The minimum amount of hydrogen in the compound that is deuterated is selected from the group consisting of 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. Thus, any specifically listed substituent, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in its non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes, such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, and the like, can also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0359] It should be 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 deviating from the spirit of the invention. The present invention is therefore to be considered in all respects as illustrative and not restrictive, as other changes can become apparent to those skilled in the art, and can be made without departing from the scope and spirit of the invention. The various theories are not intended to be limiting.

[0360] E. Experimental Section

[0361] Synthesis of representative compounds

[0362]

[0363]

[0364] Synthesis of N-(2-aminophenyl)-5-chloro-2-iodobenzamide.

[0365]

[0366] To a solution of 5-chloro-2-iodobenzoic acid (21.8 g, 77 mmol) and triethylamine (23.43 g, 232 mmol) in DMF (150 ml) was added HBTU (43.9 g, 116 mmol). The resulting mixture was stirred at room temperature (RT) for 15 minutes. Then phen-1,2-diamine (16.69 g, 154 mmol) was added. The reaction mixture was stirred at room temperature for two days. The reaction mixture was poured into water (600 mL). The fragmented solid was collected by filtration and washed with water (150 mL). Then dried in air to give the crude product N-(2-aminophenyl)-5-chloro-2-iodobenzamide as a brown solid (29.5 g, 103% yield). The product was used without further purification.

[0367] Synthesis of 2-(5-chloro-2-iodophenyl)-1H-benzo[d]imidazole.

[0368]

[0369] A suspension of N-(2-aminophenyl)-5-chloro-2-iodobenzamide (13.0 g, 34.9 mmol) in acetic acid (161 ml, 2791 mmol) was heated at 80 °C overnight. A clear brown solution was obtained, LCMS showed the reaction was complete. After cooling, the reaction mixture was poured into water (500 mL). The precipitate was collected by filtration and washed with water (150 mL). Then dried in air to give 2-(5-chloro-2-iodophenyl)-1H-benzo[d]imidazole as an off-white solid (11.4 g, 92%).

[0370] Synthesis of 2-(5-chloro-2-((triethylsilyl)ethynyl)phenyl)-1H-benzo[d]imidazole.

[0371]

[0372] A suspension of 2-(5-chloro-2-iodophenyl)-1H-benzo[d]imidazole (6.0 g, 16.92 mmol), triethyl(ethynyl)silane (7.12 g, 50.8 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.594 g, 0.846 mmol), copper(I) iodide (0.161 g, 0.846 mmol) and triethylamine (23.59 ml, 169 mmol) in dioxane (100 ml) was degassed by nitrogen for 5 minutes. It was then heated at 90°C overnight under nitrogen. The reaction was cooled to room temperature. Silica gel (89 g) was added and the whole mixture was sonicated for 10 minutes. The solvent was then removed. The crude product was then purified by Biotage Isolera flash chromatography using a SILICYCLE SiliaSep 330 g cartridge connected to a 220 g cartridge and eluted with 0% to 3% THF / DCM to give the desired product 2-(5-chloro-2-((triethylsilyl)ethynyl)phenyl)-1H- benzo[d]imidazole (7.27 g, 59% yield) as a brown wax.

[0373] Synthesis of 2-chlorobenzo[4,5]imidazo[2,1-a]isoquinoline.

[0374]

[0375] A suspension of 2-(5-chloro-2-((triethylsilyl)ethynyl)phenyl)-1H-benzo[d]imidazole (15.2 g, 41.4 mmol), potassium carbonate (17.17 g, 124 mmol) in THF (80 ml) and MeOH (80 ml) was stirred at 45°C over the weekend. After cooling, silica gel (45 g) was added and the solvent was removed. The crude product was purified by Biotage Isolera flash chromatography using a SILICYCLE SiliaSep (220 g connected together with 330 g) cartridge and eluted with 0% to 10% THF / DCM to give the desired product 2-chlorobenzo[4,5]imidazo[2,1-a]isoquinoline (7.8 g, 75% yield) as a yellow solid (product appears at 9% THF; earlier fractions are pure and later fractions are mixed with impurity peaks).

[0376] Synthesis of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[4,5]imidazo[2,1- a]isoquinoline.

[0377]

[0378] A suspension of tricyclohexylphosphine (2.308 g, 8.23 mmol), 2-chlorobenzo[4,5]imidazo[2,1- a]isoquinoline (16 g, 63.3 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (24.12 g, 95 mmol), potassium acetate (18.64 g, 190 mmol), and Pd2(dba)3(2.90 g, 3.17 mmol) in dioxane (422 ml) was bubbled with nitrogen for 20 minutes. The reaction mixture was then heated at 110 °C. The reaction mixture was allowed to cool to room temperature and the solvent was removed. The resulting residue was re-dissolved in EtOAc and then filtered (100 g of celite). The solvent was removed under vacuum to give an orange thick syrup. To this material was added MeCN (50 mL) to give 4.62 g of bright yellow solid after filtration. The mother liquor was dried under vacuum to give an orange thick oil (18 g).

[0379] Synthesis of 2-(4,5-bis(methyl-d3)pyridin-2-yl)benzo[4,5]imidazo[2,1- a]isoquinoline

[0380]

[0381] In an oven-dried 150 mL round bottom flask, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzo[4,5]imidazo[2,1-a]isoquinoline (4.6 g, 13.36 mmol), 2-bromo-4,5-bis(methyl-d3)pyridine (2.57 g, 13.36 mmol), and potassium carbonate (3.69 g, 26.7 mmol) were dissolved in 75 mL of a mixture of DME and 10 mL of water to give a colorless solution. Pd(PPh3)4(0.463 g, 0.401 mmol) was added in one portion, the reaction mixture was degassed and heated to reflux under nitrogen for 12 hours. The reaction mixture was then cooled, diluted with ethyl acetate and washed with water. The organic solution was evaporated and the residue was column chromatographed on silica gel with DCM / ethyl acetate 4 / 1 elution to give 2-(4,5-bis(methyl-d3)pyridin-2-yl)benzo[4,5]imidazo[2,1-a]isoquinoline as a white solid (2.5 g, 7.59 mmol, 56.8% yield).

[0382] Synthesis of representative compound 1

[0383]

[0384] Iridium complex triflate (2 g) and 2-(4,5-bis(methyl-d3)pyridin-2-yl)benzo[4,5]imidazo[2,1- a]isoquinoline (1.3 g, 1.7 eq.) were suspended in 50 mL 2-ethoxyethanol, the reaction mixture was degassed and heated to 70 °C for 56 h. The reaction mixture was cooled, diluted with water and extracted with ethyl acetate. The organic solution was evaporated and the residue was column chromatographed on silica gel column eluting with heptane / ethyl acetate (9 / 1 to 2 / 1) gradient mixture to give compound 1 (1.0 g, 44%) as a yellow solid, m / z 973.

[0385] Figure 3 Compound 1 exhibits several emission spectra under different conditions. Compound 1 exhibits an emission energy of 502 nm in 2-methylTHF at 77 K, and an emission energy of 513 nm in 2-methylTHF at room temperature, and an emission energy of 515 nm in PMMA. This means that representative compound 1 is suitable for green OLED applications. Compound 1 also has an extremely high quantum yield (73% PLQY). In addition, compound 1 exhibits a bi-exponential excited state decay of 8.2 ps (77%) + 14 ps (23%), indicating that more than one excited state contributes to the emission. The weighted average of the excited state lifetime is 9.5 ps, which indicates that it has a reasonable transient. All of these parameters support that the present example is an excellent emitter for green OLED applications.

Claims

1. A compound having the formula M(L A ) p (L B ) q (L C ) r wherein p is 1 or 2; q is 1 or 2; r is 0; and p + q + r is the oxidation state of the metal M, wherein: L A is wherein: R A and each of R B represents zero, one or up to the maximum allowed number of substitutions of the ring to which it is attached; each R A and R B independently are hydrogen or a substituent selected from the group consisting of deuterium, fluoro, C 1-15 alkyl, C 3-12 cycloalkyl, and combinations thereof; and L B is wherein: Y 1 to Y 8 each independently is carbon; each R a and R b independently represent zero, one or up to the maximum allowed number of substitutions of the ring to which they are attached; R a and each of R b is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, C 1-15 alkyl, C 3-12 cycloalkyl, and combinations thereof; and wherein the ligand L A coordinated via the two indicated dashed lines to M; and wherein M is Ir.

2. The compound of claim 1, wherein L A is L Ai'-N'-m wherein each L Ai'-N' is defined as shown below: and L Ai'-N'-m substituents J 1 , J 2 , R a1 , R a2 , R b1 and R b2 are defined as follows for each m: wherein in the definition of the substituents R a1 , R a2 , R b1 and R b2 A = Me, B = CD3, and L = H.

3. The compound of claim 1, wherein the compound has a formula selected from the group consisting of: Ir(L A )(L B )2 and Ir(L A )2(L B ).

4. The compound of claim 2, wherein the compound has a formula selected from the group consisting of: Ir(L A )(L B )2 and Ir(L A )2(L B ); when the compound has the formula Ir(L Ai'-N'-m )(L Bk )2 or Ir(L Ai'-N'-m )2(L Bk ), each L Bk has the structure defined below:

5. A compound selected from the group consisting of:

6. An organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound according to any one of claims 1-5.

7. The OLED of claim 6, wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dithiophene, dithiophene, dithiophene, 5,9-dioxa-13b-bora-naphthacene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dithiophene, aza-dithiophene, aza-dithiophene, and aza-(5,9-dioxa-13b-bora-naphthacene).

8. The OLED of claim 7, wherein the host is selected from the group consisting of: and combinations thereof.

9. A consumer product comprising an organic light emitting device, the organic light emitting device comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound according to any one of claims 1-5.

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