Organic electroluminescent materials and devices

Abstract

The invention relates to organic electroluminescent materials and devices. An OLED is provided having an anode, a cathode, and an organic emission layer disposed between the anode and the cathode. The emission layer includes a first body; and a first emitter; wherein the first emitter is selected from the group consisting of (L1-L2) nIr (LA) 3-n and (LB) nIr (L3-L4) 3-n; wherein (L1-L2) nIr (LA) 3-n is # imgabs 0 # and (LB) nIr (L3-L4) 3-n is # imgabs 1 #

Description

[0001] This application is a divisional application of the invention patent application with application date of March 31, 2021, application number 202110347105.4, and name “Organic Electroluminescent Materials and Devices”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 63 / 002,564, filed on March 31, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0004] The present disclosure generally relates 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 Art

[0005] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly popular. Many of the materials used to manufacture the devices are relatively inexpensive, so organic optoelectronic devices have the potential to offer cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) can make them more suitable for specific applications, such as manufacturing on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

[0006] OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly attractive technology for applications such as flat panel displays, lighting, and backlighting.

[0007] One application of phosphorescent emitting molecules is full-color displays. Industry standards for such displays require pixels that are suitable for emitting specific colors (called "saturated" colors). Specifically, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technology can also be used for OLEDs. White OLEDs can be single-emission layer (EML) devices or stacked structures. Color can be measured using CIE coordinates, which are well known in the art. Summary of the Invention

[0008] In one aspect, the present disclosure provides an OLED comprising: an anode; a cathode; and an organic emission layer disposed between the anode and the cathode. The emission layer comprises: a first host; and a first emitter; wherein the first emitter is selected from (L 1-L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n Compounds of the group consisting of;

[0009] Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L 3 -L 4 ) 3-n for

[0010] Among them: Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; each L 1 -L 2 and L 3 -L 4 independently represents an anionic bidentate ligand; n is 1 or 2; each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 is independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; each R S11 、R S12 and R S13 R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; S11 、R S12 and R S13 At least one of the following is selected from the group consisting of: deuterium, silyl, C1 to C3 alkyl, substituted or unsubstituted cycloalkyl, and branched substituted or unsubstituted alkyl with branching occurring at the benzyl position; and wherein the first host comprises at least one donor group G D , and at least one acceptor group GA .

[0011] In another aspect, the present disclosure provides a formulation of the first emitter compound of the present disclosure.

[0012] In yet another aspect, the present disclosure provides consumer products comprising the disclosed OLEDs. BRIEF DESCRIPTION OF THE 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 demonstrated. DETAILED DESCRIPTION

[0015] A. Terminology

[0016] Unless otherwise specified, the following terms used herein are defined as follows:

[0017] As used herein, the term "organic" includes polymeric materials and small molecule organic materials that can be used to make organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. In some cases, small molecules may include repeating units. For example, the use of long-chain alkyl groups as substituents does not remove a molecule from the "small molecule" category. Small molecules can also be incorporated into polymers, for example as side groups on the polymer backbone or as part of the backbone. Small molecules can also serve as the core part of a dendrimer, which consists of a series of chemical shells built on the core part. The core part of a dendrimer can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules", and all dendrimers currently used in the field of OLEDs are considered to be small molecules.

[0018] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed above" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed above" the anode even if various organic layers are present between the cathode and the anode.

[0019] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0020] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand may be referred to as "photosensitive." When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand may be referred to as "ancillary," but the ancillary ligand may modify the properties of the photosensitive ligand.

[0021] As used herein, and as will be generally understood by one skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potential (IP) is measured as negative energy relative to the vacuum energy level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (a less negative EA). On a conventional energy level diagram with the vacuum energy level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears closer to the top of this diagram than a "lower" HOMO or LUMO energy level.

[0022] As used herein, and as will generally be understood by those skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are typically measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being further away from the vacuum level in a downward direction. Therefore, the definitions of HOMO and LUMO energy levels follow different rules than those for work functions.

[0023] The terms "halo," "halogen," and "halo" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0024] The term "acyl" refers to a substituted carbonyl (C(O)-R s ).

[0025] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0026] The term "ether" refers to -OR s group.

[0027] The terms "thio" or "thioether" are used interchangeably and refer to -SR s group.

[0028] The term "sulfinyl" refers to -S(O)-R s group.

[0029] The term "sulfonyl" refers to -SO2-R s group.

[0030] The term "phosphino" refers to -P(R s )3 groups, wherein each R s Can be the same or different.

[0031] The term "silyl" refers to -Si(R s )3 groups, wherein each R s Can be the same or different.

[0032] The term "boryl" refers to -B(R s )2 group or its Lewis adduct -B(R s )3 groups, wherein R s Can be the same or different.

[0033] In each of the above, R s and R is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. s Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0034] The term "alkyl" refers to and includes straight-chain and branched alkyl groups. Preferred alkyl groups are those 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. In addition, the alkyl group may be optionally substituted.

[0035] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are those 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. In addition, the cycloalkyl group may be optionally substituted.

[0036] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably O, S or N. In addition, the heteroalkyl or heterocycloalkyl group may be optionally substituted.

[0037] The term "alkenyl" refers to and includes straight and branched alkenyl groups. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" 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. In addition, alkenyl, cycloalkenyl or heteroalkenyl groups may be optionally substituted.

[0038] The term "alkynyl" refers to and includes straight and branched chain alkynyl groups. An alkynyl group is essentially an alkyl group that includes at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing two to fifteen carbon atoms. In addition, an alkynyl group may be optionally substituted.

[0039] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, an aralkyl group may be optionally substituted.

[0040] 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 can be 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 morpholinyl, piperidinyl, pyrrolidinyl, and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. In addition, the heterocyclic group can be optionally substituted.

[0041] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbon atoms 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 can be cycloalkyl, cycloalkenyl, aryl, heterocycle 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. Especially preferred are aryl groups with six carbon atoms, ten carbon atoms or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted.

[0042] The term "heteroaryl" refers to and encompasses 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 rings may have from one to six heteroatoms. Heteropolycyclic ring systems may have two or more rings in which two atoms are common to two adjacent rings (the rings are "fused"), wherein at least one of the rings is a heteroaryl group, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl groups. Heteropolycyclic aromatic ring systems may have from one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, and more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazole In some embodiments, the heteroaryl group may be substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine and aza analogs thereof. In some embodiments, the heteroaryl group may be substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine and aza analogs thereof. In some embodiments, the heteroaryl group may be substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine and aza analogs thereof. In some embodiments, the heteroaryl group may be substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine and aza analogs thereof. In some embodiments, the heteroaryl group may be substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine and aza analogs thereof.

[0043] 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 aza analogs are of particular interest.

[0044] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl are independently unsubstituted or substituted with one or more typical substituents.

[0045] In many cases, the general substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

[0046] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, boryl, and combinations thereof.

[0047] In some cases, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silanyl, boryl, aryl, heteroaryl, thio, and combinations thereof.

[0048] In other cases, the most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0049] The terms "substituted" and "substituted" refer to substituents other than H being bonded to the relevant position, such as carbon or nitrogen. For example, when R 1 When it represents a single substitution, one R 1 must not be H (i.e., substituted). Similarly, when R 1 When it represents disubstituted, the two R 1 must not be H. Similarly, when R 1 When it represents zero or no substitution, R 1 For example, it can be hydrogen with available valences for the ring atoms, such as the carbon atoms in benzene and the nitrogen atoms in pyrrole, or simply none for ring atoms with fully saturated valences, such as the nitrogen atoms in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences among the ring atoms.

[0050] As used herein, "combinations thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that a person of ordinary skill in the art can conceive from the applicable list. For example, alkyl and deuterium can combine to form partially or fully deuterated alkyl; halogen and alkyl can combine to form a haloalkyl substituent; and halogen, alkyl, and aryl can combine to form a haloaralkyl substituent. In one example, the term substituted includes a combination of two to four of the listed groups. In another example, the term substituted includes a combination of two to three groups. In yet another example, the term substituted includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations that include up to forty atoms that are not hydrogen or deuterium, or combinations that include 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.

[0051] The "aza" designation in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the CH groups in the corresponding aromatic ring can be replaced by a nitrogen atom, for example, and without limitation, azatriphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the term as set forth herein.

[0052] As used herein, " deuterium " refers to an isotope of hydrogen. Deuterated compounds can be easily 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. US2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. With further reference 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) describe the deuteration of methylene hydrogen in benzylamine and an effective way to replace aromatic ring hydrogen with deuterium.

[0053] 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 is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0054] In some cases, a pair of adjacent substituents may be optionally joined or fused to form a ring. Preferred rings are five-, six-, or seven-membered carbocyclic or heterocyclic rings, including those in which a portion of the ring formed by the pair of substituents is saturated and a portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two substituents involved may be immediately adjacent to each other on the same ring, or on two adjacent rings with the two closest available substitutable positions (such as the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene), as long as they can form a stable fused ring system.

[0055] B. Compounds of the Disclosure

[0056] Disclosed are emitter compounds selected from the group consisting of: (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n ;

[0057] Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L 3 -L 4 ) 3-n for

[0058] Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring;

[0059] Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands;

[0060] Where n is 1 or 2;

[0061] Each R S1 、R S2 、R S3 、R S4 、R S5 、R S6independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof;

[0062] Each R S11 、R S12 and R S13 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;

[0063] where R S11 、R S12 and R S13 At least one of the following is selected from the group consisting of: deuterium, silyl, C1 to C3 alkyl, substituted or unsubstituted cycloalkyl, and branched substituted or unsubstituted alkyl with branching occurring at the benzyl position; and

[0064] wherein the first host comprises at least one donor group G D , and at least one acceptor group G A .

[0065] C. OLEDs and Devices of the Present Disclosure

[0066] In another aspect, the present disclosure also provides an OLED device comprising a first organic layer containing a compound as disclosed in the above compound section of the present disclosure.

[0067] In some embodiments, the OLED comprises: an anode; a cathode; and an organic emission layer disposed between the anode and the cathode. The emission layer comprises: a first host; and a first emitter; wherein the first emitter is selected from (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n the groups formed;

[0068] Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L3 -L 4 ) 3-n for

[0069] Among them: Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; each L 1 -L 2 and L 3 -L 4 independently represents an anionic bidentate ligand; n is 1 or 2; each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 is independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; each R S11 、R S12 and R S13 R is independently hydrogen or a substituent selected from the group consisting of the general substituents described above; S11 、R S12 and R S13 At least one of is selected from the group consisting of: deuterium, silyl, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and combinations thereof; wherein R S1 、R S2 、R S3 、R S4 、R S5 、R S6 、R S11 、R S12 and R S13 Any two substituents of can be joined or fused to form a ring; and the first main body comprises at least one donor group G D , and at least one acceptor group G A Therefore, the ligand L B Can

[0070] In some embodiments of OLEDs, R S11 、R S12 and R S13 At least one of the following is selected from the group consisting of deuterium, a silyl group, a C1 to C3 alkyl group, a substituted or unsubstituted cycloalkyl group, and a branched substituted or unsubstituted alkyl group in which branching occurs at the benzyl position.

[0071] In some embodiments of OLEDs, each R S11 、RS12 and R S13 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, boryl, and combinations thereof.

[0072] In some embodiments of the OLED, n is 2.

[0073] In some embodiments of OLEDs, wherein the first emitter has the formula (L B ) n Ir(L 3 -L 4 ) 3-n , the first emitter is selected from the group consisting of:

[0074]

[0075] Wherein X' is selected from the group consisting of: BR e BR e R f 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 ; where each R e 、R f and R S14 are independently hydrogen or a general substituent as described above; and wherein R e 、R f and R S14 Any two substituents of may be joined or fused to form a ring.

[0076] In some embodiments of OLEDs, the first emitter is a luminescent material having the formula (L 1 -L 2 ) n Ir(L A ) 3-n Compound A, whose structure is

[0077] In some embodiments of OLEDs, wherein the first emitter is compound A, the ligand (L 1 -L 2 ) is selected from the group consisting of:

[0078]

[0079] Where: Y 1 To Y 10 Each independently selected from the group consisting of carbon and nitrogen; Y' is selected from the group consisting of: BR e BR e R f 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 ; R e and R f are optionally fused or joined to form a ring; R a and R b Each independently represents zero substitution, monosubstitution or up to the maximum allowed substitution on its associated ring; R a 、R b 、R e and R f Each of R is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and R a and R b Two adjacent substituents of are optionally fused or joined to form a ring or to form a multidentate ligand.

[0080] In some embodiments of OLEDs, wherein the first emitter is compound A, the ligand (L 1 -L 2 ) is selected from the group consisting of:

[0081]

[0082]

[0083]

[0084] Where: R a ' and R b ' Each independently represents zero substitution, monosubstitution or up to the maximum allowed substitution on its associated ring; R a ' and R b ' are each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; and R a ' and R b Two adjacent substituents of ' are optionally fused or joined to form a ring or to form a multidentate ligand.

[0085] In some embodiments of OLEDs, wherein the first emitter is compound A, the ligand (L 1-L 2 ) is selected from the group consisting of:

[0086] L based on structure 1 1 -L 2 -1-i: L based on structure 2 1 -L 2 -2-i: L based on structure 3 1 -L 2 -3-i: L based on structure 4 1 -L 2 -4-i: L based on structure 5 1 -L 2 -5-i: L based on structure 6 1 -L 2 -6-i: L based on structure 7 1 -L 2 -7-i: L based on structure 8 1 -L 2 -8-i: L based on structure 9 1 -L 2 -9-i: L based on structure 10 1 -L 2 -10-i: L based on structure 11 1 -L 2 -11-i: L based on structure 12 1 -L 2 -12-i: Based on structure 13 L 1 -L 2 -13-i: L based on structure 14 1 -L 2 -14-i: and L based on structure 15 1 -L 2 -15-i: L based on structure 16 1 -L 2 -16-i: L based on structure 17 1 -L 2 -17-i: Where i is an integer from 1 to 810, and for each i, RE and G are defined as follows:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] where R 1 to R 45 Has the following structure:

[0094] and

[0095] Among them G 1 to G 18 Has the following structure:

[0096] In some embodiments of OLEDs, where the first emitter is compound A, each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 independently selected from the group consisting of 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, cyclopentyl, cyclohexyl, phenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-diisopropylphenyl, and combinations thereof.

[0097] In some embodiments of OLEDs, wherein the first emitter is compound A, L A The ligand is selected from the group consisting of:

[0098] L based on structure A1 A1 -k: L based on structure A2 A2 -k: L based on structure A3 A3 -k: L based on structure A4 A4-k: L based on structure A5 A5 -k: and L based on structure A6 A6 -k: Where k is an integer from 1 to 600, and for each k, R D 、R F and R G The definition is as follows:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] where R D1 to R D23 Has the following structure:

[0105]

[0106]

[0107] In some embodiments of OLEDs, the first emitter is selected from the group consisting of: based on the general formula (L 1 -L 2 -mi)2Ir(L An -k)(L 1 -L 2 -1-1)2Ir(L A1 -1) to (L 1 -L 2 -17-810)2Ir(L A6 -600), wherein m is an integer from 1 to 17, i is an integer from 1 to 810, n is an integer from 1 to 6, and k is an integer from 1 to 600.

[0108] In some embodiments of OLEDs, wherein the first emitter is compound A, the first emitter may be selected from the group consisting of:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] In some embodiments of OLEDs, wherein the first emitter is Compound B, Compound C, Compound D, or Compound E, R S11 、R S12 and R S13 At least one of is selected from the group consisting of:

[0117]

[0118]

[0119] In some embodiments of OLEDs, the first emitters are all of formula (L B ) n Ir(L 3 -L 4 ) 3-n Compound B, Compound C, Compound D or Compound E, the first emitter is selected from the group consisting of:

[0120]

[0121]

[0122] When there is more than one R S11 or R S13 When each R S11 and R S13 Can be the same or different.

[0123] In some embodiments of OLEDs, the first emitters are all of formula (L B ) n Ir(L 3 -L 4 ) 3-n Compound B, Compound C, Compound D or Compound E, Ligand L B Select from the group consisting of:

[0124] L based on structure B1 B1 -h: L based on structure B2 B2 -h:

[0125] L based on structure B3 B3-h: L based on structure B4 B4 -h:

[0126] L based on structure B5 B5 -h:

[0127] Where h is an integer from 1 to 1170, and for each h, R H and G are defined as follows:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] where R H1 to R H65 Has the following structure:

[0136]

[0137] Among them G 1 to G 18 Has the following structure:

[0138] In some embodiments of OLEDs, the first emitters are all of formula (L B ) n Ir(L 3 -L 4 ) 3-n Compound B, Compound C, Compound D or Compound E, ligand (L 3 -L 4 ) is selected from the group consisting of:

[0139] Based on the formula The structure of L Cj-I ;and

[0140] Based on the formula The structure of L Cj-II, where j is an integer from 1 to 1416, where for L Cj-I and L Cj-II Each L in Cj , R 201 and R 202 Each is independently defined as follows:

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] where R D1 to R D246 Has the following structure:

[0150]

[0151]

[0152]

[0153]

[0154] In some embodiments of OLEDs, the first emitters are all of formula (L B ) n Ir(L 3 -L 4 ) 3-n Compound B, Compound C, Compound D or Compound E, ligand (L 3 -L 4 ) is selected from the corresponding R 201 and R 202 Those L defined as one of the following structures Cj-I and L Cj-II Groups composed of: R D1 、R D3 、R D4 、R D5 、R D9 、R D10 、RD17 、R D18 、R D20 、R D22 、R D37 、R D40 、R D41 、R D42 、R D43 、R D48 、R D49 、R D50 、R D54 、R D55 、R D58 、R D59 、R D78 、R D79 、R D81 、R D87 、R D88 、R D89 、R D93 、R D116 、R D117 、R D118 、R D119 、R D120 、R D133 、R D134 、R D135 、R D136 、R D143 、R D144 、R D145 、R D146 、R D147 、R D149 、R D151 、R D154 、R D155 、R D156 、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 .

[0155] In some embodiments of OLEDs, the first emitters are all of formula (L B )n Ir(L 3 -L 4 ) 3-n Compound B, Compound C, Compound D or Compound E, ligand (L 3 -L 4 ) is selected from the group consisting of:

[0156]

[0157]

[0158] In some embodiments of OLEDs, the first emitter is selected from the group consisting of: based on the general formula (L Bp -h)2Ir(L Cj-I ) of (L B1 -1)2Ir(L C1-I ) to (L B4 -1170)2Ir(L C1416-I ), and based on the general formula (L Bp -h)2Ir(L Cj-II ) of (L B1 -1)2Ir(L C1-II ) to (L B4 -1170)2Ir(L C1416-II ); wherein p is an integer from 1 to 4, and h is an integer from 1 to 1170.

[0159] In some embodiments of the OLED, wherein the first emitter is Compound B, Compound C, Compound D, or Compound E, the first emitter is selected from the group consisting of:

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] In some embodiments of the OLED, wherein the first emitter is selected from the group consisting of (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) nIr(L 3 -L 4 ) 3-n The first entity has the formula G D -LG A , wherein L is a direct bond or an organic linking group. In some embodiments, at least one donor group G D Each of the amines independently comprises at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.

[0167] In some embodiments of the OLEDs of the present disclosure, at least one donor group G D Each of the amines independently comprises at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.

[0168] In some embodiments of the OLED, wherein the first host has formula G D -LG A and L is a direct bond or an organic linking group, at least one acceptor group G A Each of the independently comprises at least one moiety selected from the group consisting of a nitrile, an isonitrile, a fluoride, a six-membered aromatic ring having at least one nitrogen, and a five-membered aromatic ring having at least two heteroatoms.

[0169] In some embodiments of the disclosed OLEDs, at least one acceptor group G A Each of the independently comprises at least one moiety selected from the group consisting of a nitrile, an isonitrile, a fluoride, a six-membered aromatic ring having at least one nitrogen, and a five-membered aromatic ring having at least two heteroatoms.

[0170] In some embodiments of the OLEDs of the present disclosure, at least one donor group G D Each of which independently comprises at least one portion selected from the group consisting of:

[0171]

[0172] wherein X is selected from the group consisting of: O, S, Se, and NR; and wherein each R is independently selected from (i) G A , (ii) with G A an organic linking group, and (iii) a terminal group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an aryl group, a heteroaryl group, and combinations thereof.

[0173] In some embodiments of the disclosed OLEDs, at least one acceptor group GA Each of which independently comprises at least one moiety selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole.

[0174] In some embodiments of the OLED of the present disclosure, the first host comprises at least two donor groups G D ; and at least two acceptor groups G A ; wherein each donor group G D and receptor group G A Can be the same or different; any pair of donor groups G D By at least one acceptor group G A Separation; and any pair of receptor groups G A At least one donor group G D In some embodiments, the donor group G D The total number of receptor groups G A The total number of .

[0175] In some embodiments of the OLEDs of the present disclosure, at least one donor group G D Each of is independently selected from the group consisting of:

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] Each donor group G D Is at least monovalent; and in structures containing dotted lines, the dotted lines represent the connection group or receptor group G A key.

[0183] In some embodiments of the disclosed OLEDs, at least one acceptor group G A Each of is independently selected from the group consisting of:

[0184] Each receptor group G A Is at least monovalent; and in structures containing dotted lines, the dotted lines represent the connection group or donor group G D key.

[0185] In some embodiments of the OLED of the present disclosure, the first host is selected from the group consisting of:

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] In some embodiments of the disclosed OLEDs, the compound is a sensitizer and the OLED further comprises an acceptor; and wherein the acceptor is selected from the group consisting of: a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0192] 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.

[0193] In some embodiments, the organic layer may further comprise a host, wherein the host comprises a triphenylene containing a benzo-fused thiophene or a benzo-fused furan, wherein any substituent in the host is a non-fused substituent independently selected 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 substituent, wherein n is 1 to 10; and wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0194] In some embodiments, the organic layer may further comprise a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene).

[0195] In some embodiments, the subject can be selected from the group consisting of:

[0196]

[0197]

[0198]

[0199] and combinations thereof.

[0200] In some embodiments, the organic layer may further include a host, wherein the host includes a metal complex.

[0201] In some embodiments, the compound as described herein can be a sensitizer; wherein the device can further comprise a receptor; and wherein the receptor can be selected from the group consisting of: a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0202] In yet another aspect, the OLED of the present disclosure may further comprise an emissive region comprising a compound as disclosed in the above compounds section of the present disclosure.

[0203] Also disclosed is an emitting layer in an OLED, comprising: a first host; and a first emitter; wherein the first emitter is selected from (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n the groups formed;

[0204] Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B )n Ir(L 3 -L 4 ) 3-n for

[0205]

[0206] Among them: Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; each L 1 -L 2 and L 3 -L 4 independently represents an anionic bidentate ligand; n is 1 or 2; each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 is independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; each R S11 、R S12 and R S13 R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; S11 、R S12 and R S13 At least one of the following is selected from the group consisting of: deuterium, silyl, C1 to C3 alkyl, substituted or unsubstituted cycloalkyl, and branched substituted or unsubstituted alkyl with branching occurring at the benzyl position; and the first host comprises at least one donor group G D , and at least one acceptor group G A .

[0207] In some embodiments, at least one of an anode, a cathode, or a new layer disposed above the organic emissive layer functions as an enhancement layer. The enhancement layer comprises a plasmonic material exhibiting surface plasmon resonance, the plasmonic material non-radiatively couples to the emitter material, and transfers excited-state energy from the emitter material to a non-radiative mode of a surface plasmon polariton. The enhancement layer is disposed at a distance from the organic emissive layer that does not exceed a threshold distance, wherein 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 the position at which 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 an opposite side of the organic emissive layer. In some embodiments, the outcoupling layer is disposed on the side of the emissive layer opposite the enhancement layer, but is still capable of outcoupling 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 into free space as photons. In other embodiments, energy is scattered from the surface plasmon mode into other modes of the device, such as, but not limited to, an organic waveguide mode, a substrate mode, or another waveguide mode. If energy is scattered into a non-free-space mode 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 positioned 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.

[0208] The enhancement layer modifies 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, variation in emission intensity with angle, altered emitter material stability, altered OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both produces an OLED device that exploits any of the aforementioned effects. In addition to the specific functional layers described herein and illustrated in the various OLED examples shown in the figures, OLEDs according to the present disclosure may also include any other functional layers commonly found in OLEDs.

[0209] The enhancement layer may 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 dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may comprise at least one of the following: 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, where the effect of the medium as a whole is different from the sum of its material parts. Specifically, we define an optically active metamaterial as a material that has both negative permittivity and 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 distinct from many other photonic structures, such as distributed Bragg reflectors (DBRs), because the dielectric should appear uniform in the direction of propagation on the length scale of the light wavelength. Using terminology understood by those skilled in the art, the dielectric constant of a metamaterial in the direction of propagation can be described using the effective dielectric approximation. Plasmonic and metamaterials offer methods for controlling light propagation, which can enhance OLED performance in a variety of ways.

[0210] In some embodiments, the reinforcement layer is configured as a planar layer. In other embodiments, the reinforcement layer has wavelength-sized features arranged periodically, quasi-periodically, or randomly, or has sub-wavelength-sized features arranged periodically, quasi-periodically, or randomly. In some embodiments, the wavelength-sized features and sub-wavelength-sized features have sharp edges.

[0211] In some embodiments, the outcoupling layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or has sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged. In some embodiments, the outcoupling layer can be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer can be composed of a plurality of nanoparticles disposed above a material. In these embodiments, outcoupling can be adjusted by at least one of: 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 an additional layer disposed above 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 from at least one of a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layer 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, wherein 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. Multiple nanoparticles can have additional layers disposed above them. In some embodiments, the outcoupling layer can be used to adjust the polarization of the emission. Varying the size and periodicity of the outcoupling layer can select the polarization type that preferentially couples to air. In some embodiments, the outcoupling layer also serves as an electrode for the device.

[0212] 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 may comprise a compound as disclosed in the above compound section of the present disclosure.

[0213] In some embodiments, a consumer product comprises an OLED having an anode; a cathode; and an organic emissive layer disposed between the anode and the cathode, wherein the organic emissive layer may comprise a first host; and a first emitter; wherein the first emitter is selected from the group consisting of (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n Groups formed;

[0214] Among them (L 1 -L 2 )n Ir(L A ) 3-n for And (L B ) n Ir(L 3 -L 4 ) 3-n for

[0215] Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring;

[0216] Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands;

[0217] Where n is 1 or 2;

[0218] Each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof;

[0219] Each R S11 、R S12 and R S13 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;

[0220] where R S11 、R S12 and R S13 At least one of the following is selected from the group consisting of: deuterium, silyl, C1 to C3 alkyl, substituted or unsubstituted cycloalkyl, and branched substituted or unsubstituted alkyl with branching occurring at the benzyl position; and

[0221] wherein the first host comprises at least one donor group G D , and at least one acceptor group G A .

[0222] In some embodiments, the consumer product can be one of the following: a flat panel display, a computer monitor, a medical monitor, a television, a sign, a light for interior or exterior lighting and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay having a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.

[0223] In general, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When an electric current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When electrons and holes are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair with an excited energy state. When the exciton relaxes through a photoemission mechanism, light is emitted. In some cases, the exciton can be localized on an excimer or an excited complex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0224] Several OLED materials and configurations are described in US Patent Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

[0225] The first OLEDs used emissive molecules that emitted light from a singlet state ("fluorescence"), as disclosed, for example, in US Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a timeframe of less than 10 nanoseconds.

[0226] Recently, OLEDs with emissive materials that emit light from triplet states ("phosphorescence") have been demonstrated. Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, Vol. 395, 151-154, 1998 ("Baldo-I"); and Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., Vol. 75, Nos. 3, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, columns 5-6, which is incorporated by reference.

[0227] Figure 1 An organic light-emitting device 100 is shown. The figure is not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be manufactured by depositing the layers in sequence. The properties and functions of these various layers and example materials are described in more detail in US Pat. No. 7,279,704, columns 6-10, which is incorporated by reference.

[0228] More examples of each of these layers are available. 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 at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of luminescent 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 at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes comprising a composite cathode having a thin layer of a metal (e.g., Mg:Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0229] 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 in order. Because the most common OLED configuration has the cathode positioned above the anode, and device 200 has cathode 215 positioned below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described for device 100 can be used in the corresponding layers of device 200. Figure 2 An example is provided of how some layers may be omitted from the structure of device 100 .

[0230] Figure 1 and 2The simple layered structures illustrated in the are provided by way of non-limiting examples, and it will be appreciated that embodiments of the present disclosure may be used in conjunction with various other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be obtained by combining the various layers described in different ways, or layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be appreciated that combinations of materials may be used, such as mixtures of hosts and dopants, or more generally, mixtures. In addition, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, the OLED may be described as having an "organic layer" disposed between the cathode and the anode. This organic layer may comprise a single layer, or may further comprise, for example, a layer comprising a plurality of layers. Figure 1 and 2 Multiple layers of said different organic materials.

[0231] Structures and materials not specifically described may also be used, such as OLEDs comprising polymeric materials (PLEDs), such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of another example, an OLED having a single organic layer may be used. OLEDs may be stacked, such as described in U.S. Pat. No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from Figure 1 and 2 For example, the substrate may include angled reflective surfaces to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and / or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0232] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet (as described in U.S. Patents Nos. 6,013,982 and 6,087,196, incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (as described in U.S. Patent No. 6,337,102 to Forrest et al., incorporated by reference in its entirety), and deposition by organic vapor jet printing (OVJP) (as described in U.S. Patent No. 7,431,968, incorporated by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in nitrogen or an inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (as described in U.S. Patents Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety) and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to make it compatible with the specific deposition method. For example, branched or unbranched substituents such as alkyl and aryl groups, preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to withstand solution processing. Substituents with 20 or more carbons may be used, and 3 to 20 carbons are a preferred range. Materials with asymmetric structures may have better solution processability than materials with symmetrical structures because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0233] The device manufactured according to the embodiment of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrode and the organic layer from damage by harmful substances in the environment including moisture, steam and / or gas. The barrier layer can be deposited on the substrate, the electrode, under the substrate, the electrode, or next to the substrate, the electrode, or on any other part of the device (including the edge). The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques and may include compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials can be used for the barrier layer. The barrier layer may be combined with an inorganic compound or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material, as described in U.S. Patent No. 7,968,146, PCT Patent Application No. 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 comprising the barrier layer should be deposited under the same reaction conditions and / or deposited simultaneously. The weight ratio of polymeric to non-polymeric materials 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.

[0234] The devices manufactured according to the embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units), which can be incorporated into a wide variety of electronic products or intermediate components. Examples of the electronic products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels), etc. that can be utilized by end-user product manufacturers. The electronic component modules can optionally include driving electronic devices and / or power supplies. The devices manufactured according to the embodiments of the present disclosure can be incorporated into a wide variety of consumer products, which have one or more electronic component modules (or units) incorporated therein. A consumer product comprising an OLED is disclosed, wherein the OLED includes a compound of the present disclosure in an organic layer in the OLED. The consumer product should include any kind of product containing one or more of one or more light sources and / or some type of visual display. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, phones, cellular phones, tablet computers, tablet phones, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices, and signage. Various control mechanisms can be used to control devices manufactured according to the present disclosure, including passive matrix and active matrix. Many of the devices are intended to be used in a temperature range that is 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).

[0235] More details regarding OLEDs and the definitions described above can be found in US Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0236] The materials and structures described herein can be used in 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.

[0237] In some embodiments, the OLED has one or more characteristics selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

[0238] In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent 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 of less than 10 inches or an area of 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 a lighting panel.

[0239] In some embodiments, the compound can be an emitting dopant. In some embodiments, the compound can produce emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also referred to as E-type delayed fluorescence, see, for example, U.S. Application No. 15 / 700,352, which is incorporated herein by reference in its entirety), triplet-triplet elimination, or a combination of these processes. In some embodiments, the emitting dopant can be a racemic mixture, or can be enriched in a kind of enantiomer. In some embodiments, the compound can be homogeneous (each ligand is identical). In some embodiments, the compound can be mixed (at least one ligand is different from others). In some embodiments, when there is more than one ligand coordinated to the metal, the ligand can be all the same. In some other embodiments, at least one ligand is different from other ligands. In some embodiments, each ligand can be different from each other. This also holds true in the embodiment where the ligand coordinated to the metal can be connected to form a tridentate, quadridentate, pentadentate, or hexadentate ligand with other ligands coordinated to the metal. Thus, where coordinating ligands are linked together, in some embodiments all of the ligands may be identical, and in some other embodiments at least one of the linked ligands may be different from the other ligand(s).

[0240] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain an acceptor in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound can be used as a component of an exciplex to be used as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the acceptor and the acceptor will emit energy or further transfer energy to the final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can be generated by any one or all of the sensitizer, the acceptor, and the final emitter.

[0241] According to another aspect, a formulation comprising a compound described herein is also disclosed.

[0242] 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 compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.

[0243] In another aspect of the present invention, a formulation comprising the novel compounds disclosed herein is described. The formulation may 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.

[0244] The present disclosure encompasses any chemical structure comprising the novel compounds of the present disclosure or their monovalent or multivalent variants. In other words, the compounds of the present invention or their monovalent or multivalent variants can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of: monomers, polymers, macromolecules, and supramolecules (also referred to as supermolecules). As used herein, a "monovalent variant of a compound" refers to a portion that is identical to the compound but has one hydrogen removed and replaced with a bond to the rest of the chemical structure. As used herein, a "multivalent variant of a compound" refers to a portion that is identical to the compound but has more than one hydrogen removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecules, the compounds of the present invention can also be incorporated into supramolecular complexes without covalent bonds.

[0245] D. Combinations of Compounds of the Disclosure with Other Materials

[0246] The materials described herein as suitable for use in a particular layer of an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used in combination with a wide variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0247] a) Conductive dopant:

[0248] The charge transport layer can be doped with a conductivity dopant to substantially alter its charge carrier density, which in turn changes its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the semiconductor's Fermi level can also be achieved. The hole transport layer can be doped with a p-type conductivity dopant, and n-type conductivity dopant is used in the electron transport layer.

[0249] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the references disclosing those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.

[0250]

[0251] b)HIL / HTL:

[0252] 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; polymers containing fluorocarbons; polymers having a conductive dopant; 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 x ; p-type semiconducting organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile; metal complexes; and cross-linkable compounds.

[0253] Examples of aromatic amine derivatives for use in HILs or HTLs include, but are not limited to, the following general structure:

[0254]

[0255] Ar 1 to Ar 9 Each of the following is selected from the group consisting of aromatic hydrocarbon cyclic compounds: benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units, which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic 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 Ar may be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0256] In one aspect, Ar 1 to Ar 9 Independently selected from the group consisting of:

[0257]

[0258] Where k is an integer from 1 to 20; X 101 to X 108 is C (including CH) or N; Z 101 It is NAr 1 , O or S; Ar 1 Having the same groups as defined above.

[0259] Examples of metal complexes used in the HIL or HTL include, but are not limited to, the following general formula:

[0260]

[0261] Wherein Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 Independently selected from C, N, O, P and S; L 101 is an auxiliary ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0262] 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 relative + The minimum oxidation potential in solution due to the / Fc coupling is less than about 0.6 V.

[0263] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with references to those materials disclosing those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, J P2007091719, JP2008021687, JP2014-009196, KR20110088898, KR2013007 7473, TW201139402, US06517957, US20020158242, US20030162053, US2005 0123751, US20060182993, US20060240279, US20070145888, US2007018187 4. US20070278938, US20080014464, US20080091025, US20080106190, US200 80124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US201 1007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, US5061569, US5639914, WO0 5075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO201 3087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO 2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921,WO2014034791, WO2014104514, WO2014157018. ,

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] c) EBL:

[0272] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in substantially higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. In addition, a blocking layer can be used to confine emission to desired areas 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.

[0273] d) Subject:

[0274] 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 may contain a host material using the metal complex as a dopant material. Examples of host materials 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 the triplet energy of the dopant. Any host material can be used with any dopant as long as the triplet criterion is met.

[0275] Examples of metal complexes used as hosts preferably have the following general formula:

[0276]

[0277] Wherein Met is a metal; (Y 103 -Y 104) is a bidentate ligand, Y 103 and Y 104 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.

[0278] In one aspect, the metal complex is:

[0279]

[0280] where (ON) is a bidentate ligand with a metal coordinated to O and N atoms.

[0281] In another aspect, Met is selected from Ir and Pt. In another aspect, (Y 103 -Y 104 ) is a carbene ligand.

[0282] In one aspect, the host compound contains at least one selected from the following group: a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units, which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic 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 may be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0283] In one aspect, the subject compound contains at least one of the following groups in the molecule:

[0284]

[0285] where R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, 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 the same definition as Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X 101 to X 108 Z is independently selected from C (including CH) or N. 101 and Z 102 Independently selected from NR 101 , O or S.

[0286] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with references disclosing those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US2009 0017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, U S20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO200 6114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO20090 86028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133 649. WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803,

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] e) Other emitters:

[0293] One or more other emitter dopants may be used in combination with the compounds of the present invention. Examples of other emitter dopants are not particularly limited, and any compound can be used as long as the compound is commonly used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can produce 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.

[0294] Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with references disclosing those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120090133653. 32054, KR20130043460, TW201332980, US06699599, US06916554, US200100 19782, US20020034656, US20030068526, US20030072964, US20030138657, U U.S. 20060202194, US20060251923, US20070034863, US20070087321, US200701 03060, US20070111026, US20070190359, US20070231600, US2007034863, US 2007104979, US2007104980, US2007138437, US2007224450, US2007278936 , US20080020237, US20080233410, US20080261076, US20080297033, US2008 05851, US2008161567, US2008210930, US20090039776, US20090108737, US 20090115322, US20090179555, US2009085476, US2009104472, US201000905 91. US20100148663, US20100244004, US20100295032, US2010102716, US20 10105902, 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。、

[0295]

[0296]

[0297]

[0298]

[0299]

[0300] f)HBL:

[0301] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in substantially higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. In addition, a blocking layer can be used to confine emission to desired areas 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.

[0302] In one aspect, the compounds used in HBL contain the same molecules or the same functional groups as used in the subjects described above.

[0303] In another aspect, the compound used in HBL contains at least one of the following groups in the molecule:

[0304]

[0305] Where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0306] g)ETL:

[0307] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.

[0308] In one aspect, the compound used in the ETL contains at least one of the following groups in the molecule:

[0309]

[0310] where R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, 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 a similar definition to Ar above. 1 to Ar3 has a similar definition to Ar mentioned above. k is an integer from 1 to 20. X 101 to X 108 is selected from C (including CH) or N.

[0311] In another aspect, the metal complex used in the ETL contains (but is not limited to) the following general formula:

[0312]

[0313] wherein (ON) or (NN) is a bidentate ligand having a metal coordinated to atoms O, N or N, N; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.

[0314] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with references disclosing those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, and US2009018179634. 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,

[0315]

[0316]

[0317]

[0318] h) Charge Generation Layer (CGL)

[0319] In tandem or stacked OLEDs, the CGL plays a fundamental role in performance. It consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and electrodes. Electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductivity dopants used in the transport layer.

[0320] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, etc., can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0321] 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 present invention. For example, many materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. Therefore, the present invention as required can include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

[0322] E. Experimental Data

[0323]

[0324] A mixture of 1-(3,5-dimethylphenyl)-6-isopropylisoquinoline (28.5 g, 103.5 mmol, 2.0 equiv) in 2-ethoxyethanol (250 mL) and DIUF water (83 mL) was bubbled with nitrogen for 10 minutes. Iridium (III) chloride hydrate (16.35 g, 51.7 mmol, 1.0 equiv) was added and bubbling continued for 5 minutes. The reaction mixture was heated at 100 ° C for 18 hours. The reaction mixture was cooled to room temperature. The suspension was filtered and the solid was washed with water (5 mL) and then with methanol (3×20 mL) and dried on the filter funnel to give di-μ-chloro-tetrakis[(1-(3,5-dimethylphenyl)-2′-yl)-6-isopropylisoquinolin-2-yl]diiridium(III) (19.7 g, 49% yield) as a red solid.

[0325] Pentane-2,4-dione (0.290 g, 2.90 mmol, 3.0 equiv) and powdered potassium carbonate (0.80 g, 5.80 mmol, 6.0 equiv) were added sequentially to a suspension of di-μ-chloro-tetrakis[(1-(3,5-dimethylphenyl)-2'-yl)-6-isopropylisoquinolin-2-yl]diiridium(III) (1.5 g, 0.966 mmol, 1.0 equiv) in methanol (15 mL) and dichloromethane (5 mL). The reaction mixture was heated at 45° C. for 30 minutes. The mixture was cooled to room temperature and then concentrated under reduced pressure. The residue was purified on a silica gel column eluting with a gradient of 0 to 60% dichloromethane / heptane to give bis[(1-(3,5-dimethylphenyl)-2'-yl)-6-isopropylisoquinolin-2-yl]-(2,4-pentanedionyl-k2O,O')iridium(III) (0.9 g, 56% yield) as a red solid.

[0326]

[0327] A solution of di-μ-chloro-tetrakis[(1-(3,5-dimethylphenyl)-2'-yl)-6-isopropylisoquinolin-2-yl]diiridium(III) (0.875 g, 0.6 mmol, 1.0 equiv) in 2-ethoxyethanol (20 mL) was sparged with nitrogen for 10 minutes. 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.52 g, 2.2 mmol, 3.8 equiv) was added via syringe. After stirring for 5 minutes, powdered potassium carbonate (0.61 g, 4.4 mmol, 7.8 equiv) was added and the reaction mixture was stirred at room temperature for 16 hours in a flask covered with foil to exclude light. The reaction mixture was heated at 45° C. for 16 hours. The reaction mixture was cooled to room temperature and DIUF water (50 mL) was added. The suspension was filtered and the red solid was washed with DIUF water (100 mL) and methanol (20 mL), then dried in a vacuum oven at 45° C. for 1 hour. The red solid (0.85 g) was dry loaded onto basic alumina (30 g) and purified on an Interchim automated chromatography system (80 g silica gel cartridge) eluting with 10-25% dichloromethane / hexanes to afford bis[1-(3,5-dimethylphenyl-2-yl))-6-isopropylisoquinolin-2-yl]-[3,7-diethyl-3,7-dimethylnonane-4,6-dione-k 2 O,O′]iridium(III) (0.47 g, 42% yield) as a red solid.

[0328] Device Examples

[0329] All example devices were operated in high vacuum (<10 -7 The anode electrode is made by thermal evaporation. The cathode is made of indium tin oxide (ITO). Liq (8-hydroxyquinoline lithium), followed by All devices were immediately packaged in a nitrogen glove box (<1 ppm H2O and O2) with epoxy-sealed glass lids after fabrication, and moisture absorbers were incorporated into the packaging. The organic stack of the device example consisted of the following: starting with the ITO surface, the hole injection layer (HIL), the LG101 (purchased from LG Chem); as the hole transport layer (HTL) HTM; as electron blocking layer (EBL) EBM; contains body and 3% emitter The emission layer (EML) and the electron transport layer (ETL) doped with 35% ETM Liq (lithium 8-hydroxyquinoline). Table 1 shows the device layer thicknesses and materials.

[0330] Table 1. Device layer materials and thicknesses

[0331]

[0332] The chemical structures of the materials used in the device are shown below:

[0333]

[0334] After fabrication, the devices were tested for electroluminance (EL) and current density-voltage-luminance (JVL) characteristics. For this purpose, each sample was tested at 10 mA / cm2 using a 2-channel Keysight B2902A SMU. 2 The current density was set and measured using a PhotoResearch PR735 spectroradiometer. The radiance (W / str / cm 2 ), and total integrated photon counts. Each device was then placed under a large area silicon photodiode for JVL scanning. The device was operated at 10 mA / cm 2 The integrated photon count under the voltage is scanned from 0 to 200mA / cm 2 The external quantum efficiency (EQE) of the device was calculated using total integrated photon counting. All results are summarized in Table 2.

[0335] Table 2.

[0336]

[0337] Table 2 is an overview of the performance of the electroluminescent devices. First, when each emitter is doped in the same host (Device 1 versus Device 3, and Device 2 versus Device 4), the device of the present invention with Compound 1 as the emitter (Device 1) exhibits a significantly narrower FWHM. In general, the FWHM of phosphorescent emitter complexes is broad, as shown by the typical 57 or 60 nm exhibited by the comparative devices with emitter Compound 2 (Device 3 and Device 4). Achieving a narrow FWHM is an ongoing goal. A narrower FWHM provides better color purity for display applications. As background information, the ideal line shape is a single wavelength (single line). As can be seen here, Compound 1 has a FWHM that is approximately 10 nm smaller. In earlier OLED research work, narrowing line shapes have been slowly achieved on the nanometer scale. Therefore, the 8 nm and 11 nm reductions seen here are significantly unexpected results. Secondly, when the same emitter is doped into different hosts (Device 1 versus Device 2, and Device 3 versus Device 4), the device of the present invention with Host 1 (Device 1) has demonstrated significant improvements in terms of reduced voltage, increased EQE, and LE values. When Device 1 is compared to Device 2, the voltage is reduced by 26%, the EQE is increased by 33%, and the LE is increased by 41%. Device 3 also demonstrates similar improvements relative to Device 4. These improvements are higher than any value attributable to experimental error, and the observed improvements are significant and unexpected. In summary, the devices of the present invention described herein with a specific type of emitter and host combination have demonstrated unexpected synergistic advantages over other similar emitter and host combinations.

Claims

1. A composition for use in an organic emission layer of an organic light-emitting device, comprising: the first entity; and a first emitter; wherein the first emitter is selected from (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n Groups formed; Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L 3 -L 4 ) 3-n for Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands; Where n is 1 or 2; where R S1 independently selected from the group consisting of 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, cycloalkyl, partially or fully fluorinated versions thereof, partially or fully deuterated versions thereof, and combinations thereof; Each R S2 、R S3 、R S4 、R S5 、R S6 independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; Each R S11 、R S12 and R S13 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; where R S11 、R S12 and R S13 at least one of which is selected from the group consisting of deuterium, silyl, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and combinations thereof; where R S1 、R S2 、R S3 、R S4 、R S5 、R S6 、R S11 、R S12 and R S13 Any two substituents may be joined or fused to form a ring; wherein the first host has the formula G D -LG A ; and L is a direct bond or an organic linking group, wherein the donor group G D independently comprising at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and The receptor group G A Independently comprises at least one moiety selected from the group consisting of nitrile, isonitrile, fluoride, a six-membered aromatic ring having at least one nitrogen, and a five-membered aromatic ring having at least two heteroatoms.

2. The composition according to claim 1, wherein R S11 、R S12 and R S13 At least one of the following is selected from the group consisting of deuterium, a silyl group, a C1 to C3 alkyl group, a substituted or unsubstituted cycloalkyl group, and a branched substituted or unsubstituted alkyl group in which branching occurs at the benzyl position.

3. The composition of claim 1, wherein the first emitter is 4. The composition of claim 1, wherein the first emitter is selected from the group consisting of emitters having the formula (L B ) n Ir(L 3 -L 4 ) 3-n A group consisting of the following structure: Wherein X' is selected from the group consisting of: BR e BR e R f 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 ; Each R e 、R f and R S14 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and where R e 、R f and R S14 Any two substituents of may be joined or fused to form a ring.

5. The composition according to claim 3, wherein the ligand (L 1 -L 2 ) is selected from the group consisting of: where Y 1 To Y 10 are each independently selected from the group consisting of carbon and nitrogen; Wherein Y' is selected from the group consisting of: BR e BR e R f 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 ; where R e and R f optionally fused or joined to form a ring; where R a and R b Each independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; where R a 、R b 、R e and R f each of which is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl; and where R a and R b Two adjacent substituents of are optionally fused or joined to form a ring or to form a multidentate ligand.

6. The composition according to claim 3, wherein the ligand (L 1 -L 2 ) is selected from the group consisting of: L based on structure 1 1 -L 2 -1-i: L based on structure 2 1 -L 2 -2-i: L based on structure 3 1 -L 2 -3-i: L based on structure 4 1 -L 2 -4-i: L based on structure 5 1 -L 2 -5-i: L based on structure 6 1 -L 2 -6-i: L based on structure 7 1 -L 2 -7-i: L based on structure 8 1 -L 2 -8-i: L based on structure 9 1 -L 2 -9-i: L based on structure 10 1 -L 2 -10-i: L based on structure 11 1 -L 2 -11-i: L based on structure 12 1 -L 2 -12-i: Based on structure 13 L 1 -L 2 -13-i: L based on structure 14 1 -L 2 -14-i: and L based on structure 15 1 -L 2 -15-i: L based on structure 16 1 -L 2 -16-i: L based on structure 17 1 -L 2 -17-i: Where i is an integer from 1 to 810, and for each i, R E and G are defined as follows: where R 1 to R 45 Has the following structure: and Among them G 1 to G 18 Has the following structure:

7. A composition for use in an organic emission layer of an organic light-emitting device, comprising: the first entity; and a first emitter; The first emitter is (L 1 -L 2 ) n Ir(L A ) 3-n ; Among them (L 1 -L 2 ) n Ir(L A ) 3-n for Among them L 1 -L 2 represents an anionic bidentate ligand; Where n is 1 or 2; wherein the ligand L A Select from the group consisting of: L based on structure A1 A1 -k: L based on structure A2 A2 -k: L based on structure A3 A3 -k: L based on structure A4 A4 -k: L based on structure A5 A5 -k: and L based on structure A6 A6 -k: Where k is an integer from 2 to 600, and for each k, R D 、R F and R G The definition is as follows: where R D1 to R D23 Has the following structure: wherein the first host has the formula G D -LG A ; and L is a direct bond or an organic linking group, wherein the donor group G D independently comprising at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and The receptor group G A Independently comprises at least one moiety selected from the group consisting of nitrile, isonitrile, fluoride, a six-membered aromatic ring having at least one nitrogen, and a five-membered aromatic ring having at least two heteroatoms.

8. The composition of claim 7, wherein the first emitter is selected from the group consisting of: 1 -L 2 -mi)2Ir(L An -k)(L 1 -L 2 -1-1)2Ir(L A1 -1) to (L 1 -L 2 -17-810)2Ir(L A6 -600), wherein m is an integer from 1 to 17, i is an integer from 1 to 810, n is an integer from 1 to 6, and k is an integer from 2 to 600.

9. The composition according to claim 4, wherein R S11 、R S12 and R S13 At least one of is selected from the group consisting of:

10. The composition of claim 4, wherein the first emitter is selected from the group consisting of: When there is more than one R S11 or R S13 When each R S11 and R S13 Can be the same or different.

11. The composition according to claim 4, wherein the ligand L B Select from the group consisting of: L based on structure B1 B1 -h: L based on structure B2 B2 -h: L based on structure B3 B3 -h: L based on structure B4 B4 -h: L based on structure B5 B5 -h: Where h is an integer from 1 to 1170, and for each h, R H and G are defined as follows: where R H1 to R H65 Has the following structure: Among them G 1 to G 16 Has the following structure:

12. The composition according to claim 11, wherein L 3 -L 4 Select from the group consisting of: Based on the formula The structure of L Cj-I ;and Based on the formula The structure of L Cj-II , where j is an integer from 1 to 1416, where for L Cj-I and L Cj-II Each L in Cj , R 201 and R 202 Each is independently defined as follows: where R D1 to R D246 Has the following structure:

13. The composition of claim 12, wherein the first emitter is selected from the group consisting of: Bp -h)2Ir(L Cj-I ) of (L B1 -1)2Ir(L C1-I ) to (L B5 -1170)2Ir(L C1416-I ), and based on the general formula (L Bp -h)2Ir(L Cj-II ) of (L B1 -1)2Ir(L C1-II ) to (L B5 -1170)2Ir(L C1416-II ); wherein p is an integer from 1 to 5, and h is an integer from 1 to 1170.

14. The composition of claim 1, wherein the donor group G D independently comprising at least one moiety selected from the group consisting of: wherein X is selected from the group consisting of: O, S, Se, and NR; and wherein each R is independently selected from (i) G A , (ii) with G A an organic linking group, and (iii) a terminal group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an aryl group, a heteroaryl group, and combinations thereof; and wherein the receptor group G A independently comprising at least one moiety selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole.

15. The composition of claim 1, wherein the donor group G D Independently selected from the group consisting of: Each donor group G D is at least the unit price; and In the structure containing a dotted line, the dotted line represents the connection group or receptor group G A and wherein the receptor group G A Independently selected from the group consisting of: Each receptor group G A is at least the unit price; and In the structure containing a dotted line, the dotted line represents the connection group or donor group G D key.

16. The composition of claim 1, wherein the first entity is selected from the group consisting of:

17. The composition according to claim 5, wherein the ligand (L 1 -L 2 ) is selected from the group consisting of: where R a ' and R b ' Each independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; where R a ' and R b ' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and where R a ' and R b Two adjacent substituents of ' may be fused or joined to form a ring or to form a multidentate ligand.

18. The composition of claim 1, wherein n is 2.

19. The composition of claim 1, wherein the first host is partially or fully deuterated.

20. An organic light-emitting device (OLED), comprising: anode; cathode; and an organic emissive layer disposed between the anode and the cathode, comprising: the first entity; and a first emitter; wherein the first emitter is selected from (L 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(L 3 -L 4 ) 3-n Groups formed; Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L 3 -L 4 ) 3-n for Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands; Where n is 1 or 2; Each R S1 、R S2 、R S3 、R S4 、R S5 、R S6 independently selected from the group consisting of alkyl, cycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; Each R S11 、R S12 and R S13 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; where R S11 、R S12 and R S13 at least one of which is selected from the group consisting of deuterium, silyl, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and combinations thereof; where R S1 、R S2 、R S3 、R S4 、R S5 、R S6 、R S11 、R S12 and R S13 Any two substituents may be joined or fused to form a ring; wherein the first host comprises at least one donor group G D , and at least one acceptor group G A ; wherein the first emitter is a sensitizer and the OLED further comprises an acceptor; and wherein the acceptor is selected from the group consisting of a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

21. An organic light-emitting device (OLED), comprising: anode; cathode; and an organic emissive layer disposed between the anode and the cathode, comprising: the first entity; and a first emitter; wherein the first emitter is selected from the group consisting of emitters having the formula (L B ) n Ir(L 3 -L 4 ) 3-n A group consisting of the following structures; Each R S11 、R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring; Among them L 3 -L 4 independently represent anionic bidentate ligands; Where n is 1 or 2; Wherein X' is selected from the group consisting of: BR e BR e R f 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 ; Each R S11 、R S12 、R S13 、R e 、R f and R S14 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; where R S11 、R S12 and R S13 at least one of which is selected from the group consisting of deuterium, silyl, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and combinations thereof; where R S11 、R S12 and R S13 Any two substituents may be joined or fused to form a ring; where R e 、R f and R S14 Any two substituents may be joined or fused to form a ring; wherein the first host has the formula G D -LG A ; and L is a direct bond or an organic linking group, wherein the donor group G D independently comprising at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and The receptor group G A independently comprising at least one moiety selected from the group consisting of a nitrile, an isonitrile, a fluoride, a six-membered aromatic ring having at least one nitrogen, and a five-membered aromatic ring having at least two heteroatoms; wherein the ligand L B Select from the group consisting of: L based on structure B1 B1 -h: L based on structure B2 B2 -h: L based on structure B3 B3 -h: L based on structure B4 B4 -h: L based on structure B5 B5 -h: Where h is an integer from 1 to 1170, and for each h, R H and G are defined as follows: where R H1 to R H65 Has the following structure: Among them G 1 to G 16 Has the following structure: Among them L 3 -L 4 Select from the group consisting of: Based on the formula The structure of L Cj-I ;and Based on the formula The structure of L Cj-II , where j is an integer from 1 to 1416, where for L Cj-I and L Cj-II Each L in Cj , R 201 and R 202 Each is independently defined as follows: where R D1 to R D246 Has the following structure:

22. The OLED of claim 21, wherein the first emitter is selected from the group consisting of: Bp -h)2Ir(L Cj-I ) of (L B1 -1)2Ir(L C1-I ) to (L B5 -1170)2Ir(L C1416-I ), and based on the general formula (L Bp -h)2Ir(L Cj-II ) of (L B1 -1)2Ir(L C1-II ) to (L B5 -1170)2Ir(L C1416-II ); wherein p is an integer from 1 to 5, and h is an integer from 1 to 1170.

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