Organic electroluminescent materials and devices

Abstract

This application relates to organic electroluminescent materials and devices. Provided is an OLED having an anode, a cathode, and an organic emissive layer disposed between the anode and the cathode. The emissive layer includes 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 ; wherein (L 1 -L 2 ) n Ir(L A ) 3‑n is #imgabs0# and (L B ) n Ir(L 3 -L 4 ) 3‑n is #imgabs1# or #imgabs2#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Application No. 63 / 002,564, filed Mar. 31, 2020, under 35 U.S.C. § 119(e), the entire content of which is incorporated herein by reference. Technical Field

[0003] The present disclosure generally relates to organometallic compounds and formulations and their various uses, including as emitters in devices such as organic light emitting diodes and related electronic devices. Background Art

[0004] For various reasons, optoelectronic devices that utilize organic materials have become increasingly popular. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for a cost advantage over inorganic devices. Additionally, the inherent properties of organic materials, such as their flexibility, can make them more suitable for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

[0005] 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.

[0006] One application of phosphorescent emissive molecules is full-color displays. Industry standards for such displays require pixels that are suitable for emitting specific colors (referred to as “saturated” colors). Specifically, these standards require saturated red, green, and blue pixels. Alternatively, an OLED 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 technique can also be used for OLEDs. White OLEDs can be single emissive layer (EML) devices or stacked structures. Color can be measured using CIE coordinates well known in the art. Summary of the Invention

[0007] In one aspect, the present disclosure provides an OLED comprising: an anode; a cathode; and an organic emissive layer disposed between the anode and the cathode. The emissive layer comprises: 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 ) nIr(L 3 -L 4 ) 3-n The compounds of the group composed;

[0008] 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

[0009] 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, silane, 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 G A .

[0010] In another aspect, the present disclosure provides a formulation of a first emitter compound of the present disclosure.

[0011] In yet another aspect, the present disclosure provides a consumer product comprising the OLED of the present disclosure. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] Figure 1 An organic light emitting device is shown.

[0013] Figure 2 An inverted organic light-emitting device without a separate electron transport layer is demonstrated. DETAILED DESCRIPTION

[0014] A. Terminology

[0015] Unless otherwise specified, the following terms used herein are defined as follows:

[0016] 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 a "small molecule" may actually be quite large. In some cases, a small molecule may include a repeating unit. For example, the use of a long chain alkyl group as a substituent does not remove a molecule from the "small molecule" category. Small molecules can also be incorporated into polymers, for example as a side group on a polymer backbone or as part of a backbone. Small molecules can also serve as the core portion of a dendritic polymer, which consists of a series of chemical shells built on the core portion. The core portion of a dendritic polymer can be a fluorescent or phosphorescent small molecule emitter. A dendritic polymer can be a "small molecule", and all dendritic polymers currently used in the field of OLEDs are considered to be small molecules.

[0017] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where 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, there may be other layers between the first and second layers. For example, a cathode may be described as being "disposed above" an anode even though various organic layers are present between the cathode and the anode.

[0018] 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.

[0019] When a ligand is believed to directly contribute to the photosensitive property of an emissive material, the ligand may be referred to as "photosensitive." When a ligand is believed not to contribute to the photosensitive property of an emissive material, the ligand may be referred to as "ancillary," but the ancillary ligand may alter the properties of the photosensitive ligand.

[0020] 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 the ionization potential (IP) is measured as a 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.

[0021] As used herein, and as one skilled in the art would generally understand, 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 farther away from the vacuum level in a downward direction. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0022] The terms "halo," "halogen," and "halo" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0023] The term "acyl" refers to a substituted carbonyl (C(O)-R s ).

[0024] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0025] The term "ether" refers to -OR s Group.

[0026] The terms "thio" or "thioether" are used interchangeably and refer to -SR s Group.

[0027] The term "sulfinyl" refers to -S(O)-R s Group.

[0028] The term "sulfonyl" refers to -SO 2 -R s Group.

[0029] The term "phosphino" refers to -P(R s ) 3 A group in which each R s Can be the same or different.

[0030] The term "silyl" refers to -Si(R s ) 3 A group in which each R s Can be the same or different.

[0031] The term "boryl" refers to -B(R s ) 2 Group or its Lewis adduct -B(R s ) 3 Group, where R s Can be the same or different.

[0032] In each of the above, R s It may be 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.

[0033] The term "alkyl" refers to and includes straight and branched chain 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, etc. In addition, the alkyl group may be optionally substituted.

[0034] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are cycloalkyl groups containing 3 to 12 ring carbon atoms, and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. In addition, the cycloalkyl group may be optionally substituted.

[0035] 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.

[0036] 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.

[0037] The term "alkynyl" refers to and includes straight and branched chain alkynyl groups. Alkynyl groups are essentially alkyl groups that include at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are alkynyl groups containing two to fifteen carbon atoms. In addition, alkynyl groups may be optionally substituted.

[0038] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.

[0039] 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. 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, etc., and cyclic ethers / thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. In addition, heterocyclic groups can be optionally substituted.

[0040] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. Polycyclic rings may have two or more rings in which two carbons are common to two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic and / or heteroaryl. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, and more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, , perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted.

[0041] The term "heteroaryl" refers to and includes 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 with 5 or 6 ring atoms, and the rings may have 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, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocycle and / or heteroaryl. Heteropolycyclic aromatic ring systems may have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls containing three to thirty carbon atoms, preferably three to twenty carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, 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 is substituted with 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and aza analogs thereof. In some embodiments, the heteroaryl group is substituted with 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and aza analogs thereof. In some embodiments, the heteroaryl group is substituted with 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and aza analogs thereof. In some embodiments, the heteroaryl group is substituted with 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and aza analogs thereof. In some embodiments, the heteroaryl group is substituted with 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and aza analogs thereof.

[0042] 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 corresponding aza analogs are of particular interest.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] In other cases, the most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0048] The terms "substituted" and "substituted" refer to the bonding of substituents other than H to the relevant positions, 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 indicates disubstituted, the two R 1 must not be H. Similarly, when R 1 When it indicates zero or no substitution, R 1 For example, it can be hydrogen with available valences for the ring atoms, such as the carbon atoms of 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 in the ring atoms.

[0049] 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 envision from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloaralkyl. In one example, the term substitution includes a combination of two to four listed groups. In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution 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 including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0050] 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 any limitation, azatriphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.

[0051] 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. US 2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Review) 2007, 46, 7744-65 (which are incorporated by reference in their entirety) respectively describe the deuteration of methylene hydrogen in benzylamine and the effective way to replace aromatic ring hydrogen with deuterium.

[0052] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name can be written as if it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0053] In some cases, a pair of adjacent substituents can be optionally joined or fused to form a ring. Preferred rings are five, six or seven-membered carbocyclic or heterocyclic rings, including two cases where 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 can be immediately adjacent to each other on the same ring, or on two adjacent rings with 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.

[0054] B. Compounds of the Disclosure

[0055] 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 ;

[0056] 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

[0057] Each R S11 , R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring;

[0058] Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands;

[0059] Where n is 1 or 2;

[0060] 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;

[0061] 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, thiol, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;

[0062] 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

[0063] The first host comprises at least one donor group G D , and at least one acceptor group G A .

[0064] C. OLEDs and Devices of the Present Disclosure

[0065] 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.

[0066] 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 Groups formed;

[0067] Among them (L 1 -L 2 ) n Ir(L A ) 3-n for And (L B ) n Ir(L3 -L 4 ) 3-n for

[0068] 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 general substituents described above; S11 , R S12 and R S13 At least one of is selected from the group consisting of: deuterium, silane, 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

[0069] 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.

[0070] In some embodiments of OLEDs, each R S11 , RS12 and R S13 are 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, thiol, boryl, and combinations thereof.

[0071] In some embodiments of OLEDs, n is two.

[0072] 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:

[0073] Compound B and compound C Compound D and compound E 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,SO 2 , CR e R f 、SiR e R f and GeR e R f ; where each R', R" 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.

[0074] 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 has the structure

[0075] 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:

[0076]

[0077] 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,SO 2 , CR e R f 、SiR e R f and GeR e R f ; R e and R f are optionally fused or joined to form a ring; 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.

[0078] 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:

[0079]

[0080]

[0081]

[0082] 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.

[0083] 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:

[0084] Based on structure 1, L 1 -L 2 -1-i: Based on structure 2 L 1 -L 2 -2-i: Based on structure 3 L 1 -L 2 -3-i: Based on structure 4 L 1 -L 2 -4-i: Based on structure 5 L 1 -L 2 -5-i: Based on structure 6 L 1 -L 2 -6-i: Based on structure 7, L 1 -L 2 -7-i: Based on structure 8, L 1 -L 2 -8-i: Based on structure 9 L 1 -L 2 -9-i: Based on structure 10 L 1 -L 2 -10-i: Based on structure 11, L 1 -L 2 -11-i: Based on structure 12, L 1 -L 2 -12-i: Based on structure 13, L 1 -L 2 -13-i: Based on structure 14 L 1 -L 2 -14-i: and L based on structure 15 1 -L 2 -15-i: Based on structure 16 L 1 -L 2 -16-i: Based on structure 17, L 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:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] where R 1 to R 45 has the following structure:

[0092] and

[0093] where G 1 to G 18 has the following structure:

[0094] In some embodiments of the OLED, where the first emitter is compound A, each R S1 , R S2 , R S3 , R S4 , R S5 , R S6 is 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.

[0095] In some embodiments of the OLED, where the first emitter is compound A, the L A ligand is selected from the group consisting of:

[0096] L A1 -k based on structure A1: L A2 -k based on structure A2: L A3 -k based on structure A3: Based on structure A4 L A4 -k: Based on structure A5 L 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:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Where R D1 To R D23 Has the following structure:

[0103]

[0104]

[0105] 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) 2 Ir(L An -k)(L 1 -L 2 -1-1) 2 Ir(L A1 -1) to (L 1 -L 2 -17-810) 2 Ir(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.

[0106] In some embodiments of OLEDs, wherein the first emitter is compound A, the first emitter may be selected from the group consisting of:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] 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:

[0115]

[0116]

[0117] 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:

[0118]

[0119]

[0120] When there is more than one R S11 or R S13 When each R S11 and R S13 Can be the same or different.

[0121] 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:

[0122] Based on structure B1, L B1 -h: Based on structure B2 B2 -h:

[0123] Based on structure B3 B3 -h: Based on structure B4 L B4 -h: and

[0124] Based on structure B5 B5 -h

[0125] Where h is an integer from 1 to 1170, and for each h, R H and G are defined as follows:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] Where R H1 To R H65 Has the following structure:

[0134]

[0135] Among them G 1 To G 18 Has the following structure:

[0136] 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:

[0137] Based on the formula The structure of LCj-I ;and

[0138] 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 Cj , R 201 and R 202 Each is independently defined as follows:

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] Where R D1 To R D246 Has the following structure:

[0148]

[0149]

[0150]

[0151]

[0152] 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 only the corresponding R 201 and R 202 Those L defined as one of the following structures Cj-I and L Cj-II Groups: R D1 , RD3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D18 , R D20 , R D22 , R D37 , R D40 , R D41 , R D42 , R D43 , R D48 , R D49 , R D50 , R D54 , R D55 , R D58 , R D59 , R D78 , R D79 , R D81 , R D87 , R D88 , R D89 , R D93 , R D116 , R D117 , R D118 , R D119 , R D120 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D147 , R D149 , R D151 , R D154 , R D155 , R 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.

[0153] 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:

[0154]

[0155]

[0156] In some embodiments of OLEDs, the first emitter is selected from the group consisting of: based on the general formula (L Bp -h) 2 Ir(L Cj-I ) of (L B1 -1) 2 Ir(L C1-I ) to (L B4 -1170) 2 Ir(L C1416-I ), and based on the general formula (L Bp -h) 2 Ir(L Cj-II ) of (L B1 -1) 2 Ir(L C1-II ) to (L B4 -1170) 2 Ir(L C1416-II ); wherein p is an integer from 1 to 4, and h is an integer from 1 to 1170.

[0157] 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:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] In some embodiments of the OLED, the first emitter is selected from the group consisting of: 1 -L 2 ) n Ir(L A ) 3-n and (L B ) n Ir(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 compounds independently comprises at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.

[0165] In some embodiments of the OLED of the present disclosure, at least one donor group G D Each of the compounds independently comprises at least one moiety selected from the group consisting of amino, indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.

[0166] In some embodiments of the OLED, wherein the first host has the 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.

[0167] In some embodiments of the OLED of the present disclosure, 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.

[0168] In some embodiments of the OLED 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:

[0169]

[0170] wherein X is selected from the group consisting of: O, S, Se, and NR; and wherein each R is independently selected from (i) GA , (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.

[0171] In some embodiments of the OLED of the present disclosure, at least one acceptor group G A Each of the above 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.

[0172] 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 ; where each donor group G D and receptor group G A Can be the same or different; any pair of donor groups G D 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 .

[0173] In some embodiments of the OLED of the present disclosure, at least one donor group G D Each of is independently selected from the group consisting of:

[0174]

[0175]

[0176]

[0177]

[0178]

[0179] 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.

[0180] In some embodiments of the OLED of the present disclosure, at least one acceptor group G A Each of is independently selected from the group consisting of: 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.

[0181] In some embodiments of the OLED of the present disclosure, the first host is selected from the group consisting of:

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] 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.

[0188] In some embodiments, the organic layer may be an emissive layer and the compound as described herein may be an emissive dopant or a non-emissive dopant.

[0189] 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 ,OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 ), CH=CH-C n H 2n+1 、C≡CC n H 2n+1 ,Ar 1 ,Ar 1 -Ar 2 , C n H2n -Ar 1 or no substituent, wherein n is 1 to 10; and wherein Ar 1 with Ar 2 Independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole and heteroaromatic analogs thereof.

[0190] In some embodiments, the organic layer may further include a host, wherein the host includes at least one chemical group selected from the group consisting of triphenylene, carbazole, indolecarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolecarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene and aza-(5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene).

[0191] In some embodiments, the subject can be selected from the group of subjects consisting of:

[0192]

[0193]

[0194] and combinations thereof.

[0195] In some embodiments, the organic layer may further include a host, wherein the host includes a metal complex.

[0196] In some embodiments, the compound as described herein may be a sensitizer; wherein the device may further comprise a receptor; and wherein the receptor may be selected from the group consisting of: a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0197] In yet another aspect, an OLED of the present disclosure may further comprise an emissive region containing a compound as disclosed in the above compounds section of the present disclosure.

[0198] Also disclosed is an emission 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 Groups formed;

[0199] 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

[0200] 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, silane, 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 .

[0201] In some embodiments, at least one of the anode, cathode, or new layer disposed above the organic emission layer is used as an enhancement layer. The enhancement layer includes a plasmon material that exhibits a surface plasmon resonance, the plasmon 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 arranged to be no more than a threshold distance from the organic emission layer, 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 where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further includes an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer on the opposite side of the organic emission layer. In some embodiments, the outcoupling layer is disposed on the side of the emission layer opposite to the enhancement layer, but can still outcouple energy from the surface plasmon mode 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 may be incorporated to extract the energy into free space. In some embodiments, one or more intervening layers may be disposed between the enhancement layer and the outcoupling layer. Examples of intervening layers may be dielectric materials, including organic, inorganic, perovskite, oxides, and may include stacks and / or mixtures of these materials.

[0202] The enhancement layer changes the effective properties of the medium in which the emitter material resides, causing any or all of the following: reduced emissivity, changed emission line shape, variation in emission intensity with angle, changed emitter material stability, changed OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both sides produces an OLED device that utilizes any of the above effects. In addition to the specific functional layers described in the various OLED examples mentioned herein and shown in the figures, the OLED according to the present disclosure may also include any other functional layers commonly found in OLEDs.

[0203] 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 strictly distinguished from many other photonic structures, such as distributed Bragg reflectors (DBRs), because the medium should appear uniform in the propagation direction on the length scale of the light wavelength. Using terminology that can be understood by those skilled in the art: the dielectric constant of the metamaterial in the propagation direction can be described by the effective dielectric approximation. Plasmonic materials and metamaterials provide methods for controlling light propagation, which can enhance OLED performance in many ways.

[0204] In some embodiments, the enhancement layer is arranged as a planar layer. In other embodiments, the enhancement 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.

[0205] 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 is composed of a plurality of nanoparticles disposed above a material. In these embodiments, the 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 on the plurality of nanoparticles, changing the thickness of the enhancement layer, and / or changing the material of the enhancement layer. The plurality of nanoparticles of the device can be formed of at least one of: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layering of one or more materials, and / or a core of one type of material and 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 on them. In some embodiments, the outcoupling layer can be used to adjust the polarization of the emission. Changing the size and periodicity of the outcoupling layer can select the polarization type that is preferentially outcoupled to air. In some embodiments, the outcoupling layer also acts as an electrode of the device.

[0206] In yet another aspect, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED), the organic light-emitting device 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.

[0207] In some embodiments, the consumer product comprises an OLED having an anode; a cathode; and an organic emission layer disposed between the anode and the cathode, wherein the organic emission layer may comprise 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 Groups formed;

[0208] 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

[0209] Each R S11 , R S12 and R S13 independently represents zero substitution, monosubstitution, or up to the maximum allowed substitution on its associated ring;

[0210] Each L 1 -L 2 and L 3 -L 4 independently represent anionic bidentate ligands;

[0211] Where n is 1 or 2;

[0212] 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;

[0213] 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, thiol, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;

[0214] 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

[0215] The first host comprises at least one donor group G D , and at least one acceptor group G A .

[0216] 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 billboard, 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 camcorder, 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.

[0217] 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 light emission 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.

[0218] Several OLED materials and configurations are described in US Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

[0219] 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 time frame of less than 10 nanoseconds.

[0220] 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.

[0221] Figure 1 An organic light-emitting device 100 is shown. The figure is not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emission layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The 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 7,279,704, columns 6-10, which are incorporated by reference.

[0222] More examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is one doped with F at a molar ratio of 50:1. 4-TCNQ m-MTDATA, 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 in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes 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 entirety. 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.

[0223] 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 manufactured by depositing the layers in order. Because the most common OLED configuration has a cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to 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 .

[0224] Figure 1 and 2The simple layered structures described in are provided by way of non-limiting examples, and it should be understood 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 the layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than the specifically described materials may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it should be understood that a combination of materials may be used, such as a mixture of a host and a dopant, or more generally, a mixture. In addition, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, the OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, Figure 1 and 2 Multiple layers of said different organic materials.

[0225] Structures and materials not specifically described may also be used, such as OLEDs containing 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.

[0226] 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. Pat. Nos. 6,013,982 and 6,087,196, incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (as described in U.S. Pat. No. 6,337,102 to Forrest et al., incorporated by reference in their entirety), and deposition by organic vapor jet printing (OVJP) (as described in U.S. Pat. No. 7,431,968, incorporated by reference in their 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. Pat. 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 a 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 having 20 or more carbons may be used, and 3 to 20 carbons are a preferred range. Materials having asymmetric structures may have better solution processability than materials having symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0227] 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 exposure to harmful substances in an environment including moisture, steam and / or gas. The barrier layer can be deposited on a substrate, an electrode, under a substrate, an electrode, or beside a substrate, an electrode, or on any other part (including an edge) of the device. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques, and may include a composition having a single phase and a composition having multiple phases. Any suitable material or material combination may be used for the barrier layer. The barrier layer may be combined with an inorganic compound or an organic compound or both. A 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 No. PCT / US2009 / 042829, which are incorporated herein by reference in their entirety. In order to be considered a "mixture", the aforementioned polymeric material and non-polymeric material constituting the barrier layer should be deposited under the same reaction conditions and / or deposited simultaneously. The weight ratio of polymeric material to non-polymeric material can be in the range of 95:5 to 5:95. The polymeric material and non-polymeric material can be produced from the same precursor material. In one example, the mixture of polymeric material and non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0228] The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of electronic component modules (or units), which can be incorporated into a 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 module may optionally include driving electronic devices and / or power supplies. The device manufactured according to the embodiments of the present disclosure can be incorporated into a variety of consumer products, and the consumer products have one or more electronic component modules (or units) incorporated therein. A consumer product comprising an OLED is disclosed, and 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 a certain type of visual display. Some examples of 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 matrices and active matrices. 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).

[0229] More details regarding OLEDs and the definitions set forth above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0230] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can employ the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0231] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

[0232] 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.

[0233] In some embodiments, the compound can be an emitting dopant. In some embodiments, the compound can be emitted 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 one enantiomer. In some embodiments, the compound can be homogeneous (each ligand is the same). In some embodiments, the compound can be mixed (at least one ligand is different from the 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 is also true in the embodiments where the ligand coordinated to the metal can be connected to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Thus, where 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).

[0234] 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 excited complex 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 be in the range of 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.

[0235] According to another aspect, a formulation comprising a compound described herein is also disclosed.

[0236] The OLEDs disclosed herein may be incorporated into one or more of consumer products, electronic component modules, and lighting panels.The organic layer may be an emissive layer, and the compound may be an emissive dopant in some embodiments, while the compound may be a non-emissive dopant in other embodiments.

[0237] 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.

[0238] 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 supramolecules). As used herein, a "monovalent variant of a compound" refers to a portion that is identical to the compound but one hydrogen has been 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 more than one hydrogen has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of a supramolecule, the compounds of the present invention can also be incorporated into a supramolecular complex without covalent bonds.

[0239] D. Combinations of Compounds of the Disclosure with Other Materials

[0240] The materials described herein as being suitable for use in a particular layer in 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 easily consult the literature to identify other materials that can be used in combination.

[0241] a) Conductive dopants:

[0242] The charge transport layer can be doped with a conductivity dopant to substantially change its charge carrier density, which in turn will change its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductivity dopant, and an n-type conductivity dopant is used in the electron transport layer.

[0243] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with references disclosing those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.

[0244]

[0245] b)HIL / HTL:

[0246] 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; indolecarbazole derivatives; polymers containing fluorocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x; p-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile; metal complexes; and crosslinkable compounds.

[0247] Examples of aromatic amine derivatives for use in HIL or HTL include, but are not limited to, the following general structure:

[0248]

[0249] 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, pyridyl indole, 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 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.

[0250] In one aspect, Ar 1 To Ar 9 Independently selected from the group consisting of:

[0251]

[0252] 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.

[0253] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0254]

[0255] Where Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 is 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.

[0256] 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 + / Fc coupling has a minimum oxidation potential in solution of less than about 0.6 V.

[0257] 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 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. ,

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] c) EBL:

[0266] 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 produce substantially higher efficiency and / or longer lifetime than a similar device lacking a 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.

[0267] d) Subject:

[0268] 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 may be used as long as the triplet energy of the host is greater than the triplet energy of the dopant. Any host material may be used with any dopant as long as the triplet criterion is satisfied.

[0269] Examples of metal complexes used as hosts preferably have the following general formula:

[0270]

[0271] Where Met is a metal; (Y 103 -Y 104) is a bidentate ligand, Y 103 and Y 104 is 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.

[0272] In one aspect, the metal complex is:

[0273]

[0274] where (ON) is a bidentate ligand with a metal coordinated to O and N atoms.

[0275] In another aspect, Met is selected from Ir and Pt. In another aspect, (Y 103 -Y 104 ) is a carbene ligand.

[0276] 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, pyridyl indole, 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 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.

[0277] In one aspect, the subject compound contains at least one of the following groups in the molecule:

[0278]

[0279] 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 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.

[0280] 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,

[0281]

[0282]

[0283]

[0284]

[0285]

[0286] e) Other emitters:

[0287] 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 may 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.

[0288] 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, JP201310263, 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。、

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] f)HBL:

[0295] 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 than a similar device lacking a blocking layer. In addition, a blocking layer can be used to confine emission to a desired area 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.

[0296] In one aspect, the compounds used in HBL contain the same molecules or the same functional groups as used in the subjects described above.

[0297] In another aspect, the compound used in HBL contains at least one of the following groups in the molecule:

[0298] Where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0299] g)ETL:

[0300] 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.

[0301] In one aspect, the compound used in the ETL contains at least one of the following groups in the molecule:

[0302]

[0303] 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. Ar 1 To Ar 3has a similar definition to Ar mentioned above. k is an integer from 1 to 20. 101 To X 108 is selected from C (including CH) or N.

[0304] In another aspect, the metal complex used in the ETL contains (but is not limited to) the following general formula:

[0305]

[0306] 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.

[0307] 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 US2009018957. 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,

[0308]

[0309]

[0310]

[0311] h) Charge Generation Layer (CGL)

[0312] In a tandem or stacked OLED, the CGL plays a fundamental role in the performance and 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. The electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; then, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductivity dopants used in the transport layer.

[0313] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specific listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, etc., may 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.) may also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0314] 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, other materials and structures may be used to replace many materials and structures described herein without departing from the spirit of the present invention. The present invention as required may therefore include variations of 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.

[0315] E. Experimental Data

[0316]

[0317] 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) followed by methanol (3 x 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.

[0318] 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-pentanedione-k 2 O,O') iridium(III) (0.9 g, 56% yield).

[0319]

[0320] 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 bubbled 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 as a red solid. 2 O,O']iridium(III) (0.47 g, 42% yield).

[0321] Device Examples

[0322] All example devices were operated under high vacuum (<10 -7 Torr) thermal evaporation. The anode electrode is The cathode is made of indium tin oxide (ITO). Liq (8-hydroxyquinoline lithium), followed by All devices were immediately sealed in a nitrogen glove box (<1 ppm H 2 O and O 2 ) and a moisture absorber is incorporated into the package. The organic stack of the device example is composed of the following in sequence: starting from the ITO surface, as the hole injection layer (HIL) LG101 (purchased from LG Chem); as a hole transport layer (HTL) HTM; as an 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 (8-hydroxyquinoline lithium). Table 1 shows device layer thicknesses and materials.

[0323] Table 1. Device layer materials and thicknesses

[0324]

[0325] The chemical structures of the materials used in the device are shown below:

[0326]

[0327] After fabrication, the devices were tested for electroluminescence (EL) and current density-voltage-luminance (JVL) characteristics. For this purpose, each sample was subjected to a 2-channel Keysight B2902A SMU at 10 mA / cm 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 used at 10 mA / cm 2 The integrated photon count under the voltage is scanned from 0 to 200 mA / cm 2 The external quantum efficiency (EQE) of the device was calculated using total integrated photon counting. All results are summarized in Table 2.

[0328] Table 2.

[0329]

[0330] Table 2 is an overview of the performance of the electroluminescent devices. First, the device of the present invention having compound 1 as the emitter (device 1) exhibits a significantly narrower FWHM when each emitter is doped in the same host (device 1 relative to device 3, and device 2 relative to device 4). In general, the FWHM of phosphorescent emitter complexes is wide, such as the typical 57 or 60nm exhibited by the comparative devices (devices 3 and 4) having emitter compound 2. Achieving a narrow FWHM is a goal that has been pursued. 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 about 10nm smaller. In earlier OLED research work, narrowed line shapes have been slowly achieved on the nanoscale. Therefore, the 8nm and 11nm reductions seen here are significantly unexpected results. Secondly, when the same emitter is doped into different hosts (Device 1 relative to Device 2, and Device 3 relative to Device 4), the inventive device with Host 1 (Device 1) has demonstrated great 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 demonstrated similar improvements relative to Device 4. These improvement values ​​are higher than any values ​​attributable to experimental error, and the observed improvements are significant and unexpected. In summary, the inventive devices described herein with a particular type of emitter and host combination have demonstrated unexpected synergistic advantages over other similar emitter and host combinations.

Claims

1. An organic light emitting device (OLED), comprising: anode; cathode; and An organic emission layer disposed between the anode and the cathode, comprising: The first entity; and a first emitter; 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 where each R S11 , R S12 and R S13 independently represents zero substitution, mono-substitution or up to the maximum allowed substitution of 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 variants thereof, partially or fully deuterated variants 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, thiol, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; wherein 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 of 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 OLED 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 OLED according to claim 1, wherein the first emitter is 4. The OLED according to claim 1, wherein the first emitter is selected from the group consisting of: 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,SO 2 , CR e R f 、SiR e R f and GeR e R f ; Where each of R', R" 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, thiol, 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 OLED according to claim 3, wherein the ligand (L 1 -L 2 ) is selected from the group consisting of: wherein Y 1 to Y 10 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,SO 2 , 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 OLED according to claim 3, wherein the ligand (L 1 -L 2 ) is selected from the group consisting of: Based on structure 1, L 1 -L 2 -1-i: Based on structure 2 L 1 -L 2 -2-i: Based on structure 3 L 1 -L 2 -3-i: Based on structure 4 L 1 -L 2 -4-i: Based on structure 5 L 1 -L 2 -5-i: Based on structure 6 L 1 -L 2 -6-i: Based on structure 7 L 1 -L 2 -7-i: Based on structure 8, L 1 -L 2 -8-i: Based on structure 9 L 1 -L 2 -9-i: Based on structure 10 L 1 -L 2 -10-i: Based on structure 11, L 1 -L 2 -11-i: Based on structure 12, L 1 -L 2 -12-i: Based on structure 13, L 1 -L 2 -13-i: Based on structure 14 L 1 -L 2 -14-i: and L based on structure 15 1 -L 2 -15-i: Based on structure 16 L 1 -L 2 -16-i: Based on structure 17, L 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. An organic light emitting device (OLED), comprising: anode; cathode; and An organic emission layer disposed between the anode and the cathode, 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 Where L 1 -L 2 represents anionic bidentate ligand; Where n is 1 or 2; Wherein the ligand L A Select from the group consisting of: Based on structure A1, L A1 -k: Based on structure A2 A2 -k: Based on structure A3 A3 -k: Based on structure A4 L A4 -k: 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 OLED according to claim 7, wherein the first emitter is selected from the group consisting of those based on the general formula (L 1 -L 2 -m-i) 2 Ir(L An -k) of (L 1 -L 2 -1-1) 2 Ir(L A1 -1) to (L 1 -L 2 -17-810) 2 Ir(L A6 -600), where 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 OLED 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 OLED 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 OLED according to claim 4, wherein the ligand L B Select from the group consisting of: Based on structure B1, L B1 -h: Based on structure B2 B2 -h: Based on structure B3 B3 -h: Based on structure B4 L B4 -h: 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 OLED according to claim 4, 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 Cj , R 201 and R 202 Each is independently defined as follows: Where R D1 To R D246 Has the following structure:

13. The OLED according to claim 12, wherein the first emitter is selected from the group consisting of: based on the general formula (L Bp -h) 2 Ir(L Cj-I ) B1 -1) 2 Ir(L C1-I ) to (L B4 -1170) 2 Ir(L C1416-I ), and based on the general formula (L Bp -h) 2 Ir(L Cj-II ) B1 -1) 2 Ir(L C1-II ) to (L B4 -1170) 2 Ir(L C1416-II ); wherein p is an integer from 1 to 4, and h is an integer from 1 to 1170.

14. The OLED according to claim 1, wherein the donor group G D independently comprising at least one portion 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 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 OLED according to 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 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 OLED of claim 1, wherein the first host is selected from the group consisting of:

17. An emission layer, comprising: The first entity; and a first emitter; 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 variants thereof, partially or fully deuterated variants 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, thiol, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; 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; in The first body 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.

18. A consumer product comprising the organic light emitting device (OLED) according to any one of claims 1 to 16.

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