Organic electroluminescent materials and devices

Abstract

This application relates to organic electroluminescent materials and devices. An organometallic compound is provided, comprising a first ligand L selected from the group consisting of… A ...and. In ligand L... A Middle, Y 1 To Y 10 Each of the Rs is carbon or nitrogen; part B is a monocyclic or polycyclic fused ring structure containing 5-membered and / or 6-membered rings; any two Rs A and R B They can be fused or joined to form rings; X is selected from O, S, Se, or NR; each R A and R B It is independently hydrogen or a general substituent; at least one R, R A Or R B Is it deuterium or L? A The linking group between the ligand and another ligand, including a deuterated aromatic ring; and L A It coordinates with a metal M selected from Os, Pd, Pt, Ir, Cu, Ag, or Au; and the compound is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

Description

[0001] This application is a divisional application of the invention patent application filed on April 1, 2022, with application number 202210357161.0 and titled "Organic Electroluminescent Materials and Devices". CROSS REFERENCE TO RELATED APPLICATIONS

[0002] This application is a continuation-in-part of co-pending U.S. Patent Application No. 17 / 669,864, filed February 11, 2022, the entire contents of which are incorporated herein by reference. This application also claims priority under 35 USC § 119(e) to U.S. Provisional Application No. 63 / 170,864, filed April 5, 2021, and U.S. Provisional Application No. 63 / 271,594, filed October 25, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This 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 Technology

[0004] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly popular. Many of the materials used to manufacture these devices are relatively inexpensive, thus organic optoelectronic devices have the potential to offer a cost advantage over inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can offer performance advantages over conventional materials.

[0005] OLEDs utilize organic thin films that emit light when a voltage is applied to the device. OLEDs are becoming an increasingly popular technology for applications such as flat panel displays, lighting, and backlighting.

[0006] One application of phosphorescent emitting molecules is in full-color displays. Industry standards for such displays require pixels suited to emitting specific colors (called "saturated" colors). Specifically, these standards require pixels saturated with red, green, and blue light. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emission. The same technology can be used for OLEDs. White OLEDs can be single-emitting-layer (EML) devices or stacked structures. Color can be measured using the CIE coordinate system, well-known in the field. Summary of the Invention

[0007] In one aspect, this disclosure provides an organometallic compound comprising a first ligand L selected from the group consisting of... A :

[0008] , , , , , , , and In ligand L A middle:

[0009] Y 1 To Y 10 Each of them is independently selected from a group composed of carbon and nitrogen;

[0010] Part B is a monocyclic or polycyclic fused ring structure containing 5-membered and / or 6-membered carbon rings or heterocycles;

[0011] Each R A and R B It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0012] Any two adjacent R A and R B They can be fused or joined to form rings;

[0013] X is selected from the group consisting of O, S, Se, and NR;

[0014] Each R A and R B Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl and combinations thereof;

[0015] At least one R, R A Or R B Is it deuterium or L? A Linking groups between the ligand and another ligand, including a deuterated aromatic ring;

[0016] L A Coordinated with metal M selected from the group consisting of Os, Pd, Pt, Ir, Cu, Ag and Au;

[0017] L A It can bind to other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; and

[0018] The compound is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

[0019] In another aspect, this disclosure provides a formulation of the compounds disclosed herein.

[0020] In another aspect, this disclosure provides an OLED having an organic layer comprising a compound disclosed herein.

[0021] In another aspect, this disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of this disclosure. Attached Figure Description

[0022] FIG. 1 An organic light-emitting device is shown.

[0023] FIG. 2 An inverted organic light-emitting device without an independent electron transport layer is demonstrated. Detailed Implementation

[0024] A. Terminology

[0025] Unless otherwise specified, the following terms as used herein are defined as follows:

[0026] As used herein, the term "organic" includes both polymeric materials and small-molecule organic materials that can be used to manufacture organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecule" can actually be quite large. In some cases, small molecules can include repeating units. For example, using long-chain alkyl groups as substituents does not remove a molecule from the "small molecule" category. Small molecules can also be incorporated into polymers, for example, as side groups on the polymer backbone or as part of the backbone. Small molecules can also act as the core portion of dendritic polymers, which consist 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. Dendritic polymers can be "small molecules," and all dendritic polymers currently used in the OLED field are considered small molecules.

[0027] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "placed" "above" the second layer, the first layer is placed further away from the substrate. Unless specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "placed" "above" the anode.

[0028] As used herein, “solution-handleable” means capable of dissolving, dispersing or transporting in and / or depositing from a liquid medium in the form of a solution or suspension.

[0029] When a ligand is considered to directly contribute to the photosensitivity of the emissive material, the ligand may be referred to as "photosensitive." When a ligand is considered not to contribute to the photosensitivity of the emissive material, the ligand may be referred to as "auxiliary," but auxiliary ligands can alter the properties of photosensitizing ligands.

[0030] As used herein, and as will generally be understood by those skilled in the art, if the first energy level is closer to the vacuum level, then the first "Highest Occupied Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO) level is "greater than" or "higher than" the second HOMO or LUMO level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with the vacuum level at the top, the LUMO levels of a material are higher than the HOMO levels of the same material. A "higher" HOMO or LUMO level appears to be closer to the top of this diagram than a "lower" HOMO or LUMO level.

[0031] As used herein, and as will generally be understood by those skilled in the art, if the first work function has a higher absolute value, then the first work function is “greater” or “higher” than the second work function. This is because the work function is typically measured as a negative number relative to the vacuum level, meaning that the “higher” work function is more negative. On a conventional energy level diagram with the vacuum level at the top, the “higher” work function is illustrated as being farther from the vacuum level in the downward direction. Therefore, the definitions of HOMO and LUMO levels follow different rules than those for the work function.

[0032] The terms “halogen,” “halogen,” and “halogen group” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0033] The term "acyl" refers to the substituted carbonyl group (C(O)-R). s ).

[0034] The term "ester" refers to the substituted oxycarbonyl group (-OC(O)-R). s or -C(O)-OR s ) group.

[0035] The term "ether" refers to -OR s Group.

[0036] The terms "thio-" or "thioether" are used interchangeably and refer to -SR s Group.

[0037] The term "selenium-based" refers to -SeR s Group.

[0038] The term "sulfinyl" refers to -S(O)-R s Group.

[0039] The term "sulfonyl" refers to -SO2-R s Group.

[0040] The term "phosphin" refers to -P(R) s )3 groups, wherein each R s They can be the same or different.

[0041] The term "silyl" refers to -Si(R) s )3 groups, wherein each R s They can be the same or different.

[0042] The term "germanium alkyl" refers to -Ge(R) s )3 groups, wherein each R s They can be the same or different.

[0043] The term "boron-based" refers to -B(R) s )2 group or its Lewis adduct -B(R s )3 groups, of which R s They can be the same or different.

[0044] In each of the above, R s It can be hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferred R s Choose from the following groups: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0045] The term "alkyl" refers to and includes both straight-chain and branched alkyl groups. Preferred alkyl groups are those containing one to fifteen carbon atoms, and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. Additionally, the alkyl group may optionally be substituted.

[0046] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 12 cyclic carbon atoms, and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, the cycloalkyl group may optionally be substituted.

[0047] The terms "heteroalkyl" or "heterocyclic alkyl" refer to alkyl or cycloalkyl groups having at least one carbon atom substituted with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Additionally, the heteroalkyl or heterocyclic alkyl group may optionally be substituted.

[0048] The term "alkenyl" refers to and includes both straight-chain and branched alkenyl groups. An alkenyl group is essentially an alkyl group comprising at least one carbon-carbon double bond in an alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group comprising at least one carbon-carbon double bond in a cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group in which at least one carbon atom is replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Additionally, alkenyl, cycloalkenyl, or heteroalkenyl groups may optionally be substituted.

[0049] The term "alkynyl" refers to and includes both straight-chain and branched alkynyl groups. An alkynyl group is essentially an alkyl group comprising at least one carbon-carbon triple bond in an alkyl chain. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may optionally be substituted.

[0050] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group that has been substituted with an aryl group. Additionally, aralkyl groups may optionally be substituted.

[0051] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Aromatic heterocyclic groups are used interchangeably with heteroaryl groups. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 to 7 ring atoms, including at least one heteroatom, and include cyclic amines such as morpholino, piperidinyl, pyrrolyl, etc., and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Additionally, the heterocyclic group may be optionally substituted.

[0052] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. A polycyclic system may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group; for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Additionally, the aryl group may optionally be substituted.

[0053] The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems comprising at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many cases, O, S, or N are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Heteropolycyclic systems may have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is a heteroaryl group, and other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Heteropolycyclic aromatic ring systems may have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole-carbazole, pyridylindole, pyrrolo-dipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benziisoxazole, benzothiazole, quinoline, isoquinoline, zoline, quinazole Phosphorus, quinoxaline, naphthidine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, and selelenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazynylene, and their aza analogs. Additionally, the heteroaryl group may optionally be substituted.

[0054] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, as well as their respective aza analogs, are of particular interest.

[0055] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, ynyl, aralkyl, heterocycloyl, aryl, and heteroaryl are either unsubstituted or substituted independently by one or more general substituents.

[0056] In many cases, the substituents are generally selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenyl, sulfinyl, sulfonyl, phosphinyl, boronyl, and combinations thereof.

[0057] In some cases, preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, boronyl, and combinations thereof.

[0058] In some cases, more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boronyl, aryl, heteroaryl, thio, and combinations thereof.

[0059] In other cases, the most preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0060] The terms "substituted" and "substituted" refer to substituents other than H being bonded to the relevant position, such as carbon or nitrogen. For example, when R... 1 When representing a single substitution, then an R 1 It must not be H (i.e., substitution). Similarly, when R 1 When representing disubstituted substitution, then the two Rs 1 It must not be H. Similarly, when R... 1 When R represents zero or no substitution, 1 For example, it could be hydrogen with available valences in the ring atom, such as the carbon atom in benzene and the nitrogen atom in pyrrole, or simply none for ring atoms with fully saturated valences, such as the nitrogen atom in pyridine. The maximum possible number of substitutions in a ring structure will depend on the total number of available valences in the ring atoms.

[0061] As used herein, “combination thereof” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl groups can be combined to form haloalkyl substituents; and halogen, alkyl, and aryl groups can be combined to form haloaralkyl groups. In one instance, the term substitution includes a combination of two to four listed groups. In another instance, the term substitution includes a combination of two to three groups. In yet another instance, 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 containing up to forty atoms that are not hydrogen or deuterium, or combinations containing 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.

[0062] The term "aza" in the passages described herein, namely aza-dibenzofuran, aza-dibenzothiophene, etc., refers to the fact that one or more of the CH groups in the corresponding aromatic ring can be replaced by nitrogen atoms, for example and without any limitation. Azatribenzene encompasses dibenzo[ f, h Quinoxaline and dibenzo[ f, h Quinoline. Other nitrogen analogs of the aza-derived compounds described above will be readily apparent to those skilled in the art, and all such analogs are intended to be covered by the terminology set forth herein.

[0063] As used herein, “deuterium” refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Review) 2007, 46, 7744-65 (which are incorporated herein by reference in their entirety) describe efficient pathways for the deuteration of methylene hydrogen in benzylamine and the replacement of aromatic cyclic hydrogens with deuterium.

[0064] It should be understood that when a molecular fragment is described as a substituent or additionally linked to another part, its name can be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or linked fragments are considered equivalent.

[0065] In some cases, a pair of adjacent substituents may optionally join or fuse into a ring. Preferred rings are five-, six-, or seven-membered carbon rings or heterocycles, including both 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 may be adjacent to each other on the same ring, or on two neighboring rings having two closest available substituted positions (such as the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene), provided that a stable fused ring system can be formed.

[0066] B. Compounds disclosed herein

[0067] In one aspect, this disclosure provides an organometallic compound comprising a first ligand L selected from the group consisting of... A : , , , , , , , and In ligand L A middle:

[0068] Y 1 To Y 10 Each of them is independently selected from a group composed of carbon and nitrogen;

[0069] Part B is a monocyclic or polycyclic fused ring structure containing 5-membered and / or 6-membered carbon rings or heterocycles;

[0070] Each R A and R B It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0071] Any two adjacent R A and R B They can be fused or joined to form rings;

[0072] X is selected from the group consisting of O, S, Se, and NR;

[0073] R, R A and R B Each is independently hydrogen or a substituent selected from the group of substituents defined herein;

[0074] At least one R, R A Or R B Is it deuterium or L? A Linking groups between the ligand and another ligand, including a deuterated aromatic ring;

[0075] L A Coordinated with metal M selected from the group consisting of Os, Pd, Pt, Ir, Cu, Ag and Au;

[0076] L A It can bind to other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; and

[0077] The compound is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

[0078] In some embodiments, R, R A and R B Independently, it is hydrogen or a substituent selected from the group of preferred general substituents as defined herein. In some embodiments, R, R A and R B Independently, it is hydrogen or a substituent selected from the group consisting of more preferred general substituents as defined herein. In some embodiments, R, R A and R B Substituents that are independently hydrogen or selected from the group of most preferred general substituents as defined herein.

[0079] In some embodiments, at least one R A It is deuterium. In some embodiments, at least one R B It is deuterium. In some embodiments, R is deuterium.

[0080] In some embodiments, at least one R A It is in L A A linking group between the linking group and another ligand comprising a deuterated aromatic ring. In some such embodiments, the linking group comprises a deuterated benzene ring. In some such embodiments, the linking group comprises a partially deuterated aromatic ring. In some such embodiments, the linking group comprises a fully deuterated aromatic ring.

[0081] In some embodiments, at least one R B It is in L A A linking group between the linking group and another ligand comprising a deuterated aromatic ring. In some such embodiments, the linking group comprises a deuterated benzene ring. In some such embodiments, the linking group comprises a partially deuterated aromatic ring. In some such embodiments, the linking group comprises a fully deuterated aromatic ring.

[0082] In some embodiments, the linking group has NR' and R' is a partially deuterated phenyl group.

[0083] In some embodiments, the linking group has NR' and R' is a fully deuterated phenyl group.

[0084] In some embodiments, Y1 Or Y 2 At least one of them is bonded to deuterium.

[0085] In some embodiments, Y 3 To Y 10 At least one of them is bonded to deuterium.

[0086] In some embodiments, part B is a 5- or 6-membered aryl or heteroaryl ring.

[0087] In some embodiments, part B is selected from the group consisting of phenyl, furan, thiophene, selenophene, pyrrole, imidazole and imidazole-derived carbenes.

[0088] In some embodiments, ligand L A Select the group consisting of the structures listed in List 1 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0089] In some embodiments, ligand L A Select the group consisting of the structures listed in List 2 below: , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , and ;

[0090] Y is selected from the group consisting of O, S, Se, Te, and NR;

[0091] At least one R, R a1 R a2 R a3 R a4 R a5 R a6 R a7 R a8 R a9 R a10 Or R B Is it deuterium or L? A The linking group between the ligand and another ligand, including a deuterated aromatic ring; and

[0092] Where R a1 R a2 R a3 R a4 R a5 R a6 R a7 R a8 R a9 and R a10 Each is independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boronyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioyl, and combinations thereof.

[0093] In some embodiments, R in each structure a1 It is D (deuterium). In some embodiments, R in each structure a1 and R a2 All are D. In some embodiments, R in each structure a1 To R a8 It is D. In some embodiments, R in each structurea1 To R a10 It is D.

[0094] In some embodiments, ligand L A Choose freely L Ai-m The group consisting of, i It is an integer from 1 to 336, and m It is an integer from 1 to 60, where L Ai-1 To L Ai-60 Each of them has the structure listed in Listing 3:

[0095]

[0096]

[0097] For each L Ai R E G is defined in the following Listing 4:

[0098]

[0099]

[0101] Where R 1 To R 30 It has the structure shown in Listing 5 below:

[0102] , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0103] Among them G 1To G 72 It has the structure shown in Listing 6 below:

[0104] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0105] In some embodiments, the compound has the formula M(L) A ) p (L B ) q (L C ) r L B and L C Each is a bidentate ligand; and p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of the metal M.

[0106] In some embodiments, M is Ir, L B It is a substituted or unsubstituted phenylpyridine, and L C It is a substituted or unsubstituted acetylacetonate. In some embodiments, M is Ir and L B and L C It is a substituted or unsubstituted acetylacetonate.

[0107] In some embodiments, the compound has a composition selected from Ir(L) A 3. Ir(L) A (L) B )2、Ir(L A )2(L B ), Ir(L A )2(L C ) and Ir(L A (L) B (L) C The expression consisting of a group of ) and where L A L B and L C Each one is different from the others.

[0108] In some embodiments, the compound has the formula Pt(L) A (L) B ); and L A and L B They can be the same or different. In some such embodiments, L A and L B Connect to form a tetradentate ligand.

[0109] In some embodiments, L B and L C Each group is independently selected from the following groups, which are composed of the structures listed in List 7: , , , , , , , , , , , , , , , , , , , , , and ,

[0110] in:

[0111] T is chosen from the group consisting of B, Al, Ga, and In;

[0112] X 1 To X 13 Each of them is independently selected from a group composed of carbon and nitrogen;

[0113] Y' selects from the following groups: BR e BR e R f NR e PR e P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f and GeR e R f ;

[0114] R e and R f They can be fused or joined to form rings;

[0115] Each R a R b R c and R d Independently represent zero substitution, single substitution, or up to the maximum permissible number of substitutions in its associated loop;

[0116] R a1 Rb1 R c1 R d1 R a R b R c R d R e and R f Each of them is independently hydrogen or a substituent selected from the group of general substituents as defined herein; and

[0117] Any two adjacent R a R b R c R d R e and R f They can fused or joined to form rings or multidentate ligands.

[0118] In some embodiments, L B and L C Each group is independently selected from the following groups, which are composed of structures listed in List 8: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ,

[0119] in:

[0120] R a '、R b 'and R c Each can be used independently to indicate zero substitution, single substitution, or up to the maximum permissible substitution in its associated loop;

[0121] R N R a1 R b1 R c1 R a R b R c R N R a '、R b 'and R c Each of the substituents in ' is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and

[0122] Two adjacent R a '、R b 'and R c They can fused or joined to form rings or polydentate ligands.

[0123] In some embodiments, the compound may have the formula Ir(L A 3. Formula Ir(L) A (L) Bk )2. Equation Ir(L A )2(L Bk ), formula Ir(L A )2(L Cj-I ), formula Ir(L A )2(L Cj-II ), formula Ir(L A (L) Bk (L) Cj-I ), or Ir(L A (L) Bk (L) Cj-II ), where L A These are the ligands defined in this paper; each L Bk Defined in this document; and L Cj-I and L Cj-II Each is defined in this article.

[0124] In some embodiments, when the compound has the formula Ir(L) Ai-mAt 3 o'clock, i It is an integer from 1 to 336; m It is an integer from 1 to 60; and the compound is selected from Ir(L A1-1 )3 to Ir(L A336-60 Groups consisting of 3;

[0125] When the compound has the formula Ir(L) Ai-m (L) Bk At 2 o'clock, i It is an integer from 1 to 336; m It is an integer from 1 to 60; k It is an integer from 1 to 324; and the compound is selected from Ir(L A1-1 (L) B1 )2 to Ir(L A336-60 (L) B324 Groups consisting of 2;

[0126] When the compound has the formula Ir(L) Ai-m )2(L Bk )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; k It is an integer from 1 to 324; and the compound is selected from Ir(L A1-1 )2(L B1 ) to Ir(L A336-60 )2(L B324 A group consisting of )

[0127] When the compound has the formula Ir(L) Ai-m )2(L Cj-I )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; j It is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1 )2(L C1-I ) to Ir(L A336-60 ) (L C1416-I A group consisting of ) and

[0128] When the compound has the formula Ir(L) Ai-m )2(L Cj-II )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; j It is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1 )2(L C1-II ) to Ir(L A336-60 ) (L C1416-IIA group consisting of )

[0129] Each L Bk It has a structure defined by the following Listing 9:

[0130] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0131] Each L Cj-I With a based The structure; and

[0132] Each L Cj-II With a based The structure, where for L Cj-I and L Cj-II Each L in Cj R 201 and R 202 Each is defined independently by the following List 10:

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] Where R D1 To R D246 It has the structure shown in Listing 11:

[0143] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0144] In some embodiments, the compound has the formula Ir(L Ai-m (L) Bk )2 or Ir(L Ai-m )2(L Bk ), wherein the compounds are selected only from those having the following L Bk Group of compounds with one of the ligand structures: L B1 L B2 L B18 L B28 L B38L B108 L B118 L B122 L B124 L B126 L B128 L B130 L B32 L B134 L B136 L B138 L B140 L B142 L B144 L B156 L B58 L B160 L B162 L B164 L B168 L B172 L B175 L B204 L B206 L B214 L B216 L B218 L B220 L B222 L B231 L B233 L B235 L B237 L B240 L B242 L B244 L B246 L B248 L B250 L B252 L B254 L B256 L B258 L B260 L B262 L B263 L B264 L B265 L B266 L B267 L B268 L B269 and L B270 .

[0145] In some embodiments, the compound has the formula Ir(L Ai-m (L) Bk )2 or Ir(L Ai-m )2(L Bk ), wherein the compounds are selected only from those having the following L Bk Group of compounds with one of the ligand structures: L B1 L B2 L B18L B28 L B38 L B108 L B118 L B122 L B124 L B126 L B128 L B132 L B136 L B138 L B142 L B156 L B162 L B204 L B206 L B214 L B216 L B218 L B220 L B231 L B233 L B237 L B265 L B266 L B267 L B268 L B269 and L B270 .

[0146] In some embodiments, the compound has the formula Ir(L Ai-m )2(L Cj-I ) or Ir(L Ai-m )2(L Cj-II ), wherein the compounds are selected only from those having L Cj-I or L Cj-II The group of compounds consisting of ligands, the R corresponding to the ligands 201 and R 202 Defined as one of the following structures: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0147] In some embodiments, the compound has the formula Ir(L Ai-m )2(L Cj-I ) or Ir(L Ai-m )2(L Cj-II ), wherein the compounds are selected only from those having L Cj-I or L Cj-II The group of compounds consisting of ligands, the R corresponding to the ligands 201 and R 202 Defined as one of the following structures: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0148] In some embodiments, the compound has the formula Ir(L Ai-m )2(L Cj-I And the compounds are selected only from those having the following L Cj-I A group of compounds whose ligand structure is one of the following: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0149] In some embodiments, the compound is selected from the group consisting of the structures listed in List 12: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0150] In some embodiments, the compound has the structure of Formula II.

[0151] ,

[0152] in:

[0153] The ligand L specified by ring AB A Select the group consisting of free form I to form IX;

[0154] M 1 It is either Pd or Pt;

[0155] Each of parts E and F is independently a monocyclic or polycyclic fused ring structure containing a 5-membered and / or 6-membered carbon ring or heterocycle;

[0156] Z 1 and Z 2 Each of them is independently C or N;

[0157] K 1 and K 2 Each of the elements is independently selected from the group consisting of direct keys, O, and S, where K 1and K 2 At least one of them is a direct bond;

[0158] L 1 L 2 and L 3 Each of the following is independently selected from the group consisting of single bond, non-existent bond, O, Se, S, SO, SO2, C=O, C=CR'R", C=NR', CR'R", SiR'R", P(O)R', BR', and NR', where L exists. 1 and L 2 At least one of them;

[0159] X 3 and X 4 Each of them is independently C or N;

[0160] R E and R F Each can independently represent zero substitution, single substitution, or up to the maximum permissible substitution in its associated loop;

[0161] R'、R"、R E and R F Each of them is independently hydrogen or a substituent selected from the group of preferred general substituents as defined herein; and

[0162] Where chemically feasible, two substituents can join or fuse together to form a ring.

[0163] In some embodiments of Formula II, portions E and F are both 6-membered aromatic rings.

[0164] In some embodiments of Formula II, part of F is a 5- or 6-membered heteroaromatic ring.

[0165] In some embodiments of Formula II, L 1 It is O or CR'R".

[0166] In some embodiments of Formula II, Z 2 It is N and Z 1 It's C.

[0167] In some embodiments of Formula II, Z 2 It is C and Z 1 It is N.

[0168] In some embodiments of Formula II, L 2 It is a direct key.

[0169] In some embodiments of Formula II, L 2 It is NR'.

[0170] In some embodiments of Formula II, K1 and K 2 They are all direct keys.

[0171] In some embodiments of Formula II, X 3 and X 4 Each of them is C.

[0172] In some embodiments of Formula II, the compound is selected from the group consisting of:

[0173] , , , , , , , and ,

[0174] in:

[0175] The ligand L specified by ring AB A Select the group consisting of free form I to form IX;

[0176] R X and R Y Each is selected from the group consisting of: alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; and

[0177] R G Each time it appears, it is independently hydrogen or a substituent selected from the group of preferred general substituents as defined herein.

[0178] In some such embodiments, L 1 Contains a deuterium-substituted aromatic ring. In some such embodiments, L 1 It is NR', where R' is a deuterated aromatic ring.

[0179] In some such embodiments, L 3 Contains a deuterium-substituted aromatic ring. In some such embodiments, L 3 It is NR', where R' is a deuterated aromatic ring.

[0180] In some such embodiments, the deuterium-substituted aromatic ring is a benzene ring. In some such embodiments, the deuterium-substituted aromatic ring is partially deuterated. In some such embodiments, the deuterium-substituted aromatic ring is fully deuterated.

[0181] In some embodiments, the compound is selected from the group consisting of the structures listed in List 13: , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0182] In some embodiments, the first ligand L described herein A The compound may be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, the percentage of deuteration has its general meaning and includes the percentage of possible hydrogen atoms substituted by deuterium atoms (e.g., positions of hydrogen, deuterium, or halogen).

[0183] C. OLEDs and devices disclosed herein

[0184] In another aspect, this disclosure also provides an OLED device comprising a first organic layer containing compounds as disclosed in the above compound portion of this disclosure.

[0185] In some embodiments, the OLED includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode. The emitting layer includes a partially or fully deuterated organometallic dopant, wherein the organometallic dopant is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm. In some embodiments, the organometallic dopant is a dopant comprising a first ligand L as described herein. A Organometallic compounds.

[0186] In some embodiments, an OLED includes an anode, a cathode, and a first organic layer disposed between the anode and the cathode. The first organic layer may comprise an organometallic compound containing a first ligand L as described herein. A .

[0187] In some embodiments, the organic layer may be an emission layer and the compound as described herein may be an emission dopant or a non-emission dopant.

[0188] In some embodiments, the organic layer may further comprise a body comprising a triphenylene containing benzofused thiophene or benzofused furan, wherein any substituent in the body is a non-fused substituent independently selected from the group consisting of: C n H 2n+1 OC n H 2n+1 ,OAr1,N(C n H 2n+1 2. N(Ar1)(Ar2), CH=CH-C n H 2n+1 C≡CC n H 2n+1 Ar1, Ar1-Ar2, C n H 2n -Ar1 or unsubstituted, wherein n is 1 to 10; and wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole and their heteroaromatic analogs.

[0189] In some embodiments, the organic layer may further comprise a body comprising at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronana[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, and aza-(5,9-dioxa-13b-boronana[3,2,1-de]anthracene).

[0190] In some embodiments, the subject may be selected from the following group of subjects:

[0191] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , And its combination.

[0192] In some embodiments, the organic layer may further comprise a body, wherein the body comprises a metal complex.

[0193] In some embodiments, the compound as described herein may be a sensitizer; wherein the device may further include a receptor; and wherein the receptor may be selected from the group consisting of fluorescent emitters, delayed fluorescent emitters, and combinations thereof.

[0194] In another aspect, the OLED of this disclosure may also include an emission region containing compounds as disclosed in the above compound portion of this disclosure.

[0195] In some embodiments, the emission region may include a first ligand L as described herein. A Organometallic compounds.

[0196] In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emitter layer serves as a reinforcement layer. The reinforcement layer comprises a plasmonic material exhibiting surface plasmon resonance, which is nonradiatively coupled to the emitter material and transfers excited-state energy from the emitter material to the nonradiative mode of the surface plasmon polaritons. The reinforcement layer is positioned at a distance from the organic emitter layer not exceeding a threshold distance, wherein, due to the presence of the reinforcement layer, the emitter material has a total nonradiative decay rate constant and a total radiative decay rate constant, and the threshold distance is the position where the total nonradiative decay rate constant equals the total radiative decay rate constant. In some embodiments, the OLED further comprises an external coupling layer. In some embodiments, the external coupling layer is disposed on the reinforcement layer on the opposite side of the organic emitter layer. In some embodiments, the external coupling layer is disposed on the emitter layer on the side opposite to the reinforcement layer, but still externally couples energy from the surface plasmon polaritons of the reinforcement layer. The external coupling 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 modes of the device into other modes, such as, but not limited to, organic waveguide modes, substrate modes, or another waveguide mode. If energy is scattered into the non-free-space modes of the OLED, other external coupling schemes can be combined to extract the energy into free space. In some embodiments, one or more intermediary layers may be disposed between the enhancement layer and the external coupling layer. Examples of intermediary layers may be dielectric materials, including organic, inorganic, perovskite, and oxide materials, and may comprise stacks and / or mixtures of these materials.

[0197] The enhancement layer alters the effective properties of the medium in which the emitter material resides, thereby causing any or all of the following: reduced emissivity, altered emission profile, emission intensity varying with angle, altered emitter material stability, altered OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, anode side, or both sides produces an OLED device that utilizes any of the aforementioned effects. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, the OLED according to this disclosure may also include any other functional layers commonly found in OLEDs.

[0198] The reinforcing 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 include 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. Typically, metamaterials are media composed of different materials, wherein the overall effect of the medium differs from the sum of its material components. Specifically, we define an optically active metamaterial as a material that simultaneously possesses 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 orientations. Optically active metamaterials and hyperbolic metamaterials differ significantly from many other photonic structures, such as distributed Bragg reflectors (DBRs), because the medium should exhibit uniformity along the propagation direction over the long scale of the light wavelength. Using terminology understandable to those skilled in the art, the dielectric constant of the metamaterial along the propagation direction can be described by an effective dielectric approximation. Plasmon materials and metamaterials offer methods for controlling light propagation, which can enhance OLED performance in a variety of ways.

[0199] In some embodiments, the enhancement layer is configured as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features arranged periodically, quasi-periodicly, or randomly, or subwavelength-sized features arranged periodically, quasi-periodicly, or randomly. In some embodiments, the wavelength-sized features and subwavelength-sized features have sharp edges.

[0200] In some embodiments, the outer coupling layer is characterized by a wavelength size arranged periodically, quasi-periodicly, or randomly, or by a subwavelength size arranged periodically, quasi-periodicly, or randomly. In some embodiments, the outer coupling layer may be composed of a plurality of nanoparticles, and in other embodiments, the outer coupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, the outer coupling can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material or an additional layer disposed on the plurality of nanoparticles, changing the thickness of the reinforcing layer, and / or changing the material of the reinforcing layer. The plurality of nanoparticles of the device may be formed from at least one of the following: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stack or layering of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outer coupling 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 may have additional layers disposed on them. In some embodiments, the outer coupling layer can be used to tune the polarization of the emission. Changing the size and periodicity of the outer coupling layer can select the polarization type preferentially coupled to air. In some embodiments, the outer coupling layer also functions as an electrode of the device.

[0201] In another aspect, this disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise compounds as disclosed in the above compound section of this disclosure.

[0202] In some embodiments, the consumer product includes an OLED, the OLED including an anode, a cathode, and an emitting layer disposed between the anode and the cathode. The emitting layer includes a partially or fully deuterated organometallic dopant, wherein the organometallic dopant is capable of emitting a peak maximum wavelength (λ) at room temperature. max Light ≥ 700 nm. In some embodiments, the organometallic dopant is a dopant comprising a first ligand L as described herein. A Organometallic compounds.

[0203] In some embodiments, the consumer product includes an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer may include a first ligand L as described herein. AOrganometallic compounds.

[0204] In some embodiments, a consumer product may be one of the following: a flat panel display, a computer monitor, a medical monitor, a television set, a signboard, a light for internal or external lighting and / or signaling, a head-up display, a fully transparent 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 with a diagonal of less than 2 inches, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.

[0205] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to both the anode and cathode. When a current is applied, holes are injected into the anode and electrons into the organic layer from the cathode. The injected holes and electrons migrate toward their respective oppositely charged electrodes. When electrons and holes are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair with an excited energy state. When the exciton relaxes through a photoemission mechanism, light is emitted. In some cases, excitons may be localized on excimers or excited-state complexes. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0206] Certain OLED materials and configurations are described in U.S. Patents 5,844,363, 6,303,238 and 5,707,745, which are incorporated herein by reference in their entirety.

[0207] Early OLEDs used emitting molecules that emitted light from a single state (“fluorescence”), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated herein by reference in its entirety. Fluorescence emission typically occurs within timeframes of less than 10 nanoseconds.

[0208] Recently, OLEDs with emitting materials that emit light from the triplet state (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, Vol. 395, 151-154, 1998 (“Baldo-I”); and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Applied Physics Letters, Vol. 75, 3, 4-6 (1999) (“Baldo-II”), are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in columns 5-6 of U.S. Patent No. 7,279,704, which is incorporated herein by reference.

[0209] FIG. 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emission layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by sequentially depositing the layers. The properties and functions of these various layers and example materials are described in more detail in columns 6-10 of US 7,279,704, which is incorporated herein by reference.

[0210] Further examples of each of these layers are available. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein 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 herein 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 herein by reference in its entirety. Examples of cathodes, comprising composite cathodes having a thin layer of metal (e.g., Mg:Ag) having an overlying transparent, conductive, sputtered ITO layer, are disclosed in their entirety in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. Theories and uses 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 herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. Descriptions of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0211] FIG. 2 An inverted OLED 200 is shown. The device includes a substrate 210, a cathode 215, an emitter layer 220, a hole transport layer 225, and an anode 230. The device 200 can be fabricated by sequentially depositing these layers. Because the most common OLED configuration has a cathode disposed above the anode, and the device 200 has a cathode 215 disposed below the anode 230, the 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 the device 200. FIG. 2 Provide an example of how some layers can be omitted from the structure of device 100.

[0212] FIG. 1 and 2The simple layered structures described herein are provided by way of non-limiting examples, and it should be understood that embodiments of this disclosure can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the various layers described in different ways, or the layers can be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many examples provided herein describe various layers as comprising a single material, it should be understood that combinations of materials, such as mixtures of host and dopant, or more generally, mixtures, can be used. Furthermore, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emitter layer 220, and can be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, regarding FIG. 1 and 2 Multiple layers of the different organic materials mentioned above.

[0213] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) containing polymeric materials, as disclosed in, for example, U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. By another example, OLEDs with a single organic layer can be used. OLEDs can be stacked, for example as described in, for example, U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. OLED structures can deviate from... FIG. 1 and 2 The simple layered structure described herein. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the tabletop structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the recessed structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0214] Unless otherwise specified, any of the layers in the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet printing (as described in U.S. Patent Nos. 6,013,982 and 6,087,196, which are incorporated herein by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Patent No. 6,337,102 by Forrest et al., which are incorporated herein by reference in their entirety), and deposition via organic vapor jet printing (OVJP, also known as organic vapor jet deposition (OVJD)) (as described in U.S. Patent No. 7,431,968, which is incorporated herein by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably performed in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include patterning via mask deposition, cold soldering (as described in U.S. Patents 6,294,398 and 6,468,819, which are incorporated herein by reference in their entirety), and some of the methods associated with 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 suit a particular deposition method. For example, branched or unbranched substituents, preferably containing at least three carbons, such as alkyl and aryl groups, may be used in small molecules to enhance their solution handling ability. Substituents having 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Materials with asymmetric structures may have better solution handleability than materials with symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the solution handling ability of small molecules.

[0215] The device manufactured according to embodiments of this disclosure may optionally further include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage caused by exposure to harmful substances in an environment including moisture, vapor, and / or gases. The barrier layer may be deposited on, under, or adjacent to a substrate or electrode, or on any other part of the device, including edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed using a variety of known chemical vapor deposition techniques and may comprise compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may contain inorganic or organic compounds, or both. Preferred barrier layers comprise a mixture of polymeric and non-polymeric materials, as described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entirety. For the process to be considered a "mixture," the aforementioned polymeric and non-polymeric materials constituting the barrier layer should be deposited and / or deposited simultaneously under the same reaction conditions. The weight ratio of polymeric to non-polymeric materials can range from 95:5 to 5:95. The polymeric and non-polymeric materials can be produced from the same precursor material. In one example, the mixture of polymeric and non-polymeric materials is essentially composed of polymeric silicon and inorganic silicon.

[0216] The apparatus manufactured according to embodiments of this disclosure can be incorporated into a wide variety of electronic component modules (or units), which can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include displays, lighting devices (such as discrete light source devices or lighting panels), etc., which can be utilized by end-user product manufacturers. The electronic component module may optionally include driving electronics and / or a power supply. The apparatus manufactured according to embodiments of this disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. A consumer product incorporating an OLED is disclosed, wherein the OLED includes compounds of this disclosure in its organic layer. The consumer product should include any type of product containing one or more light sources and / or one or more of some type of visual display. Examples of the consumer products described include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external lighting and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple tiled displays, theater or stadium screens, phototherapy devices, and signage. Various control mechanisms, including passive and active matrices, can be used to control the devices manufactured according to this disclosure. Many of the devices are intended for use in temperature ranges 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).

[0217] Further details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0218] 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 utilize the materials and structures described herein. More generally, organic devices such as organic transistors can utilize the materials and structures described herein.

[0219] 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 including carbon nanotubes.

[0220] In some embodiments, the OLED further comprises a layer including a delayed phosphor emitter. In some embodiments, the OLED comprises an RGB pixel arrangement or a white pixel arrangement with a color filter. 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 with 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 with 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.

[0221] In some embodiments, the compound may be an emission dopant. In some embodiments, the compound may generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known 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 annihilation, or a combination of these processes. In some embodiments, the emission dopant may be a racemic mixture or may be enriched with one enantiomer. In some embodiments, the compound may be homogeneous (each ligand is identical). In some embodiments, the compound may be mixed (at least one ligand is different from the others). In some embodiments, when more than one ligand coordinated to a metal is present, the ligands may all be identical. In some other embodiments, at least one ligand is different from the others. In some embodiments, each ligand may be different from each other. This also applies in embodiments where a ligand coordinated to a metal may be linked to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Therefore, in the case where the coordinating ligands are linked together, in some embodiments all the ligands may be the same, and in some other embodiments at least one of the linking ligands may be different from (multiple) other ligands.

[0222] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, wherein one or more layers in the OLED contain acceptors in the form of one or more fluorescent and / or delayed-motion fluorescent emitters. In some embodiments, the compound can be used as a component of an excited-state 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 to emit energy or further transfer energy to the final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, emission can be generated by any one or all of the sensitizer, the acceptor, and the final emitter.

[0223] According to another aspect, a formulation comprising the compounds described herein is also disclosed.

[0224] The OLEDs disclosed herein can be incorporated into one or more consumer products, electronic component modules, and lighting panels. The organic layer can be an emission layer, and the compound can be an emission dopant in some embodiments, while in other embodiments it can be a non-emission dopant.

[0225] In another aspect of the invention, a formulation comprising the novel compounds disclosed herein is described. The formulation may include one or more components selected from the group consisting of: solvents, a host, hole injection materials, hole transport materials, electron blocking materials, hole blocking materials, and electron transport materials.

[0226] This disclosure covers any chemical structure comprising the novel compounds of this disclosure or their monovalent or multivalent variants. In other words, the compounds of the present invention or their monovalent or multivalent variants may be part of a larger chemical structure. Such chemical structures may be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also referred to as supermolecules). As used herein, a "monovalent variant of a compound" refers to a portion that is identical to the compound but in which one hydrogen has been removed and replaced by a bond to the remainder of the chemical structure. As used herein, a "multivalent variant of a compound" refers to a portion that is identical to the compound but in which more than one hydrogen has been removed and replaced by one or more bonds to the remainder of the chemical structure. In the case of supramolecular compounds, the compounds of the present invention may also be incorporated into supramolecular complexes without covalent bonds.

[0227] D. Combinations of the compounds disclosed herein with other materials

[0228] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the emission dopants disclosed herein can be used in combination with a wide variety of host layers, transport layers, blocking layers, injection layers, electrodes, and other possible layers. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0229] a) Conductive dopants:

[0230] Charge transport layers can be doped with conductive dopants to substantially alter their charge carrier density, which in turn changes their conductivity. Conductivity is increased by creating charge carriers in the matrix material and, depending on the type of dopant, can also achieve changes in the Fermi level of the semiconductor. Hole transport layers can be doped with p-type conductive dopants, while n-type conductive dopants are used in electron transport layers.

[0231] Non-limiting examples of conductive dopants that can be used in conjunction with the materials disclosed herein in OLEDs are illustrated in the following references: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047 and US2012146012.

[0232] , , ,

[0233] , ,

[0234] , , , ,

[0235] , , and .

[0236] b) HIL / HTL:

[0237] The hole injection / transport materials used in this disclosure are not particularly limited, and any compound may be used, provided that the compound is commonly used as a hole injection / transport material. Examples of materials include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indole-carbazole derivatives; polymers containing fluorinated hydrocarbons; polymers with conductive dopants; conductive polymers, such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; and metal oxide derivatives, such as MoO. x p-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylhexacarbonitrile; metal complexes; and crosslinkable compounds.

[0238] Examples of aromatic amine derivatives used for HIL or HTL include (but are not limited to) the following general structures:

[0239] , , , and .

[0240] Ar 1 To Ar 9Each of these is selected from: the group consisting of, for example, aromatic cyclic compounds such as: benzene, biphenyl, biphenylene, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azulene; and the group consisting of, for example, aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzene The group consisting of benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cycloline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthracene, acridine, phenazine, phenothiazine, phenoxazine, benzofuran-pyridine, furan-dipyridine, benzothiophene-pyridine, thiophene-dipyridine, benzoselene-pyridine, and selelene-dipyridine; and the group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. Each Ar may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0241] In one aspect, Ar 1 To Ar 9 Choose independently from the following groups:

[0242]

[0243] Where k is an integer from 1 to 20; X 101 To X 108 It is C (including CH) or N; Z 101 It is NAr 1 , O or S; Ar 1 It has the same functional groups as defined above.

[0244] Examples of metal complexes used in HIL or HTL include (but are not limited to) the following general formulas:

[0245]

[0246] Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y101 and Y 102 Independently selected from C, N, O, P, and S; L 101 It is an auxiliary ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k" is the maximum number of ligands that can be bound to the metal.

[0247] In one aspect, (Y) 101 -Y 102 (Y) is a 2-phenylpyridine derivative. In another aspect, (Y) 101 -Y 102 Met is a carbapenem ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In yet another aspect, the metal complex possesses properties compared to Fc. + The minimum oxidation potential in solution with / Fc coupling is less than about 0.6 V.

[0248] Non-limiting examples of HIL and HTL materials in OLEDs that can be used in combination with the materials disclosed herein are illustrated below, along with references to 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. ,

[0249] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0250] c) EBL:

[0251] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emitter layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, the blocking layer can be used to confine emission to a desired area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to vacuum level) and / or higher triplet energy compared to the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO and / or higher triplet energy compared to one or more of the bodies closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecules or the same functional groups as those used in one of the bodies described below.

[0252] d) Main body:

[0253] The light-emitting layer of the organic EL device disclosed herein preferably contains at least a metal complex as the light-emitting material, and may contain a host material using a metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used, as long as the triplet energy of the host is greater than the triplet energy of the dopant. Any host material can be used with any dopant, as long as the triplet criterion is satisfied.

[0254] Examples of metal complexes used as the host preferably have the following general formula:

[0255]

[0256] Where Met is a metal; (Y) 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 Independently selected from C, N, O, P, and S; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k' + k" is the maximum number of ligands that can be bound to the metal.

[0257] In one aspect, metal complexes are:

[0258]

[0259] (ON) is a bidentate ligand of a metal that coordinates with O and N atoms.

[0260] In the other case, Met is selected from Ir and Pt. In the other case, (Y 103 -Y 104 ) is a carbaene ligand.

[0261] In one aspect, the host compound contains at least one selected from the group consisting of, for example, aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azurite; and aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzene Imidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cycloline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthracene, acridine, phenazine, phenothiazine, phenoxazine, benzofuran-pyridine, furan-dipyridine, benzothiophene-pyridine, thiophene-dipyridine, benzoselene-pyridine, and selelene-dipyridine; and the group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. Each option in each group may be unsubstituted or may be substituted by substituents selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0262] In one aspect, the host compound contains at least one of the following groups in its molecule:

[0263] , , , , ,

[0264] , , , , , , , , , , , , and ,

[0265] Where R 101The group consisting of the following is selected: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof, and when it is aryl or heteroaryl, it has a definition similar to that of Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X 101 To X 108 Independently selected from C (including CH) or N. Z 101 and Z 102 Independently selected from NR 101 、O or S.

[0266] Non-limiting examples of material combinations disclosed herein used as host materials in OLEDs are illustrated below, along with references to 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,

[0267] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0268] e) Other emitters:

[0269] One or more other emitter dopants may be used in conjunction 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.

[0270] Non-limiting examples of emitter materials in OLEDs that can be used in conjunction with the material combinations disclosed herein are illustrated below, along with references to those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR201200 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。、

[0271] 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0272] f) HBL:

[0273] Hole blocking layers (HBLs) can be used to reduce the number of holes and / or excitons leaving the emitter layer. The presence of such blocking layers in a device can result in generally higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, blocking layers can be used to confine emission to a desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (farthest from vacuum level) and / or higher triplet energy compared to the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO and / or higher triplet energy compared to one or more of the bodies closest to the HBL interface.

[0274] In one aspect, the compounds used in HBL contain the same molecules or the same functional groups as those used in the subject described above.

[0275] In another aspect, the compounds used in HBL contain at least one of the following groups in their molecules:

[0276]

[0277] Where k is an integer from 1 to 20; L101 It is another ligand, and k' is an integer from 1 to 3.

[0278] g) ETL:

[0279] An electron transport layer (ETL) may comprise a material capable of transporting electrons. The ETL may be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used, provided it is typically used for electron transport.

[0280] In one aspect, the compounds used in ETL contain at least one of the following groups in their molecules:

[0281]

[0282]

[0283] Where R 101 The group consisting of the following is selected: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof, which, when aryl or heteroaryl, have a similar definition to Ar as described above. 1 To Ar 3 It has a similar definition to Ar mentioned above. k is an integer from 1 to 20. X 101 To X 108 Selected from C (including CH) or N.

[0284] In another aspect, the metal complexes used in ETL contain (but are not limited to) the following general formula:

[0285]

[0286] Wherein (ON) or (NN) are bidentate ligands of metals that coordinate with atoms O, N or N, N; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bonded to the metal.

[0287] Non-limiting examples of ETL materials that can be used in OLEDs with the material combinations disclosed herein are illustrated below, along with references to those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US20 10108990, US2011156017, US2011210320, US2012193612, US2012214993, US201401 4925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO20 07111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO201110 5373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

[0288] , , ,

[0289] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0290] h) Charge Generation Layer (CGL)

[0291] In tandem or stacked OLEDs, the conduction layer (CGL) plays a fundamental role in performance. It consists of an n-doped layer and a p-doped layer, respectively, for injecting electrons and holes. Electrons and holes are supplied by the CGL and the electrodes. Electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductive dopants used in the transport layer.

[0292] In any of the compounds mentioned above used in each layer of an OLED device, hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. Therefore, any specifically listed substituent, such as (but not limited to) methyl, phenyl, pyridyl, etc., can be in its undeuterated, partially deuterated, and fully deuterated form. Similarly, substituent classes (e.g., (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their undeuterated, partially deuterated, and fully deuterated forms.

[0293] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. For instance, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. The claimed invention may therefore include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that various theories regarding why the invention works are not intended to be limiting.

[0294] E. Experimental Data

[0295]

[0296] To a solution of 4-(benzo[b]selenobenzyl-2-yl)-10-(trifluoromethyl)benzo[g]quinazolin-2-d (1.093 g, 2.55 mmol), iridium(IX) dichloride hexahydrogenate (0.45 g, 1.276 mmol) was added. The mixture was purged with N2 for 20 min and heated overnight at 130 °C. After the reaction, the mixture was used directly in the next step without purification.

[0297]

[0298] 3,7-Diethylnonane-4,6-dione (0.677 g, 3.19 mmol), K₂CO₃ (0.441 g, 3.19 mmol), and THF (30 ml) were added to the reaction mixture. The mixture was stirred at room temperature for 4 days. The mixture was then cooled to room temperature. DCM was added and the mixture was filtered to remove the precipitate. The solvent in the filtrate was removed, and the residue was purified on a silica gel column to give 1 g (62%) of the product.

[0299] Examples 2-4 of the present invention and Comparative Example 1 were synthesized according to the same procedure.

[0300] , , , , , ,

[0301] Table 1. Overview of the photophysical properties of Examples 1-4 and Comparative Example 1 of the present invention measured in PMMA.

[0302]

[0303] Compare the PLQY normalization of Example 1.

[0304] Table 2. Overview of the photophysical properties of comparative examples 2-3 measured in PMMA.

[0305]

[0306] Compare the PLQY normalization of Example 2.

[0307] Near-infrared (NIR) OLEDs are inefficient because NIR emitters have low photoluminescence quantum yields (PLQY) due to the bandgap law (Englman R, Jortner J. Molecular Physics 1970, 18, 145). Structural modifications to NIR emitters to enhance PLQY can be used to improve NIR OLED efficiency. As shown in Table 1, Examples 1-4 of the present invention and Comparative Example 1 both exhibit NIR emission with a peak wavelength of approximately 790 nm. Compared to Comparative Example 1, the doping of deuterium into the ligands of Examples 1-4 of the present invention resulted in an enhancement of PLQY (1.07 × to 1.3 ×). These improvements exceed any value attributable to experimental error, and the observed improvements are significant. Previously, deuteration of emitters was primarily used to improve device lifetime but had no effect on efficiency. This is again demonstrated by the results in Table 2. Comparative Example 3 is a red emitter with a peak wavelength of 620 nm. However, compared to the non-deuterated derivative—Comparative Example 2—deuteration at similar positions did not improve its PLQY value. Therefore, the significant improvement in emission efficiency brought about by deuteration was indeed unexpected. The device performance below further confirms this improvement.

[0308] Device Examples

[0309] All example devices were subjected to high vacuum (<10) -7 The device was fabricated by thermal evaporation. The anode electrode was 1,150 Å indium tin oxide (ITO). The cathode consisted of 10 Å Liq (lithium 8-hydroxyquinoline) followed by 1,000 Å Al. All devices were immediately sealed after fabrication in a nitrogen glove box (<1 ppm H2O and O2) with epoxy-sealed glass covers and desiccant inside the packaging. The organic stack of the device example consisted, from the ITO surface, of the following: 100 Å HAT-CN as the hole injection layer (HIL); 400 Å HTM as the hole transport layer (HTL); 50 Å EBM as the electron blocking layer (EBL); 400 Å emitter layer (EML) containing a red host RH1 and 0.2% NIR emitter; 50 Å BM as the blocking layer (BL); and 350 Å Liq (lithium 8-hydroxyquinoline) doped with 35% ETM as the ETL. Table 3 shows the thickness and material of the device layers.

[0310] Table 3. Materials and Thickness of Device Layers

[0311]

[0312] The chemical structure of the materials used in the device is shown below:

[0313] and .

[0314] The manufactured device has undergone EL and JVL testing. For this purpose, the sample was tested using a 2-channel Keysight B2902ASMU at 10 mA / cm². 2 The current density was energized and measured using a Photo Research PR735 spectroradiometer. Radiometric intensity (W / str / cm²) was collected from 380 nm to 1080 nm. 2 ) and total integrated photon counting. The 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 counter converts the photodiode current into photon counts. The voltage is swept from 0 to 200 mA / cm². 2 The voltage was measured. The EQE of the device was calculated using the total integrated photon count. All results are summarized in Table 4.

[0315] Table 4. Results of the apparatus.

[0316]

[0317] Compare the EQE normalization of Example 1.

[0318] As is well known, due to the low photoluminescence quantum yield of NIR emitters, the efficiency of organic electroluminescent devices decreases as emission approaches λ. max The emission rate drops significantly in the near-infrared region (>700 nm). Table 4 summarizes the performance of the electroluminescent devices of the present invention devices 1-4 and Comparative Device 1. All devices exhibit near-infrared emission with a peak wavelength of approximately 797 nm. Due to the enhanced PLQY of the present invention examples 1-4, the present invention devices 1-4 exhibit higher EQE (1.07 × 1.2 × ...

Claims

1. An organometallic compound comprising a first ligand L selected from the group consisting of... A : , , , , , , , and ; in: Y 1 To Y 10 Each of them is independently selected from a group composed of carbon and nitrogen; Part B is a monocyclic or polycyclic fused ring structure containing 5-membered and / or 6-membered carbon rings or heterocycles; Each R A and R B It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution; Any two adjacent R A and R B They can be fused or joined to form rings; X is selected from the group consisting of O, S, Se, and NR; Each R, R A and R B Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl and combinations thereof; At least one R, R A Or R B Is it deuterium or L? A Linking groups between the ligand and another ligand, including a deuterated aromatic ring; L A Coordinated with metal M selected from the group consisting of Os, Pd, Pt, Ir, Cu, Ag and Au; L A It can bind to other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; and The compound is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

2. The compound according to claim 1, wherein each R, R A and R B It is hydrogen independently or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boronyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioyl and combinations thereof.

3. The compound according to claim 1, wherein at least one R A It is deuterium.

4. The compound according to claim 1, wherein at least one R B It is deuterium; and / or where R is deuterium; and / or where at least one R is deuterium. A It is in L A A linking group between the ligand and another ligand comprising a deuterated aromatic ring; and / or at least one of the R groups. B It is in L A A linking group between the ligand and another ligand comprising a deuterated aromatic ring; and / or wherein Y 1 Or Y 2 At least one of them is bonded to deuterium; and / or where Y 3 To Y 10 At least one of them is bonded to deuterium.

5. The compound according to claim 1, wherein part B is a 5- or 6-membered aryl or heteroaryl ring.

6. The compound according to claim 1, wherein the ligand L A Choose from the following groups: , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

7. The compound according to claim 1, wherein the ligand L A Choose from the following groups: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; Y is selected from the group consisting of O, S, Se, Te, and NR; At least one R, R a1 R a2 R a3 R a4 R a5 R a6 R a7 R a8 R a9 R a10 Or R B Is it deuterium or L? A The linking group between the ligand and another ligand, including a deuterated aromatic ring; and Where R a1 R a2 R a3 R a4 R a5 R a6 R a7 R a8 R a9 and R a10 Each is independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boronyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioyl, and combinations thereof.

8. The compound according to claim 7, wherein R in each structure a1 It is D; or R in each of its structures. a1 and R a2 All are D; or R in each of the structures. a1 To R a8 It is D; or R in each of its structures. a1 To R a10 It is D.

9. The compound according to claim 1, wherein the ligand L A Choose freely L Ai-m The group consisting of, i It is an integer from 1 to 336, and m It is an integer from 1 to 60. Where L Ai-1 To L Ai-60 It has the following structure: in, For each L Ai R E G is defined as follows: Where R 1 To R 30 It has the following structure: , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; Among them G 1 To G 72 It has the following structure: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and .

10. The compound according to claim 1, wherein the compound has the formula M(L) A ) p (L B ) q (L C ) r L B and L C Each is a bidentate ligand; and p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of the metal M.

11. The compound according to claim 10, wherein when M is Ir, L B It is a substituted or unsubstituted phenylpyridine, and L C It is a substituted or unsubstituted acetylacetonate; or wherein M is Ir and L is L B and L C It is a substituted or unsubstituted acetylacetonate.

12. The compound according to claim 9, wherein the compound has a composition selected from Ir(L A 3. Ir(L) A (L) B )2、Ir(L A )2(L B ), Ir(L A )2(L C ) and Ir(L A (L) B (L) C The expression consisting of a group of ) and where L A L B and L C Each of them is different from the others; or has the formula Pt(L) A (L) B ); and L A and L B They can be the same or different.

13. The compound according to claim 10, wherein L B and L C Each individual independently selects from the following groups: , , , , , , , , , , , , , , , , , , , , , and , in: T is selected from the group consisting of B, Al, Ga, and In; X 1 To X 13 Each of them is independently selected from a group composed of carbon and nitrogen; Y' selects from the following groups: BR e BR e R f NR e PR e P(O)R e ,O,S,Se,C=O,C=S,C=Se,C=NR e C=CR e R f S=O, SO2, CR e R f SiR e R f and GeR e R f ; R e and R f They can be fused or joined to form rings; Each R a R b R c and R d Independently represent zero substitution, single substitution, or up to the maximum permissible number of substitutions in its associated loop; R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, boronyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; general substituents as defined herein; and Any two adjacent R a R b R c R d R e and R f They can fused or joined to form rings or multidentate ligands.

14. The compound according to claim 12, wherein: When the compound has the formula Ir(L) Ai-m At 3 o'clock, i It is an integer from 1 to 336; m It is an integer from 1 to 60; and the compound is selected from Ir(L A1-1 )3 to Ir(L A336-60 Groups consisting of 3; When the compound has the formula Ir(L) Ai-m (L) Bk At 2 o'clock, i It is an integer from 1 to 336; m It is an integer from 1 to 60; k It is an integer from 1 to 324; and the compound is selected from Ir(L A1-1 (L) B1 )2 to Ir(L A336-60 (L) B324 Groups consisting of 2; When the compound has the formula Ir(L) Ai-m )2(L Bk )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; k It is an integer from 1 to 324; and the compound is selected from Ir(L A1-1 )2(L B1 ) to Ir(L A336-60 )2(L B324 A group consisting of ) When the compound has the formula Ir(L) Ai-m )2(L Cj-I )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; j It is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1 )2(L C1-I ) to Ir(L A336-60 )2(L C1416-I A group consisting of ) and When the compound has the formula Ir(L) Ai-m )2(L Cj-II )hour, i It is an integer from 1 to 336; m It is an integer from 1 to 60; j It is an integer from 1 to 1416; and the compound is selected from Ir(L A1-1 )2(L C1-II ) to Ir(L A336-60 )2(L C1416-II A group consisting of ) Each L Bk A structure defined as follows: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; Each L Cj-I With a based The structure; and Each L Cj-II With a based The structure, where for L Cj-I and L Cj-II Each L in Cj R 201 and R 202 Each is defined independently as follows: Where R D1 To R D246 It has the following structure: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

15. The compound of claim 12, wherein the compound is selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

16. The compound according to claim 10, wherein the compound has the following structure Formula II, , in: The ligand L specified by ring AB A Select the group consisting of free form I to form IX; M 1 It is either Pd or Pt; Each of parts E and F is independently a monocyclic or polycyclic fused ring structure containing a 5-membered and / or 6-membered carbon ring or heterocycle; Z 1 and Z 2 Each of them is independently C or N; K 1 and K 2 Each of the elements is independently selected from the group consisting of direct keys, O, and S, where K 1 and K 2 At least one of them is a direct bond; L 1 L 2 and L 3 Each of the following is independently selected from the group consisting of single bond, non-existent bond, O, Se, S, CR'R", SO, SO2, C=O, C=CR'R", C=NR', SiR'R", BR', P(O)R', and NR', where L exists. 1 and L 2 At least one of them; X 3 and X 4 Each of them is independently C or N; R E and R F Each can independently represent zero substitution, single substitution, or up to the maximum permissible substitution in its associated loop; R'、R"、R E and R F Each of these groups is independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boronyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioyl, and combinations thereof; and Where chemically feasible, two substituents can join or fuse together to form a ring.

17. An organic light-emitting device (OLED) comprising: anode; cathode; and An emission layer disposed between the anode and the cathode, wherein the emission layer comprises a partially or fully deuterated organometallic dopant, wherein the organometallic dopant is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

18. The OLED of claim 17, wherein the emitting layer further comprises a body, wherein the body comprises at least one chemical moiety selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronnaphthene[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, and aza-(5,9-dioxa-13b-boronnaphthene[3,2,1-de]anthracene).

19. The OLED of claim 18, wherein the body is selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , And its combination.

20. A consumer product comprising an organic light-emitting device, said organic light-emitting device comprising: anode; cathode; and An emission layer disposed between the anode and the cathode, wherein the emission layer comprises a partially or fully deuterated organometallic dopant, wherein the organometallic dopant is capable of emitting a peak wavelength (λ) at room temperature. max Light with a wavelength of ≥700 nm.

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