Organic electroluminescent materials and devices

Abstract

To provide novel organometallic complexes.SOLUTION: Provided are organometallic compounds comprising a first ligand LA represented by Formula I, where ring B is a 5-membered carbocyclic or heterocyclic ring; rings C and D are independently 5- or 6-membered carbocyclic or heterocyclic rings; and M is selected from among Os, Ir, Pd, Pt, Cu, Ag and Au. Also provided are compositions comprising these organometallic compounds, and OLEDs and related consumer products that utilize these organometallic compounds.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This application claims priority under Section 119(e) of the United States Patent Act to U.S. Provisional Application No. 63 / 117,727 filed 24 November 2020, U.S. Provisional Application No. 63 / 154,188 filed 26 February 2021, U.S. Provisional Application No. 63 / 168,419 filed 31 March 2021, and U.S. Provisional Application No. 63 / 192,228 filed 24 May 2021. The entire disclosures of these applications are incorporated herein by reference.

[0002] This disclosure generally relates to organometallic compounds and compositions, as well as various uses thereof, including light-emitting materials in devices such as organic light-emitting diodes and related electronic devices. [Background technology]

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

[0004] OLEDs utilize a thin organic film that emits light when a voltage is applied across the entire device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting, and backlighting.

[0005] One application of phosphorescent molecules is in full-color displays. Industry standards for such displays require pixels adapted to emit specific colors, known as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. Conventional liquid crystal displays emit light from a white backlight, which is filtered using absorption filters to produce red, green, and blue light. Similar techniques can be used with OLEDs. White OLEDs can be either single-layer emissive layer (EML) devices or stacked structures. Color can be measured using CIE coordinates, which are well known in the art. [Overview of the project]

[0006] Novel organometallic complexes containing five-membered heterocycles are disclosed. When these complexes are used as luminescent dopants for OLDE, they exhibit narrower emission compared to analogs with phenyl substituents. The narrow emission band of these complexes is due to slight geometric changes in the corresponding excited states. The predicted B peak height of these analogs is inversely proportional to the largest bond length change in each dopant, even if there are several other bond length changes in the molecule. The desired largest bond length change of these compounds in the excited state is less than 0.7 Å.

[0007] In one embodiment, the present disclosure relates to the first ligand L of the following formula I. A The present invention provides compounds containing the above. [ka] (In the formula, ring B is a 5-membered carbon ring or heteroring; Ring C and ring D are independently 5-membered or 6-membered carbon rings or heterorings; X 1 ~X 4 Exactly two of these are N atoms, bonded to each other, the remaining two are C atoms, and one C atom is bonded to ring D; K 3and K 4 is, independently of one another, a direct bond, O, or S, with at least one being a direct bond (the condition that "when K 3 is bonded to the N of ring A, it is a direct bond" is described in the specification); R A R B R C and R D each independently represents from mono to the maximum possible number of substitutions, or no substitution; R A R B R C and R D each independently is a substituent selected from the group consisting of hydrogen or a general substituent as defined herein; L A is coordinated to the metal M via two dashed lines; M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; L A can combine with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; Any two adjacent substituents can be bonded or condensed to each other to form a ring; Provided that L A [[ID=4O]]is not of the following formula II:

Chemical formula

[0008] In another aspect, the present disclosure provides a composition of a compound of formula I described herein.

[0009] In yet another aspect, the present disclosure provides an OLED having an organic layer containing a compound of formula I described herein.

[0010] In yet another aspect, the present disclosure provides a consumer product including an OLED having an organic layer containing a compound of formula I described herein.

Brief Description of the Drawings

[0011] [Figure 1] Figure 1 shows an organic light-emitting device.

[0012] [Figure 2] Figure 2 shows an inverted organic light-emitting device that does not have another electron transport layer.

[0013] [Figure 3] Figure 3 shows the photoluminescence spectrum of the compound of the present invention as disclosed herein. [Modes for carrying out the invention]

[0014] A. Terminology Unless otherwise specified, the following terms used in this specification are defined as follows:

[0015] As used herein, the term “organic” includes polymeric and low-molecular-weight organic materials that can be used to fabricate organic optoelectronic devices. “Low-molecular-weight” refers to any organic material that is not a polymer, and “low-molecular-weight” can actually be quite large. Low-molecular-weight may include repeating units in some contexts. For example, using long-chain alkyl groups as substituents does not exclude molecules from the “low-molecular-weight” class. Low-molecular-weight may be incorporated into polymers, for example, as pendant groups on a polymer backbone, or as part of said backbone. Low-molecular-weight may also serve as the core portion of a dendrimer, which consists of a series of chemical shells constructed on a core portion. The core portion of a dendrimer may be a fluorescent or phosphorescent low-molecular-weight emitter. Dendrimers can also be “low-molecular-weight,” and all dendrimers currently used in the field of OLEDs are considered to be low-molecular-weight.

[0016] In this specification, “top” means the part furthest from the substrate, while “bottom” means the part closest to the substrate. When it is stated that the first layer is “placed on top of” the second layer, the first layer is located further from the substrate. There may be other layers between the first and second layers unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “placed on top of” the anode, even if there are various organic layers in between.

[0017] As used herein, “solution processable” means that it can be dissolved, dispersed or transported in any liquid medium, either in solution or suspension form, and / or deposited from said medium.

[0018] A ligand may be referred to as "photoactive" if it is considered to directly contribute to the photoactive properties of the light-emitting material. A ligand may be referred to as "auxiliary" if it is not considered to contribute to the photoactive properties of the light-emitting material, although auxiliary ligands can alter the properties of photoactive ligands.

[0019] As used herein, as will be generally understood by those skilled in the art, the first “highest occupied molecular orbital” (HOMO) or “lowest empty molecular orbital” (LUMO) energy level is “greater than” or “higher than” the second HOMO or LUMO energy level, if the first energy level is close to the vacuum energy level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). In a conventional energy level diagram with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. “Higher” HOMO or LUMO energy levels appear to be closer to the top of such a diagram than “lower” HOMO or LUMO energy levels.

[0020] As used herein, as will be generally understood by those skilled in the art, if the first work function has a higher absolute value, then the first work function is "greater than" or "higher than" the second work function. Since work functions are generally measured as negative numbers relative to the vacuum level, this means that a "higher" work function is even more negative. In a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being far away from the vacuum level in the downward direction. Thus, the definitions of the HOMO and LUMO energy levels follow a different convention than that of the work function.

[0021] The terms "halo," "halogen," and "halide" are interchangeable and refer to fluorine, chlorine, bromine, and iodine.

[0022] The term "acyl" refers to a substituted carbonyl group (C(O)-R s ) refers to.

[0023] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR C(O)-OR s ) refers to the base.

[0024] The term "ether" is -OR s It refers to the base.

[0025] The terms "sulfanil" and "thioether" are used interchangeably, -SR s It refers to the base.

[0026] The term "selenyl" is SeR s It refers to the base.

[0027] The term "sulfinyl" is -S(O)-R s It refers to the base.

[0028] The term "sulfonyl" is -SO2-R s It refers to the base.

[0029] The term "phosphino" is -P(R s ) refers to 3 units, each R s They may be the same or different.

[0030] The term "silyl" is -Si(R s ) refers to 3 units, each R s They may be the same or different.

[0031] The term "Germil" is -Ge(R s ) refers to 3 units, each R s They may be the same or different.

[0032] The term "Boril" is -B(R s ) Two units, or their Lewis adducts-B(R s ) refers to 3 units, R s They may be the same or different.

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

[0034] The term "alkyl" refers to and includes both linear and branched alkyl groups. Preferred alkyl groups contain 1 to 15 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, and 2,2-dimethylpropyl. Furthermore, the alkyl groups may be optionally substituted.

[0035] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups contain 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, and adamantyl. Furthermore, the cycloalkyl groups may be optionally substituted.

[0036] The terms "heteroalkyl" and "heterocycloalkyl" refer, respectively, 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. Furthermore, the heteroalkyl group or heterocycloalkyl group may be optionally substituted.

[0037] The term "alkenyl" refers to and includes both linear and branched alkene groups. An alkenyl group is essentially an alkyl group containing at least one carbon-carbon double bond in the alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group containing at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom substituted 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 contain 2 to 15 carbon atoms. Furthermore, the alkenyl, cycloalkenyl, or heteroalkenyl groups may optionally be substituted.

[0038] The term "alkynyl" refers to and includes both linear and branched alkyne groups. An alkynyl group is essentially an alkyl group containing at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups contain 2 to 15 carbon atoms. Furthermore, the alkynyl group may be optionally substituted.

[0039] The terms "aralkyl" or "arylalkyl" are interchangeable and refer to alkyl groups substituted with aryl groups. Furthermore, the aralkyl groups may be optionally substituted.

[0040] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Heteroaromatic cyclic groups can be used interchangeably with heteroaryl groups. Preferred heterononaromatic cyclic groups contain 3 to 7 ring atoms, including at least one heteroatom, and include cyclic amines such as morpholino, piperidino, and pyrrolidino, and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, and tetrahydrothiophene. Furthermore, the heterocyclic group may optionally be substituted.

[0041] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. Polycyclic means having two or more rings in which two carbon atoms are shared between two adjacent rings (the rings are "condensed"), at least one of which is an aromatic hydrocarbyl group, and the other rings may be, for example, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups contain 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. Aryl groups with 6 carbon atoms, 10 carbon atoms, or 12 carbon atoms are particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene being preferred. Furthermore, the aryl groups may be optionally substituted.

[0042] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems containing at least one heteroatom. Examples of heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many examples, O, S, or N are preferred heteroatoms. A heteromonocyclic aromatic ring system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have 1 to 6 heteroatoms. A heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjacent rings (the rings are "condensed"), and at least one of the rings is a heteroaryl, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. A heteropolycyclic aromatic ring system may have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups contain 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiaidine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, and Examples include nzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzoflopyridine, phlodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, with dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azavolin, 1,3-azavolin, 1,4-azavolin, borazine, and aza-like compounds thereof. Furthermore, the heteroaryl group may be optionally substituted.

[0043] Of the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, as well as their respective aza-like analogs, are of particular interest.

[0044] The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted or independently substituted with one or more common substituents.

[0045] In many examples, the common substituents are selected from the group consisting of deuterium, halogens, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, gelmyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, selenyl, and combinations thereof.

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

[0047] In some examples, preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

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

[0049] The terms "substituted" and "substituted" refer to substituents other than H that are bonded to the relevant position (e.g., carbon or nitrogen). For example, R 1 If represents a mono-substitution, then one R 1 It must be something other than H (i.e., a substitution). Similarly, R 1 If R represents a di-substitution, 1 These two must be other than H. Similarly, R 1 If R represents zero or no substitution,1 This can be hydrogen in the available valence of a ring atom, such as the carbon atom in benzene and the nitrogen atom in pyrrole, or it simply represents nothing in the case of a ring atom with a fully filled valence (e.g., nitrogen in pyridine). The maximum number of possible substitutions in a ring structure depends on the total number of available valences in the ring atom.

[0050] Where used herein, “these combinations” means that one or more members of the applicable list are combined to form known or chemically stable configurations that can be conceived by those skilled in the art from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form an alkyl halide substituent; halogen, alkyl, and aryl can be combined to form an arylalkyl halide. In one example, the term substitution includes combinations of two to four of the listed groups. In another example, the term substitution includes combinations of two to three groups. In yet another example, the term substitution includes combinations of two groups. Preferred substitution combinations include those containing up to 50 atoms that are not hydrogen or deuterium, or up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium. In many examples, preferred substitution combinations include up to 20 atoms that are not hydrogen or deuterium.

[0051] In this specification, the name "aza" in fragments such as aza-dibenzofuran and aza-dibenzothiophene means that one or more CH groups in each aromatic ring can be replaced by nitrogen atoms. For example, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline, without limitation. Those skilled in the art will readily be able to imagine other nitrogen analogues of the aza derivatives described above, and all such analogues are intended to be encompassed by the terms used herein.

[0052] As used herein, “deuterium” refers to the isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, International Publication No. WO2006 / 095951, and U.S. Patent Application Publication No. 2011 / 0037057, whose entire contents are incorporated by reference, describe the preparation of deuterium-substituted organometallic complexes. Further references are made by Tetrahedron 2015, 71, 1425-30 (Ming Yan et al.) and Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65 (Atzrodt et al.), whose entire contents are incorporated by reference, describing efficient routes for deuterating methylene hydrogen in benzylamine and substituting aromatic ring hydrogens with deuterium, respectively.

[0053] When a molecular fragment is described as a substituent or as being attached to another part, it should be understood that its name may be written as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the whole molecule (e.g., benzene, naphthalene, dibenzofuran). In this specification, even if the substituent or attached fragment is described differently, these are considered equivalent.

[0054] In some examples, a pair of adjacent substituents can optionally bond or condense to form a ring. Preferred rings are five-membered, six-membered, or seven-membered carbocyclic or heterocyclic rings, including both cases where the portion of the ring formed by the pair of substituents is saturated and cases where the portion of the ring formed by the pair of substituents is unsaturated. As used herein, “adjacent” means that the two substituents in question can be adjacent to each other and on the same ring, or on two adjacent rings having two nearest available substitutable positions, such as positions 2 and 2' in biphenyl and positions 1 and 8 in naphthalene, as long as they can form a stable fused ring system.

[0055] B. Compounds of the present disclosure In one embodiment, the present disclosure relates to the first ligand L of the following formula I. A The present invention provides compounds containing the above. [ka] (In the formula, ring B is a 5-membered carbon ring or heteroring; Ring C and ring D are independently 5-membered or 6-membered carbon rings or heterorings; X 1 ~X 4 Exactly two of these are N atoms, bonded to each other, the remaining two are C atoms, and one C atom is bonded to ring D; K 3 and K 4 Each is independently a direct bond, O, or S, and at least one of them is a direct bond; R A , R B , R C , and R D Each of these independently represents up to the maximum number of possible substitutions from a thing, or no substitutions; R A , R B , R C , and R D Each of these substituents is independently selected from the group consisting of hydrogen or general substituents as defined herein; L A It coordinates to metal M via two dashed lines; M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; L A It can combine with other ligands to form tridentate, quadrdentate, quindentate, or hexadentate ligands; Any two adjacent substituents can bond to or condense with each other to form a ring; However, L A The following equation II: [ka] isn't it.)

[0056] In some embodiments, R A , R B , R C , and R D Each is independently selected from the group consisting of hydrogen, or deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

[0057] In some embodiments, K 3 When it bonds with N in ring A, it is a direct bond. In some embodiments, K 3 and K 4 All of these can be direct bonds. In some embodiments, K 4 It can be O.

[0058] In some embodiments, ring B is a five-membered carbon ring or a five-membered heteroring.

[0059] In some embodiments, ring B contains a heteroatom that is S, Se, or O. In some embodiments, the heteroatom is S. In some embodiments, the heteroatom is Se. In some embodiments, the heteroatom is O.

[0060] In some embodiments, ring B can be pyrrole, furan, or thiophene.

[0061] In some embodiments, X 2 and X 3 One of the elements is N and is bonded to each other, the remaining two are C, and one C is bonded to ring D. In some embodiments, X 1 and X 2One of the elements is N and is bonded to each other, the remaining two are C, and one C is bonded to ring D. In some embodiments, X 3 and X 4 One of the elements is N, and they are bonded to each other. The remaining two elements are C, and one of the C elements is bonded to ring D.

[0062] In some embodiments, ring C and ring D are each a 5-membered carbon ring or heteroring. In some embodiments, ring C and ring D are 5-membered carbon rings. In some embodiments, ring C and ring D are 5-membered heterorings. In some embodiments, ring C and ring D are each a 6-membered carbon ring or heteroring. In some embodiments, ring C and ring D are 6-membered carbon rings. In some embodiments, ring C and ring D are 6-membered heterorings.

[0063] In some embodiments, ring C is a five-membered carbon ring or heteroring. In some embodiments, ring C is a five-membered carbon ring. In some embodiments, ring C is a five-membered heteroring.

[0064] In some embodiments, ring C contains a heteroatom S. In some embodiments, ring C is a 5-membered carbon ring or heteroring, and ring D is a 6-membered carbon ring or heteroring. In some embodiments, ring C is a 6-membered carbon ring or heteroring. In some embodiments, ring C is a 6-membered carbon ring. In some embodiments, ring C is a 6-membered heteroring.

[0065] In some embodiments, ring C is a 6-membered carbon ring or heteroring, and ring D is a 5-membered carbon ring or heteroring.

[0066] In some embodiments, ring C and ring D can be independently benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, or thiazole.

[0067] In some embodiments, two adjacent Rs C are joined or fused to each other to form a ring.

[0068] In some embodiments, two adjacent Rs D are joined or fused to each other to form a ring. In some embodiments, the fused ring is naphthalene, benzofuran, benzothiophene, benzoselenophene, indene, indole, dibenzofuran, dibenzothiophene, dibenzoselenophene, fluorene, carbazole, or an aza-variant thereof.

[0069] In some embodiments, ligand L A is selected from the group consisting of:

Chem.

Chem.

[0070] In some embodiments, ligand L A is selected from the group consisting of the structures in LIST1 below.

Chem.

Chem.

Chem.

[0071] In some embodiments, the compound can have the formula Ir(L A )3, the formula Ir(L A )(L Bk )2, the formula Ir(L A )2(L Bk ), the formula Ir(L A )2(L Cj-I ), the formula Ir(L A )2(L Cj-II ), the formula Ir(L A )(L Bk )(L Cj-I ), or the formula Ir(L A )(L Bk )(L Cj-II ), wherein L A is a ligand having the structure of formula I as defined herein; L Bk is as defined herein; L Cj-I and L Cj-II each are as defined herein.

[0072] In some embodiments, the ligand L A is selected from the group consisting of L Ai-m-X , wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, X is from 1 to 4, 1 for O, 2 for S, 3 for Se, 4 for NCH3, L Ai-1-X to LAi-26-X Each of them has the structure shown in LIST2 below. [ka] JPEG0007879678000011.jpg127154In formula, L A1 ~L A1200 In each case, R E , R F And G are defined in LIST3 below. [Table 1] JPEG0007879678000013.jpg216143JPEG0007879678000014.jpg216143JPEG0007879678000015.jp g216143JPEG0007879678000016.jpg218144JPEG0007879678000017.jpg218143JPEG000787967800 0018.jpg219144JPEG0007879678000019.jpg219144JPEG0007879678000020.jpg218142JPEG00078 79678000021.jpg218144JPEG0007879678000022.jpg219144JPEG0007879678000023.jpg59142In formula, R 1 ~R 40 It has the structure defined in LIST4 below. [ka] In the formula, G 1 ~G 25 It has the structure shown in LIST5 below. [ka]

[0073] In some embodiments, the compound is of formula M(L A ) p (L B ) q (LC ) r It has, in the formula, L B and L C A, b, and r are each bidentate ligands; 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 metal M. In some embodiments of the compound, L B L is saturated or unsaturated phenylpyridine. C These are saturated or unsaturated acetylacetonates.

[0074] In some embodiments, the compound is 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 It has an expression selected from the group consisting of; L A , L B , and L C They are different from each other.

[0075] In some embodiments, L B and L C These can be independently selected from the following group: [ka] JPEG0007879678000027.jpg185154JPEG0007879678000028.jpg47122In formula, T is selected from the group consisting of B, Al, Ga, and In; Y 1 ~Y 13 Each is independently selected from the group consisting of carbon and nitrogen; Y' is BR e , NR e PR e , O, S, Se, C=O, S=O, SO2, CR e Rf 、SiR e R f 、and GeR e R f selected from the group consisting of; R e and R f can condense or combine to form a ring; R a 、R b 、R c 、and R d each independently represents zero, mono, or up to the maximum number of possible substitutions for the associated ring; R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e 、and R f each independently is hydrogen, or deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and a substituent selected from the group consisting of common substituents defined herein; Any two adjacent R a 、R b 、R c 、R d 、R e 、and R f can condense or combine to form a ring or a multidentate ligand.

[0076] In some embodiments, L B and L C can each independently be selected from the group consisting of.

Chemical formula

[0077] In some embodiments of the above compound, The aforementioned compound is of the formula Ir(L Ai-m-X When the compound has )3 (wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, and X is an integer from 1 to 4), the compound is Ir(L A1-1-1 )3~Ir(L A1200-26-4 Selected from a group consisting of 3; The aforementioned compound is of the formula Ir(L Ai-m-X )(L Bk When the compound has )2 (wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, X is an integer from 1 to 4, and k is an integer from 1 to 324), the compound is Ir(L A1-1-1 )(L B1 )2~Ir(LA1200-26-4 )(L B324 Selected from the group consisting of )2; The aforementioned compound is of the formula Ir(L Ai-m-X )2(L Bk When the compound has (wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, X is an integer from 1 to 4, and k is an integer from 1 to 324), the compound is Ir(L A1-1-1 )2(L B1 )~Ir(L A1200-26-4 )2(L B324 Selected from the group consisting of; The aforementioned compound is of the formula Ir(L Ai-m-X )2(L Cj-I When the compound has (wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, X is an integer from 1 to 4, and j is an integer from 1 to 1416), the compound is Ir(L A1-1-1 )2(L C1-I )~Ir(L A1200-26-4 )2(L C1416-I Selected from the group consisting of; The aforementioned compound is of the formula Ir(L Ai-m-X )2(L Cj-II When the compound has (wherein i is an integer from 1 to 1200, m is an integer from 1 to 26, X is an integer from 1 to 4, and j is an integer from 1 to 1416), the compound is Ir(L A1-1-1 )2(L C1-II )~Ir(L A1200-26-4 )2(L C1416-II Selected from the group consisting of; L Ai-m-X The structure is as defined in LIST2 above; Each L Bk It has the structure defined in LIST6 below. [ka] JPEG0007879678000033.jpg212154JPEG0007879678000034.jpg180154JPEG0007879678000035.jp g209154JPEG0007879678000036.jpg165154JPEG0007879678000037.jpg174154JPEG0007879678000 038.jpg190154JPEG0007879678000039.jpg200154JPEG0007879678000040.jpg201154JPEG0007879 678000041.jpg174154JPEG0007879678000042.jpg185154JPEG0007879678000043.jpg186154In the formula, each L Cj-I The formula is: [ka] It has a structure based on; each L Cj-II The formula is: [ka] It has a structure based on the formula, where L Cj-I and L Cj-II Each L in Cj In R 201 and R 202 Each of these is defined independently, as shown in LIST7 below. [Table 2] JPEG0007879678000047.jpg211154JPEG0007879678000048.jpg212154JPEG0007879678000049.jp g211154JPEG0007879678000050.jpg212154JPEG0007879678000051.jpg212154JPEG000787967800 0052.jpg212154JPEG0007879678000053.jpg212154JPEG0007879678000054.jpg212154JPEG00078 79678000055.jpg211154JPEG0007879678000056.jpg212154JPEG0007879678000057.jpg53154In formula, R D1 ~R D246 It has the structure defined in LIST8 below. [ka] JPEG0007879678000059.jpg206154JPEG0007879678000060.jpg203154JPEG0007879678000061.jpg186154JPEG0007879678000062.jpg54154

[0078] In some embodiments of the above compound, the compound is Ir(L Ai-m )(L Bk )2 or Ir(L Ai-m )2(L Bk ) has the following L Bk Ligand:L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B32 , L B134 , L B136 , L B138 , L B140 , LB142 , 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 The compound is selected from the group consisting only of compounds having one of the following:

[0079] In some embodiments of the above compound, the compound is of the formula Ir(L Ai-m )(L Bk )2 or Ir(L Ai-m )2(L Bk ) has the following L Bk Ligand:L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B132 , L B136, L B138 , L B142 , L B156 , L B162 , L B204 , L B206 , L B214 , L B216 , L B218 , L B220 , L B231 , L B233 , L B237、 L B265 , L B266 , L B267 , L B268 , L B269 , and L B270 The compound is selected from the group consisting only of compounds having one of the following:

[0080] In some embodiments of the above compound, the compound is of the formula Ir(L Ai-m )2(L Cj-I ) or Ir(L Ai-m )2(L Cj-II ) has the corresponding R 201 and R 202 However, the following structure: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D18 , R D20 , R D22 , R D37 , R D40 , R D41 , R D42 , R D43 , R D48 , R D49 , R D50 , R D54 , R D55 , R D58 , R D59 , R D78 , R D79 , R D81 , R D87 , R D88 , R D89 , R D93 , R D116 , R D117 , R D118 , R D119, R D120 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D147 , R D149 , R D151 , R D154 , R D155 , R D161 , R D175 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 , and R D246 L is defined as one of the following. Cj-I or L Cj-II The compounds are selected from the group consisting only of compounds having ligands.

[0081] In some embodiments, the compound is of the formula Ir(L Ai-m )2(L Cj-I ) or Ir(L Ai-m )2(L Cj-II ) has the corresponding R 201 and R 202 However, the following structure: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D17 , R D22 , R D43 , R D50 , R D78 , R D116 , R D118 , R D133 , R D134 , RD135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D149 , R D151 , R D154 , R D155 , R D190 , R D193 , R D200 , R D201 , R D206 , R D210 , R D214 , R D215 , R D216 , R D218 , R D219 , R D220 , R D227 , R D237 , R D241 , R D242 , R D245 , and R D246 L is defined as one of the following. Cj-I or L Cj-II The compounds are selected from the group consisting only of compounds having ligands.

[0082] In some embodiments, the compound is of the formula Ir(L Ai-m )2(L Cj-I ) has, and the compound is L Cj-I The ligand is selected from the group consisting only of compounds having one of the structures listed in LIST9 below. [ka] JPEG0007879678000064.jpg61154

[0083] In some embodiments, the compound is selected from the group consisting of the structures in LIST10 below. [ka] JPEG0007879678000066.jpg185154

[0084] In some embodiments, the compound is given by the following formula III: [ka] During the ceremony, M 1 is either Pd or Pt; Parts E and F are, independently, monocyclic or polycyclic ring structures containing 5-membered and / or 6-membered carbon rings or heterocyclic rings; Z 1 and Z 2 Each of these is independently either C or N; K 1 , K 2 , K 3 , and K 4 Each of these is independently selected from the group consisting of direct bonds, O, and S, of which at least two are direct bonds; L 1 , L 2 , and L 3 Each is independently selected from the group consisting of single bond, no bond, O, S, SO, SO2, C=O, C=NR', C=CR'R'', CR'R'', SiR'R'', BR', and NR', L 1 and L 2 At least one of them exists; R E and R F Each independently represents zero, mono, or the maximum number of possible permutations on the associated ring; R', R'', R E , and R F Each of these substituents is independently selected from the group consisting of hydrogen, or deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, gelmyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; Two adjacent R A , R B , R C , R E , and R FThese can bond or condense with each other to form chemically possible rings; X 1 ~X 4 , R A , R B , R C , and ring C all have the same definition as described above.

[0085] In some embodiments of the compound of formula III, both part E and part F are six-membered aromatic rings. In some embodiments, part F is a five-membered or six-membered heteroaromatic ring.

[0086] In some embodiments of the compound of formula III, L 1 is O or CR'R''. In some embodiments, Z 2 is N, Z 1 is C. In some embodiments, Z 2 is C, Z 1 is N. In some embodiments, L 2 This is a direct bond. In some embodiments, L 2 is NR'. In some embodiments, K 1 , K 2 , K 3 , and K 4 These are all direct bonds. In some embodiments, K 1 , K 2 , K 3 , and K 4 One of them is O.

[0087] In some embodiments, the compound is of the formula Pt(L A’ Selected from the group consisting of compounds having )(Ly). [ka] In the formula, L A’ The structure is selected from the group consisting of the structures in LIST11 below. [ka] JPEG0007879678000070.jpg186154JPEG0007879678000071.jpg123154In formula, Y 3 and Y 4 These are, independently, O, S, Se, or NCH3; R C1 and R D1 Each represents up to the maximum number of possible substitutions from the object, or no substitutions; R A1 , R C1 , R C2 , and R D1 Each is independently a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, gelmyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof; L 1 This is the same as the definition above; L y The structure is selected from the group consisting of the structures in LIST12 below. [ka] JPEG0007879678000073.jpg76154In formula, R F1 and R E1 Each represents up to the maximum number of possible substitutions from the object, or no substitutions; R F1 , R E1 , and R E2Each of these substituents is independently selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, gelmyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof.

[0088] In some embodiments, the compound is expressed by the following formula Pt(L A’ Selected from the group consisting of compounds having )(Ly). [ka] In the formula, L A’ The following structural formulas are selected from the group shown below, where H, I, and J are each an integer between 1 and 40, and A and B are each an integer between 1 and 4. [ka] JPEG0007879678000076.jpg179154In formula, L y The set is selected from the group consisting of the structures shown in LIST13 below, where K, L, M, and N are each an integer between 1 and 40, and C and D are each an integer between 1 and 4. [ka] JPEG0007879678000078.jpg221154JPEG0007879678000079.jpg43154In formula, R 1 ~R 40 It has the structure defined in LIST4 in this specification, Y 1 is O, Y 2 S is Y 3 Se is Y 4 It is NCH3.

[0089] In some embodiments, the compound is selected from the group consisting of the following: [ka] JPEG0007879678000081.jpg28154

[0090] In some embodiments, the first ligand L of formula I described herein A Compounds having can be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. In this specification, the deuterated percentage (%) has its usual meaning and includes the percentage (e.g., the position of hydrogen or deuterium) of hydrogen atoms that can be substituted by deuterium atoms.

[0091] C. OLEDs and devices of this disclosure In another embodiment, the Disclosure also provides an OLED device comprising a first organic layer containing a compound disclosed in the aforementioned Compounds section of the Disclosure.

[0092] In some embodiments, the OLED includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a first ligand L of the following formula I. A It contains compounds that include [specific compounds]. [ka] (In the formula, ring B is a 5-membered carbon ring or heteroring; Ring C and ring D are independently 5-membered or 6-membered carbon rings or heterorings; X 1 ~X 4Exactly two of these are N atoms, bonded to each other, the remaining two are C atoms, and one C atom is bonded to ring D; K 3 and K 4 Each is independently a direct bond, O, or S, and at least one of them is a direct bond; R A , R B , R C , and R D Each of these independently represents up to the maximum number of possible substitutions from a thing, or no substitutions; R A , R B , R C , and R D Each of these substituents is independently selected from the group consisting of hydrogen or general substituents as defined herein; L A It coordinates to metal M via two dashed lines; M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; L A It can combine with other ligands to form tridentate, quadrdentate, quindentate, or hexadentate ligands; Any two adjacent substituents can bond to or condense with each other to form a ring; However, L A The following equation II: [ka] isn't it.)

[0093] In some embodiments of the OLED, the compound is a sensitizer, and the OLED further comprises an acceptor selected from a fluorescent emitter, a delayed fluorescent emitter, and a combination thereof.

[0094] In some embodiments, the organic layer may be a light-emitting layer, and the compounds described herein may be light-emitting dopants or non-light-emitting dopants.

[0095] In some embodiments, the organic layer may further include a host, the host comprising a triphenylene containing a benzo-condensed thiophene or a benzo-condensed furan, and any substituent in the host independently being 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 is a non-condensed substituent selected from the group consisting of Ar1, and can be unsubstituted, with n being 1 to 10, and Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and their heteroaromatic analogs.

[0096] In some embodiments, the organic layer may further include a host, the host comprising at least one chemical moiety selected from the group consisting of naphthalene, fluorene, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-naphthalene, aza-fluorene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0097] In some embodiments, the host can be selected from the group consisting of the following host structures. [ka] JPEG0007879678000085.jpg213156JPEG0007879678000086.jpg155156

[0098] In some embodiments, the organic layer may further include a host, the host of which includes a metal complex.

[0099] In some embodiments, the compounds described herein may be sensitizers, and the device may further include an acceptor, the acceptor may be selected from a fluorescent emitter, a delayed fluorescent emitter, and a combination thereof.

[0100] In yet another embodiment, the OLED of the present disclosure may also include a light-emitting region comprising a compound disclosed in the aforementioned compound section of the present disclosure.

[0101] In some embodiments, the light-emitting region is formed by the first ligand L of the following formula I. A It may contain compounds that include the following: [ka] (In the formula, ring B is a 5-membered carbon ring or heteroring; Ring C and ring D are independently 5-membered or 6-membered carbon rings or heterorings; X 1 ~X 4 Exactly two of these are N atoms, bonded to each other, the remaining two are C atoms, and one C atom is bonded to ring D; K 3 and K 4 Each is independently a direct bond, O, or S, and at least one of them is a direct bond; R A , R B , R C , and R D Each of these independently represents up to the maximum number of possible substitutions from a thing, or no substitutions; R A , R B , R C , and RD Each of these substituents is independently selected from the group consisting of hydrogen or general substituents as defined herein; L A It coordinates to metal M via two dashed lines; M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; L A It can combine with other ligands to form tridentate, quadrdentate, quindentate, or hexadentate ligands; Any two adjacent substituents can bond to or condense with each other to form a ring; However, L A The following equation II: [ka] isn't it.)

[0102] In some embodiments, at least one of the anode, cathode, or new layer placed on top of the organic light-emitting layer functions as an enhancement layer. The enhancement layer includes a plasmon material that non-radiatively bonds to the light-emitting material and exhibits surface plasmon resonance, transferring excited state energy from the light-emitting material to non-radiative mode surface plasmon polaritons. The enhancement layer is located within a threshold distance from the organic light-emitting layer, and the light-emitting material has a total non-radiative decay rate constant and a total radioactive decay rate constant in the presence of the enhancement layer, where, at the threshold distance, the total non-radiative decay rate constant is equal to the total radioactive decay rate constant. In some embodiments, the OLED further includes an outcoupling layer. In some embodiments, the outcoupling layer is located on top of the enhancement layer opposite the organic light-emitting layer. In some embodiments, the outcoupling layer is located on the opposite side of the light-emitting layer from the enhancement layer, but still outcouples energy from the surface plasmon modes of the enhancement layer. The outcoupling layer scatters energy from surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, the energy is scattered from the surface plasmon mode to other modes of the device, such as organic waveguide modes, substrate modes, or other waveguide modes, etc. If the energy is scattered to non-free-space modes of the OLED, other outcoupling schemes can be incorporated to extract that energy into free space. In some embodiments, one or more intervening layers can be placed between the enhancement layer and the outcoupling layer. Examples of intervening layers can be dielectric materials including organic, inorganic, perovskite, and oxide materials, and may include laminates and / or mixtures of these materials.

[0103] An enhancement layer alters the effective properties of the medium in which the light-emitting material resides, resulting in one or all of the following: a decrease in luminescence, a change in the shape of the light-emitting line, a change in light-emitting intensity with respect to angle, a change in the stability of the light-emitting material, a change in the efficiency of the OLED, and a decrease in the efficiency roll-off of the OLED device. Placing the enhancement layer on the cathode side, the anode side, or both sides results in an OLED device that takes advantage of any of the aforementioned effects. In addition to the specific functional layers shown in the various OLED examples described and illustrated herein, the OLEDs of this disclosure may include any of the other functional layers commonly found in OLEDs.

[0104] The enhancement layer may consist of a plasmon material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmon material is a material whose real part of dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmon material comprises at least one metal. In such embodiments, the metal may include at least one of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and laminates of these materials. Generally, a metamaterial is a medium composed of different materials, where the medium as a whole behaves differently from the sum of its individual material parts. In particular, an optically active metamaterial is defined as a material having both a negative dielectric constant and a negative magnetic permeability. A hyperbolic metamaterial, on the other hand, is an anisotropic medium in which the dielectric constant or magnetic permeability has different signs for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are distinctly different from many other photonic structures, such as distributed Bragg reflectors ("DBRs"), in that they are media that appear uniform in the direction of propagation on a wavelength scale. Using terminology understandable to those skilled in the art, the dielectric constant of a metamaterial in the direction of propagation can be described by the effective medium approximation. Plasmon and metamaterials provide a way to control the propagation of light and can improve OLED performance in various ways.

[0105] In some embodiments, the enhancement layer is provided as a flat layer. In other embodiments, the enhancement layer has periodically, quasi-periodic, or randomly arranged wavelength-size features, or periodically, quasi-periodic, or randomly arranged sub-wavelength-size features. In some embodiments, the wavelength-size features and sub-wavelength-size features have sharp edges.

[0106] In some embodiments, the outcoupling layer has periodically, quasi-periodic, or randomly arranged wavelength-size features, or periodically, quasi-periodic, or randomly arranged sub-wavelength-size features. In some embodiments, the outcoupling layer may consist of a plurality of nanoparticles, and in other embodiments, the outcoupling layer may consist of a plurality of nanoparticles arranged on a material. In these embodiments, the outcoupling may be tunable by at least one of varying the size of the plurality of nanoparticles, varying the shape of the plurality of nanoparticles, varying the material of the plurality of nanoparticles, adjusting the thickness of the material, varying the refractive index of the material or the refractive index of any further layer arranged on the plurality of nanoparticles, varying the thickness of an enhancement layer, and / or varying the material of the enhancement layer. The plurality of nanoparticles in the device may be formed from at least one of metals, dielectric materials, semiconductor materials, alloys of metals, mixtures of dielectric materials, a laminate or layer of one or more materials, and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, the metal being 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 laminates of these materials. Multiple nanoparticles may have further layers arranged on top of them. In some embodiments, the polarization of the emission can be tuned using the outcoupling layer. By changing the dimension and periodicity of the outcoupling layer, the type of polarization that is preferentially outcoupled to air can be selected. In some embodiments, the outcoupling layer also functions as an electrode in the device.

[0107] In yet another embodiment, the Disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound disclosed in the Compounds section of the Disclosure.

[0108] In some embodiments, the consumer product includes an OLED, the OLED includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a first ligand L of the following formula I. A It contains compounds that include [specific compounds]. [ka] (In the formula, ring B is a 5-membered carbon ring or heteroring; Ring C and ring D are independently 5-membered or 6-membered carbon rings or heterorings; X 1 ~X 4 Exactly two of these are N atoms, bonded to each other, the remaining two are C atoms, and one C atom is bonded to ring D; K 3 and K 4 Each is independently a direct bond, O, or S, and at least one of them is a direct bond; R A , R B , R C , and R D Each of these independently represents up to the maximum number of possible substitutions from a thing, or no substitutions; R A , R B , R C , and R D Each of these substituents is independently selected from the group consisting of hydrogen or general substituents as defined herein; L A It coordinates to metal M via two dashed lines; M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; L AIt can combine with other ligands to form tridentate, quadrdentate, quindentate, or hexadentate ligands; Any two adjacent substituents can bond to or condense with each other to form a ring; However, L A The following equation II: [ka] isn't it.)

[0109] In some embodiments, the consumer product may be one of the following: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signal transmission, head-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays less than 2 inches diagonally, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays arranged side by side, theater or stadium screens, phototherapy devices, and billboards.

[0110] Generally, an OLED includes at least one organic layer positioned between the anode and cathode and electrically connected to them. When an electric current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons move to the oppositely charged electrodes, respectively. When 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. Light is emitted via a photoemission mechanism when the exciton relaxes. In some cases, excitons may be localized on an excimer or exciplex. Non-radiative mechanisms such as thermal relaxation may occur, but these are generally considered undesirable.

[0111] Several OLED materials and configurations are described in U.S. Patent Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated in whole by reference.

[0112] Early OLEDs used light-emitting molecules ("fluorescent") that emitted light from their singlet state, as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated in its entirety by reference. Fluorescence emission generally occurs within a timeframe of less than 10 nanoseconds.

[0113] More recently, OLEDs with light-emitting materials ("phosphorescent") that emit light from a triplet state have been demonstrated. See, in their entirety, Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, Vol. 395, pp. 151-154, 1998 ("Baldo-I") and Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., Vol. 75, No. 3, pp. 4-6 (1999) ("Baldo-II"). Phosphorescence is described in further detail in U.S. Patent No. 7,279,704, paragraphs 5-6, which is incorporated by reference.

[0114] Figure 1 shows an organic light-emitting device 100. The figure is not necessarily to a constant 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, a light-emitting layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. 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 described layers. The properties and functions of these various layers, as well as examples of materials, are described in further detail in US7,279,704, sections 6-10, which are incorporated by reference.

[0115] Further examples are available for each of these layers. For example, flexible and transparent substrate-anode combinations are disclosed in U.S. Patent No. 5,844,363, which is incorporated in its entirety by reference. 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 2003 / 0230980, which is incorporated in its entirety by reference. Examples of luminescent and host materials are disclosed in Thompson et al., U.S. Patent No. 6,303,238, which is incorporated in its entirety by reference. 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 2003 / 0230980, which is incorporated in its entirety by reference. U.S. Patents 5,703,436 and 5,707,745, which are incorporated in their entirety by reference, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with a transparent, conductive, sputtered-deposited ITO layer covering it. The theory and use of blocking layers are described in more detail in U.S. Patents 6,097,147 and U.S. Patent Application Publication 2003 / 0230980, which are incorporated in their entirety by reference. An example of an injection layer is provided in U.S. Patent Application Publication 2004 / 0174116, which is incorporated in its entirety by reference. A description of a protective layer can be found in U.S. Patent Application Publication 2004 / 0174116, which is incorporated in its entirety by reference.

[0116] Figure 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 can be fabricated by depositing the described layers in order. The most common OLED configuration has a cathode positioned above the anode, and since device 200 has a cathode 215 positioned below the anode 230, device 200 can be referred to as an "inverted" OLED. The same materials described for device 100 may be used in the corresponding layers of device 200. Figure 2 provides an example of how some layers may be omitted from the structure of device 100.

[0117] The simple layered structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and embodiments of this disclosure may be used in relation to a wide variety of other structures. The specific materials and structures described are factually illustrative, and other materials and structures may be used. Functional OLEDs may be realized by combining the various layers described in various ways, or layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. While many of the examples provided herein describe various layers as containing a single material, it should be understood that combinations of materials, such as host and dopant mixtures, or more generally, mixtures, may be used. Furthermore, 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, the hole transport layer 225 transports holes and injects them into the light-emitting layer 220, and may be described as a hole transport layer or hole injection layer. In one embodiment, the OLED may be described as having an “organic layer” positioned between the cathode and the anode. The organic layer may consist of a single layer or may further consist of multiple layers of different organic materials, for example, as described with respect to Figures 1 and 2.

[0118] Structures and materials not specifically described may be used, such as OLEDs (PLEDs) composed of polymer materials, as disclosed in U.S. Patent No. 5,247,190 by Friend et al., which is incorporated in whole by reference. Further examples include OLEDs having a single organic layer. OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 by Forrest et al., which is incorporated in whole by reference. OLED structures may deviate from the simple layered structures illustrated in Figures 1 and 2. For example, the substrate may include angled reflective surfaces to improve outcoupling, such as a mesa structure described in U.S. Patent No. 6,091,195 by Forrest et al., which is incorporated in whole by reference, and / or a recessed structure described in U.S. Patent No. 5,834,893 by Bulovic et al.

[0119] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include deposition by thermal deposition, such as those described in U.S. Patent Nos. 6,013,982 and 6,087,196, which are incorporated by reference; inkjet deposition; organic vapor deposition (OVPD), such as those described in U.S. Patent No. 6,337,102 by Forrest et al., which are incorporated by reference; and organic vapor jet printing (OVJP), such as those described in U.S. Patent No. 7,431,968, which are incorporated by reference. Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal deposition. Preferred patterning methods include those described in U.S. Patents No. 6,294,398 and No. 6,468,819, which are incorporated in whole by reference, as well as patterning related to several deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may be used. The material to be deposited may be modified to suit a particular deposition method. For example, substituents such as alkyl and aryl groups, which are branched or unbranched and preferably contain at least three carbon atoms, may be used in low molecular weight materials to enhance their ability to undergo solution processing. Substituents with 20 or more carbon atoms may be used, with 3 to 20 carbon atoms being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures because asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of low molecular weight materials to undergo solution processing.

[0120] Devices fabricated according to embodiments of this disclosure may further include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment, including moisture, vapors and / or gases. The barrier layer may be deposited on, below, or next to the substrate, electrodes, or on any other part of the device, including edges. The barrier layer may consist of a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include single-phase and multi-phase compositions. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferred barrier layers include mixtures of polymer and non-polymer materials, as described in U.S. Patent No. 7,968,146, PCT Patent Application No. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in whole. For a mixture to be considered a "mixture," the polymer and non-polymer materials, including the barrier layer, should be deposited under the same reaction conditions and / or simultaneously. The weight ratio of the polymer material to the non-polymer material can be in the range of 95:5 to 5:95. The polymer and non-polymer materials may be made from the same precursor material. In one example, the mixture of polymer and non-polymer materials essentially consists of polymer silicon and inorganic silicon.

[0121] Devices fabricated according to embodiments of this disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into various electrical products or intermediate components. Such electrical products or intermediate components include display screens and lighting devices (such as discrete light source devices or lighting panels) that can be used by end-user product manufacturers. Such electronic component modules may optionally include drive electronics and / or power supplies. Devices fabricated according to embodiments of this disclosure can be incorporated into a wide variety of consumer products having one or more incorporated electronic component modules (or units). A consumer product is disclosed that includes an OLED in which the organic layer of the OLED contains the compounds of this disclosure. Such a consumer product includes any type of product that includes one or more light sources and / or one or more of the kinds of visual displays. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signal transmission, head-up displays, fully or partially transparent displays, flexible displays, displays that can be rolled up, displays that can be folded, displays that can be stretched, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays less than 2 inches diagonally), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays arranged together, theater or stadium screens, phototherapy devices, and billboards. Devices manufactured in accordance with this disclosure can be controlled using various control mechanisms, including passive matrices and active matrices. Many of the devices are intended for use within a human-comfortable temperature range, such as 18 to 30 degrees Celsius, more preferably room temperature (20 to 25 degrees Celsius), but can also be used outside this temperature range, for example, -40 to +80 degrees Celsius.

[0122] Further details regarding OLEDs and the definitions used herein can be found in U.S. Patent No. 7,279,704, which is incorporated in its entirety by reference.

[0123] The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use these materials and structures. More generally, organic devices such as organic transistors may use these materials and structures.

[0124] In some embodiments, the OLED has one or more properties selected from the group consisting of being flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further includes a layer containing carbon nanotubes.

[0125] In some embodiments, the OLED further includes a layer containing a delayed fluorescence emitter. In some embodiments, the OLED includes an RGB pixel array or a white and color filter pixel array. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of ​​at least 50 square inches. In some embodiments, the OLED is an illumination panel.

[0126] In some embodiments, the compound may be a luminescent dopant. In some embodiments, the compound may produce luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as type E delayed fluorescence; see, for example, U.S. Patent Application No. 15 / 700,352, which is incorporated in whole by reference), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the luminescent dopant may be a racemic mixture or may be enriched with one enantiomer. In some embodiments, the compound may be homoreptic (each ligand is the same). In some embodiments, the compound may be heteroreptic (at least one ligand is different from the others). If there is more than one ligand coordinating to the metal, in some embodiments, these ligands may all be identical. In some other embodiments, at least one ligand is different from the others. In some embodiments, all ligands may be different from each other. This also applies to embodiments in which ligands coordinating to a metal can combine with other ligands coordinating to that metal to form a tridentate, quadrdentate, quindentate, or hexadentate ligand. Therefore, when coordinating ligands are combined with each other, in some embodiments all ligands can be identical, and in some other embodiments at least one of the combined ligands can be different from the others.

[0127] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, and one or more layers in the OLED contain acceptors in the form of one or more fluorescent and / or delayed-fluorescence emitters. In some embodiments, the compound can be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor, which emits energy or further transfers energy to the final emitter. The acceptor concentration may be in the range of 0.001% to 100%. The acceptor may be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission may arise from any or all of the sensitizer, the acceptor, and the final emitter.

[0128] In other embodiments, compositions comprising the compounds described herein are also disclosed.

[0129] The OLEDs disclosed herein can be incorporated into one or more consumer products, electronic component modules, and lighting panels. The organic layer may be an emissive layer, and in some embodiments, the compound may be an emissive dopant, and in other embodiments, the compound may be a non-emissive dopant.

[0130] Further embodiments of this disclosure describe compositions comprising novel compounds disclosed herein. Such compositions may also comprise one or more components selected from the group consisting of solvents, hosts, hole injection materials, hole transport materials, electron blocking materials, and electron transport materials disclosed herein.

[0131] This disclosure encompasses any chemical structure including the novel compounds of this disclosure or their monovalent or polyvalent variants. In other words, the compounds of the present invention or their monovalent or polyvalent 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 known as supermolecules). As used herein, “monovalent variant of a compound” refers to a portion identical to the compound except that one hydrogen atom has been removed and replaced by a bond to the rest of the chemical structure. As used herein, “polyvalent variant of a compound” refers to a portion identical to the compound except that one or more hydrogen atoms have been removed and replaced by bonds to the rest of the chemical structure. In the example of a supramolecule, the inventive compound may also be incorporated into the supramolecular complex without covalent bonding.

[0132] D. Combinations of the compounds disclosed herein with other materials Materials described herein as useful for specific layers in organic light-emitting devices may be used in combination with a wide variety of other materials present in the device. For example, the light-emitting dopants disclosed herein may be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. The materials described or referenced below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that may be useful in combination.

[0133] a) Conductive dopants: Charge transport layers are doped with conductive dopants, significantly altering the density of charge carriers and thereby changing their conductivity. Conductivity is increased by generating charge carriers in the matrix material or, depending on the type of dopant, and changes in the Fermi level of the semiconductor can also be achieved. Hole transport layers can be doped with p-type conductive dopants, while n-type conductive dopants are used in electron transport layers.

[0134] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the literature disclosing these materials. EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012 [ka]

[0135] b) HIL / HTL: The hole injection / transport materials used in this disclosure are not particularly limited, and any compound may be used as long as the compound is typically used as a hole injection / transport material. Examples of materials include: phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorinated hydrocarbons; polymers having conductive dopants; conductive polymers such as PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; and MoO2. x This includes, but is not limited to, metal oxide derivatives such as; p-type semiconductor organic compounds such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonnitrile; metal complexes; and crosslinkable compounds.

[0136] Examples of aromatic amine derivatives used in HIL or HTL include, but are not limited to, the general structures shown below. [ka]

[0137] Ar 1 From Ar 9Each of these is a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiaidine, oxadiazine, indole, benzimidazole, indazole, indoxy The group consists of aromatic heterocyclic compounds such as sazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzophropyridine, phlodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenofenodipyridine; and the group consists of 2 to 10 cyclic structural units that are the same or different types of groups selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and are bonded to each other directly or via at least one of an oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit, and aliphatic cyclic group. Each Ar can be unsubstituted, or it can be substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinone, and combinations thereof.

[0138] In one aspect, Ar 1 From Ar9 teeth, [ka] (wherein k is an integer from 1 to 20; X 101 From X 108 is C (including CH) or N; Z 101 is NAr 1 , O, or S; Ar 1 It has the same group as defined above.) It is independently selected from the group consisting of ).

[0139] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formulas. [ka] In the formula, Met is a metal that may have an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 is independently selected from C, N, O, P and S; L 101 k' is an auxiliary ligand; k' is an integer value from 1 up to the maximum number of ligands that can bond to the metal; and k'+k'' is the maximum number of ligands that can bond to the metal.

[0140] In one embodiment, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another embodiment, (Y 101 -Y 102 ) is a carbene ligand. In another embodiment, Met is selected from Ir, Pt, Os and Zn. In a further embodiment, the metal complex is Fc + For the / Fc couple, it has a minimum oxidation potential of less than approximately 0.6V in solution.

[0141] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the literature disclosing these materials. CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07-073529、JP2005112765、JP2007091719、JP2008021687、JP2014-009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018 [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0142] c)EBL: An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons emitted from the light-emitting layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or a longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to restrict light emission to a desired region of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than the light-emitting element closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the EBL interface. In one embodiment, the compound used in the EBL contains the same molecule or the same functional group as one of the hosts described below.

[0143] d) Host: The light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may include a host material using the metal complex as a dopant material. The host material is not particularly limited, and any metal complex or organic compound can be used as long as the triplet energy of the host is greater than that of the dopant. Any host material can be used with any dopant as long as the triplet criterion is met.

[0144] Examples of metal complexes used as host materials preferably have the following general formula. [ka] In the formula, Met is a metal; (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 is independently selected from C, N, O, P and S; L 101 k' is another ligand; k' is an integer value from 1 up to the maximum number of ligands that can bond to the metal; and k'+k'' is the maximum number of ligands that can bond to the metal.

[0145] In one embodiment, the metal complex is the following complex. [ka] In the formula, (ON) is a bidentate ligand having a metal coordinated to atoms O and N.

[0146] In another embodiment, Met is selected from Ir and Pt. In a further embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0147] In one embodiment, the host compound is a group of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiaidine, oxadiazine, indole, benzimidazole, indazo A group consisting of aromatic heterocyclic compounds such as iodine, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzophropyridine, phlodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenofenodipyridine; and at least one of a group consisting of 2 to 10 cyclic structural units that are the same or different types of groups selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and are bonded to each other directly or via at least one of an oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and aliphatic cyclic group. Each option within each group may be unsubstituted, or may be substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof.

[0148] In one embodiment, the host compound contains at least one of the following groups in its molecule. [ka] [ka] In the formula, R 101 k is selected from the group consisting of hydrogen, deuterium, halogens, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof, and if it is aryl or heteroaryl, it has the same definition as that of Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X 101 ~X 108 Z is independently selected from C (including CH) or N. 101 and Z 102 NR is independent. 101 Selected from O, or S.

[0149] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the literature disclosing these materials. EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564 , TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US2 0090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012 126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO200706375 4. WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO20100 56066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO 2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803

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[0150] e) Additional light-emitting elements: One or more additional luminescent dopants may be used with the compounds of this disclosure. Examples of such additional luminescent dopants are not particularly limited, and any compound can be used as long as the compound is typically used as a luminescent material. Examples of suitable luminescent materials include, but are not limited to, compounds that can generate light through phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as type E delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0151] Non-limiting examples of light-emitting materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the literature disclosing these materials. CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US 2014103305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US73 32232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586 , US8871361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO200201 5645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842 , WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO20 11044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO201317 4471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450,

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[0152] f) HBL: A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons emitting from the light-emitting layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or a longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to restrict light emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and / or a higher triplet energy than the light-emitting material closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and / or a higher triplet energy than one or more hosts closest to the HBL interface.

[0153] In one embodiment, the compound used in the HBL contains the same molecule or the same functional group as the one used in the host described above.

[0154] In another embodiment, the compound used in the HBL contains at least one of the following groups in its molecule. [ka] In the formula, k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0155] g) ETL: An electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer 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, as long as it is typically used for electron transport.

[0156] In one embodiment, the compound used in the ETL contains at least one of the following groups in its molecule. [ka] In the formula, R 101 Ar is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof, and if it is aryl or heteroaryl, it has the same definition as Ar mentioned above. 1 From Ar 3 It has the same definition as Ar mentioned above. k is an integer from 1 to 20. X 101 From X 108 This is selected from C (including CH) or N.

[0157] In another embodiment, the metal complex used in the ETL may include, but is not limited to, the following general formulas. [ka] In the formula, (ON) or (NN) is a bidentate ligand having a metal coordinated to atoms O, N, or N, N; L 101 ' is another ligand; k' is an integer value from 1 up to the maximum number of ligands that can bond to the metal.

[0158] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below, along with the literature disclosing these materials. CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2 005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, U S20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US20 11210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO20 09148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, W O2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535 [ka] [ka] [ka]

[0159] h) Charge Generation Layer (CGL) In tandem or stacked OLEDs, the transport layer (CGL) plays a crucial role in performance, consisting of an n-doped layer and a p-doped layer for electron and hole injection, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively, after which the bipolar current gradually stabilizes. Typical CGL materials include n-type and p-type conductive dopants used in the transport layer.

[0160] In any of the compounds mentioned above used in each layer of an OLED device, hydrogen atoms may be partially or completely deuterated. The minimum amount of hydrogen in the deuterated compounds is selected from the group consisting of 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. Thus, any specifically mentioned substituents, such as but not limited to methyl, phenyl, and pyridyl, can have non-deuterated, partially deuterated, and fully deuterated versions. Similarly, classes of substituents, such as but not limited to alkyl, aryl, cycloalkyl, and heteroaryl, can also have non-deuterated, partially deuterated, and fully deuterated versions.

[0161] The various embodiments described herein are merely examples and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the invention. Accordingly, the claimed invention may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. The various theories of why the invention works are not intended to limit it.

[0162] E. Experiment Section Synthesis of the compound of the present invention 6-Chloro-3-(3-chloro-2-(methylthio)phenyl)pyridazine-4-amine [ka] In a three-necked flask, (3-chloro-2-(methylthio)phenyl)boronic acid (15 g, 74.1 mmol), 3,6-dichloropyridazine-4-amine (12.2 g, 74.4 mmol), Pd(PPh3)4 (4.3 g, 3.72 mmol), aqueous sodium carbonate solution (2 M, 110 mL, 220 mmol), and THF (250 mL) were placed. The mixture was degassed by bubbling with N2 for 15 minutes, then heated to 70°C and stirred for 16 hours. After cooling to room temperature, the mixture was diluted with ELISA (100 mL), the aqueous layer was separated and discarded. The organic layer was dried over MgSO4, filtered, and the solvent was removed by vacuum. The residue was packed into silica and purified by flash column chromatography (330 g column, 0-4% MeOH / DCM). The fraction containing the product was collected and concentrated. The residue was ground with MTBE (100 mL) and stirred at room temperature for 30 minutes. The solid was collected by filtration and dried to obtain 6-chloro-3-(3-chloro-2-(methylthio)phenyl)pyridazin-4-amine (16.5 g, 57.2 mmol, 77% yield) as a white solid.

[0163] 3,6-Dichlorobenzo[4,5]thieno[3,2-c]pyridazine and 6-chlorobenzo[4,5]thieno[3,2-c]pyridazine-3-ol [ka] tBuONO (15.3 ml, 116 mmol) was added dropwise at 0°C to a stirred solution of 6-chloro-3-(3-chloro-2-(methylthio)phenyl)pyridazin-4-amine (16.54 g, 57.8 mmol) in THF / AcOH (1:1,580 mL). The mixture was warmed to room temperature and stirred for 2 hours. The mixture was diluted with water (500 mL) and stirred for 1 hour. The resulting precipitate was collected by filtration, washed with water (2 × 50 mL), and vacuum-dried for 16 hours to obtain a mixture of 3,6-dichlorobenzo[4,5]thieno[3,2-c]pyridazine (7.27 g, 23.37 mmol, 40% yield, 82% LCMS purity) and 6-chlorobenzo[4,5]thieno[3,2-c]pyridazine-3-ol (7.27 g, 5.53 mmol, 10% yield, 18% LCMS purity).

[0164] 3,6-Dichlorobenzo[4,5]thieno[3,2-c]pyridazine hydrochloride [ka] In an oven-dried flask, 3,6-dichlorobenzo[4,5]thieno[3,2-c]pyridazine (7.25 g, 23.30 mmol, 82% LC-MS purity), 6-chlorobenzo[4,5]thieno[3,2-c]pyridazine-3-ol (7.25 g, 5.50 mmol, 18% LC-MS purity), anhydrous PhMe (90 mL), and phosphorus oxychloride (5 mL, 53.6 mmol) were added. The mixture was heated to 100°C and stirred under N2 for 4 hours. After cooling to room temperature, volatile components were removed by vacuum, and the residue was suspended in MTBE (25 mL) and thoroughly sonicated. The solid was recovered by filtration and vacuum-dried to obtain 3,6-dichlorobenzo[4,5]thieno[3,2-c]pyridazine hydrochloride (7.2 g, 23.46 mmol, 81% yield) as a brown solid.

[0165] 3-Bromo-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine hydrobromide and 3,6-dichlorobenzo[4,5]thieno[3,2c]pyridazine hydrobromide [ka] 7.2 g, 24.69 mmol, anhydrous MeCN (12 mL), and 32.0 mL, 247 mmol, TMS-Br were placed in an oven-dried flask. The mixture was heated to 80°C and stirred under N2 for 24 hours. The reaction mixture was cooled and diluted with MTBE (100 mL). The solid was isolated by filtration and vacuum-dried to obtain a mixture of 3-bromo-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine hydrobromide (6.76 g, 10.66 mmol, 43% yield) and 3,6-dichlorobenzo[4,5]thieno[3,2-c]pyridazine hydrobromide (6.76 g, 8.05 mmol, 33% yield) as a brown solid.

[0166] 3-(4-(Tert-butyl)naphthalene-2-yl)-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine [ka] In an oven-dried and N2-flashed flask, the following were added: 3-bromo-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine hydrobromide (6.76 g, 10.66 mmol, 60% LCMS purity), 3,6-dichlorobenzo[4,5]thieno[3,2-c]pyridazine hydrobromide (6.76 g, 8.05 mmol, 40% LCMS purity), 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7,6.39 g, 20.58 mmol), anhydrous PhMe (95 mL), and potassium carbonate aqueous solution (2.5 M; 37.4 mL, 94 mmol). The mixture was degassed by bubbling with N2 for 30 minutes, and then Pd(dppf)Cl2.DCM (0.762 g, 0.936 mmol) was added. The mixture was heated to 100°C and stirred for 24 hours. After cooling to room temperature, the mixture was separated into water (500 mL) and ethyl acetate (200 mL). The aqueous layer was extracted with ethyl acetate (200 mL). The combined organic layers were washed with brine (300 mL), dried over MgSO4, filtered, and the solvent was removed by vacuum. The residue was packed into silica and purified by silica gel chromatography (330 g cartridge, 0-25% ethyl acetate / cyclohexane) to obtain a pale yellow solid. This was dissolved in DCM (85 mL), filtered, and eluted over 5 minutes with a water-MeCN gradient using a PDA for UV detection across all wavelengths, as well as QDA and ELS detectors. (Waters X-Select CSH C18 ODB prep column, 130 Å, 5 μm, 30 mm × 100 mm, flow rate 40 mL min) -1 The solution was purified by reverse-phase preparative HPLC. The solution was then diluted using an At-column dilution pump, with a total dilution of 2 mL min throughout the entire process. -1MeCN was obtained. This contained the following MeCN%: Gradient information: 0.0 to 0.5 minutes, 95% MeCN; 0.5 to 5.5 minutes, gradient from 95% MeCN to 100% MeCN; maintained at 100% MeCN for 5.5 to 8.5 minutes. The clarified fraction was concentrated by rotary evaporation to obtain 3-(4-(tert-butyl)naphthalen-2-yl)-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine (3.42 g, 8.40 mmol, 45% yield) as an off-white solid.

[0167] 3-(4-(Tert-butyl)naphthalene-2-yl)-6-neopentylbenzo[4,5]thieno[3,2-c]pyridazine [ka] Under nitrogen, a solution of 3-(4-(tert-butyl)naphthalen-2-yl)-6-chlorobenzo[4,5]thieno[3,2-c]pyridazine (2.00 g, 4.96 mmol) and XPhos Pd G4 (0.214 g, 0.248 mmol) in 20 mL of anhydrous 0.5 M LiCl THF was mixed with neopentyl zinc(II) bromide (0.4 M in THF) (36 mL, 14.40 mmol). The reaction mixture was stirred at 50°C for 2 hours. After cooling, the reaction mixture was separated into ELISA (100 mL) and 50% brine (100 mL). Each layer was separated, the organic layer was washed with brine (100 mL), dried over MgSO4, filtered, and the solvent was removed under vacuum. The residue was purified by flash column chromatography (120 g gold column, 0-20% siRNA / isohexane). The fraction containing the product was collected and concentrated under vacuum. The residue was slurryed in warm MeCN (50 mL, 70 °C) for 2 hours. After cooling to room temperature, the solid was collected by filtration and vacuum-dried to obtain 3-(4-(tert-butyl)naphthalen-2-yl)-6-neopentylbenzo[4,5]thieno[3,2-c]pyridazine (1.43 g, 3.26 mmol, 66% yield) as a white solid.

[0168] Di-μ-chlorotetrakis-[(3-(4-(tert-butyl)naphthalene-2-yl)-1'-yl)-6-neopentyl-benzo[4,5]thieno[3,2-c]pyridazine-2-yl]diiridium(III) [ka] Iridium(III) chloride hydrate (0.45 g, 1.42 mmol, 1.0 equiv) was added to a nitrogen-spurged solution of 3-(4-(tert-butyl)naphthalen-2-yl)-6-neopentylbenzo[4,5]-thieno[3,2-c]pyridazine (1.13 g, 2.6 mmol, 1.8 equiv) in 2-ethoxyethanol (15 mL) and DIUF water (5 mL). The reaction mixture was heated at 102 °C. After 48 hours, 1 ¹H-NMR and LC-MS analysis showed conversion to a stalled product at ~50%. The reaction mixture was cooled to room temperature. The solid was filtered and washed with DIUF water (100 mL) and then methanol (50 mL) to obtain di-μ-chlorotetrakis-[(3-(4-(tert-butyl)naphthalene-2-yl)-1'-yl)-6-neopentyl-benzo[4,5]thieno[3,2-c]pyridazin-2-yl]diiridium(III) as a reddish-brown solid wetted with the crude solvent containing the remaining ligand (1.7 g, >100% yield).

[0169] Bis[(3-(4-(tert-butyl)naphthalene-2-yl)-1'-yl)-6-neopentylbenzo[4,5]thieno[3,2-c]pyridazine-2-yl]-[3,7-diethylnonane-4,6-dione-k2O,O']iridium(III) [ka] Di-μ-chlorotetrakis-[(3-(4-(tert-butyl)naphthalene-2-yl)-1'-yl)-6-neopentylbenzo[4,5]thieno[3,2-c]pyridazin-2-yl]-diiridium(III) (1.7 g, 0.8 mmol, 1.0 equiv) was spurged with nitrogen in a 1:1 mixture of dichloromethane and methanol (30 mL). 3,7-diethylnonane-4,6-dione (0.65 g, 3.1 mmol, 4.0 equiv) was added using a syringe. Powdered potassium carbonate (0.64 g, 4.6 mmol, 6.0 equiv) was then added, and the reaction mixture was heated to 42°C in a flask wrapped in foil to protect it from light. After 16 hours, 1 ¹H NMR analysis indicated that the reaction was complete. The reaction mixture was poured into methanol (300 mL), and the suspension was filtered. The red solid was washed with methanol (150 mL) and DIUF water (250 mL), and then dried in a vacuum oven at 45°C for 2 hours. The red solid (890 mg) was adsorbed onto basic alumina (60 g) packed in a 60 g dry cartridge, and then purified using an Interchim automated chromatography system (two stacked 120 g silica gel cartridges) eluted with a hexane solution of 5-20% ethyl acetate. The highest purity product fraction was concentrated under reduced pressure. The solid was dried in a vacuum oven at 50°C for 16 hours to obtain bis[(3-(4-(tert-butyl)naphthalene-2-yl-1'-yl)-6-neopentyl-benzo[4,5]thieno[3,2-c]pyridazin-2-yl]-[3,7-diethylnonane-4,6-dionate-k2O,O']-iridium(III) as a red solid (0.33 g, 17% yield).

[0170] Figure 3 shows the photoluminescence (PL) spectrum of the present invention example obtained in PMMA. The PL intensity was normalized to the maximum value of the first emission peak. The present invention example exhibits photoluminescent emission at 615 nm with a good photoluminescence quantum yield (PLQY = 68%) and a short transient (τ = 1.48 μs). The results demonstrate that the pyridazine moiety as the ring at the top of the ligand can produce the desired red color with good photoluminescent properties, which is very important for applications in OLED devices.

Claims

1. A first ligand L selected from the following group Ａ A compound characterized by containing the following: 【Chemistry 1】 (In the formula, Y ３ is S; R C1 and R D1 each independently represent the maximum number of possible substitutions from the mono, or no substitutions; R A1, R C1, and R D1 are each independently substituents selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, gelmyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphinol, and combinations thereof; L Ａ It coordinates to metal M via two dashed lines; M is Ir; L Ａ It can combine with other ligands to form tridentate, quadrdentate, quindentate, or hexadentate ligands; Any two adjacent substituents can bond to or condense with each other to form a ring.

2. The compound according to claim 1, wherein RA1, RC1, and RD1 are each independently substituents selected from the group consisting of hydrogen, or deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanil, and combinations thereof.

3. The compound according to claim 1, wherein two adjacent R C1 molecules bond or condense with each other to form a ring; and / or two adjacent R D1 molecules bond or condense with each other to form a ring.

4. Ligand L Ａ However, L Ａｉ－ｍ－Ｘ Selected from the group consisting of, where i is an integer from 1 to 1200, m is an integer from 1 to 6, and X is 2 in the case of S, L Ａｉ－１－Ｘ ~LAi-6-X is a compound according to claim 1, each having the structure defined below. 【Chemistry 2】 (wherein, for each case of L Ａ１ to L Ａ１２００ , R Ｅ , R Ｆ , and G are defined as follows.) Table 1 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 (In the formula, R １ ~R ４０ It has the following structure. 【Transformation 3】 (In the formula, G １ (G10 and G21 have the following structure.) 【Chemistry 4】

5. The above compound is 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 It has an expression selected from the group consisting of; L Ｂ and L Ｃ These are each bidentate ligands; L Ａ , L Ｂ , and L Ｃ The compounds according to claim 1, which are different from each other.

6. The above compound is of formula Ir(L Ａｉ－ｍ－Ｘ ) ３ When i is an integer between 1 and 1200, m is an integer between 1 and 6, X is 2, and the compound is Ir(LA1-1-2) ３ ~Ir (LA1200-6-2) ３ Selected from the group consisting of; The above compound is of formula Ir(L Ａｉ－ｍ－Ｘ ) (L Ｂｋ ) ２ When it has i is an integer from 1 to 1200, m is an integer from 1 to 6, X is 2, k is an integer from 1 to 270, and the compound is Ir(LA1-1-2)(L Ｂ１ ) ２ ~Ir(LA1200-6-2)(L Ｂ２７０ ) ２ Selected from the group consisting of; The above compound is of formula Ir(L Ａｉ－ｍ－Ｘ ) ２ (L Ｂｋ When it has ), i is an integer from 1 to 1200, m is an integer from 1 to 6, X is 2, k is an integer from 1 to 270, and the compound is Ir(LA1-1-2) ２ (L Ｂ１ ) ~ Ir (LA1200-6-2) ２ (L Ｂ２７０ Selected from the group consisting of; The above compound is of formula Ir(L Ａｉ－ｍ－Ｘ ) ２ (L Ｃｊ－Ｉ When it has ), i is an integer from 1 to 1200, m is an integer from 1 to 6, X is 2, j is an integer from 1 to 1416, and the compound is Ir(LA1-1-2) ２ (L Ｃ１－Ｉ ) ~ Ir (LA1200-6-2) ２ (L Ｃ１４１６－Ｉ Selected from the group consisting of; The above compound is of formula Ir(L Ａｉ－ｍ－Ｘ ) ２ (L Ｃｊ－ＩＩ When it has ), i is an integer from 1 to 1200, m is an integer from 1 to 6, X is 2, j is an integer from 1 to 1416, and the compound is Ir(LA1-1-2) ２ (L Ｃ１－ＩＩ ) ~ Ir (LA1200-6-2) ２ (L Ｃ１４１６－ＩＩ Selected from the group consisting of; Each L Ａｉ－ｍ－Ｘ The structure is the compound according to claim 5, as defined below. 【Transformation 5】 (In the formula, L Ａ１ ~L Ａ１２００ In each case, R Ｅ , R Ｆ , and G are defined below. Table 2 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 (In the formula, each L Ｂｋ It has the structure defined below. 【Transformation 6】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 (In the formula, each L Ｃｊ－Ｉ The formula is: 【Transformation 7】 It has a structure based on; each L Ｃｊ－ＩＩ The formula is: 【Transformation 8】 It has a structure based on the formula, where L Ｃｊ－Ｉ and L Ｃｊ－ＩＩ Each L in Ｃｊ In R ２０１ and R ２０２ (This is defined as follows:) Table 3 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 (In the formula, R Ｄ１ ~R Ｄ２４６ It has the structure defined below. 【Chemistry 9】 【change】 【change】 【change】

7. The compound according to claim 1, wherein the compound is selected from the group consisting of the following. 【Chemistry 10】

8. Organic light-emitting devices (OLEDs), A-scatter, Cathode and, It includes an organic layer disposed between the anode and the cathode, An organic light-emitting device (OLED) characterized in that the organic layer contains a compound according to any one of claims 1 to 7.

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