Organic electroluminescent materials and devices

Abstract

To provide novel compounds for use in organic light emitting diodes / devices (OLEDs).SOLUTION: For example, a compound in the table in the figure is provided.SELECTED DRAWING: None

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Application No. 63 / 145,311 filed 3 February 2021, pursuant to Section 119(e) of the U.S. Patent Act, and the entirety of this disclosure is 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 use of phosphorescent light-emitting molecules is in full-color displays. Industry standards for such displays require pixels adapted to emit specific colors called "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 display emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. Similar techniques can also be used in OLEDs. White OLEDs can be either single-layer emissive layer (EML) devices or stacked structures. Colors can be measured using CIE coordinates well known in the art. Summary of the Invention

[0006] In one aspect, the present disclosure provides a compound comprising a first ligand L of formula I below: [Chemical Formula] of the first ligand L A . In formula I, Ring B is a 5- or 6-membered carbocyclic or heterocyclic ring; Y is selected from the group consisting of O, S, NR Y , and CR Y R Y’ ; Z 1 is selected from the group consisting of O, S, NR, and CRR'; X 1 is selected from the group consisting of C and N; R A and R B each independently represent from one substitution to the maximum number of possible substitutions, or represent no substitution; R, R', R Y , R Y’ , R A , and R B are each independently hydrogen or a substituent selected from the group consisting of the general formulas defined herein; L AIt coordinates to metal M via the dashed line; M is a metal with an atomic weight greater than 40; M can coordinate to other ligands; L A It can combine with other ligands to include tridentate, quadridentate, quindentate, sextate, or heptate ligands; R, R', R Y , R Y’ , R A , and R B Any two of them can combine or condense to form a ring; However, the above-mentioned compound does not contain formula II below. [ka] In the formula, Z' and Z'' are C or N, respectively.

[0007] In another embodiment, the Disclosure provides compositions of the compounds of the Disclosure.

[0008] In yet another embodiment, the Disclosure provides an OLED having an organic layer comprising the compound of the Disclosure.

[0009] In yet another embodiment, the Disclosure provides a consumer product comprising an OLED having an organic layer containing the compound of the Disclosure. [Brief explanation of the drawing]

[0010] [Figure 1] Figure 1 shows an organic light-emitting device.

[0011] [Figure 2] Figure 2 shows an inverted organic light-emitting device that does not have another electron transport layer. [Modes for carrying out the invention]

[0012] A. Terminology Unless otherwise specified, the following terms used in this specification are defined as follows:

[0013] 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.

[0014] 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.

[0015] 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.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] The terms "halo," "halogen," and "halide" are interchangeable and refer to fluorine, chlorine, bromine, and iodine.

[0020] The term "acyl" refers to a substituted carbonyl group (C(O)-R s ) refers to.

[0021] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-Rs OR C(O)-OR s ) refers to the base.

[0022] The term "ether" is -OR s It refers to the base.

[0023] The terms "sulfanil" and "thioether" are used interchangeably, -SR s It refers to the base.

[0024] The term "selenyl" is SeR s It refers to the base.

[0025] The term "sulfinyl" is -S(O)-R s It refers to the base.

[0026] The term "sulfonyl" is -SO2-R s It refers to the base.

[0027] The term "phosphino" is -P(R s ) refers to 3 units, each R s They may be the same or different.

[0028] The term "silyl" is -Si(R s ) refers to 3 units, each R s They may be the same or different.

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

[0030] 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.

[0031] In each of the above, R sR 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.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] The terms "aralkyl" or "arylalkyl" are interchangeable and refer to alkyl groups substituted with aryl groups. Furthermore, the aralkyl groups may be optionally substituted.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphine, boryl, and combinations thereof.

[0044] In some examples, preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.

[0045] In some examples, more 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.

[0046] In other examples, the most preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0047] 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, 1This 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.

[0048] Where used herein, “their combinations” means that one or more members of the applicable list are combined to form a known or chemically stable configuration that can be conceived by a person skilled in the art from the applicable list. For example, alkyl and deuterium can be combined to form a partially or completely 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 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] B. Compounds of the present disclosure The compounds described herein utilize novel bonding groups in which metal atoms are bonded via oxygen, sulfur, nitrogen, or carbon atoms. The bonded O, S, N, or C atoms are attached to a heterocycle via double bonds. These newly invented complexes exhibit a blue-shifted emission spectrum while maintaining many of the structural features of known stable blue emitters.

[0054] In one embodiment, this disclosure relates to the following formula I: [ka] The first ligand L A The present invention provides compounds containing the above. In equation I, Ring B is a five-membered or six-membered carbon ring or heteroring; Y is O, S, NR Y , and CR Y R Y’ Selected from the group consisting of; Z 1 It is selected from the group consisting of O, S, NR, and CRR'; X 1 It is selected from the group consisting of C and N; R A and R B Each of these independently represents the maximum number of possible substitutions from a thing, or no substitutions; R, R', R Y , R Y’ , R A , and R B Each of these is independently hydrogen or a substituent selected from the group consisting of general formulas as defined herein; L A It coordinates to metal M via the dashed line; M is a metal with an atomic weight greater than 40; M can coordinate to other ligands; L A It can combine with other ligands to include tridentate, quadridentate, quindentate, sextate, or heptate ligands; R, R', R Y , RY’ , R A , and R B Any two of them can combine or condense to form a ring; However, the above-mentioned compound does not contain formula II below. [ka] In the formula, Z' and Z'' are C or N, respectively.

[0055] In some embodiments, R, R', R Y , R Y’ , R A , and R B Each of these is independently a substituent selected from the group consisting of hydrogen or preferred general substituents as defined herein. In some embodiments, R, R', R Y , R Y’ , R A , and R B Each of these is independently a substituent selected from the group consisting of hydrogen or more preferred general substituents as defined herein. In some embodiments, R, R', R Y , R Y’ , R A , and R B Each of these substituents is independently selected from the group consisting of hydrogen or the most preferred general substituents as defined herein.

[0056] In some embodiments, ring B is a five-membered or six-membered aryl or heteroaryl ring. In some embodiments, ring B is benzene.

[0057] In some embodiments, Y is O. In some embodiments, Y is S. In some embodiments, Y is NR Y In some embodiments, R Y The group is selected from alkyl, aryl, and combinations thereof.

[0058] In some embodiments, Y is CR Y R Y’ . In some such embodiments, R Y and R Y’ at least one of is selected from the group consisting of alkyl, aryl, and combinations thereof.

[0059] In some embodiments, Z 1 is O. In some embodiments, Z 1 is S.

[0060] In some embodiments, Z 1 is NR. In some such embodiments, R is selected from the group consisting of alkyl, aryl, and combinations thereof.

[0061] In some embodiments, Z 1 is CRR'. In some embodiments, at least one of R and R' is selected from the group consisting of alkyl, aryl, and combinations thereof.

[0062] In some embodiments, Y is NR Y and Z 1 is NR, and R Y and R are bonded or fused to each other to form a ring; the shortest distance between Y formed by R Y and R and Z 1 is at least 3 atoms. In some such embodiments, the shortest distance between Y formed by R Y and R and Z 1 is at least 4 atoms. In some such embodiments, the shortest distance between Y formed by R Y and R and Z 1 is at least 5 atoms.

[0063] In some embodiments, Y is NR Y or CR Y R Y’ and Z 1is NR or CRR', and R Y and R are bonded or fused to each other to form a ring.

[0064] In some embodiments, Z 1 is NR, and Y is NR Y and R and R Y are not bonded or fused to form a ring.

[0065] In some embodiments, R A represents disubstitution, and said R A are bonded or fused to each other to form a ring. In some embodiments, R A represents disubstitution, and said R A are bonded or fused to each other to form a benzene or pyridine ring.

[0066] In some embodiments, two adjacent R B are bonded or fused to each other to form a ring. In some embodiments, two adjacent R B are bonded or fused to each other to form a benzene or pyridine ring.

[0067] In some embodiments, X 1 is C. In some embodiments, X 1 is N.

[0068] In some embodiments, the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In some embodiments, the metal M is Ir. In some embodiments, the metal M is Pt.

[0069] In some embodiments, the ligand L A is selected from the group consisting of the structures in the following List 1.

Chemical Formula

Chemical Formula

[0070] In some embodiments, ligand L A The following group is selected from the structures listed in List 2 below. [ka] [ka] During the ceremony, Z is O, S, Se, or NR; X2 to X5 are each independently either CR or N; Y' is either N or C; R A1 , R A’ , and R CEach of these substituents is independently selected from the group consisting of hydrogen or general substituents as defined herein.

[0071] In some embodiments, ligand L A The following group is selected from the structures listed in List 3 below. [ka] JPEG0007927427000011.jpg222152JPEG0007927427000012.jpg195152JPEG0007927427000013.jpg219153JPEG0007927427000014.jpg220152JPEG0007927427000015.jpg223152JPEG0007927427000016.jpg220152JPEG0007927427000017.jpg39153Here, R1~R307 are defined in the following List 4. [ka] JPEG0007927427000019.jpg207160JPEG0007927427000020.jpg211160JPEG000 7927427000021.jpg190160JPEG0007927427000022.jpg183160JPEG0007927427 000023.jpg186160JPEG0007927427000024.jpg174160JPEG0007927427000025. jpg206160JPEG0007927427000026.jpg191160JPEG0007927427000027.jpg54160

[0072] In some embodiments, the compound is of formula M(L A ) p (L B ) q (L C ) r It has, in the formula, L B and L Ceach represents a bidentate ligand; 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 said metal M.

[0073] 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 )and has a formula selected from the group consisting of; L A , L B , and L C are different from each other.

[0074] In some embodiments, the compound is a compound of formula Pt(L A )(L B ); L A and L B may be the same or different. In some Pt complexes, L A and L B bond to form a tetradentate ligand.

[0075] In some embodiments, L B and L C are each independently selected from the group consisting of structures of List 5 as defined below.

Chemical Formula

[0076] In some embodiments, L B and L C Each of these is independently selected from the group consisting of List 6 defined below. [ka] JPEG0007927427000031.jpg206160JPEG0007927427000032.jpg108160In the formula, R a ', R b ', and R cEach of these independently represents zero, mono, or the maximum number of possible permutations for the associated ring; R a1 , R b1 , R c1 , R a , R b , R c , R N , R a ', R b ', and R c ' is a substituent selected independently from the group consisting of hydrogen or general substituents as defined herein; and R a ', R b ', and R c Any two substituents among them can condense or bond to form a ring, or form a polydentate ligand.

[0077] In some embodiments, the compound is Ir(L A )3, Ir(L A )(L Bk )2, Ir(L A )2(L Bk ), Ir(L A )2(L Cj-I ), Ir(L A )2(L Cj-II ), Ir(L A )(L Bk )(L Cj-I ), and Ir(L A )(L Bk )(L Cj-II You can choose from the group consisting of ), where k is an integer from 1 to 324, j is an integer from 1 to 1416, and L A The structure is selected from the structures defined herein; each L Bk This is defined herein in List 7; L Cj-I and L Cj-II Each of these terms is defined herein in List 8.

[0078] In some embodiments, the compound is of the formula Ir(L A When )3 is present, the compound is Ir(L A1-(1)(1)(1)(1)(1) n )3~Ir(L A 41-(292)(307)(307)(307)(307) n Selected from the group consisting of )3 (wherein m is present, n is 1, and otherwise n is 0); The aforementioned compound is of formula Ir(L A )(L Bk When the compound has )2 (wherein k is an integer from 1 to 324); the compound is Ir(L A 1-(1)(1)(1)(1)(1) n )(L B1 )2~Ir(L A 41-(292)(307)(307)(307)(307) n )(L B324 Selected from the group consisting of )2 (wherein m is present, n is 1, and otherwise n is 0); The aforementioned compound is of formula Ir(L A )2(L Bk When the compound has (wherein k is an integer from 1 to 324), the compound is Ir(L A 1-(1)(1)(1)(1)(1) n )2(L B1 )~Ir(L A 41-(292)(307)(307)(307)(307) n )2(L B324 Selected from the group consisting of ) (wherein the formula, if m exists, n is 1, and otherwise n is 0); The aforementioned compound is of formula Ir(L A )2(L Cj-I When the compound has (wherein j is an integer from 1 to 1416), the compound is Ir(L A 1-(1)(1)(1)(1)(1) n )2(L C1-I )~Ir(L A 41-(292)(307)(307)(307)(307) n ) (L C1416-I Selected from the group consisting of ) (wherein the formula, if m exists, n is 1, and otherwise n is 0); The aforementioned compound is of formula Ir(LA )2(L Cj-II When the compound has (wherein j is an integer from 1 to 1416), the compound is Ir(L A 1-(1)(1)(1)(1)(1) n )2(L C1-II )~Ir(L A 41-(292)(307)(307)(307)(307) n )(L C1416-II Selected from the group consisting of ) (wherein the formula, if m exists, n is 1, and otherwise n is 0); L A 1-(1)(1)(1)(1)(1) n ~L A 41-(292)(307)(307)(307)(307) n The structure is defined in List 3, where n is 1 if m exists, and 0 otherwise; Each L Bk It has the structure defined in List 7 below. [ka] JPEG0007927427000034.jpg202160JPEG0007927427000035.jpg198160JPEG0007 927427000036.jpg201160JPEG0007927427000037.jpg171160JPEG0007927427000 038.jpg189160JPEG0007927427000039.jpg191160JPEG0007927427000040.jpg16 8160JPEG0007927427000041.jpg174160JPEG0007927427000042.jpg134160In the formula, each L Cj-I The formula is as follows: [ka] It has a structure based on; Each L Cj-II The formula is as follows: [ka] It has a structure based on; L Cj-I and L Cj-II Each L in Cj Regarding R 201 and R 202 Each of these is defined independently in List 8 below. [ka] JPEG0007927427000046.jpg212160JPEG0007927427000047.jpg212160JPEG0007927427000048.jp g214160JPEG0007927427000049.jpg213160JPEG0007927427000050.jpg214160JPEG000792742700 0051.jpg214160JPEG0007927427000052.jpg213160JPEG0007927427000053.jpg213160JPEG00079 27427000054.jpg214160JPEG0007927427000055.jpg212160JPEG0007927427000056.jpg75160In formula, R D1 ~R D246 It has the structure defined in List 9 below. [ka] JPEG0007927427000058.jpg188160JPEG0007927427000059.jpg203160JPEG0007927427000060.jpg137160

[0079] In some embodiments, the compound is the same as the compound of formula Ir(L A )(L B )2 or Ir(L A )2(L B ) has, in the formula, the L B The ligand is L B1 , L B2 , L B18 , L B28 , L B38 , LB108 , L B118 , L B122 , L B124 , L B126 , L B128 , L B130 , L B132 , L B134 , L B136 , L B138 , L B140 , L B142 , L B144 , L B156 , L B158 , L B160 , L B162 , L 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 is selected from the group consisting of.

[0080] In some embodiments, the compound has the formula Ir(L A ) (L B )2 or Ir(L A )2(L B ), wherein the L B ligand is L B1 , L B2 , L B18 , L B28 , L B38 , L B108 , LB118 , 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 B264 , L B265 , L B266 , L B267 , L B268 , L B269 , and L B270 It is selected from the group consisting of the following.

[0081] In some embodiments, the compound is the same as the compound of formula Ir(L A )2(L Cj-I ) or Ir(L A )2(L Cj-II ) has, in the formula, ligand L Cj-I and L Cj-II The corresponding R 201 and R 202 However, the following structure: R D1 , R D3 , R D4 , R D5 , R D9 , R D10 , R D64 , 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 , RD81 , R D87 , R D88 , R D89 , R D93 , R D116 , R D164 , 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 D645 , and R D190 L is defined as one of the following. Cj-I and L Cj-II Selected from a group consisting of ligands.

[0082] In some embodiments, the compound is the same as the compound of formula Ir(L A )2(L Cj-I ) or Ir(L A )2(L Cj-II ) has, in the formula, ligand L Cj-I and L Cj-II The corresponding R 201 and R 202 However, the following structure: R D1 , R D3 , R D4 , R D5 , R D9 , R D64 , R D22 , R D43 , R D50 , R D78 , R D116 , R D118 , R D133 , R D134 , R D135 , R D136 , R D143 , R D144 , R D145 , R D146 , R D149 , R D151 , RD154 , R D155 , and R D190 L is defined as one of the following. Cj-I and L Cj-II Selected from a group consisting of ligands.

[0083] In some embodiments, the compound is the same as the compound of formula Ir(L A )2(L C ) has, in the formula, L A L can be any structure defined in List 3, C The following group of structures is selected from the list 10 below. [ka] JPEG0007927427000062.jpg56160

[0084] In some embodiments, the compound is selected from the group consisting of structures defined in List 11 below. [ka] JPEG0007927427000064.jpg204160JPEG0007927427000065.jpg164160

[0085] In some embodiments, the compound has a structure selected from the following: [ka] JPEG0007927427000067.jpg4170In formula, M 1 is either Pd or Pt; Rings E and F are independently 5-membered or 6-membered carbon rings or heterorings; Z 2 and Z 3 Each of these is independently either C or N; K 1 and K 2Each is independently selected from the group consisting of direct bonds, O, and S; K 1 and K 2 At least one of them is a direct bond; L 1 , L 2 , and L 3 Each of these is independently selected from the group consisting of direct bond, no bond, O, S, CR'R'', SiR'R'', BR', and NR'; L 1 , L 2 , and L 3 At least one of these exists; X 1 , X 2 , X 3 , and X 4 Each of these is independently either C or N; Y 1 and Y 2 These are O, S, and NR, which are independent of each other. Y , and CR Y R Y’ Selected from the group consisting of; Y 3 , NR Y and CR Y R Y’ Selected from the group consisting of; R E and R F Each of these independently represents the maximum number of possible substitutions from a thing, or no substitutions; R, R', R E , R F , R Y , and R Y’ Each of these substituents is independently selected from the group consisting of hydrogen or preferred general substituents as defined herein; Two substituents can bond or condense with each other to form a chemically possible ring.

[0086] In some embodiments of formulas IIa to IIc, both ring E and ring F are six-membered aromatic rings.

[0087] In some embodiments of formulas IIa to IIc, ring F is a 5-membered or 6-membered heteroaromatic ring.

[0088] In some embodiments of formulas IIa to IIc, L 1 It is either O or CR'R".

[0089] In some embodiments of formulas IIa to IIc, Z 2 N is Z 1 C is C.

[0090] In some embodiments of formulas IIa to IIc, Z 2 C is Z 1 This is N.

[0091] In some embodiments of formulas IIa to IIc, L 2 This is a direct bond.

[0092] In some embodiments of formulas IIa to IIc, L 2 This is NR'.

[0093] In some embodiments of formulas IIa to IIc, K 1 and K 2 These are all direct connections.

[0094] In some embodiments of formulas IIa to IIc, X 3 ~X 5 All of these are C.

[0095] In some embodiments of formulas IIa to IIc, the compound is selected from the group consisting of structures in the following List 12. [ka] JPEG0007927427000069.jpg210157In formula, R XThis is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R G This represents the maximum number of possible substitutions from a thing, or the absence of substitutions; R G Each of these substituents is independently selected from the group consisting of hydrogen or preferred general substituents as defined herein.

[0096] In some embodiments, the compound has the structure of formula IIa, In the formula, the ligand: [ka] However, L A’ And ligand: [ka] However, L B’ and; L A’ The following is selected from the group consisting of structures defined in List 13. [ka] JPEG0007927427000073.jpg218153JPEG0007927427000074.jpg224151JPEG0007927427000075.jpg216152 JPEG0007927427000076.jpg219152JPEG0007927427000077.jpg227152JPEG0007927427000078.jpg221153 JPEG0007927427000079.jpg222152JPEG0007927427000080.jpg108152Here, R1~R307 have the structure defined below. [ka] JPEG0007927427000082.jpg205160JPEG0007927427000083.jpg182160JPEG0007927427000084.jpg207160JPEG0007927427000085.jpg208160JPEG0007927427000086.jpg196160JPEG0007927427000087.jpg200160JPEG0007927427000088.jpg204160JPEG0007927427000089.jpg192160JPEG0007927427000090.jpg55160Here, L B’ The following is selected from the group consisting of structures defined in List 14. [ka] JPEG0007927427000092.jpg172160 JPEG0007927427000093.jpg196160 JPEG0007927427000094.jpg205160 JPEG0007927427000095.jpg199160 JPEG0007927427000096.jpg196160 JPEG0007927427000097.jpg204160 JPEG0007927427000098.jpg178160 Here, Ph is phenyl.

[0097] In some embodiments, the compound is selected from the group consisting of structures in List 15 as defined below. [ka] JPEG0007927427000100.jpg206160JPEG0007927427000101.jpg188160JPEG0007927427000102.jpg82160

[0098] In some embodiments, the first ligand L of formula I described herein ACompounds having may be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. In this specification, deuterated percentage has its usual meaning and includes the percentage of hydrogen atoms (e.g., positions that are hydrogen, deuterium, or halogens) that can be substituted for deuterium atoms.

[0099] 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.

[0100] In some embodiments, the OLED includes an anode, a cathode, and a first organic layer disposed between the anode and the cathode. The first organic layer comprises a first ligand L of formula I as described herein. A It contains compounds that include [specific compounds].

[0101] 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. In some embodiments, the organic layer contains at least one further organometallic compound in addition to the compounds described herein. In some embodiments, the organic layer contains the compound at a lower concentration than the further organometallic compound. In some embodiments, the organic layer contains the compounds described herein, which are produced from the further organometallic compound. In some embodiments, the compound is produced by handling the further organometallic compound in air. In other embodiments, the compound is produced from the further organometallic compound during sublimation. In some embodiments, the organic layer contains the compound and the further organometallic compound, and the compound is sublimated from the same source as the further organometallic compound. In some embodiments, the organic layer contains the compounds described herein at a volume concentration of less than 3%. In other embodiments, the concentration is less than 2% in the organic layer, in other cases less than 1%, and in other cases less than 0.5%.

[0102] 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.

[0103] In some embodiments, the organic layer may further include a host, the host comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0104] In some embodiments, the host can be selected from a group of hosts selected from the following group: [ka] [ka]

[0105] In some embodiments, the organic layer may further include a host, the host of which includes a metal complex.

[0106] 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.

[0107] 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.

[0108] In some embodiments, the light-emitting region is the first ligand L of formula I described herein. A It may contain compounds that include the following:

[0109] 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.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] In some embodiments, the consumer product is an OLED having 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 formula I as described herein. A This includes OLEDs that can contain compounds containing the above.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] In other embodiments, compositions comprising the compounds described herein are also disclosed.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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] [ka]

[0142] 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. xThis 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.

[0143] Examples of aromatic amine derivatives used in HIL or HTL include, but are not limited to, the general structures shown below. [ka]

[0144] 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.

[0145] 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 ).

[0146] 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.

[0147] 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.

[0148] 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]

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] In another embodiment, Met is selected from Ir and Pt. In a further embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0154] 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.

[0155] 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.

[0156] 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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[0157] 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. 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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[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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, 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 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.

[0163] 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.

[0164] 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]

[0165] 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.

[0166] 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 compounds to be deuterated 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.

[0167] 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.

[0168] E. Experimental Data L A1(190)(109)(109)(109)(3)-L B Composition of 9(109)(3)(109)(109)

[0169] Platinum, [9-[4-(1,1-dimethylethyl)-2-pyridinyl-κN]-2-[3-(1,1-dimethylethyl)-2,3-dihydro-5-[3-([1,1':3':1”-terphenyl]-2'-yl-2,2”,3,3”,4,4”,5,5”,6,6”-d10)-1H-benzimidazole-1-yl-κC2]phenoxy-κC6]-9H-carbazolato(4-)-κC1]-,(SP-4-4)-(CAS:2417635-40-4,100mg,0.1 mmol) was dissolved in dichloromethane (DCM, 50 mL) and cooled to 0°C. A solution of m-chloroperbenzoic acid (mCPBA, 40 mg, 0.2 mmol, active oxidizing agent) in DCM (100 mL) was added dropwise with stirring, and the mixture was heated to room temperature. The reaction mixture was concentrated under vacuum and subjected to chromatography with SiO2 (1:1 DCM:heptane) to obtain the product as a pale yellow solid in approximately 30% yield. Table 1: Photoluminescence spectral characteristics

[0170] [Table 1] Compound L A 1(190)(109)(109)(109)(3)-L B 9(109)(3)(109)(109) efficiently exhibited deep blue phosphorescence.

[0171] Device experiment: The following compounds were used to fabricate the device, and the device was then tested. JPEG0007927427000140.jpg87160

[0172] An OLED was grown on a glass substrate pre-coated with an indium tin oxide (ITO) layer having a sheet resistance of 15 Ω / sq. Prior to the deposition or coating of the organic layer, the glass substrate was degreased with a solvent, then treated with oxygen plasma at 50 W and 100 mTorr for 1.5 minutes, and then treated with UV ozone for 5 minutes.

[0173] The devices in Table 2 were subjected to high vacuum (<10 -6 The devices were fabricated by Torr (Torr) and thermal deposition. The anode electrode was made of 750 Å indium tin oxide (ITO). An example device had, in order from the ITO surface, an organic layer consisting of a 100 Å thick layer of compound 1 (HIL), a 250 Å layer of compound 2 (HTL), a 50 Å layer of compound 3 (EBL), a 300 Å layer of compound 3 (EML) doped with 30% compound 4 and 12% light-emitting material, a 50 Å layer of compound 4 (HBL), a 300 Å layer of compound 5 (ETL) doped with 35% compound 6, and a 10 Å layer of compound 5 (EIL), as well as a 1,000 Å Al (cathode). Immediately after fabrication using a moisture getter in a package, the device was sealed in a nitrogen glove box (<1 ppm H2O and O2) with a glass lid sealed with epoxy resin. Doping percentages are expressed as volume percentages. 10mA / cm 2 In this case, the light source L A 1(190)(109)(109)(109)(3)-L B The device performance data for 9(109)(3)(109)(109) is summarized in Table 2. [Table 2]

Claims

1. It consists of the following equation, and the first ligand L in equation Ia below Ａ A compound characterized by containing [a certain substance]. 【Chemistry 1】 【Chemistry 2】 (In the formula, Ring B is a six-membered carbon ring; Y is O; X １ is C; X ２ ~X ９ Each of them is independently C; L １ is O; R Ａ’ , R Ｂ , R Ｅ , R Ｆ and R Ｇ each independently represent the maximum number of possible substitutions on the parent moiety, or represent no substitution; R Ａ１ , R Ａ’ , R Ｂ , R Ｅ , R Ｆ , and R Ｇ Each of these is independently a substituent selected from the group consisting of hydrogen, deuterium, fluorine, or alkyl, cycloalkyl, silyl, aryl, and heteroaryl compounds.

2. R Ａ１ , R Ａ’ , R Ｂ , R Ｅ , R Ｆ , and R Ｇ The compound according to claim 1, wherein each substituent is independently selected from the group consisting of hydrogen, or deuterium, fluorine, alkyl, cycloalkyl, aryl, and heteroaryl.

3. A compound comprising the following formula and containing the first ligand L A of the following formula Ia. 【Transformation 3】 【Chemistry 4】 (In the formula, L1 is O; RE, RF, and RG each independently represent the maximum number of possible substitutions from a mono, or no substitutions; RE, RF, and RG are each independently hydrogen, deuterium, fluorine; or substituents selected from the group consisting of alkyl, cycloalkyl, silyl, aryl, and heteroaryl; The first ligand L represented by the above formula Ia Ａ However, the following group is selected. 【Transformation 5】 Here, R1 to R307 are defined as follows: 【Transformation 6】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

4. A compound characterized by being selected from the group consisting of the following. 【Transformation 7】

5. Organic light-emitting devices (OLEDs), A-scatter, Cathode and, It includes an organic layer disposed between the anode and the cathode, The OLED is characterized in that the organic layer contains the compound described in any one of claims 1 to 4.

6. The OLED according to claim 5, wherein the organic layer further comprises a host, the host comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, indlocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indlocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

7. The OLED according to claim 6, wherein the host is selected from the group consisting of the following. 【Transformation 8】 【Chemistry 9】

8. A consumer product including an organic light-emitting device (OLED), wherein the organic light-emitting device (OLED) is A-scatter, Cathode and, It includes an organic layer disposed between the anode and the cathode, A consumer product characterized in that the organic layer contains the compound described in any one of claims 1 to 4.

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