Organic electroluminescent material and device

Abstract

To provide a compound that is useful as an emissive compound in an organic light emitting device.SOLUTION: There is provided a material for use in organic light emitting device, which includes a ligand LA of the following formula. (In the formula, A1 represents F, CH2F, CHF2, or CF3, R1 represents alkyl, cycloalkyl, or F, R2 represents alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, R3-R5 each represent H, D, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or F, and R6 represents H, alkyl, or cycloalkyl.)SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 62 / 888,081, filed August 16, 2019, the disclosure of which is incorporated herein by reference in its entirety.

[0002] The present disclosure relates generally to organometallic compounds and compositions and their various uses, including as light emitters in devices such as organic light emitting diodes and related electronic devices. More particularly, the present disclosure relates to acetylacetonate-related compounds and compositions and their uses in electronic devices. [Background technology]

[0003] Optoelectronic devices that utilize organic materials are becoming increasingly desirable for a variety of reasons. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as flexibility, may make them well suited for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over traditional materials.

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

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

[0006] In one aspect, the present disclosure provides a ligand L of formula I: A The present invention provides a compound comprising: [ka] Formula I In the formula, A 1 is fluorine, CH2F, CHF2, or CF3; R 1 is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R 2 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R 2 does not contain fluorine; R 3 , R 4 , and R 5 are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R 6 is hydrogen, alkyl, or cycloalkyl; the ligand L A is coordinated to a metal M; the metal M can be coordinated to other ligands; the ligand L Acan be combined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be combined or fused together to form a ring, if chemically possible.

[0007] In another aspect, the disclosure provides compositions of the disclosed compounds.

[0008] In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound of the present disclosure.

[0009] In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of the present disclosure. [Brief description of the drawings]

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

[0011] [Diagram 2] FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer. A. Terminology DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Unless otherwise stated, the following terms used herein are defined as follows.

[0013] As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" can actually be quite large. Small molecules can include repeat units in some circumstances. For example, the use of long chain alkyl groups as a substituent does not remove a molecule from the "small molecule" class. Small molecules can be incorporated into polymers, for example, as pendant groups on a polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of dendrimers, which consist of a series of chemical shells built on the core moiety. The core moiety of a dendrimer can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

[0014] As used herein, "top" means furthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as "disposed over" a second layer, the first layer is disposed 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 "disposed over" an anode, even though there may be various organic layers in between.

[0015] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium, either in the form of a solution or suspension.

[0016] A ligand may be referred to as "photoactive" if it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" if it is believed that the ligand does not contribute to the photoactive properties of the emissive material, although the ancillary ligand may modify the properties of the photoactive ligand.

[0017] As used herein, and as generally understood by those skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IPs) are measured as negative energies relative to the vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (a 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. A "higher" HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower" HOMO or LUMO energy level.

[0018] As used herein, as generally understood by those skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Since work functions are generally measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. In a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being further away from the vacuum level in a downward direction. Thus, the definition of the HOMO and LUMO energy levels follows a different convention than work functions.

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

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

[0021] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R sOr -C(O)-OR s ) group.

[0022] The term "ether" means -OR s Refers to the base.

[0023] The terms "sulfanyl" and "thioether" are used interchangeably, and -SR s Refers to the base.

[0024] The term "sulfinyl" refers to -S(O)-R s Refers to the base.

[0025] The term "sulfonyl" means -SO2-R s Refers to the base.

[0026] The term "phosphino" refers to -P(R s ) 3 groups, each R s may be the same or different.

[0027] The term "silyl" means -Si(R s ) 3 groups, each R s may be the same or different.

[0028] The term "boryl" means -B(R s ) groups or their Lewis adducts -B(R s ) 3 groups, R s may be the same or different.

[0029] In each of the above, R s can be hydrogen or 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, and combinations thereof. sis selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0030] The term "alkyl" refers to and includes both straight and branched chain alkyl groups. Preferred alkyl groups contain from 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. Additionally, the alkyl groups may be optionally substituted.

[0031] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing from 3 to 12 ring carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl groups may be optionally substituted.

[0032] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Furthermore, the heteroalkyl group or the heterocycloalkyl group may be optionally substituted.

[0033] The term "alkenyl" refers to and includes both straight-chain and branched-chain 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. The term "heteroalkenyl" as used herein refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkenyl, cycloalkenyl, or heteroalkenyl groups may be optionally substituted.

[0034] The term "alkynyl" refers to and includes both straight and branched chain alkyne groups. An alkynyl group is essentially an alkyl group that contains at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those that contain 2 to 15 carbon atoms. Additionally, said alkynyl groups may be optionally substituted.

[0035] The terms "aralkyl" and "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group, which may be optionally substituted.

[0036] 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 may be used interchangeably with heteroaryl. Preferred hetero non-aromatic cyclic groups are those containing 3-7 ring atoms and contain at least one heteroatom, including cyclic amines such as morpholino, piperidino, pyrrolidino, and cyclic ethers / thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Furthermore, the heterocyclic groups may be optionally substituted.

[0037] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycyclic ring can have two or more rings with two carbons shared between two adjacent rings (the rings being "fused"), at least one of the rings being an aromatic hydrocarbyl group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing 6 to 30 carbon atoms, preferably those containing 6 to 20 carbon atoms, and more preferably those containing 6 to 12 carbon atoms. Aryl groups having 6 carbons, 10 carbons, or 12 carbons are particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, and are preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Furthermore, the aryl group may be optionally substituted.

[0038] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems containing at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many instances, O, S, or N are the preferred heteroatoms. Heteromonocyclic aromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings can have 1 to 6 heteroatoms. Heteropolycyclic ring systems can have two or more rings in which two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Heteropolycyclic aromatic ring systems can have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, preferably those containing 3 to 20 carbon atoms, and more preferably those containing 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, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziso ... Examples of heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, with dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza analogs thereof being preferred. Furthermore, the heteroaryl groups may be optionally substituted.

[0039] Of the aryl and heteroaryl groups listed above, the triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole groups, and their respective aza analogues, are of particular interest.

[0040] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic, aryl, and heteroaryl are independently unsubstituted or independently substituted with one or more common substituents.

[0041] In many instances, the typical substituents are 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, phosphino, boryl, and combinations thereof.

[0042] In some instances, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.

[0043] In some instances, 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.

[0044] In yet other instances, the most preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0045] The terms "substituted" and "substituted" refer to a substituent other than H attached to the relevant position (e.g., carbon or nitrogen). For example, R 1 If represents a monosubstitution, one R 1 must be other than H (i.e., a substitution). Similarly, R 1 If represents a disubstitution, R 1 must be other than H. Similarly, R 1 When R represents zero or no substitution, 1can be hydrogen at an available valence of a ring atom, as in the case of carbon atoms in benzene and nitrogen atoms in pyrrole, or simply represents nothing in the case of ring atoms with fully filled valences (e.g., nitrogen in pyridine). The maximum number of substitutions possible in a ring structure depends on the total number of available valences on the ring atoms.

[0046] As used herein, "combinations thereof" refers to one or more members of the applicable list being combined to form a known or chemically stable configuration that one of skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl, and aryl can be combined to form a halogenated aryl alkyl. In one example, the term substituted includes combinations of 2-4 of the listed groups. In another example, the term substituted includes combinations of 2-3 groups. In yet another example, the term substituted includes combinations of 2 groups. Preferred combinations of substituents include those that contain up to 50 atoms that are not hydrogen or deuterium, or those that contain up to 40 atoms that are not hydrogen or deuterium, or those that contain up to 30 atoms that are not hydrogen or deuterium. In many examples, preferred combinations of substituents include up to 20 atoms that are not hydrogen or deuterium.

[0047] The designation "aza" in the fragments described herein, such as aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the CH groups in each aromatic ring can be replaced by a nitrogen atom, for example, but not by way of limitation, azatriphenylene includes both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of skill in the art can easily imagine other nitrogen analogs of the above-mentioned aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0048] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, International Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. 2011 / 0037057, the contents of which are incorporated by reference in their entirety, describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Tetrahedron 2015, 71, 1425-30 (Ming Yan et al.) and Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65 (Atzrodt et al.), the contents of which are incorporated by reference in their entirety, which describe efficient routes for the deuteration of methylene hydrogens in benzylamines and the replacement of aromatic ring hydrogens with deuterium, respectively.

[0049] It is understood that when a molecular fragment is described as being a substituent or attached to another moiety, the name may be described as being the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). Different designations of the substituents or attached fragments are considered equivalent herein.

[0050] In some cases, the adjacent substituents of a pair can be optionally bonded or fused to form a ring. Preferred rings are 5-, 6-, or 7-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 related substituents can be on the same ring adjacent to each other, or on the two adjacent rings with the two nearest available substitutable positions, such as 2- and 2'-positions in biphenyl and 1- and 8-positions in naphthalene, as long as a stable fused ring system can be formed. B. Compounds of the Present Disclosure

[0051] In one aspect, the present disclosure provides a first ligand L of formula I: A The present invention provides a compound comprising: [ka] Formula I In the formula, A 1 is fluorine, CH2F, CHF2, or CF3; R 1 is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R 2 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R 2 does not contain fluorine; R 3 , R 4 , and R 5 are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R 6 is hydrogen, alkyl, or cycloalkyl; the ligand L A is coordinated to a metal M; the metal M can be coordinated to other ligands; the ligand L A can be combined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be combined or fused together to form a ring, if chemically possible.

[0052] In some embodiments, A 1 can be fluorine.

[0053] In some embodiments, A 1 can be CH2F, CHF2, or CF3.

[0054] In some embodiments, R 6 can be hydrogen.

[0055] In some embodiments, A 1 is R 5 can be identical to R 1 is R 3 can be identical to R 2 is R 4 can be identical to

[0056] In some embodiments, R 1 , R 2 , R 3 , and R 4 Each can be alkyl or cycloalkyl.

[0057] In some embodiments, A 1 and R 5 can each be fluorine.

[0058] In some embodiments, A 1 and R 5 can be CH2F, CHF2, or CF3, respectively.

[0059] In some embodiments, R 3 , R 4 , and R 5 Each can be alkyl.

[0060] In some embodiments, R 3 and R 4 Each can be alkyl, R 5 may be hydrogen.

[0061] In some embodiments, R 3 , R 4 , and R 5 can each be fluorine.

[0062] In some embodiments, M can be selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

[0063] In some embodiments, M can be Ir or Pt. In some embodiments, M can be Ir.

[0064] In some embodiments, the ligand L A can be selected from the group consisting of: [ka] In the formula, R 7 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, partially or fully fluorinated alkyl, and combinations thereof.

[0065] In some embodiments, the ligand L A L Az where z is an integer from 1 to 46849770; L A1 ~L A46849770 The structure of is defined as follows: [ka] [ka] [ka] [ka] In the formula, R D1 ~R D198 has the following structure: [ka] [ka] [ka] [ka]

[0066] In some embodiments, the ligand L A is selected from the group consisting of: [ka] [ka] [ka] [ka] [ka]

[0067] In some embodiments, the compound has the formula M(L A ) x (L B ) y (L C ) z wherein L A is as defined above, and L B and L C are each a bidentate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.

[0068] 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 wherein L A is as defined above; L A, L B , and L C are different from each other.

[0069] In some embodiments, the compound has the formula Pt(L A )(L B ) in which L A is as defined above; L A and L B may be the same or different.

[0070] In some embodiments, the ligand L A and L B can be linked to form a tetradentate ligand.

[0071] In some embodiments, the ligand L B and L C may each independently be selected from the group consisting of: [ka] [ka] In the formula, each Y 1 ~Y 13 is independently selected from the group consisting of carbon and nitrogen; Y' is BR e , N.R. e , P.R. e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , and GeR e R f R e and R f may be fused or linked to form a ring; each R a , R b , R c , and R d independently represent monosubstitution to the maximum number of possible substitutions; each R a , R b , R c , Rd , R e , and R f is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; R a , R b , R c , and R d Any two adjacent substituents of can be fused or linked to form a ring or to form a multidentate ligand.

[0072] In some embodiments, the ligand L B and L C may each independently be selected from the group consisting of: [ka] [ka]

[0073] In some embodiments, L B can be selected from the group consisting of: [ka] [ka] [ka] [ka] In the formula, j is an integer from 1 to 400, and each L Bj In the formula, the substituent R E and G are defined as follows: [ka] [ka] [ka] In the formula, R 1 ~R 20 has the following structure: [ka] [ka] In the formula, G 1 ~G 20 has the following structure: [ka]

[0074] In some embodiments, the compound has the formula Ir(L AZ )(L Bj-k )2, L AZ is L as described herein. A1 ~L A46849770 and L Bj-k is L as described herein. B1-1 ~L B400-50 The structure is selected from the group consisting of:

[0075] In some embodiments, the compound is selected from the group consisting of: [ka] [ka] [ka]

[0076] C. OLEDs and Devices of the Present Disclosure In another embodiment, the present disclosure also provides an OLED device comprising a first organic layer containing a compound disclosed in the Compounds section of this disclosure.

[0077] In some embodiments, an OLED includes an anode, a cathode, and a first organic layer disposed between the anode and the cathode. The first organic layer comprises a ligand L of Formula I: A The compound may include a compound comprising: [ka] Formula I In the formula, A 1 is fluorine, CH2F, CHF2, or CF3; R 1 is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R 2 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R 2 does not contain fluorine; R 3 , R 4 , and R 5 are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R 6 is hydrogen, alkyl, or cycloalkyl; the ligand L A is coordinated to a metal M; the metal M can be coordinated to other ligands; the ligand L A can be combined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be combined or fused together to form a ring, if chemically possible.

[0078] In some embodiments, the organic layer can be an emissive layer and the compounds described herein can be emissive or non-emissive dopants.

[0079] In some embodiments, the organic layer can further include a host, the host including a triphenylene, including a benzo-fused thiophene or a benzo-fused furan, and any substituents in the host can be independently selected from the group consisting of Cn H 2n+1 , O.C. 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-fused substituent selected from the group consisting of, or can be unsubstituted, n is 1 to 10, and Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0080] In some embodiments, the organic layer can further include a host, the host comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

[0081] In some embodiments, the host may be selected from the group of hosts selected from the group consisting of: [ka] [ka] [ka]

[0082] In some embodiments, the organic layer can further comprise a host, wherein the host comprises a metal complex.

[0083] In some embodiments, the compound described herein can be a sensitizer, and the device can further include an acceptor, and the acceptor can be selected from a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0084] In yet another embodiment, the OLED of the present disclosure can also include a light-emitting region that includes a compound disclosed in the Compounds section of this disclosure.

[0085] In some embodiments, the emissive region comprises a ligand L of formula I: A The compound may include a compound comprising: [ka] Formula I In the formula, A 1 is fluorine, CH2F, CHF2, or CF3; R 1 is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R 2 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R 2 does not contain fluorine; R 3 , R 4 , and R 5 are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R 6 is hydrogen, alkyl, or cycloalkyl; the ligand L A is coordinated to a metal M; the metal M can be coordinated to other ligands; the ligand L Acan be combined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be combined or fused together to form a ring, if chemically possible.

[0086] In some embodiments of the emissive region, the compound can be an emissive dopant or a non-emissive dopant. In some embodiments, the emissive region further comprises a host, the host comprising at least one group selected from the group consisting of metal complexes, triphenylenes, carbazoles, indolocarbazoles, dibenzothiophenes, dibenzofurans, dibenzoselenophenes, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylenes, aza-carbazoles, aza-indolocarbazoles, aza-dibenzothiophenes, aza-dibenzofurans, aza-dibenzoselenophenes, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene). In some embodiments, the emissive region further comprises a host, the host selected from the group of hosts described above.

[0087] In yet another aspect, the present disclosure also provides a consumer product comprising an 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 present disclosure.

[0088] 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, the organic layer comprising a ligand L of Formula I: A The present invention includes an OLED that can include a compound comprising: [ka] Formula I In the formula, A 1 is fluorine, CH2F, CHF2, or CF3; R 1is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R 2 is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R 2 does not contain fluorine; R 3 , R 4 , and R 5 are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R 6 is hydrogen, alkyl, or cycloalkyl, and the ligand L A is coordinated to a metal M; the metal M can be coordinated to other ligands; the ligand L A can be combined with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be combined or fused together to form a ring, if chemically possible.

[0089] In some embodiments, the consumer product can be one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor illumination and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays aligned together, a theater or stadium screen, a light therapy device, and a sign.

[0090] In general, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons migrate to the oppositely charged electrode, respectively. When an electron and hole localize on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. Light is emitted via a photoemissive mechanism when the exciton relaxes. In some cases, the exciton may be localized on an excimer or exciplex. Non-radiative mechanisms such as thermal relaxation may also occur, but are generally considered undesirable.

[0091] Some OLED materials and configurations are described in US Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated by reference in their entireties.

[0092] Early OLEDs used emissive molecules that emitted light from their singlet state ("fluorescence"), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs on a time frame of less than 10 nanoseconds.

[0093] More recently, OLEDs have been demonstrated that have emissive materials that emit light from triplet states ("phosphorescence"). Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, Vol. 395, No. 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, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entireties. Phosphorescence is described in further detail in U.S. Pat. No. 7,279,704, columns 5-6, which are incorporated by reference.

[0094] FIG. 1 shows an organic light-emitting device 100. The figures are not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole-injection layer 120, a hole-transport layer 125, an electron-blocking layer 130, an emissive layer 135, a hole-blocking layer 140, an electron-transport layer 145, an electron-injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. The cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US Pat. No. 7,279,704, columns 6-10, which are incorporated by reference.

[0095] Further examples are available for each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0096] FIG. 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 layers described, in order. Because the most common OLED configuration has the cathode disposed above the anode, and device 200 has cathode 215 disposed below anode 230, device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides an example of how some layers may be omitted from the structure of device 100.

[0097] The simple layer structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and it is understood that the embodiments of the present disclosure may be used in conjunction with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be achieved 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 the various layers as including a single material, it is understood that combinations of materials, such as mixtures of hosts and dopants, or more generally mixtures, may be used. Layers may also have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include a single layer, or may further include multiple layers of different organic materials, such as those described with respect to Figures 1 and 2.

[0098] Structures and materials not specifically described may be used, such as OLEDs (PLEDs) composed of polymeric materials such as those disclosed in U.S. Patent No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. As a further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. 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 the mesa structures described in U.S. Patent No. 6,091,195 to Forrest et al. and / or the recessed structures described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0099] 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 evaporation, such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety, inkjet, organic vapor phase deposition (OVPD), such as those described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and organic vapor jet printing (OVJP), such as those described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin-coating and other solution-based processes. Solution-based processes are preferably carried out in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include patterning associated with some of the deposition methods such as deposition through masks, cold welding, and inkjet and organic vapor jet printing (OVJP), such as those described in U.S. Patent Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety. Other methods may be used. The material to be deposited may be modified to be compatible with the particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents with 20 or more carbons may be used, with 3-20 carbons being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures, as asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

[0100] Devices fabricated according to embodiments of the present 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, etc. The barrier layer may be deposited on, under or next to the substrate, the electrodes, or on any other portion of the device, including the edges. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferred barrier layers include mixtures of polymeric and non-polymeric materials, as described in U.S. Pat. No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entireties. To be considered a "mixture", the polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and / or simultaneously. The weight ratio of polymeric to non-polymeric materials can be in the range of 95:5 to 5:95. The polymeric and non-polymeric materials can be made from the same precursor materials. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0101] Devices made according to embodiments of the present 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, lighting devices (such as discrete light source devices or lighting panels) that can be utilized by end-user product manufacturers. Such electronic component modules can optionally include driving electronics and / or power sources. Devices made according to embodiments of the present disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Disclosed are consumer products that include OLEDs that include compounds of the present disclosure in the organic layer of the OLED. Such consumer products include any type of product that includes one or more light sources and / or one or more visual displays of some kind. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, 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 diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays aligned together, theater or stadium screens, phototherapy devices, and signage. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices made according to the present disclosure. Many of the devices are intended for use within a temperature range that is comfortable for humans, such as 18 degrees Celsius to 30 degrees Celsius, and more preferably room temperature (20-25°C), but may also be used outside this temperature range, for example, between -40 degrees Celsius and +80 degrees Celsius.

[0102] Further details regarding OLEDs and the above definitions can be found in US Pat. No. 7,279,704, which is incorporated by reference in its entirety.

[0103] 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 the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.

[0104] In some embodiments, the OLED has one or more properties selected from the group consisting of flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

[0105] In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises 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 a lighting panel.

[0106] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, or TADF (also called E-type delayed fluorescence; see, for example, U.S. Application No. 15 / 700,352, which is incorporated by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the emissive dopant can be a racemic mixture or can be enriched in one enantiomer. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from the others). If there is more than one ligand that coordinates to the metal, in some embodiments, the ligands can all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, all of the ligands can be different from each other. This is true even in embodiments where a ligand coordinated to a metal can be bonded to other ligands coordinated to the metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, when the coordinating ligands are bonded to one another, in some embodiments, all of the ligands can be the same, while in some other embodiments, at least one of the bonded ligands can be different from the other ligands.

[0107] In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, where one or more layers in the OLED include an acceptor in the form of one or more fluorescent and / or delayed fluorescent 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 a final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can come from any or all of the sensitizer, the acceptor, and the final emitter.

[0108] In accordance with other aspects, compositions including the compounds described herein are also disclosed.

[0109] The OLEDs disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer, and in some embodiments, the compound can be an emissive dopant, and in other embodiments, the compound can be a non-emissive dopant.

[0110] In yet another aspect of the present disclosure, a composition is described that includes the novel compounds disclosed herein. The composition may also include one or more components selected from the group consisting of a solvent, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material disclosed herein.

[0111] The present disclosure encompasses any chemical structure that includes the novel compounds of the present disclosure, or monovalent or polyvalent variants thereof. In other words, the compounds of the present invention, or monovalent or polyvalent variants thereof, can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermolecules). As used herein, a "monovalent variant of a compound" refers to a moiety that is identical to the compound, except that one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. As used herein, a "polyvalent variant of a compound" refers to a moiety that is identical to the compound, except that more than one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. In the example of a supramolecule, the compounds of the present invention can also be incorporated into the supramolecular complex without a covalent bond. D. Combinations of Compounds of the Present Disclosure with Other Materials

[0112] The materials described herein as useful for a particular layer in an organic light-emitting device can be used in combination with a wide variety of other materials present in the device.For example, the emissive dopants disclosed herein can be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present.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. a) Conductive dopants:

[0113] The charge transport layer is doped with a conductive dopant to significantly change the density of charge carriers and therefore its conductivity. The conductivity can be increased by creating charge carriers in the matrix material or, depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant and an n-type conductive dopant is used in the electron transport layer.

[0114] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials. EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012 [ka] [ka] b) HIL / HTL:

[0115] The hole injection / transport material used in the present disclosure is 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 fluorocarbons; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembly monomers derived from compounds such as phosphonic acid and silane derivatives; MoO xp-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds.

[0116] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structure: [ka]

[0117] Ar 1 From Ar 9each of the above represents a group consisting of aromatic hydrocarbon ring 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, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazole, and aromatic heterocyclic compounds such as sazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which may be of the same or different types and which are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Each Ar can be unsubstituted or substituted with substituents 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, phosphino, and combinations thereof.

[0118] In one embodiment, 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 has the same groups as defined above.

[0119] Examples of metal complexes used in the HIL or HTL include, but are not limited to, those of the general formula: [ka] where Met is a metal that may have an atomic weight greater than 40; 101 -Y 102 ) is a bidentate ligand, and Y 101 and Y 102 is independently selected from C, N, O, P, and S; L 101 is an ancillary ligand; k' is an integer value from 1 to the maximum number of ligands that may be bound to the metal; and k'+k'' is the maximum number of ligands that may be bound to the metal.

[0120] In one embodiment, (Y 101 -Y 102 In another embodiment, (Y 101 -Y 102 In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex is + For the / Fc couple, it has a minimum oxidation potential of less than about 0.6 V in solution.

[0121] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose 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] c) EBL:

[0122] Electron blocking layers (EBLs) can be used to reduce the number of electrons and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Blocking layers can also be used to confine emission to desired regions of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group used as one of the hosts described below. d) Host:

[0123] 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 contain 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 may be used as long as the triplet energy of the host is greater than that of the dopant. Any host material may be used with any dopant as long as the triplet criteria are met.

[0124] Examples of metal complexes used as host materials preferably have the general formula: [ka] where Met is a metal; 103 -Y 104 ) is a bidentate ligand, and Y 103 and Y 104 is independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value from 1 to the maximum number of ligands that may be bound to the metal; and k'+k'' is the maximum number of ligands that may be bound to the metal.

[0125] In one embodiment, the metal complex is a complex: [ka] where (ON) is a bidentate ligand with the metal coordinated to atoms O and N.

[0126] In another embodiment, Met is selected from Ir and Pt. 103 -Y 104 ) is a carbene ligand.

[0127] In one embodiment, the host compound is selected from the group consisting of aromatic hydrocarbon ring 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, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazoline, and aromatic heterocyclic compounds such as benzofuropyridine, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which are the same or different groups and which have 2 to 10 cyclic structural units bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic cyclic group. Each option within each group can be unsubstituted or 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, phosphino, and combinations thereof.

[0128] In one embodiment, the host compound contains at least one of the following groups in the molecule: [ka] [ka] In the formula, R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, 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 is independently selected from C (including CH) or N. 101 and Z 102 is independently, NR 101 , O, or S.

[0129] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose 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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[0130] One or more additional emitter dopants can be used with the compounds of the present disclosure.The examples of the additional emitter dopants are not particularly limited, and any compound can be used as long as the compound is typically used as an emitter material.Examples of suitable emitter materials include, but are not limited to, compounds that can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e. TADF (also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0131] Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose 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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[0132] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the emissive layer. The presence of such a blocking layer in the device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine 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 emitter 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 of the hosts closest to the HBL interface.

[0133] In one embodiment, the compounds used in the HBL contain the same molecules or the same functional groups as those used in the hosts described above.

[0134] In another embodiment, the compound used in the HBL comprises at least one of the following groups in the molecule: [ka] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3. g)ETL:

[0135] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is typically used to transport electrons.

[0136] In one embodiment, the compound used in the ETL contains at least one of the following groups in the molecule: [ka] In the formula, R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. 1 From Ar 3 has the same definition as that of Ar mentioned above. k is an integer from 1 to 20. X 101 From X 108 is selected from C (including CH) or N.

[0137] In another embodiment, the metal complex used in the ETL comprises, but is not limited to, the following general formula: [ka] In the formula, (ON) or (NN) is a bidentate ligand having a metal coordinated to the atoms O, N or N, N; 101 is another ligand; and k' is an integer value between 1 and the maximum number of ligands that can be bound to the metal.

[0138] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose 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] h) Charge Generation Layer (CGL)

[0139] In tandem or stacked OLEDs, the CGL plays an important role in performance and consists of n-doped and p-doped layers for the injection of electrons and holes, respectively. The electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively, after which the bipolar current gradually reaches a steady state. Typical CGL materials contain n-type and p-type conductive dopants used in the transport layers.

[0140] In any of the above-mentioned compounds used in each layer of an OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any of the specifically mentioned substituents, such as but not limited to methyl, phenyl, pyridyl, etc., can be their non-deuterated, partially deuterated, and fully deuterated versions. Similarly, the classes of substituents, such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc., can be their non-deuterated, partially deuterated, and fully deuterated versions.

[0141] It is understood that the various embodiments described herein are merely exemplary and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. Thus, the invention as claimed may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It is understood that the various theories of why the invention works are not intended to be limiting. E. Experimental Data

[0142] Material synthesis

[0143] Example 1

[0144] Compound Ir(LB86-9 )2(L A7762396 Synthesis of [ka] Di-μ-chloro-tetrakis-[(1-(4-(tert-butyl)naphthalen-2-yl)-1′-yl)-8-isobutylbenzo-[4,5]thieno[2,3-c]pyridin-2-yl]diiridium(III): A solution of 1-(4-(tert-butyl)naphthalen-2-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridine (130 g, 306 mmol, 1.8 equiv.) in 2-ethoxyethanol (2420 mL) and water (580 mL) was sparged with nitrogen for 1 h. Iridium(III) chloride hydrate (63 g, 170 mmol, 1.0 equiv.) was added and the reaction mixture was heated to 90° C. for 36 h. 1 H-NMR analysis indicated the reaction was complete. The reaction mixture was cooled to 35° C. and the resulting solid was filtered and washed with methanol (4×250 mL). The solid was dried under vacuum at 40° C. to give di-μ-chloro-tetrakis-[(1-(4-(tert-butyl)naphthalen-2-yl)-1′-yl)-8-isobutylbenzo-[4,5]thieno[2,3-c]pyridin-2-yl]diiridium(III) (153.2 g, 93% yield) as a red solid.

[0145] [ka] Bis[1-((4-(tert-butyl)naphthalen-2-yl)-1'-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]-(1,1,1-trifluoro-2,2,6-trimethylheptane-3,5-dionato-k2O,O')iridium(III): 1,1,1-trifluoro-2,2,6-trimethyl-heptane-3,5-dione (1.42g, 6 A solution of di-μ-chloro-tetrakis-[(1-(4-(tert-butyl)naphthalen-2-yl)-1′-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]diiridium(III) (5.0 g, 2.3 mmol, 1.0 equiv.) in a 1:1 mixture of dichloromethane and methanol (70 mL) was added via syringe. The reaction mixture was sparged with nitrogen for 15 minutes. Powdered potassium carbonate (1.2 g, 8.3 mmol, 3.6 equiv.) was added and the reaction mixture was heated at 40° C. for 16 hours in a flask wrapped in foil to protect from light. 1 H-NMR analysis indicated the reaction was complete. The cooled mixture was poured into methanol (300 mL) and the resulting solid was filtered and washed with methanol (150 mL). The red solid was diluted with water (150 mL) and the slurry was stirred for 15 min. The suspension was filtered, washed successively with water (150 mL) and methanol (2×25 mL), and dried under vacuum at 45° C. for 2 h. The red solid (~5 g) was dry-loaded onto basic alumina (122 g) and chromatographed on an Interchim automated chromatography system (220 g silica gel cartridge) eluting with a 10-40% gradient of dichloromethane in hexanes. The purest product fractions were combined and concentrated under reduced pressure. The residual solid (3.8 g) was triturated with methanol (10 volumes) at 40° C., filtered, and dried under vacuum at 45° C. for 2 hours to give bis[1-((4-(tert-butyl)naphthalen-2-yl)-1'-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]-(1,1,1-trifluoro-2,2,6-trimethylheptane-3,5-dionato-kO,O')iridium(III) (3.72 g, 63% yield, 99.7% UPLC purity) as a red solid.

[0146] Example 2

[0147] Compound Ir(L B91-27 )2(L A7762396 Synthesis of [ka] Di-μ-chloro-tetrakis[(4-(4-(tert-butyl)naphthalen-2-yl)-1′-yl)-7-methyl-6-(3,3,3-trifluoropropyl)-thieno[3,2-d]pyrimidin-3-yl]diiridium(III): A mixture of 4-(4-(tert-butyl)naphthalen-2-yl)-7-methyl-6-(3,3,3-trifluoropropyl)-thieno[3,2-d]pyrimidine (30.2 g, 70.5 mmol, 2.0 equiv.), 2-ethoxyethanol (150 mL), and water (50 mL) was sparged with nitrogen for 25 minutes. Iridium(III) chloride hydrate (11.14 g, 35.2 mmol, 1.0 equiv.) was added and sparging continued for 5 minutes. The reaction mixture was heated at 100° C. for 15 hours, at which point 1 H NMR analysis showed 95% conversion to product. The reaction mixture was cooled to room temperature, filtered, and the solid was washed with methanol (50 mL) to give di-μ-chloro-tetrakis[4-(4-(tert-butyl)naphthalen-2-yl)-1′-yl)-7-methyl-6-(3,3,3-trifluoropropyl)thieno[3,2-d]pyrimidin-3-yl]diiridium(III) (60 g, wet) as a red solid.

[0148] [ka] Bis[(4-(4-(tert-butyl)naphthalen-2-yl)-1'-yl)-6-(3,3,3-trifluoropropyl)-7-methyl-thieno[3,2-d]pyrimidin-3-yl)]-(1,1,1-trifluoro-2,2,6-trimethyl-3,5-heptanedionato-k2O,O')iridium(III): Di-μ-chloro-tetrakis[4-(4-(tert-butyl)-naphthalene)-1'-yl]-6-(3,3,3-trifluoropropyl)-7-methyl-thieno[3,2-d]pyrimidin-3-yl]-(1,1,1-trifluoro-2,2,6-trimethyl-3,5-heptanedionato-k2O,O')iridium(III) in methanol (12 mL) and dichloromethane (2 mL). A suspension of (3,3,3-trifluoropropyl)-6-(3,3,3-trifluoropropyl)thieno[3,2-d]pyrimidin-3-yl]diiridium(III) (2.5 g, 1.16 mmol, 1.0 equiv.), 1,1,1-trifluoro-2,2,6-trimethylhept-ane-3,5-dione (650 mg, 2.88 mmol, 2.5 equiv.) and powdered potassium carbonate (480 mg, 3.48 mmol, 3.0 equiv.) was heated at 40° C. for 24 hours. 1 H-NMR analysis indicated the reaction was complete. The reaction mixture was cooled to room temperature, water (10 mL) was added, and the suspension was stirred for 30 min. The suspension was filtered and the solid was washed with water (30 mL) and methanol (10 mL) and then air-dried. The red solid (3.1 g) was chromatographed on silica gel (90 g) with basic alumina (20 g) eluting with 80% dichloromethane in hexane. The fractions containing the purest product were concentrated to give bis[(4-(4-(tert-butyl)naphthalen-2-yl)-1'-yl)-6-(3,3,3-trifluoropropyl)-7-methylthieno[3,2-d]-pyrimidin-3-yl)]-(1,1,1-trifluoro-2,2,6-trimethyl-3,5-heptanedionato-kO,O')-iridium(III) (1.51 g, 51% yield, 99.6% UPLC purity) as a red solid.

[0149] Comparative Example 1 [ka] Bis[1-((4-(tert-butyl)naphthalen-2-yl)-1'-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]-(2,6-dimethyl-heptane-3,5-dionato-kO,O')iridium(III): 2,6-Dimethyl-heptane-3,5-dione (655 mg, 4.2 mmol, 3.0 equiv.) was added to a solution of di-μ-chloro-tetrakis-[(1-(4-(tert-butyl)naphthalen-2-yl)-1'-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]diiridium(III) (3.0 g, 1.40 mmol, 1.0 equiv.) in a 1:1 mixture of dichloromethane and methanol (60 mL). The reaction mixture was sparged with nitrogen for 5 minutes. Powdered potassium carbonate (775 mg, 5.6 mmol, 4.0 equiv.) was added and the reaction mixture was stirred at room temperature in a foil-wrapped flask to protect from light. After 25 hours, 1 H-NMR analysis indicated the reaction was complete. The reaction mixture was poured into methanol (150 mL) and the slurry was stirred for 30 min. The suspension was filtered and the solid was washed with methanol (3×30 mL). The crude product (3.7 g) was dissolved in dichloromethane (100 mL), dry loaded onto basic alumina (25 g) and chromatographed on an Interchim automated chromatography system (80 g, silica gel cartridge) eluting with a 0-50% gradient of dichloromethane in hexanes. The fractions containing the purest product were concentrated under reduced pressure to give bis[1-((4-(tert-butyl)naphthalen-2-yl)-1'-yl)-8-isobutylbenzo[4,5]thieno[2,3-c]pyridin-2-yl]-(2,6-dimethyl-heptane-3,5-dionato-kO,O')iridium(III) (1.75 g, 52% yield, 99.2% UPLC purity) as a red solid.

[0150] Comparative Example 2 [ka] Bis[(4-(4-(tert-butyl)naphthalene-2-yl)-1'-yl)-6-(3,3,3-trifluoropropyl)-7-methyl-thieno[3,2-d]pyrimidin-3-yl)]-(2,6-dimethyl-3,5-heptane-dionato-kO,O')-iridium(III): Di-μ-chloro-tetrakis[4-(4-(tert-butyl)naphthalene-2-yl)-1'-yl]-6-(3,3,3-trifluoropropyl)-7-methyl-thieno[3,2-d]pyrimidin-3-yl]-(2,6-dimethyl-3,5-heptane-dionato-kO,O')-iridium(III) in methanol (15 mL) and dichloromethane (5 mL). A suspension of (3,3,3-trifluoropropyl)-6-(3,3,3-trifluoropropyl)-1'-yl)-7-methyl-6-(3,3,3-trifluoropropyl)thieno[3,2-d]pyrimidin-3-yl]diiridium(III) (3 g (wet), est. 1.385 mmol, 1.0 equiv.), 2,6-dimethyl-3,5-heptane-dione (0.87 g, 5.54 mmol, 4.0 equiv.) and powdered potassium carbonate (1.15 g, 8.31 mmol, 6.0 equiv.) was heated at 40° C. for 2 h. 1 H-NMR analysis indicated the reaction was complete and the mixture was cooled to room temperature. Water (10 mL) was added and the resulting solid was filtered and washed with water (3 mL) and methanol (3 mL). The crude solid was purified on an Interchim automated system (80 g, silica gel cartridge) eluting with a 0-80% gradient of dichloromethane in heptane. The purest product fractions were concentrated under reduced pressure. The residue was triturated with a mixture of dichloromethane (2 mL) and methanol (10 mL) at 50 °C to give the desired product (~2.9 g, 98.9% UPLC purity, 0.9% oxide content). The product was further purified by trituration with a mixture of dichloromethane (2 mL) and acetonitrile (10 mL) at 50 °C to give bis[(4-(4-(tert-butyl)naphthalen-2-yl)-1'-yl)-6-(3,3,3-trifluoropropyl)-7-methyl-thieno[3,2-d]pyrimidin-3-yl)]-(2,6-dimethyl-3,5-heptane-dionato-kO,O')-iridium(III) (2.5 g, 75% yield, 99.6% UPLC purity) as a red solid.

[0151] Device Example

[0152] All of the devices in the examples were fabricated under high vacuum (<10 -7The devices were fabricated by thermal evaporation at 375 K (1000 Å) at 1000 Å (3200 Å) Torr. The anode electrode was 1,200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (lithium 8-hydroxyquinoline) and 1,000 Å of Al. All devices were encapsulated immediately after fabrication in a nitrogen glove box (<1 ppm H2O and O2) with a glass lid sealed with epoxy resin, and a moisture getter was placed inside the package. The organic stack for the device example consisted of, from the ITO surface, 100 Å of LG101 (purchased from LG Chem) as the hole injection layer (HIL); 400 Å of HTM as the hole transport layer (HTL); 50 Å of EBM as the electron blocking layer (EBL); 400 Å of emissive layer (EML) containing RH as red host and 3% emitter; and 350 Å of Liq (8-hydroxyquinoline lithium) doped with 35% ETM as the electron transport layer (ETL). Table 1 shows the thicknesses and materials of the device layers. [Table 1]

[0153] The chemical structures of the device materials are shown below. [ka]

[0154] Upon fabrication, the devices were tested for EL and JVL. For this purpose, the samples were subjected to a current density of 10 mA / cm using a two-channel Keysight B2902A SMU. 2 The radiance from 380 nm to 1080 nm (W / str / cm 2 ) and the total integrated photon count were determined. The device was then placed under a large area silicon photodiode for a JVL sweep. 2 The photodiode current is converted to photon count using the total photon count of the device at 0 to 200 mA / cm. 2The voltage is swept to a voltage equivalent to . The EQE of the device is calculated using the total total photon count. All results are summarized in Table 2. The voltage, EQE, and LE of the inventive examples (Devices 1 and 3) are shown as relative numbers normalized to the results of the comparative examples (Devices 2 and 4).

[0155] [Table 2] [Table 3] Tables 2 and 3 summarize the electroluminescent device performance and the sublimation temperature of the materials. The inventive devices (devices 1 and 3) showed similar voltage, EQE, and FWHM to the comparative devices (devices 2 and 4), but both inventive devices showed a lower λ max The blue shift of 2 nm and the improvement of LE were 7-9%. As a result, all of the inventive devices emitted more saturated red light and showed improved current efficiency. Furthermore, all of the inventive devices showed a 30°C lower sublimation temperature compared to the comparative example, which is important for improving the device fabrication process. [Explanation of symbols]

[0156] 100 Organic Light Emitting Device 110 Substrate 115 Anode 120 Hole injection layer 125 Hole transport layer 130 Electron Blocking Layer 135 Light-emitting layer 140 Hole Blocking Layer 145 Electron transport layer 150 Electron injection layer 155 Protective layer 160 Cathode 162 First conductive layer 164 Second conductive layer 170 Barrier Layer 200 Inverted OLED, device 210 Substrate 215 Cathode 220 Light-emitting layer 225 Hole transport layer 230 Anode

Claims

1. Ligand L of formula I Ａ 1. A material for use in an organic light emitting device (OLED), comprising: 【Chemistry 1】 Formula I (In the formula, A １ is fluorine, CH ２ F, C.H.F. ２ , or C.F. ３ and R １ is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R ２ is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R ２ does not contain fluorine; R ３ , R ４ , and R ５ are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R ６ is hydrogen, alkyl, or cycloalkyl; The ligand L Ａ is coordinated to a metal M; The metal M can be coordinated to other ligands; The ligand L Ａ can combine with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; Any two substituents can be bonded or fused to each other to form a ring, if chemically possible.

2. R １ , R ２ , R ３ , and R ４ 2. The material of claim 1, wherein each of said alkyl and cycloalkyl is alkyl or cycloalkyl.

3. A １ But, R ５ The material of claim 1, which is identical to

4. R ３ and R ４ are each alkyl, R ５ is alkyl or hydrogen; or R ３ , R ４ , and R ５ The material of claim 1 , wherein each of is fluorine.

5. 2. The material of claim 1, wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

6. The ligand L Ａ The material of claim 1, wherein is selected from the group consisting of: 【Chemistry 2】 (In the formula, R ７ is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, partially or fully fluorinated alkyl, and combinations thereof.

7. The ligand L Ａ But, L Ａｚ z is an integer from 1 to 46849770; L Ａ１ ~L Ａ４６８４９７７０ 2. The material of claim 1 , wherein the structure is defined as follows: 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 (In the formula, R Ｄ１ ~R Ｄ１９８ has the following structure: 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】

8. The ligand L Ａ The material of claim 1, wherein is selected from the group consisting of: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】

9. The material has the formula M(L Ａ ) ｘ (L Ｂ ) ｙ (L Ｃ ) ｚ wherein L Ｂ and L Ｃ are each a bidentate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; x+y+z is the oxidation state of the metal M; L Ｂ and L Ｃ 2. The material of claim 1, wherein each of said is independently selected from the group consisting of: 【Chemistry 16】 【Chemistry 17】 (In the formula, each Y １ ~Y １３ is independently selected from the group consisting of carbon and nitrogen; Y' is B R ｅ , N.R. ｅ , P.R. ｅ , O, S, Se, C=O, S=O, SO ２ , C.R. ｅ R ｆ , SiR ｅ R ｆ , and GeR ｅ R ｆ R ｅ and R ｆ may be fused or linked to form a ring; Each R ａ , R ｂ , R ｃ , and R ｄ independently represent monosubstitution to the maximum number of substitutions possible; Each R ａ , R ｂ , R ｃ , R ｄ , R ｅ , and R ｆ is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , R ｂ , R ｃ , and R ｄ Any two adjacent substituents of may be fused or linked to form a ring or to form a multidentate ligand.

10. L Ｂ The material of claim 9, wherein the may be selected from the group consisting of: 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 (wherein j is an integer from 1 to 400, and each L Ｂｊ In the formula (I), the substituent R Ｅ and G are defined as follows: 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 (In the formula, R １ ~R ２０ has the following structure: 【Chemistry 25】 【Chemistry 26】 (In the formula, G １ ~G ２０ has the following structure: 【Chemical 27】

11. The material is represented by the formula Ir(L Ａ ) (L Ｂｊ－ｋ ) ２ wherein k is an integer from 1 to 50, and the ligand L Ａ But, L Ａｚ z is an integer from 1 to 46849770; L Ａ１ ~L Ａ４６８４９７７０ 11. The material of claim 10, wherein the structure is defined as follows: 【Chemistry 28】 【Chemical Formula 29】 【Chemistry 30】 【Chemistry 31】 (In the formula, R Ｄ１ ~R Ｄ１９８ has the following structure: 【Chemistry 32】 【Chemical 33】 【Chemical Formula 34】 【Chemistry 35】

12. 2. The material of claim 1, wherein the material is selected from the group consisting of: 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】

13. Ligand L of formula I Ａ An organic layer comprising a compound comprising: 【Chemical Formula 39】 Formula I (In the formula, A １ is fluorine, CH ２ F, C.H.F. ２ , or C.F. ３ and R １ is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof; R ２ is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, with R ２ does not contain fluorine; R ３ , R ４ , and R ５ are each independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof; R ６ is hydrogen, alkyl, or cycloalkyl, and the ligand L Ａ is coordinated to a metal M; The metal M can be coordinated to other ligands; The ligand L Ａ can combine with other ligands to form tridentate, tetradentate, pentadentate, or hexadentate ligands; Any two substituents can be bonded or fused to each other to form a ring, if chemically possible.

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