Organic electroluminescent materials and devices

Abstract

A two-coordination metal complex compound is provided as a sensitizer for a fluorescent dye. Additionally, a formulation comprising such a two-coordination metal complex compound is provided. Additionally, an OLED and related consumer products utilizing such a two-coordination metal complex compound are provided. The OLED includes a light-emitting region comprising a first compound, which is a sensitizer having the structure of, and an acceptor.

Description

Technology Field

[0001] Cross-reference regarding related applications

[0002] This application claims priority to U.S. Provisional Application No. 62 / 980,533 filed on February 24, 2020, under 35 USC § 119(e), the whole of which is incorporated herein by reference.

[0003] field

[0004] The present disclosure generally relates to organometallic compounds and formulations, and various uses thereof, including as sensitizers in devices such as organic light-emitting diodes and related electronic devices. Background Technology

[0005] Optoelectronic devices using organic materials are becoming increasingly important for various reasons. Since many of the materials used to manufacture such devices are relatively inexpensive, organic optoelectronic devices have potential in terms of cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, can make them highly suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic phototransistors, organic photovoltaics, and organic photodetectors. In the case of OLEDs, organic materials can have performance advantages over conventional materials.

[0006] OLEDs use organic thin films that emit light when voltage is applied to the device. OLEDs are a technology that is becoming increasingly important for applications such as flat panel displays, lighting, and backlighting.

[0007] One application of phosphorescent emitting molecules is full-color displays. Industrial standards for such displays require pixels tuned to emit specific colors referred to as "saturated" colors. Specifically, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, light from a white backlight is filtered using absorption filters to produce red, green, and blue light. The same technique can also be applied to OLEDs. White OLEDs can be single-emissive layer (EML) devices or stacked structures. Color can be measured using CIE coordinates known in the art.

[0008] A combination of novel compounds that can be used in the emissive layer (EML) of an electroluminescent device is provided. Linear two-coordination metal complexes emitted via phosphorescence or TADF are paired with a fluorophore or TADF emitter to ensure sensitization of the fluorophore or TADF emitter via Foerster resonance energy transfer (FRET). Ultimately, the latter compounds are emitted in the near-UV, blue, green, orange, red, or near-IR portions of the spectrum. The two components of the EML can be covalently bonded through various different crosslinks. This direct bonding achieves two objectives: controlling the distance separating the two chromophores and predetermining their relative orientation (by optimizing FRET), thereby reducing harmful Dexter energy transfer.

[0009] In one embodiment, the present disclosure is an organic light-emitting device (OLED) comprising an anode; a cathode; and a light-emitting region disposed between the anode and the cathode; wherein the light-emitting region is a sensitizer as Formula I The present invention provides an OLED comprising a compound of; and an acceptor. In Formula I, MC is a metal carbene bond; M is selected from the group consisting of Cu, Ag and Au; and X 1is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se; n is 0, 1, or 2; represents a single or double bond; R, R', R A , R B , R C , R D and R E is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A , R B , R C , R D and R E Any two or more of them may be connected or fused to form a ring; the acceptor is selected from the group consisting of a fluorescence emitter, a delayed fluorescence emitter, and combinations thereof; provided that X 1 In the case of this CRR', the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max It emits light that has

[0010] In another aspect, the present disclosure provides a compound comprising the structure of Formula I below:

[0011] Formula I

[0012]

[0013] Here, MC is a metal carbene bond;

[0014] M is selected from the group consisting of Cu, Ag and Au; X 1is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se;

[0015] n is 0, 1, or 2, and; represents a single or double bond; R, R', R A , R B , R C , R D and R E is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A , R B , R C , R D and R E Any two or more of them can be connected or fused to form a ring.

[0016] In another aspect, the present disclosure provides a compound comprising the structure of the following formula VI:

[0017] Formula IV

[0018]

[0019] Here, M is selected from the group consisting of Cu, Ag, and Au; X 1' is selected from the group consisting of CRR', NR, O, S, SiRR', BR, and GeRR'; Y 1' is selected from the group consisting of C, N, B, O, S, Si, and Se; R, R', R A' , R B' , R C', R D' and R E' Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A' , R B' , R C' , R D' and R E' At least one of the comprises a chemical group capable of emitting light by fluorescence or delayed fluorescence and / or an organic linking crosslink comprising 1 to 24 carbon atoms between the organometallic moiety and the fluorescent moiety; n is 0, 1, or 2; represents a single or double bond; R, R', R A' , R B' , R C' , R D' and R E' Two or more of them can be connected or fused to form a ring.

[0020] In another aspect, the present disclosure provides a combination of the compounds of Formula I or Formula VI described herein.

[0021] In another aspect, the present disclosure provides an OLED having an organic layer comprising a compound of Formula I or Formula VI as described herein.

[0022] In another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of Formula I or Formula VI as described herein. Brief explanation of the drawing

[0023] Figure 1 illustrates an organic light-emitting device. Figure 2 illustrates an inverted organic light-emitting device that does not have a separate electron transport layer. FIG. 3 shows the electroluminescence spectra of a device using acceptors A, B, and C doped with sensitizer (1) and 0%, 1%, and 3%, respectively. Specific details for implementing the invention

[0024] A. terminology

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

[0026] As used herein, the term “organic” includes not only polymeric materials that can be used to fabricate organic optoelectronic devices, but also small molecule organic materials. “Small molecule” refers to any organic material that is not a polymer, and “small molecule” can actually be quite large. Small molecules may contain repeating units in some situations. For example, using a long-chain alkyl group as a substituent does not exclude the molecule from the “small molecule” type. Small molecules may also be incorporated into the polymer, for example, as pendant groups on the polymer main chain or as part of the main chain. Small molecules may also act as the core moiety of a dendrimer, which consists of a series of chemical shells formed on the core moiety. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and all dendrimers currently used in the OLED field are considered to be small molecules.

[0027] As used herein, "top part" means furthest from the substrate, and "bottom part" means closest to the substrate. If the first layer is described as being "placed on top of" the second layer, the first layer is placed far from the substrate. If the first layer is not specified as being "in contact" with the second layer, other layers may exist between the first layer and the second layer. For example, even if various organic layers exist between the cathode and the anode, the cathode may be described as being "placed on top of" the anode.

[0028] As used herein, "solution processability" means that it can be dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension, or can be deposited from a liquid medium.

[0029] If a ligand is considered to directly contribute to the photoactive properties of a luminescent material, the ligand may be referred to as "photoactive." If a ligand is considered not to contribute to the photoactive properties of the luminescent material, even though an auxiliary ligand may alter the properties of the photoactive ligand, the ligand may be referred to as "auxiliary."

[0030] As used herein, and as generally understood by those skilled in the art, where the first energy level is closer to the vacuum energy level, the first "highest occupied molecular orbital (HOMO)" or "lowest unoccupied molecular orbital (LUMO)" energy level is "greater" or "higher" than the second HOMO or LUMO energy level. Since the ionization potential (IP) is measured as negative energy with respect to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (less negative IP). Likewise, 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 closer to the top of the diagram than "lower" HOMO or LUMO energy levels.

[0031] As used herein, and as generally understood by those skilled in the art, if the absolute value of the first work function is greater, the first work function is "greater" or "higher" than the second work function. Since work functions are generally measured as negative numbers with respect to vacuum levels, this implies that the "higher" work function is more negative. In a typical energy level diagram with vacuum levels at the top, the "higher" work function is exemplified as being further down from the vacuum level. Therefore, the definition of HOMO and LUMO energy levels follows a different convention than that of work functions.

[0032] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0033] The term "acyl" refers to a substituted carbonyl radical (C(O)-R s It refers to ).

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

[0035] The term "ether" is -OR s It refers to radicals.

[0036] The terms "sulfanil" or "thio-ether" are used interchangeably, and -SR s It refers to radicals.

[0037] The term "sulfinyl" is -S(O)-R s It refers to radicals.

[0038] The term "sulfonyl" is -SO2-R s It refers to radicals.

[0039] The term "phosphino" is -P(R s Refers to )3 radicals, and each R s It may be the same or different.

[0040] The term "silyl" is -Si(R s Refers to )3 radicals, and each R s It may be the same or different.

[0041] The term "boril" is -B(R s )2 radical or its Lewis adduct -B(R s )Refers to the 3 radical, where R s It may be the same or different.

[0042] In each of the above, R s may be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferred R s is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0043] The term "alkyl" refers to and includes both straight-chain and branched-chain alkyl radicals. Preferred alkyl groups are those containing 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, 2,2-dimethylpropyl, etc. Additionally, the alkyl groups may be optionally substituted.

[0044] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl radicals. Preferred cycloalkyl groups are those containing 3 to 12 cyclic carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, cycloalkyl groups may be optionally substituted.

[0045] The terms "heteroalkyl" or "heterocycloalkyl" each refer to an alkyl or cycloalkyl radical having one or more carbon atoms substituted by a heteroatom. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Additionally, the heteroalkyl or heterocycloalkyl group may optionally be substituted.

[0046] The term "alkenyl" refers to and includes both straight-chain and branched-chain alkene radicals. An alkenyl group is essentially an alkyl group comprising one or more carbon-carbon double bonds in an alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group comprising one or more carbon-carbon double bonds within a cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl radical having one or more carbon atoms substituted by a heteroatom. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. A preferred alkenyl, cycloalkenyl, or heteroalkenyl group contains 2 to 15 carbon atoms. Additionally, an alkenyl, cycloalkenyl, or heteroalkenyl group may optionally be substituted.

[0047] The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne radicals. An alkynyl group is essentially an alkyl group comprising one or more carbon-carbon triple bonds in the alkyl chain. A preferred alkynyl group contains 2 to 15 carbon atoms. Additionally, the alkynyl group may be optionally substituted.

[0048] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.

[0049] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic radicals containing one or more heteroatoms. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Heteroaromatic cyclic radicals may also be used interchangeably with heteroaryls. Preferred heteronon-aromatic cyclic groups are those containing one or more heteroatoms and containing 3 to 7 ring atoms, including cyclic amines such as morpholino, piperidino, pyrrolidino, etc., and cyclic ethers / thio-ethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Additionally, heterocyclic groups may be optionally substituted.

[0050] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycyclic ring may have two or more rings in which two carbons are common to two adjacent rings (these rings are "fused"), wherein one or more of the rings are aromatic hydrocarbyl groups, and, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. A preferred aryl group contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. An aryl group having 6, 10, or 12 carbons is particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl groups may be optionally substituted.

[0051] The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems comprising one or more heteroatoms. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many cases, O, S, or N is a preferred heteroatom. A heteromonocyclic aromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and said ring may have 1 to 6 heteroatoms. A heteropolycyclic ring system may have two or more rings in which two carbons are common to two adjacent rings (these rings are "fused"), wherein one or more of the rings are heteroaryls, and, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryls. The heteropolycyclic aromatic ring system may have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. The preferred heteroaryl group contains 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, dibenzoselenopene, furan, thiophene, benzofuran, benzothiophene, benzoselenopene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazol, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazolin, quinoxaline, naphthiridine, phthalazine, pteridine, xanthen, acridine, phenazine, Includes phenothiazine, phenoxazine, benzopuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenofenofyridine and selenofenodipyridine, preferably dibenzothiophen, dibenzofuran, dibenzoselenofen, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azabolin, 1,3-azabolin, 1,4-azabolin, borazine and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

[0052] Among the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenopene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and their respective aza-analogs are of particular interest.

[0053] 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 general substituents.

[0054] In many cases, the general substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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.

[0055] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

[0056] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

[0057] In other cases, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0058] The terms "substituted" and "substituted" refer to substituents other than H bonded to the relevant positions, such as carbon or nitrogen. For example, R 1 In the case where this represents a uniform substitution, one R 1 must be something other than H (i.e., substitution). Similarly, R 1 In the case where this represents a bisubstitution, R 1 Two of them must be something other than H. Similarly, R 1 If this represents zero substitution or non-substitution, R 1The available valence of the ring atom can be hydrogen, for example, the carbon atom of benzene and the nitrogen atom of pyrrole, or simply nothing for the ring atom with a fully charged valence, such as the nitrogen atom of pyridine. The maximum number of substitutions possible in a ring structure depends on the total number of available valences in the ring atom.

[0059] As used herein, “combinations thereof” indicates that one or more components of the applicable list are combined to form a known or chemically stable arrangement that a person skilled in the art can conceive from the applicable list. For example, alkyl and deuterium may be combined to form a partially or wholly deuteriden alkyl group; halogen and alkyl may be combined to form a halogenated alkyl substituent; and halogen, alkyl, and aryl may be combined to form a halogenated arylalkyl. In one case, the term substitution comprises a combination of two to four of the listed groups. In another case, the term substitution comprises a combination of two to three groups. In yet another case, the term substitution comprises a combination of two groups. A preferred combination of substituents is one containing up to 50 atoms that are not hydrogen or deuterium, or one containing up to 40 atoms that are not hydrogen or deuterium, or one containing up to 30 atoms that are not hydrogen or deuterium. In many cases, the preferred combination of substituents will include up to 20 atoms that are not hydrogen or deuterium.

[0060] In the fragments described herein, namely aza-dibenzofuran, aza-dibenzothiophene, etc., the notation "aza" signifies that one or more of the CH groups in each aromatic ring can be substituted with nitrogen atoms, for example, azatriphenylene is dibenzo[ f,h ]Quinoxaline and dibenzo[ f,h] Includes, but is not limited to, all quinoline. Those skilled in the art may readily consider other nitrogen analogs of the aforementioned aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0061] As used herein, “deuterium” refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057, the entire text of which is incorporated herein by reference, describe the preparation of deuterium-substituted organometallic complexes. Additionally, the literature [Ming Yan, et al ., Tetrahedron 2015, 71, 1425-30] and literature[Atzrodt et al ., Angew. Chem. Int. Ed. (Reviews) See [2007, 46, 7744-65], the full text of which is incorporated herein by reference, and which each describe efficient routes for the deuteration of methylene hydrogens in benzylamine and the substitution of aromatic ring hydrogens with deuteration.

[0062] Where a molecular segment is described as a substituent or, if not, as attached to another moiety, it should be understood that its name may be described as the segment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or as the whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, different notations of such substituents or attached segments are considered equivalent.

[0063] In some cases, pairs of adjacent substituents may be arbitrarily combined (linked) or fused to form a ring. A preferred ring is a pentagonal, hexagonal, or heptagonal carbocyclic or heterocyclic ring, including cases where part of the ring formed by the pair of substituents is saturated and cases where part of the ring formed by the pair of substituents is unsaturated. As used herein, “adjacent” means that two related substituents may exist on two adjacent rings having the two closest substituable positions, e.g., the 2, 2’ position of biphenyl or the 1, 8 position of naphthalene, or on the same ring adjacent to each other, as long as a stable fused ring system can be formed.

[0064] B. Compounds of the present disclosure

[0065] A compound that can be useful as a sensitizer in an OLED is disclosed. The compound has the structure of Formula I below:

[0066]

[0067] Here, MC is a metal carbene bond;

[0068] M is selected from the group consisting of Cu, Ag and Au; X 1 is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se;

[0069] n is 0, 1, or 2, and; represents a single or double bond; R, R', R A , R B , R C , R D and R Eis independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A , R B , R C , R D and R E Any two or more of them can be connected or fused to form a ring.

[0070] In the present disclosure, silver, Y 1 Represents a single or double bond depending on the identity of and the value of n. For example, Y 1 If this is N or B and n is 1, or Y 1 If this is O, S, or Se and n is 0, represents a single bond. Y 1 If this is C or Si and n is 1, It represents a double bond.

[0071] The present disclosure also provides compounds comprising one or more structures of Formula I that are connected or fused together. These structures may be connected via direct bonding or linking groups, or fused via a carbocycle or heterocycle. These compounds have structures selected from the group consisting of the following:

[0072]

[0073]

[0074] Here, each M and X in the given equation 1 , Y 1 , R A , R B , R C , RD , R E can be the same or different, and in Equations II and IV, n is independently 0, 1, or 2, respectively.

[0075] In some embodiments, R, R', R A , R B , R C , R D and R E Each is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, boryl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

[0076] In some embodiments, Y 1 is N. In one embodiment, Y 1 is O and n is 0.

[0077] In some embodiments, R D and R E Each is a hexavalent aromatic ring and can be substituted. In some embodiments, R D and R E is Y 1 It is connected together to form a five-membered ring.

[0078] In some embodiments, X 1 is NR. In some embodiments, X 1 is CR.

[0079] In some embodiments, R A and R B They are connected to each other to form a 5- or 6-membered ring.

[0080] In some embodiments, R C is a 6-membered aromatic ring and can be substituted.

[0081] In some embodiments, M is Au. In some embodiments, M is Cu or Ag.

[0082] In some embodiments, a part of Formula I ...includes a structure selected from a group consisting of the following:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Here, the dashed line(s) of each structure represent a direct connection to M; X is independently C or N, respectively; and R G , R H , R I , R J , R K , R L , R P , R Q , R R , R Y and R Z Each is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, boryl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; R F -R M , R P , R Q , R S , R T , R Y and R Z Each independently represents no substitution, identical substitution, or the maximum number of permutations allowed.

[0092] In some embodiments, a part of Formula I is selected from a group consisting of:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] Here, A and B are each independently monocyclic or multicyclic ring systems comprising one or more fused pentagonal or hexagonal carbocyclic or heterocyclic rings; X is each independently selected from the group consisting of C and N; Y is each independently selected from the group consisting of CRR', SiRR', NR, BR, O, S, Se, and PR; R and R' are each independently representing unsubstituted, monosubstituted, or the maximum number of substitutions allowed; R and R' are each independently hydrogen or substituents selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

[0099] In some embodiments, the compound of Formula I is selected from the group consisting of the compounds of the following compound list 1:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] In one embodiment, the present disclosure provides a compound comprising the first structure of the following formula VI:

[0109]

[0110] Here, M is selected from the group consisting of Cu, Ag, and Au; X 1' is selected from the group consisting of CRR', NR, O, S, SiRR', BR, and GeRR'; Y 1' is selected from the group consisting of C, N, B, O, S, Si, and Se; R, R', R A' , R B' , R C' , R D' and R E' are each independently hydrogen or a general substituent; R, R', R A' , R B' , R C' , R D' and R E' At least one of the following comprises a chemical group capable of emitting light by fluorescence or delayed fluorescence and / or an organic linkage bridge comprising 1 to 24 carbon atoms between an organometallic moiety and a fluorescent moiety; the organometallic moiety is a moiety comprising a metal and two ligands directly connected thereto; the fluorescent moiety represents a luminescent dye that is emitted directly from the lowest excited singlet state S1 via fluorescence or directly from S1 along a thermal group from T1 via thermal activation delayed fluorescence, TADF, where n is 0, 1, or 2; represents a single or double bond; R, R', R A' , R B' , R C' , R D' and R E' Two or more of them can be connected or fused to form a ring.

[0111] In one embodiment, one or more structures having Formula VI may be connected or fused to each other. These structures may be connected via direct bonding or linking groups, or fused via a carbocycle or heterocycle. These compounds may have structures selected from the group consisting of the following:

[0112]

[0113]

[0114] Here, each M and X in the given equation 1' , Y 1' , R A' , R B' , R C' , R D' , R E' It may be the same or different,

[0115] In Equations VII and IX, n is independently 0, 1, or 2, respectively.

[0116] In one embodiment, R, R', R A' , R B' , R C' , R D' and R E' Each is independently a hydrogen or a general substituent or a preferred general substituent.

[0117] In one embodiment, R, R', R A' , R B' , R C' , R D' and R E' At least one of them includes a group selected from the group consisting of:

[0118]

[0119]

[0120]

[0121] Here, rings A to I are each independently monocyclic or multicyclic ring systems comprising one or more fused pentagonal or hexacyclic carbocyclic or heterocyclic rings; each R, M, X, and Y may be the same or different; and Z is each independently selected from the group consisting of B, CR, SiR, and N.

[0122] In one embodiment, R, R', R A' , R B' , R C' , R D' and R E' At least one of them also includes a bridging moiety selected from the group consisting of:

[0123]

[0124] Here, X" is independently C or N; each Y" is the same or different and is selected from the group consisting of O, S, Se, BR, NR, CRR' and SiRR'; each R" is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; each X and R may be the same or different.

[0125] In one embodiment, the compound is selected from the group consisting of the following:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] C. OLED and device of the present disclosure

[0140] In one embodiment, the present disclosure also provides an OLED device comprising a first organic layer containing a compound disclosed in the compound section of the present disclosure.

[0141] In one embodiment, the present disclosure is an organic light-emitting device (OLED) comprising an anode; a cathode; and a light-emitting region disposed between the anode and the cathode; wherein the light-emitting region is a sensitizer as Formula I The present invention provides an OLED comprising a first compound of and an acceptor. In Formula I, MC is a metal carbene bond; M is selected from the group consisting of Cu, Ag and Au; and X 1 is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se; n is 0, 1, or 2; represents a single or double bond; R, R', R A , R B , R C , R D and R Eis independently hydrogen or a general substituent disclosed above; R, R', R A , R B , R C , R D and R E Any two or more of them may be connected or fused to form a ring. The acceptor may be selected from the group consisting of fluorescence emitters, delayed fluorescence emitters, and combinations thereof. In the case of this OLED, X 1 When this is CRR', the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max It emits light that has

[0142] In some embodiments, the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max It emits light having . In some embodiments, the acceptor has a peak wavelength λ of 500 nm or less at room temperature. max It emits light having . In some embodiments, the acceptor has a peak wavelength λ of 480 nm or less at room temperature. max It emits light that has

[0143] In some embodiments of the OLED, the first compound may comprise one or more structures having Formula I that are connected or fused with one another. Such fused structures may be structures of Formulas I through V disclosed herein.

[0144] In one embodiment of the OLED, the light-emitting region comprises a first compound of the disclosed formula VI as a sensitizer. In some embodiments, the first compound may comprise one or more structures having formula VI that are connected or fused together. Such fused structures may be structures of formulas VI through X disclosed herein.

[0145] In some embodiments, the light-emitting region comprises one or more organic layers, and the sensitizer compound and the acceptor may be in the same layer or in two separate layers. The organic layer containing the acceptor becomes the light-emitting layer in the OLED. In some embodiments, the sensitizer and the acceptor are provided in the same layer, i.e., the light-emitting layer, and the sensitizer is doped into the light-emitting layer at a concentration ranging from 1 wt% to 25 wt%. In some embodiments, the acceptor is doped into the light-emitting layer at a concentration ranging from 0.1% to 5%. In some embodiments, the sensitizer compound is in the first organic layer of the light-emitting region and the acceptor compound is in the second organic layer of the light-emitting region. In an embodiment where the sensitizer and the acceptor are provided in two separate layers in the light-emitting region, the sensitizer may be doped into the first organic layer at a concentration ranging from 1 wt% to 25 wt%, and the acceptor may be doped into the second organic layer at a concentration ranging from 0.1% to 5%.

[0146] In one embodiment of the OLED, the acceptor is selected from the group consisting of:

[0147]

[0148]

[0149]

[0150] Here, rings A to I are each independently monocyclic or multicyclic ring systems comprising one or more fused pentagonal or hexacyclic carbocyclic or heterocyclic rings; each of R, M, X, and Y may be the same or different; and Z is each independently selected from the group consisting of B, CR, SiR, and N.

[0151] In one embodiment, the acceptor is selected from the group consisting of:

[0152]

[0153]

[0154]

[0155] In one embodiment, the light-emitting layer including the acceptor may further include a host.

[0156] In one embodiment, the present disclosure provides a consumer product comprising the OLED disclosed herein.

[0157] In one embodiment, the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and / or signal light, 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 information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

[0158] In some embodiments, the compound disclosed herein may be used as a host in an organic layer of a light-emitting region, and the organic layer is a light-emitting layer comprising a phosphorescent emitter.

[0159] In some embodiments, the compound may act as a component of an exciplex that is a fluorescent emitter, a delayed fluorescent emitter, or a fluorescent emitter or a delayed fluorescent emitter.

[0160] In some embodiments, the compound can act as a fluorescent emitter.

[0161] In some embodiments, the first organic layer may further include a phosphorescent sensitizer, and the compound is a fluorescent acceptor.

[0162] In some embodiments, the OLED may include a second light-emitting region disposed between an anode and a cathode, wherein the second light-emitting region includes a phosphorescent sensitizer, and the compound disclosed herein is provided to the second light-emitting region as a fluorescent acceptor.

[0163] In some embodiments, the phosphorescent sensitizer or phosphorescent emitter may be at least one ligand selected from the group consisting of the following, or a transition metal complex having a portion of the ligand when the ligand has more than two sites:

[0164]

[0165]

[0166] Here, T is B, Al, Ga, In and Y 1 to Y 13 Each is independently selected from the group consisting of carbon and nitrogen; Y' is BR e , NR e , PR e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f and GeR e R f Selected from a group consisting of; R e and R f can fuse or connect to form a ring; R a , R b , R c and R d ’ and ’ each independently represent no substitution, uniform substitution, or substitutions of less than or equal to the maximum allowed number for their associated loops; R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R fis each independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; R a1 , R b1 , R c1 , R d1 , R a , R b , R c and R d Two adjacent substituents of can fuse or connect to form a ring or a polydentate ligand.

[0167] In some embodiments, the organic layer may be a light-emitting layer, and the compound described herein may be a light-emitting dopant or a non-light-emitting dopant.

[0168] In some embodiments, the organic layer may further comprise a host, the host comprises a triphenylene-containing benzofused thiophene or a benzofused furan, and any substituent in the host is independently 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, and C n H 2n - A non-fusion substituent selected from the group consisting of -Ar1, or the host has no substituent, where n is 1 to 10; Ar1 ​​and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0169] In some embodiments, the organic layer may further comprise a host, and the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenopene, 5,9-dioxa-13b-boranaphthor[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenopene, and aza-(5,9-dioxa-13b-boranaphthor[3,2,1-de]anthracene).

[0170] In some embodiments, the host may be selected from the group consisting of the following compounds and combinations thereof:

[0171]

[0172]

[0173]

[0174] , ,

[0175] In some embodiments, the organic layer may further include a host, and the host includes a metal complex.

[0176] In some embodiments, the compound described herein may be a sensitizer; the device may further comprise an acceptor, and the acceptor may be selected from the group consisting of a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0177] In another aspect, the OLED of the present disclosure may also include a light-emitting region containing a compound disclosed in the compound section of the present disclosure.

[0178] In some embodiments, the light-emitting region is a sensitizer. It may include a first compound and an acceptor. In Formula I, MC is a metal carbene bond;

[0179] M is selected from the group consisting of Cu, Ag and Au; X 1 is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se;

[0180] n is 0, 1, or 2, and; represents a single or double bond; R, R', R A , R B , R C , R D and R E is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A , R B , R C , R D and R E Any two or more of them may be connected or fused to form a ring;

[0181] The acceptor is selected from the group consisting of a fluorescence emitter, a delayed fluorescence emitter, and combinations thereof. The acceptor can be selected from the group consisting of a fluorescence emitter, a delayed fluorescence emitter, and combinations thereof. In the case of this OLED, X 1 When this is CRR', the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max It emits light that has

[0182] In some embodiments, the light-emitting region is a sensitizer. It may include a first compound and an acceptor. In Formula VI, M is selected from the group consisting of Cu, Ag, and Au; and X 1' is selected from the group consisting of CRR', NR, O, S, SiRR', BR, and GeRR'; Y 1' is selected from the group consisting of C, N, B, O, S, Si, and Se; R, R', R A' , R B' , R C' , R D' and R E' Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A' , R B' , R C' , R D' and R E' At least one of the comprises a chemical group capable of emitting light by fluorescence or delayed fluorescence and / or an organic linking crosslink comprising 1 to 24 carbon atoms between the organometallic moiety and the fluorescent moiety; n is 0, 1, or 2; represents a single bond or a double bond;

[0183] One or more additional structures having Equation VI may be connected to or fused with the first structure; R, R', R A' , R B' , R C' , R D' and R E' Two or more of them may be connected or fused to form a ring. The acceptor may be selected from the group consisting of a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0184] In some embodiments, at least one of the new layers disposed on the anode, cathode, or organic light-emitting layer functions as an enhancement layer. The enhancement layer comprises a plasmonic material that exhibits surface plasmon resonance, which is non-radiatively coupled to the emitter material and transfers excited state energy from the emitter material to surface plasmon polaritons in a non-radiative mode. The enhancement layer is provided within a critical distance from the organic light-emitting layer, where the emitter material has a total non-radiative decay rate constant and a total radioactive decay rate constant due to the presence of the enhancement layer, and the critical distance is where the total non-radiative decay rate constant is equal to the total radioactive decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer opposite the organic light-emitting layer. In some embodiments, the outcoupling layer is disposed on the side opposite the light-emitting layer from the enhancement layer but still outcouples energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, energy is scattered from the surface plasmon mode to other modes of the device, such as (but not limited to) organic waveguide modes, substrate modes, or other waveguide modes. If energy is scattered to the non-free space modes of the OLED, other outcoupling schemes may be incorporated to extract the energy into free space. In some embodiments, one or more interlayers may be disposed between the reinforcement layer and the outcoupling layer. Examples of the interlayer(s) may be dielectric materials including organic, inorganic, perovskite, and oxide materials, and may include stacks and / or mixtures of these materials.

[0185] The reinforcing layer alters the effective properties of the medium in which the emitter material is present, resulting in any or all of the following: a decrease in luminescence rate, a change in the shape of the luminescence line, a change in luminescence intensity with respect to angle, a change in the stability of the emitter material, a change in the efficiency of the OLED, and a reduced efficiency roll-off of the OLED device. By placing the reinforcing layer on the cathode side, the anode side, or both sides, an OLED device utilizing any of the aforementioned effects is created. In addition to the specific functional layer described in the various OLED examples mentioned herein and illustrated in the drawings, the OLED according to the present disclosure may include any other functional layer commonly provided in OLEDs.

[0186] The reinforcing layer may be composed of a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmonic material is a material in which the real part of the dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In these embodiments, the metal may comprise 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 stacks of these materials. Generally, a metamaterial is a medium composed of different materials in which the entire medium acts differently from the sum of its parts. In particular, the applicant defines an optically active metamaterial as a material having both a negative permittivity and a negative transmittance. Meanwhile, a hyperbolic metamaterial is an anisotropic medium in which the permittivity or transmittance has different signs for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are strictly distinguished from many other photonic structures, such as Distributed Bragg Reflectors ("DBRs"), in that the medium must appear uniform in the direction of propagation over the wavelength scale of light. Using terms understood by those skilled in the art: the dielectric constant of a metamaterial in the direction of propagation can be described by an effective medium approximation. Plasmon materials and metamaterials provide methods to control the propagation of light that can enhance OLED performance in various ways.

[0187] In some embodiments, the reinforcing layer is provided as a planar layer. In other embodiments, the reinforcing layer has wavelength-sized features arranged periodically, semi-periodicly, or randomly, or subwavelength-sized features arranged periodically, semi-periodicly, or randomly. In some embodiments, the wavelength-sized features and subwavelength-sized features have sharp edges.

[0188] In some embodiments, the outcoupling layer has features of wavelength sizes arranged periodically, semi-periodicly, or randomly, or features of subwavelength sizes arranged periodically, semi-periodicly, or randomly. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, outcoupling is adjustable by at least one of changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material or additional layer disposed on the plurality of nanoparticles, changing the thickness of the reinforcing layer, and / or changing the material of the reinforcing layer. The plurality of nanoparticles of the device may be formed as a metal, a dielectric material, a semiconductor material, an alloy of a metal, a mixture of dielectric materials, a stack or layer of one or more materials, and / or a core of one type of material, which is formed as at least one of a core coated with a shell of a different type of material. In some embodiments, the outcoupling layer is composed of at least one nanoparticle selected from the group consisting of metals Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. Multiple nanoparticles may have additional layers disposed thereon. In some embodiments, the polarization of the emission can be adjusted using the outcoupling layer. By varying the dimensions 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 acts as an electrode of the device.

[0189] In another aspect, the present disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound disclosed in the compound section of the present disclosure.

[0190] In one embodiment, the consumer product is an OLED comprising an anode; a cathode; and a light-emitting region disposed between the anode and the cathode; wherein the light-emitting region is a sensitizer It comprises a first compound of and an OLDE comprising an acceptor. In Formula I, MC is a metal carbene bond; M is selected from the group consisting of Cu, Ag and Au; and X 1 is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se; n is 0, 1, or 2; represents a single or double bond; R, R', R A , R B , R C , R D and R E is independently hydrogen or a general substituent disclosed above; R, R', R A , R B , R C , R D and R E Any two or more of them may be connected or fused to form a ring. The acceptor may be selected from the group consisting of fluorescence emitters, delayed fluorescence emitters, and combinations thereof. In the case of this OLED, X 1 When this is CRR', the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max It emits light that has

[0191] In some embodiments, the consumer product is an OLED having an anode; a cathode; and a light-emitting region disposed between the anode and the cathode, wherein the light-emitting region is a sensitizer It comprises an OLDE comprising a first compound and an acceptor. In Formula VI, M is selected from the group consisting of Cu, Ag, and Au; and X 1' is selected from the group consisting of CRR', NR, O, S, SiRR', BR, and GeRR'; Y 1' is selected from the group consisting of C, N, B, O, S, Si, and Se; R, R', R A' , R B' , R C' , R D' and R E' Each is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A' , R B' , R C' , R D' and R E' At least one of the comprises a chemical group capable of emitting light by fluorescence or delayed fluorescence and / or an organic linking crosslink comprising 1 to 24 carbon atoms between the organometallic moiety and the fluorescent moiety; n is 0, 1, or 2; represents a single or double bond; R, R', R A' , R B' , R C' , R D' and R E'Two or more of them may be connected or fused to form a ring. The acceptor may be selected from the group consisting of fluorescent emitters, delayed fluorescent emitters, and combinations thereof for this OLED.

[0192] In some embodiments, the consumer product may be one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and / or signal light, 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 information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

[0193] Generally, an OLED comprises one or more organic layers disposed between an anode and a cathode and electrically connected to them. When current is applied, the anode injects holes into the organic layer(s), and the cathode injects electrons. The injected holes and electrons move toward oppositely charged electrodes, respectively. When electrons and holes are localized on the same molecule, "excitons" are generated, which are localized electron-hole pairs with excited energy states. Light is emitted when excitons relax through a photo-emission mechanism. In some cases, excitons may be localized on excimers or exciplexes. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

[0194] Various OLED materials and compositions are described in U.S. Patents No. 5,844,363, 6,303,238 and 5,707,745, the full text of which is incorporated herein by reference.

[0195] Early OLEDs used light-emitting molecules that emit light ("fluorescence") from a singlet state, such as disclosed in, for example, U.S. Patent No. 4,769,292, the entirety of which is incorporated by reference. Fluorescence emission generally occurs in a time frame of less than 10 nanoseconds.

[0196] More recently, OLEDs having a light-emitting material that emits light ("phosphorescence") from a triplet state have been presented. The literature [Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, vol. 395, 151-154, 1998; ("Baldo-I")] and the literature [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")] are incorporated by reference in their entirety. Phosphorescence is described in more detail in columns 5-6 of U.S. Patent No. 7,279,704, incorporated by reference.

[0197] FIG. 1 illustrates an organic light-emitting device (100). The drawing is not necessarily drawn to scale. The device (100) may include a substrate (110), an anode (115), a hole injection layer (120), a hole transport layer (125), an electron blocking layer (130), 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 compound cathode having a first conductive layer (162) and a second conductive layer (164). The device (100) may be fabricated by depositing layers in the order described. The properties and functions of the exemplary materials, as well as these various layers, are described more specifically in columns 6-10 of U.S. Patent No. 7,279,704, which is incorporated by reference.

[0198] Further examples for each of these layers are also available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, the full text of which is incorporated by reference. An example of a p-doped hole transport layer is one in which m-MTDATA is doped with F4-TCNQ in a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, the full text of which is incorporated by reference. Examples of luminescent and host materials are disclosed in U.S. Patent No. 6,303,238 (Thompson et al.), the full text of which is incorporated 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 No. 2003 / 0230980, the full text of which is incorporated by reference. Examples of cathodes are disclosed in U.S. Patents No. 5,703,436 and No. 5,707,745, the full text of which is incorporated by reference, including compound cathodes having thin layers of metals such as Mg:Ag with stacked transparent, electrically conductive sputter-deposited ITO layers. The theory and applications 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, the full text of which is incorporated by reference. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, the full text of which is incorporated by reference. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, the full text of which is incorporated by reference.

[0199] FIG. 2 illustrates an inverted structure OLED (200). The device comprises a substrate (210), a cathode (215), a light-emitting layer (220), a hole transport layer (225), and an anode (230). The device (200) can be fabricated by depositing layers in the order described. Since the most common OLED configuration has the cathode positioned above the anode and the device (200) has the cathode (215) positioned below the anode (230), the device (200) may be referred to as an "inverted structure" OLED. A material similar to that described for the device (100) may be used for the corresponding layers of the device (200). FIG. 2 provides an example of how some layers may be omitted from the structure of the device (100).

[0200] The simple stacked structure illustrated in FIGS. 1 and 2 is provided as a non-limiting example, and it is understood that embodiments of the present disclosure may be used in relation to various other structures. The specific materials and structures described are for illustrative purposes only, and other materials and structures may also be used. Functional OLEDs may be achieved by combining the various layers described in different 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. Although many examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of a host and a dopant, or more generally a mixture, may be used. Additionally, layers may have various underlying layers. The names given herein for the various layers are not intended to be strictly limited. For example, in the device (200), the hole transport layer (225) transports holes and injects holes into the light-emitting layer (220), and may be described as a hole transport layer or a hole injection layer. In one embodiment, the OLED may be described as having an "organic layer" disposed between the cathode and the anode. This organic layer may comprise a single layer or may further comprise a plurality of layers of different organic materials, for example, as described in relation to FIGS. 1 and 2.

[0201] OLEDs (PLEDs) comprising structures and materials not specifically described, such as polymer materials as disclosed in U.S. Patent No. 5,247,190 (Friend et al.), may also be used, the full text of which is incorporated herein by reference. As an additional 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 (Forrest et al.), the full text of which is incorporated herein by reference. OLED structures may deviate from the simple stacked structures shown in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as a mesa structure as described in U.S. Patent No. 6,091,195 (Forrest et al.) and / or a pit structure as described in U.S. Patent No. 5,834,893 (Bulovic et al.), the full text of which is incorporated herein by reference.

[0202] Unless otherwise specified, any layer of any embodiment may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation as described in U.S. Patents No. 6,013,982 and 6,087,196 (the full text of which is incorporated by reference), ink-jet, organic vapor deposition (OVPD) as described in U.S. Patent No. 6,337,102 (Forrest et al.) (the full text of which is incorporated by reference), and organic vapor jet printing (OVJP) as described in U.S. Patent No. 7,431,968 (the full text of which is incorporated by reference). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in nitrogen or an inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred pattern formation methods include pattern formation associated with some deposition methods such as deposition through a mask, cold welding as described in U.S. Patents No. 6,294,398 and 6,468,819 (the full text of which is incorporated by reference), ink-jet, and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to be compatible with a specific deposition method. For example, branched or unbranched substituents, such as alkyl and aryl groups containing three or more carbons, may be used on small molecules to improve their solution processing capabilities. Substituents having 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Since asymmetric materials may have a lower tendency for recrystallization, materials with asymmetric structures may have better solution processing capabilities than materials with symmetric structures. Dendrimer substituents may be used to improve the solution processing capabilities of small molecules.

[0203] A device fabricated according to an embodiment of the present disclosure may optionally further include a barrier layer. One purpose of the barrier layer is to protect the electrode and organic layer from damage caused by exposure to harmful species in an environment containing moisture, vapor and / or gas. The barrier layer may be deposited on, below, or to the side of the electrode or substrate, on any other part of the device including the edge. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may comprise a composition having multiple phases as well as a composition having a single phase. Any suitable material or combination of materials may be used in the barrier layer. The barrier layer may comprise an inorganic or organic compound or both. A preferred barrier layer comprises a mixture of polymeric and non-polymeric materials as described in U.S. Patent No. 7,968,146, PCT Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, the full text of which is incorporated herein by reference. To be considered a "mixture," the aforementioned polymer and non-polymer materials comprising a barrier layer must be deposited under the same reaction conditions and / or at the same time. The weight ratio of the polymer to the non-polymer material may be in the range of 95:5 to 5:95. The polymer and non-polymer materials may be produced from the same precursor material. In one example, the mixture of the polymer and non-polymer materials essentially consists of polymeric silicon and inorganic silicon.

[0204] A device manufactured according to an embodiment of the present disclosure may be contained within a wide variety of electronic component modules (or units) that may be included in various electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, light-emitting devices, such as individual light source devices or lighting panels, which may be used by end consumer product manufacturers. Such electronic component modules may optionally include driving electronic devices and / or power source(s). A device manufactured according to an embodiment of the present disclosure may be contained within a wide variety of consumer products that include one or more electronic component modules (or units). A consumer product comprising an OLED that includes the compound of the present disclosure in an organic layer within the OLED is disclosed. Such consumer products may include any type of product comprising one or more light source(s) and / or one or more of any type of image display. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lights, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays tiled together, theater or stadium screens, phototherapy devices, and signage. Devices manufactured according to the present disclosure may be controlled using various control mechanisms, including passive matrices and active matrices.Many devices are intended to be used in a temperature range that provides comfort to people, such as 18°C ​​to 30°C, more preferably at room temperature (20°C to 25°C), but can also be used at temperatures outside the above temperature range, such as -40°C to +80°C.

[0205] Further details regarding OLEDs and the foregoing definitions can be found in U.S. Patent No. 7,279,704, the full text of which is incorporated herein by reference.

[0206] 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.

[0207] In some embodiments, the OLED has one or more properties selected from the group consisting of flexible, rollable, foldable, stretchable, and curved properties. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer containing carbon nanotubes.

[0208] In some embodiments, the OLED further comprises a layer containing a delay fluorescence emitter. In some embodiments, the OLED comprises an array of RGB pixels, or an array of white plus color filter pixels. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel with a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel with a diagonal of 10 inches or more or an area of ​​50 square inches or more. In some embodiments, the OLED is a lighting panel.

[0209] In some embodiments, the compound may be a luminescent dopant. In some embodiments, the compound may produce luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, for example, U.S. Patent Application No. 15 / 700,352, the full text of which is incorporated herein by reference), triplet-triplet extinction, or a combination of these processes. In some embodiments, the luminescent dopant may be a racemic mixture or may be rich in one enantiomer. In some embodiments, the compound may be homoligandic (each ligand is identical). In some embodiments, the compound may be heteroligandic (at least one ligand is different from the others). Where more than one ligand is coordinated to the metal, the ligands may all be identical in some embodiments. In some other embodiments, at least one ligand is different from the remaining ligands. In some embodiments, all ligands may be different from each other. This also applies to embodiments in which a ligand coordinated to a metal may be connected to another ligand coordinated to the metal to form a triad, tetraad, quintad, or hexaadad. Thus, when the coordination ligands are connected together, all ligands may be the same in some embodiments, and at least one of the connected ligands may be different from the remaining ligand(s) in some other embodiments.

[0210] In some embodiments, the compound may be used as a phosphorescent sensitizer in an OLED, wherein one or more layers within the OLED contain acceptors in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound may be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the acceptor, and the acceptor releases energy or additionally 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, luminescence may occur from any or all of the sensitizer, the acceptor, and the final emitter.

[0211] According to another embodiment, a formulation comprising the compound described herein is also disclosed.

[0212] The OLED disclosed herein may be included in one or more of consumer products, electronic component modules, and lighting panels. The organic layer may be a light-emitting layer, and the compound may be a light-emitting dopant in some embodiments, while the compound may be a non-light-emitting dopant in other embodiments.

[0213] In another aspect of the present disclosure, a formulation comprising a novel compound disclosed herein is described. The formulation may comprise 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.

[0214] The present disclosure comprises any chemical structure comprising the novel compound of the present disclosure, or a monovalent or polyvalent variant thereof. That is, the compound of the present invention, or a monovalent or polyvalent variant thereof, may be part of a larger chemical structure. Such chemical structure may be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermacromolecules). As used herein, a “monovalent variant of the compound” exhibits the same moiety as the compound, except that one hydrogen is removed and replaced by a bond to the remainder of the chemical structure. As used herein, a “polyvalent variant of the compound” exhibits the same moiety as the compound, except that one or more hydrogens are removed and replaced by a bond or bonds to the remainder of the chemical structure. In the case of supramolecules, the compound of the present invention may also be incorporated into a supramolecular complex without covalent bonding.

[0215] D. Combination of the compounds of the present disclosure and other substances

[0216] The materials described herein as useful for a specific layer in an organic light-emitting device may be used in combination with a wide variety of other materials present in the device. For example, the light-emitting dopant disclosed herein may be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art may readily refer to the literature to identify other materials that may be useful in combination.

[0217] a) Conductive dopant:

[0218] The charge transport layer can be doped with a conductive dopant to substantially change its charge carrier density, which will consequently change its conductivity. Conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the semiconductor's Fermi level 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.

[0219] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing the materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.

[0220]

[0221] b) HIL / HTL :

[0222] The hole injection / transport materials intended for use in this disclosure are not specifically limited, and any compound commonly used as a hole injection / transport material may be used. Non-limiting examples of materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers comprising fluorohydrocarbons; polymers having conductive dopants; conductive polymers, e.g., PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; and metal oxide derivatives, e.g., MoO₂ x; p-type semiconductor organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes and crosslinkable compounds may be examples.

[0223] Non-limiting examples of aromatic amine derivatives used in HIL or HTL include the following structural formulas:

[0224]

[0225] Each Ar 1 or Ar 9is a group composed of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; Dibenzothiophen, Dibenzofuran, Dibenzoselenopene, Furan, Thiophene, Benzofuran, Benzothiophene, Benzoselenopene, Carbazole, Indolocarbazole, Pyridylindole, Pyrrolodipyridine, Pyrazol, Imidazole, Triazole, Oxazole, Thiazole, Oxadiazole, Oxatriazole, Dioxazole, Thiadiazole, Pyridine, Pyridazine, Pyrimidine, Pyrazine, Triazine, Oxazine, Oxathiazine, Oxadiazine, Indole, Benzimidazole, Indazole, Indoxazine, Benzoxazole, Benzisoxazole, Benzothiazole, Quinoline, Isoquinoline, Sinnoline, Quinazolin, Quinoxaline, Naphthiridine, Phthalasine, Pteridine, Xanthen, Acridine, Phenazine, Phenothiazine, A group consisting of aromatic heterocyclic compounds such as phenoxazine, benzopuropyridine, propipyridine, benzothiopyridine, thienodipyridine, benzoselenofenopyridine, and selenofenopyridine; and a group of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and selected from a group consisting of 2 to 10 cyclic structural units that are bonded through one or more 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 or directly bonded to each other. Each Ar may be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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.

[0226] In one mode, Ar 1 or Ar 9is independently selected from the group consisting of the following chemical formulas:

[0227]

[0228] Here, k is an integer from 1 to 20; X 101 To X 108 is C (including CH) or N; Z 101 eu NAr 1 , O or S and; Ar 1 It has the same mechanism as defined above.

[0229] Non-limiting examples of metal complexes used in HIL or HTL include the following chemical formulas:

[0230]

[0231] Here, Met is a metal and can have an atomic weight greater than 40; (Y 101 -Y 102 ) is a 2-position ligand, and Y 101 and Y 102 is independently selected from C, N, O, P, and S; L 101 is an auxiliary ligand; k' is an integer value of the maximum number of ligands that can be attached to the metal, ranging from 1 to the maximum number of ligands that can be attached to the metal; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0232] 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 has a minimum oxidation potential versus Fc in solution of less than about 0.6 V. + / Fc has a couple.

[0233] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such 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.,

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242] c) EBL:

[0243] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer within the device can lead to significantly higher efficiency and / or longer lifetime compared to a similar device without a blocking layer. Additionally, the blocking layer can be used to confine light emission to a desired area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or 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 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 functional group as one of the hosts described below.

[0244] d) Host:

[0245] The light-emitting layer of the organic EL device of the present disclosure preferably comprises at least a metal complex as a light-emitting material and may comprise a host material using a metal complex as a dopant material. Examples of host materials are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is greater than the triplet energy of the dopant. Any host material may be used with any dopant as long as the triplet criterion is satisfied.

[0246] An example of a metal complex used as a host preferably has the following chemical formula:

[0247]

[0248] Here, Met is a metal; (Y 103 -Y 104 ) is a 2-position 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 of the maximum number of ligands that can be attached to the metal, from 1 to; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0249] In one embodiment, the metal complex , where (ON) is a 2-bed ligand having a metal coordinated to atoms O and N.

[0250] In another embodiment, Met is selected from Ir and Pt. In an additional embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0251] In one embodiment, the host compound is a group consisting of aromatic hydrocarbon cyclic compounds, such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; Aromatic heterocyclic compounds, e.g., dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazol, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazolin, quinoxaline, naphthiridine, phthalazine, pteridine, xanthen, acridine, It contains at least one of the group consisting of phenazine, phenothiazine, phenoxazine, benzopuropyridine, purodipyridine, benzothienopyridine, thienodipyridine, benzoselenofenofyridine and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units that are of the same or different type selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and are bonded through one or more 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, or are directly bonded to each other. Each option within each group may be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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.

[0252] In one embodiment, the host compound contains one or more of the following groups in the molecule:

[0253]

[0254]

[0255] Here, R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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 if it is aryl or heteroaryl, it has a definition similar to that of Ar described above. k is an integer from 0 to 20 or from 1 to 20. X 101 To X 108 is independently selected from C (including CH) or N. Z 101 and Z 102 is independently NR 101 , is selected from O or S.

[0256] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803,

[0257]

[0258]

[0259]

[0260]

[0261]

[0262] e) additional Emitter:

[0263] One or more additional emitter dopants may be used in combination with the compounds of the present disclosure. Examples of additional emitter dopants are not particularly limited, and any compound that is typically used as an emitter material may be used. Examples of suitable emitter materials include, but are not limited to, compounds capable of producing luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet quenching, or a combination of these processes.

[0264] Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such 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, US2014103305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US7332232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586, US8871361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.,

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] f) HBL:

[0272] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the emissive layer. The presence of such a blocking layer within the device can lead to significantly higher efficiency and / or longer lifetime compared to similar devices without a blocking layer. Additionally, the blocking layer can be used to confine light emission to a desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than one or more of the hosts closest to the HBL interface.

[0273] In one embodiment, the compound used in the HBL contains the same molecule or functional group as the aforementioned host.

[0274] In another embodiment, the compound used in HBL contains one or more of the following groups in the molecule:

[0275]

[0276] Here, k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0277] g) ETL:

[0278] The electron transport layer (ETL) may comprise a material capable of transporting electrons. The electron transport layer may be native (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.

[0279] In one embodiment, the compound used for ETL contains one or more of the following groups in the molecule:

[0280]

[0281] Here, R 101 Ar is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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 if it is aryl or heteroaryl, it has a definition similar to that of Ar described above. 1 or Ar 3 has a definition similar to Ar described above. k is an integer from 1 to 20. X 101 To X 108 It is selected from C (including CH) or N.

[0282] In another embodiment, the metal complex used in the ETL includes, but is not limited to, the following chemical formula:

[0283]

[0284] Here, (ON) or (NN) is a 2-bed ligand having a metal coordinated to atoms O, N or N, N; L 101is another ligand; k' is an integer value ranging from 1 to the maximum number of ligands to which a metal can be attached.

[0285] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

[0286]

[0287]

[0288]

[0289] h) Charge Generation Layer (CGL):

[0290] In tandem or stacked OLEDs, the CGL plays an essential role in terms of performance and consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied from the CGL and the electrodes. Electrons and holes consumed in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Conventional CGL materials include n and p conductive dopants used in the transport layer.

[0291] In any of the aforementioned compounds used in each layer of the OLED device, hydrogen atoms may be partially or completely deuterinated. Thus, any specifically listed substituents, e.g., methyl, phenyl, pyridyl, etc., may be in their non-deuterinated, partially deuterinated, and fully deuterinated forms. Likewise, substituent types, e.g., non-deuterinated, alkyl, aryl, cycloalkyl, heteroaryl, etc., may also be in their non-deuterinated, partially deuterinated, and fully deuterinated forms.

[0292] It should be understood that the various embodiments described herein are merely illustrative and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the invention. Accordingly, as will be apparent to those skilled in the art, the claimed invention may include variations derived from the specific embodiments and preferred embodiments described herein. It should be understood that there is no intention to limit the various theories regarding why the invention is effective.

[0293] Experimental data

[0294] OLEDs were grown on a glass substrate pre-coated with an indium-tin-oxide (ITO) layer having a sheet resistance of 15-Ω / sq. Before any organic layer deposition or coating, the substrate was degreased with a solvent, then treated with an oxygen plasma at 50 W at 100 mTorr for 1.5 minutes, and treated with UV ozone for 5 minutes.

[0295] The device in Table 1 creates a high vacuum (< 10) by thermal evaporation -6 It was manufactured in Torr. The anode electrode was 750 Å indium tin oxide (ITO). Device Examples 1 to 4 had organic layers consisting of, sequentially from the ITO surface, 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 EML containing compound 3 doped with 50% compound 4, 12% sensitizer 1 and x% acceptor (x = 0%, 0.5%, 1%, 3%), a 300 Å layer of compound 6 doped with 35% compound 5 (ETL), a 10 Å layer of compound 6 (EIL), followed by a 1,000 Å layer of Al (cathode). All devices were encapsulated with glass lids sealed with epoxy resin in a nitrogen glove box (< 1 ppm H2O and O2) immediately after fabrication, and a moisture getter was incorporated into the package. The doping percentage is volume%.

[0296] OLED materials used

[0297]

[0298]

[0299] Table 1 OLED device data for a device using sensitizer 1 as a single emitter (Device Example 1), sensitizer 1 having acceptor A at a 1% doping concentration (Device Example 2), sensitizer 1 having acceptor B at a 1% doping concentration (Device Example 3), and sensitizer 1 having acceptor C at a 1% doping concentration (Device Example 4).

[0300] FIG. 3 shows the electroluminescence (EL) spectra of device examples 1, 2, 3 and 4.

[0301] In a device using sensitizer 1, when acceptors A, B, and C are doped to 1%, the EL spectrum, λ max and CIE y Energy transfer to the acceptor, as observed in the data, occurs, reflecting efficient energy transfer. Therefore, Sensitizer 1 is an effective sensitizer for three different fluorescent / TADF acceptors. This induces device emission from the acceptor, which is a blue-shifted λ compared to the unsensitized Device 1. max It features. In devices 2 and 4, CIE y It is reduced compared to the non-sensitized device. Therefore, sensitizing fluorescent / TADF acceptors using linear metal complexes is an effective method to obtain device emission at higher energies.

Claims

Claim 1 An organic light-emitting device (OLED) comprising an anode; a cathode; and a light-emitting region disposed between the anode and the cathode, wherein the light-emitting region is a first compound which is a sensitizer having the structure of Formula I below: Here, MC is a metal carbene bond; M is selected from the group consisting of Cu, Ag, and Au; and X 1 is selected from the group consisting of CR, CRR', NR, O, S, PR, SiRR', BR, and GeRR'; Y 1 is selected from the group consisting of C, N, B, O, S, Si, and Se; n is 0, 1, or 2; represents a single or double bond; R, R', R A , R B , R C , R D and R E is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A , R B , R C , R D and R E Any two or more of the above may be connected or fused to form a ring; and include an acceptor selected from the group consisting of a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof, wherein the sensitizer has a first singlet energy (S1) and a first triplet energy (T1); the acceptor has a first singlet energy (S1) and a first triplet energy (T1); the S1 of the sensitizer is higher than the S1 of the acceptor; the T1 of the sensitizer is higher than the T1 of the acceptor; accordingly, an excited state formed in the S1 or T1 of the sensitizer is transferred to the S1 of the acceptor via Foerster resonance energy transfer (FRET); provided that X 1 When this is CRR', the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max An organic light-emitting device (OLED) that emits light having Claim 2 In claim 1, the OLED having a structure selected from the group consisting of the first compound: Here, each M and X in the given equation 1 , Y 1 , R A , R B , R C , R D , R E can be the same or different, and in Equations II and IV, n is independently 0, 1, or 2, respectively. Claim 3 In paragraph 1, R, R', R A , R B , R C , R D and R E OLEDs, each independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, boryl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof. Claim 4 In paragraph 1, Y 1 It is an N-sized OLED. Claim 5 In paragraph 1, an OLED to which at least one of the following applies: (a) R D and R E are each six-membered aromatic rings and can be substituted; (b) R D and R E is Y 1 Connected together to form a five-membered ring; (c) R A and R B are connected to each other to form a 5- or 6-membered ring; (d) R C is a 6-membered aromatic ring and can be substituted. Claim 6 In paragraph 1, X 1 It is an OLED that is NR or CR. Claim 7 In paragraph 1, M is an OLED that is Au, Cu, or Ag. Claim 8 In claim 1, the acceptor has a peak wavelength λ of 520 nm or less at room temperature. max An OLED that emits light having Claim 9 In paragraph 1, the part in Formula I OLED comprising a structure selected from a group consisting of: Here, the dashed line(s) of each structure represent a direct connection to M; X is independently C or N, respectively; and R G , R H , R I , R J , R K , R L , R P , R Q , R R , R Y and R Z Each is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, boryl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; R F -R M , R P , R Q , R S , R T , R Y and R Z Each independently represents no substitution, identical substitution, or the maximum number of permutations allowed. Claim 10 In paragraph 1, the part in Formula I OLED selected from a group consisting of: Here, A and B are each independently monocyclic or multicyclic ring systems comprising one or more fused pentagonal or hexavalent carbocyclic or heterocyclic rings; X is each independently selected from the group consisting of C and N; Y is each independently selected from the group consisting of CRR', SiRR', NR, BR, O, S, Se, and PR; R and R' are each independently representing unsubstituted, monosubstituted, or the maximum number of substitutions allowed; R and R' are each independently hydrogen or substituents selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof. Claim 11 In claim 1, the OLED wherein the first compound of Formula I is selected from the group consisting of the following: Claim 12 In claim 1, the OLED in which the light-emitting region includes an acceptor. Claim 13 An OLED according to claim 1, wherein the light-emitting region comprises a first organic layer and a second organic layer, the first organic layer comprises a first compound and the second organic layer comprises an acceptor. Claim 14 In paragraph 1, the acceptor is an OLED selected from the group consisting of: Here, rings A to I are each independently monocyclic or multicyclic ring systems comprising one or more fused pentagonal or hexacyclic carbocyclic or heterocyclic rings; each of R, M, X, and Y may be the same or different; and Z is each independently selected from the group consisting of B, CR, SiR, and N. Claim 15 In paragraph 1, the acceptor is an OLED selected from the group consisting of: Claim 16 In claim 13, the OLED is doped into the light-emitting layer with the first compound of Formula I at a concentration ranging from 1 weight% to 25 weight%. Claim 17 In claim 16, the acceptor is doped into the light-emitting layer at a concentration ranging from 0.1% to 5%, in the OLED. Claim 18 In Clause 16, the light-emitting layer additionally comprises a host OLED. Claim 19 A consumer product comprising the OLED of claim 1, selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lights, head-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, mobile phones, tablets, phablets, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays with a diagonal of less than 2 inches, 3D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays tiled together, theater or stadium screens, phototherapy devices, and signage. Claim 20 Compound comprising the first structure of Formula VI below: Here, M is selected from the group consisting of Cu, Ag and Au; X 1' is selected from the group consisting of CRR', NR, O, S, SiRR', BR, and GeRR';Y 1' is selected from the group consisting of C, N, B, O, S, Si, and Se; R, R', R A' , R B' , R C' , R D' and R E' are each independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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; R, R', R A' , R B' , R C' , R D' and R E' At least one of which comprises a chemical group capable of emitting light by fluorescence or delayed fluorescence and / or an organic linking bridge comprising 1 to 24 carbon atoms between the organometallic moiety and the fluorescent moiety; a part in Formula VI ...does not contain a carbazole structure; n is 0, 1, or 2; represents a single bond or a double bond; one or more additional structures having Formula VI may be connected or fused with the first structure; and R, R', R A' , R B' , R C' , R D' and R E' Two or more of them can be connected or fused to form a ring.

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