Organic electroluminescent materials and devices

Abstract

This application relates to organic electroluminescent materials and devices. Disclosed is a compound comprising a structure of Formula I. In Formula I, each of Y A , Y B , Y C , and Y D is independently a linking group which can be substituted; at least one of R 1 , R 2 , R 3 , or R 4 is or includes an electron withdrawing group; each substituent is independently hydrogen or a substituent selected from the group consisting of the generic substituents defined herein; and any two substituents can be joined or fused to form a ring. OLEDs and consumer products containing the compounds are also provided.

Description

Cross-reference of related applications

[0001] This application claims priority to U.S. Provisional Application No. 63 / 773,733, filed March 18, 2025, pursuant to 35 USC § 119(e), the entire contents of which are incorporated herein by reference. Technical Field

[0002] This disclosure generally relates to novel device architectures and OLED devices having those novel architectures and their applications. Background Technology

[0003] For various reasons, optoelectronic devices utilizing organic materials are becoming increasingly popular. Many of the materials used to manufacture these devices are relatively inexpensive, thus organic optoelectronic devices have the potential to offer a cost advantage over inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, organic scintillators, and organic photodetectors. For OLEDs, organic materials can offer performance advantages over conventional materials.

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

[0005] One application of emitting molecules is in full-color displays. Industry standards for such displays require pixels suited to emitting specific colors (called "saturated" colors). Specifically, these standards require pixels saturated with red, green, and blue light. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emission. The same technology can be used for OLEDs. White OLEDs can be single-emitting-layer (EML) devices or stacked structures. Color can be measured using the CIE coordinate system, well-known in the field. Summary of the Invention

[0006] In one aspect, a subset I is provided Compounds with the structure of . In Formula I:

[0007] Y A Y B Y C and Y DEach of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR';

[0008] R A R B and R C Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0009] Each R, R', R 1 R 2 R 3 R 4 R A R B and R C Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof;

[0010] R 1 R 2 R 3 Or R 4 At least one of them is an electron-withdrawing group; and

[0011] Any two substituents can join or fuse to form a ring.

[0012] On the other hand, an organic light-emitting device (OLED) is provided, the OLED comprising an anode; a cathode; and an emitting region disposed between the anode and the cathode, wherein the emitting region contains a compound comprising a structure of Formula I described herein.

[0013] In another aspect, a consumer product is provided, wherein the consumer product includes an organic light-emitting device (OLED), the organic light-emitting device including an anode; a cathode; and an emitting region disposed between the anode and the cathode, wherein the emitting region contains a compound comprising a structure of Formula I described herein. Attached Figure Description

[0014] Figure 1 An organic light-emitting device is shown.

[0015] Figure 2 An inverted organic light-emitting device without an independent electron transport layer is demonstrated.

[0016] Figure 3 A model of p-polarized photoluminescence relative to an angle is shown for emitters with different vertical dipole ratios (VDRs). Detailed Implementation

[0017] A. Terminology

[0018] Unless otherwise specified, the following terms as used herein are defined as follows:

[0019] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "placed" "above" the second layer, the first layer is placed further away from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode can still be described as being "placed" "above" the anode.

[0020] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0021] As used herein, and as will generally be understood by those skilled in the art, if the first energy level is closer to the vacuum level, then the first "Highest Occupied Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO) level is "greater than" or "higher than" the second HOMO or LUMO level. Since the ionization potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with the vacuum level at the top, the LUMO levels of a material are higher than the HOMO levels of the same material. A "higher" HOMO or LUMO level appears to be closer to the top of this diagram than a "lower" HOMO or LUMO level.

[0022] As used herein, and as those skilled in the art will generally understand, if the first work function has a higher absolute value, then the first work function is “greater” or “higher” than the second work function. This is because the work function is typically measured as a negative number relative to the vacuum level, meaning that the “higher” work function is more negative. On a conventional energy level diagram with the vacuum level at the top, the “higher” work function is illustrated as being farther from the vacuum level in the downward direction. Therefore, the definitions of HOMO and LUMO levels follow different rules than those for the work function.

[0023] The terms “halogen,” “halogen,” and “halogen group” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0024] The term "acyl" refers to a substituted carbonyl group (-C(O)-R). s ).

[0025] The term "ester" refers to a substituted oxycarbonyl group (-OC(O)-R). s or -C(O)-OR s ) group.

[0026] The term "ether" refers to -OR s Group.

[0027] The terms "thio-" or "thioether" are used interchangeably and refer to -SR s Group.

[0028] The term "selenyl" refers to -SeR s Group.

[0029] The term "sulfinyl" refers to -S(O)-R s Group.

[0030] The term "sulfonyl" refers to -SO2-R s Group.

[0031] The term "phosphono" refers to a group containing at least one phosphorus atom bonded to the relevant structure. Common examples of phosphono groups include, but are not limited to, -P(R) s )2 group or -PO(R s )2 groups, wherein each R s They can be the same or different.

[0032] The term "silyl group" refers to a group containing at least one silicon atom bonded to the relevant structure. Common examples of silyl groups include, but are not limited to, -Si(R s )3 groups, wherein each R s They can be the same or different.

[0033] The term "germanium alkyl" refers to a group containing at least one germanium atom bonded to the relevant structure. Common examples of germanium alkyl groups include, but are not limited to, -Ge(R s )3 groups, wherein each R s They can be the same or different.

[0034] The term "boronyl" refers to a group containing at least one boron atom bonded to the relevant structure. Common examples of boronyl groups include, but are not limited to, -B(R s )2 group or its Lewis adduct -B(R s )3 groups, of which R s They can be the same or different.

[0035] In each of the above, R s It can be hydrogen or a substituent selected from the group of general substituents as defined in this application. Preferred R s Selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. More preferably, R s Choose from the following groups: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0036] The term "alkyl" refers to and includes both straight-chain and branched alkyl groups having alkyl carbon atoms bonded to the relevant structure. Preferred alkyl groups are those containing one to fifteen carbon atoms, more preferably one to nine carbon atoms, and include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,3-dimethylpropyl, 1,1-dimethylpropyl, 2-ethylpropyl, 1,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3-ethylpentyl, 2,2,3-trimethylbutyl, etc. In addition, alkyl groups can be further substituted.

[0037] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spirocyclic alkyl groups having cycloalkyl carbon atoms bonded to the relevant structure. Preferred cycloalkyl groups are those containing 3 to 12 cyclic carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Furthermore, the cycloalkyl group may be further substituted.

[0038] The terms "heteroalkyl" or "heterocyclic alkyl" refer to an alkyl or cycloalkyl group having at least one carbon atom substituted with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Furthermore, the heteroalkyl or heterocyclic alkyl group may be further substituted.

[0039] The term "alkenyl" refers to and includes both straight-chain and branched olefin groups. An alkenyl is essentially an alkyl group comprising at least one carbon-carbon double bond in an alkyl chain, wherein one carbon atom originates from a carbon-carbon double bond bonded to the associated structure. A cycloalkenyl is essentially a cycloalkyl group comprising at least one carbon-carbon double bond in a cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group having at least one carbon atom substituted by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, Ge, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing two to fifteen carbon atoms. Furthermore, alkenyl, cycloalkenyl, or heteroalkenyl groups may be further substituted.

[0040] The term "alkynyl" refers to and includes both straight-chain and branched alkyne groups. An alkynyl group is essentially an alkyl group comprising at least one carbon-carbon triple bond in an alkyl chain, where one carbon atom originates from a carbon-carbon triple bond bonded to the relevant structure. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Furthermore, the alkynyl group may be further substituted.

[0041] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an aryl-substituted alkyl group having an alkyl carbon atom bonded to the relevant structure. Furthermore, aralkyl groups may be further substituted.

[0042] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, Se, N, P, B, Si, Ge, and Se, preferably O, S, N, or B. Heteroaromatic cyclic groups can be used interchangeably with heteroaryl groups. Preferred non-aromatic heterocyclic groups are non-aromatic heterocyclic groups containing 3 to 10 ring atoms, preferably non-aromatic heterocyclic groups containing 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines such as morpholino, piperidinyl, pyrrolyl, etc., and cyclic ethers / thioethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Furthermore, the heterocyclic group may be further substituted or fused.

[0043] The term "aryl" refers to and includes both monocyclic and polycyclic aromatic hydrocarbon groups. A polycyclic aromatic hydrocarbon can have two or more rings, wherein two carbons are common to two adjacent rings (the rings are "fused"). Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty-four carbon atoms, six to eighteen carbon atoms, and more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, twelve, fourteen, or eighteen carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, pyrene, β-carotene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, and naphthalene. Furthermore, aryl groups can be further substituted or fused, such as, but not limited to, fluorene.

[0044] The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom. Heteroatoms include, but are not limited to, O, S, Se, N, P, B, Si, Ge, and Se. In many cases, O, S, N, or B are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Polycyclic heterocyclic systems may have two or more aromatic rings, wherein two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is a heteroaryl. Polycyclic heteroaromatic ring systems may have one to six heteroatoms in each ring. Preferred heteroaryls are those containing three to thirty carbon atoms, preferably three to twenty-four carbon atoms, three to eighteen carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, Indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, aziborane, cycloborane, 5λ 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium and 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene; preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazolium, pyridine, triazine, benzimidazole, 5λ2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo[3,2-a]imidazo[3,2,1-de]anthracene. Additionally, heteroaryl groups can be further substituted or fused.

[0045] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, benzimidazole, and 5λ are included. 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene groups, and their corresponding aza analogs are of particular interest.

[0046] In many cases, the general substituents are selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenyl, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0047] In some cases, preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thioyl, and combinations thereof.

[0048] In some cases, more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, germanyl, boronyl, aryl, heteroaryl, nitrile, thio, and combinations thereof.

[0049] In some cases, even more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitriles and combinations thereof.

[0050] In other cases, the most preferred general substituent is selected from the group consisting of: deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0051] In the absence of a specific definition of one or more substituents (e.g., R, R', R", R), A R AR 1 In the case of R1, etc., each of the one or more substituents should be understood to independently represent hydrogen or a substituent selected from the group consisting of general substituents as defined herein. Similarly, each of the one or more substituents may optionally be coupled or fused with another substituent to form a ring. It should also be understood that any substituent selected from general substituents as defined herein may also be selected from preferred general substituents as defined herein, more preferred general substituents as defined herein, even more preferred general substituents as defined herein, or most preferred general substituents as defined herein.

[0052] The terms "substituted" and "substituted" refer to substituents other than H being bonded to the relevant position, such as carbon or nitrogen. For example, when R... 1 When representing monosubstitution, then an R 1 It must not be H (i.e., substitution). Similarly, when R 1 When representing disubstituted substitution, then the two Rs 1 It must not be H. Similarly, when R... 1 When R represents zero or no substitution, 1 For example, it could be hydrogen atoms with all available valences in the ring atom, such as carbon atoms in benzene and nitrogen atoms in pyrrole, or simply none for ring atoms with fully saturated valences, such as nitrogen atoms in pyridine. The maximum possible number of substitutions in a ring structure will depend on the total number of available valences in the ring atoms.

[0053] As used herein, “combination thereof” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl groups can be combined to form haloalkyl substituents; and halogen, alkyl, and aryl groups can be combined to form haloaralkyl groups. In one instance, the term substitution includes a combination of two to four listed groups. In another instance, the term substitution includes a combination of two to three groups. In yet another instance, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations containing up to forty atoms that are not hydrogen or deuterium, or combinations containing up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0054] The term "aza" in the phrases used herein, namely aza-dibenzofuran, aza-dibenzothiophene, etc., implies that one or more of the CH groups in the corresponding aromatic ring can be substituted with nitrogen atoms. For example, and without limitation, azatriphenylene covers dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derived compounds described above will be readily contemplated by those skilled in the art, and all such analogs are intended to be covered by the terminology set forth herein.

[0055] This disclosure includes all compounds of this disclosure with acceptable isotopic labeling, wherein one or more atoms are replaced by atoms having the same atomic number but with an atomic mass or mass number different from those normally found in nature.

[0056] Examples of suitable isotopes to be included in compounds of this disclosure include isotopes of hydrogen, for example... 2 H and 3 H; isotopes of carbon, such as 11 C 13 C and 14 C; isotopes of chlorine, for example 36 Cl; isotopes of fluorine, for example 18 F; Isotopes of iodine, for example 123 I, 124 I and 125 I; Isotopes of nitrogen, such as 13 N and 15 N; isotopes of oxygen, such as 15 O、 17 O and 18 O; isotopes of phosphorus, such as 32 P; and isotopes of sulfur, such as 35 S.

[0057] Certain isotopically labeled compounds disclosed herein, such as those doped with radioactive isotopes, can be used in diagnostics and other research. Radioactive isotope tritium (i.e., 3 H) and carbon-14 (i.e. 14 C) It is particularly suitable for this purpose due to its ease of incorporation and convenient detection methods.

[0058] Using heavier isotopes such as deuterium (i.e., 2 H) replacement can provide some advantages resulting from greater stability, and may therefore be preferred in some cases.

[0059] The isotopically labeled compounds disclosed herein can generally be prepared by conventional techniques known to those skilled in the art or by methods similar to those described in the appended examples and preparations, using a suitable isotopically labeled reagent instead of the previously used unlabeled reagent.

[0060] For example, deuterated compounds can be readily prepared using methods known in the art. For instance, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterated organometallic complexes. Further references to Ming Yan et al., Tetrahedron 2015, 71, 1425-30, and Atzrodt et al., Angewandte Chemie International Edition (Review) 2007, 46, 7744-65 (which are incorporated herein by reference in their entirety) describe efficient pathways for the deuteration of methylene hydrogen in benzylamine and the replacement of aromatic cyclic hydrogens with deuterium, respectively.

[0061] As used herein, any specifically listed substituent, such as, but not limited to, methyl, phenyl, pyridyl, etc., includes its undeuterated, partially deuterated, and fully deuterated forms. Similarly, substituents, such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc., also include their undeuterated, partially deuterated, and fully deuterated forms. Unless otherwise specified, atoms in a chemical structure that are not completely filled with H or D should be considered to include their undeuterated, partially deuterated, and fully deuterated forms. For example, chemical structures This means including C6H6, C6D6, C6H3D3, and any other partially deuterated variants thereof. Some common basic partially or fully deuterated groups include, but are not limited to, CD3, CD2C(CH3)3, C(CD3)3, and C6D5. Similarly, where the partially or fully defined atomic structure indicates that a particular position can be deuterated, it is also conceivable to have the same atomic structure with one, two, or at most all deuterated atoms replaced by hydrogen.

[0062] It should be understood that when a molecular fragment is described as a substituent or additionally attached to another group, its name can be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attached fragments are considered equivalent.

[0063] In some cases, a pair of substituents in a molecule may join or fuse to form a ring. Preferred rings are five- to nine-membered carbon rings or heterocycles, including both cases where the ring formed by the pair of substituents is partially saturated and partially unsaturated. In other cases, a pair of adjacent substituents may join or fuse to form a ring. As used herein, “adjacent” means that the two substituents involved may be adjacent to each other on the same ring, or on two neighboring rings having two closest available substituted positions (such as the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene).

[0064] This document may describe light emission regions by referring to the color of the light emitted by layers, materials, areas, and devices. Generally, as used herein, an emitting region that produces a particular color of light may include one or more emitting layers disposed in a stacked manner on top of each other.

[0065] As used herein, “NIR,” “red,” “green,” “blue,” and “yellow” layers, materials, regions, or devices refer to layers, materials, regions, or devices that emit light in the wavelength ranges of approximately 700–1500 nm, 580–700 nm, 500–600 nm, 400–500 nm, and 540–600 nm, respectively, or layers, materials, regions, or devices that have the highest emission spectral peak in the corresponding wavelength regions. In some arrangements, individual regions, layers, materials, or devices may provide separate “deep blue” and “light blue” emissions. As used herein, a “deep blue” emission component refers to an emission whose peak emission wavelength is at least approximately 4 nm smaller than the peak emission wavelength of the “light blue” emission component. Typically, the peak emission wavelength of the “light blue” emission component is in the range of approximately 465–500 nm, and the peak emission wavelength of the “deep blue” emission component is in the range of approximately 400–470 nm, but these ranges may vary for some configurations.

[0066] In some arrangements, a color-changing layer is provided that converts, modifies, or alters the color of light emitted by another layer to emit light with a different wavelength. This color-changing layer can be configured to shift the wavelength of light emitted by the other layer by a defined amount, such as by the difference between the wavelength of the emitted light and the wavelength of the resulting light. Generally, there are two types of color-changing layers: color filters that modify the spectrum by removing light of unwanted wavelengths, and color-changing layers that convert higher-energy photons into lower-energy ones. For example, a "red" filter may be present to filter input light to remove light with wavelengths outside the approximately 580-700 nm range. The component of "color" refers to the component of light that produces or otherwise emits a specific color as described above when activated or used. For example, "a first emission region of a first color" and "a second emission region of a second color different from the first color" describe two emission regions that emit two different colors as described above when activated within the device.

[0067] As used herein, the light initially generated by a material, layer, or region is the exact opposite of the light ultimately emitted by the same or different structures, allowing the emitting materials, layers, and regions to be distinguished from each other and from other structures. Initial light generation is typically a result of energy level changes that lead to photon emission. For example, an organic emitting material may initially produce blue light, which can be converted into red or green light by a color filter, quantum dot, or other structure, causing the entire emitting stack or subpixel to emit red or green light. In this case, the initial emitting material or layer may be referred to as the "blue" component, even if the subpixel is the "red" or "green" component.

[0068] In some cases, the color of components, such as the color of emitting regions, subpixels, color-changing layers, etc., can preferably be described according to 1931 CIE coordinates. For example, a yellow emitting material may have multiple peak emission wavelengths, one in or near the edge of the "green" region and one in or near the edge of the "red" region, as previously described. Therefore, as used herein, each color item also corresponds to a shape in the 1931 CIE coordinate color space. The shape in the 1931 CIE color space is constructed by tracing the trajectory between two color points and any other interior points. For example, the interior shape parameters for red, green, blue, and yellow can be defined as follows:

[0069]

[0070] Further details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0071] As disclosed herein, the emission layer or material (e.g. Figure 1-2The emitting layers 135 and 220 shown herein may include quantum dots. Unless explicitly indicated otherwise or as understood by one of ordinary skill in the art, the term "emitting layer" or "emitting material" as disclosed herein may include organic emitting materials and / or emitting materials containing quantum dots or equivalent structures. Generally, an emitting layer comprises emitting material within a host matrix. Such an emitting layer may comprise only quantum dot material that converts light emitted by a separate emitting material or other emitting body, or it may also comprise a separate emitting material or other emitting body, or it may emit light directly by applying an electric current. Similarly, color-changing layers, filters, upconversion or downconversion layers, or structures may comprise materials containing quantum dots, but such layers are not considered "emitting layers" as disclosed herein. Typically, an "emitting layer" or material is a material that emits initial light based on injected charge, wherein the initial light may be altered by another layer, such as a filter or other color-changing layer, which does not itself emit the initial light within the device but may re-emit altered light with different spectral content based on absorption and downconversion of the initial light emitted by the emitting layer to lower energy light emission. In some embodiments disclosed herein, color-changing layers, color filters, up-conversion and / or down-conversion layers may be disposed outside the OLED device, for example, above or below the electrodes of the OLED device.

[0072] Unless otherwise specified, any of the layers in the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet printing (as described in U.S. Patent Nos. 6,013,982 and 6,087,196, which are incorporated herein by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Patent No. 6,337,102 by Forrest et al., which is incorporated herein by reference in its entirety), and deposition via organic vapor jet printing (OVJP, also known as organic vapor jet deposition (OVJD)) (as described in U.S. Patent No. 7,431,968, which is incorporated herein by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably performed in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition via a mask, cold soldering (as described in U.S. Patents 6,294,398 and 6,468,819, which are incorporated herein by reference in their entirety), and patterning associated with some of the deposition methods such as inkjet and OVJD. Other methods may also be used. The material to be deposited may be modified to suit a particular deposition method. For example, branched or unbranched substituents, preferably containing at least three carbons, such as alkyl and aryl groups, may be used in small molecules to enhance their solution handling ability. Substituents having 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Materials with asymmetric structures may have better solution handleability than those with symmetric structures because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the solution handling ability of small molecules.

[0073] The device manufactured according to embodiments of this disclosure may optionally further include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage caused by exposure to harmful substances in an environment including moisture, vapors, and / or gases. The barrier layer may be deposited above, below, or adjacent to a substrate or electrode, or above any other part of the device, including edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed using various known chemical vapor deposition techniques and may comprise compositions having a single phase and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. Inorganic or organic compounds, or both, may be incorporated into the barrier layer. Preferred barrier layers comprise multiple alternative layers of materials including: polymeric and nonpolymeric materials; organic and inorganic materials; or mixtures of polymeric and nonpolymeric materials, an example of which is described in U.S. Patent No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entirety.

[0074] Devices manufactured according to embodiments of this disclosure can be incorporated into a wide variety of electronic component modules (or units), which can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include displays, lighting devices (such as discrete light source devices or lighting panels), etc., which can be utilized by end-user product manufacturers. The electronic component module may optionally include driving electronics and / or a power supply. Devices manufactured according to embodiments of this disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. A consumer product incorporating an OLED is disclosed, wherein the OLED includes compounds of this disclosure in its organic layer. The consumer product should include any type of product containing one or more light sources and / or one or more of some type of visual display. Examples of the consumer products described include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external lighting and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays with a diagonal of less than 2 inches, 3D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple tiled displays, theater or stadium screens, and signage. Various control mechanisms, including passive and active matrices, can be used to control devices manufactured according to this disclosure. Many of the devices are intended for use in temperature ranges comfortable for humans, such as 18°C ​​to 30°C, and more preferably at room temperature (20-25°C), but can be used outside this temperature range (e.g., -40°C to 80°C).

[0075] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can utilize the materials and structures described herein. More generally, organic devices such as organic transistors can utilize the materials and structures described herein.

[0076] In general terms in this field, a "subpixel" can refer to an emission region combined with any color-changing layer, such as a single-layer EML, a stacked device, etc., whereby the color-changing layer is used to adjust the color emitted by the emission region.

[0077] As used herein, an “emitting region” of a subpixel refers to any and all emitting layers, regions, and means in the subpixel that are initially used to generate light. A subpixel may also include other layers stacked with the emitting region that affect the final color produced by the subpixel, such as color-changing layers disclosed herein, but such color-changing layers are typically not considered “emitting layers” as disclosed herein. A non-filtering subpixel is a subpixel that excludes color adjustment components (e.g., color-changing layers) but may include one or more emitting regions, layers, or means.

[0078] In some configurations, an "emitting region" may include emitting materials that emit multiple colors of light. For example, a yellow emitting region may include multiple materials that emit red and green light when each material is used individually in an OLED device. When used in a yellow device, individual materials are typically not arranged such that they can be individually activated or addressed. That is, a "yellow" OLED stack containing said materials cannot be driven to produce red, green, or yellow light; in fact, the stack can be driven as a whole to produce yellow light. Such an emitting region may be referred to as a yellow emitting region, although the stack does not directly produce yellow light at the level of individual emitters. As described in more detail below, the individual emitting materials used in the emitting region (if more than one) may be placed in the same emitting layer within the device, or in multiple emitting layers within an OLED device containing the emitting region. As described in more detail below, the embodiments disclosed herein may provide an OLED device (e.g., a display) that includes a limited number of colors of emitting regions, while also including subpixels or other OLED devices with more colors than the number of colors of the emitting regions. For example, a device as disclosed herein may include only blue and yellow emitting regions. Other colors of subpixels can be achieved by using color-changing layers (e.g., color-changing layers stacked with yellow or blue emitting regions), or more generally, by using color-changing layers, electrodes, or other structures forming microcavities as disclosed herein, or any other suitable configuration. In some cases, the general color provided by a subpixel may be the same as the color provided by the emitting regions in the stack defining the subpixel, for example, where a dark blue color-changing layer is stacked with a light blue emitting region to produce a dark blue subpixel. Similarly, the color provided by a subpixel may be different from the color provided by the emitting regions in the stack defining the subpixel, for example, where a green color-changing layer is stacked with a yellow emitting region to produce a green subpixel.

[0079] In some configurations, the emission region and / or emission layer can span multiple sub-pixels, for example, where the fabrication of other layers and circuitry allows for the addressing of individual portions of the emission region or layer.

[0080] The emission regions disclosed herein may differ from emission “layers” typically referred to in the art and used herein. In some cases, a single emission region may comprise multiple layers, for example, where a yellow emission region is formed by sequentially depositing red and green emission layers. As previously described, when such layers are present in emission regions as disclosed herein, the layers are not individually addressable within a single emission stack; in fact, the layers are activated or driven in parallel to produce light of the desired color from the emission region. In other configurations, the emission region may comprise a single emission layer of a single color, or multiple emission layers of the same color, in which case the color of such emission layers will be the same as, or within the same spectral range as, the color of the emission region in which the emission layers are housed.

[0081] B. The compounds, OLEDs, and devices disclosed herein

[0082] 1. compound

[0083] In some embodiments, a included I is provided Compounds with the structure of . In Formula I:

[0084] Y A Y B Y C and Y D Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR';

[0085] R A R B and R C Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0086] Each R, R', R 1 R 2 R 3 R 4 R A R B and R C Substituents that are independently hydrogen or selected from the group of universal substituents as defined herein;

[0087] R 1 R 2 R 3 Or R 4 At least one of them is or contains an electron-withdrawing group; and

[0088] Any two substituents can join or fuse to form a ring.

[0089] In some embodiments, the compound consists essentially of Formula I as defined herein.

[0090] In some embodiments, the compound has the structure of Formula I as defined herein.

[0091] In some embodiments, the limitation is when Y A Y B Y C and Y D Each is NR, and R 1 and R 2 When both are CN, then R 3 and R 4 At least one of them is not hydrogen or R contains a C2-C30 alkyl or heterocyclic group.

[0092] In some embodiments, R 1 R 2 R 3 Or R 4 At least one of them contains an electron-withdrawing group with a Hammett constant greater than 0. In some embodiments, R 1 R 2 R 3 Or R 4 At least one of them contains an electron-withdrawing group with a Hammett constant equal to or greater than 0.1, or at least 0.2, or at least 0.3, or at least 0.4, or at least 0.5, or at least 0.6, or at least 0.7, or at least 0.8, or at least 0.9, or at least 1.0, or at least 1.1.

[0093] In some embodiments, the compound is not , or .

[0094] In some embodiments, at least one R, R', R 1 R 2 R 3 R 4 R A R B and R C It is partially or completely deuterated.

[0095] In some embodiments, at least one R A It is partially or fully deuterated. In some embodiments, at least one R B It is partially or fully deuterated. In some embodiments, at least one R CIt is partially or fully deuterated. In some embodiments, R 1 R 2 R 3 Or R 4 At least one of them is partially or fully deuterated. In some embodiments, at least one of R or R' is partially or fully deuterated.

[0096] In some embodiments, at least one R 1 R 2 R 3 R 4 R A R B Or R C Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R A Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R B Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R C Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R 1 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R 2 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R 3 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R 4 Selected from the group consisting of universal substituents as defined herein. In some embodiments, at least one R 1 R 2 R 3 R 4 R A R B Or R C Choose from the group of preferred general substituents as defined herein.

[0097] In some embodiments, each R, R', R 1 R 2 R 3 R 4 R A R B and R C Independently, it is hydrogen or a substituent selected from the group of preferred general substituents as defined herein. In some embodiments, each R, R', R 1 R 2 R 3 R 4 RA R B and R C Substituents that are independently hydrogen or selected from the group consisting of more preferred general substituents as defined herein. In some embodiments, each R, R', R 1 R 2 R 3 R 4 R A R B and R C Substituents that are independently hydrogen or selected from the group consisting of even more preferred general substituents as defined herein. In some embodiments, each R, R', R 1 R 2 R 3 R 4 R A R B and R C Substituents that are independently hydrogen or selected from the group of most preferred general substituents as defined herein.

[0098] In some embodiments, Y A Y B Y C Or Y D At least one of them is O, S, Se, NR, BR, BRR', PR, PRR', CR, CRR', S=O, SO2, P(O)R, SiRR', or GeRR'.

[0099] In some embodiments, Y A Y B Y C Or Y D At least one of them is O, S, or Se. In some embodiments, Y A Y B Y C Or Y D At least two of them are independently O, S, or Se.

[0100] In some embodiments, Y A Y B Y C Or Y D At least one of them is O. In some embodiments, Y A Y B Y C Or Y D At least two of them are O.

[0101] In some embodiments, Y A Y B Y C Or YD At least one of them is NR, BR, or PR. In some embodiments, Y A Y B Y C Or Y D At least two of them are independently NR, BR, or PR.

[0102] In some embodiments, Y A Y B Y C Or Y D At least one of them is NR. In some embodiments, Y A Y B Y C Or Y D At least two of them are NR. In some embodiments, Y A Y B Y C Or Y D At least two of them are 0. In some embodiments, Y A Y B Y C Or Y D At least three of them are NR. In some embodiments, Y A Y B Y C and Y D Each of them is NR.

[0103] In some embodiments, Y A Y B Y C Or Y D At least one of them is S=O, SO2, or P(O)R. In some embodiments, Y A Y B Y C Or Y D At least two of them are independently S=O, SO2, or P(O)R.

[0104] In some embodiments, Y A Y B Y C Or Y D At least one of them is PRR', CRR', BRR', SiRR', or GeRR'. In some embodiments, Y A Y B Y C Or Y D At least two of them are independently PRR', CRR', BRR', SiRR', or GeRR'.

[0105] In some embodiments, YA Y B Y C Or Y D At least one of them is CR. In some embodiments, Y A Y B Y C Or Y D At least two of them are CR.

[0106] In some embodiments, there is no R or R' with R A R B Or R C Joining or fused to form a ring. In some embodiments, no R or R' joins or fused with another R or R' to form a ring.

[0107] In some embodiments, Y A Y B Y C and Y D Each of these is independently either O or NR. In some embodiments, Y A Y B Y C and Y D Two of them are 0, and the other two are NR. In some embodiments, Y A and Y D It is NR, and Y C and Y D It is O.

[0108] In some embodiments, Y A Y B Y C Or Y D At least one of them contains an electron-donating group. In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain electron-donating groups. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain electron-donating groups. In some embodiments, Y A Y B Y C Or Y D Each of them independently contains an electron-donating group.

[0109] In some embodiments, Y A Y B Y C Or Y DAt least one of them is an electron-donating group. In some embodiments, Y A Y B Y C Or Y D At least two of them are independently electron-donating groups. In some embodiments, Y A Y B Y C Or Y D At least three of them are independently electron-donating groups. In some embodiments, Y A Y B Y C Or Y D Each of them is an electron-donating group.

[0110] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, where R is a benzene ring para-substituted with an electron-donating group. In some such embodiments, Y A Y B Y C Or Y D At least one of them is NR.

[0111] In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, where R is a benzene ring para-substituted with an electron-donating group. In some such embodiments, Y A Y B Y C Or Y D Each of the at least two mentioned in the text is an NR.

[0112] In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, where R is a benzene ring para-substituted with an electron-donating group. In some such embodiments, Y A Y B Y C Or Y D Each of the at least three mentioned is an NR.

[0113] In some embodiments, Y A Y B Y C and Y DEach of these elements independently contains R, which is a benzene ring para-substituted with an electron-donating group. In some such embodiments, Y A Y B Y C and Y D Each of them is NR.

[0114] In any of the above embodiments, at least one R is 4-tert-butylbenzene. In any of the above embodiments, at least one R is 4-methoxybenzene. In any of the above embodiments, at least one R is 1,3,5-triphenylamine. In any of the above embodiments, at least one R is 3,5-di-tert-butylbenzene.

[0115] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, wherein R is a 6-membered aromatic ring having at least one substituted position at the α-bond or adjacent position. In some embodiments, Y A Y B Y C Or Y D At least one of them is NR. In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, wherein R is a 6-membered aromatic ring having two substituted rings at the α-bond adjacent position.

[0116] As used in this article, Y A To Y D The α-bond of a group is a bond that connects an atom (e.g., N, P, C in the following examples) to a substituent (e.g., the NR bond of NR, the PR bond of PRR', the CR bond of CR, etc.).

[0117] In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, wherein R is a 6-membered aromatic ring having at least one substituted position at the α-bond or adjacent. In some embodiments, Y A Y B Y C Or Y D Each of the at least two mentioned above is NR. In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, which is a 6-membered aromatic ring having two substituted rings at the α-bond ortho position.

[0118] In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, where R is a 6-membered aromatic ring having at least one substituted position at the α-bond or adjacent. In some embodiments, Y A Y B Y C Or Y D Each of the at least three mentioned above is an NR. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, which is a 6-membered aromatic ring with two substituted rings at the α-bond ortho position.

[0119] In some embodiments, Y A Y B Y C and Y D Each of them independently contains R, which is a 6-membered aromatic ring having at least one substitution at the α-bond or adjacent position. In some embodiments, Y A Y B Y C and Y D Each of them is NR. In some embodiments, Y A Y B Y C and Y D Each of them independently contains R, which is a 6-membered aromatic ring with two substituted members at the α-bond adjacent position.

[0120] In any of the above embodiments, at least one R is 2,6-diphenylphenyl. In any of the above embodiments, at least one R is 2-alkyl,6-arylbenzene. In any of the above embodiments, at least one R is 2-methyl,6-phenylbenzene. In any of the above embodiments, at least one R is 2,6-dialkylbenzene. In any of the above embodiments, at least one R is 2,6-dimethylbenzene.

[0121] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, where R is a multi-ring fused ring system. In some embodiments, Y A Y B Y C Or Y DAt least two of them independently contain R, where R is a multi-ring fused ring system. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, where R is a multi-ring fused ring system. In some embodiments, Y A Y B Y C and Y D Each of the components independently contains R, where R is a polycyclic fused ring system. In some embodiments, any of the polycyclic fused ring systems may be aromatic. In some embodiments, any of the polycyclic fused ring systems may be non-aromatic.

[0122] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, where R is carbazole or dibenzofuran. In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, where R is carbazole or dibenzofuran. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, where R is carbazole or dibenzofuran. In some embodiments, Y A Y B Y C and Y D Each of these components independently contains R, where R is carbazole or dibenzofuran. In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding values ​​in the NR can be NR.

[0123] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, wherein R is a non-fused polyaryl group. In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, where R is a non-fused polyaryl group. In some embodiments, Y A Y B Y C Or YD At least three of them independently contain R, where R is a non-fused polyaryl group. In some embodiments, Y A Y B Y C and Y D Each of them independently contains R, where R is a non-fused polyaryl group. In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding values ​​in the NR can be NR.

[0124] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, said R comprising an electron-donating group selected from the group consisting of aryloxy, amino, or a 5-membered aromatic ring containing a heteroatom. In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain R, said R comprising an electron-donating group selected from the group consisting of aryloxy, amino, or a 5-membered aromatic ring containing one heteroatom. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, said R comprising an electron-donating group selected from the group consisting of aryloxy, amino, or a 5-membered aromatic ring containing one heteroatom. In some embodiments, Y A Y B Y C and Y D Each of these groups independently contains R, which comprises an electron-donating group selected from the group consisting of aryloxy, amino, or a 5-membered aromatic ring containing one heteroatom. In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding values ​​in the NR can be NR.

[0125] In some embodiments, Y A Y B Y C Or Y D At least one of them contains R, said R comprising an electron-donating group selected from the group consisting of carbazole, diphenylamino, phenoxazine, phenothiazine, dibenzodiazepine, pyrrolidine, piperidine, phenoxy, and methoxy. In some embodiments, Y A YB Y C Or Y D At least two of them independently contain R, said R comprising an electron-donating group selected from the group consisting of carbazole, diphenylamino, phenoxazine, phenothiazine, dibenzodiazepine, pyrrolidine, piperidine, phenoxy, and methoxy. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain R, said R comprising an electron-donating group selected from the group consisting of carbazole, diphenylamino, phenoxazine, phenothiazine, dibenzodiazeline, pyrrolidine, piperidine, phenoxy, and methoxy. In some embodiments, Y A Y B Y C and Y D Each of these groups independently comprises R, wherein R contains an electron-donating group selected from the group consisting of carbazole, diphenylamino, phenoxazine, phenothiazine, dibenzodiazeline, pyrrolidine, piperidine, phenoxy, and methoxy. In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding values ​​in the NR can be NR.

[0126] In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding elements may include R, where R contains an electron-donating group. In any of the above embodiments, Y A Y B Y C Or Y D One or more of the corresponding groups may include R, where R is an electron donor group.

[0127] In some embodiments, Y A Y B Y C Or Y D At least one of them contains at least one electron donor group selected from the group consisting of structures in List A1 below: , , , , , , , , , , , , , , , , , , , , , , and its substituted or aza-substituted variants;

[0128] Where Y T Y U Y V and Y W Each of them is independently selected from the following groups: BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR', and GeRR';

[0129] Where each R, R' and R T They can be the same or different, and each R T Independently, it is a donor group, an acceptor group, an organic linking group bonded to a donor group, an organic linking group bonded to an acceptor group, or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, aryl, heteroaryl, and combinations thereof; and

[0130] Each R and R' is independently hydrogen or a substituent selected from the group of universal substituents defined herein.

[0131] In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain at least one electron-donating group selected from the group consisting of structures from List A1 as defined herein. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain at least one electron-donating group selected from the group consisting of structures from List A1 as defined herein. In some embodiments, Y A Y B Y C and Y D Each of them independently contains at least one electron donor group selected from the group consisting of structures of List A1 as defined herein.

[0132] In some embodiments, Y A Y B Y C Or Y DAt least one of them contains at least one group selected from the group consisting of the following list A2: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0133] In some embodiments, Y A Y B Y C Or Y D At least two of them independently contain at least one group selected from the group consisting of List A2 as defined herein. In some embodiments, Y A Y B Y C Or Y D At least three of them independently contain at least one group selected from the group consisting of List A2 as defined herein. In some embodiments, Y A Y B Y C Or Y D Each of them independently contains at least one group selected from the group consisting of List A2 as defined herein.

[0134] In some embodiments, the compound contains at least two electron-withdrawing groups. In some embodiments, the compound contains at least three electron-withdrawing groups. In some embodiments, the compound contains at least four electron-withdrawing groups.

[0135] In some embodiments, R 1 R 2 R 3 Or R 4 At least two of them are independently electron-withdrawing groups. In some embodiments, R 1 R 2 R 3 Or R 4 At least three of them are independently electron-withdrawing groups. In some embodiments, R 1 R 2 R 3 and R 4 Each of them is an electron-withdrawing group.

[0136] In some embodiments, R 1 R 2 R 3 Or R 4 At least one of them is an electron-withdrawing group selected from the group consisting of List A2 as defined herein. In some embodiments, R 1 R 2 R 3 Or R 4 At least two of them are independently electron-withdrawing groups selected from the group consisting of List A2 as defined herein. In some embodiments, R 1 R 2 R 3 Or R 4 At least three of them are independently electron-withdrawing groups selected from the group consisting of List A2 as defined herein. In some embodiments, R 1 R 2 R 3 Or R 4 Each of them is independently an electron-withdrawing group selected from the group consisting of the list A2 defined herein.

[0137] In some embodiments, R 1 and R 2 Not CN. In some embodiments, R 1 and R 2 Both are CN, and R 3 Or R 4 At least one of them is not hydrogen. In some embodiments, R 3 Or R 4 At least one of them is a non-hydrogen substituent. In some embodiments, R 3 Or R 4 At least one of them is a 2,6-substituted aryl, silyl, germanyl, or carbazole. In some embodiments, R 3 Or R 4 At least one of them is an EWG. In some embodiments, R 1 -R 4 At least one of them contains a heterocyclic group. In some embodiments, R 1 -R 4 At least one of them is a CN-substituted aryl or heteroaryl group.

[0138] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of the following EWG1 list: F, CF3, CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC. + N(R k2 )3、(R k2 )2CCN、(R k2 )2CCF3、CNC(CF3)2、BR k3 R k2 Substituted or unsubstituted dibenzoboranecyclopentadiene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridoxine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketones, carboxylic acids, esters, nitriles, isonitriles, sulfinyl groups, sulfonyl groups, partially and fully fluorinated alkyl groups, partially and fully fluorinated aryl groups, partially and fully fluorinated heteroaryl groups, cyano-containing alkyl groups, cyano-containing aryl groups, cyano-containing heteroaryl groups, isocyanates, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0139] Each R k1 Indicates single substitution up to the maximum permissible substitution or no substitution;

[0140] Where Y G Choose from the following groups: 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' ;and

[0141] Where R k1 R k2 R k3 R e and R f Each of them is independently hydrogen or a substituent selected from the group of universal substituents defined herein.

[0142] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of structures in the following EWG2 list: , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0143] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of structures in the following EWG3 list: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0144] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of structures in the following EWG4 list: , , , , , , , , , , , , , , , , , , , , , , , and .

[0145] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of structures in the following π-EWG list: CN, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSeO2CF3, OCN, SCN, SeCN, NC. + N(R k2 3. BR k2 R k3Substituted or unsubstituted dibenzoboranecyclopentadiene, 1-substituted carbazole, 1,9-substituted carbazole, substituted or unsubstituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketones, carboxylic acids, esters, nitriles, isonitriles, sulfinyl groups, sulfonyl groups, partially and fully fluorinated aryl groups, partially and fully fluorinated heteroaryl groups, cyano-containing aryl groups, cyano-containing heteroaryl groups, isocyanates, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and The variables are the same as those previously defined.

[0146] In some embodiments, each electron-withdrawing group is independently selected from the group consisting of the structures listed in A3 below: , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , and .

[0147] In some embodiments, R 1 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, R 1 It is or contains electron-withdrawing groups from the EWG2 list as defined herein. In some embodiments, R 1 It is or contains electron-withdrawing groups from the EWG3 list as defined herein. In some embodiments, R 1 It is or contains electron-withdrawing groups from the EWG4 list as defined herein. In some embodiments, R 1 It is or contains electron-withdrawing groups from the π-EWG list as defined herein. In some embodiments, R 1 It is or contains electron-withdrawing groups from List A3 as defined herein.

[0148] In some embodiments, R 2 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, R 2 It is or contains electron-withdrawing groups from the EWG2 list as defined herein. In some embodiments, R 2 It is or contains electron-withdrawing groups from the EWG3 list as defined herein. In some embodiments, R 2 It is or contains electron-withdrawing groups from the EWG4 list as defined herein. In some embodiments, R 2 It is or contains electron-withdrawing groups from the π-EWG list as defined herein. In some embodiments, R 2 It is or contains electron-withdrawing groups from List A3 as defined herein.

[0149] In some embodiments, R 3 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, R 3It is or contains electron-withdrawing groups from the EWG2 list as defined herein. In some embodiments, R 3 It is or contains electron-withdrawing groups from the EWG3 list as defined herein. In some embodiments, R 3 It is or contains electron-withdrawing groups from the EWG4 list as defined herein. In some embodiments, R 3 It is or contains electron-withdrawing groups from the π-EWG list as defined herein. In some embodiments, R 3 It is or contains electron-withdrawing groups from List A3 as defined herein.

[0150] In some embodiments, R 4 It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, R 4 It is or contains electron-withdrawing groups from the EWG2 list as defined herein. In some embodiments, R 4 It is or contains electron-withdrawing groups from the EWG3 list as defined herein. In some embodiments, R 4 It is or contains electron-withdrawing groups from the EWG4 list as defined herein. In some embodiments, R 4 It is or contains electron-withdrawing groups from the π-EWG list as defined herein. In some embodiments, R 4 It is or contains electron-withdrawing groups from List A3 as defined herein.

[0151] In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R A It is or contains an electron-withdrawing group from the list of π-EWG as defined herein. In some embodiments, at least one R A It is or contains electron-withdrawing groups from List A3 as defined herein.

[0152] In some embodiments, at least one R B It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R BIt is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R B It is or contains an electron-withdrawing group from the list of π-EWG as defined herein. In some embodiments, at least one R B It is or contains electron-withdrawing groups from List A3 as defined herein.

[0153] In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG1 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG2 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG3 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the EWG4 list as defined herein. In some embodiments, at least one R C It is or contains an electron-withdrawing group from the list of π-EWG as defined herein. In some embodiments, at least one R C It is or contains electron-withdrawing groups from List A3 as defined herein.

[0154] In some embodiments, no R A It is an electron-withdrawing group. In some embodiments, R is absent. B It is an electron-withdrawing group. In some embodiments, R is absent. C It is an electron-withdrawing group.

[0155] In some embodiments, the compound comprises at least one electron-donating group (EDG) and at least one EWG. In some embodiments, the compound comprises at least two EDGs and at least two EWGs.

[0156] In some embodiments, at least one R A It is not hydrogen. In some embodiments, at least one R A It is neither hydrogen nor deuterium.

[0157] In some embodiments, at least one R A It contains at least one C atom. In some embodiments, at least one R... A It contains at least two C atoms. In some embodiments, at least one R... AIt contains at least three C atoms. In some embodiments, at least one R... A It contains at least four carbon atoms.

[0158] In some embodiments, at least one R A It includes substituents selected from the group consisting of: alkyl, cycloalkyl, silalkyl, germanalkyl, aryl, heteroaryl, and combinations thereof.

[0159] In some embodiments, each R A It is hydrogen.

[0160] In some embodiments, R A With R 1 Or R 2 At least one of them is joined to form a ring. In some embodiments, one R A With R 1 Joined to form a ring and an R A With R 2 Join to form a ring.

[0161] In some embodiments, at least one R B It is not hydrogen. In some embodiments, at least one R B It is neither hydrogen nor deuterium.

[0162] In some embodiments, at least one R B It contains at least one C atom. In some embodiments, at least one R... B It contains at least two C atoms. In some embodiments, at least one R... B It contains at least three C atoms. In some embodiments, at least one R... B It contains at least four carbon atoms.

[0163] In some embodiments, at least one R B It includes substituents selected from the group consisting of: alkyl, cycloalkyl, silalkyl, germanalkyl, aryl, heteroaryl, and combinations thereof.

[0164] In some embodiments, each R B It is hydrogen.

[0165] In some embodiments, R B With Y D Joined to form a ring. In some embodiments, R B With Y D They combine to form carbazole.

[0166] In some embodiments, at least one R C It is not hydrogen. In some embodiments, at least one R C It is neither hydrogen nor deuterium.

[0167] In some embodiments, at least one R C It contains at least one C atom. In some embodiments, at least one R... C It contains at least two C atoms. In some embodiments, at least one R... C It contains at least three C atoms. In some embodiments, at least one R... C It contains at least four carbon atoms.

[0168] In some embodiments, at least one R C It includes substituents selected from the group consisting of: alkyl, cycloalkyl, silalkyl, germanalkyl, aryl, heteroaryl, and combinations thereof.

[0169] In some embodiments, each R C It is hydrogen.

[0170] In some embodiments, R C With Y A Joined to form a ring. In some embodiments, R C With Y A They combine to form carbazole.

[0171] In some embodiments, the HOMO level of the compound is less than -5.1 eV. In some embodiments, the HOMO level of the compound is less than -5.2 eV, or less than -5.3 eV, or even less than -5.4 eV.

[0172] In some embodiments, the peak emission of the compound is less than 540 nm. In some embodiments, the peak emission of the compound is less than 535 nm, or less than 530 nm, or less than 525 nm. In some of the above embodiments, the peak emission was measured at 1% in poly(methyl methacrylate) (PMMA).

[0173] In some embodiments, the peak emission of the compound is at least 500 nm, or at least 510 nm, or at least 515 nm, or even at least 520 nm.

[0174] In some embodiments, the compounds are selected from the group consisting of structures listed in A4 below: , , , , , , , , , , , and ;

[0175] in:

[0176] Y E and Y F Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR';

[0177] R E and R F Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0178] Each R E and R F Substituents that are independently hydrogen or selected from the group of universal substituents as defined herein;

[0179] The remaining variables are the same as those previously defined; and

[0180] Any two substituents can join or fuse to form a ring.

[0181] In some embodiments, when the structure is selected from Listing A4, R 1 It is CN. In some embodiments, R 4 It is CN. In some embodiments, R 1 and R 2 It is CN. In some embodiments, R 3 and R 4 It is CN. In some embodiments, R 1 R 2 R 3 and R 4 All are CN. In some embodiments, all Y A Y B Y C and Y D Each is independently NR, where R is a substituted or unsubstituted phenyl group. In some embodiments, Y A and Y B Each is independently NR, where R is a substituted or unsubstituted phenyl group, and Y is a phenyl group. C and Y D It is O. In some embodiments, Y A and Y B It is O, and Y C and Y D Each is independently NR, where R is a substituted or unsubstituted phenyl group. In some embodiments, all Y A Y B YC and Y D All are O. In some embodiments, all Y A Y B Y C and Y D All are S. In some embodiments, all Y A Y B Y C and Y D Both are Se.

[0182] In some embodiments,The compounds were selected from the following groups: Compound 1 - (Eh)(Ei)(Ej) (Ek)(Rv)(Yl)(Ym)(Yo)(Yp), Compound 2 - (Ei)(Rs)(Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 3 - (Eh)(Ei)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), Compound 4 - (Ei)(Ej)(Ek)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 5 - (Ei)(Ej)(Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 6 - (Eh)(Ek)(Rs)(Rt)(Rv)(Yl)(Ym) (Yo)(Yp), compound 7-(Eh)(Ei)(Ej)(Ek)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), compound 8-(Ei)(Rs)(Rt)(Rv) (Rw)(Yl)(Ym)(Yo)(Yp), compound 9-(Ei)(Ek)(Rs)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), compound 10-(Ei)(Ej) (Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 11-(Ei)(Rv)(Yl), Compound 12-(Ei)(Ek)(Rv)(Yl), Compound 13-(Ei)(Ek)(Rv)(Yl)(Ym), Compound 14-(Ei)(Rv)(Yl)(Ym), Compound 15-(Ei)(Ek)(Rv)(Yl)(Ym), Compound 16-(Ei)(Rv)(Yl)(Ym), Compound 17-(Ei)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), Compound 18-(Ei)(Rv) (Rw)(Yl)(Ym)(Yo)(Yp), Compound 19-(Ei)(Rs)(Rt)(Rv)(Rw)(Yl), Compound 20-(Ei)(Rv)(Rw)(Yl), Compound 21-(Ei)(Rs)(Rt)(Rv)(Yl), Compound 22-(Eh)(Ek)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 23-(Ei)(Ej)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 24-(Eh)(Ek)(Rv)(Rw)(Yl), Compound 25-(Ei)(Ej) (Rv)(Rw)(Yl), Compound 26-(Ei)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 27-(Ei)(Rv)(Rw)(Yl)(Ym) (Yo)(Yp), compound 28-(Ei)(Rv)(Rw)(Yl) and compound 29-(Ei)(Rv)(Rw)(Yl);

[0183] Each of Rs, Rt, Rv and Rw is independently selected from R1 to R146; each of Ei, Ej, Eh and Ek is independently selected from E1 to E171; and each of Yl, Ym, Yo and Yp is independently selected from Y1 to Y149, wherein Y1 to Y146 are defined as N-R1 to N-R146 respectively, Y147 is O, Y148 is S and Y149 is Se;

[0184] Each of compounds 1-(E1)(E1)(E1)(E1)(R1)(Y1)(Y1)(Y1)(Y1)(Y1) to 29-(E171)(R146)(R146)(Y149) is defined in the following list A5:

[0185]

[0186]

[0187]

[0188]

[0189] Each of E1 through E171 is defined in Listing A3 as defined herein; and

[0190] Each of R1 to R146 is defined in the following list A6:

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In some embodiments, the compound is selected from the group consisting of structures listed in A7 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0202] In some embodiments, the compound is partially or fully deuterated. In some embodiments, the compound is partially deuterated. In some embodiments, the compound is fully deuterated.

[0203] 2. The OLED and device disclosed herein

[0204] On the other hand, an organic light-emitting device (OLED) is provided, the OLED comprising an anode, a cathode, and an emitting region disposed between the anode and the cathode, wherein the emitting region contains a component of formula I. Compounds with the structure of Y. In formula I: Y A Y B Y C and YD Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR';

[0205] R A R B and R C Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution;

[0206] Each R, R', R 1 R 2 R 3 R 4 R A R B and R C Substituents that are independently hydrogen or selected from the group of universal substituents as defined herein;

[0207] R 1 R 2 R 3 Or R 4 At least one of them is an electron-withdrawing group; and

[0208] Any two substituents can join or fuse to form a ring.

[0209] In some embodiments, the compound is not: , or .

[0210] In some embodiments, the compound comprising the structure of Formula I is a fluorescent emitter.

[0211] In some embodiments, the emission region does not contain a metal complex.

[0212] In some embodiments, the emission region further includes a first body. In some embodiments, the emission region comprises a compound comprising a structure of Formula I and a first body. In some embodiments, the emission region further includes a second body.

[0213] In some embodiments, the first body comprises at least one anthracene.

[0214] In some embodiments, the S1 energy (first singlet state energy) of the first host is higher than that of any compound of Formula I as defined herein. In some embodiments, the T1 energy (first triplet state energy) of the first host is lower than that of any compound of Formula I as defined herein.

[0215] In some embodiments, the first body is capable of generating P-type delayed fluorescence.

[0216] In some embodiments, the first body is fully or partially deuterated.

[0217] In some embodiments, the first body consists of an aromatic hydrocarbon ring. In other words, in some embodiments, the first body does not include any heterocycles.

[0218] In some embodiments, the second body is fully or partially deuterated.

[0219] In some embodiments, the second body is composed of an aromatic hydrocarbon ring.

[0220] In some embodiments, the LUMO level of the first host is lower than the LUMO of any compound of Formula I as defined herein.

[0221] In some embodiments, the HOMO level of the first host is lower than that of any compound of Formula I as defined herein.

[0222] In some embodiments, the first host and the second host can form an excitocomplex.

[0223] In some embodiments, a compound comprising Formula I as defined herein is a receptor (A1).

[0224] In some embodiments, the emission region further comprises compound S1, wherein the compound comprising the structure of Formula I is a receptor (A1), and compound S1 is a sensitizer capable of transferring energy from at least one of its excited states to an excited state of receptor A1 at room temperature.

[0225] In some embodiments, compound S1 is one of the components of the excimer complex. In some embodiments, the excimer complex is formed of two or more materials, comprising an organometallic complex and a host. In some embodiments, the organometallic complex comprises a phosphorescent material, a fluorescent material, or a thermally activated delayed fluorescence material. In some embodiments, the host comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2-Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-borona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacrylidine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo and aza-(5,9-dioxa-13b-borona[3,2,1-de]anthracene).

[0226] In some embodiments, the host may be an e-host or an h-host. In some embodiments, the host may comprise an electron donor material containing a component having hole transport characteristics and containing at least one of carbazole, arylamino, silyl, fluorenyl, spirofluorenyl, dibenzothiophene, and dibenzofuranylaryl, phosphonoyloxy, and TP groups. In some embodiments, the host may comprise an electron acceptor material containing a component having electron transport characteristics and containing at least one of boraneyl, pyridinyl, pyrimidinyl, triazine, imidazole, phenanthroline, sulfone, heptaazinyl, oxadiazolyl, cyano, and diphenyl groups.

[0227] In some embodiments, S1 and A1 are not covalently connected.

[0228] In some embodiments, S1 and A1 are covalently linked by a direct bond or an organic linker group L1.

[0229] In some embodiments, S1 and A1 are covalently connected by a direct bond.

[0230] In some embodiments, S1 and A1 are covalently linked by an organic linker group L1, which comprises a structure selected from the group consisting of structures listed in List 1 below: , , , , , , , , , , , and ,in:

[0231] n is an integer from 1 to 10;

[0232] Y A and Y B Each of them is independently selected from the following groups: BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR', and GeRR';

[0233] R LA R LB R LC and R LD Each of these terms independently represents a single substitution up to the maximum possible number of substitutions or no substitutions;

[0234] Each R, R', R LA R LB R LC and R LD Substituents that are independently hydrogen or selected from the group of universal substituents as defined herein;

[0235] R L1 and R L2 Each is independently selected from the group consisting of: alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, boroalkyl, their deuterated variants and combinations thereof; and

[0236] R, R', R L1 R L2 R LA R LB R LC and R LD Two adjacent elements may be joined or fused to form a ring.

[0237] In some embodiments, the sensitizer S1 and the receptor A1 are covalently linked by an organic linker group L1, the organic linker group L1 comprising a structure selected from the group consisting of structures listed in List 2 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and its variants that are fully or partially deuterated; where n is an integer from 1 to 10.

[0238] In some embodiments, compound S1 is capable of transferring energy from its excited state manifold to the excited state manifold of compound A1.

[0239] In some embodiments, compound A1 has an emission peak of less than 540 nm. In some embodiments, compound A1 has an emission peak of less than 535 nm, or less than 530 nm, or less than 525 nm. In some such embodiments, the emission peak is measured in 1% PMMA.

[0240] In some embodiments, compound A1 has an emission peak of at least 500 nm. In some embodiments, compound A1 has an emission peak of at least 510 nm, or at least 515 nm, or at least 520 nm.

[0241] In some embodiments, compound S1 has an emission peak of 400 nm to 480 nm.

[0242] In some embodiments, compound S1 has an emission peak of 480 nm to 800 nm.

[0243] In some embodiments, sensitizer S1 has an emission peak value of 400 nm to 420 nm. In some embodiments, sensitizer S1 has an emission peak value of 420 nm to 440 nm. In some embodiments, sensitizer S1 has an emission peak value of 440 nm to 470 nm. In some embodiments, sensitizer S1 has an emission peak value of 470 nm to 500 nm. In some embodiments, sensitizer S1 has an emission peak value of 500 nm to 550 nm. In some embodiments, sensitizer S1 has an emission peak value of 600 nm to 670 nm. In some embodiments, sensitizer S1 has an emission peak value of 670 nm to 800 nm.

[0244] In some embodiments, compound A1 has a Stokes shift of less than 100 nm. In some embodiments, compound A1 has a Stokes shift of less than 80 nm. In some embodiments, compound A1 has a Stokes shift of less than 60 nm. In some embodiments, compound A1 has a Stokes shift of less than 40 nm.

[0245] In some embodiments, the spectral overlap integral of compound A1 and compound S1 is at least As used herein, the “spectral overlap integral” has its standard meaning and can be determined by multiplying the extinction spectrum of acceptor A1 by the emission spectrum of sensitizer S1 normalized relative to the area under the curve. Higher spectral overlap results in better FRET efficiency. The Forster Resonance Energy Transfer (FRET) rate is proportional to the spectral overlap integral; therefore, high spectral overlap is desirable to improve FRET efficiency and shorten exciton lifetime in the device. Increasing spectral overlap can be achieved in several ways, such as increasing the oscillator strength of acceptor A1, minimizing the distance between the emission peak of sensitizer S1 and the absorption peak of acceptor A1, and narrowing the linearity of either sensitizer S1 emission or acceptor A1 absorption.

[0246] In some embodiments, the spectral overlap integral of compound A1 and compound S1 is at least In some embodiments, the spectral overlap integral of compound A1 and compound S1 is at least... .

[0247] In some embodiments, compound S1 is a phosphorescent material, a fluorescent material, or a thermally activated delayed fluorescence material.

[0248] In some embodiments, compound S1 is a phosphorescent material.

[0249] In some embodiments, compound S1 is an organometallic complex. In some embodiments, compound S1 is an organometallic Ir complex. In some embodiments, compound S1 is an organometallic Pt complex. In some embodiments, compound S1 is an organometallic Pd complex. In some embodiments, compound S1 is an organometallic Cu complex, Ag complex, or Au complex.

[0250] In some embodiments, compound S1 has the formula M(L) 1 ) x (L 2 ) y (L 3 ) z ;

[0251] Where L1 L 2 and L 3 They can be the same or different;

[0252] Where x is 1, 2, or 3;

[0253] Where y is 0, 1, or 2;

[0254] Where z is 0, 1, or 2;

[0255] Metal M is selected from the following group: Ir, Pt, Pd, Au, Ag, and Cu;

[0256] Where x+y+z is the oxidation state of the metal M;

[0257] Where L 1 Select from groups consisting of structures in the ligand list as defined in this paper;

[0258] Where L 2 and L 3 Independent freedom of choice The group consisting of the structures of the ligand list defined in this article;

[0259] in:

[0260] T can be freely selected from the following groups: B, Al, Ga, and In;

[0261] K 1' It is a direct key or a selection of the following groups: NR e PR e , O, S and Se;

[0262] Each Y 1 To Y 13 Independently select groups composed of free carbon and nitrogen;

[0263] Y' selects from the following groups: 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 ;

[0264] R e and R f They can be fused or joined to form rings;

[0265] Each R a R b Rc and R d It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0266] Each R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Substituents that are independently hydrogen or selected from the group of substituents as defined herein; and

[0267] R a1 R b1 R c1 R d1 R a R b R c and R d Any two of them can fused or joined to form a ring or a polydentate ligand.

[0268] In some embodiments, metal M is Ir, Pt, or Pd. In some embodiments, metal M is Ir. In some embodiments, metal M is Pt. In some embodiments, metal M is Pd.

[0269] In some embodiments, the sensitizer S1 has a formula selected from the group consisting of the structures listed in List 3 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , and ;

[0270] in:

[0271] X 96 To X 99 Each of them is independently C or N;

[0272] Y 100 and Y 200 Each of them is independently selected from the group consisting of NR, O, S, and Se;

[0273] L is independently selected from the following groups: direct bond, BR, BRR', NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof;

[0274] X 100 Each time it appears, select from the following groups: O, S, Se, NR", and CRR';

[0275] Each R 10a R 20a R 30a R 40a R 50a R A" R B" R C" R D" R E" and R F" Independently represents monosubstituted, at most maximum substituted, or unsubstituted;

[0276] Each R, R', R 10a R 11a R 12a R 13a R 20a R 30a R 40a R 50a R 60 R 70 R 97 R98 R 99 R A1' R A2' R A" R B" R C" R D" R E" R F" R G" R H" R I" R J" R K" R L" R M" and R N" Independently, it is hydrogen or a substituent selected from the group of universal substituents as defined herein; and

[0277] Any two substituents can join or fused to form a ring.

[0278] It should be understood that for each of the compounds containing Pt, the Pt atom can be replaced by a Pd atom, and it is also intended to specifically cover those Pd derivatives.

[0279] In some embodiments, L 2 Choose freely L Bk A group consisting of k, where k is an integer from 1 to 544, and L B1 To L B544 Each of them has the structure defined in Listing 4 below:

[0280] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , and .

[0281] In some embodiments, the sensitizer S1 has a formula selected from the group consisting of structures listed in List 5: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0282] In some embodiments, compound S1 is a fluorescent material.

[0283] In some embodiments, S1 is a delayed fluorescence compound that acts as a thermally activated delayed fluorescence (TADF) material in an OLED at room temperature.

[0284] In some embodiments, the TADF material comprises at least one donor group and at least one acceptor group.

[0285] In some embodiments, the TADF material is a metal complex. In some embodiments, the TADF material is a Cu, Ag, or Au complex.

[0286] In some embodiments, the TADF material is a nonmetallic complex.

[0287] In some embodiments, TADF materials have the formula M(L 5 (L) 6 );

[0288] Where M is Cu, Ag, or Au;

[0289] Where L 5 and L 6 They are different, and

[0290] Where L 5 and L 6 Each of the following groups is independently selected from the structures listed in List 6: , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0291] Where A 1 To A 9 Each of them is independently selected from C or N;

[0292] R P R Q R T and R U Each of these terms independently represents monosubstituted, at most maximum substituted, or unsubstituted.

[0293] Each R P R Q R T R U R SA R SB R RA R RB R RC R RD R RE and R RF Independently, it is hydrogen or a substituent selected from the group of universal substituents as defined herein; and

[0294] Any two substituents can join or fused to form a ring.

[0295] In some embodiments, the TADF material is selected from the group consisting of the structures defined in List 7 below: , , , , , , , , , , , , , , , , , , , , , , , and .

[0296] In some embodiments, the TADF material comprises at least one chemical group selected from the group consisting of structures defined in List 8 below: , , , , , , , , , , , , , , , , , , , , and ;

[0297] Where Y T Y U Y V and Y W Each of them is independently selected from the following groups: BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR', and GeRR';

[0298] Each R T They can be the same or different, and each R T Independently, it is a donor group, an acceptor group, an organic linking group bonded to a donor group, an organic linking group bonded to an acceptor group, or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, aryl, heteroaryl, and combinations thereof; and

[0299] R and R' are each independently hydrogen or a substituent selected from the group of universal substituents as defined herein.

[0300] In some embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a maximum of three carbon ring atoms in total, together with their substituents, may be replaced by N.

[0301] In some embodiments, the TADF material comprises at least one chemical group selected from the group consisting of: nitrile, isonitrile, borane, fluorine, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole.

[0302] In some embodiments, the emission region comprises a single emission layer.

[0303] In some embodiments, the emission region comprises two or more emission layers. In some embodiments, each of the two or more emission layers is directly stacked on top of the other. In some embodiments, each of the two or more emission layers is separated by a charge-generating layer.

[0304] In some embodiments, the emission region comprises at least one body material.

[0305] In some embodiments, compound S1 and compound A1 are present together in at least one emission layer.

[0306] In some embodiments, compound S1 and compound A1 are in different emission layers. In some embodiments, receptor A1 and sensitizer S1 are not present in any of the same emission layers. In some embodiments, the emission layer containing compound S1 is in contact with the emission layer containing compound A1. In some embodiments, the emission layer containing compound S1 is not in contact with the emission layer containing compound A1.

[0307] In some embodiments, the emission region comprises at least one emission layer, and the concentration of compound A1 in each of the at least one emission layer containing compound A1 is at least >2 vol-%. In some embodiments, the emission region comprises at least one emission layer, and the concentration of compound A1 in each of the at least one emission layer containing compound A1 is at least >3 vol-%. In some embodiments, the emission region comprises at least one emission layer, and the concentration of compound A1 in each of the at least one emission layer containing compound A1 is at least >4 vol-%. In some embodiments, the emission region comprises at least one emission layer, and the concentration of compound A1 in each of the at least one emission layer containing compound A1 is at least >5 vol-%.

[0308] In some embodiments, k FRET >k NR,S1 , where k FRET It is the average Foster resonance energy transfer rate between the sensitizer S1 and the acceptor A1 in the emission region, and k NR,S1 It is the nonradiative velocity of a PMMA thin film doped with 1% by weight of sensitizer S1. In some embodiments, k FRET k NR,S1 and k DEX It can be measured using transient phosphorescence (PL) and transient absorption measurements known in the art.

[0309] In some embodiments, k DEX >k NR,S1 , where k DEX It is the average Dexter energy transfer rate between sensitizer S1 and receptor A1.

[0310] In some embodiments, receptor A1 produces at least 50% of the emission in the emission region. In some embodiments, this is determined by measuring the emission spectrum of each emitter separately and then expressing the emission region spectrum as a linear sum of the individual emission spectra. Therefore, the percentage of emission produced by compound A1 (or another compound in the emission region) can be measured by measuring the emission spectrum of compound A1 (or another compound) in the emission region separately, and then the percentage of emission produced by compound A1 (or another compound in the emission region) can be expressed as a linear sum of the individual emission spectra in the emission region.

[0311] In some embodiments, compound A1 produces at least 70% emission in the emission region. In some embodiments, compound A1 produces at least 80% emission in the emission region. In some embodiments, compound A1 produces at least 90% emission in the emission region.

[0312] In some embodiments, the full width at half maximum (FWHM) of the emission region is at least 5 nm smaller than the FWHM of compound S1 alone. In some embodiments, the FWHM of the emission region is at least 10 nm smaller than the FWHM of compound S1 alone. In some embodiments, the FWHM of the emission region is at least 15 nm smaller than the FWHM of compound S1 alone. In some embodiments, the FWHM of the emission region is at least 20 nm smaller than the FWHM of compound S1 alone.

[0313] In some embodiments, the M / T ratio of the emission region is at least 0.02 less than the M / T ratio of the sensitizer S1. In some embodiments, the M / T ratio of the emission region is at least 0.035 less than the M / T ratio of the compound S1. In some embodiments, the M / T ratio of the emission region is at least 0.05 less than the M / T ratio of the compound S1.

[0314] As used in this article, the M / T ratio is a parameter describing the "narrowness" of a peak. M is the area of ​​the main peak, which is defined as the wavelength of the maximum peak (λ). max The integral of the area over ±15 nm. T is the total area of ​​the spectrum, defined as the integral over the entire spectrum. A high M / T indicates that the dopant has a narrow line shape.

[0315] In some embodiments, compound A1 is selected from the group consisting of structures as defined herein in List A4. In some embodiments, compound A1 is selected from the group consisting of structures as defined herein in List A5.

[0316] In some embodiments, the emission region further includes a third compound. In some embodiments, the third compound is the host. In some embodiments, the third compound is an H-host.

[0317] In some embodiments, the emission region further includes a fourth compound. In some embodiments, the fourth compound is the host. In some embodiments, the fourth compound is an E-host.

[0318] In some embodiments, the first, second, third, or fourth host compound comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-borona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacrylidine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo and aza-(5,9-dioxa-13b-borona[3,2,1-de]anthracene).

[0319] In some embodiments, the third compound is selected from the group consisting of structures of subject group 1 as defined herein:

[0320] in:

[0321] Each of J1 to J6 is independently either C or N;

[0322] L' is a direct bond or an organic linking group;

[0323] Each Y AA Y BB Y CC and Y DD Independently select from the following groups: non-existent bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0324] R A' R B' R C' R D' R E' R F' and R G' Each of these terms independently represents monosubstituted, at most maximum substituted, or unsubstituted.

[0325] Each R, R', R A' R B' RC' R D' R E' R F' and R G' Independently, it is hydrogen or a substituent selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring; and

[0326] Where possible, each unsubstituted aromatic carbon atom is optionally replaced by one or more N atoms to form a nitrogen-substituted ring.

[0327] In some embodiments of main group 1, L' is an organic linking group selected from the group consisting of: BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof.

[0328] In some embodiments, the emission region further includes a fourth compound capable of emitting fluorescence or delayed fluorescence. In some embodiments, the fourth compound comprises a group selected from List 9 as defined herein.

[0329] In some embodiments, the OLED further includes at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, an electron blocking layer, an emissive material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer.

[0330] In some embodiments, a consumer product comprising an OLED as described herein is provided. In some embodiments, the consumer product is selected from the group consisting of: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external lighting and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (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 comprising multiple displays tiled together, theater or stadium screens, phototherapy devices, and signs.

[0331] In some embodiments, the OLED of this disclosure includes an emitting region disposed between an anode and a cathode; wherein the emitting region includes a sensitizer compound and an acceptor compound (e.g., a compound comprising a structure of formula I); wherein the sensitizer transfers energy to the acceptor compound, which acts as an emitter. In some embodiments, the sensitizer compound is capable of emitting light from a triplet excited state to a ground singlet state in the OLED at room temperature. In some embodiments, the sensitizer compound is capable of acting as a phosphorescent emitter, a TADF emitter, or a dual-state emitter in the OLED at room temperature; these are also referred to as phosphorescent materials, TADF materials, or dual-state materials. In some embodiments, the acceptor compound is selected from the group consisting of: delayed fluorescence compounds that act as TADF emitters in the OLED at room temperature, i.e., delayed fluorescence materials; and fluorescent compounds that act as fluorescent emitters in the OLED at room temperature, i.e., fluorescent materials. In some embodiments, the fluorescent emitter may be a singlet or dual-state emitter. In some such embodiments, the singlet emitter may further include a TADF emitter, and further include a multi-resonance MR-TADF emitter. The description of delayed fluorescence used herein can be found in paragraphs 0083-0084 of U.S. Patent Application Publication US20200373510A1, the entire contents of which are incorporated herein by reference.

[0332] In some embodiments of OLEDs, the sensitizer and acceptor compounds are located in separate layers within the emission region.

[0333] In some embodiments, the sensitizer and acceptor compound are present as a mixture in one or more layers of the emission region. It should be understood that the mixture in a given layer can be a homogeneous mixture, or the compounds in the mixture can exhibit a gradient concentration over the thickness of a given layer. The concentration gradient can be linear, non-linear, sinusoidal, etc. When more than one layer containing a mixture of sensitizer and acceptor compound exists in the emission region, the type of mixture (i.e., homogeneous or gradient concentration) and the concentration levels of the compounds in the mixture in each of the more than one layer can be the same or different. In addition to the sensitizer and acceptor compound, one or more other functional compounds, such as, but not limited to, the host compound, may also be mixed into the mixture.

[0334] In some embodiments, the receptor compound may be located in two or more layers having the same or different concentrations. In some embodiments, when two or more layers contain the receptor compound, the concentrations of the receptor compound in at least two of the two or more layers are different. In some embodiments, the concentration of the sensitizer compound in the layer containing the sensitizer compound is in the range of 1 to 50 wt%, 10 to 20 wt%, or 12 to 15 wt%. In some embodiments, the concentration of the receptor compound in the layer containing the receptor compound is in the range of 0.1 to 10 wt%, 0.5 to 5 wt%, or 1 to 3 wt%.

[0335] In some embodiments, the emission region comprises N layers, where N > 2. In some embodiments, a sensitizer compound is present in each of the N layers, and a receptor compound is contained in fewer than or equal to N-1 layers. In some embodiments, a sensitizer compound is present in each of the N layers, and a receptor compound is contained in fewer than or equal to N / 2 layers. In some embodiments, a receptor compound is present in each of the N layers, and a sensitizer compound is contained in fewer than or equal to N-1 layers. In some embodiments, a receptor compound is present in each of the N layers, and a sensitizer compound is contained in fewer than or equal to N / 2 layers.

[0336] In some embodiments, when a voltage is applied across the OLED, the OLED emits light, which includes an emission component of the S1 energy (first singlet state energy) from the acceptor compound. In some embodiments, at least 65%, 75%, 85%, or 95% of the OLED's emission is generated by the acceptor compound at a rate of at least 10 cd / m². 2 The brightness is generated. In some embodiments, the S1 energy of the receptor compound is lower than that of the sensitizer compound.

[0337] In some embodiments, the T1 energy (first triplet energy) of the host compound is greater than or equal to the T1 energies of the sensitizer compound and the acceptor compound, and the T1 energy of the sensitizer compound is greater than or equal to the S1 energy (first singlet energy) of the acceptor compound. In some embodiments, the S1-T1 bandgap of the sensitizer compound and / or the acceptor compound and / or the first host compound and / or the second host compound is less than 400, 300, 250, 200, 150, 100, or 50 meV. In some embodiments, the absolute energy difference between the HOMO of the sensitizer compound and the HOMO of the acceptor compound is less than 0.6, 0.5, 0.4, 0.3, or 0.2 eV. In some embodiments, the absolute energy difference between the LUMO of the sensitizer compound and the LUMO of the acceptor compound is less than 0.6, 0.5, 0.4, 0.3, or 0.2 eV.

[0338] Typically, T1 energy, HOMO, and LUMO can be obtained experimentally, and unless otherwise explicitly stated, these measurements (figures) will be used for the relevant purposes, intentions, and / or embodiments. More specifically, solution cyclic voltammetry and differential pulse voltammetry can be performed using a CH instrument model 6201B potentiostat, using anhydrous dimethylformamide solvent and tetrabutylammonium hexafluorophosphate as the supporting electrolyte. Glassy carbon, platinum wire, and silver wire can be used as the working electrode, counter electrode, and reference electrode, respectively. The electrochemical potential is referenced to the internal ferrocene-ferrocene redox pair (Fc / Fc+) by measuring the peak potential difference using differential pulse voltammetry. According to the literature ((a) Fink, R.; Heischkel, Y.; Thelakkat, M.; Schmidt, H.-W.), Chem. Mater. 1998, 10, 3620-3625; (b) Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, RF; Bassler, H.; Porsch, M.; Daub, Journal of Advanced Materials 1995, 7, 551), the redox potentials of the cations and anions can then be compared with those of the ferrocene reference (4.8). The corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were determined by measuring the energy of the HOMO (highest occupied molecular orbital) relative to vacuum (eV).

[0339] The T1 energy can be obtained from the emission spectrum of the frozen sample in 2-MeTHF at 77 K.

[0340] Emission spectra were collected using a Horiba Fluorolog-3 spectrophotometer equipped with a Synapse Plus CCD detector. All samples were excited at 340 nm. Transient data were measured in the Fluorolog-3 by time-correlated single-photon counting (TCSPC) using a 335 nm NanoLED pulsed excitation source. PLQY values ​​were measured using a Hamamatsu Quantaurus-QY Plus UV-NIR absolute PL quantum yield spectrometer with an excitation wavelength of 340 nm. A solution of 1% emitter and PMMA in toluene was prepared, filtered, and dropwise cast onto a quartz substrate.

[0341] In some embodiments where the sensitizer compound provides monochromatic sensitization (i.e., minimal energy loss after energy transfer to the acceptor compound), the acceptor compound has a Stokes shift of 30, 25, 20, 15, or 10 nm or less. An example is a broad blue phosphor sensitive to a narrow blue light emission acceptor.

[0342] In some embodiments where the sensitizer compound provides the downconversion process (e.g., for sensitizing a blue emitter for a green emitter, or for sensitizing a green emitter for a red emitter), the acceptor compound has a Stokes shift of 30, 40, 60, 80, or 100 nm or greater.

[0343] In some embodiments, the difference between the λmax of the emission spectrum of compound S1 and the λmax of the absorption spectrum of compound A1 is 50, 40, 30, or 20 nm or less. In some embodiments, the difference between the λmax of the emission spectrum of the highest energy emission peak of compound S1 and the λmax of the absorption spectrum of the lowest energy absorption peak of compound A1 is 50, 40, 30, or 20 nm or less. In some embodiments, the spectral overlap area between the absorption spectrum of compound A1 normalized to the lowest energy absorption peak and the emission spectrum of compound S1 normalized to the highest energy emission peak is greater than 5%, 10%, 15%, 20%, 30%, 40%, 50%, or greater, relative to the area of ​​the emission spectrum of compound S1 normalized to the highest energy emission peak.

[0344] A qualitative relationship between a quantitative sensitizer compound (a compound intended to be used as a sensitizer in the OLED emission region of this disclosure) and an acceptor compound (a compound intended to be used as a acceptor in the OLED emission region of this disclosure) is determined by measuring the value Δλ = λ. max1 - λ max2 , where λ max1 and λ max2 The definition is as follows. λ max1 λ is the maximum emission value of the sensitizer compound at room temperature when it is used as the sole emitter in a first monochromatic OLED (an OLED that emits only one color) having a first host. max2 This is the maximum emission value of the acceptor compound at room temperature when it is used as the sole emitter in a second monochromatic OLED having the same first host.

[0345] In some embodiments of the OLED of this disclosure where the sensitizer compound provides monochromatic sensitization (i.e., minimal energy loss after energy transfer to the acceptor compound), Δλ (as determined above) is equal to or less than a number selected from the group consisting of: 15, 12, 10, 8, 6, 4, 2, 0, -2, -4, -6, -8, and -10 nm.

[0346] In some embodiments, the spectral overlap integral of the receptor compound and the sensitizer compound is at least In some embodiments, the spectral overlap integral of the receptor compound and the sensitizer compound is at least In some embodiments, the spectral overlap integral of the receptor compound and the sensitizer compound is at least .

[0347] As used in this paper, the “spectral overlap integral” is determined by multiplying the extinction spectrum of the acceptor compound by the emission spectrum of the sensitizer compound normalized relative to the area under the curve. Higher spectral overlap results in better Förster resonance energy transfer (FRET) efficiency. The FRET ratio is proportional to the spectral overlap integral. Therefore, high spectral overlap can contribute to improved FRET efficiency and a shorter exciton lifetime in OLEDs.

[0348] In some embodiments, the acceptor compound and the sensitizer compound are selected to increase spectral overlap. Increasing spectral overlap can be achieved in several ways, such as increasing the oscillator intensity of the acceptor compound, minimizing the distance between the emission intensity of the sensitizer compound peak and the absorption peak of the acceptor compound, and narrowing the linearity of the emission of the sensitizer compound or the absorption of the acceptor compound. In some embodiments, the oscillator intensity of the acceptor compound is greater than or equal to 0.1.

[0349] In some embodiments of receptor emission via sensitized redshift, the absolute value of Δλ is equal to or greater than the value selected from the group consisting of 20, 30, 40, 60, 80, and 100 nm.

[0350] In these embodiments, the sensitizer compound is a phosphorescent material, and the sensitizer compound may be a metal coordination complex having a metal-carbon bond, a metal-nitrogen bond, or a metal-oxygen bond. In some embodiments, the metal is selected from the group consisting of: Ir, Rh, Re, Ru, Os, Pt, Pd, Zn, Zr, Au, Ag, and Cu. In some embodiments, the metal is Ir. In some embodiments, the metal is Pt. In some embodiments, the sensitizer compound has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ;

[0351] Where L 1 L 2 and L 3 They can be the same or different;

[0352] Where x is 1, 2, or 3;

[0353] Where y is 0, 1, or 2;

[0354] Where z is 0, 1, or 2;

[0355] Where x+y+z is the oxidation state of the metal M;

[0356] Where L 1 Select the group consisting of structures from the following list of ligands:

[0357] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0358] Where L 2 and L 3 Independently select groups of structures from the list of free and ligands. ;in:

[0359] T can be freely selected from the following groups: B, Al, Ga, and In;

[0360] K 1' It is a direct key or a selection of the following groups: NR e PR e , O, S and Se;

[0361] Each Y 1 To Y 13 Independently select groups composed of free carbon and nitrogen;

[0362] Y' selects from the following groups: 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 ;

[0363] R e and R f They can be fused or joined to form rings;

[0364] Each R a R b R c and R d It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0365] Each R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Independently, it is hydrogen or a substituent selected from the group of universal substituents as defined herein; and

[0366] Where R a1 R b1 R c1 R d1 R a R b R c and R d Any two of them can fused or joined to form a ring or a polydentate ligand.

[0367] In some embodiments, the formula M(L) 1 ) x (L 2 ) y (L 3 ) z The metals in the sample are selected from the group consisting of Cu, Ag, or Au.

[0368] In some embodiments of OLEDs, the sensitizer compound has a formula selected from the group consisting of: Ir(L A 3. Ir(L) A (L) B )2、Ir(LA )2(L B ), Ir(L A )2(L C ), Ir(L A (L) B (L) C ) and Pt(L A (L) B );

[0369] Where L A L B and L C They differ from each other in Ir compounds;

[0370] Where L A and L B In Pt compounds, they can be the same or different; and

[0371] Where L A and L B They can be linked to form tetradentate ligands in the Pt compound.

[0372] In some embodiments of the OLED, the sensitizer compound is selected from the group consisting of compounds in the following sensitizer list:

[0373] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , and ;

[0374] X 96 To X 99 Each of them is independently C or N;

[0375] Each Y 100 Independently select the groups composed of NR", O", S and Se;

[0376] L is independently selected from the following groups: direct bond, BR", BR"R"', NR", PR", O, S, Se, C=O, C=S, C=Se, C=NR", C=CR"R"', S=O, SO2, CR", CR"R"', SiR"R"', GeR"R"', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof;

[0377] X 100 and X 200 Each time it appears, select from the following groups: O, S, Se, NR" and CR"R"';

[0378] Each R 10a R 20a R 30a R 40a and R 50a R A" R B" R C" R D" R E" and R F" Independently represents monosubstituted, at most maximum substituted, or unsubstituted;

[0379] R, R', R", R"', R 10a R 11aR 12a R 13a R 20a R 30a R 40a R 50a R 60 R 70 R 97 R 98 R 99 R A1' R A2' R A" R B" R C" R D" R E" R F" R G" R H" R I" R J" R K" R L" R M" and R N" Each of them is independently hydrogen or a substituent selected from the group of general substituents as defined herein; wherein any two substituents may be fused or joined to form a ring.

[0380] In some embodiments of OLEDs in which the sensitizer is selected from the group consisting of structures in the sensitizer list, R, R', R"", R"', R 10a R 11a R 12a R 13a R 20a R 30a R 40a R 50a R 60 R 70 R 97 R 98 R 99 R A1' R A2' R A" R B" R C" R D" R E" R F" R G" R H" R I" R J" R K" R L" R M" and R N"One or more of the groups comprised of groups selected from the group consisting of: fully or partially deuterated aryl, fully or partially deuterated alkyl, boronyl, silyl, germanyl, 2,6-triphenyl, 2-biphenyl, 2-(tert-butyl)phenyl, tetraphenylene, tetrahydronaphthalene, and combinations thereof.

[0381] In some embodiments, the sensitizer and / or acceptor can be a phosphorescent or fluorescent material / emitter. Phosphorescence generally refers to photon emission when the electron spin quantum number changes, that is, the initial and final states of emission have different electron spin quantum numbers, such as from the T1 to the S0 state. Most Ir and Pt complexes currently used in OLEDs are phosphorescent emitters. In some embodiments, such exciton complexes can also emit phosphorescence if the formation of the exciton complex involves a triplet emitter. On the other hand, a fluorescent emitter generally refers to photon emission without a change in the electron spin quantum number, such as from the S1 to the S0 state, or from the D1 to the D0 state. Fluorescent emitters can be delayed or non-delayed fluorescent emitters. Depending on the spin state, a fluorescent emitter can be a singlet emitter, a doublet emitter, or other multiplet emitters. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA). On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the thermal population between the triplet and singlet excited states. Thermal energy can activate the triplet state to transition back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). E-type delayed fluorescence characteristics can be seen in exciton complex systems or single compounds. Without being bound by theory, it is assumed that TADF requires a small singlet-triplet bandgap (ΔE) less than or equal to 400, 350, 300, 250, 200, 150, 100, or 50 meV. S-TA TADF emitter is a compound or excitokinetic complex of electron transport compounds (TADFs). There are two main types of TADF emitters: one called donor-acceptor TADF and the other called multi-resonant (MR) TADF. Typically, donor-acceptor single compounds are constructed by linking an electron donor group (such as an amino or carbazole derivative) and an electron acceptor group (such as an N-containing six-membered aromatic ring or a cyano-substituted aromatic ring). Donor-acceptor excitokinetic complexes can be formed between hole-transporting compounds and electron-transporting compounds. Examples of MR-TADFs include highly conjugated fused-ring systems. In some embodiments, MR-TADF materials contain boron, carbon, and nitrogen atoms. They may also contain other atoms, such as oxygen. In some embodiments, the reverse intersystem crossing time from T1 to S1 for delayed fluorescence emission at 293 K is less than or equal to 10 microseconds. In some embodiments, such a time can be greater than 10 microseconds and less than 100 microseconds.

[0382] In some embodiments of OLEDs, the sensitizer compound can act as a TADF material in the OLED at room temperature. In some embodiments, the acceptor compound is a delayed fluorescence material that acts as an emitter in the OLED at room temperature.

[0383] In some embodiments of OLEDs, the delayed fluorescence material comprises at least one donor group and at least one acceptor group. In some embodiments, the delayed fluorescence material is a metal complex. In some embodiments, the delayed fluorescence material is a non-metallic complex. In some embodiments, the delayed fluorescence material is a Pt, Pd, Zn, Cu, Ag, or Au complex (some of which are also referred to as metal-assisted (MA) TADF). In some embodiments, the metal-assisted delayed fluorescence material comprises a metal-carbamate bond. In some embodiments, the non-delayed fluorescence material or the delayed fluorescence material comprises at least one chemical group selected from the group consisting of: arylamine, aryloxy, arylthio, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazo, 5,9-dioxa-13b-boronazona[3,2,1-de]anthracene, 5λ 2 ,9λ 2 -diaza-13b-boronanaphene[2,3,4-de]anthracene, 5-oxa-9λ 2-aza-13b-boronazona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacridine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, borane, amino, silane, their aza variants and combinations thereof. In some embodiments, the non-delayed fluorescent material or the delayed fluorescent material comprises tri(aryl / heteroaryl)borane, wherein one or more pairs of substituents from the aryl / heteroaryl group are bonded to form a ring. In some embodiments, the fluorescent material comprises at least one chemical group selected from the group consisting of: naphthalene, anthracene, phenanthrene, fluorene, pyrene, β, perylene, and azulene.

[0384] In some embodiments of OLEDs, TADF materials have the formula M(L 5 (L) 6 ), where M is Cu, Ag, or Au, L 5 and L 6 Different, and L 5 and L 6 Choose independently from the following groups:

[0385] , , , ¸ , , , , , , , , , , , , , , , , , , , , , and ;

[0386] Where A 1 -A 9 Each is independently selected from C or N;

[0387] Each R P R Q and R U Independently represent monosubstituted, at most maximally substituted, or unsubstituted; where each RP R P R U R SA R SB R RA R RB R RC R RD R RE and R RF Substituents are independently hydrogen or selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring.

[0388] In some embodiments of OLEDs, the TADF material is selected from the group consisting of:

[0389] , , , , , , and ;

[0390] Each R A" R B" R C" R D" R E" and R F" It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution;

[0391] Each R", R"', R A1 R A" R B" R C" R D" R E" and R F" Independently, it is hydrogen or a substituent selected from the group of general substituents as defined herein; wherein any two substituents may fused or joined to form a ring.

[0392] L is independently selected from the group consisting of: direct bond, BR", BR"R"', NR", PR", O, S, Se, C=O, C=S, C=Se, C=NR", C=CR"R"', S=O, SO2, CR", CR"R"', SiR"R"', GeR"R"', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof;

[0393] L1 ' and L2 ' Each of them is a monodentate anion ligand.

[0394] Each of X1' and X2' is a halide; and

[0395] Any two of the substituents can fused or joined to form a ring.

[0396] In some embodiments of OLEDs, the TADF material is selected from the group consisting of:

[0397] , , , , , , , , , , , , , , , , , , , , , , , , and .

[0398] In some embodiments of the OLED, the TADF material comprises boron atoms. In some embodiments of the OLED, the TADF material comprises at least one donor group selected from the group consisting of:

[0399] , , , , , , , , , , , , , , , , , , , and ;

[0400] Where Y T Y U Y V and YW Each of the following groups is selected independently: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2.

[0401] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a total of up to three carbon ring atoms, together with their substituents, may be replaced by N.

[0402] In some embodiments, the TADF material comprises at least one acceptor group selected from the group consisting of: nitrile, isonitrile, borane, fluorine, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole. In some embodiments, the acceptor group and donor group as described herein may be directly linked, or linked via a conjugated linker or a non-conjugated linker group (such as sp3 carbon or silicon atoms).

[0403] In some embodiments, the acceptor is a fluorescent material. In some embodiments, the fluorescent compound contains at least one chemical group selected from the group consisting of:

[0404] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0405] Where Y F Y G Y H and Y I Each of the following groups is selected independently: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2;

[0406] Where X F and X G Each group is independently selected from the groups composed of C and N.

[0407] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a total of up to three carbon ring atoms, together with their substituents, may be replaced by N.

[0408] In some embodiments of the OLED, the fluorescent compound is selected from the group consisting of:

[0409] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0410] Where Y F1 To Y F4 Each was independently selected from O, S, and NR. F1 ;

[0411] Where R F1 and R 1S To R 9S Each independently represents a single substitution up to the maximum possible number of substitutions or no substitution; and

[0412] Where R F1 and R 1S To R 9S Each substituent is independently hydrogen or selected from the group of general substituents as defined herein, and any two substituents may join or fuse to form a ring.

[0413] In some embodiments, the receptor compound comprises at least one group selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0414] Q '1 To Q '18 Each of them is independently C or N; and Y Q1 and Y Q2 Each of them is independently selected from the following groups: B, C, Si, Ge, N, P, O, S, Se, C=O, S=O, and SO2.

[0415] In some embodiments, the receptor compound comprises at least one group selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

[0416] In some embodiments, the receptor compound comprises at least one group selected from the group consisting of: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , and .

[0417] In some embodiments, the receptor compound is selected from the group consisting of structures in the following receptor list:

[0418] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 . 、 、 、 、 、 、 、 、 、 , Its nitrogen-substituted variants, its fully or partially deuterated variants, and combinations thereof.

[0419] In some of the above embodiments, any carbon ring atom in each benzene ring of any of the above structures, up to a total of up to three carbon ring atoms, together with their substituents, may be replaced by N.

[0420] In some embodiments, the acceptor compound comprises a fused ring system having at least five to fifteen 5-membered and / or 6-membered aromatic rings. In some embodiments, the acceptor compound has a first group and a second group, wherein the first group and the second group do not overlap; wherein at least 80% of the singlet excited state population of the lowest singlet excited state is located in the first group; and wherein at least 80%, 85%, 90%, or 95% of the triplet excited state population of the lowest triplet excited state is located in the second group.

[0421] In some embodiments, the emitter region further comprises a first body. In some embodiments, the sensitizer compound forms an exciton complex with the first body in the OLED at room temperature. In some embodiments, the LUMO energy of the first body is lower than the LUMO energy of the sensitizer compound and the acceptor compound in the emitter region. In some embodiments, the HOMO energy of the first body is lower than the HOMO energy of the sensitizer compound and the acceptor compound in the emitter region. In some embodiments, the HOMO energy of the first body is higher than the HOMO energy of the sensitizer compound and the acceptor compound in the emitter region. In some embodiments, the HOMO energy of the first body is higher than the HOMO energy of at least one of the sensitizer compound and the acceptor compound in the emitter region.

[0422] In some embodiments, the emitting region further includes a second body. In some embodiments, the first body forms an excimer complex with the second body in the OLED at room temperature. In some embodiments, the S1-T1 bandgap of the excimer complex formed by the first and second bodies is less than 0.4, 0.3, 0.2, or 0.1 eV. In some embodiments, the T1 energy of the excimer complex is greater than 2.5, 2.6, 2.7, or 2.8 eV. In some embodiments, the concentration of the first and second bodies in one or more layers containing the first and second bodies is greater than the concentration of the sensitizer compound and the acceptor compound in one or more layers containing the sensitizer compound and the acceptor compound. In some embodiments, the concentration of the first and second bodies in one or more layers containing the first and second bodies is greater than the concentration of the acceptor compound in one or more layers containing the sensitizer compound and the acceptor compound.

[0423] In some embodiments, the S1 energy of the first host is greater than the S1 energy of the acceptor compound. In some embodiments, the T1 energy of the first host is greater than the T1 energy of the sensitizer compound. In some embodiments, the HOMO energy of the sensitizer compound is greater than the HOMO energy of the acceptor compound. In some embodiments, the second host has a HOMO level that is shallower than the HOMO level of the acceptor compound. In some embodiments, the HOMO level of the acceptor compound is deeper than at least one selected from the sensitizer compound and the first host.

[0424] In some embodiments, the first body and / or the second body comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-borona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacrylidine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo[and]aza-(5,9-dioxa-13b-borona[3,2,1-de]anthracene). In some embodiments, both the first and second subjects are organic compounds.

[0425] In some embodiments, at least one of the first and second bodies is a metal complex.

[0426] In some embodiments, each of the first subject and / or the second subject is independently selected from the subject group 1 consisting of the following:

[0427] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ;

[0428] in:

[0429] Each of J1 to J6 is independently either C or N;

[0430] L' is a direct bond or an organic linking group;

[0431] Each Y AA Y BB Y CC and Y DD Independently select from the following groups: non-existent bond, direct bond, O, S, Se, CRR', SiRR', GeRR', NR, BR, BRR';

[0432] R A' R B' R C' R D' R E' R F' and R G' Each of these terms independently represents monosubstituted, at most maximum substituted, or unsubstituted.

[0433] Each R, R', R A' R B' R C' R D' R E' R F' and R G' Substituents are independently hydrogen or selected from the group of general substituents as defined herein; any two substituents may join or fuse to form a ring;

[0434] Furthermore, where possible, each unsubstituted aromatic carbon atom can be replaced by one or more N atoms to form a nitrogen-substituted ring.

[0435] In some embodiments, at least one of J1 to J3 is N. In some embodiments, at least two of J1 to J3 are N. In some embodiments, all three of J1 to J3 are N. In some embodiments, each Y CC and Y DD Preferably, it is O, S, and SiRR', more preferably O or S. In some embodiments, at least one unsubstituted aromatic carbon atom is replaced by N to form a nitrogen heterocycle.

[0436] In some embodiments, L' is an organic linking group selected from the group consisting of: BR, BRR', NR, PR, P(O)R, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof.

[0437] To reduce the amount of Dexter energy transfer between the sensitizer compound and the acceptor compound, a larger distance is preferably maintained between the centroid of the sensitizer compound and the centroid of the nearest acceptor compound in the emission region. Therefore, in some embodiments, the distance between the centroid of the acceptor compound and the centroid of the sensitizer compound is at least 2, 1.5, 1.0, or 0.75 nm.

[0438] Preferred acceptor / sensitizer VDR combination (A): In some embodiments, it is preferred that the acceptor VDR is less than 0.33 compared to the isotropic emitter, in order to reduce the coupling between the transition dipole moment of the emitter-acceptor and the plasma mode, thereby achieving higher decoupling efficiency. In some cases, when the acceptor VDR is less than 0.33, it is preferred that the sensitizer VDR is less than 0.33, in order to improve the coupling between the transition dipole moments of the sensitizer and the acceptor, thereby optimizing the Foster energy transfer rate. Therefore, in some embodiments of the OLED of the present invention, when the VDR is measured using an emission film test sample with an acceptor compound as the sole emitter, the acceptor compound in the OLED of the present invention exhibits a VDR value equal to or less than 0.33, 0.30, 0.25, 0.2, 0.15, 0.10, 0.08, or 0.05; and when the VDR is measured using an emission film test sample with a sensitizer compound as the sole emitter, the sensitizer compound in the OLED of the present invention exhibits a VDR value equal to or less than 0.33, 0.30, 0.25, 0.2, 0.15, 0.10, 0.08, or 0.05.

[0439] Preferred acceptor / sensitizer VDR combination (B): In some embodiments, it is preferred that the acceptor has a VDR of less than 0.33 compared to the isotropic emitter, in order to reduce the coupling between the transition dipole moment of the emitter-acceptor and the plasma mode, thereby achieving higher decoupling efficiency. In some cases, when the acceptor VDR is less than 0.33, it is preferred to minimize the intermolecular interactions between the sensitizer and the acceptor to reduce the degree of Dexter quenching. By modifying the molecular geometry of the sensitizer to reduce intermolecular interactions, it is preferable that the sensitizer has a VDR greater than 0.33. Therefore, in some embodiments of the OLED of the present invention, when the VDR is measured using an emission film test sample with an acceptor compound as the sole emitter, the acceptor compound in the OLED of the present invention exhibits a VDR value equal to or less than 0.33, 0.30, 0.25, 0.2, 0.15, 0.10, 0.08, or 0.05; and when the VDR is measured using an emission film test sample with a sensitizer compound as the sole emitter, the sensitizer compound in the OLED of the present invention exhibits a VDR value greater than 0.33, 0.4, 0.5, 0.6, or 0.7.

[0440] Preferred acceptor / sensitizer VDR combination (C): In some embodiments, it is preferred that the acceptor has a VDR greater than 0.33 compared to the isotropic emitter, in order to increase the coupling of the acceptor's transition dipole moment with the plasmonic mode, thereby reducing the transient lifetime of the excited state in the emitter layer. In some cases, increased coupling with the plasmonic mode can be combined with the enhancement layer in a plasmonic OLED device to improve efficiency and extend operating lifetime. In some cases, when the acceptor's VDR is greater than 0.33, it is preferred to minimize the intermolecular interactions between the sensitizer and the acceptor to reduce the degree of Dexter quenching. By modifying the molecular geometry of the sensitizer to reduce intermolecular interactions, it is preferable that the sensitizer has a VDR less than 0.33. Therefore, in some embodiments of the OLED of the present invention, when the VDR is measured using an emission film test sample with an acceptor compound as the sole emitter, the acceptor compound in the OLED of the present invention exhibits a VDR value greater than 0.33, 0.4, 0.5, 0.6, or 0.7; and when the VDR is measured using an emission film test sample with a sensitizer compound as the sole emitter, the sensitizer compound in the OLED of the present invention exhibits a VDR value equal to or less than 0.33, 0.30, 0.25, 0.2, 0.15, 0.10, 0.08, or 0.05.

[0441] Preferred acceptor / sensitizer VDR combination (D): In some embodiments, it is preferred that the acceptor has a VDR greater than 0.33 compared to the isotropic emitter, in order to increase the coupling of the acceptor's transition dipole moment with the plasmonic mode, thereby reducing the transient lifetime of the excited state in the emitter layer. In some cases, increased coupling with the plasmonic mode can be combined with the enhancement layer in a plasmonic OLED device to improve efficiency and extend operating lifetime. In some cases, when the acceptor's VDR is less than 0.33, it is preferred that the sensitizer's VDR is greater than 0.33, in order to improve the coupling of the sensitizer and acceptor's transition dipole moments, thereby optimizing the Foster energy transfer rate. Therefore, in some embodiments of the OLED of the present invention, when the VDR is measured using an emission film test sample with an acceptor compound as the sole emitter, the acceptor compound in the OLED of the present invention exhibits a VDR value greater than 0.33, 0.4, 0.5, 0.6 or 0.7; and when the VDR is measured using an emission film test sample with a sensitizer compound as the sole emitter, the sensitizer compound in the OLED of the present invention exhibits a VDR value greater than 0.33, 0.4, 0.5, 0.6 or 0.7.

[0442] VDR (Vertical Dipole Ratio) is the overall average fraction of vertically oriented molecular dipoles of the luminescent compound in the emitting thin film sample, where "vertical" orientation is relative to the plane of the substrate surface on which the thin film sample is formed (i.e., perpendicular to the substrate surface plane). A similar concept is the horizontal dipole ratio (HDR), which is the overall average fraction of horizontally oriented molecular dipoles of the luminescent compound in the emitting thin film sample, where "horizontal" orientation is relative to the plane of the substrate surface on which the thin film sample is formed (i.e., parallel to the substrate surface plane). By definition, VDR + HDR = 1. VDR can be measured using angle-dependent and polarization-dependent photoluminescence measurements. The VDR of the emitting layer of a thin film test sample can be determined by comparing the measured emission modes of a photoexcited thin film test sample with polarization-dependent modes modeled by a computer. For example, Figure 3 Modeled data for p-polarized emission is presented. Modeled p-polarized photoluminescence (PL) of emitters with different VDRs is plotted. The modeled PL peak is observed around a 45-degree angle, where the peak PL is larger when the emitter's VDR is higher.

[0443] To measure the VDR value of a thin film test sample, an acceptor compound or a sensitizer compound (depending on whether the VDR of the acceptor compound or sensitizer compound is being measured) can be used as the sole emitter in the thin film, and a reference host compound A can be used as the host to form the thin film test sample. Preferably, the reference host compound A is... Thin-film test samples are formed by thermally evaporating an emitter compound and a host compound on a substrate. For example, the emitter compound and host compound can be co-evaporated. In some embodiments, the doping level of the emitter compound in the host can be from 0.1 wt.% to 50 wt.%. In some embodiments, for a blue emitter, the doping level of the emitter compound in the host can be from 3 wt.% to 20 wt.%. In some embodiments, for red and green emitters, the doping level of the emitter compound in the host can be from 1 wt.% to 15 wt.%. The thickness of the thermally evaporated thin-film test sample can be from 50 to 1000 Å.

[0444] In some embodiments, the OLED of this disclosure may include a sensitizer, a receptor, and one or more hosts in the emission region, and the preferred receptor / sensitizer VDR combinations (A)-(D) mentioned above still apply. In these embodiments, the VDR value of a receptor compound can be measured using a thin-film test sample formed of one or more hosts and a receptor, wherein the receptor is the only emitter in the thin-film test sample. Similarly, the VDR value of a sensitizer compound can be measured using a thin-film test sample formed of one or more hosts and a sensitizer, wherein the sensitizer is the only emitter in the thin-film test sample.

[0445] In the production Figure 3 In one example, a 30 nm thick material film with a refractive index of 1.75 was used to monitor emission in a semi-infinite medium with a refractive index of 1.75. Each curve was normalized relative to the photoluminescence intensity 1 (at a zero-degree angle perpendicular to the film surface). As the VDR of the emitter varied, the peak around 45 degrees increased significantly. When the VDR of the experimental data was fitted using software, the modeled VDR was modified until the difference between the modeled data and the experimental data was minimized.

[0446] Since VDR represents the average dipole orientation of the luminescent compound in a thin film sample, even if other luminescent compounds are present in the emitting layer, their VDR measurement will not reflect their VDR if they do not contribute to light emission. Furthermore, the VDR of the luminescent compound can be tuned by including a host material that interacts with it. Therefore, a luminescent compound in a thin film sample with host material A will exhibit one VDR measurement, while the same luminescent compound in a thin film sample with host material B will exhibit a different VDR measurement. Additionally, in some embodiments, it is necessary to form an excimer complex or excimer in an emission state between two adjacent molecules. The VDR of these emission states may differ from that when the only component in the excimer complex or excimer is emitted or present in the sample.

[0447] In some embodiments, the OLED is a plasmonic OLED. In some embodiments, the OLED is a waveguide OLED.

[0448] In some embodiments, the OLED emits white light at room temperature when a voltage is applied across the device.

[0449] In some embodiments, when a voltage is applied across the device, the OLED emits luminescent radiation at room temperature; wherein the first component of the luminescent radiation is emitted by a device having an emission λ. max1 The receptor compound contributes to the emission λ. max1 Independently selected from the following groups: greater than 340 nm to equal to or less than 500 nm, greater than 500 nm to equal to or less than 600 nm, and greater than 600 nm to equal to or less than 900 nm. In some embodiments, the FWHM of the first radiation component is 50, 40, 35, 30, 25, 20, 15, 10, or 5 nm or lower. In some embodiments, the first radiation component has a 10% start point of an emission peak less than 465, 460, 455, or 450 nm.

[0450] In some embodiments, the sensitizer compound is partially or fully deuterated. In some embodiments, the receptor compound is partially or fully deuterated. In some embodiments, the first body is partially or fully deuterated. In some embodiments, the second body is partially or fully deuterated.

[0451] In some embodiments, the sensitizer compound and / or acceptor compound each independently comprises at least one substituent with a sphericity greater than or equal to 0.45, 0.55, 0.65, 0.75, or 0.80. Secondary sphericity is a measure of the three dimensions of a large group. Secondary sphericity is defined as the ratio between principal moments of inertia (PMIs). Specifically, secondary sphericity is the ratio of three times PMI1 to the sum of PMI1, PMI2, and PMI3, where PMI1 is the minimum principal moment of inertia, PMI2 is the second minimum principal moment of inertia, and PMI3 is the maximum principal moment of inertia. The secondary sphericity of the lowest energy conformation of the structure can be calculated after optimizing the ground state using density functional theory. More detailed information can be found in paragraphs

[0054] through

[0059] of U.S. Application No. 18 / 062,110 (filed December 6, 2022), the contents of which are incorporated herein by reference. In some embodiments, the sensitizer compound and / or receptor compound each independently comprise at least one van der Waals volume greater than 153, 206, 259, 290, or 329 Å. 3 Substituents. In some embodiments, compound S1 and / or compound A1 each independently contain at least one substituent with a molecular weight greater than 167, 187, 259, 303 or 305 amu.

[0452] In some embodiments, one of the first body and the second body is a hole transport body, and the other of the first body and the second body is an electron transport body. In some embodiments, the first body is a hole transport body, and wherein the first body comprises at least one chemical group selected from the group consisting of: amino, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, and 5λ. 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium. In some embodiments, the first body is an electron transport body, and wherein the first body comprises at least one chemical group selected from the group consisting of: pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazolium, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, 5,9-dioxa-13b-boronazonaphtho[3,2,1-de]anthracene, borane, nitrile, aza-5λ 2- benzo[d]benzo[4,5]imidazo[3,2-a]imidazo[5,9-dioxa-13b-boronazona[3,2,1-de]anthracene). In some embodiments, one of the first and second bodies is a bipolar body comprising both hole-transporting groups and electron-transporting groups.

[0453] In some embodiments, the OLED further includes a color conversion layer or a color filter.

[0454] In some embodiments, the composition may comprise at least two different compounds selected from the following: a sensitizer compound, a receptor compound, and a host compound.

[0455] In some embodiments, the chemical structure is selected from the group consisting of monomers, polymers, macromolecules and supramolecular molecules, wherein the chemical structure comprises at least two of the following components: sensitizer compound, acceptor compound and host.

[0456] In some embodiments, the premixed co-evaporation source is a mixture of a first compound and a second compound; wherein the co-evaporation source is a co-evaporation source for a vacuum deposition process or an OVJP process; wherein the first compound and the second compound are distinctly selected from Group 1 of the following: sensitizer compounds, acceptor compounds, a first host compound, and a second host compound; wherein the first compound has an evaporation temperature T1 of 150 to 350 °C; wherein the second compound has an evaporation temperature T2 of 150 to 350 °C; wherein the absolute value of T1-T2 is less than 20 °C; wherein the first compound has a concentration C1 in the mixture and a concentration C2 in the test film, the test film being deposited in a vacuum deposition tool at 1 × 10⁻⁶ °C. -6 To 1 × 10 -9 The mixture is formed by evaporating the mixture at a deposition rate of 2 Å / s under constant pressure between the two compounds; and wherein the absolute value of (C1-C2) / C1 is less than 5%. In some embodiments, the mixture further comprises a third compound; wherein the third compound is different from the first and second compounds and is selected from the same group 1; wherein the third compound has an evaporation temperature T3 of 150 to 350 °C, and wherein the absolute value of T1-T3 is less than 20 °C.

[0457] In some embodiments, the first compound has an evaporation temperature T1 of 200°C to 350°C, and the second compound has an evaporation temperature T2 of 200°C to 350°C. In some embodiments, the absolute value of (C1-C2) / C1 is less than 3%. In some embodiments, the first compound has a vapor pressure P1 at 1 atm at T1, and the second compound has a vapor pressure P2 at 1 atm at T2; and the P1 / P2 ratio is in the range of 0.90:1 to 1.10:1. In some embodiments, the first compound has a first mass loss rate and the second compound has a second mass loss rate, wherein the ratio between the first mass loss rate and the second mass loss rate is in the range of 0.90:1 to 1.10:1, 0.95:1 to 1.05:1, or 0.97:1 to 1.03:1. In some embodiments, the first compound and the second compound each have a purity of more than 99%, as determined by high-performance liquid chromatography. In some embodiments, the composition is in liquid form at a temperature less than the lower of T1 and T2.

[0458] In some embodiments, a method for manufacturing an organic light-emitting device may include: providing a substrate on which a first electrode is disposed; and passing the first electrode through a substrate having a 1 × 10⁻⁶ electrode. -6 To 1 × 10 -9 The process involves evaporating a premixed co-evaporation source, which is a mixture of the first and second compounds, in a high-vacuum deposition tool with a chamber base pressure to deposit a first organic layer on the first electrode; and depositing a second electrode on the first organic layer.

[0459] It should be understood that if the embodiments of all the compounds and devices described herein also apply to different aspects of the entire disclosure, then these embodiments may be interchangeable.

[0460] In some embodiments, each of the sensitizer compound, receptor compound, host compound, compound of formula I as defined herein, and all other compounds may be at least 10% deuterated, at least 20% deuterated, at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, the percentage of deuteration has its general meaning and includes the percentage of possible hydrogen atoms (e.g., hydrogen or deuterium positions) substituted by deuterium atoms.

[0461] C. Other aspects of the OLED disclosed herein

[0462] In some embodiments, the OLED may further comprise an additional body comprising a benzo-fused thiophene or a benzo-fused furan containing triphenylene, wherein any substituent in the body is a non-fused substituent independently selected from the group consisting of: C n H 2n+1 OC n H 2n+1 ,OAr1,N(C n H 2n+1 2. N(Ar1)(Ar2), CH=CH-C n H 2n+1 C≡CC n H 2n+1 Ar1, Ar1-Ar2, C n H 2n -Ar1 or no substitution, where n is an integer from 1 to 10; and where Ar1 and Ar2 are independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole and their heteroaromatic analogs.

[0463] In some embodiments, the additional body comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-borona[3,2,1-de]anthracene, azacyclohexylborane, oxaborane, dihydroacrylidine, oxanthracene, dihydrobenzoazasilane, dibenzooxasilane, phenoxazine, phenoxthiazine, dihydrophenazine, fluorene, naphthalene, anthracene, phenanthrene, phenanthroline, benzoquinoline, quinoline, isoquinoline, quinazoline, pyrimidine, pyrazine, pyridine, triazine, boranyl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 - benzo[d]benzo[4,5]imidazo[3,2-a]imidazo and aza-(5,9-dioxa-13b-borona[3,2,1-de]anthracene).

[0464] In some embodiments, the additional body comprises a metal complex.

[0465] In some embodiments, the additional subject is selected from the group consisting of: EG1-MG1-EG1 to EG53-MG27-EG53 having the formula EGa-MGb-EGc, or EG1-EG1 to EG53-EG53 having the formula EGa-EGc when MGb is absent, where a is an integer from 1 to 53, b is an integer from 1 to 27, and c is an integer from 1 to 53. The structures of EG1 to EG53 are shown below:

[0466] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

[0467] The structural diagrams of MG1 through MG27 are shown below:

[0468] , , , , , , , , , , , , , , , , , , , , , , , , , , In the MGb structure shown above, the positions of two bonds in the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are marked with numbers for identification purposes.

[0469] In some embodiments, the subject can be any of its nitrogen-substituted variants, its fully or partially deuterated variants, and combinations thereof. In some embodiments, the subject has the formula EGa-MGb-EGc and is selected from the group consisting of h1 to h112 as defined in the following list of subjects group 2, wherein each of MGb, EGa, and EGc is defined as follows:

[0470]

[0471]

[0472] In the table above, the EGa and EGc structures bonded to one of the asymmetric structures MG10, MG11, MG12, MG13, MG14, MG17, MG24 and MG25 are marked with a numerical prefix, which indicates their bond position in the MGb structure.

[0473] In another aspect, the OLED of this disclosure may also include an emission region comprising a composition as disclosed in the compound section above.

[0474] In some embodiments, the emission region comprises one or more organic layers, at least one of which has a minimum thickness selected from the group consisting of 350, 400, 450, 500, 550, 600, 650, and 700 Å. In some embodiments, at least one of the one or more organic layers is formed by an emission system with a figure of merit (FOM) equal to or greater than a value selected from the group consisting of 2.50, 2.55, 2.60, 2.65, 2.70, 2.75, 2.80, 2.85, 2.90, 2.95, 3.00, 5.00, 10.0, 15.0, and 20.0. The definition of FOM is available in U.S. Patent Application Publication No. 2023 / 0292605, the entire contents of which are incorporated herein by reference. In some embodiments, at least one of the one or more organic layers comprises a compound or a composition of compounds as disclosed in sections A and D of this disclosure.

[0475] In some embodiments, the OLED or emitting region disclosed herein may be incorporated into a full-color pixel arrangement of a device. Such a full-color pixel arrangement of a device includes at least one pixel, wherein the at least one pixel includes a first sub-pixel and a second sub-pixel. The first sub-pixel includes a first OLED, which includes a first emitting region. The second sub-pixel includes a second OLED, which includes a second emitting region. In some embodiments, the first and / or second OLEDs, and the first and / or second emitting regions may be the same or different and may each independently have various device features and embodiments of the inventive compounds included therein, as well as various combinations and sub-combinations of the various device features and embodiments of the inventive compounds included therein, as disclosed herein.

[0476] In some embodiments, the first emission region is configured to emit light with a peak wavelength λ. max1 The second emission region is configured to emit light with a peak wavelength λ. max2 The light. In some embodiments, the peak wavelength λ max1 With λ max2 The difference between them is at least 4 nm but within the same color. For example, light blue and dark blue light as described above. In some embodiments, the first emission region is configured to emit light with a peak wavelength λ in one region of the visible spectrum at 400-500 nm, 500-600 nm, or 600-700 nm. max1 The light emitted; and the second emission region is configured to emit light having a peak wavelength λ in one of the remaining regions of the visible spectrum: 400-500 nm, 500-600 nm, or 600-700 nm. max2The light emitted. In some embodiments, the first emitting region comprises (if more than one) a first number of emitting layers deposited on top of another; and the second emitting region comprises (if more than one) a second number of emitting layers deposited on top of another; and the first number is different from the second number. In some embodiments, both the first emitting region and the second emitting region comprise phosphorescent materials that may be the same or different. In some embodiments, the first emitting region comprises phosphorescent material, while the second emitting region comprises fluorescent material. In some embodiments, both the first emitting region and the second emitting region comprise fluorescent materials that may be the same or different.

[0477] In some embodiments, at least one pixel of an OLED or emitting region comprises a total of N sub-pixels; wherein the N sub-pixels include a first sub-pixel and a second sub-pixel; wherein each of the N sub-pixels includes an emitting region; wherein the total number of emitting regions within at least one pixel is equal to or less than N-1. In some embodiments, the second emitting region is identical to the first emitting region; and each sub-pixel of at least one pixel includes an emitting region identical to the first emitting region. In some embodiments, a full-color pixel arrangement may have multiple pixels including a first pixel region and a second pixel region; wherein at least one display feature in the first pixel region differs from a corresponding display feature in the second pixel region, and wherein the at least one display feature is selected from the group consisting of: resolution, cavity mode, color, external coupling, and color filter.

[0478] In some embodiments, the OLED is a stacked OLED comprising one or more charge generating layers (CGLs). In some embodiments, the OLED comprises a first electrode, a first emitting region disposed above the first electrode, a first CGL disposed above the first emitting region, a second emitting region disposed above the first CGL, and a second electrode disposed above the second emitting region. In some embodiments, the first emitting region and / or the second emitting region may have various device features as described above for pixelation devices. In some embodiments, the stacked OLED is configured to emit white. In some embodiments, one or more of the emitting regions in the pixelated OLED or the stacked OLED comprise a sensitizer and an acceptor having various sensitization device features and various embodiments of the compounds of the invention disclosed herein. For example, the first emitting region is included in a sensitization device while the second emitting region is not included in a sensitization device; in some cases, both the first and second emitting regions are included in a sensitization device.

[0479] In some embodiments, the OLED can emit light from at least 1%, 5%, 10%, 30%, 50%, 70%, 80%, 90%, 95%, 99%, or 100% of plasmonic modes. In some embodiments, at least one of the anode, cathode, or a new layer disposed above the organic emitting layer serves as a reinforcement layer. The reinforcement layer comprises a plasmonic material exhibiting surface plasmon resonance, which is nonradiatively coupled to the emitter material and transfers excited-state energy from the emitter material to the nonradiative modes of surface plasmon polaritons. In some embodiments, the reinforcement layer is positioned at a distance from the organic emitting layer not exceeding a threshold distance, wherein the emitter material has a total nonradiative decay rate constant and a total radiative decay rate constant due to the presence of the reinforcement layer. The threshold distance is the position where the total nonradiative decay rate constant equals the total radiative decay rate constant. Another threshold distance is the distance at which the total radiative decay rate constant divided by the sum of the total nonradiative decay rate constant and the total radiative decay rate constant equals the photoluminescence yield of the emitting material without the reinforcement layer.

[0480] In some embodiments, the OLED further includes an external coupling layer. In some embodiments, the external coupling layer is disposed above the enhancement layer on the side opposite the organic emitting layer. The external coupling layer scatters energy from surface plasmon polaritons. In some embodiments, this energy is scattered as photons into free space. In other embodiments, energy is scattered from the surface plasmon polariton modes of the device into other modes, such as, but not limited to, organic waveguide modes, substrate modes, or another waveguide mode. In some embodiments, one or more intermediary layers may be disposed between the enhancement layer and the external coupling layer. Examples of intermediary layers may be dielectric materials, including organic, inorganic, perovskite, and oxide materials, and may include stacks and / or mixtures of these materials.

[0481] The enhancement layer alters the effective properties of the medium in which the emitter material resides, thereby causing any or all of the following: reduced emissivity, altered emission profile, changes in emission intensity with angle, altered emitter material stability, altered OLED efficiency, and reduced roll-off efficiency of the OLED device. Placing the enhancement layer on the cathode side, anode side, or both sides, or placing the enhancement layer itself as a CGL, produces an OLED device that utilizes any of the aforementioned effects. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, the OLED according to this disclosure may also include any other functional layers commonly found in OLEDs.

[0482] In some embodiments, the reinforcing layer may comprise a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may comprise at least one of the following: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, or Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the reinforcing layer is configured as a planar layer. In other embodiments, the reinforcing layer is characterized by wavelengths arranged periodically, quasi-periodically, or randomly, or by subwavelengths arranged periodically, quasi-periodically, or randomly.

[0483] In some embodiments, the outer coupling layer has a wavelength or subwavelength characteristic of being arranged periodically, quasi-periodically, or randomly. In some embodiments, the outer coupling layer may be composed of a plurality of nanoparticles. In some embodiments, the outer coupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, the outer coupling layer can be adjusted by at least one of the following: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material, adding an additional layer disposed on the plurality of nanoparticles, changing the thickness of a reinforcing layer, or changing the material of a reinforcing layer. The plurality of nanoparticles of the device may be formed from at least one of the following: metal, dielectric material, semiconductor material, metal alloy, mixture of dielectric materials, stack or layer of one or more materials and / or a core of one type of material coated with a shell of another type of material. In some embodiments, the outer coupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, and Ca, alloys or mixtures of these materials, and stacks of these materials. In some embodiments, the outer coupling layer is formed by photolithography. In some embodiments, the outer coupling layer is composed of at least dielectric nanoparticles, wherein the dielectric material is selected from the group consisting of: silicon, silicon nitride, boron nitride, silicon carbide, carbon, diamond, zinc sulfide, zinc selenide, germanium, zinc telluride, potassium niobate, titanium oxide, antimony oxide, niobium pentoxide, tantalum pentoxide, vanadium oxide, gallium pentoxide, gallium phosphate, bismuth oxide, gallium arsenide, indium oxide, silicon dioxide, aluminum gallium, molybdenum oxide, alloys or mixtures of these materials, and stacks of these materials.

[0484] In some embodiments of the plasmonic device, the emitter and / or host compound used in the emitter layer has a vertical dipole ratio (VDR) of 0.33 or greater. In some such embodiments, the emitter and / or host compound has a VDR of 0.40, 0.50, 0.60, 0.70 or greater.

[0485] In another aspect, this disclosure also provides a consumer product comprising an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise compounds as disclosed in the preceding compound section of this disclosure.

[0486] In some embodiments, a consumer product includes an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a composition as described herein.

[0487] In some embodiments, a consumer product may be one of the following: a flat panel display, a computer monitor, a medical monitor, a television set, a signboard, a light for internal or external lighting and / or signaling, a head-up display, a fully transparent or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.

[0488] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to both the anode and cathode. When a current is applied, holes are injected into the anode and electrons into the organic layer from the cathode. The injected holes and electrons migrate toward their respective oppositely charged electrodes. When electrons and holes are localized on the same molecule, "excitons" are formed, which are localized electron-hole pairs with excited energy states. When excitons relax through photoemission mechanisms, light is emitted. In some cases, excitons can be localized on excimers or excimer complexes. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

[0489] Certain OLED materials and configurations are described in U.S. Patent Nos. 5,844,363, 6,303,238 and 5,707,745, which are incorporated herein by reference in their entirety.

[0490] Early OLEDs used emitting molecules that emitted light from a single state (“fluorescence”), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated herein by reference in its entirety. Fluorescence emission typically occurs within timeframes of less than 10 nanoseconds.

[0491] Recently, OLEDs with emitting materials that emit light from the triplet state (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, Vol. 395, 151-154, 1998 (“Baldo-I”); and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Applied Physics Letters, Vol. 75, 3, 4-6 (1999) (“Baldo-II”), are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in columns 5-6 of U.S. Patent No. 7,279,704, which is incorporated herein by reference.

[0492] Figure 1 An organic light-emitting device 100 is shown. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emission layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. The cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 can be fabricated by sequentially depositing the layers. The properties and functions of these various layers, as well as the example materials, are described in more detail in columns 6-10 of US 7,279,704, which is incorporated herein by reference.

[0493] Further examples of each of these layers are available. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of luminescent and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, comprising composite cathodes having a thin layer of metal (e.g., Mg:Ag) having an overlying transparent, conductive, sputtered ITO layer, are disclosed in their entirety in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. Theories and uses of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. Descriptions of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0494] Figure 2 An inverted OLED 200 is shown. The device includes a substrate 210, a cathode 215, an emitter layer 220, a hole transport layer 225, and an anode 230. The device 200 can be fabricated by sequentially depositing these layers. Because the most common OLED configuration has a cathode disposed above the anode, and the device 200 has a cathode 215 disposed below the anode 230, the device 200 can be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 can be used in the corresponding layers of the device 200. Figure 2 Provide an example of how some layers can be omitted from the structure of device 100.

[0495] Figure 1 and 2The simple layered structures described herein are provided by way of non-limiting examples, and it should be understood that embodiments of this disclosure can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the various layers described in different ways, or the layers can be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many examples provided herein describe various layers as comprising a single material, it should be understood that combinations of materials, such as mixtures of host and dopant, or more generally, mixtures, can be used. Furthermore, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emitter layer 220, and can be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise, for example, regarding Figure 1 and 2 Multiple layers of the different organic materials mentioned above.

[0496] Structures and materials not specifically described can also be used, such as OLEDs (PLEDs) containing polymeric materials, as disclosed in, for example, U.S. Patent No. 5,247,190 to Friend et al., which is incorporated herein by reference in its entirety. By another example, OLEDs with a single organic layer can be used. OLEDs can be stacked, for example, as described in, U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated herein by reference in its entirety. OLED structures can deviate from... Figure 1 and 2 The simple layered structure described herein. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as the tabletop structure described in U.S. Patent No. 6,091,195 to Forrest et al., and / or the recessed structure described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated herein by reference in their entirety.

[0497] Further details regarding OLEDs and the definitions described above can be found in U.S. Patent No. 7,279,704, which is incorporated herein by reference in its entirety.

[0498] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can utilize the materials and structures described herein. More generally, organic devices such as organic transistors can utilize the materials and structures described herein.

[0499] In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer including carbon nanotubes. In some embodiments, the OLED further comprises one or more quantum dots. Such quantum dots may be in the emission layer or in other functional layers, such as conversion layers.

[0500] In some embodiments, the OLED step includes a layer comprising a delayed phosphor emitter. In some embodiments, the OLED comprises an RGB pixel arrangement or a white pixel arrangement with a color filter. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel with a diagonal of less than 10 inches or an area of ​​less than 50 square inches. In some embodiments, the OLED is a display panel with a diagonal of at least 10 inches or an area of ​​at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0501] In some embodiments, the compound of Formula I may be an emission dopant. In some embodiments, the compound may generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF) (also known as E-type delayed fluorescence; see, for example, U.S. Application No. 15 / 700,352, which is incorporated herein by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the emission dopant may be a racemic mixture or may be enriched with one enantiomer. In some embodiments, the compound may be homogeneous (each ligand is identical). In some embodiments, the compound may be mixed (at least one ligand is different from the others). In some embodiments, when more than one ligand is coordinated to a metal, the ligands may all be identical. In some other embodiments, at least one ligand is different from the others. In some embodiments, each ligand may be different from each other. This also applies in embodiments where a ligand coordinated to a metal may be linked to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate, or hexadentate ligand. Therefore, in the case where the ligands are linked together, in some embodiments all the ligands may be the same, and in some other embodiments at least one of the linked ligands may be different from the others.

[0502] In some embodiments, the compound can be used as a phosphorescent photosensitizer in an OLED, wherein one or more layers in the OLED contain receptors in the form of one or more fluorescent and / or delayed-emission emitters. In some embodiments, the compound can be used as a component of an excimer complex used as a photosensitizer. As a phosphorescent photosensitizer, the compound must be able to transfer energy to the receptor and the receptor to emit energy or further transfer energy to the final emitter. The receptor concentration can range from 0.001% to 100%. The receptor can be in the same layer as the phosphorescent photosensitizer or in one or more different layers. In some embodiments, the receptor is a TADF emitter. In some embodiments, the receptor is a fluorescent emitter. In some embodiments, emission can be generated by any one or all of the photosensitizer, receptor, and final emitter.

[0503] According to another aspect, a composition comprising the compounds disclosed herein, including compounds of formula I as defined herein.

[0504] The OLEDs disclosed herein can be incorporated into one or more consumer products, electronic component modules, and lighting panels. In some embodiments, the organic layer may be an emission layer, and the compound may be an emission dopant, while in other embodiments, the compound may be a non-emission dopant. In some embodiments, the emission layer may also optionally contain a dopant selected from the group consisting of delayed-motion fluorescence and non-delayed-motion fluorescence.

[0505] In another aspect of this disclosure, a composition comprising a novel compound of formula I disclosed herein is described. The composition may include one or more components disclosed herein selected from the group consisting of: solvent, host, hole injection material, hole transport material, electron blocking material, hole blocking material, and electron transport material.

[0506] This disclosure covers the chemical structure of any novel compound comprising Formula I as defined herein, or a monovalent or multivalent variant thereof. In other words, the compounds of the present invention, or monovalent or multivalent variants thereof, can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of molecules, monomers, polymers, macromolecules, and supramolecular structures (also called supermolecules). As used herein, a “monovalent variant of a compound” refers to the same part of the compound, but in which one hydrogen has been removed and replaced with a bond to the rest of the chemical structure. As used herein, a “multivalent variant of a compound” refers to the same part of the compound, but in which more than one hydrogen has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecular structures, the compounds of the present invention can also be incorporated into supramolecular complexes without covalent bonds.

[0507] D. Combinations of the compounds disclosed herein with other materials

[0508] The materials described herein are various examples of materials that can be used in specific layers in OLEDs. They can also be used in combination with a wide variety of other materials present in the device. For example, the emission dopants disclosed herein can be used by the emission dopants themselves in the EML, or in combination with a wide variety of other emitters, hosts, transport layers, barrier layers, implantation layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds and devices disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0509] a) Conductive dopants:

[0510] Charge transport layers can be doped with conductive dopants to substantially alter their charge carrier density, which in turn changes their conductivity. Conductivity can be increased by generating charge carriers in the matrix material, and, depending on the type of dopant, variations in the Fermi level of the semiconductor can also be achieved. Hole transport layers can be doped with p-type conductive dopants, and n-type conductive dopants are used in electron transport layers. In some embodiments, the conductive dopant comprises at least one chemical group selected from the group consisting of: cyano, fluorinated aryl or heteroaryl, fluorinated alkyl or cycloalkyl, alkylene, heteroaryl, amide, benzodithiophene, and highly conjugated heteroaryl groups extended by acyclic double bonds.

[0511] b) HIL / HTL:

[0512] The hole injection / transport materials used in this disclosure are not particularly limited, and any compound may be used, provided that the compound is commonly used as a hole injection / transport material. Examples of materials include (but are not limited to): phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indole-carbazole derivatives; polymers containing fluorinated hydrocarbons; polymers with conductive dopants; conductive polymers, such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; and metal oxide derivatives, such as MoO. x p-type semiconductive organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylhexacarbonitrile; metal complexes; and crosslinkable compounds.

[0513] Examples of aromatic amine derivatives used for HIL or HTL include (but are not limited to) the following general structures:

[0514] , , , and Ar 1 To Ar9 Each of these is selected from: the group consisting of, for example, aromatic cyclic compounds such as: benzene, biphenyl, biphenylene, triphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azulene; and the group consisting of, for example, aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzene The group consisting of benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanopyridine, benzothiophenopyridine, thiophenopyridine, benzoselenopyridine, and selelenopyridine; and the group consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. 1 To Ar 9 Each of them may be unsubstituted or may be substituted with the general substituents described above, and any two substituents may be joined or fused into a ring.

[0515] In some embodiments, each Ar 1 To Ar 9 Independently comprising groups selected from the following groups:

[0516] , , , , , and Where k is an integer from 1 to 20; X 101 To X 108 It is C or N; Z 101 It is C, N, O, or S.

[0517] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula:

[0518]

[0519] Met is a metal with an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102The coordinating atoms are independently selected from C, N, O, P, and S; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k" is the maximum number of ligands that can be bound to the metal.

[0520] In some embodiments, (Y) 101 -Y 102 (Y) is a 2-phenylpyridine or 2-phenylimidazole derivative. In some embodiments, (Y) 101 -Y 102 Met is a carbene ligand. In some embodiments, Met is selected from Ir, Pt, Pd, Os, Cu, and Zn. In some embodiments, the metal complex has a relative... + The minimum oxidation potential in solution with / Fc coupling is less than about 0.6 V.

[0521] In some embodiments, the HIL / HTL material is selected from the group consisting of: phthalocyanine and porphyrin compounds, starburst triarylamine, CF x Fluorinated hydrocarbon polymers, conductive polymers (e.g., PEDOT:PSS, polyaniline, polythiophene), phosphonic acids and silane SAMs, triarylamines or polythiophene polymers containing conductive dopants, organic compounds containing conductive inorganic compounds (such as molybdenum oxide and tungsten oxide), n-type semiconductive organic complexes, organometallic complexes, crosslinkable compounds, polythiophene-based polymers and copolymers, triarylamines, triarylamines containing spirofluorene cores, arylamine carbazole compounds, triarylamines containing (di)benzothiophene / (di)benzofuran, indole-carbazole, isoindole compounds, and metal carbene complexes.

[0522] c) EBL:

[0523] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emitter layer. The presence of such a blocking layer in a device can result in generally higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, the blocking layer can be used to confine emission to a desired area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy compared to one or more emitters closest to the EBL interface. In some embodiments, the compound used in the EBL contains at least one carbazole group and / or at least one arylamine group. In some embodiments, the HOMO level of the compound used in the EBL is shallower than the HOMO level of one or more of the bodies in the EML. In some embodiments, the compound used in the EBL contains the same molecule or the same functional groups as those used in one of the bodies described below.

[0524] d) Main body:

[0525] The light-emitting layer of the organic EL device disclosed herein preferably contains at least a light-emitting material as a dopant and a host material. Examples of the host material are not particularly limited, and any metal complex or organic compound can be used, as long as the host does not completely quench the emission of the dopant.

[0526] Examples of metal complexes used as the host preferably have the following general formula:

[0527]

[0528] Where Met is a metal; (Y) 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 The coordinating atoms are independently selected from C, N, O, P, and S; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bound to the metal; and k'+k" is the maximum number of ligands that can be bound to the metal.

[0529] In some embodiments, the metal complex is:

[0530]

[0531] (ON) is a bidentate ligand of a metal that coordinates with O and N atoms.

[0532] In some embodiments, Met is selected from Ir and Pt. In another embodiment, (Y 103 -Y 104 ) is a carbaene ligand.

[0533] In some embodiments, the host compound contains at least one selected from the group consisting of, for example, aromatic hydrocarbon cyclic compounds such as: benzene, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, β-carbamate, perylene, and azurite; and aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, and oxazole. Thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziisoxazole, benzothiazazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, acridine, phenazine, phenothiazine, phenothiazine, azira-dibenzothiophene, azira-dibenzofuran, azira-dibenzoselenophene, azira-carbazole, azira-indole-carbazole, azira-triphenylene, azira-tetraphenylene, 5λ 2 -Benzo[d]benzo[4,5]imidazo[3,2-a]imidazolium, 5,9-dioxa-13b-boronazonaphtho[3,2,1-de]anthracene; and groups consisting of 2 to 10 cyclic structural units, said cyclic structural units being groups of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups and bonded to each other directly or via at least one of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, chain structural units, and aliphatic cyclic groups. Each option within each group may be unsubstituted or may be substituted with general substituents as described herein or may be further fused.

[0534] In some embodiments, the host compound comprises at least one group selected from the group consisting of:

[0535] , , , , , , , , , , , , , , , , , , , ,and , where k is an integer from 0 to 20 or from 1 to 20. X 101 To X108 Independently selected from C or N. Z 101 and Z 102 It is independently selected from C, N, O, or S.

[0536] In some embodiments, the host material is selected from the group consisting of: arylcarbazole, metal 8-hydroxyquinoline compounds (e.g., alq3, balq), metal phenoxybenzothiazole compounds, conjugated oligomers and polymers (e.g., polyfluorene), aromatic fused rings, zinc complexes, alkyl-based compounds, aryltriphenylene compounds, polyfused heteroaryl compounds, donor-acceptor molecules, dibenzofuran / dibenzothiophene compounds, polymers (e.g., pvk), spirofluorene compounds, spirofluorene-carbazole Zrazole compounds, indolocarbazole, 5-membered electron-deficient heterocycles (e.g., triazoles, oxadiazoles), tetraphenylene complexes, metal phenoxypyridine compounds, metal coordination complexes (e.g., Zn, Al containing N^N ligands), dibenzothiophene / dibenzofuran-carbazole compounds, silicon / germanium aryl compounds, aryl benzoyl esters, non-conjugated carbazoles, aza-carbazole / dibenzofuran / dibenzothiophene compounds, and high triplet state organometallic complexes (e.g., metal-carbaene complexes).

[0537] e) Emitter material in EML:

[0538] One or more additional emitter materials may be used in conjunction with the compounds or devices disclosed herein. In the present devices as described herein, one or more additional emitter materials may be emissive or non-emissive. For example, an additional emitter material as a phosphorescent material may be used in an OLED device to provide a sensitizer function, and the same phosphorescent material may also be used in the OLED device as a luminescent phosphorescent emitter in another layer. Examples of emitter materials are not particularly limited, and any compound may be used as long as it is capable of generating emission in a conventional OLED device. Examples of suitable additional emitter materials include, but are not limited to, compounds capable of generating emission via phosphorescence, non-delayed fluorescence, delayed fluorescence (especially thermally activated delayed fluorescence, i.e., TADF (also known as E-type delayed fluorescence)), triplet-triplet annihilation, or combinations thereof. Each of these materials suitable as additional emitter materials has been described in the preceding sections.

[0539] f) HBL:

[0540] Hole blocking layers (HBLs) can be used to reduce the number of holes and / or excitons leaving the emitter layer. The presence of such blocking layers in a device can result in generally higher efficiency and / or longer lifetime compared to similar devices lacking a blocking layer. Furthermore, blocking layers can be used to confine emission to the desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (farthest from vacuum level) and / or higher triplet energy compared to one or more emitters closest to the HBL interface.

[0541] In some embodiments, the compounds used in HBL contain the same molecules or the same functional groups as those used in the main body described above.

[0542] In some embodiments, the compound used in HBL contains at least one of the following groups selected from the group consisting of:

[0543] , , , , and Where k is an integer from 1 to 20; L 101 It is another ligand, and k' is an integer from 1 to 3.

[0544] g) ETL:

[0545] An electron transport layer (ETL) may comprise a material capable of transporting electrons. The ETL may be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used, provided it is typically used for electron transport.

[0546] In some embodiments, the compounds used in the ETL contain at least one of the following groups in their molecules:

[0547] , , , , , , , , , and fullerenes; where k is an integer from 1 to 20, X 101 To X 108 Selected from C or N; Z 101 Choose a group consisting of C, N, O, and S.

[0548] In some embodiments, the metal complexes used in the ETL contain, but are not limited to, the following general formula:

[0549]

[0550] Wherein (ON) or (NN) are bidentate ligands of metals that coordinate with atoms O, N, or N,N; L 101 It is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be bonded to the metal.

[0551] In some embodiments, the ETL material is selected from the group consisting of: anthracene-benzimidazole compounds, azirtriene derivatives, anthracene-benzothiazole compounds, metal 8-hydroxyquinoline compounds, metal hydroxybenzoquinoline compounds, bathocuprine compounds, 5-membered electron-deficient heterocycles (e.g., triazoles, oxadiazoles, imidazoles, benzimidazoles), thiophene compounds, arylborane compounds, fluorinated aromatic compounds, fullerenes (e.g., C60), triazine complexes, and Zn(N^N) complexes.

[0552] h) Charge Generation Layer (CGL)

[0553] In tandem or stacked OLEDs, the conduction layer (CGL) plays a fundamental role in performance. It consists of an n-doped layer and a p-doped layer, respectively, for injecting electrons and holes. Electrons and holes are supplied by the CGL and the electrodes. Electrons and holes consumed in the CGL are refilled by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials contain n- and p-conductive dopants used in the transport layer.

[0554] In any of the compounds disclosed herein, hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in a compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, and 100%. As used herein, the percentage of deuteration has its general meaning and includes the percentage of all possible hydrogen and deuterium atoms replaced by deuterium atoms. In some embodiments, the deuterium atom is attached to an aromatic ring. In some embodiments, the deuterium atom is attached to a saturated carbon atom, such as an alkyl or cycloalkyl carbon atom. In some other embodiments, the deuterium atom is attached to a heteroatom, such as a Si or Ge atom.

[0555] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. For instance, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. The claimed invention may therefore include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that various theories regarding why the invention works are not intended to be limiting.

[0556] It should also be understood that if the embodiments of all the compounds and devices described herein are also applicable to different aspects of the entire disclosure, then these embodiments may be interchangeable.

[0557] E. Experimental Section

[0558] Synthesis of Compound 1 of the present invention

[0559]

[0560] Iodobenzene (2) (40.65 g, 22.2 mL, 199.3 mmol, 10 equivalents) was added to a stirred solution of 3,5-dibromoaniline (1) (5 g, 19.93 mmol, 1 equivalent) in toluene (20 mL). Then, potassium hydroxide (KOH) (9 g, 160.4 mmol, 8 equivalents), 1,10-phenanthroline (750 mg, 4.16 mmol, 0.2 equivalents), and copper iodide (I) (CuI) (800 mg, 4.2 mmol, 0.2 equivalents) were added. The mixture was heated at 110 °C for 16 hours, and the reaction progress was monitored by thin-layer chromatography (TLC) and liquid chromatography-mass spectrometry (LCMS). After the reaction was complete, water (20 mL) and ethyl acetate (20 mL) were added, and the suspension was filtered through diatomaceous earth, washed with ethyl acetate, and extracted. The organic layer was washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate (Na2SO4), and concentrated. Excess iodobenzene was also evaporated under vacuum at a high water bath temperature, followed by purification of the crude product by chromatography. 5.2 g of the desired product 3,5-dibromo-N,N-diphenylaniline (3) was obtained, with a yield of 64.73%.

[0561]

[0562] 1-Bromo-3,5-di-tert-butylbenzene (5) (13.47 g, 50 mmol, 2.5 equivalents) was added to a stirred solution of phenyl-1,3-diamine (4) (2.16 g, 20 mmol, 1 equivalent) in 1,4-dioxane (140 ml), and the solution was continuously purged with argon gas via a balloon. Then sodium tert-butoxide (NaO) was added. tBu (6.72 g, 69.93 mmol, 3.5 equivalents) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (192 mg, 0.4 mmol, 0.02 equivalents) were added, and the mixture was purged with argon for another 20 min. Palladium(II) acetate (Pd(OAc)2) (45 mg, 0.2 mmol, 0.01 equivalents) was added, and the mixture was purged with argon for another 5 min. The mixture was heated at 110 °C for 16 h, and the reaction progress was monitored by TLC and LCMS. After the reaction was completed, the mixture was filtered through diatomaceous earth, concentrated, and the crude product was purified by chromatography. 6.5 g (67% yield) of N1,N3-bis(3,5-di-tert-butylphenyl)phenyl-1,3-diamine was obtained.

[0563]

[0564] Will KO t Bu (6.944 g, 61.89 mmol, 3 equivalents) and 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (Xantphos) (3.581 g, 6.189 mmol, 0.3 equivalents) were added to a stirred solution of (6) N1,N3-bis(3,5-di-tert-butylphenyl)benzene-1,3-diamine (10 g, 20.63 mmol, 1 equivalent) and (3) 3,5-dibromo-N,N-diphenylaniline (20.79 g, 51.57 mmol, 2.5 equivalents) in toluene (100 ml), and the mixture was purged with argon for 20 minutes. Tris(dibenzylacetone)dipalladium(0) (Pd2dba3) (1.889 g, 2.063 mmol, 0.1 equivalents) was added to the reaction mixture, and purging was continued for another 10 minutes. After purging, the mixture was heated at 110°C for 16 hours. After heating, the crude mixture was filtered through diatomaceous earth, washed with ethyl acetate, concentrated, and purified by column chromatography to obtain 11.53 g (7) N1,N1'-(1,3-phenylene)bis(5-bromo-N1-(3,5-di-tert-butylphenyl)-N3,N3-diphenylbenzene-1,3-diamine), with a yield of 49.63%.

[0565]

[0566] Tribromoborane (777 mg, 0.30 mL, 14 equivalents, 3.10 mmol) was added to (7) N1,N1'-(1,3-phenylene)bis(5-bromo-N1-(3,5-di-tert-butylphenyl)-N3,N3-diphenylbenzene-1,3-diamine) (0.250 g, 1 equivalent, 221 μmol) in a deoxygenated stirred solution of anhydrous 1,2-dichlorobenzene (4.43 mL). The reaction mixture was stirred at room temperature (approximately 25 °C) for 1.5 h, then treated with N-ethyl-N-isopropylpropyl-2-amine (1.20 g, 1.62 mL, 42 equivalents, 9.30 mmol) and heated to 210 °C. After heating, the reaction was quenched with isopropanol and diluted in 30 mL of dichloromethane (DCM). The crude solution was passed through a diatomaceous earth pad, concentrated under reduced pressure, and then purified by column chromatography to give 0.101 g of compound 8, with a yield of 38%.

[0567]

[0568] First, 8 (0.045 g, 1 equivalent, 39 μmol), zinc dicyandiamide (23 mg, 5 equivalent, 0.20 mmol), and potassium carbonate (K₂CO₃) (65 mg, 12 equivalent, 0.47 mmol) were dissolved in anhydrous N,N-dimethylformamide (DMF) (2.800 mL), and the stirred compound was purged with nitrogen for 5 min. After purging, XPhos (15 mg, 0.8 equivalent, 31 μmol) and tris(dibenzylacetone)dipalladium(O) (7.2 mg, 0.2 equivalent, 7.9 μmol) were added, and the reaction was heated to 110 °C. After heating, the crude mixture was diluted with 20 mL of DCM and then extracted with K₂CO₃ solution. The organic layer was separated, dried over Na₂SO₄, and then concentrated under reduced pressure. The concentrated crude product was purified by column chromatography to give 8 mg of compound 1 of the present invention in 20% yield.

[0569] Synthesis of Compound 4 of the present invention

[0570]

[0571] (10) 2'-iodo-1,1':3',1"-terphenyl-2,2",3,3",4,4",5,5",6,6"-d10 (199.3 mmol, 10 equivalents), potassium hydroxide (160.4 mmol, 8 equivalents), 1,10-phenanthroline (4.16 mmol, 0.2 equivalents), and CuI (4.2 mmol, 0.2 equivalents) were sequentially added to a stirred solution of 3,5-dibromo-N-phenylaniline (19.93 mmol, 1.0 equivalents) in toluene (20 mL). The resulting mixture was heated at approximately 110 °C for 16 hours. The reaction progress was monitored by TLC and LCMS. After completion, water (20 mL) and ethyl acetate (20 mL) were added, and the resulting suspension was filtered through diatomaceous earth and washed with ethyl acetate. The organic layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by chromatography to give compound 11.

[0572]

[0573] Potassium tert-butoxide (61.89 mmol, 3.0 equivalent) and Xantphos (6.189 mmol, 0.3 equivalent) can be added to (12) N1,N1'-(1,3-phenylene)bis(N1-([1,1':3',1"-terphenyl]-2'-yl-2,2",3,3",4,4",5,5",6,6"-d10)-5-bromo-N3,N3-diphenylphenyl-1,3-diamine) (20.63 mmol, 1.0 equivalent) and (11) N-(3,5-dibromophenyl)-N-phenyl-[1,1':3',1"-terphenyl]-2'-amine-2,2",3,3",4,4",5,5",6,6"-d10 (51.57 mmol, 2.5 equivalent) in a stirred solution of toluene (100 mL). The reaction mixture was purged with argon for 20 minutes, followed by the addition of Pd₂(dba)₃ (2.063 mmol, 0.1 equivalent), and argon purging was continued for another 10 minutes. The mixture was then heated at approximately 110 °C for 16 hours. After heating, the crude reaction mixture was filtered through diatomaceous earth, washed with ethyl acetate, concentrated, and purified by column chromatography to obtain 13.

[0574]

[0575] Tribromoborane (3.10 mmol, 14 equivalents) was added to compound 13 (221 μmol, 1.0 equivalents) in a deoxygenated, stirred solution of anhydrous 1,2-dichlorobenzene (4.43 mL). The reaction mixture was stirred at room temperature for about 1.5 hours, then treated with N-ethyl-N-isopropylpropyl-2-amine (9.30 mmol, 42 equivalents) and heated to about 210 °C. After heating, the reaction was quenched with isopropanol and diluted with dichloromethane (30 mL). The crude solution was filtered through a diatomaceous earth filter, concentrated under reduced pressure, and purified by column chromatography to give compound 14.

[0576]

[0577] A stirred solution of (14) (39 μmol, 1.0 equivalent), zinc dicyandioxide (0.20 mmol, 5.0 equivalent), and potassium carbonate (0.47 mmol, 12 equivalent) in anhydrous DMF (2.80 mL) was purged with nitrogen for about 5 minutes. After purging, XPhos (31 μmol, 0.8 equivalent) and tris(dibenzylacetone)dipalladium(0) (7.9 μmol, 0.2 equivalent) were added, and the reaction mixture was heated to about 110 °C. After heating, the crude mixture was diluted with dichloromethane (20 mL) and extracted with an aqueous potassium carbonate solution. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to obtain compound 4 of the present invention.

[0578] Compound 11 of the present invention can be synthesized according to steps similar to those used in the synthesis of compound 1 of the present invention:

[0579]

[0580] A stirred solution of 8 (39 μmol, 1.0 equivalent), β-2-benzoxazolylboronic acid (0.10 mmol, 2.5 equivalent), and potassium carbonate (0.47 mmol, 12 equivalent) in anhydrous DMF (2.80 mL) was purged with nitrogen for about 5 minutes. After purging, XPhos (31 μmol, 0.8 equivalent) and tris(dibenzylacetone)dipalladium(O) (7.9 μmol, 0.2 equivalent) were added, and the reaction mixture was heated to about 110 °C. After heating, the crude mixture was diluted with dichloromethane (20 mL) and extracted with an aqueous potassium carbonate solution. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to give compound 11 of the present invention.

[0581] Synthesis of Compound 12 of the present invention

[0582] Compound 12 of the present invention can be obtained by starting with the steps shown below and following steps similar to those for the synthesis of compound 1 of the present invention:

[0583]

[0584] The emission spectrum of compound 1 of the present invention was measured. Emission spectra were collected using a Horiba Fluorolog-3 spectrophotometer equipped with a Synapse Plus CCD detector. All samples were excited at 340 nm. The photoluminescence quantum yield (PLQY) was measured using a Hamamatsu Quantaurus-QY Plus UV-NIR absolute PL quantum yield spectrometer with an excitation wavelength of 340 nm. A solution of 1% emitter and poly(methyl methacrylate) (PMMA) in toluene was prepared, filtered, and dropwise cast onto a quartz substrate. The results are shown in Table 1.

[0585] Table 1. Photophysical data

[0586]

[0587] The compounds of the present invention were also evaluated computationally. Calculations were performed using the B3LYP function with the CEP-31G basis function set. Geometric optimization was performed in vacuum. Excitation energies were obtained for these optimized geometries using time-dependent density functional theory (TDDFT). A continuous solvent model was applied in the TDDFT calculations to simulate tetrahydrofuran solvent. All calculations were performed using the Gaussian program. The calculated values ​​obtained using the density functional theory (DFT) functional sets and basis function sets identified above are theoretical values. Synthetic calculation schemes (e.g., Gaussian16 using the combined B3LYP and CEP-31G schemes as used herein) rely on the assumption that electronic effects are additive, and therefore larger basis function sets can be used to extrapolate to the complete basis function set (CBS) limits. However, when the goal of a study is to understand the variations in HOMO, LUMO, S1, T1, bond dissociation energies, etc., of a range of structure-related compounds, similar additive effects are expected. Therefore, although the absolute error introduced by B3LYP may be quite large compared to other calculation methods, the relative differences between the HOMO, LUMO, S1, T1, and bond dissociation energy values ​​calculated using the B3LYP protocol are expected to reproduce the experiments well. See, for example, Hong et al., *Chem. Mater.* 2016, 28, 5791-98, 5792-93 and Supplementary Information (discussing the reliability of DFT calculations in the context of OLED materials). Furthermore, for iridium or platinum complexes applicable to the OLED field, the data obtained from DFT calculations are closely correlated with actual experimental data. See Tavasli et al., *Journal of Materials Chemistry*, 2012, 22, 6419-29, 6422 (showing DFT calculations closely correlated with actual data for various emission complexes); Morello, GR, *Journal of Molecular Modeling*, 2017, 23:174 (studying various DFT functional groups and basis function groups and concluding that the combination of B3LYP and CEP-31G is particularly accurate for emission complexes). As a post-processing step following the aforementioned DFT and TDDFT calculations, the excited-state transition characteristics are determined. This analysis allows the excited state to be decomposed into holes (i.e., the sites of excitation origin) and electrons (i.e., the final positions of the excited state). Furthermore, since this analysis is based on calculated properties, it is objective and reproducible; see Mai et al., Coord. Chem. Rev. 2018, 361, 74-97 (discussing the theoretical basis for excited-state decomposition in transition metal complexes).

[0588] The results for compounds 2 through 12 of the present invention are shown in Table 2 below. Depending on the position of the features of the present invention, S1, T1, HOMO, and LUMO can be cleverly adjusted to meet the needs of different applications.

[0589] Table 2. DFT Data

[0590]

[0591]

Claims

1. A compound comprising formula I The structure, wherein: Y A Y B Y C and Y D Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR'; R A R B and R C Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R, R', R 1 R 2 R 3 R 4 R A R B and R C Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; R 1 R 2 R 3 Or R 4 At least one of them is an electron-withdrawing group; Any two substituents can join or fused to form a ring.

2. The compound according to claim 1, wherein Y A Y B Y C Or Y D At least one of them is O, S, Se, NR, BR, BRR', PR, PRR', CR, CRR', S=O, SO2, P(O)R, SiRR', or GeRR'.

3. The compound according to claim 1, wherein Y A Y B Y C Or Y D At least three of them are NR.

4. The compound according to claim 1, wherein Y A Y B Y C Or Y D At least one of them contains an electron-donating group; and / or wherein R 1 R 2 R 3 Or R 4 At least two of them are independently electron-withdrawing groups.

5. The compound according to claim 1, wherein Y A Y B Y C Or Y D At least one of them contains at least one electron donor group selected from the group consisting of structures in List A1 below: , , , , , , , , , , , , , , , , , , , , , , and its substituted or aza-substituted variants; Where Y T Y U Y V and Y W Each of them is independently selected from the following groups: BR, NR, PR, O, S, Se, C=O, S=O, SO2, BRR', CRR', SiRR', and GeRR'; Where each of R, R' and R T They can be the same or different, and each R T Independently, it is a donor group, an acceptor group, an organic linking group bonded to a donor group, an organic linking group bonded to an acceptor group, or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, aryl, heteroaryl, and combinations thereof; and Each R and R' is independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof.

6. The compound of claim 1, wherein the compound is selected from the group consisting of structures listed in A4 below: , , , , , , , , , , , and ; in: Y E and Y F Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR'; R E and R F Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R E and R F Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; The remaining variables are the same as those previously defined; and Any two substituents can join or fuse to form a ring.

7. The compound according to claim 1,The compounds mentioned are selected from the group consisting of: compound 1-(Eh)(Ei)(Ej)(Ek)(Rv)(Yl)(Ym)(Yo)(Yp), compound 2-(Ei)(Rs)(Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), compound 3-(Eh)(Ei)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), compound 4-(Ei)(Ej)(Ek)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), compound 5-(Ei)(Ej)(Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), compound 6-(Eh)(Ek)(Rs)(Rt)(Rv)(Yl) (Ym)(Yo)(Yp), Compound 7-(Eh)(Ei)(Ej)(Ek)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), Compound 8-(Ei)(Rs)(Rt) (Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 9-(Ei)(Ek)(Rs)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 10-(Ei)(Ej)(Rt)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 11-(Ei)(Rv)(Yl), Compound 12-(Ei)(Ek)(Rv)(Yl), Compound 13-(Ei)(Ek)(Rv)(Yl)(Ym), Compound 14-(Ei)(Rv)(Yl)(Ym), Compound 15-(Ei)(Ek)(Rv)(Yl) (Ym), Compound 16-(Ei)(Rv)(Yl)(Ym), Compound 17-(Ei)(Rs)(Rt)(Rv)(Yl)(Ym)(Yo)(Yp), Compound 18-(Ei)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), Compound 19-(Ei)(Rs)(Rt)(Rv)(Rw)(Yl), Compound 20-(Ei)(Rv) Compounds 21-(Ei)(Rs)(Rt)(Rv)(Yl), 22-(Eh)(Ek)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), 23-(Ei)(Ej)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), 24-(Eh)(Ek)(Rv)(Rw)(Yl), 25-(Ei)(Ej)(Rv)(Rw)(Yl), 26-(Ei)(Rv)(Rw)(Yl)(Ym)(Yo)(Yp), 27-(Ei)(Rv)(Rw) (Yl)(Ym)(Yo)(Yp), 28-(Ei)(Rv)(Rw)(Yl), and 29-(Ei)(Rv)(Rw)(Yl); Each of Rs, Rt, Rv and Rw is independently selected from R1 to R146; each of Ei, Ej, Eh and Ek is independently selected from E1 to E171; and each of Yl, Ym, Yo and Yp is independently selected from Y1 to Y149, wherein Y1 to Y146 are defined as N-R1 to N-R146 respectively, Y147 is O, Y148 is S and Y149 is Se; Each of compounds 1-(E1)(E1)(E1)(E1)(R1)(Y1)(Y1)(Y1)(Y1) to 29-(E171)(R146)(R146)(Y149) is as defined in Listing A5 below: Each of E1 to E171 is defined as shown in Listing A3 below: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; And each of R1 to R146 is defined as shown in Listing A6 below: 。 8. The compound of claim 1, wherein the compound is selected from the group consisting of structures listed in A7 below: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and .

9. An organic light-emitting device (OLED) comprising: anode; cathode; and An emission region disposed between the anode and the cathode, wherein the emission region contains formula I Compounds with the structure , wherein: Y A Y B Y C and Y D Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR'; R A R B and R C Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R, R', R 1 R 2 R 3 R 4 R A R B and R C Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; R 1 R 2 R 3 Or R 4 At least one of them is an electron-withdrawing group; Any two substituents can join or fused to form a ring.

10. The OLED of claim 9, wherein the emitting region further comprises compound S1, wherein the compound comprising the structure of formula I is a receptor (A1), and the compound S1 is a sensitizer capable of transferring energy from at least one of its excited states to an excited state of the receptor A1 at room temperature.

11. The OLED according to claim 10, wherein the compound S1 has the formula M(L 1 ) x (L 2 ) y (L 3 ) z ; Where L 1 L 2 and L 3 They can be the same or different; Where x is 1, 2, or 3; Where y is 0, 1, or 2; Where z is 0, 1, or 2; Metal M is selected from the following group: Ir, Pt, Pd, Au, Ag, and Cu; Where x+y+z is the oxidation state of the metal M; Where L 1 Select the group consisting of structures from the following list of ligands: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; Where L 2 and L 3 Independent freedom of choice The group consisting of the structures of the ligand list defined in this article; in: T can be freely selected from the following groups: B, Al, Ga, and In; K 1' It is a direct key or a selection of the following groups: NR e PR e , O, S and Se; Each Y 1 To Y 13 Independently select groups composed of free carbon and nitrogen; Y' selects from the following groups: 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 ; R e and R f They can be fused or joined to form rings; Each R a R b R c and R d It can independently represent monosubstituted to the maximum possible number of substitutions or no substitution; Each R a1 R b1 R c1 R d1 R a R b R c R d R e and R f Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogroup, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, selenalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and R a1 R b1 R c1 R d1 R a R b R c and R d Any two of them can fused or joined to form a ring or a polydentate ligand.

12. The OLED of claim 10, wherein the sensitizer S1 has a formula selected from the group consisting of structures listed in List 3: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; in: X 96 To X 99 Each of them is independently C or N; Y 100 and Y 200 Each of them is independently selected from the group consisting of NR, O, S, and Se; L is independently selected from the following groups: direct bond, BR, BRR', NR, PR, O, S, Se, C=O, C=S, C=Se, C=NR, C=CRR', S=O, SO2, CR, CRR', SiRR', GeRR', alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof; X 100 Each time it appears, select from the following groups: O, S, Se, NR", and CRR'; Each R 10a R 20a R 30a R 40a R 50a R A" R B" R C" R D" R E" and R F" Independently represent monosubstituted, at most maximum substituted, or unsubstituted; Each R, R', R 10a R 11a R 12a R 13a R 20a R 30a R 40a R 50a R 60 R 70 R 97 R 98 R 99 R A1' R A2' R A" R B" R C" R D" R E" R F" R G" R H" R I" R J" R K" R L" R M" and R N" Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boranyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl, and combinations thereof; and Any two substituents can join or fused to form a ring.

13. The OLED of claim 10, wherein the compound A1 is selected from the group consisting of structures listed in A4 below: , , , , , , , , , , , and ; in: Y E and Y F Each of them is independently selected from the following groups: O, S, Se, NR, BR, BRR', PR, PRR', CR, C=O, C=NR', C=CRR', C=S, C=Se, CRR', S=O, SO2, P(O)R, SiRR', and GeRR'; R E and R F Each of these terms independently represents a single substitution up to the maximum permissible substitution or no substitution; Each R E and R F Independently, it is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silalkyl, germanalkyl, boranalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, selenyl and combinations thereof; The remaining variables are the same as those previously defined; and Any two substituents can join or fused to form a ring.

14. The OLED of claim 10, wherein the compound A1 is selected from the group consisting of structures listed in A5 below: Each of E1 to E171 is defined as shown in Listing A3 below: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , and ; And each of R1 to R146 is defined as shown in Listing A6 below: 。 15. A consumer product comprising the OLED according to claim 9.

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