Aromatic amine derivatives organic electroluminescent materials and devices

Abstract

Disclosed are aromatic amine derivative organic electroluminescent materials and devices thereof. The compounds are aromatic amine substituted pyrene compounds, wherein the compounds have a substituted or unsubstituted (hetero)aryl and a five-membered (hetero)cyclic hydrocarbon and a substituted or unsubstituted bi(hetero)aryl aromatic amine structure, and can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide better device performance, such as higher external quantum efficiency and narrower half-peak width, etc.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a pyrene compound comprising an aromatic amine-substituted compound, and an organic electroluminescent device comprising the compound and a compound formulation. Background Technology

[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] The color of OLED emission can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Phosphorescent materials for green, yellow, and red OLEDs have been successfully commercialized. Currently, phosphorescent blue OLEDs suffer from short lifespans, difficulty in achieving deep blue, blue unsaturation, and high operating voltages. Fluorescent blue OLEDs have longer lifespans than phosphorescent blue OLEDs, but suffer from low efficiency, thus there is a strong need to improve the efficiency and other performance characteristics of fluorescent blue electroluminescent devices.

[0006] WO2009107596A1 discloses pyrene compounds with triarylamine substitution of benzo[a]alicyclic rings, with the general formula: Wherein the substituent R 21 -R 24 It can form rings to create the following structure Specifically, the structure is as follows:

[0007] The specific structure disclosed includes and However, the patent application did not realize the impact of introducing benzocyclic hydrocarbons into aromatic amines on device performance, nor did it disclose or teach that having benzocyclic hydrocarbons and biaryl structures would improve device performance.

[0008] CN107556239A discloses a pyrene compound containing an acridine structure, with the following general formula: Ar1 and Ar2 can be heterocyclic groups, with specific structures including... However, the patent application mainly targets a series of pyrene compounds with acridine-substituted aromatic amines, without paying attention to the improvement of device performance brought about by benzo[a]heterocyclic hydrocarbons, nor does it disclose or teach the device effects obtained by introducing benzo[a]heterocyclic hydrocarbons or benzo[a]heterocyclic hydrocarbons into aromatic amines or by having another aryl group in the aromatic amine be a biaryl group.

[0009] These documents disclose some fluorescent luminescent materials with aromatic amine structures centered around pyrene. However, further development of fluorescent luminescent materials is still needed to achieve higher device performance. Summary of the Invention

[0010] The present invention aims to provide a series of novel pyrene compounds having substituted or unsubstituted (hetero)aryl and five-membered (hetero)cyclic hydrocarbons and substituted or unsubstituted bi(hetero)aryl aromatic amine structures to solve at least some of the above-mentioned problems.

[0011] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0012]

[0013] In Equation 1,

[0014] Substituent R1-R 10 At least one of them has the structure of Equation 2:

[0015]

[0016] And the substituent R1-R 10 The remaining elements, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or Unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0017] In Equation 2,

[0018] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-60 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-60 carbon atoms, or combinations thereof;

[0019] X1-X3 are selected from CR each time they appear, either the same or different. x Or N;

[0020] Y1 and Y5 are selected from CR each time they appear, either in the same or different ways. y1 Or N;

[0021] Y2-Y4 are selected from CR each time they appear, either in the same or different ways. y2 CR y3 Or N, and at least one of Y2-Y4 is CR y2 ;

[0022] Z is selected from C(R) each time it appears the same or different. z )2, NR z , O, S or Se;

[0023] R x R y3 and R z Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0024] R y1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

[0025] R y2 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0026] Adjacent substituent R x R y1 R y3 They can be arbitrarily connected to form a loop;

[0027] Substituent R z They can be arbitrarily connected to form a loop;

[0028] * represents the position of the substituent of Formula 2 connected to Formula 1.

[0029] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which comprises the compound having the structure of Formula 1. The specific structure of the compound is described in the foregoing embodiments.

[0030] According to another embodiment of the present invention, a compound formulation is also disclosed, comprising the compound having the structure of Formula 1. The specific structure of the compound is described in the foregoing embodiments.

[0031] This invention provides a series of novel pyrene compounds with substituted or unsubstituted (hetero)aryl pentane ring hydrocarbons and substituted or unsubstituted bi(hetero)aryl aromatic amine structures, which can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide better device performance, such as higher external quantum efficiency and narrower full width at half maximum (FWHM). Attached Figure Description

[0032] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0033] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. Detailed Implementation

[0034] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0035] Each of these layers has numerous examples. 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 at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is 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 at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use 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 also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0036] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0037] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0038] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0039] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0040] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0041] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further 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 may still be described as being "disposed" on the anode.

[0042] 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.

[0043] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0044] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0045] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0046] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0047] Definition of the term "substituent group"

[0048] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0049] Alkyl groups – including straight-chain and branched alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Additionally, alkyl groups may optionally be substituted. The carbon atoms in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and neopentyl are preferred.

[0050] Cycloalkyl – as used herein, includes cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 carbon atoms in the ring, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Additionally, the cycloalkyl group may optionally be substituted. The carbon atoms in the ring may be substituted with other heteroatoms.

[0051] Alkenyl – as used herein – encompasses both straight-chain and branched olefin groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl. Additionally, the alkenyl group may be optionally substituted.

[0052] Alkynyl – as used herein, encompasses both straight-chain and branched alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, the alkynyl group may be optionally substituted.

[0053] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, leucine, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Furthermore, the aryl group may optionally be substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylyl, 3,4-dimethylyl, 2,5-dimethylyl, methyltrimethylyl, and m-tetraphenyl.

[0054] Heterocyclic groups or heterocycles – as used herein, consider aromatic and non-aromatic cyclic groups. Isoaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, and sulfur. Heterocyclic groups can also be aromatic heterocyclic groups having at least one heteroatom selected from nitrogen, oxygen, sulfur, and selenium atoms.

[0055] Heteroaryl groups – as used herein, both non-fused and fused heteroaryl groups comprising 1 to 5 heteroatoms are considered. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, 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 Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzothiophene pyridine, thiophene dipyridine, benzothiophene pyridine, thiophene dipyridine, benzoselenophene pyridine, selenobenzobispyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0056] Alkoxy groups are represented by -O-alkyl groups. Examples and preferred examples of alkyl groups are the same as described above. Examples of alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. Alkoxy groups having 3 or more carbon atoms can be linear, cyclic, or branched.

[0057] Aryloxy groups are represented by -O-aryl or -O-heteroaryl groups. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of aryloxy groups having 6 to 40 carbon atoms include phenoxy and biphenyloxy groups.

[0058] Araneyl group – as used herein, an alkyl group having an aryl substituent. Additionally, araneyl groups may optionally be substituted. Examples of araneyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-2-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred.

[0059] The term "aza" in azafluorene, azaspirodifluorene ring, azadibenzofuran, aza-dibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic fragment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0060] In this disclosure, unless otherwise defined, when any one of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alksilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphinyl, it means that any one of the groups selected from alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alksilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl can be one or more selected from deuterium, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 carbon atoms. The substituted group consists of cycloalkyl groups, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aroxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted aryl groups having 6-30 carbon atoms or preferably unsubstituted aryl groups having 6-12 carbon atoms, unsubstituted heteroaryl groups having 3-30 carbon atoms or preferably unsubstituted heteroaryl groups having 3-12 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.

[0061] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0062] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds may be preferred due to their ability to enhance device efficiency and stability. In the compounds mentioned in this disclosure, a deuterated substituent, such as a deuterated methyl group, means that at least one hydrogen atom in the substituent (methyl group) is replaced by deuterium.

[0063] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0064] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the resulting ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0065] The statement that two adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0066]

[0067] The statement that two adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0068]

[0069] Furthermore, the statement that two adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent bonds at the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0070]

[0071] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0072]

[0073] In Equation 1,

[0074] Substituent R1-R 10 At least one of them has the structure of Equation 2:

[0075]

[0076] And the substituent R1-R 10 The remaining elements, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or Unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0077] In Equation 2,

[0078] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-60 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-60 carbon atoms, or combinations thereof;

[0079] X1-X3 are selected from CR each time they appear, either the same or different. x Or N;

[0080] Y1 and Y5 are selected from CR each time they appear, either in the same or different ways. y1 Or N;

[0081] Y2-Y4 are selected from CR each time they appear, either in the same or different ways. y2 CR y3 Or N, and at least one of Y2-Y4 is CR y2 ;

[0082] Z is selected from C(R) each time it appears, either identically or differently. z )2, NR z , O, S or Se;

[0083] R x R y3 and R zEach time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0084] R y1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

[0085] R y2 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0086] Adjacent substituent R x R y1 R y3 They can be arbitrarily connected to form a loop;

[0087] Substituent R z They can be arbitrarily connected to form a loop;

[0088] * represents the position of the substituent of Formula 2 connected to Formula 1.

[0089] In this embodiment, the substituents R1 to R in Formula 1 10 At least one of them has a structure represented by Equation 2, and R1 to R 10 The remainder, each time appearing, is selected from the group consisting of the aforementioned substituents, either identically or differently. For example, when substituent R1 has the structure represented by Formula 2, then R1 to R... 10 The remainder, i.e., R2 to R 10 Each occurrence is either identical or different from the group consisting of the substituents described above. When substituents R1 and R6 have the structure represented by Formula 2, then R1 to R6... 10 The remainder, namely R2 to R5 and R7 to R10 Each time it appears, it is selected from the group consisting of the above-mentioned substituents, either in the same or different manner.

[0090] In this embodiment, the adjacent substituent R x R y1 R y3 The ability to arbitrarily connect to form a ring includes the following cases: one case is when multiple X1-X3 are selected from CR x When, adjacent R x They can be connected to form a ring, for example, X1 and X2 are selected from CR. x When, adjacent R x They can be connected to form a ring; X1 and X3 are selected from CR x When, adjacent R x They can be connected to form a ring; X2 and X3 are selected from CR x When, adjacent R x They can be connected to form a ring. When Y1 and Y5 are selected from CR y1 Y2-Y4 contains several selected from CR y3 When, the adjacent substituent R y3 It can connect to form a ring and / or adjacent substituents R y1 and R y3 They can be connected to form a ring, for example, Y2 and Y3 are both selected from CR. y3 At that time, these two R y3 They can be connected to form a ring; Y3 and Y4 are both selected from CR. y3 At that time, these two R y3 They can be connected to form a ring; Y1 is selected from CR y1 And Y2 is selected from CR y3 At this time R y1 and R y3 They can be connected to form a ring; Y5 is selected from CR y1 And Y4 is selected from CR y3 At this time R y1 and R y3 They can connect to form a ring. Another case is adjacent substituents R. x R y1 R y3 They do not connect to form a loop.

[0091] In this embodiment, "substituent R" z "Optionally linked to form a ring" can include one or more of the following cases: one case is for substituent R z There are cases where connections form loops, for example, when two or more R's exist simultaneously. z At that time, these R z There are cases where connections form a loop, such as R. zWhen they connect to form a ring, they create a helical or bridged ring structure. Another case is with substituent R... z They can also be left unconnected to form a loop.

[0092] The compounds disclosed in this invention have at least one (hetero)aryl substitution at the N-me or N-para position of one of the aryl groups in an aromatic amine, i.e., at least one of Y2-Y4 in Formula 2 of this invention. Applying these compounds to organic electroluminescent devices can improve device performance. Furthermore, (cyclo)alkyl substitution can be introduced at the N-ortho position of this aryl group, i.e., Y1 and / or Y5 in Formula 2 of this invention, to further improve device performance. When Y1 and / or Y5 are unsubstituted or (cyclo)alkyl substituted, the vapor deposition temperature is relatively mild while improving device performance. In contrast, if Y1 and / or Y5 are (hetero)aryl substituted, the vapor deposition temperature becomes higher, which is detrimental to the thermal stability requirements of the material in the industry.

[0093] According to one embodiment of the invention, substituents R1 to R... 10 There are at least two structures that have Equation 2.

[0094] According to one embodiment of the invention, substituents R1 to R... 10 There are two structures with Equation 2.

[0095] According to one embodiment of the present invention, the substituents R1 and R6 have the structure of Formula 2.

[0096] According to one embodiment of the present invention, the substituents R2, R4-R5, R7 and R9-R 10 The substituents R3 and R8 are selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms each time they appear.

[0097] According to one embodiment of the invention, L is selected, in the same or different ways, from single-bonded, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0098] According to one embodiment of the invention, L is selected, in the same or different ways, from a single bond, a substituted or unsubstituted aryl group having 6-12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-12 carbon atoms, or a combination thereof.

[0099] According to one embodiment of the present invention, L is a single bond.

[0100] According to one embodiment of the present invention, X1 to X3 are selected from CR each time they appear, either identically or differently. xY1 and Y5 are selected from CR each time they appear, either identically or differently. y1 Y2-Y4 are selected from CR each time they appear, either identically or differently. y2 and CR y3 And at least one of Y2-Y4 is CR y2 ;

[0101] R x and R y3 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0102] R y1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

[0103] R y2 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0104] Adjacent substituent R x R y1 R y3 They can be arbitrarily connected to form a ring.

[0105] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0106] According to one embodiment of the present invention, R x Each occurrence is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, isopropylphenyl, or combinations thereof, either identically or differently.

[0107] According to one embodiment of the present invention, Y2-Y4 are selected from CR each time they occur, either identically or differently. y2 and CR y3 And at least one of Y2-Y4 is CR y2 The rest are CR y3 .

[0108] In this embodiment, "at least one of Y2-Y4 is CR" y2 The rest are CR y3 "Including the following cases: when one of Y2-Y4 is CR" y2 At that time, the other two were CR. y3 When two of Y2-Y4 are CR y2 When, the remaining one is CR y3 ; or Y2-Y4 are all CR y2 For example, when Y2 is CR y2 When Y3 and Y4 are CR y3 When Y3 is CR y2 When Y2 and Y4 are CR y3 When Y4 is CR y2 When Y1 and Y3 are CR y3 When Y2 and Y4 are CR y2 When Y3 is CR y3 When Y3 and Y4 are CR y2 When Y2 is CR y3 Y2, Y3, and Y4 are all CR y2 .

[0109] According to one embodiment of the present invention, Y2-Y4 are selected from CR each time they occur, either identically or differently. y2 and CR y3 And one of Y2-Y4 is CR y2 The rest are CR y3 .

[0110] According to one embodiment of the present invention, R y3Each occurrence is the same or different of a group selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl group having 1-6 carbon atoms, substituted or unsubstituted aryl group having 6-12 carbon atoms, substituted or unsubstituted heteroaryl group having 3-12 carbon atoms, substituted or unsubstituted alkoxyl group having 3-6 carbon atoms, substituted or unsubstituted arylsilyl group having 6-12 carbon atoms, and combinations thereof.

[0111] According to one embodiment of the present invention, R y3 Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof.

[0112] According to one embodiment of the present invention, R y2 Each occurrence is the same or different of an aryl group having 6-24 carbon atoms, a heteroaryl group having 3-24 carbon atoms, or a combination thereof, either substituted or unsubstituted.

[0113] According to one embodiment of the present invention, R y2 Each occurrence is the same or different of an aryl group having 6-18 carbon atoms, a heteroaryl group having 3-18 carbon atoms, or a combination thereof, either substituted or unsubstituted.

[0114] According to one embodiment of the present invention, R y2 Each occurrence is the same or different of an aryl group having 6-12 carbon atoms, a heteroaryl group having 3-12 carbon atoms, or a combination thereof, either substituted or unsubstituted.

[0115] According to one embodiment of the present invention, R y2 Each occurrence may be the same or different of phenyl, 2-methylphenyl, 2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzothiophene, dibenzothiophene, dibenzoselenene, deuterated 2-methylphenyl, deuterated 2-ethylphenyl, deuterated 2-isopropylphenyl, deuterated 2-tert-butylphenyl, or combinations thereof.

[0116] According to one embodiment of the present invention, Y1 and Y5 are selected from CR each time they appear, either identically or differently. y1 And the R y1Each occurrence is the same or different of an alkyl group having 1-12 carbon atoms, a cycloalkyl group having 3-12 cyclic carbon atoms, or a combination thereof, either substituted or unsubstituted.

[0117] According to one embodiment of the present invention, Y1 and Y5 are selected from CR each time they appear, either identically or differently. y1 And the R y1 Each occurrence is the same or different of an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 3-6 cyclic carbon atoms, or a combination thereof, either substituted or unsubstituted.

[0118] According to one embodiment of the present invention, Y1 and Y5 are selected from CR each time they appear, either identically or differently. y1 And the R y1 Each occurrence may be the same or different of hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated cyclopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated neopentyl, deuterated cyclohexyl, or combinations thereof.

[0119] According to one embodiment of the present invention, Z is C(R) z )2, and the R z Each time it appears, it is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, or combinations thereof.

[0120] According to one embodiment of the present invention, R z Each time it appears, it is selected from hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, or combinations thereof, either identically or differently.

[0121] According to one embodiment of the present invention, R x R y1 and R y3 At least one of them is fluorine.

[0122] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds BD1 to BD1267, and the specific structures of compounds BD1 to BD1267 are shown in claim 13.

[0123] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0124] anode,

[0125] cathode,

[0126] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having Formula 1:

[0127]

[0128] In Equation 1,

[0129] Substituent R1-R 10 At least one of them has the structure of Equation 2:

[0130]

[0131] And replace base R l -R l0 The remaining elements, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or Unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0132] In Equation 2,

[0133] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-60 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-60 carbon atoms, or combinations thereof;

[0134] X1-X3 are CR x Or N;

[0135] Y1 and Y5 are selected from CR each time they appear, either in the same or different ways. y1 Or N;

[0136] Y2-Y4 are selected from CR each time they appear, either in the same or different ways. y2CR y3 Or N, and at least one of Y2-Y4 is CR y2 ;

[0137] Z is selected from C(R) each time it appears, either identically or differently. z )2, NR z , O, S or Se;

[0138] R x R y3 and R z Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0139] R y1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

[0140] R y2 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0141] Adjacent substituent R x R y1 R y3 They can be arbitrarily connected to form a loop;

[0142] Substituent R z They can be arbitrarily connected to form a loop;

[0143] * represents the position of the substituent of Formula 2 connected to Formula 1.

[0144] According to one embodiment of the present invention, the organic layer in the organic electroluminescent device comprises a light-emitting layer, wherein the light-emitting layer comprises a compound having Formula 1.

[0145] According to one embodiment of the present invention, the light-emitting layer further comprises a compound having Formula 3:

[0146]

[0147] In Equation 3,

[0148] R g1 to R g8 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0149] R g9 and R g10 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, either in the same or different manner.

[0150] According to one embodiment of the present invention, a compound formulation is also disclosed, which comprises a compound having the structure of Formula 1, wherein the specific structure of the compound is as shown in any of the foregoing embodiments.

[0151] Combination with other materials

[0152] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0153] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of host layers, transport layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0154] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0155] Material synthesis examples:

[0156] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0157] Synthesis Example 1: Synthesis of Compound BD32

[0158] first step:

[0159]

[0160] LDA (100 mL, 200 mmol) was placed in a 250 mL three-necked flask and stirred for half an hour under dry ice-ethanol conditions. Methyl isobutyrate (23 mL, 200 mmol) was added, and stirring was continued for another half hour. 1-Bromo-2-(bromomethyl)benzene (25 g, 100 mmol) was then added, and the mixture was filtered through diatomaceous earth. After concentration, crude intermediate 1 was obtained and directly proceeded to the next reaction step.

[0161] Step Two:

[0162]

[0163] Intermediate 1 (27 g, 100 mmol) and potassium hydroxide (56 g, 1 mol) were mixed, and 100 mL of water and 10 mL of methanol were added. The mixture was heated to 100 °C and reacted until the reaction was complete as detected by TLC. After cooling, the reaction was allowed to return to room temperature. Concentrated hydrochloric acid was added to adjust the pH of the system to acidic. The organic phase was extracted with ethyl acetate, and the organic phases were combined and concentrated.

[0164] The above product (27 g, 100 mmol) was dissolved in 200 mL of dichloromethane, purged with N2 gas, and one drop of DMF was added. Oxaloyl chloride (12.8 mL, 120 mmol) was then gradually added dropwise. After the system stopped producing bubbles, the reaction was transferred to an ice bath and stirred for half an hour. Aluminum trichloride (14.3 g, 108 mmol) was added in portions, and the reaction was monitored by TLC until completion. The product was purified by column chromatography, eluting with PE, to give a white solid intermediate 2 (22 g, 91.6 mmol, yield 85%).

[0165] Step 3:

[0166]

[0167] Intermediate 2 (22g, 99mmol) was dissolved in 300mL of methanol, stirred in an ice-water bath for half an hour, and NaBH4 was added in batches until the reaction was complete. The mixture was then filtered through diatomaceous earth and the filtrate was concentrated.

[0168] The above product was dissolved in dichloromethane, and Et3SiH (22.5 g, 198 mmol) was added. The mixture was stirred in an ice-water bath for half an hour, and TFA (34 g, 297 mmol) was gradually added dropwise. The mixture was concentrated and purified by column chromatography to obtain a colorless oily intermediate 3 (7.7 g, 34.4 mmol, yield 35%).

[0169] Step 4:

[0170]

[0171] Under nitrogen protection at room temperature, Pd2(dba3) (1 g, 1.1 mmol), intermediate 3 (5.1 g, 22.7 mmol), 4-methyl-[1,1′-biphenyl]-3-amine (5 g, 27.2 mmol), BINAP (1.4 g, 2.2 mmol), and tBuONa (4.7 g, 49.6 mmol) were added to xylene (100 mL), and the system was heated to 90 °C and reacted overnight. After the reaction was completed, the mixture was purified by column chromatography to give a white solid intermediate 4 (5.7 g, 17.4 mmol, yield 76%).

[0172] Step 5:

[0173]

[0174] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.6 g, 7.2 mmol), intermediate 4 (5.7 g, 17.4 mmol), Pd(OAc)2 (161 mg, 0.72 mmol), and tBu3PH were added. + BF4 - Xylene (20 mL) was added to 406 mg (1.4 mmol) and tBuONa (2.7 g, 28.2 mmol), and the system was heated to 100 °C until the reaction was complete. The mixture was then purified by column chromatography to give a yellow-green solid compound BD32 (1.2 g, 1.41 mmol, 20% yield). The product was identified as the target product with a molecular weight of 852.4.

[0175] Synthesis Example 2: Synthesis of Compound BD1141

[0176] first step

[0177]

[0178] 2-Bromo-4-iodo-1-methylbenzene (100 g, 337 mmol), phenylboronic acid (49 g, 404 mmol), Pd(PPh3)4 (7.8 g, 6.8 mmol), and K2CO3 (116 g, 843 mmol) were placed in a 1000 mL three-necked flask. Toluene (340 mL), THF (110 mL), and H2O (110 mL) were added to replace N2. The mixture was heated to 78 °C and reacted. After the reactants had completely reacted, the mixture was purified by column chromatography to give a colorless oily liquid intermediate 5 (80 g, 325 mmol, 97% yield).

[0179] Step 2

[0180]

[0181] Intermediate 5 (81 g, 329 mmol) and NBS (61 g, 345 mmol) were placed in a 2 L two-necked flask, and 1.3 L of acetonitrile was added to replace N2. The mixture was heated to 80 °C and stirred. Benzoyl peroxide (8 g, 33 mmol) was added in portions. The reaction was continued until the starting material was completely reacted, and the mixture was purified by column chromatography to give intermediate 6 (82 g, 253 mmol, 77% yield) as a white solid.

[0182] Step 3

[0183]

[0184] LDA (130 mL, 260 mmol) was placed in a 500 mL three-necked flask and stirred for half an hour under dry ice-ethanol conditions. Methyl isobutyrate (30 mL, 260 mmol) was added, and stirring continued for another half hour. Intermediate 6 (48 g, 148 mmol) was then added. The reaction was continued until the starting material was completely reacted, followed by column chromatography purification to obtain a pale yellow oily intermediate 7 (50 g, 145 mmol, 98% yield).

[0185] Step 4

[0186]

[0187] Intermediate 7 (78 g, 227 mmol) and KOH (88 g, 1.57 mol) were mixed, and H2O (230 mL) and methanol (23 mL) were added. The mixture was heated to 100 °C and reacted until the reaction was complete as detected by TLC. After cooling, the reaction was allowed to return to room temperature. Concentrated HCl was added to adjust the pH of the system to acidic. The precipitated white solid was filtered to obtain intermediate (71 g, 227 mmol).

[0188] The above intermediate (20 g, 60 mmol) was dissolved in 200 mL of dichloromethane. N2 was bubbled through the solution, and one drop of DMF was added. Oxaloyl chloride (30 mL, 60 mmol) was gradually added dropwise. Once no more bubbles were produced, the reaction was transferred to an ice-water bath and stirred for half an hour. Aluminum trichloride (8 g, 60 mmol) was added in portions, and the reaction was monitored by TLC until completion. The mixture was filtered through diatomaceous earth and concentrated. Column chromatography was used to separate the solid intermediate 8 (6 g, 18.8 mmol, yield 31%).

[0189] Step 5

[0190]

[0191] Intermediate 8 (18g, 57mmol) was dissolved in methanol (180mL), stirred in an ice-water bath for half an hour, and NaBH4 was added in batches until the reaction was complete. The mixture was then filtered through diatomaceous earth and the filtrate was concentrated.

[0192] The above product was dissolved in dichloromethane, and Et3SiH (12.7 g, 111 mmol) was added. The mixture was stirred in an ice-water bath for half an hour, and TFA (18 g, 155 mmol) was gradually added dropwise. The reaction was continued until the starting material was completely reacted. The mixture was then purified by column chromatography to obtain a colorless oily intermediate 9 (12 g, 39.9 mmol, yield 70%).

[0193] Step 6

[0194]

[0195] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 9 (6 g, 19.9 mmol), [1,1′-biphenyl]-3-amine (5.5 g, 30 mmol), and tBuONa (3.8 g, 39.8 mmol) were added to toluene (100 mL), and the system was heated to 120 °C for 2 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 10 (6.7 g, 16.4 mmol, yield 83%).

[0196] Step 7

[0197]

[0198] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.2 g, 6.1 mmol), intermediate 10 (5.5 g, 14 mmol), Pd(OAc)2 (68 mg, 0.3 mmol), and tBu3PH were added. + BF4 - 174 mg (0.6 mmol) and tBuONa (1.3 g, 14 mmol) were added to xylene (30 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to obtain a yellow-green solid BD1141 (5 g, 5.1 mmol, yield 84%). The product was identified as the target product with a molecular weight of 976.5.

[0199] Synthesis Example 3: Synthesis of Compound BD151

[0200] first step

[0201]

[0202] Intermediate 11 (50 g, 139 mmol) was added to a 1 L single-necked flask under nitrogen protection at -78 °C, followed by the addition of THF (400 mL), iPrMgCl (84 mL, 167 mmol), and then neopentaldehyde (36 g, 418 mmol) after half an hour. The mixture was then brought to room temperature. The reaction system was quenched with ammonium chloride, extracted with DCM, and the solvent was removed to obtain the intermediate. The intermediate was dissolved in DCM (1400 mL), and the system was cooled to 0 °C. Et3SiH (24 g, 213 mmol) was added, followed by the addition of TFA (36 g, 320 mmol) after half an hour. The mixture was then brought to room temperature. After the reaction was complete, the mixture was purified by column chromatography to obtain crude colorless oily intermediate 12 (36 g, 118 mmol, 85% yield).

[0203] Step 2

[0204]

[0205] Under nitrogen protection at room temperature, Pd(OAc)₂ (0.5 g, 2.2 mmol), intermediate 3 (10 g, 44.2 mmol), benzophenone imine (8.8 g, 48.7 mmol), dppf (2.4 g, 4.4 mmol), and tBuONa (8.8 g, 88.4 mmol) were added to a 250 mL single-necked flask, along with 100 mL of o-xylene. The system was heated to 90 °C and reacted overnight. The reaction solution was filtered through alkaline alumina and MgSO₄ and washed with Tol to remove the solvent, yielding a crude product. The crude product was then crystallized from PE to obtain the intermediate. The intermediate was dissolved in THF (30 mL), and HCl (10 mL) was added, and the reaction was allowed to proceed overnight. After the reaction was complete, the intermediate was purified by column chromatography to give a white solid intermediate 13 (6.2 g, 38.5 mmol, yield 87%).

[0206] Step 3

[0207]

[0208] Under nitrogen protection at room temperature, Pd2(dba)3 (0.5 g, 0.55 mmol), intermediate 12 (4 g, 13.2 mmol), intermediate 13 (2.6 g, 16.1 mmol), BINAP (685 mg, 1.1 mmol), and tBuONa (2.8 g, 29.1 mmol) were added to xylene (100 mL), and the system was heated to 90 °C and reacted overnight. After the reaction was completed, the mixture was purified by column chromatography to give a white solid intermediate 14 (4.5 g, 11.7 mmol, yield 88%).

[0209] Step 4

[0210]

[0211] Under nitrogen protection at room temperature, intermediate 14 (4 g, 10.4 mmol), 1,6-dibromopyrene (1.56 g, 4.35 mmol), Pd(OAc)2 (63 mg, 0.28 mmol), and tBu3PH were prepared. + BF4 - Xylene (30 mL) was added to 162 mg (0.56 mmol) and tBuONa (3.2 g, 33 mmol), and the system was heated to 100 °C until the reaction was complete. After the reaction was completed, the product was purified by column chromatography to give a yellow-green solid compound BD151 (1.1 g, 1.14 mmol, yield 26%). The product was identified as the target product with a molecular weight of 964.6.

[0212] Synthesis Example 4: Synthesis of Compound BD250

[0213] first step

[0214]

[0215] Under nitrogen protection at room temperature, palladium acetate (0.15 g, 0.67 mmol) and BINAP (0.83 g, 1.32 mmol) were added to toluene (70.0 mL). N2 was bubbled into the solution for 20 minutes, followed by the addition of intermediate 3 (5.0 g, 22.12 mmol), 5-fluoro-[1,1′-biphenyl]-3-amine (4.3 g, 23.23 mmol), and sodium tert-butoxide (6.4 g, 66.37 mmol). N2 was bubbled through the solution for another 10 minutes, and the mixture was heated to 110 °C for 4 hours. After the reaction was complete, the solution was purified by column chromatography to give a pale yellow oily intermediate 15 (3.8 g, 11.41 mmol, yield 52%).

[0216] Step 2

[0217]

[0218] Under nitrogen protection at room temperature, palladium acetate (35 mg, 0.16 mmol) and tBu3PH were added. + BF4 -Xylene (40.0 mL) was added to the solution (91 mg, 0.32 mmol). N2 was bubbled through the solution for 20 minutes, followed by the addition of 1,6-dibromopyrene (2 g, 5.56 mmol), intermediate 15 (3.8 g, 11.41 mmol), and sodium tert-butoxide (2.1 g, 22.2 mmol). N2 was bubbled through the solution for another 10 minutes, and the mixture was heated to 95 °C until the reaction was complete. After the reaction was complete, the product was purified by column chromatography to give a yellow solid compound BD250 (4 g, 4.64 mmol, 84% yield). The product was identified as the target product with a molecular weight of 860.4.

[0219] Synthesis Example 5: Synthesis of Compound BD441

[0220] first step

[0221]

[0222] 2-Methyl-5-fluoronitrobenzene (200 g, 1.29 mol) was dissolved in sulfuric acid at 0 °C under nitrogen protection, and NBS (252 g, 1.42 mol) was added in portions. The reaction was then brought to room temperature. After the reaction was complete, the product was purified by column chromatography to give a yellow liquid intermediate 16 (220 g, 936 mmol, yield 72%).

[0223] Step 2

[0224]

[0225] At room temperature, intermediate 16 (50 g, 213 mmol), Fe (35 g, 638 mmol), and NH4Cl (1.1 g, 21.3 mmol) were added to a 1 L single-necked flask, along with EtOH (400 mL) and water (100 mL). The system was heated to 90 °C for reaction. After the reaction was complete, the mixture was separated by column chromatography to give a pale yellow liquid intermediate 17 (41 g, 200 mmol, 94% yield).

[0226] Step 3

[0227]

[0228] Under nitrogen protection at room temperature, Pd(PPh3)4 (3.4 g, 3 mmol), intermediate 17 (31 g, 151 mmol), 2-methylphenylboronic acid (21 g, 159 mmol), and K2CO3 (52 g, 378 mmol) were added to a 1 L single-necked flask, along with toluene (400 mL), EtOH (200 mL), and water (100 mL). The system was heated to 90 °C and reacted overnight. After the reaction was complete, the mixture was separated by column chromatography to give a pale yellow solid intermediate 18 (27 g, 125 mmol, yield 83%).

[0229] Step 4

[0230]

[0231] Under nitrogen protection at room temperature, Pd2dba3 (0.5 g, 0.55 mmol), intermediate 18 (5.7 g, 26.5 mmol), intermediate 3 (5 g, 22 mmol), BINAP (685 mg, 1.1 mmol), and tBuONa (8.3 g, 86.9 mmol) were added to a 250 mL single-necked flask, followed by the addition of xylene (100 mL). The system was heated to 90 °C and reacted overnight. After the reaction was complete, the mixture was separated by column chromatography to give a white solid intermediate 19 (7.3 g, 20.2 mmol, 91% yield).

[0232] Step 5

[0233]

[0234] Under nitrogen protection at room temperature, intermediate 19 (7.3 g, 20 mmol), 1,6-dibromopyrene (3 g, 8.4 mmol), Pd(OAc)2 (63 mg, 0.28 mmol), and tBu3PH were mixed. + BF4 - Xylene (30 mL) was added to 162 mg (0.56 mmol) and tBuONa (3.2 g, 33 mmol), and the system was heated to 100 °C until the reaction was complete. After the reaction was completed, the product was separated by column chromatography to obtain a yellow-green solid BD441 (1.2 g, 1.30 mmol, yield 15.4%). The product was identified as the target product with a molecular weight of 916.5.

[0235] Synthesis Example 6: Synthesis of Compound BD1148

[0236] first step

[0237]

[0238] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 9 (6 g, 19.9 mmol), 4-methyl-[1,1′-biphenyl]-3-amine (5.5 g, 30 mmol), and t-BuONa (3.8 g, 39.8 mmol) were added to toluene (100 mL), and the system was heated to 120 °C for 2 h. After the reaction was completed, the product was purified by column chromatography to give a white solid intermediate 20 (6.7 g, 16.4 mmol, yield 82.7%).

[0239] Step 2

[0240]

[0241] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.38 g, 6.6 mmol), intermediate 6 (6.2 g, 15.2 mmol), Pd(OAc)2 (74 mg, 0.33 mmol), and t-Bu3P·H were added. + BF4 - 191 mg (0.66 mmol) and t-BuONa (1.46 g, 15.2 mmol) were added to xylene (33 mL), and the system was heated to 95 °C. After the reaction was complete, the product compound BD1148 (6 g, 5.97 mmol, 90% yield) was purified by column chromatography. The product was identified as the target product with a molecular weight of 1004.5.

[0242] Synthesis Example 7: Synthesis of Compound BD257

[0243] first step

[0244]

[0245] Under nitrogen protection at room temperature, Pd(PPh3)4 (3.4 g, 3 mmol), intermediate 17 (55 g, 268 mmol), phenylboronic acid (50 g, 282 mmol), and K2CO3 (92 g, 670 mmol) were added to a 1 L single-necked flask, along with Tol (400 mL), EtOH (200 mL), and water (100 mL). The system was heated to 90 °C and reacted overnight. After the reaction was complete, column chromatography was used to separate the intermediate 21 (42 g, 208 mmol, yield 77%) into a pale yellow solid.

[0246] Step 2

[0247]

[0248] Under nitrogen protection at room temperature, Pd2(dba)3 (0.5 g, 0.55 mmol), intermediate 21 (5.4 g, 26.2 mmol), intermediate 3 (5 g, 22 mmol), BINAP (685 mg, 1.1 mmol), and tBuONa (8.3 g, 86.9 mmol) were added to a 250 mL single-necked flask, followed by 100 mL of xylene. The system was heated to 90 °C and reacted overnight. After the reaction was complete, the mixture was separated by column chromatography to give a white solid intermediate 22 (5.8 g, 16.7 mmol, 76% yield).

[0249] Step 3

[0250]

[0251] Under nitrogen protection at room temperature, intermediate 22 (5.8 g, 16.7 mmol), 1,6-dibromopyrene (2.5 g, 7.0 mmol), Pd(OAc)2 (63 mg, 0.28 mmol), and tBu3PH were prepared. + BF4 - Xylene (30 mL) and tBuONa (162 mg, 0.56 mmol) were added to a 100 mL single-necked flask, followed by 30 mL of xylene. The system was heated to 100 °C until the reaction was complete. After the reaction was complete, the product was separated by column chromatography to obtain a yellow-green solid compound BD257 (1.4 g, 1.57 mmol, yield 22%). The product was identified as the target product with a molecular weight of 888.4.

[0252] Synthesis Example 8: Synthesis of Compound BD261

[0253] first step

[0254]

[0255] 1-Bromo-2-fluoro-4-methylbenzene (94.5 g, 0.5 mol) was dissolved in 1 L of concentrated sulfuric acid at 0 °C, and concentrated nitric acid (37.8 g, 0.6 mol) was slowly added dropwise. The reaction was heated to room temperature and stirred overnight. After the reaction was complete, a large amount of ice was added, and the mixture was extracted three times with dichloromethane. The organic phases were combined and separated by column chromatography to give intermediate 23 (93.6 g, 0.4 mol, 80% yield).

[0256] Step 2

[0257]

[0258] Under nitrogen protection, intermediate 23 (26.8 g, 114.6 mmol), phenylboronic acid (21 g, 172 mmol), tetrakis(triphenylphosphine)palladium (6.7 g, 5.74 mmol), K2CO3 (47.5 g, 344 mmol), toluene (240 mL), and water (60 mL) were added to a dry 1 L three-necked flask. Nitrogen was purged three times, the temperature was raised to 100 °C, and the reaction was stopped overnight. The mixture was separated by column chromatography to obtain intermediate 24 (23.1 g, 100 mmol, yield 89%).

[0259] Step 3

[0260]

[0261] Intermediate 24 (23.1 g, 100 mmol) was dissolved in 1 L of ethanol, and 100 mL of saturated ammonium chloride aqueous solution was added. After adding reduced iron powder (16.8 g, 300 mmol), the reaction mixture was heated to 80 °C and stirred for 3 hours. After cooling to room temperature, the reaction solution was filtered through diatomaceous earth, most of the ethanol was evaporated, water was added, and the mixture was extracted three times with dichloromethane. The organic phases were combined, and intermediate 25 (19 g, 95 mmol, 95% yield) was obtained by column chromatography.

[0262] Step 4

[0263]

[0264] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 25 (6.03 g, 30 mmol), intermediate 3 (4.48 g, 19.9 mmol), and tBuONa (3.8 g, 39.8 mmol) were added to toluene (200 mL), and the system was heated to 120 °C for 2 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 26 (5.52 g, 16 mmol, yield 53%).

[0265] Step 5

[0266]

[0267] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.2 g, 6.1 mmol), intermediate 26 (5.52 g, 16 mmol), Pd(OAc)2 (68 mg, 0.3 mmol), and tBu3PH were added. + BF4 - 174 mg (0.6 mmol) and t-BuONa (1.3 g, 14 mmol) were added to xylene (30 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to give a yellow-green solid BD261 (2 g, 2.25 mmol, yield 37%). The product was identified as the target product with a molecular weight of 888.4.

[0268] Synthesis Example 9: Synthesis of Compound BD177

[0269] first step

[0270]

[0271] At room temperature, 120 g (634.9 mmol) of 2-bromo-4-fluoro-1-methylbenzene and 8 g (33 mmol) of benzoyl peroxide were added to 1.5 L of acetonitrile, followed by the addition of NBS (124 g, 698.4 mmol) in portions. The mixture was heated to 80 °C and stirred. After the reaction was complete, the mixture was purified by column chromatography to give intermediate 27 (136 g, 507.46 mmol, 80% yield) as a white solid.

[0272] Step 2

[0273]

[0274] LDA (2M, 380 mmol) was added to tetrahydrofuran (300 mL), and the mixture was stirred under dry ice-ethanol for half an hour. Methyl isobutyrate (87 mL, 761.19 mmol) was added dropwise, and stirring continued for another half hour. Then, intermediate 27 (136.0 g, 507.46 mmol / L in 200 mL THF) was added dropwise. After the reaction was complete, the mixture was quenched with water, extracted with ethyl acetate, and the organic phase was concentrated and dissolved in methanol (800 mL). An aqueous solution of KOH (78 g, 1402 mmol / L in 400 mL H₂O) was added, and the mixture was heated to 40 °C. After the reaction was complete, the mixture was purified by column chromatography to give a light yellow oily intermediate 28 (116 g, 415.77 mmol, yield 82%).

[0275] Step 3

[0276]

[0277] Under nitrogen protection at 0°C, intermediate 28 (116 g, 415.77 mmol) was dissolved in 500 mL of dichloromethane, N,N-dimethylformamide (0.5 mL) was added, and thionyl chloride (32 mL, 436.56 mmol) was gradually added dropwise. The reaction was carried out at 0°C for 2 h, and then concentrated. The concentrated system was added to 500 mL of dichloromethane, and aluminum trichloride (55 g, 415.77 mmol) was added at 0°C. The reaction was then brought back to room temperature. After the reaction was completed, water was added to quench the reaction, and the mixture was separated. The organic phase was concentrated and purified by column chromatography to obtain transparent oil intermediate 29 (40.0 g, 155.64 mmol, yield 37%).

[0278] Step 4

[0279]

[0280] Under nitrogen protection at 0°C, intermediate 29 (55 g, 214.0 mmol) was dissolved in 500 mL of methanol, and sodium borohydride (9.7 g, 256.8 mmol) was added in portions until the reaction was complete. The mixture was then filtered through diatomaceous earth and the filtrate was concentrated.

[0281] The above product was dissolved in dichloromethane, and triethylsilane (62.0 g, 470.0 mmol) was added. The mixture was stirred in an ice-water bath for half an hour, and trifluoroacetic acid (60 ml, 810.8 mmol) was gradually added dropwise. The mixture was then reacted at room temperature for 72 h and concentrated. The product was purified by column chromatography to give a pale yellow oily intermediate 30 (7.0 g, 28.92 mmol, yield 14%).

[0282] Step 5

[0283]

[0284] Under nitrogen protection at room temperature, palladium acetate (148.0 mg, 0.67 mmol), BINAP (826.0 mg, 1.32 mmol), 4-methyl-[1,1′-biphenyl]-3-amine (4.3 g, 23.23 mmol), intermediate 30 (5.0 g, 22.12 mmol), and sodium tert-butoxide (6.4 g, 66.37 mmol) were added to a 250 mL single-necked flask, followed by 100 mL of toluene. The system was heated to 120 °C and reacted for 2 h. After the reaction was complete, the mixture was purified by column chromatography to give a pale yellow oil intermediate 31 (3.8 g, 11.41 mmol, yield 52%).

[0285] Step 6

[0286]

[0287] Under nitrogen protection at room temperature, palladium acetate (35 mg, 0.16 mmol) and tBu3PH were added. + BF4 - (91 mg, 0.32 mmol) was added to xylene (40.0 mL). N2 was bubbled through this solution for 20 minutes, followed by the addition of 1,6-dibromopyrene (2.0 g, 5.56 mmol), intermediate 31 (3.8 g, 11.41 mmol), and sodium tert-butoxide (2.1 g, 22.2 mmol). N2 was bubbled through the solution for another 10 minutes, and the system was heated to 95 °C. After the reaction was complete, the product was purified by column chromatography to give a yellow-green solid compound BD177 (2.0 g, 2.25 mmol, 40% yield). The product was identified as the target product with a molecular weight of 888.4.

[0288] Synthesis Example 10: Synthesis of Compound BD393

[0289] first step

[0290]

[0291] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 3 (5 g, 22.7 mmol), 2′-4-methyl-[1,1′-biphenyl]-3-amine (5.4 g, 27.2 mmol), and tBuONa (4.3 g, 45 mmol) were added to toluene (100 mL), and the system was heated to 120 °C for 2 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 32 (5.4 g, 15.8 mmol, yield 71%).

[0292] Step 2

[0293]

[0294] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2 g, 6.28 mmol), intermediate 32 (4.9 g, 14.45 mmol), Pd(OAc)2 (70 mg, 0.31 mmol), and tBu3PH were added. + BF4 - 180 mg (0.62 mmol) and tBuONa (1.38 g, 14.45 mmol) were added to xylene (30 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to obtain a yellow-green solid BD393 (4 g, 4.54 mmol, yield 72%). The product was identified as the target product with a molecular weight of 880.5.

[0295] Synthesis Example 11: Synthesis of Compound BD103

[0296] first step

[0297]

[0298] Under nitrogen protection, 1-isopropyl-2-nitrobenzene (25 g, 151.3 mmol), TFA (500 mL), and concentrated sulfuric acid (50 mL) were added to a dry 1 L single-necked flask. After dissolution, the mixture was cooled to 0 °C, and NBS (27 g, 151.3 mmol) was added in portions. The mixture was allowed to return to room temperature, and the reaction was allowed to proceed overnight until complete. The reaction was separated by column chromatography to give intermediate 33 (28 g, 114.6 mmol, yield 75.7%).

[0299] Step 2

[0300]

[0301] Under nitrogen protection, intermediate 33 (28 g, 114.6 mmol), phenylboronic acid (21 g, 172 mmol), tetraphenylphosphine palladium (6.7 g, 5.74 mmol), K2CO3 (47.5 g, 344 mmol), dioxane (240 mL), and water (60 mL) were added to a dry 1 L three-necked flask. Nitrogen was purged three times, the temperature was raised to 100 °C, and the reaction was stopped after overnight. The mixture was separated by column chromatography to obtain intermediate 34 (25 g, 102.8 mmol, yield 89.6%).

[0302] Step 3

[0303]

[0304] Under nitrogen protection, intermediate 34 (25 g, 100 mmol), hydrazine hydrate (6 g), FeCl3 (2.5 g), activated carbon (2.5 g), toluene (275 mL), and ethanol (275 mL) were added to a dry 1 L three-necked flask. The mixture was heated to 90 °C and refluxed, with hydrazine hydrate (6 mL) added every hour and monitored by TLC. A total of 42 mL of hydrazine hydrate was added, and the reaction was completed after 24 h. The mixture was cooled, filtered through diatomaceous earth, washed with DCM, and extracted and concentrated. Column chromatography was used to separate the target product intermediate 35 (18 g, 84.5 mmol, yield 84.5%).

[0305] Step 4

[0306]

[0307] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 35 (6.33 g, 30 mmol), intermediate 3 (4.48 g, 19.9 mmol), and tBuONa (3.8 g, 39.8 mmol) were added to toluene (200 mL), and the system was heated to 120 °C and reacted for 2 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 36 (5.8 g, 16.4 mmol, yield 83%).

[0308] Step 5

[0309]

[0310] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.2 g, 6.1 mmol), intermediate 36 (5.8 g, 16.4 mmol), Pd(OAc)2 (68 mg, 0.3 mmol), and tBu3PH were added. + BF4 -174 mg (0.6 mmol) and tBuONa (1.3 g, 14 mmol) were added to xylene (30 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to obtain a yellow-green solid BD103 (4.6 g, 5.1 mmol, yield 84%). The product was identified as the target product with a molecular weight of 908.5.

[0311] Synthesis Example 12: Synthesis of Compound BD25

[0312] first step

[0313]

[0314] Dissolve 100 g of 4-bromo-1-indanone in methanol (180 mL), stir in an ice-water bath for half an hour, add NaBH4 (22.8 g, 600 mol) in portions until the reaction is complete, filter with diatomaceous earth, and concentrate the filtrate.

[0315] The above product was dissolved in dichloromethane, and Et3SiH (67.4 g, 592 mmol) was added. The mixture was stirred in an ice-water bath for half an hour, and TFA (103 g, 888 mmol) was gradually added dropwise. The reaction was continued until the starting material was completely reacted. The mixture was then purified by column chromatography to obtain a colorless oily intermediate 37 (44 g, 225 mmol, yield 47%).

[0316] Step 2

[0317]

[0318] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 37 (4 g, 20.5 mmol), [1,1'-biphenyl]-3-amine (4.5 g, 24.6 mmol), and tBuONa (3.9 g, 41 mmol) were added to toluene (100 mL), and the system was heated to 120 °C for 2 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 38 (6.2 g, 20.15 mmol, yield 98%).

[0319] Step 3

[0320]

[0321] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.5 g, 7 mmol), intermediate 38 (5.5 g, 16.2 mmol), Pd(OAc)2 (78 mg, 0.35 mmol), and tBu3PH were added. + BF4 -200 mg (0.7 mmol) and tBuONa (1.6 g, 16.2 mmol) were added to xylene (35 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to give a yellow-green solid BD25 (4 g, 5.1 mmol, yield 69%). The product was identified as the target product with a molecular weight of 796.4.

[0322] Synthetic Comparative Example 1: Synthesis of Comparative Compound A

[0323] first step:

[0324]

[0325] Under nitrogen protection at room temperature, Pd2(dba3) (1 g, 1.1 mmol), intermediate 3 (5 g, 22.7 mmol), 2-methylaniline (2.9 g, 27.2 mmol), BINAP (1.4 g, 2.2 mmol), and t-BuONa (4.3 g, 45.4 mmol) were added to xylene (100 mL), and the system was heated to 90 °C and reacted overnight. After the reaction was completed, the mixture was purified by column chromatography to give a white solid intermediate 39 (4 g, 17.4 mmol, yield 76%).

[0326] Step 2

[0327]

[0328] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.5 g, 7.0 mmol), intermediate 39 (4 g, 16.2 mmol), Pd(OAc)2 (78 mg, 0.35 mmol), and tBu3PH were added. + BF4 - 200 mg (0.7 mmol) and t-BuONa (1.6 g, 16.2 mmol) were added to xylene (35 mL), and the system was heated to 95 °C until the reaction was complete. The mixture was then purified by column chromatography to give a yellow-green solid compound A (3.4 g, 4.86 mmol, 69%). The product was identified as the target product with a molecular weight of 700.4.

[0329] Comparative Example 2: Synthesis of Comparative Compound B

[0330] first step:

[0331]

[0332] Under nitrogen protection at room temperature, Pd2(dba)3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 9 (6 g, 19.9 mmol), aniline (2.79 g, 30 mmol), and tBuONa (3.8 g, 39.8 mmol) were added to toluene (100 mL), and the system was heated to 120 °C for 3 h. After the reaction was completed, the mixture was purified by column chromatography to give a colorless oily intermediate 40 (5.3 g, 16.9 mmol, yield 85%).

[0333] Step Two:

[0334]

[0335] Under nitrogen protection at room temperature, 1,6-dibromopyrene (2.38 g, 6.6 mmol), intermediate 40 (4.76 g, 15.2 mmol), Pd(OAc)2 (74 mg, 0.33 mmol), t-Bu3P·HBF4 (191 mg, 0.66 mmol), and t-BuONa (1.46 g, 15.2 mmol) were added to xylene (30 mL), and the system was heated to 95 °C. After the reaction was complete, the mixture was purified by column chromatography to obtain a yellow-green solid, comparative compound B (4.68 g, 5.67 mmol, 86%). The product was identified as the target product with a molecular weight of 824.4.

[0336] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0337] Device Example 1

[0338] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8Under the condition of Turbo evaporation, the ITO anode was sequentially deposited by thermal vacuum evaporation at a rate of 0.2–2 Å / s. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound EB was used as the electron blocking layer (EBL). Then, compound BD32 was doped in compound BH and co-deposited as the light-emitting layer (EML). Compound HB was used as the hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer, and a 120 nm thick layer of aluminum was deposited as the cathode. The device was then transferred back to the glove box and sealed with a glass cover and desiccant to complete the device.

[0339] Device Example 2

[0340] The implementation method of Device Example 2 is the same as that of Device Example 1, except that compound BD1141 is used instead of compound BD32 in the light-emitting layer (EML).

[0341] Device Example 3

[0342] The implementation method of Device Example 3 is the same as that of Device Example 1, except that compound BD32 is replaced by compound BD151 in the light-emitting layer (EML).

[0343] Device Example 4

[0344] The implementation of Device Example 4 is the same as that of Device Example 1, except that compound BD1148 is used instead of compound BD32 in the light-emitting layer (EML).

[0345] Device Example 5

[0346] The implementation of Device Example 5 is the same as that of Device Example 1, except that compound BD32 is replaced by compound BD250 in the light-emitting layer (EML).

[0347] Device Example 6

[0348] The implementation of Device Example 6 is the same as that of Device Example 1, except that compound BD32 is replaced by compound BD441 in the light-emitting layer (EML).

[0349] Device Comparison Example 1

[0350] The implementation of Comparative Example 1 is the same as that of Example 1, except that compound A is used instead of compound BD32 in the light-emitting layer (EML).

[0351] Device Comparison Example 2

[0352] The implementation of Comparative Example 2 is the same as that of Example 1, except that compound B is used instead of compound BD32 in the light-emitting layer (EML).

[0353] The detailed structure and thickness of the device layers are shown in Table 1. The layers use more than one material and are obtained by doping different compounds in the specified weight ratios.

[0354] Table 1. Device structures of the device embodiments and comparative examples.

[0355]

[0356] The material structure used in the device is shown below:

[0357]

[0358]

[0359] The IVL of all embodiment and comparative devices was measured at different current densities and voltages, while the deposition temperature was also measured. At a constant current of 1000 cd / m², the IVL was measured. 2 Under these conditions, the external quantum efficiency (EQE) and maximum emission wavelength (λ) are measured. max ), half-width at half-maximum (FWHM) and CIE data.

[0360] Table 2 Device data for Example 1, Example 2, Comparative Example 1, and Comparative Example 2

[0361] Part Number CIE(x,y) λmax(nm) FWHM(nm) EQE (%) Example 1 0.135,0.117 461 29.7 9.11 Example 2 0.133,0.129 463 30.5 9.02 Comparative Example 1 0.136,0.127 461 31.7 8.43 Comparative Example 2 0.133,0.133 463 30.5 8.65

[0362] discuss:

[0363] Table 2 shows the device data for Example 1, Example 2, Comparative Example 1, and Comparative Example 2. Compared with Comparative Example 1, Example 1 shows that when one of the aryl groups of the aromatic amine is a biaryl group, the EQE is increased by nearly 8.07% (9.11 vs. 8.43), and the full width at half maximum (FWHM) is narrowed by 2 nm (29.7 nm vs. 31.7 nm), effectively improving device performance.

[0364] Furthermore, compared to Comparative Example 2, Example 2 showed an EQE increase of approximately 4.28%, while the full width at half maximum (FWHM) and maximum emission wavelength remained unchanged. This demonstrates that Example 2, compared to Comparative Example 2, shows that when one aryl group of the aromatic amine is a biaryl group, an improvement in EQE can be achieved, effectively increasing the blue emission performance.

[0365] Table 3 Device data for Examples 3 and 4

[0366] Part Number CIE(x,y) λmax(nm) FWHM(nm) EQE (%) Example 3 0.133,0.120 462 28.5 9.48 Example 4 0.135,0.118 461 29.7 9.12

[0367] discuss:

[0368] Table 3 shows the device data for Examples 3 and 4. In Example 4, a methyl group was further introduced at the N-ortho position of the aromatic amine. Compared to Example 2, where no substituent was present at the N-ortho position of the aromatic amine, the EQE was improved (9.12 vs. 9.02), the full width at half maximum (FWHM) was narrowed (29.7 nm vs. 30.5 nm), and the maximum emission wavelength also underwent a blue shift (461 nm vs. 463 nm). The results indicate that, based on the premise that one aryl group of the aromatic amine is a biaryl group, simultaneously introducing an alkyl substituent at the N-ortho position of the aryl group can further improve the blue emission performance.

[0369] In Example 3, a neopentyl group was further introduced at the N-ortho position of the aromatic amine. Compared to the introduction of a methyl group at the N-ortho position in Example 1, the addition of the ortho substituent and the gradual increase in EQE (9.48 vs. 9.11) with increasing molecular size of the ortho substituent resulted in a narrower half-width at half-maximum (28.5 nm vs. 29.7 nm). Compared to Comparative Example 1, both EQE and half-width at half-maximum were improved. The results indicate that, based on the dual structure of the aromatic amine with a benzo5-membered ring and a biaryl substituent, the simultaneous introduction of a substituent at the N-ortho position can further enhance the blue luminescence performance, and this effect increases with the increase in molecular size of the N-ortho substituent.

[0370] Table 4 Device data for Examples 5 and 6

[0371] Part Number CIE(x,y) λmax(nm) FWHM(nm) EQE (%) Example 5 0.139,0.089 456 31.3 8.99 Example 6 0.140,0.089 455 29.4 8.71

[0372] discuss:

[0373] Table 3 shows the device data for Examples 5 and 6. In Examples 5 and 6, fluorine substitution was introduced at the N-meta position of the aryl group in the aromatic amine. Compared to Examples 2 and 1 without fluorine substitution, the maximum emission wavelengths were blue-shifted by 7 nm (456 nm vs. 463 nm) and 6 nm (455 nm vs. 461 nm), respectively. The results indicate that, based on the dual structure of the aromatic amine with a benzo5-membered ring and biaryl substituents, the introduction of fluorine substitution can achieve a blue shift in the maximum emission wavelength, resulting in deep blue luminescence.

[0374] Table 5 Device Examples Evaporation Temperatures of the Compounds of the Present Invention

[0375] Compound BD31 BD151 BD441 BD250 Evaporation temperature / ℃ 228.5 230.0 236.0 209.0

[0376] The vapor deposition temperature data of the compounds of the present invention in the device embodiments are shown in Table 5. These vapor deposition temperatures are achieved at a vacuum degree of approximately 10... -8 The material was deposited at a rate of 0.04 Å / s. The compounds disclosed in this invention improve device performance while maintaining a relatively mild deposition temperature, which is beneficial for meeting the thermal stability requirements of the industry.

[0377] In summary, in aromatic amine-substituted pyrene compounds, one substituent of the aromatic amine is a substituted or unsubstituted ortho-(hetero)aryl pentane ring structure, and the other is a substituted or unsubstituted bi(hetero)aryl group, especially a substituted or unsubstituted biaryl group with no more than two aryl (phenyl) groups. The novel compounds obtained by combining such structures, when applied to organic electroluminescent devices, can achieve a bluer emission wavelength, higher EQE, and narrower half-width at half-maximum, thereby improving the overall performance of the device. Furthermore, introducing fluorine substitution or an N-ortho substituent into the other (hetero)aryl group can further enhance the blue emission performance. The compounds disclosed in this invention improve device performance while also having a relatively mild material evaporation temperature, which is beneficial for the thermal stability requirements of the industry.

[0378] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A compound having formula 1: in, In formula 1, The substituents R1 and R6 have the structure of Formula 2: and the substituents R2, R4-R5, R7 and R9-R 10 is hydrogen, deuterium, and the substituents R3 and R8 are each selected, identically or differently, from hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Among them, in formula 2, L is selected from a single bond; X1 and X3 are selected from CR x , and R x is selected, identically or differently at each occurrence, from hydrogen or deuterium; X2 Selected from CR x , and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl having 6 carbon atoms, and combinations thereof; One of Y1 or Y5 is selected from CR y1 , the other of Y1 or Y5 is selected from hydrogen or deuterium; One of Y2 or Y4 is CR y2 , the rest of Y2 to Y4 is CR y3 ; Z is selected from C(R z )2; R y3 is selected, identically or differently on each occurrence, from hydrogen, deuterium or halogen; R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; R y1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; R y2 is selected from substituted or unsubstituted aryl groups having 6 carbon atoms; * represents the position where the substituent having the structure of Formula 2 is attached to Formula 1; Any one of the alkyl and aryl groups is unsubstituted or substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof.

2. The compound of claim 1, wherein the substituents R2, R4-R5, R7 and R9-R 10 is a hydrogen atom, and the substituents R3 and R8 are each identically or differently selected from hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

3. The compound as claimed in claim 1, wherein one of Y2 or Y4 is CR y2 , the rest of Y2 to Y4 is CR y3 ; The R y3 is selected, identically or differently at each occurrence, from hydrogen, deuterium or fluorine; The R y2 is selected from unsubstituted aryl groups having 6 carbon atoms.

4. The compound of claim 1, wherein Y1 or Y5 is selected from CR y1 , and the R y1 Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, or a combination thereof.

5. The compound as claimed in claim 4, wherein R y1 Each occurrence is identically or differently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, or a combination thereof.

6. The compound of claim 1, wherein R z is selected from unsubstituted alkyl groups having 1 to 20 carbon atoms.

7. The compound of claim 1, wherein R z Each occurrence is identically or differently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, or a combination thereof.

8. The compound of claim 1, wherein the compound is selected from the group consisting of:

9. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 8. 10 . The organic electroluminescent device as claimed in claim 9 , wherein the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises the compound of Formula 1.

11. The organic electroluminescent device according to claim 10, wherein the light-emitting layer further comprises a compound having Formula 3: in, In formula 3, R g1 To R g8 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; R g9 and R g10 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

12. A composition comprising the compound of any one of claims 1-8.

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