Organic electroluminescent material and device thereof

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound having a structure of Formula 1, which can be used as a light-emitting material in an electroluminescent device. These novel compounds can provide better device performance, such as effectively reducing voltage, providing higher efficiency and longer lifetime, etc. A compound combination is also disclosed.

Description

TECHNICAL FIELD

[0001] The present application relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound having the structure of Formula 1 and organic electroluminescent devices and compound combinations comprising the same. BACKGROUND

[0002] Organic electronic devices include, but are not limited to, the following kinds: 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 photoreceptors, organic field-quench devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke at Kodak reported a two-layer organic electroluminescent device that included an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). Upon biasing the device, green light emitted from the device. 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 light emitting layers between the cathode and anode. Since OLEDs are self-emitting solid-state devices, they offer tremendous potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them well suited for particular applications, such as on flexible substrates.

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

[0005] OLEDs can also be categorized into small molecule and polymer OLEDs according to the form of materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be quite large as long as it has a well-defined structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the materials can be dissolved or dispersed in solvents.

[0007] The emission color of OLEDs can be achieved by light-emitting material structure design. OLEDs can include one or multiple light-emitting layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually employ a hybrid strategy, using blue fluorescent and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have more saturated emission spectrum, higher efficiency, and longer device lifetime.

[0008] CN110627822A discloses the following compounds and an organic electroluminescent device comprising the compounds:

[0009] It further discloses compounds of the following formula: Specific compounds. The application focuses on the substituents on the boron-nitrogen heterocyclic skeleton, and the disclosed specific structures are mostly alkyl, cycloalkyl, etc. The application does not disclose or teach that the substituents on the carbazole ring can be connected to form a ring, and does not disclose or teach the influence of the compounds in which the substituents on the carbazole ring are connected to form a ring on the performance of the device.

[0010] EP3712158A1 discloses the following compounds and organic electroluminescent devices comprising the compounds: wherein V, T are selected from single bond, CRR, NR, SiRR, O, S, etc., and it further discloses compounds of the following general formula: The application focuses on the necessity of connecting a nitrogen heterocyclic ring to the boron-nitrogen heterocyclic skeleton, and does not disclose or teach that the substituents on the carbazole ring can be connected to form a ring, and does not disclose or teach the influence of the compounds in which the substituents on the carbazole ring are connected to form a ring on the performance of the device.

[0011] CN112236434A discloses the following compounds and organic electroluminescent devices comprising the compounds: wherein Ar1-Ar4 are each independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, etc., and A1-A2 are each independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or bonded to each other to form a substituted or unsubstituted ring, etc. It further discloses compounds of the following formula: The application focuses on the specific substituents of Ar1-Ar4 and A1-A2 on the boron-nitrogen heterocyclic skeleton, and does not disclose or teach that the substituents on the carbazole ring can be connected to form a ring, and does not disclose or teach the influence of the compounds in which the substituents on the carbazole ring are connected to form a ring on the performance of the device.

[0012] A series of compounds containing boron-nitrogen heterocyclic skeleton are disclosed in these documents, but these materials still need to be further developed to obtain higher device performance in OLEDs. SUMMARY

[0013] The present application aims to provide a series of compounds with the structure of formula 1 to solve at least part of the above problems. The compounds can be used as light-emitting materials in organic electroluminescent devices. These novel compounds can provide better device performance.

[0014] According to one embodiment of the present application, a compound having the structure of Formula 1 is disclosed:

[0015]

[0016] wherein each of ring A, ring C, ring D, ring E is independently selected from an unsaturated carbocyclic ring having 5-30 carbon atoms or an unsaturated heterocyclic ring having 3-30 carbon atoms;

[0017] X1is selected from CR a R a , NR a , SiR a R a , O, S, Se, PR a or BR a ;

[0018] X2is selected from CR a , N, SiR a or B;

[0019] a, b, c, d are each independently selected from C, CR, N or NR;

[0020] at least one of a and b or c and d are connected by a single bond to form a ring; and, when a, b are connected by a single bond to form a ring, two R” are connected to form a ring; when c, d are connected by a single bond to form a ring, two R’ are connected to form a ring;

[0021] R is the same or different at each occurrence and represents mono-substitution, poly-substitution or no substitution;

[0022] R, R a are each the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylate, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0023] R', R" are the same or different at each occurrence selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3 to 20 ring atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilicon having from 6 to 20 carbon atoms, substituted or unsubstituted amino having from 0 to 20 carbon atoms, hydroxy, mercapto, and combinations thereof;

[0024] adjacent substituents R, R', R", R a may optionally be linked to form a ring.

[0025] According to another embodiment of the present application, an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound having the structure of Formula 1 is also disclosed.

[0026] According to another embodiment of the present application, a compound combination comprising the compound having the structure of Formula 1 is also disclosed.

[0027] The novel compounds having the structure of Formula 1 disclosed in the present application can be used as light-emitting materials in electroluminescent devices. These novel compounds can provide better device performance, such as effectively reducing voltage, providing higher efficiency and longer lifetime, etc. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 is a schematic diagram of an organic light emitting device that can contain the compounds and compound combinations disclosed herein.

[0029] Figure 2 is another schematic diagram of an organic light emitting device that can contain the compounds and compound combinations disclosed herein. DETAILED DESCRIPTION

[0030] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Figure 1An organic light emitting device 100 is schematically, non-limitingly illustrated. The figures are not necessarily drawn to scale and some layer structures in the figures can also be omitted as desired. The device 100 can 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. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of the various layers, as well as exemplary materials, are described in more detail in U.S. Patent No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated by reference.

[0031] There are many more examples of each of these layers. For example, flexible and transparent substrate-anode combinations are disclosed in U.S. Patent No. 5,844,363, incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entirety, disclose examples of cathodes, including composite cathodes with a thin layer of a metal such as Mg:Ag overlying a transparent, conductive, sputter-deposited ITO layer. The principles and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0032] The layered structure described above is provided by way of non-limiting example. The function of an OLED can be achieved by combining various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of materials can be used to achieve the best performance. Any functional layer can include several sub-layers. For example, a light emitting layer can have two layers of different light emitting materials to achieve a desired light emission spectrum.

[0033] In one embodiment, an OLED can be described as having a "organic layer" disposed between a cathode and an anode. This organic layer can comprise one or more layers.

[0034] OLEDs also require an encapsulating layer, such as Figure 2 Illustrative, non-limiting, organic light emitting devices 200 are shown with Figure 1 Instead, an encapsulating layer 102 can also be included over the cathode 190 to protect against harmful materials from the environment, such as moisture and oxygen. Any material capable of providing an encapsulating function can be used as the encapsulating layer, such as glass or an organic-inorganic hybrid layer. The encapsulating layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, which is incorporated by reference in its entirety.

[0035] Devices made according to embodiments of the application can be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the devices. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays and tail lights.

[0036] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0037] As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. Where a first layer is described as "disposed on" a second layer, the first layer is disposed further from the substrate than the second layer. Unless specified that a first layer is "in contact with" a second layer, there can be other layers between the first and second layers. For example, a cathode can be described as "disposed on" an anode even though various organic layers are between the cathode and the anode.

[0038] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium, either in solution or suspension form.

[0039] A ligand can be referred to as "photosensitive" when it is believed to directly contribute to the photoactive properties of the emissive material. A ligand can be referred to as "auxiliary" when it is believed not to contribute to the photoactive properties of the emissive material, but an auxiliary ligand can alter the properties of a photosensitive ligand.

[0040] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistics limit by 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 produced by triplet-triplet annihilation (TTA).

[0041] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds that can produce E-type delayed fluorescence need to have a small singlet-triplet gap so that the conversion between states is possible. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize non-radiative decay from triplet, then the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin-statistical limit for electroluminescence.

[0042] E-type delayed fluorescence characteristics can be seen in exciplex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires that the light-emitting material have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal containing donor-acceptor light-emitting materials can be able to achieve this. The emission of these materials is often characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds often results in a small ΔE S-T . These states can include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (such as an amino or carbazole derivative) with an electron acceptor moiety (such as a N-containing six-membered aromatic ring).

[0043] Definitions of terms regarding substituents

[0044] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0045] Alkyl - As used herein, includes straight-chain and branched-chain alkyl groups. Alkyl groups can be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Of the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, alkyl groups can be optionally substituted.

[0046] Cycloalkyl - As used herein includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups can be optionally substituted.

[0047] Heteroalkyl - As used herein, heteroalkyl groups include alkyl chains in which one or more carbons is replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. Heteroalkyl groups can be heteroalkyl groups having 1 to 20 carbon atoms, preferably heteroalkyl groups having 1 to 10 carbon atoms, more preferably heteroalkyl groups having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxy methyl, ethoxymethoxy methyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl groups can be optionally substituted.

[0048] Alkenyl - As used herein, encompasses straight-chain, branched-chain, and cyclic alkenyl groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1,3-buten- dienyl, 1 -methyl-ethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1 -methyl- propenyl, 1,1 -dimethylpropenyl, 2-methylpropenyl, 1 -phenylpropenyl, 2-phenylpropenyl, 3- phenylpropenyl, 3,3-diphenylpropenyl, 1,2-dimethylpropenyl, 1 -phenyl- 1 -butenyl, 3-phenyl- 1 - butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group can be optionally substituted.

[0049] Alkynyl - As used herein, encompasses straight-chain alkynyl groups. Alkynyl groups can be alkynyl groups containing 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 - pentynyl, 2-pentynyl, 3,3-dimethyl- 1 -butynyl, 3-ethyl-3-methyl- 1 -pentynyl, 3,3-diisopropyl 1 - pentynyl, phenylethynyl, phenylpropynyl, and the like. Of the above, ethynyl, propynyl, propargyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -pentynyl, and phenylethynyl are preferred. Additionally, the alkynyl group can be optionally substituted.

[0050] Aryl or aromatic - As used herein, both non-fused and fused systems are contemplated. Aryl groups can be aryl groups having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthryl, azulenyl, phenanthryl, fluorenyl, pyrenyl, , perylenyl, and azulenyi, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenyl, and naphthyl. 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-terphenyl-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'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, and m-quaterphenyl. Additionally, the aryl group can be optionally substituted.

[0051] Heterocyclyl or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclyl groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Preferred non-aromatic heterocyclyl groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclyl groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepanyl, thiepanyl, azepanyl and tetrahydrothiopyranyl. Additionally, the heterocyclyl group can be optionally substituted.

[0052] Heteroaryl - as used herein, non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaromatic. Heteroaryl groups can be heteroaryl groups having 3 to 30 carbon atoms, preferably heteroaryl groups having 3 to 20 carbon atoms, more preferably heteroaryl groups having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, benzofuro[3,2-d]pyridine, furo[3,2-d]dipyridine, benzothieno[3,2-d]pyridine, thieno[3,2-d]dipyridine, benzoselenopheno[3,2-d]pyridine, selenopheno[3,2-d]dipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and nitrogen analogs thereof. Additionally, the heteroaryl group can be optionally substituted.

[0053] Alkoxy - as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as described above. The alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group can be optionally substituted.

[0054] Aryloxy - as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. In addition, the aryloxy group can be optionally substituted.

[0055] Aryloxy - as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. In addition, the aryloxy group can be optionally substituted.

[0056] Alkylsilyl groups - as used herein, encompass alkyl-substituted silyl groups. Alkylsilyl groups can be alkylsilyl groups having 3-20 carbon atoms, preferably alkylsilyl groups having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, methyldi-t-butylsilyl. Additionally, the alkylsilyl groups can be optionally substituted.

[0057] Arylsilyl groups - as used herein, encompass at least one aryl-substituted silyl group. Arylsilyl groups can be arylsilyl groups having 6-30 carbon atoms, preferably arylsilyl groups having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-t-butylsilyl. Additionally, the arylsilyl groups can be optionally substituted.

[0058] Alkylgermanyl groups - as used herein, encompass alkyl-substituted germanyl groups. Alkylgermanyl groups can be alkylgermanyl groups having 3-20 carbon atoms, preferably alkylgermanyl groups having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-t-butylgermanyl, triisobutylgermanyl, dimethyl-t-butylgermanyl, methyldi-t-butylgermanyl. Additionally, the alkylgermanyl groups can be optionally substituted.

[0059] Arylgermanyl groups - as used herein, encompass at least one aryl- or heteroaryl-substituted germanyl group. Arylgermanyl groups can be arylgermanyl groups having 6-30 carbon atoms, preferably arylgermanyl groups having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldiphenylgermanyl, diphenylphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyl-t-butylgermanyl. Additionally, the arylgermanyl groups can be optionally substituted.

[0060] The term "aza" in aza-dibenzofurans, aza-dibenzothiophenes, and the like, refers to the replacement of one or more C-H groups in the corresponding aromatic fragment with a nitrogen atom. For example, aza-triphenylenes include dibenzo[f,h]quinoxalines, dibenzo[f,h]quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the aza derivatives described above will occur to those of ordinary skill in the art and all such analogs are intended to be encompassed by the terms described herein.

[0061] In the present disclosure, when any one of the terms from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, and substituted phosphine is used, unless otherwise defined, it is intended to mean any one of the alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine groups can be substituted with one or more selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof.

[0062] It will be appreciated that when a molecular fragment is described as a substituent or otherwise attached to another moiety, it can be written by its name according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attached fragment are considered to be equivalent.

[0063] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by other stable isotopes thereof. The replacement of other stable isotopes in the compounds can be preferred due to its enhanced efficiency and stability of the device.

[0064] In the compounds mentioned in the present disclosure, poly-substitution refers to di-substitution and up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure is indicated as poly-substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent can exist at multiple available substitution positions on the structure to which it is connected, and the substituent that exists at multiple available substitution positions can be the same structure or different structures.

[0065] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a single ring or a multiple ring (including a spiro ring, a bridged ring, a fused ring, etc.), and an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a heteroaromatic ring. In this expression, 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 further away carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0066] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to the same carbon atom are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0067]

[0068] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0069]

[0070] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to further away carbon atoms are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] Further, the expression that adjacent substituents can optionally be joined to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thus forming a ring. This is exemplified by the following formula:

[0073]

[0074] According to one embodiment of the present application, a compound having the structure of Formula 1 is disclosed:

[0075]

[0076] wherein, ring A, ring C, ring D, ring E are each independently selected from an unsaturated carbocyclic ring having 5-30 carbon atoms or an unsaturated heterocyclic ring having 3-30 carbon atoms;

[0077] X1is selected from CR a R a , NR a , SiR a R a , O, S, Se, PR a or BR a ;

[0078] X2is selected from CR a , N, SiR a or B;

[0079] a, b, c, d are each independently selected from C, CR, N or NR;

[0080] a and b or c and d at least one group is connected by a single bond to form a ring; and, when a, b are connected by a single bond to form a ring, two R" are connected to form a ring; when c, d are connected by a single bond to form a ring, two R' are connected to form a ring;

[0081] R is the same or different at each occurrence represents mono-substituted, multi-substituted or non-substituted;

[0082] R, R aeach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having from 7-30 carbon atoms, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3-20 carbon atoms, substituted or unsubstituted arylsilyl having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0083] each occurrence is the same or different selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having from 7-30 carbon atoms, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3-20 carbon atoms, substituted or unsubstituted arylsilyl having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, hydroxyl, thiol, and combinations thereof;

[0084] adjacent substituents R, R', R", R a may optionally be linked to form a ring.

[0085] In this document, "at least one of a and b or c and d is connected with a single bond to form a ring" is intended to mean that at least one of a, b or c, d is selected from C and C, C and CR, C and N, CR and CR, CR and N, or N and N, and connected with a single bond to form a ring. For example, for compound BD1-3 of the present application: which is equivalent to c, d each being selected from C in Formula 1 and connected with a single bond to form a ring; for compound BD18-1 of the present application: which is equivalent to c, d each being selected from N and C in Formula 1 and connected with a single bond to form a ring.

[0086] In the present text, "adjacent substituents R, R', R", R a , is intended to mean that one or more of any of the following groups of substituents, e.g. between two substituents R, between two substituents R', between two substituents R", between substituents R and R', between substituents R and R", and between substituents R and R a , can be connected to form a ring. It is obvious that none of these adjacent substituents can also be connected to form a ring. a

[0087] According to one embodiment of the present application, wherein said ring A, ring C, ring D, ring E is each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms or a heteroaromatic ring having 3-30 carbon atoms.

[0088] According to one embodiment of the present application, wherein said ring A, ring C, ring D, ring E is each independently selected from an aromatic ring having 6-18 carbon atoms or a heteroaromatic ring having 3-18 carbon atoms.

[0089] According to one embodiment of the present application, wherein said ring A, ring C, ring D, ring E is each independently selected from a benzene ring or a six-membered heteroaromatic ring.

[0090] According to one embodiment of the present application, wherein said X1is selected from CR a R a , NR a , O, S or BR a .

[0091] According to one embodiment of the present application, wherein said X1is selected from CR a R a , O or NR a .

[0092] According to one embodiment of the present application, wherein said X1is selected from NR a .

[0093] According to one embodiment of the present application, wherein said X2is selected from N or B.

[0094] According to one embodiment of the present application, wherein said X2is selected from N.

[0095] According to one embodiment of the present application, wherein at least one hydrogen in said compound is replaced with deuterium.

[0096] According to one embodiment of the present application, wherein said two R' are connected to form a seven-membered ring, said seven-membered ring is a ring formed by two R' and c, d. ​

[0097] In the present text, "wherein the two R' are connected to form a seven-membered ring, the seven-membered ring is a ring formed by the two R' and c, d" is intended to mean, for example, for the compound of the present application BD1-3: wherein c, d are each C, and the two R' are carbazolyl and hydrogen, respectively, wherein the seven-membered ring refers to a new ring formed by the carbazolyl and hydrogen after c, d are connected to form a single bond.

[0098] According to one embodiment of the present application, wherein the two R" are connected to form a seven-membered ring, the seven-membered ring is a ring formed by the two R" and a, b.

[0099] In the present text, "wherein the two R" are connected to form a seven-membered ring, the seven-membered ring is a ring formed by the two R" and a, b" is intended to mean, for example, for the compound of the present application BD9-1: wherein a, b are each C, and the two R" are carbazolyl and hydrogen, respectively, wherein the seven-membered ring refers to a new ring formed by the carbazolyl and hydrogen after a, b are connected to form a single bond.

[0100] According to one embodiment of the present application, the compound has a structure represented by one of Formula 1-1 to Formula 1-16:

[0101]

[0102]

[0103] In Formula 1-1 to Formula 1-16, X3to X m are the same or different at each occurrence and are selected from N or CR, said X m correspond to said X3-X 23 The maximum number present in any one of Formula 1-1 to Formula 1-16;

[0104] R, R aeach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0105] adjacent substituents R, R a may optionally be linked to form a ring.

[0106] In this context, "in Formulae 1-1 to 1-16, X3to X m each occurrence is the same or different selected from N or CR, said X m corresponding to said X3-X 23 "the maximum number present in any one of Formulae 1-1 to 1-16", is intended to mean, for example, in Formula 1-1, X3to X 21 each occurrence is the same or different selected from N or CR; in Formula 1-3, X3to X 20 each occurrence is the same or different selected from N or CR; in Formula 1-5, X3to X 18 each occurrence is the same or different selected from N or CR; in Formula 1-7, X3to X 23 each occurrence is the same or different selected from N or CR; in Formula 1-9, X3to X 21 each occurrence is the same or different selected from N or CR; in Formula 1-11, X3to X 20 each occurrence is the same or different selected from N or CR; in Formula 1-13, X3to X 18 each occurrence is the same or different selected from N or CR; in Formula 1-16, X3to X 23 each occurrence is the same or different selected from N or CR.

[0107] In this context, "adjacent substituents R, R a"may optionally be linked to form a ring," is intended to mean that any one or more of the groups of substituents, e.g., between two substituents R, and between substituents R and R a It is readily apparent that none of these adjacent substituents can also be linked to form a ring.

[0108] According to one embodiment of the present application, wherein said R a each occurrence is the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having from 6 to 20 carbon atoms, substituted or unsubstituted amino having from 0 to 20 carbon atoms, hydroxy, mercapto, cyano, and combinations thereof.

[0109] According to one embodiment of the present application, wherein said R a each occurrence is the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, t-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthryl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothianyl, dibenzothianyl, benzothienyl, dibenzothienyl, dibenzoselenophenyl, phenylamino, diphenylamino, dibenzofuranyl phenylamino, hydroxy, mercapto, cyano, and combinations thereof.

[0110] According to one embodiment of the present application, wherein said R a having a structure represented by Formula 2:

[0111]

[0112] wherein * indicates the position where R a is attached;

[0113] X 24 to X 28 are each independently selected from N or CR x ;

[0114] R xeach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having from 7-30 carbon atoms, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3-20 carbon atoms, substituted or unsubstituted arylsilyl having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0115] adjacent substituents R x may optionally be linked to form a ring.

[0116] In this document, "adjacent substituents R x may optionally be linked to form a ring" is intended to mean that there can be a linkage between any adjacent substituents R x to form a ring. Obviously, there can also be no linkage between any adjacent substituents R x to form a ring.

[0117] According to one embodiment of the present application, wherein at least one of said X3to X 28 is N.

[0118] According to one embodiment of the present application, wherein said X3to X 23 are each occurrence the same or different selected from CR, said X 24 to X 28 are each occurrence the same or different selected from CR x ; R, R xeach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl of 1-20 carbon atoms, substituted or unsubstituted cycloalkyl of 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1-20 carbon atoms, substituted or unsubstituted heterocyclyl of 3-20 ring atoms, substituted or unsubstituted aralkyl of 7-30 carbon atoms, substituted or unsubstituted alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted alkenyl of 2-20 carbon atoms, substituted or unsubstituted aryl of 6-30 carbon atoms, substituted or unsubstituted heteroaryl of 3-30 carbon atoms, substituted or unsubstituted alkylsilicon of 3-20 carbon atoms, substituted or unsubstituted arylsilane of 6-20 carbon atoms, substituted or unsubstituted amino of 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0119] According to one embodiment of the present application, wherein the R, R x each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl of 1-6 carbon atoms, substituted or unsubstituted cycloalkyl of 3-6 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1-6 carbon atoms, substituted or unsubstituted aryl of 6-24 carbon atoms, substituted or unsubstituted heteroaryl of 3-12 carbon atoms, substituted or unsubstituted alkylsilicon of 3-6 carbon atoms, substituted or unsubstituted arylsilane of 6-12 carbon atoms, substituted or unsubstituted amino of 6-20 carbon atoms, hydroxyl, thiol, cyano, and combinations thereof;

[0120] According to one embodiment of the present application, wherein the R, R x each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, t-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthryl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothianyl, dibenzothianyl, benzothienyl, dibenzothienyl, dibenzoselenophenyl, phenylamino, diphenylamino, dibenzofuranyl phenylamino, hydroxyl, thiol, cyano, and combinations thereof.

[0121] According to one embodiment of the present application, wherein the R, R xAt least one of the following is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkoxysilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, substituted or unsubstituted amino, hydroxyl, mercapto, cyano groups having 6 to 20 carbon atoms, and combinations thereof.

[0122] In this document, "wherein R, R x "At least one of the following groups is selected" is intended to indicate that in equations 1-1 to 1-16, R a It has a structure represented by Equation 2: In all general formulas, when there are multiple R and / or multiple R's x At that time, multiple R and / or multiple R x At least one of them is selected from the group consisting of the following; for example, in Equation 1-1, R a It has a structure represented by Equation 2: That is, the compounds of the present invention have the following general formula: There are multiple R and / or multiple R's in this general formula. x At that time, multiple R and / or multiple R x At least one of the following groups shall be selected.

[0123] According to an embodiment of the present invention, wherein R, R x At least one of the following is selected from the group consisting of: deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthracene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, phenylamino, diphenylamino, dibenzofuranylphenylamino, hydroxyl, mercapto, cyano, and combinations thereof.

[0124] According to one embodiment of the present application, wherein the compound is selected from the group consisting of BD1-1 to BD1-87, BD2-1 to BD2-84, BD3-1 to BD3-84, BD4-1 to BD4-75, BD5-1 to BD5-19, BD6-1 to BD6-19, BD7-1 to BD7-19, BD8-1 to BD8-19, BD9-1 to BD9-19, BD10-1 to BD10-19, BD11-1 to BD11-19, BD12-1 to BD12-19, BD13-1 to BD13-19, BD14-1 to BD14-19, BD15-1 to BD15-19, BD16-1 to BD16-19, BD17-1 to BD17-9, and BD18-1 to BD18-8, the specific structures of BD1-1 to BD1-87, BD2-1 to BD2-84, BD3-1 to BD3-84, BD4-1 to BD4-75, BD5-1 to BD5-19, BD6-1 to BD6-19, BD7-1 to BD7-19, BD8-1 to BD8-19, BD9-1 to BD9-19, BD10-1 to BD10-19, BD11-1 to BD11-19, BD12-1 to BD12-19, BD13-1 to BD13-19, BD14-1 to BD14-19, BD15-1 to BD15-19, BD16-1 to BD16-19, BD17-1 to BD17-9, and BD18-1 to BD18-8 are shown in claim 13.

[0125] According to one embodiment of the present application, an electroluminescent device is also disclosed, comprising:

[0126] an anode,

[0127] a cathode,

[0128] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having structure of Formula 1, the compound having structure of Formula 1 being any of the above embodiments.

[0129] According to one embodiment of the present application, wherein the organic layer is an emissive layer, the compound is an emissive material.

[0130] According to one embodiment of the present application, wherein the emissive layer further comprises at least one host material; the host material has a structure represented by Formula 3:

[0131]

[0132] wherein,

[0133] R g1 to R g8each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilicon with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0134] R g9 and R g10 each occurrence is the same or different selected from substituted or unsubstituted aryl with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl with 3-30 carbon atoms.

[0135] According to one embodiment of the present application, wherein the host material is selected from the group consisting of BH1 to BH40, the specific structures of which are shown in claim 17.

[0136] According to another embodiment of the present application, a compound combination is also disclosed, comprising a compound represented by the structure of formula 1, the specific structure of which is shown in any of the aforementioned embodiments.

[0137] In combination with other materials

[0138] The materials described herein for specific layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. Combinations of materials are described in detail in U.S. Patent Application US2016 / 0359122A1 at paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or referenced in that paragraph are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of skill in the art can readily identify other materials that can be used in combination with the compounds disclosed herein.

[0139] The materials described herein as being useful for particular layers in organic light emitting devices can be used in combination with a variety of other materials present in the devices. For example, the light emitting dopants disclosed herein can be used in conjunction with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that can be present. Combinations of these materials are described in detail in US Patent Application US2015 / 0349273A1, paragraphs 0080-0101, which is incorporated by reference herein in its entirety. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that can be useful in combination.

[0140] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen atmosphere. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structure confirmation and property testing using one or more apparatuses conventional in the art, including but not limited to, nuclear magnetic resonance instrument of Bruker, liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer of Shanghai Linhong Technology, electrochemical work station of Wuhan Kessite, sublimation instrument of Anhui Beiyeke, etc. of Shimadzu, etc., in methods well known to those skilled in the art. In the examples of devices, the properties of the devices were also tested using apparatuses conventional in the art, including but not limited to, evaporation machine of Angstrom Engineering, optical test system, life test system of Suzhou Fushida, ellipsometer of Beijing Liangtuo, etc., in methods well known to those skilled in the art. Since those skilled in the art are all aware of the above-mentioned apparatuses, testing methods, etc. related content, the inherent data of the sample can be obtained certainly and unaffectedly, therefore the above-mentioned related content will not be expanded and described in this patent.

[0141] The disclosed compounds can be synthesized by the following routes:

[0142] Compound aa undergoes SN Ar reaction to obtain intermediate ac, then undergoes coupling reaction (e.g. Buchwald reaction, Ullmann reaction) with compound ad to obtain intermediate ae, followed by halogen-lithium exchange with X 112 in intermediate ae using organic lithium reagent, and finally under the action of base to obtain the target product.

[0143]

[0144] wherein, X 111 , X 112each independently selected from halogen, a, b each independently selected from C, CR, N or NR, two R' are linked to form a ring, X1, X2, ring A, ring C, ring D, ring E, R, R', R" are the same as defined in formula 1.

[0145] Material synthesis examples:

[0146] The preparation method of the compound of the present application is not limited, and the following compound is taken as an example, the synthesis route and preparation method thereof are as follows:

[0147] Synthesis example 1: synthesis of compounds BD1-3

[0148] Step 1: synthesis of intermediate 1

[0149]

[0150] Under the protection of nitrogen, cesium carbonate (9.9 g, 30.3 mmol), 1-bromo-2-chloro-3-fluorobenzene (3.2 g, 15.15 mmol), A-1 (5 g, 15.15 mmol) and DMAc (400 mL) were added to a three-necked flask, and the temperature was raised to 120°C until the reaction was complete. After cooling to room temperature, water was added, and the solid was precipitated and then filtered under suction to obtain yellow solid intermediate 1 (7.5 g, 14.45 mmol, 95%).

[0151] Step 2: synthesis of intermediate 2

[0152]

[0153] Under the protection of nitrogen, Pd2(dba)3 (360 mg, 0.39 mmol) and xylene (200 mL) were added to a three-necked flask, then Sphos (639 mg, 1.56 mmol) was added, stirred for 20 minutes, then diphenylamine (2.4 g, 14.45 mmol), intermediate 1 (7.5 g, 14.45 mmol), sodium tert-butoxide (2.8 g, 28.9 mmol) were added in turn, and the temperature was raised to 130°C until the reaction was complete. The reaction solution was filtered with diatomite, and the filtrate was concentrated with toluene, then filtered with a short column of silica gel, concentrated, and finally recrystallized with toluene twice to obtain yellow solid intermediate 2 (8 g, 13.15 mmol, 91%).

[0154] Step 3: synthesis of compounds BD1-3

[0155]

[0156] Under nitrogen protection, intermediate 2 (8 g, 13.2 mmol) and tert-butyl benzene (100 mL) were added into a three-neck flask, then tert-butyllithium (10 mL, 16 mmol) was added dropwise at -30 °C, after the addition was completed, the cold bath was removed, and after returning to room temperature, it was warmed to 60 °C for 1 h, then the reaction was cooled to -30 °C, and boron tribromide (1.5 mL, 16 mmol) was added dropwise, after stirring at room temperature for 30 min, it was cooled to 0 °C, and N,N-diisopropylethylamine (DIPEA, 4.4 mL, 26.3 mmol) was added dropwise, the ice bath was removed, and it was warmed to 120 °C overnight. The reaction was quenched by adding a potassium acetate solution under ice bath, and extracted with ethyl acetate, the organic phase was concentrated, then dissolved in toluene, filtered through magnesium sulfate and a short column of silica gel, the filtrate was concentrated, and recrystallized from toluene / n-heptane system to obtain yellow solid BD1-3 (0.8 g, 1.37 mmol, 10%). The molecular weight of the obtained compound was 581.2, which was confirmed as the target product.

[0157] Synthesis Example 2: Synthesis of compound BD3-3

[0158] Step 1: Synthesis of intermediate 3

[0159]

[0160] Under nitrogen protection, cesium carbonate (9.9 g, 30.3 mmol), 1-bromo-2-chloro-3-fluorobenzene (3.6 g, 17.2 mmol), A-2 (5 g, 17.2 mmol) and DMAc (50 mL) were added into a three-neck flask, and warmed to 130 °C until the reaction was complete. After cooling to room temperature, water was added, and the solid was filtered after precipitation to obtain yellow solid intermediate 3 (7.2 g, 15 mmol, 87%).

[0161] Step 2: Synthesis of intermediate 4

[0162]

[0163] Under nitrogen protection, Pd2(dba)3 (360 mg, 0.39 mmol) and xylene (200 mL) were added into a three-neck flask, then Sphos (2-biscyclohexylphosphino-2',6'-dimethoxybiphenyl, 639 mg, 1.56 mmol) was added, stirred for 20 min, then diphenylamine (2.4 g, 14.45 mmol), intermediate 3 (7 g, 14.58 mmol), sodium tert-butoxide (2.8 g, 28.9 mmol) were added in turn, and warmed to 130 °C until the reaction was complete. The reaction solution was filtered through diatomite, the filtrate was concentrated, then dissolved in toluene, filtered through a short column of silica gel, concentrated, and finally recrystallized from toluene twice to obtain yellow solid intermediate 4 (7.4 g, 13 mmol, 90%).

[0164] Step 3: Synthesis of compound BD3-3

[0165]

[0166] Under nitrogen protection, intermediate 4 (7 g, 12.3 mmol) and t-butylbenzene (100 mL) were added into a three-neck flask, then cooled to -30 °C and t-butyllithium (10 mL, 16 mmol) was added dropwise. After the addition was completed, the cold bath was removed and the temperature was raised to 60 °C for 1 h. Then the temperature was lowered to -30 °C and boron tribromide (1.5 mL, 16 mmol) was added dropwise. After stirring at room temperature for 30 min, the temperature was lowered to 0 °C and N,N-diisopropylethylamine (4.4 mL, 26.3 mmol) was added dropwise. The ice bath was removed and the temperature was raised to 120 °C for overnight. The reaction was quenched by adding potassium acetate solution under ice bath. Ethyl acetate was added to extract the product. The organic phase was concentrated and then dissolved in toluene. The solution was filtered through magnesium sulfate and silica gel short column. The filtrate was concentrated and recrystallized from toluene / n-heptane system to give yellow solid BD3-3 (1 g, 1.84 mmol, 14%). The molecular weight of the compound was 542.2, which was confirmed as the target product.

[0167] Those skilled in the art should know that the above preparation methods are only two exemplary examples, and those skilled in the art can obtain other compound structures of the present application by improving them.

[0168] Device Example 1

[0169] First, a glass substrate with an 80 nm thick indium tin oxide (ITO) anode was cleaned and treated with oxygen plasma and UV ozone. After the treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were sequentially evaporated on the ITO anode at a rate of 0.2-2 angstroms / second by thermal vacuum evaporation under a vacuum of about 10 -8 The compound HI was used as a hole injection layer (HIL). The compound HT was used as a hole transport layer (HTL). The compound EB was used as an electron blocking layer (EBL). The compound BD1-3 doped in the compound BH1 was co-evaporated as an emitting layer (EML). The compound HB was used as a hole blocking layer (HBL). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL). Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) was evaporated as an electron injection layer, and 120 nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0170] Device Example 2

[0171] The device embodiment 2 was prepared in the same manner as device embodiment 1 except that compound BD3-3 was used in place of compound BD1-3 in the light-emitting layer (EML).

[0172] Device comparative example 1

[0173] The device comparative example 1 was prepared in the same manner as device embodiment 1 except that compound BD1 was used in place of compound BD1-3 in the light-emitting layer (EML).

[0174] Device comparative example 2

[0175] The device comparative example 1 was prepared in the same manner as device embodiment 1 except that compound BD2 was used in place of compound BD1-3 in the light-emitting layer (EML).

[0176] The detailed device layer part structure and thickness are shown in Table 1. The layers in which more than one material is used are doped with the different compounds in the proportions by weight stated.

[0177] Table 1 Device structure of device embodiments and comparative examples

[0178]

[0179]

[0180] The structure of the materials used in the devices is shown below:

[0181]

[0182] The IVL of all the example and comparative example devices was measured at different current densities and voltages. The voltage (Voltage), external quantum efficiency (EQE) and device lifetime (LT95) were measured at constant current 1000 cd / m 2 The device data is shown in Table 2.

[0183] Table 2 Device data of device embodiments and comparative examples

[0184]

[0185]

[0186] Discussion:

[0187] From the data comparison of Example 1 and Comparative Examples 1, 2, it can be seen that when the carbazolene seven-membered nitrogen heterocycle is formed in Formula 1 of the application, the device performance of the example has a significant advantage over the comparative example. The voltage of Example 1 is reduced very obviously relative to Comparative Example 1 and Comparative Example 2, by 12.5% (4.20 vs. 4.80) and 6.8% (4.20 vs. 4.51), respectively; at the same time, the EQE of Example 1 is increased by 14.64% (6.50 vs. 5.67) and 18.61% (6.50 vs. 5.48) relative to Comparative Example 1 and Comparative Example 2, respectively, with a very large increase; more importantly, the device lifetime of Example 1 is increased by 7.27 times (1059 vs. 128) relative to Comparative Example 1 and 2.46 times (1059 vs. 306) relative to Comparative Example 2, achieving a very large increase. These results show that the compound of the application can greatly increase the fluorescent light emitting performance.

[0188] From the data comparison of Example 2 and Comparative Examples 1, 2, it can be seen that when the carbazolene seven-membered carbon ring is formed in Formula 1 of the application, the device performance of the example has a significant advantage over the comparative example. The voltage of Example 2 is reduced very obviously relative to Comparative Example 1 and Comparative Example 2, by 18.5% (3.91 vs. 4.80) and 13.3% (3.91 vs. 4.51), respectively; at the same time, the EQE of Example 1 is increased by 10.23% (6.25 vs. 5.67) and 14.05% (6.25 vs. 5.48) relative to Comparative Example 1 and Comparative Example 2, respectively, with a very large increase; more importantly, the device lifetime of Example 2 is increased by as high as 35 times (4619 vs. 128) relative to Comparative Example 1 and 14 times (4619 vs. 306) relative to Comparative Example 2, achieving a very large increase. These results again show that the compound of the application can greatly increase the fluorescent light emitting performance.

[0189] In summary, when the compound of the application, which is formed by introducing a substituent group into a boron-nitrogen heterocyclic skeleton to form a carbazolene macrocycle, is used as a fluorescent light emitting material in an organic electroluminescent device, the voltage can be effectively reduced, the EQE of the device can be greatly increased, and the device lifetime can be greatly increased, thereby improving the overall performance of the device.

[0190] It should be understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the application. Accordingly, the claimed application can include variations to the specific embodiments and preferred embodiments described herein, as will be apparent to those of skill in the art. Many of the materials and structures described herein are by way of example only and are not intended to limit the scope of the application. It should be understood that any theory described herein is not intended to limit the application.

Claims

1. A compound having a structure represented by Formula 1-1 or Formula 1-3: wherein In formula 1-1 or formula 1-3, X3to X m are the same or different at each occurrence and are selected from CR, said X m correspond to said X3-X 21 the maximum number present in formula 1-1 or formula 1-3; R is the same or different at each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms; R a independently at each occurrence, selected from the group consisting of: substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms; the substituted alkyl, substituted aryl, substituted heteroaryl means that any one of the alkyl, aryl and heteroaryl groups can be substituted with one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms.

2. The compound of claim 1, wherein R a is, at each occurrence, independently selected from: substituted or unsubstituted aryl having from 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 20 carbon atoms.

3. The compound of claim 1, wherein R a is, at each occurrence, independently selected from: substituted or unsubstituted aryl having 6-20 carbon atoms.

4. The compound of any one of claims 1-3, wherein at least one hydrogen in the compound is replaced with deuterium.

5. The compound of claim 1, wherein R a is, at each occurrence, independently selected from: substituted or unsubstituted aryl having from 6 to 12 carbon atoms.

6. The compound of claim 1, wherein the R a having a structure represented by Formula 2: wherein, * denotes R a Connected position; X 24 to X 28 are each independently selected from CR x ; R x at each occurrence, is the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms.

7. The compound as claimed in claim 6, wherein the X3to X 21 are the same or different at each occurrence and are selected from CR, 24 to X 28 are the same or different at each occurrence and are selected from CR x ; R, R x each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-12 carbon atoms.

8. The compound of claim 7, wherein the R, R x is, at each occurrence, selected from the group consisting of hydrogen, deuterium, fluorine.

9. The compound of claim 7, wherein the R, R x at least one of which is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl with 1-6 carbon atoms.

10. The compound of claim 7, wherein the R, R x at least one selected from the group consisting of deuterium, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, neopentyl.

11. The compound of claim 1, wherein the compound is selected from the group consisting of the following structures: wherein Optionally, the hydrogen in the above compounds can be partially or completely replaced with deuterium.

12. An electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and cathode, the organic layer comprising a compound of any one of claims 1-11.

13. The device of claim 12, wherein the organic layer is an emissive layer and the compound is an emissive material.

14. The device of claim 13, wherein the emissive layer further comprises at least one host material; the host material having a structure represented by Formula 3: wherein, R g1 to R g8 each occurrence is the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; R g9 and R g10 is, on each occurrence, 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.

15. The device of claim 14, wherein the host material is selected from the group consisting of the following structures: wherein, Optionally, the hydrogen in the above compounds can be partially or completely replaced with deuterium.

16. A compound combination comprising a compound of any one of claims 1-11.

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