Organic electroluminescent compound and use thereof

Abstract

The present invention provides an organic electroluminescent compound and a use thereof. The organic electroluminescent compound has a structure shown in a formula 1. The compound of the present invention can be used as a doping material in a light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer service life while having a lower driving voltage.

Description

An organic electroluminescent compound and its application

[0001] Cross-reference of related applications

[0002] This application claims priority to Chinese Patent Application No. 202410705317.9, filed on May 31, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This invention belongs to the field of organic electroluminescence technology, specifically relating to an organic electroluminescent compound and its application in organic electroluminescent devices. Background Technology

[0004] Organic electroluminescent displays are hailed as the "third display technology revolution" due to their numerous advantages, including self-illumination, wide viewing angle, high contrast, fast response, low power consumption, thinner and lighter design, and the ability to achieve flexible displays. They are widely used in mobile phones, televisions, computers, automotive displays, and other display and lighting applications.

[0005] With the development of organic electroluminescent materials, red and green light-emitting materials have largely met the needs of displays. However, blue light-emitting materials, due to their wide bandgap characteristics and difficulty in charge injection, lag behind red and green light in terms of efficiency and lifetime. Nevertheless, the performance of blue light emission, especially deep blue light, has a significant impact on improving display quality and reducing power consumption.

[0006] Commercially viable blue luminescent materials require high efficiency and long lifespan. Patent CN103222082A discloses an aromatic vinyl compound for use as a blue electroluminescent material; however, this compound has poor heat resistance and is prone to decomposition during sublimation. Similarly, patent CN1394195A discloses a series of anthracene derivatives that can be used as OLED blue light materials, but these anthracene derivatives have low efficiency and cannot meet the requirements of current displays in practical applications. Patent CN101018760A discloses a series of aromatic amine derivatives, but due to the imbalance between hole and electron transport properties, their lifespan is still not ideal. Therefore, the development of high-efficiency and long-lifespan blue luminescent materials is of great significance for promoting the development of organic electroluminescent display and lighting technologies.

[0007] Therefore, existing technologies still need to be improved and developed.

[0008] Summary of the Invention

[0009] In view of the above-mentioned defects and deficiencies in the prior art, the purpose of the present invention is to provide a suitable organic electroluminescent compound and its application.

[0010] In a first aspect, the present invention provides an organic electroluminescent compound having the structure shown in Formula 1:

[0011] In Equation 1, A1 to A 21 Each represents CR independently;

[0012] X may be the same or different, and each is independently selected from single bonds, O, S, Se, NR. N CR a R b R a C = CR b or SiR a R b ;

[0013] m and n are each independently selected from 0, 1 or 2, and one of m and n is 2, and m and n are not both 2 at the same time;

[0014] R, R N R a R b R N1 and R N2 The same or different, each independently selected from: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 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 alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted... The aryl group having 6-30 carbon atoms, the substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, the substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, the substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, the substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphinyl group, and combinations thereof having 0-20 carbon atoms; wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, aryl group having 6-20 carbon atoms, or heteroaryl group having 3-20 carbon atoms.

[0015] According to some embodiments of the compounds described in this invention, X may be the same or different, and each is independently selected from single bonds, O, S, and C. a R b or R a C = CRb .

[0016] According to some embodiments of the compound described in the present invention, R, R N1 and R N2 The following are selected independently, either identical or different: hydrogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted aroxy groups having 6-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-10 carbon atoms, substituted or unsubstituted alkynyl groups having 2-10 carbon atoms, and substituted or unsubstituted alkyne groups. The substituted aryl group having 6-20 carbon atoms, the substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, the substituted or unsubstituted alkylsilyl group having 3-10 carbon atoms, the substituted or unsubstituted arylsilyl group having 6-10 carbon atoms, the substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-10 carbon atoms; wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, aryl group having 6-20 carbon atoms, or heteroaryl group having 3-20 carbon atoms.

[0017] According to some embodiments of the compound described in the present invention, R, R in the compound N1 and R N2 The same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, aryl groups having 6-20 carbon atoms, or heteroaryl groups having 3-20 carbon atoms.

[0018] According to some embodiments of the compound described in the present invention, R, R in the compound N1 and R N2 Selected from the following structure:

[0019] According to some embodiments of the compounds of the present invention, the compounds have a structure shown in any one of Formulas 1-1 to 1-8:

[0020] In equations 1-1 to 1-8, X, A1 to A 21 R N1 and R N2 The definition is the same as in equation 1.

[0021] In some embodiments of the compounds according to the present invention, X is selected from O and S.

[0022] According to some embodiments of the compound of the present invention, the compound has a structure shown in any one of Formula 1-1 to Formula 1-2:

[0023] In Equations 1-1 to 1-2, A1 to A 21 Each independently represents CR and N;

[0024] R, R N1 and R N2 The following are selected independently, either identical or different: hydrogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted aroxy groups having 6-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-10 carbon atoms, substituted or unsubstituted alkynyl groups having 2-10 carbon atoms, and substituted or unsubstituted alkyne groups. The substituted aryl group having 6-20 carbon atoms, the substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, the substituted or unsubstituted alkylsilyl group having 3-10 carbon atoms, the substituted or unsubstituted arylsilyl group having 6-10 carbon atoms, the substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-10 carbon atoms; wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, aryl group having 6-20 carbon atoms, or heteroaryl group having 3-20 carbon atoms.

[0025] According to some embodiments of the compounds described in this invention, A1 to A 10 Each independently represents CR, A 11 To A 21 Each of them independently represents N.

[0026] According to some embodiments of the compounds of the present invention, the compounds have a structure shown in any one of Formulas 1-5 to 1-6:

[0027] In Equations 1-5 to 1-6, A1 to A 21 Each represents CR independently;

[0028] R, R N1 and R N2 The same or different, each independently selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, aryl groups having 6-20 carbon atoms, or heteroaryl groups having 3-20 carbon atoms.

[0029] According to some embodiments of the compounds described in this invention, the compounds are selected from the structures indicated by numbers C1 to C156:

[0030] A second aspect of the present invention provides the use of the compound described in the first aspect of the present invention in the preparation of organic electroluminescent devices.

[0031] According to some embodiments of the application described in this invention, the compound is used as a blue light doping material in the light-emitting layer of an organic electroluminescent device.

[0032] According to some embodiments of the application described in this invention, the doping amount of the compound is equivalent to 1wt%-20wt% of the host material in the luminescent layer.

[0033] According to some embodiments of the application described in this invention, the doping amount of the compound is equivalent to 1 wt%-10 wt% of the host material in the light-emitting layer.

[0034] According to some embodiments of the application described in this invention, the doping amount of the compound is equivalent to 2wt%-8wt% of the host material in the light-emitting layer.

[0035] A third aspect of the present invention provides an organic electroluminescent device, comprising a light-emitting layer, wherein the doping material of the light-emitting layer comprises the compound described in the first aspect of the present invention.

[0036] According to some embodiments of the light-emitting device of the present invention, it further includes: an anode and a cathode, wherein the light-emitting layer is disposed between the anode and the cathode.

[0037] According to some embodiments of the light-emitting device of the present invention, the organic electroluminescent device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0038] A fourth aspect of the present invention provides a display component comprising the compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention.

[0039] A fifth aspect of the present invention provides a display device comprising the compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention.

[0040] The beneficial effects of the present invention include: the compound described in the present invention can be used as a doping material in the light-emitting layer of organic electroluminescent devices, so that the organic electroluminescent devices have lower driving voltage while having higher current efficiency and lifetime. Attached Figure Description

[0041] Figure 1 is a schematic diagram of an organic light-emitting device according to a specific embodiment of the present invention.

[0042] Figure 2 is a schematic diagram of an organic light-emitting device in another specific embodiment of the present invention.

[0043] The attached figures are labeled as follows:

[0044] 100, First organic light-emitting device; 101, Substrate; 110, Anode; 120, Hole injection layer; 130, Hole transport layer; 140, Electron blocking layer; 150, Light-emitting layer; 160, Hole blocking layer; 170, Electron transport layer; 180, Electron injection layer; 190, Cathode; 102, Encapsulation layer; 200, Second organic light-emitting device. Detailed Implementation

[0045] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments and accompanying drawings. The specific embodiments described herein are for illustrative purposes only and are not intended to limit the invention in any way. Furthermore, descriptions of well-known structures and techniques are omitted in the following description to avoid unnecessarily obscuring the concepts of this disclosure. Such structures and techniques have also been described in many publications.

[0046] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 schematically and non-limitingly illustrates a first organic light-emitting device 100. The figure is not necessarily drawn to scale, and some layer structures may be omitted as needed. The first organic light-emitting 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. The first organic light-emitting 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 US7279704B2, the entire contents of which are incorporated herein by reference.

[0047] There are further examples of each of the above layers. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent 5,844,363A, 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 20030230980A1, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent 6,3032387P0 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 20030230980A1, which is incorporated herein by reference in its entirety. U.S. Patents US5,703,436A and US5,707,745A, incorporated herein by reference in their entirety, disclose examples of cathodes comprising 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. Patents US6,097,147A and US20,030,230,980A1, also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174H6, also incorporated herein by reference in its entirety.

[0048] 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.

[0049] 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.

[0050] OLEDs also require an encapsulation layer. Figure 2 schematically and non-limitingly illustrates a second organic light-emitting device 200, which, unlike Figure 1, may include an encapsulation layer 102 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 US7,968,146B2, the entire contents of which are incorporated herein by reference.

[0051] 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.

[0052] The materials and structures described in this invention can also be used in other organic electronic devices listed above.

[0053] Definition of the term "substituent group"

[0054] The term "halogen or halide" as used in this invention includes fluorine, chlorine, bromine, and iodine.

[0055] As used in this invention, the term "alkyl" includes both straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isolaryl, 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. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred.

[0056] As used in this invention, the term "alkenyl" comprises a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with one or more carbon-carbon double bonds. An alkenyl group can be a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with 2-20 carbon atoms and having one or more carbon-carbon double bonds, preferably an alkenyl group with 2-12 carbon atoms, including but not limited to vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, isobutenyl, butadienyl, 1-pentenyl, 2-pentenyl, isopentenyl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl, or 1,3,5-hextrienyl, etc. Furthermore, the alkenyl group may optionally be substituted.

[0057] As used in this invention, the term "cycloalkyl" includes cyclic alkyl groups. A cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group 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, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0058] As used in this invention, the term "heteroalkyl" refers to an alkyl chain in which one or more carbon atoms are substituted with heteroatoms 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, and more preferably heteroalkyl groups having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminolactone, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisolactone, tert-butyldimethylsilyl, triethylsilyl, triisolactone, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisolactone. In addition, heteroalkyl groups may be optionally substituted.

[0059] The terms "carbocyclic group" and "carbocyclic" used in this invention are used interchangeably to refer to non-aromatic saturated or partially unsaturated monocyclic or polycyclic systems composed of carbon atoms as ring atoms, including aromatic rings composed of carbon atoms as ring atoms. Furthermore, the carbocyclic group may optionally be substituted.

[0060] The term "heterocyclic group" as used in this invention is interchangeable with "heterocycle," "carbon heterocycle," and "carbon heterocyclic group," and includes aromatic cyclic groups and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-30 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-30 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic 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 heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacycloyl, dioxohexyl, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanyl-heptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiopyrroleyl. Furthermore, the heterocyclic group may optionally be substituted.

[0061] The term "aryl or aromatic group" as used in this invention includes both non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene, and naphthalene. Additionally, 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-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'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0062] As used in this invention, the term "heteroaryl" includes non-fused and fused heteroaryl groups with 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, iso Quinoline, cyclophosphine, quinazolin, quinoxaline, naphthidine, phthalazine, pteridine, guarbenzine, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, 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.

[0063] As used in this invention, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An 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, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group may optionally be substituted.

[0064] The term "aryloxy group" as used in this invention is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups 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 groups. Additionally, the aryloxy group may optionally be substituted.

[0065] As used in this invention, the term "aralkyl" encompasses aryl-substituted alkyl groups. Aralkyl groups can be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 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 The compounds include alkyl groups, such as 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-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. Additionally, the alkyl group may optionally be substituted.

[0066] As used herein, the term "alkylsilyl or silyl" encompasses silyl groups substituted with groups listed in the above alkyl groups, such as methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, etc.

[0067] As used in this invention, the term "arylsilyl" refers to a group consisting of any of the aforementioned aryl and silyl groups.

[0068] As used in this invention, the term "aza" in terms such as "azadibenzofuran" and "azadibenzothiophene" refers to the substitution of one or more CH groups in the corresponding aromatic fragment with nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoline, 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.

[0069] In this invention, unless otherwise defined, when any term from the group consisting of, for example, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, 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, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alksilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl, which may be one or more alkyl groups selected from deuterium, halogen, and unsubstituted alkane having 1-20 carbon atoms. The group includes unsubstituted cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, unsubstituted arylyl groups having 6-30 carbon atoms, unsubstituted heteroaryl groups having 3-30 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.

[0070] 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.

[0071] In the compounds mentioned in this invention, 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.

[0072] In the compounds mentioned in this invention, 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 of the same structure or different structures.

[0073] In the compounds mentioned in this invention, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compound cannot connect to form a ring. In the compounds mentioned in this invention, 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 formed 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.

[0074] 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. Such combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent US20160359122A1, 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.

[0075] The present invention describes materials that can be used in specific layers in organic light-emitting devices and can be used in combination with a variety of other materials present in said device. For example,

[0076] The compounds disclosed in this invention can be used in combination with various substrates, delivery 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 US20150349273A1, 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.

[0077] 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 Agilent liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimation apparatuses, 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 conventional instruments in the art (including but not limited to vapor deposition machines manufactured by Nanjing Institute of Microelectronics, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Wuhan Yiguang Technology, 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.

[0078] 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:

[0079] Synthesis Example 1: Synthesis of Compound C1

[0080] The synthesis route is as follows:

[0081] Specific synthesis steps:

[0082] (1) Under nitrogen protection, 200 mL of toluene, 14.9 g (0.1 mol) of p-tert-butylaniline, 26.9 g (0.1 mol) of 3-bromo-5-tert-butylbenzothiophene, 14.4 g (0.15 mol) of sodium tert-butoxide, 0.3 g of tris(dibenzylacetone)dipalladium, and 0.3 g of 2-dicyclohexylphospho-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask. The mixture was stirred and slowly heated to 95-100 °C and reacted for 2 hours. After cooling, 8 mL of hydrochloric acid and 100 mL of water were added to adjust the pH to acidic, and the mixture was separated. The organic phase was washed with water until neutral, subjected to column chromatography, recrystallized, and dried to obtain 27.6 g of product C1-1, with a yield of 82%.

[0083] (2) Under nitrogen protection, 200 mL of xylene was added to a 500 mL three-necked flask, and 12.2 g (0.127 mol) of sodium tert-butoxide was added with stirring. Then, 28.7 g (0.085 mol) of intermediate C1-1, 31.9 g (0.085 mol) of 3,4-dibromo-5-iodotoluene, 0.12 g of tris(dibenzylacetone)dipalladium, and 0.15 g of tri-tert-butylphosphine were added. The temperature was slowly raised to 110 °C, and after stabilization, it was raised to 130 °C and reacted for 2 hours. The reaction solution was cooled to 50 °C, 40 mL of water was added, the mixture was washed with water, subjected to column chromatography, recrystallized, and dried to obtain 49.7 g of C1-2 product, with a yield of 85%.

[0084] (3) Under nitrogen protection, 250 mL of tetrahydrofuran and 26.7 g (0.1 mol) of 2'-bromo-4-chlorobiphenyl were added sequentially to a 500 mL three-necked flask. Under nitrogen protection, the temperature was lowered to -80 °C. 60 mL of 2 mol / L n-butyllithium was added dropwise from -80 to -70 °C. The addition was completed in about 30 minutes. The reaction was maintained at -80 to -70 °C for 1.5 hours. 20.8 g (0.1 mol) of 10,11-dihydrodibenzo[a,b]cyclohepten-5-one was added in batches at -70 to -60 °C. After the addition was completed, the reaction was maintained at -70 to -60 °C for 1.5 hours. Add 40 ml of concentrated hydrochloric acid and 80 ml of water to the reaction solution until the pH is acidic. Allow the solution to stand and separate the phases. Extract with ethyl acetate, combine the organic phases, wash with water until neutral, and desolvate under negative pressure to obtain 45 g of yellow viscous liquid of C1-3 with a purity of 85%. Proceed directly to the next step.

[0085] (4) Under nitrogen protection, 45g of intermediate C1-3 yellow viscous liquid, 160ml of glacial acetic acid, and 12ml of concentrated hydrochloric acid were added sequentially to a 500mL three-necked flask. Stirring was started, and the mixture was heated to 105-110℃ and refluxed for 4 hours. 200mL of toluene was added to the reaction solution, and the mixture was separated, washed with water until neutral, dissolved, subjected to column chromatography, recrystallized and dried to obtain 30.2g of C1-4 pale yellow solid.

[0086] (5) Under nitrogen protection, 200 mL of xylene, 11.9 g (0.08 mol) of p-tert-butylaniline, 30.2 g (0.08 mol) of intermediate C1-4, 13.4 g (0.12 mol) of potassium tert-butoxide, 0.36 g of tris(dibenzylacetone)dipalladium, and 0.36 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a 500 mL three-necked flask. The mixture was stirred and slowly heated to 105-110 °C and reacted for 2 hours. After cooling the reaction solution, 8 mL of hydrochloric acid and 100 mL of water were added to adjust the pH to acidic, and the mixture was separated. The organic phase was washed with water until neutral, subjected to column chromatography, recrystallized, and dried to obtain 40.8 g of C1-5 product, with a yield of 83%.

[0087] (6) Under nitrogen protection, 200 mL of xylene was added to a 500 mL three-necked flask, and 7.2 g (0.75 mol) of sodium tert-butoxide was added with stirring. Then, 29.3 g (0.05 mol) of intermediate C1-2, 24.6 g (0.05 mol) of intermediate C1-5, 0.09 g of tris(dibenzylacetone)dipalladium, and 0.11 g of tri-tert-butylphosphine were added. The temperature was slowly raised to 110 °C, and after stabilization, it was raised to 130 °C and reacted for 4 hours. The reaction solution was cooled to 50 °C, 40 mL of water was added, the mixture was washed with water, subjected to column chromatography, recrystallized, and dried to obtain 40.3 g of C1-6 product, with a yield of 81%.

[0088] (7) Under nitrogen protection, 160 ml of analytical grade xylene was added to a 250 ml reaction flask, and 10 g (0.01 mol) of intermediate C1-6 was added with stirring. The mixture was heated to approximately 55 °C to dissolve, then cooled to -30 °C. Nitrogen was purged three times, and 6 mL of 2 mol / L n-butyllithium was added dropwise. The temperature was slowly increased to 75 °C, and the reaction was allowed to proceed for 2 hours. The temperature was then lowered to -25 °C, and 3.0 g (0.012 mol) of boron tribromide was added. The temperature was then slowly increased to 60 °C and held for 3 hours. The temperature was then lowered to -20 °C, and 2.3 g of N,N-diisopropylethylamine was added dropwise. The temperature was then slowly increased to 80 °C and held for 1 hour, then increased to 130 °C and the reaction was allowed to proceed for 12 hours. The reaction mixture was cooled to 50 °C, subjected to column chromatography, recrystallized, and dried to obtain 2.8 g of the product, with a yield of 30%.

[0089] Product MS (m / e): 924; 1 H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.60-7.54(m,2H),7.41-7.25(m,9H),7.21-7.16(m,4H),7. 07-7.01(m,6H),6.98(s,1H),6.88-6.85(dd,1H),6.73-6.68(m,2H),2.98-2.92(m,4H),2.29(s,3H),1.35-1.33(d,27H).

[0090] Synthesis Example 2: Synthesis of Compound C14

[0091] Specific synthesis steps:

[0092] Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C14 was obtained.

[0093] Product MS (m / e): 11541 H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.60-7.55(m,2H),7.50-7.47(t,1H),7.40-7. 25(m,11H),7.22-7.16(m,5H),7.07-6.99(m,5H),6.91-6.85(m,3H),2.97-2.93(m,4H),1.36-1.33(m,54H).

[0094] Synthesis Example 3: Synthesis of Compound C61

[0095] Specific synthesis steps:

[0096] Using compounds replace Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 1, compound C61 was obtained.

[0097] Product MS (m / e): 1088 1 H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.61-7.54(m,2H),7.41-7.24(m,9 H),7.16-6.85(m,11H),6.73-6.68(dd,2H),2.29(s,3H),1.84-1.57(m,4H),1.35-1.28(m,48H).

[0098] Synthesis Example 4: Synthesis of Compound C73

[0099] Specific synthesis steps:

[0100] Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 1, compound C73 was obtained.

[0101] Product MS (m / e): 1220, 1H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.75-7.66(m,3H),7.51-7.24(m,15H),7.21-7.12(m, 3H),7.08-6.92(m,5H),6.73-6.68(dd,2H),2.29(s,3H),1.82-1.58(m,4H),1.39-1.25(m,57H).

[0102] Synthesis Example 5: Synthesis of Compound C93

[0103] Specific synthesis steps:

[0104] Using compounds replace Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 1, compound C93 was obtained.

[0105] Product MS (m / e): 1222 1 H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.61-7.54(m,2H),7.50-7.47(m,3H),7.39-7 .18(m,14H),7.08-6.99(m,5H),6.88-6.85(dd,1H),6.73-6.68(dd,2H),2.29(s,3H),1.35-1.31(m,63H).

[0106] Synthesis Example 6: Synthesis of Compound C102

[0107] Specific synthesis steps:

[0108] Using compounds replace Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 1, compound C102 was obtained.

[0109] Product MS (m / e): 982, 1H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.39-7.25(m,8H),7.21- 6.98(m,13H),6.98(s,1H),6.89-6.84(m,3H),2.98-2.89(m,4H),1.36-1.33(t,36H).

[0110] Synthesis Example 7: Synthesis of Compound C107

[0111] Specific synthesis steps:

[0112] Using compounds replace Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 1, compound C107 was obtained.

[0113] Product MS (m / e): 1092, 1 H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.62-7.57(m,2H),7.47-7.23( m,25H),7.15-7.12(m,2H),7.06-7.01(m,4H),6.91(s,2H),6.86(s,1H),1.35-1.33(m,27H).

[0114] Synthesis Example 8: Synthesis of Compound C121

[0115] Specific synthesis steps:

[0116] Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C121 was obtained.

[0117] Product MS (m / e): 978, 1H NMR (400MHz, CDCl3): δ7.85-7.80(m,3H),7.74-7.71(d,1H),7.39-7.25(m,8H),7.21-7.13(m,3H),7.10-6.92(m,7H) ),6.84-6.81(dd,2H),6.73-6.68(dd,2H),3.02-2.82(m,4H),2.28(s,3H),1.84-1.57(m,4H),1.36-1.29(dd,30H).

[0118] Synthesis Example 9: Synthesis of Compound C126

[0119] Specific synthesis steps:

[0120] Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C126 was obtained.

[0121] Product MS (m / e): 1094 1 H NMR (400MHz, CDCl3): δ7.86-7.80(m,3H),7.74-7.71(d,1H),7.47-7.21(m,18H),7.17-7.09( m,2H),7.04-7.01(dd,1H),6.97-6.92(m,3H),6.89-6.85(dd,2H),6.84-6.81(dd,2H),1.82- 1.57(m,4H),1.37-1.29(m,39H).

[0122] Synthesis Example 10: Synthesis of Compound C134

[0123] Specific synthesis steps:

[0124] Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C134 was obtained.

[0125] Product MS (m / e): 1224 1H NMR (400MHz, CDCl3): δ7.82-7.80(d,1H),7.74-7.71(d,1H),7.49(t,1H),7.39-7.25(m,8H),7.21-7.05(m,10H),7 .04-6.98(m,3H),6.95-6.92(m,2H),6.90-6.85(m,2H),2.96-2.83(m,4H),1.83-1.57(m,4H),1.37-1.29(m,57H).

[0126] Synthesis Example 11: Synthesis of Compound C141

[0127] Specific synthesis steps:

[0128] Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C141 was obtained.

[0129] Product MS (m / e): 1104 1 H NMR (400MHz, CDCl3): δ7.82-7.80(dd,1H),7.74-7.71(dd,1H),7.39-7.25(m,8H),7.18-6.92( m,13H),6.85(s,1H),6.73-6.68(dd,2H),2.29(s,3H),1.82-1.58(m,4H),1.40-1.25(m,48H).

[0130] Synthesis Example 12: Synthesis of Compound C153

[0131] Specific synthesis steps:

[0132] Using compounds replace Using compounds replace Using compounds replace Using compounds replace Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, compound C153 was obtained.

[0133] Product MS (m / e): 1224 1 H NMR (400MHz, CDCl3): δ7.82-7.80(dd,1H),7.74-7.66(m,3H),7.50-7.20(m,16H),7.17-7.13(m ,2H),7.07-7.01(m,3H),6.96-6.93(m,2H),6.75(s,2H),1.82-1.58(m,4H),1.40-1.24(m,57H).

[0134] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0135] Device Example 1

[0136] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and 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 10⁻⁸ Torr. The deposition rate was achieved sequentially on the ITO anode via thermal vacuum. Simultaneously, the deposition compounds HT and NDP-9 (weight ratio 97:3) were used as a hole injection layer (HIL) with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, BH, which serves as the blue light source, and C1, the compound of the present invention, which serves as a dopant (weight ratio 98:2), are co-deposited as an emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited (weight ratio 50:50) as an electron transport layer (ETL), with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0137] Device Examples 2 to 12

[0138] The method is the same as in Device Example 1, except that in the light-emitting layer (EML), the compounds C1 of the present invention listed in Table 1, namely C14, C61, C73, C93, C102, C107, C121, C126, C134, C141 and C153, are used instead of compound C1 as doping material.

[0139] Device Comparison Example 1

[0140] The method is the same as in Device Example 1, except that compound A is used instead of compound C1 of the present invention as the dopant material in the light-emitting layer (EML).

[0141] The material structure used in the device is shown below:

[0142] Table 1 lists the values ​​at 10 mA / cm 2 Under the given conditions, the voltage (V), external quantum efficiency (EQE), and lifetime (T) were measured. To better illustrate the data comparison, the voltage, efficiency, and lifetime of Comparative Example 1 were set to 100%. The voltage, efficiency, and lifetime data of Device Examples 1 to 12 were all converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0143] Table 1

[0144] Discussion: As shown in Table 1, at 10 mA / cm 2 At the specified current density, compared to Comparative Example 1, Device Examples 1 to 12 exhibit a 2-18% reduction in voltage, a 3%-32% increase in external quantum efficiency, and a 2%-23% extension in device lifetime. These data demonstrate that the compounds of this invention, which are formed by a specific structural connection of a spirocyclic structure and a boron-containing heterocyclic structure, exhibit higher current efficiency and lifetime than Comparative Example Compound A due to the introduction of a spirocyclic structure. This structural change unexpectedly leads to superior device performance, proving the unique advantages of the compounds of this invention.

[0145] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

An organic electroluminescence compound having a structure represented by the following formula 1: In Formula 1, A1to A 21 each independently represents CR; X is the same or different, each independently selected from the group consisting of a single bond, O, S, Se, NR N , CR a R b , R a C=CR b or SiR a R b ; m and n are each independently selected from 0, 1 or 2, and one of m and n is 2, and m and n are not both 2 at the same time; R, R N R, R a R, R b R, R N1 R, R N2 are the same or different, each independently 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 carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3-20 carbon 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 alkynyl 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 amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; the substituents employed in said substitutions are selected from the group consisting of deuterium, halogen, alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms, or heteroaryl with 3-20 carbon atoms. The compound according to claim 1, characterized in that, X is the same or different, each independently selected from the group consisting of a single bond, O, S, CR a R b or R a C=CR b ; and / or, in the compound, R, R N1 and R N2 each independently is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 10 carbon atoms, substituted or unsubstituted heterocycloalkyl having from 3 to 10 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 20 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 10 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 20 carbon atoms, The substituted or unsubstituted alkenyl group having 2-10 carbon atoms, the substituted or unsubstituted alkynyl group having 2-10 carbon atoms, the substituted or unsubstituted aryl group having 6-20 carbon atoms, the substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, the substituted or unsubstituted alkylsilyl group having 3-10 carbon atoms, the substituted or unsubstituted arylsilyl group having 6-10 carbon atoms, the substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-10 carbon atoms; wherein the substituent used for the substitution is selected from deuterium, halogen, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, aryl group having 6-20 carbon atoms, or heteroaryl group having 3-20 carbon atoms; R, R and R are the same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3-10 carbon atoms, the substitution employing as a substituent a group selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, or heteroaryl having 3-20 carbon atoms; N1 R, R and R are the same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3-10 carbon atoms, the substitution employing as a substituent a group selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, or heteroaryl having 3-20 carbon atoms; N2 R, R and R are the same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3-10 carbon atoms, the Preferably, R, R in the compound N1 and R N2 Selected from the following structure: The compound according to claim 1 or 2, characterized in that, The compound has a structure shown in any one of Formulas 1-1 to 1-8: In formulae 1-1 to 1-8, X, A1to A 21 , R N1 and R N2 are defined as in formula 1; Preferably, X is selected from O and S. The compound according to any one of claims 1-3 is characterized in that, The compound has a structure shown in any one of Formula 1-1 to Formula 1-2: In formulae 1-1 to 1-2, A1to A 21 each independently represents CR, N; preferably, A1to A 10 each independently represents CR, A 11 to A 21 each independently represents N; R, R N1 and R N2 are the same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl of 1-10 carbon atoms, substituted or unsubstituted cycloalkyl of 3-10 carbon atoms, substituted or unsubstituted heteroalkyl of 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl of 3-10 carbon atoms, substituted or unsubstituted aralkyl of 7-20 carbon atoms, substituted or unsubstituted alkoxy of 1-10 carbon atoms, substituted or unsubstituted aryloxy of 6-20 carbon atoms, substituted or unsubstituted alkenyl of 2-10 carbon atoms, substituted or unsubstituted alkynyl of 2-10 carbon atoms, substituted or unsubstituted aryl of 6-20 carbon atoms, substituted or unsubstituted heteroaryl of 3-20 carbon atoms, substituted or unsubstituted alkylsilyl of 3-10 carbon atoms, substituted or unsubstituted arylsilyl of 6-10 carbon atoms, substituted or unsubstituted amino of 0-10 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; the substituents employed in said substitution being selected from deuterium, halogen, alkyl of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl of 6-20 carbon atoms, or heteroaryl of 3-20 carbon atoms. The compound according to any one of claims 1-4 is characterized in that, The compound has a structure shown in any one of Formulas 1-5 to 1-6: In Formulas 1-5 to 1-6, A1to A 21 each independently represents CR; R, R N1 and R N2 are the same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl of 1-10 carbon atoms, substituted or unsubstituted cycloalkyl of 3-10 carbon atoms, substituted or unsubstituted heteroalkyl of 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl of 3-10 carbon atoms, the substitutions taken with substituents selected from deuterium, halogen, alkyl of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl of 6-20 carbon atoms, or heteroaryl of 3-20 carbon atoms. The compound according to any one of claims 1-5 is characterized in that, The compound is selected from the structures shown in C1 to C156: The use of the compound according to any one of claims 1-6 in the preparation of organic electroluminescent devices, preferably, The compound is used as a blue light dopant material in the light-emitting layer of organic electroluminescent devices; More preferably, the doping amount of the compound is equivalent to 1 wt%-20 wt% of the host material in the light-emitting layer, preferably 1 wt%-10 wt%, more preferably 2 wt%-8 wt%. An organic electroluminescent device includes a light-emitting layer, wherein the doping material of the light-emitting layer comprises a compound according to any one of claims 1-6. The light-emitting device according to claim 8 is characterized in that, Also includes: Anode and cathode, wherein the light-emitting layer is disposed between the anode and cathode; Preferably, the organic electroluminescent device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. A display component or device comprising the compound of any one of claims 1-6 or the organic electroluminescent device of any one of claims 8-9.

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