Boron-nitrogen compound and application thereof

Abstract

The invention provides a boron-nitrogen compound and application thereof, the boron-nitrogen compound has a structure as shown in a formula I or a formula II, and the boron-nitrogen compound not only realizes fine adjustment of a spectrum but also further improves luminous efficiency through extension conjugation and introduction of nitrogen atoms. The boron-nitrogen compound has a narrow spectrum and is used as a narrow-spectrum luminescent material for preparing a luminescent layer of an organic electroluminescent device, the prepared organic electroluminescent device realizes narrow-spectrum TADF emission, the electroluminescent spectrum is in a green light-yellow light area, the half-peak width is less than 45nm, and the boron-nitrogen compound has a wide application prospect. And moreover, the highest external quantum efficiency of electroluminescence of the device is up to 30% or above, and the device has a relatively long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence and relates to a boron nitrogen compound and application thereof. Background Art

[0002] Organic optoelectronic materials are a class of organic materials with properties such as the generation, conversion, and transmission of photons and electrons. Currently, the controllable optoelectronic properties of organic optoelectronic materials have been applied to organic light-emitting diodes (OLEDs), organic photovoltage (OPVs), organic field effect transistors (OFETs), and even organic lasers. In recent years, OLEDs have become a very popular new type of flat-panel display product both domestically and internationally. OLED displays feature self-luminescence, wide viewing angles, short response times, high luminous efficiency, a wide color gamut, low operating voltage, thin panels, the ability to produce large, flexible panels, and low cost, earning them the reputation of being the star flat-panel display product of the 21st century.

[0003] The history of organic electroluminescence can be traced back to the report by Bernanose et al. in 1953 (Holst GA, Kster T, Voges E, et al. FLOX—an oxygen-flux-measuring system using a phase-modulation method to evaluate the oxygen-dependent fluorescence lifetime, Science Direct. Sensors and Actuators B: Chemical, 1995, 29, 213.). About 10 years later, in 1963, Pope et al. from New York University applied voltage to anthracene crystals and observed the fluorescence emission of anthracene (M. Pope, H. Kallmann and P. Magnante, Electroluminescence in Organic Crystals, J. Chem. Phys., 1963, 38, 2042). In 1987, CW Tang et al. from Kodak Company in the United States used ultra-thin film technology to prepare a light-emitting device with aromatic amines with good hole transport performance as the hole transport layer, an aluminum complex of 8-hydroxyquinoline as the light-emitting layer, and indium tin oxide (ITO) thin film and metal alloy as the anode and cathode respectively. The device achieved a brightness of up to 1000 cd / m at a driving voltage of 10V.2 Green light emission was achieved with a device efficiency of 1.5 lm / W (C.W. Tang and S.A. Van Slyke, Organic electroluminescent diodes, Appl. Phys. Lett., 1987, 51, 913). This breakthrough led to a rapid and in-depth development of organic electroluminescence research worldwide. In 1990, Burroughes et al. at the University of Cambridge proposed the first polymer (PPV)-based light-emitting diode. They demonstrated that PPV could be used as a highly fluorescent emitting material in a single-layer device, with high luminous efficiency (Burroughes JH et al., Light-emitting diodes based on conjugated polymers, Nature, 1990, 347, 539). In 1998, Baldo and Forrest et al. from Princeton University reported the first electroluminescent phosphorescent device, which in principle can have an internal quantum yield of 100% (MA Baldo, DFO'Brienetal., Highly efficient phosphorescent emission from organic electroluminescent devices, Nature, 1998, 395, 151). However, on the one hand, phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive. On the other hand, deep blue phosphorescent materials are still chemically unstable, and the device efficiency rolls off significantly at high current density. Therefore, it is extremely important to develop an OLED device that uses inexpensive and stable organic small molecule materials and can achieve high-efficiency light emission.

[0004] In 2012, the Adachi research group at Kyushu University reported highly efficient all-fluorescent OLED devices based on the thermally activated delayed fluorescence (TADF) mechanism (Uoyama H, Goushi K, Shizu K, et al. Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, 2012, 492(7428):234-238.). When the difference between the S1 and T1 energy levels of a molecule is sufficiently small, triplet excitons can absorb thermal energy, return to the singlet state through a RISC process, and then emit fluorescence. The device's internal quantum efficiency (IQE) can theoretically reach 100%, and its external quantum efficiency (EQE) can even reach 30%, comparable to that of phosphorescent devices. TADF materials, as next-generation luminescent materials, are undergoing rapid research.

[0005] TADF molecules are mainly doped as guest materials in wide bandgap host materials to achieve highly efficient thermally activated delayed fluorescence (Q. Zhang, J. Li, K. Shizu, et al. Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes, J. Am. Chem. Soc. 2012, 134, 14706; H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, 2012, 492, 234; T. Nishimoto, T. Yasuda, et al., A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs, Mater. Horiz., 2014, 1, 264). Unlike traditional fluorescent molecules that emit light from localized states (LE), TADF emission primarily originates from transitions in the ICT state and is therefore susceptible to the influence of donor-acceptor vibrational and rotational motions, resulting in a wider spectrum and a longer lifetime of the delayed fluorescence excited state. This leads to poor stability in electroluminescent devices based on TADF luminescent materials. Although pure organic TADF luminescent materials have broken away from their dependence on precious metals and have the advantage of low cost, their emission spectrum has poor color purity and stability defects, which are the main problems facing organic TADF luminescent materials. Summary of the Invention

[0006] In response to the shortcomings of the prior art, the present invention aims to provide a boron-nitrogen compound and its application. The compound provided by the present invention aims to address the shortcomings of TADF luminescent molecules, providing a luminescent material with a narrow emission spectrum and good stability, which can be used to prepare the light-emitting layer of an organic electroluminescent device, resulting in the organic electroluminescent device exhibiting excellent properties.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In one aspect, the present invention provides a boron-nitrogen compound having a structure shown in Formula I or Formula II below:

[0009]

[0010] R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R a Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R a substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R a substituted diphenylamino groups;

[0011] R a Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R b substituted diphenylamino groups;

[0012] R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R c substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R c substituted diphenylamino groups;

[0013] R c Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more Rd substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R d substituted diphenylamino groups;

[0014] R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or replaced by one or more R e substituted C6-C14 aryl;

[0015] R e Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl;

[0016] R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 and R 18 Independent existence or R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 and R 18 At least one of them forms a ring with the connected aromatic ring;

[0017] R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 Can exist independently or R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 At least one of them forms a ring with the connected aromatic ring;

[0018] R 31 、R 32 、R 33 and R 34 independently selected from H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, one or more Rf Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R f substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R f substituted diphenylamino groups;

[0019] R f Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C18 aryl, g Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R g substituted diphenylamino groups;

[0020] R g Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c substituted C6-C14 aryl, 5- to 18-membered heteroaryl;

[0021] R 31 、R 32 、R 33 and R 34 Exist independently or R 31 、R 32 、R 33 and R 34 At least one of them forms a ring with the connected aromatic ring;

[0022] R 10 and R 20 are independently H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, h Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R h substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R h substituted diphenylamino groups;

[0023] R h Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, or 5- to 18-membered heteroaryl or diphenylamino;

[0024] R iEach occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c substituted C6-C14 aryl, 5- to 18-membered heteroaryl;

[0025] R is H, 6-C14 aryl, one or more R i Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R i substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R i substituted diphenylamino, and when R is H, R 10 Not for H;

[0026] R i Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, 5- to 18-membered heteroaryl, or diphenylamino

[0027] R x1 、R y1 、R x2 and R y2 independently H, D (deuterium), C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R m1 Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R m1 substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R m1 substituted diphenylamino groups;

[0028] R m1 Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, m2 Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R m2 substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R m2 substituted diphenylamino groups;

[0029] R m2 Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or 5- to 18-membered heteroaryl;

[0030] R x1 and R y1Independent existence or R x1 and R y1 form a ring with each other;

[0031] R x2 and R y2 Independent existence or R x2 and R y2 form a ring with each other;

[0032] The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl groups.

[0033] In some embodiments of the present invention, the R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 are independently H, D (deuterium), C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl, C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl.

[0034] Preferably, the R a Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl.

[0035] Preferably, the R b Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl.

[0036] Preferably, the R c Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl.

[0037] Preferably, the R d Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, carbazolyl, at least one C1-C 12 Alkyl-substituted carbazolyl.

[0038] Preferably, the R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R27 and R 28 are independently H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexyloxy, Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

[0039] The wavy lines represent the attachment sites of the groups;

[0040] Preferably, the R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 are independently H, methyl, 2-methyl-phenyl, Phenyl,

[0041] The wavy lines represent the attachment sites of the groups.

[0042] Preferably, R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 At least one of them forms any one of the following ring structures with the connected aromatic ring:

[0043] The bond where * is located is the shared bond with the aromatic ring.

[0044] Preferably, the R 31 、R 32 、R 33 and R 34 independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl;

[0045] Preferably, the R 31 、R 32 、R 33 and R 34 Independently selected from H or phenyl.

[0046] Preferably, the R 31 、R 32 、R 33 and R 34 At least one of them forms any one of the following ring structures with the aromatic ring connected to it:

[0047] The bond where * is located is the shared bond with the aromatic ring.

[0048] Preferably, the R is selected from C6-C18 aryl or 5- to 24-membered heteroaryl;

[0049] Preferably, R is selected from hydrogen, phenyl, Biphenyl,

[0050] Preferably, the R 10 and R 20 independently selected from H, deuterium, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl;

[0051] Preferably, the R 10 and R 20 are independently selected from H, phenyl, pyridyl, phenyl substituted pyridyl, cyano substituted phenyl,

[0052]

[0053] Preferably, the R 31 、R 32 、R 33 and R 34 Independently selected from H, methyl, ethyl, isopropyl, phenyl, biphenyl, carbazolyl, diphenylamino, The wavy lines represent the attachment sites of the groups.

[0054] Preferably, the R 31 、R 32 、R 33 and R 348At least one of them forms any one of the following ring structures with the connected aromatic ring:

[0055] The bond where * is located is the shared bond with the aromatic ring.

[0056] Preferably, R is selected from phenyl or biphenyl;

[0057] Preferably, the R 10 and R 20 are independently selected from hydrogen, deuterium, phenyl or biphenyl.

[0058] In some embodiments of the present invention, the boron nitrogen compound is any one of the following compounds:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] In another aspect, the present invention provides an organic electroluminescent material, comprising the boron nitrogen compound as described above.

[0073] In another aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the boron nitrogen compound as described above.

[0074] Preferably, the organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer and an optional electron injection layer, wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer contains the boron nitrogen compound as described above.

[0075] In the present invention, the boron nitrogen compound having the structure shown in Formula I and Formula II can be used as a functional material in at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer of an organic electroluminescent device.

[0076] In one embodiment, the organic electroluminescent device of the present invention may further include an optional hole blocking layer, an optional electron blocking layer, an optional capping layer, and the like.

[0077] In one embodiment, the organic electroluminescent device has Figure 1 In the structure shown, 1 is an ITO anode, 2 is a first hole transport layer, 3 is a second hole transport layer, 4 is a light-emitting layer, 5 is a second electron transport layer, 6 is a first electron transport layer, 7 is an electron injection layer, and 8 is a metal cathode.

[0078] In one embodiment, the boron nitrogen compounds having the structures shown in Formula I and Formula II are used to prepare the light-emitting layer in an organic electroluminescent device.

[0079] In one embodiment, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer containing the boron nitrogen compound as described above, and may further comprise any one or a combination of multiple of 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.

[0080] In another aspect, the present invention provides an organic electroluminescent composition comprising the boron nitrogen compound as described above as a doping material and a host material;

[0081] Preferably, the host material is a material having electron transport capability and / or hole transport capability and having triplet excited state energy equal to or higher than triplet excited state energy of the dopant material.

[0082] In one embodiment of the present invention, the host material is a carbazole derivative and / or a carboline derivative having a structure as shown in any one of Formula (H-1) to Formula (H-10):

[0083]

[0084]

[0085] wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N;

[0086] where R 1H and R 2H Independently any of the following groups:

[0087]

[0088] wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N;

[0089] where R aH and R bH are independently H, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or C1-C 20 Alkoxy-substituted C6-C 20 Aryl, * represents the attachment site of the group;

[0090] W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 independently S or O;

[0091] R 3H 、R 4H 、R 5H 、R 6H 、R 7H 、R 8H 、R 9H 、R 10H 、R 11H 、R 12H 、R 13H and R 14H are independently H, deuterium, C1-C6 alkyl or C6-C24 aryl.

[0092] In one embodiment of the present invention, the organic electroluminescent composition preferably contains 0.3-30.0 wt% (e.g., 0.3 wt%, 0.5 wt%, 1 wt%, 3 wt%, 5 wt%, 8 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt%, 23 wt%, 25 wt%, 28 wt% or 30 wt%) of the boron nitrogen compound described above as a dopant material, and the remaining 99.7-70.0 wt% (e.g., 99.7 wt%, 99 wt%, 98 wt%, 95 wt%, 93 wt%, 90 wt%, 88 wt%, 85 wt%, 83 wt%, 80 wt%, 78 wt% or 77 wt%) of the component is a host material composed of 1-2 compounds having structures of Formula (H-1) to (H-10);

[0093] In one embodiment of the present invention, the main material contains two compounds having structures of formula (H-1) to formula (H-10), and the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0094] Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254;

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] In one embodiment of the present invention, the organic electroluminescent composition contains 0.3-30.0 wt% (for example, the weight percentage can be 0.3 wt%, 0.5 wt%, 1 wt%, 3 wt%, 5 wt%, 8 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt%, 23 wt%, 25 wt%, 28 wt% or 30 wt%) of the boron nitrogen compounds of the structures represented by Formula I and Formula II as described above, and the remaining 99.7-70.0 wt% (for example, 99.7 wt%, 99 wt%, 98 wt%, 95 wt%, 93 wt%, 90 wt%, 88 wt%, 85 wt%, 83 wt%, 80 wt%, 78 wt% or 77 wt%) of the ingredients are one or two compounds selected from Compounds H1-1 to H1-254.

[0106] In a preferred embodiment of the present invention, the organic electroluminescent composition contains two compounds of compounds H1-1 to H1-254 as host materials, and the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0107] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds having the structures shown in Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds shown in Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds having the structures shown in Formulas H-1 to H-10.

[0108] In a preferred embodiment, the amount ratio between the compound represented by Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compound represented by H-1, H-2, H-3, H-4, H-5H-6, H-7, H-8, H9 or H-10 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0109]

[0110] where R 1a 、R 1b 、R 2a 、R 2b 、R3a and R 3b One or two of them are independently R Tz , the rest are the same or different and are independently hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 C6-C8 substituted aryl or C1-C8 alkoxy 18 Aryl; R Tz is any one of the substituent groups shown below:

[0111]

[0112]

[0113] The asterisk represents the attachment site of the group;

[0114] In a preferred embodiment, the weight ratio of the compounds represented by formulae TRZ-1 to TRZ-86 in the host material to the carbazole or carbazole derivative having a structure represented by any one of formulae (H-1) to (H-10) is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0115] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds of Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds shown in Formulas H-1 to H-10. For example, in the host material, the weight ratio between the Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0116] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives represented by Formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by Formulas H1-1 to H1-254. For example, in the host material, the weight ratio of the 1,3,5-triazine derivative to the carbazole or carbline derivative is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0117] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A and any one of the carbazole or carbazole derivatives represented by formulas H1-1 to H1-254. For example, in the host material, the weight ratio between the compounds of formulae Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carbazole derivatives of formulae H1-1 to H1-254 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0118] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives represented by formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254. For example, in the host material, the weight ratio of the 1,3,5-triazine derivative represented by Formulas TRZ-1 to TRZ-86 to the carbazole or carbline derivative represented by Formulas H1-1 to H1-254 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0119]

[0120]

[0121]

[0122]

[0123] In the present invention, in the organic electroluminescent composition, the host material is composed of any one of the compounds having the structures represented by formulas H-1 to H-10 and any one of the compounds represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6.

[0124]

[0125]

[0126] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur);

[0127] R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl;

[0128] R si(i=7-39) are independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl;

[0129] Preferably, R s1 、R s2 、R s3 、R s4 、R s5 and R s6 Independently selected from any of the following 24 groups:

[0130]

[0131] The asterisk represents the attachment site of the group.

[0132] Preferably, R si (i=7-39) are independently selected from any one of the following five groups:

[0133] The asterisk represents the attachment site of the group.

[0134] Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds having structures represented by formula I and formula II, and the host material is any one of the compounds represented by formulas 2CN-1 to 2CN-60 and any one of the compounds represented by formulas H1-1 to H1-254;

[0135]

[0136]

[0137]

[0138] In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the main material in the organic electroluminescent composition can be a carbazole derivative and / or a carbidine derivative as shown in Formula (H-1) to Formula (H-10). In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0wt% of any compound shown in Formula I and Formula II, and the remaining 99.7-70.0wt% of the components are a main body composed of 1-2 compounds having the structures of Formula (H-1) to Formula (H-10). For example, when the main body contains 2 compounds having the structures of Formula (H-1) to Formula (H-10), the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0139] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the host material in the composition is one or two compounds selected from compounds H1-1 to H1-254. In a preferred embodiment, the organic electroluminescent composition comprises 0.3-30.0 wt% of any compound of Formula I, and the remaining 99.7-70.0 wt% comprises one or two compounds selected from compounds H1-1 to H1-254. For example, when the composition comprises two compounds selected from formulas H1-1 to H1-254, the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0140] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by Formulas H-1 to H-10. For example, in the host material, the weight ratio between the Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0141] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives represented by Formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by Formulas H1-1 to H1-254. For example, in the host material, the weight ratio of the 1,3,5-triazine derivative to the carbazole or carbline derivative is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0142] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of the carbazole or carbazole derivatives represented by formulas H1-1 to H1-254. For example, in the host material, the weight ratio between the compounds of formulae Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carbazole derivatives of formulae H1-1 to H1-254 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0143] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the compounds of Formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds shown in Formulas H-1 to H-10. For example, in the host material, the weight ratio between the Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0144] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the dicyanobenzene derivatives represented by Formulas 2CN-1 to 2CN-60 and any one of the carbazole or carboline derivatives represented by Formulas H1-1 to H1-254. For example, in the host material, the weight ratio of the dicyanobenzene derivative to the carbazole or carbline derivative is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0145] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3wt%-30.0wt%); and the host material (content is 99.7wt%-70.0wt%) is composed of any one of the compounds represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5, or Ph-2CN-6 and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254. For example, in the host material, the weight ratio of the compound represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5, or Ph-2CN-6 to the carbazole or carboline derivative represented by formulas H1-1 to H1-254 is 1:20 to 20:1.

[0146] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3wt-30.0wt%), and the main material (content is 99.7wt-70.0wt%) is composed of any one of the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254. For example, in the host material, the weight ratio between the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and the carbazole or carbazole derivatives represented by formulas H1-1 to H1-254 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0147] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content is 0.3wt-30.0wt%), and the main material (content is 99.7wt-70.0wt%) is composed of any one of the carbazole or carbidine derivatives shown in Formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir or Pt as shown in Formulas Ir-1, Ir-2 and Pt-1. For example, in the host material, the weight ratio between the carbazole or carbazole derivative as shown in Formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0148]

[0149]

[0150] R ri are independently hydrogen, deuterium, C1-C18 alkyl, or C6-C18 aryl, wherein i is an integer from 1 to 22, and wherein the dashed line represents that two of the four bonds included are double bonds;

[0151] R ri Any of the groups can form a ring with the aromatic ring or aromatic heterocycle to which it is connected;

[0152] Preferably, the phosphorescent compound containing metal Ir is any one of the following compounds:

[0153]

[0154] In one embodiment of the present invention, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288 (content is 0.3 wt% to 30.0 wt%), and the host material (content is 99.7 wt% to 70.0 wt%) is composed of any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 and the phosphorescent compounds containing metal Ir represented by formulas Ir-1 and Ir-2. For example, in the host material, the weight ratio of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 to the phosphorescent compound containing metal Ir is 1:20 to 20:1.

[0155] In another aspect, the present invention provides an organic electroluminescent material, comprising the organic electroluminescent composition as described above.

[0156] In another aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the organic electroluminescent composition as described above.

[0157] Preferably, the organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, and an optional electron injection layer, wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer contains the organic electroluminescent composition as described above.

[0158] In the present invention, the organic electroluminescent composition can be used as a functional material in at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer and hole injection layer of an organic electroluminescent device.

[0159] In one embodiment of the present invention, the material of the light-emitting layer in the organic electroluminescent device comprises the organic electroluminescent composition as described above.

[0160] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on energy transfer from the host material to any compound represented by Formula I and Formula II or carrier capture by the light-emitting material itself.

[0161] In one embodiment of the present invention, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer comprising the organic electroluminescent composition as described above, and may further comprise any one of 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, or a combination of at least two thereof.

[0162] In another aspect, the present invention provides a use of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0163] Terminology

[0164] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

[0165] As used herein, the terms "comprising" or "including" may be open, semi-closed, or closed. In other words, the terms also include "consisting essentially of" or "consisting of."

[0166] Group Definition

[0167] In this specification, groups and substituents thereof can be selected by those skilled in the art to provide stable structural moieties and compounds. When substituents are described by conventional chemical formulas written from left to right, the substituents also include chemically equivalent substituents obtained when the structural formula is written from right to left.

[0168] The section headings used in this specification are for organizational purposes only and should not be construed as limitations on the subject matter described. All documents or portions of documents cited in this specification, including but not limited to patents, patent applications, articles, books, manuals, and papers, are incorporated herein by reference in their entirety.

[0169] Unless otherwise specified, all technical and scientific terms used herein have the standard meanings in the art to which the claimed subject matter belongs. If there are multiple definitions for a term, the definition herein shall prevail.

[0170] It should be understood that the singular forms used in the present invention, such as "a", include plural references unless otherwise specified. In addition, the term "comprising" is an open limitation rather than a closed limitation, that is, it includes the content specified in the present invention, but does not exclude other aspects of the content.

[0171] Unless otherwise stated, the present invention adopts conventional methods of mass spectrometry and elemental analysis, and each step and condition can refer to conventional operating steps and conditions in the art.

[0172] Unless otherwise indicated, the present invention employs standard nomenclature and standard laboratory procedures and techniques for analytical chemistry, synthetic organic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and light-emitting device performance testing.

[0173] The compounds of the present invention may contain unnatural ratios of atomic isotopes on one or more of the atoms constituting the compounds. For example, radioactive isotope-labeled compounds may be used, such as deuterium (2H). All isotopic variations of the compounds of the present invention, whether radioactive or not, are encompassed within the scope of the present invention.

[0174] In the present invention, unless otherwise specified, the number of "substituted" can be one or more; when "plural," it means two or more, for example, 2, 3, or 4. Furthermore, when the number of "substituted" is multiple, the "substituted" can be the same or different. In the present invention, the position of "substituted" can be any position unless otherwise specified.

[0175] In the present invention, the term "alkyl" as a group or part of other groups (such as in groups such as halogen-substituted alkyl) means a saturated aliphatic hydrocarbon group including branched and straight chains having the specified number of carbon atoms. For example, C1-C20 Alkyl groups include linear or branched alkyl groups having 1 to 20 carbon atoms. As defined in "C1-C6 alkyl," these include groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched structure. For example, in the present invention, the C1-C6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; wherein, propyl is a C3 alkyl group (including isomers, such as n-propyl or isopropyl); butyl is a C4 alkyl group (including isomers, such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is a C5 alkyl group (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl, or neopentyl); and hexyl is a C6 alkyl group (including isomers, such as n-hexyl or isohexyl).

[0176] The term "alkoxy" as used herein refers to an alkyl group as defined above attached via an oxygen linkage (-O-).

[0177] In the present invention, the term "Cn-m aryl" as a group or part of another group refers to a monocyclic or polycyclic aromatic group having n to m ring carbon atoms (ring atoms are only carbon atoms), which has at least one carbon ring with a conjugated π electron system. Examples of the above-mentioned aryl units include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthrenyl, or anthracenyl. In one embodiment, the aryl is preferably a C6-14 aryl, such as phenyl and naphthyl, more preferably phenyl.

[0178] In the present invention, as a group or part of other groups, the term "nm-membered heteroaryl" refers to an aromatic group whose ring atoms contain one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, and whose ring atoms are n to m, and the heteroaryl is a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, wherein at least one ring is aromatic. Heteroaryl groups within the scope of this definition include, but are not limited to, acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thienyl, benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridinyl, thienopyridinyl, furopyridinyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, preferred examples of the “5- to 18-membered heteroaryl” include furanyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyrimidinyl, and carbazolyl, with carbazolyl being more preferred.

[0179] As used herein, the term Cn-Cm cycloalkyl refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as 3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicycloheptyl. In one embodiment, the C3-C10 cycloalkyl group is preferably adamantyl or cyclohexyl.

[0180] In the present invention, the limited carbon number range of the group means any integer number of carbon atoms included in the limited range, such as C1 to C 20 The number of carbon atoms in the group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20. 10 It means that the number of carbon atoms in the group can be 3, 4, 5, 6, 7, 8, 9 or 10, and the limited carbon number ranges of other groups are similar.

[0181] Without violating the common sense in the art, the above-mentioned preferred conditions can be arbitrarily combined to obtain preferred embodiments of the present invention.

[0182] The reagents and raw materials used in the present invention are commercially available.

[0183] Compared with the prior art, the present invention has the following beneficial effects:

[0184] By extending conjugation and introducing nitrogen atoms, the boron-nitrogen compound of the present invention not only achieves fine-tuning of the spectrum but also further improves luminescence efficiency. The boron-nitrogen compound of the present invention exhibits a narrow spectrum and is used as a narrow-spectrum luminescent material in the preparation of the light-emitting layer of an organic electroluminescent device. The organic electroluminescent device produced in this manner achieves narrow-spectrum TADF emission, with an electroluminescence spectrum in the green-yellow region and a half-width at half maximum of less than 45 nm. Furthermore, the device achieves a maximum external quantum efficiency of over 30% for electroluminescence. BRIEF DESCRIPTION OF THE DRAWINGS

[0185] Figure 1 Schematic diagram of the structure of the organic electroluminescent device of the present invention, wherein 1 is an ITO anode, 2 is a first hole transport layer, 3 is a second hole transport layer, 4 is a light-emitting layer, 5 is a second electron transport layer, 6 is a first electron transport layer, 7 is an electron injection layer, and 8 is a metal cathode.

[0186] Figure 2 This is the photoluminescence spectrum of compound BN-17. DETAILED DESCRIPTION

[0187] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0188] In the embodiments of the present invention, the raw materials used to synthesize the compounds shown are as follows:

[0189] The specific initial general raw materials used include the following molecules: The specific raw material 1 used includes the following molecules:

[0190]

[0191] The raw materials 2 specifically used include the following molecules:

[0192]

[0193] The raw materials 3 specifically used include the following molecules:

[0194]

[0195] The raw materials 4 specifically used include the following molecules:

[0196]

[0197] For the synthesis of the compound represented by Formula I, when one of R or R10 is H, the synthetic route and specific operations are as follows:

[0198]

[0199] First, 1,5-dibromo-2,4-difluorobenzene or 1,2-dibromo-3,5-difluorobenzene is modified with arylboronic acid starting materials through a simple Suzuki reaction to obtain the corresponding intermediates Ai(M) (i=1-10) or Bj(P) (j=1-12). Subsequently, a carbazole derivative is introduced through an aryl nucleophilic substitution reaction to obtain the intermediates Ckm(M) or Ckm(P) (k, m=1-16). The intermediates (Ckm(M) or Ckm(P) (k, m=1-16)) treated with n-butyllithium are then mixed with a benzophenone derivative (Dx) (x=1-5) and stirred thoroughly to obtain the hydroxy intermediate. This hydroxy intermediate undergoes intramolecular dehydration cyclization under acidic conditions without further purification to generate Dx(M) or Dx(P) (x=1-5). On this basis, NBS is further brominated to yield the intermediate Br(M) or Br(P), and finally, a one-pot lithiation-boration-cyclization cascade reaction yields the final product, BN-n(M) or BN-n(P) (n=1-192), respectively. The structural difference between BN-n(M) and BN-n(P) (n=1-192) lies primarily in the location of the aromatic ring modification at the resonance core. Their synthesis methods are similar, so the synthesis of BN-n(M) (n=1-192) will be used as an example.

[0200] In the first step, 100.0 mmol of raw material Ai (i = 1-10), 1,5-dibromo-2,4-difluorobenzene (100.0 mmol), potassium carbonate (200.0 mmol), and 200 mg of tetrakistriphenylphosphine palladium were added to 200 mL of tetrahydrofuran and 50 mL of water. The reaction system was refluxed and stirred under a nitrogen atmosphere for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain intermediate Ai (M) (i = 1-10).

[0201] In the second step, 50.0 mmol of raw material Ai(M) (i=1-10), 50.0 mmol of raw material Ck (k=1-16), and cesium carbonate (75.0 mmol) were added to 250 mL of anhydrous DMF (N,N-dimethylformamide), and the reaction system was stirred at 160°C for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain intermediate F-Ck(M) (k=1-16).

[0202] In the third step, 40.0 mmol of raw material F-Ck(M) (k=1-16), 40.0 mmol of raw material Cm (m=1-16), and cesium carbonate (80.0 mmol) were added to 200 mL of anhydrous DMF, and the reaction system was stirred at 160°C for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain the intermediate Ckm(M) (k, m=1-16).

[0203] In the fourth step, under the protection of a nitrogen atmosphere, 36mmol of a hexane solution of n-butyllithium is slowly added to a 200mL tetrahydrofuran solution (-30°C) containing 30mmol of the intermediate Ckm(M) (k, m = 1-16), and the reaction is carried out at this temperature for 1 hour. Subsequently, a tetrahydrofuran solution of the raw material Dx (x = 1-5) is slowly added, and the system is stirred at room temperature for 24 hours. The reaction mixture is extracted with dichloromethane and an aqueous ammonium chloride solution, and the organic phase is heated and dried under vacuum to obtain a hydroxy intermediate. After dissolving it with dichloromethane, 300mmol of methanesulfonic acid is slowly added while stirring at room temperature, and the reaction is continued at room temperature for 6 hours. The reaction mixture is then extracted with dichloromethane and an aqueous solution, and the organic phase is heated and dried under vacuum to obtain the intermediate Dx(M) (x = 1-5).

[0204] In the fifth step, 20.0 mmol of the first-class compound Dx(M) (x = 1-5) was dissolved in 100 mL of dry chloroform. N-bromosuccinimide (NBS, 20.0 mmol) was slowly added to the above system under an ice-water bath. Liquid nitrogen was degassed for 30 minutes. The reaction mixture was then slowly warmed to room temperature and the reaction was continued for 6 hours in the dark. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried by heating under vacuum and then purified by column chromatography to obtain the precursor Br(M).

[0205] In the sixth step, 11 mmol of n-butyllithium in hexane was slowly added to a 100 mL tert-butylbenzene solution containing 10.0 mmol of intermediate Br(M) at -30°C. The mixture was slowly heated to room temperature and stirred for 2 hours, then cooled to -30°C, and 10.0 mmol of boron tribromide was added. The reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIEA, 20.0 mmol) was then added at 0°C, and the reaction mixture was heated to 130°C and stirred for 12 hours before being cooled to room temperature. 5 mL of methanol was added to the reaction mixture to quench the residual boron tribromide. The reaction system was concentrated in vacuo and purified by column chromatography using a mixture of dichloromethane / petroleum ether as the eluent to obtain the target product BN-n(M) (n=1-192).

[0206] For the synthesis of compounds represented by formula I, when R and R 10When all are not H, the synthetic route and specific operation are as follows:

[0207]

[0208] Specific compound synthesis reaction route:

[0209] Based on BN-n(P), the intermediate Br-BN-n(P) was obtained through NBS bromination reaction, and finally, after a simple Suzuki reaction, it was coupled with an arylboronic acid compound to obtain the final product BN-n(MP).

[0210] In the first step, 30.0 mmol of compound BN-n(P) was dissolved in 100 ml of dry dichloromethane. 30.0 mmol of NBS was slowly added to the above system under an ice-water bath. Liquid nitrogen was degassed for 30 minutes. The temperature was then slowly warmed to room temperature and the reaction was continued for 4 hours. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried by heating under vacuum and then purified by column chromatography to obtain the intermediate Br-BN-n(P).

[0211] In the second step, arylboronic acid compound Ai (i = 1-6) (24.0 mmol), Br-BN-n (P) (20.0 mmol), and 40.0 mmol potassium phosphate were added to dry toluene (100 ml). The mixture was bubbled with nitrogen for 10 minutes, and 0.2 mmol of trisdibenzylidene palladium and 0.4 mmol of s-Phos were added under high nitrogen flow. The mixture was heated to 90 ° C and stirred for 16 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain the final product BN-n (MP).

[0212] The relevant data of the obtained target compounds are shown in Table 1.

[0213] The specific details of the synthesis example experiment are described using compound BN-17 as an example:

[0214] In the first step, 12.2 g of raw material A1 (100.0 mmol), 27.2 g of raw material 1,5-dibromo-2,4-difluorobenzene (100 mmol), 27.6 g of potassium carbonate (200.0 mmol) and 200 mg of tetrakistriphenylphosphine palladium were added to 200 mL of tetrahydrofuran and 50 mL of water. The reaction system was refluxed and stirred under a nitrogen atmosphere for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then further purified by column chromatography using petroleum ether as eluent to obtain white solid A1 (M) with a yield of 55%.

[0215] In the second step, 14.0 g of raw material C1 (50.0 mmol), 13.5 g of raw material A1 (50.0 mmol), and 24.5 g of cesium carbonate (75.0 mmol) were added to 200 mL of anhydrous N,N-dimethylformamide (DMF), and the reaction system was stirred at 160° C. for 12 hours, then cooled to room temperature, and further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate F-C1(M) as a white solid with a yield of 73%.

[0216] In the third step, 15.9 g of raw material F-C1(M) (30.0 mmol), 8.4 g of raw material C1 (30.0 mmol), and 19.6 g of cesium carbonate (60.0 mmol) were added to 200 mL of anhydrous DMF, and the reaction system was stirred at 160° C. for 12 hours, then cooled to room temperature, and further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate C11(M) as a white solid with a yield of 92%.

[0217] In the fourth step, under nitrogen atmosphere protection, 30mmol of n-butyl lithium in hexane solution was slowly added to 150mL of tetrahydrofuran solution containing 19.7g of intermediate C11 (M) (25mmol) (-30 ℃), and reacted at this temperature for 1 hour. Subsequently, a tetrahydrofuran solution of raw material D5 was slowly added, and the system was stirred at room temperature for 24 hours. The reaction mixture was extracted with dichloromethane and aqueous ammonium chloride solution, and the organic phase was heated and dried under vacuum to obtain a hydroxy intermediate. Subsequently, after dissolving it with dichloromethane, 250mmol of methylsulfonic acid was slowly added while stirring at room temperature, and the reaction continued at room temperature for 6 hours. Subsequently, the reaction mixture was extracted with dichloromethane and aqueous solution, and the organic phase was heated and dried under vacuum to obtain white intermediate D5 (M), with a yield of 64%.

[0218] In the fifth step, 15.0 mmol of the first compound D5(M) was dissolved in 100 mL of dry chloroform. NBS (15.0 mmol) was slowly added to the above system under an ice-water bath. Liquid nitrogen was degassed for 30 minutes. The mixture was then slowly warmed to room temperature and the reaction was continued for 6 hours in strict darkness. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried by heating under vacuum and then purified by column chromatography to obtain Br(M) as a white solid in a 93% yield.

[0219] In the sixth step, 11 mmol of n-butyllithium in hexane was slowly added to a 100 mL tert-butylbenzene solution containing 10.0 mmol of intermediate Br(M) at -30°C. The mixture was slowly heated to room temperature and stirred for 2 hours, then cooled to -30°C. 2.5 g of boron tribromide (10.0 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. 2.6 g of DIEA (20.0 mmol) was then added at 0°C, and the reaction mixture was heated to 130°C and stirred for 12 hours before being cooled to room temperature. 5 mL of methanol was added to the reaction mixture to quench the residual boron tribromide. The reaction system was concentrated in vacuo and purified by column chromatography using a mixture of dichloromethane and petroleum ether as the eluent to obtain the yellow target product BN-17(M) in a yield of 38.9%.

[0220] For the synthesis of the compound represented by formula II, the synthetic route and specific operations adopted are as follows:

[0221]

[0222] First, 1,5-dibromo-2,4-difluorobenzene is modified with an arylboronic acid starting material through a simple Suzuki reaction to obtain the corresponding intermediate Ai(II) (i=1-10). Subsequently, a carbazole derivative is introduced through an aryl nucleophilic substitution reaction to obtain the intermediate Ckm(II) (k=1-16). The intermediate Ckm(II) (k=1-16) treated with n-butyllithium is then mixed with a benzophenone derivative Dx(II) (x=1-5) and stirred thoroughly to obtain the hydroxy intermediate. This hydroxy intermediate undergoes intramolecular dehydration cyclization under acidic conditions without further purification to generate Dx(II) (x=1-5). On this basis, NBS was further brominated to obtain the intermediate Br-n(II) (n=193-288), followed by a one-pot lithiation-boration-cyclization cascade reaction to obtain the intermediate Bn(II) (n=193-288), and finally the final product BN-n(II) (n=193-288) was obtained through an oxidative coupling reaction.

[0223] In the first step, 100.0 mmol of raw material Ai (i = 1-10), 1,5-dibromo-2,4-difluorobenzene (100.0 mmol), potassium carbonate (200.0 mmol), and 200 mg of tetrakistriphenylphosphine palladium were added to 200 mL of tetrahydrofuran and 50 mL of water. The reaction system was refluxed and stirred under a nitrogen atmosphere for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain intermediate Ai (II) (i = 1-10).

[0224] In the second step, 50.0 mmol of raw material Ai(II) (i=1-10), 50.0 mmol of raw material Ck, and cesium carbonate (75.0 mmol) were added to 250 mL of anhydrous DMF (N,N-dimethylformamide), and the reaction system was stirred at 160°C for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain intermediate F-Ck(II) (k=1-16).

[0225] In the third step, 40.0 mmol of raw material F-Ck(II) (k=1-16), 40.0 mmol of raw material Cm (m=1-16), and cesium carbonate (80.0 mmol) were added to 200 mL of anhydrous DMF, and the reaction system was stirred at 160°C for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography to obtain the intermediate Ckm(II) (k, m=1-16).

[0226] In the fourth step, under the protection of a nitrogen atmosphere, 36mmol of a hexane solution of n-butyllithium is slowly added to a 200mL tetrahydrofuran solution (-30°C) containing 30mmol of the intermediate Ckm(II) (k, m = 1-16), and the reaction is carried out at this temperature for 1 hour. Subsequently, a tetrahydrofuran solution of the raw material Dx (x = 1-5) (30mmol) is slowly added, and the system is stirred at room temperature for 24 hours. The reaction mixture is extracted with dichloromethane and an aqueous ammonium chloride solution, and the organic phase is heated and dried under vacuum to obtain a hydroxy intermediate. After dissolving it with dichloromethane, 300mmol of methanesulfonic acid is slowly added while stirring at room temperature, and the reaction is continued at room temperature for 6 hours. The reaction mixture is then extracted with dichloromethane and an aqueous solution, and the organic phase is heated and dried under vacuum to obtain the intermediate Dx(II) (x = 1-5).

[0227] In the fifth step, 20.0 mmol of the intermediate Dx(II) (x = 1-5) was dissolved in 100 mL of dry chloroform. N-bromosuccinimide (NBS, 20.0 mmol) was slowly added to the above system under an ice-water bath. Liquid nitrogen was degassed for 30 minutes. The reaction mixture was then slowly warmed to room temperature and the reaction was continued for 6 hours in strict darkness. The reaction mixture was extracted with dichloromethane and water, and the organic phase was dried by heating under vacuum and then purified by column chromatography to obtain the intermediate Br-n(II) (n = 193-288).

[0228] In the sixth step, 11 mmol of n-butyllithium in hexane was slowly added to a 100 mL tert-butylbenzene solution containing 10.0 mmol of the intermediate Br-n(II) (n=193-288) at -30°C. The temperature was slowly raised to room temperature and stirred for 2 hours, then cooled to -30°C, and 10.0 mmol of boron tribromide was added. The reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIEA, 20.0 mmol) was then added at 0°C, and the reaction mixture was heated to 130°C and stirred for 12 hours before being cooled to room temperature. 5 mL of methanol was added to the reaction mixture to quench the residual boron tribromide. The reaction system was concentrated in vacuo and purified by column chromatography using a mixture of dichloromethane and petroleum ether as the eluent to obtain the precursor Bn(II) (n=193-288).

[0229] In the seventh step, 2.5 mmol of the precursor Bn(II) (n=193-288) and 862.6 mg of DDQ (3.8 mmol) were dissolved in 75 mL of dry dichloromethane. The mixture was sparged with nitrogen for 10 minutes and stirred at room temperature for 10 minutes. Then, 0.6 mL of methanesulfonic acid (MsOH) was added dropwise at 0°C, and the mixture was stirred at room temperature for another 3 hours. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried by heating under vacuum and then purified by column chromatography to obtain the target product BN-n(II) (n=193-288).

[0230] The relevant data of the obtained target compounds are shown in Table 1.

[0231] The specific details of the synthesis example experiment are described using compound BN-273 as an example:

[0232] In the first step, 36.0 g of raw material A9 (100.0 mmol), 27.2 g of raw material 1,5-dibromo-2,4-difluorobenzene (100 mmol), 27.6 g of potassium carbonate (200.0 mmol) and 200 mg of tetrakistriphenylphosphine palladium were added to 200 mL of tetrahydrofuran and 50 mL of water. The reaction system was refluxed and stirred under a nitrogen atmosphere for 12 hours, then cooled to room temperature, and the reaction mixture was extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then further purified by column chromatography using petroleum ether as eluent to obtain white solid A9(II) with a yield of 74%.

[0233] In the second step, 14.0 g of raw material C1 (50.0 mmol), 25.4 g of raw material A1 (50.0 mmol), and 24.5 g of cesium carbonate (75.0 mmol) were added to 200 mL of anhydrous N,N-dimethylformamide (DMF), and the reaction system was stirred at 160° C. for 12 hours, then cooled to room temperature, and further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate F-C1(II) as a white solid with a yield of 85%.

[0234] In the third step, 11.2 g of raw material C1 (40.0 mmol), 30.7 g of raw material F-C1(II) (40.0 mmol), and 26.1 g of cesium carbonate (80.0 mmol) were added to 200 mL of anhydrous DMF, and the reaction system was stirred at 160° C. for 12 hours, then cooled to room temperature, and further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate C11(II) as a white solid with a yield of 94%.

[0235] In the fourth step, under nitrogen atmosphere protection, the hexane solution of 36mmol n-butyl lithium is slowly added to the 200mL tetrahydrofuran solution containing 30.8g intermediate C11 (II) (30mmol) (-30 ℃), and reacted at this temperature for 1 hour. Subsequently, the tetrahydrofuran solution of 5.4g raw material D5 (30mmol) is slowly added, and the system is stirred at room temperature for 24 hours. With dichloromethane and aqueous ammonium chloride extraction reaction mixture, heat the spin-dried organic phase under vacuum to obtain the hydroxy intermediate. Subsequently, after being dissolved with dichloromethane, 300mmol methylsulfonic acid is slowly added under stirring at room temperature, and room temperature continues reaction for 6 hours. With dichloromethane and aqueous solution extraction reaction mixture, heat the spin-dried organic phase under vacuum to obtain intermediate D5 (II), productive rate 70%.

[0236] In the fifth step, 22.2g of intermediate D5 (II) (20.0mmol) was dissolved in 100mL of dry chloroform, and 3.56g of NBS (20.0mmol) was slowly added to the above system under an ice-water bath. Liquid nitrogen was degassed and replaced for 30 minutes. The reaction was slowly warmed to room temperature and the reaction was continued for 6 hours in strict luminophore. The reaction mixture was extracted with dichloromethane and water, and the organic phase was heated under vacuum and then purified by column chromatography to obtain Br-273 (II) as a white solid in an 84% yield.

[0237] In the sixth step, 11 mmol of n-butyl lithium in hexane was slowly added to a 100 mL tert-butylbenzene solution (-30 ° C) containing 11.9 g of intermediate Br-273 (II) (10.0 mmol). The temperature was slowly raised to room temperature and stirred for 2 hours, then cooled to -30 ° C, 2.5 g of boron tribromide (10.0 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then 2.6 g of DIEA (20.0 mmol) was added at 0 ° C, and the reaction mixture was heated to 130 ° C and continued to stir for 12 hours, and then cooled to room temperature. 5 mL of methanol was added to the reaction mixture to quench the residual boron tribromide. The reaction system was concentrated in vacuo and purified by column chromatography with a mixture of dichloromethane / petroleum ether to obtain a yellow precursor B-273 (II) with a yield of 47%.

[0238] In the seventh step, 2.79 g of precursor B-273(II) (2.5 mmol) and 862.6 mg of DDQ (3.8 mmol) were dissolved in 75 mL of dry dichloromethane. The mixture was sparged with nitrogen for 10 minutes and stirred at room temperature for 10 minutes. Then, 0.6 mL of methanesulfonic acid (MsOH) was added dropwise at 0°C, and the mixture was stirred at room temperature for another 3 hours. The reaction mixture was extracted with dichloromethane and water, and the organic phase was dried by heating under vacuum and then purified by column chromatography to obtain the yellow target product BN-273(II) in a 42.0% yield.

[0239] The product was characterized using an Agilent VarioMicro Cube instrument for elemental analysis, testing for C, H, N, and S. Mass spectrometry was performed using a Thermo Fisher TSQEndura ultra-high performance liquid chromatography coupled to a triple quadrupole mass spectrometer.

[0240] The results of the photoluminescence test of the compounds showed that: taking compound BN-17 as an example, the compound was in a toluene solution (1×10 -5 M) are 518 nm and the half-peak width is 30 nm (e.g. Figure 2 shown).

[0241] Table 1. Summary of product data in synthetic examples

[0242]

[0243]

[0244] Electroluminescent device embodiments

[0245] Some representative examples of electroluminescent devices are given below. The molecular structures of some materials involved in the device examples and comparative examples are as follows:

[0246]

[0247]

[0248]

[0249] The following is an example of an electroluminescent device prepared using the material of the present invention. The specific device preparation process is as follows:

[0250] Organic electroluminescent device preparation process:

[0251] The results of the device are as follows Figure 1 As shown, 1 is the ITO anode, 2 is the first hole transport layer, 3 is the second hole transport layer, 4 is the light-emitting layer, 5 is the second electron transport layer, 6 is the first electron transport layer, 7 is the electron injection layer, and 8 is the metal cathode.

[0252] The preparation process is as follows:

[0253] (1) Substrate treatment: Transparent ITO glass was used as the substrate material for device preparation. It was first ultrasonically treated with a 5% ITO solution for 30 minutes, then ultrasonically cleaned with distilled water (twice), acetone (twice), and isopropyl alcohol (twice). Finally, the ITO glass was stored in isopropyl alcohol. Before each use, the ITO glass surface was carefully wiped with acetone and isopropyl alcohol cotton balls, rinsed with isopropyl alcohol, dried, and then plasma treated for 5 minutes before use. The device was prepared by combining spin coating and vacuum evaporation processes.

[0254] (2) Preparation of hole injection layer and hole transport layer: The hole transport layer was prepared by evaporation process. When the vacuum degree of vacuum evaporation system reached 5×10 -4 Pa below, the deposition rate was measured by the film thickness meter. The organic hole transport layer was deposited on the surface of the ITO electrode in sequence using the vacuum evaporation process. The deposition rate of the hole transport material was

[0255] (3) Preparation of the luminescent layer: The luminescent layer was prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reached 5×10 - 4 Pa below, the deposition rate was measured by the film thickness meter. The light-emitting layer was deposited on the hole transport layer in sequence using a vacuum evaporation process. The deposition rate of the light-emitting layer material was

[0256] (4) Preparation of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are prepared by evaporation process. When the vacuum degree of vacuum evaporation system reaches 5×10 -4When the thickness is below Pa, the deposition begins, and the deposition rate is measured by a film thickness meter. The organic electron transport layer, the LiF electron injection layer, and the metal Al electrode are sequentially deposited on the light-emitting layer using a vacuum deposition process (see the following embodiment for the specific device structure). The deposition rate of the organic material is The deposition rate of LiF is The deposition rate of Al is Device Example 1-n (n=73)

[0257] In the device examples 1-n (n=1-73), the organic electroluminescent device (structure as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-1 is used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the device effect embodiment is [ITO / 15wt% HIM+85wt% HTL-1 (100nm) / HTL-2 (10nm) / 99wt% H1-1+1wt% BN-m (30nm) / TRZ-83 (10nm) / TRZ-85 (30nm)LiF (1nm) / Al (100nm)].

[0258] The performance data of the device embodiment are shown in Table 2. The current, voltage, brightness, luminescence spectrum and other characteristics of the device are tested synchronously using a Photo Research PR 655 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system. The performance test of the device is carried out at room temperature and ambient atmosphere. The external quantum efficiency (EQE) of the device is calculated by combining the current density, brightness and electroluminescence spectrum with the visibility function under the condition of Lambertian distribution of luminescence (the same below). The device life (T50, hours) in Table 2 refers to the device with an initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0259] Comparative device examples D1-n (n=1-26)

[0260] In the comparative device examples 1-n (n=1-26), the organic electroluminescent devices (structures such as Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-1 is used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the comparative device example) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect example is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 99 wt% H1-1 + 1 wt% Rm (30 nm) / TRZ-83 (10 nm) / TRZ-85 (30 nm) LiF (1 nm) / Al (100 nm)].

[0261] The performance data of the comparative device embodiment are shown in Table D2. The device life (T50, hours) in Table D2 refers to the device with an initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0262] Table 2

[0263]

[0264]

[0265]

[0266] Table D2

[0267]

[0268]

[0269] Device Example 2-n (n=1-73)

[0270] In the device example 2-n (n=1-73), the organic electroluminescent device (structure as Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-1 + TRZ-83 are used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15wt% HIM+85wt% HTL-1 (100nm) / HTL-2 (10nm) / 70wt% H1-1+29wt% TRZ-83+1wt% BN-m (30nm) / TRZ-83 (10nm) / TRZ-85 (30nm)LiF (1nm) / Al (100nm)].

[0271] The performance data of the device embodiment are shown in Table 3. The device life (T50, hours) in Table 3 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0272] Comparative device example D2-n (n=1-26)

[0273] In the comparative device example 2-n (n=1-26), the organic electroluminescent device (structure as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-1 + TRZ-83 are used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15wt% HIM+85wt% HTL-1 (100nm) / HTL-2 (10nm) / 70wt% H1-1+29wt% TRZ-83+1wt% Rm (30nm) / TRZ-83 (10nm) / TRZ-85 (30nm)LiF (1nm) / Al (100nm)].

[0274] The performance data of the comparative device embodiment are shown in Table D3. The device life (T50, hours) in Table D3 refers to the device initial brightness of 1000 cd / m 2When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0275] Table 3

[0276]

[0277]

[0278]

[0279] Table D3

[0280]

[0281] Device Example 3-n (n=1-73)

[0282] In the device example 3-n (n=1-73), the organic electroluminescent device (structure as Figure 1 As shown), HTL-1 doped with HIM is used as the first

[0283] A hole transport layer is used, HTL-2 is used as the second hole transport layer, H1-227 + 2CN-37 are used as the host materials in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doping light-emitting material (doping concentration is 1 wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-227 + 29 wt% 2CN-37 + 1 wt% BN-m (30 nm) / TRZ-83 (10 nm) / TRZ-85 (30 nm) LiF (1 nm) / Al (100 nm)].

[0284] The performance data of the device embodiment are shown in Table 4. The device life (T50, hours) in Table 4 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0285] Comparative device example 3-n (n=1-26)

[0286] In the device examples 3-n (n=1-26), the organic electroluminescent device (structure as Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-227 + 2CN-37 are used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15wt% HIM+85wt% HTL-1 (100nm) / HTL-2 (10nm) / 70wt% H1-227+29wt% 2CN-37+1wt% Rm (30nm) / TRZ-83 (10nm) / TRZ-85 (30nm)LiF (1nm) / Al (100nm)].

[0287] The performance data of the device embodiment are shown in Table D4. The device life (T50, hours) in Table D4 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0288] Table 4

[0289]

[0290]

[0291]

[0292] Table D4

[0293]

[0294] Device Example 4-n (n=1-73)

[0295] In the device examples 1-n (n=1-73), the organic electroluminescent devices (structures such as Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-227 + IrPPy are used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-227 + 9 wt% IrPPy + 1 wt% BN-m (30 nm) / TRZ-83 (10 nm) / TRZ-85 (30 nm) LiF (1 nm) / Al (100 nm)].

[0296] The performance data of the device embodiment are shown in Table 5. The device life (T50, hours) in Table 5 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0297] Comparative device example 4-n (n=1-26)

[0298] In the device examples 1-n (n=1-26), the organic electroluminescent devices (structures such as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-227 + IrPPy are used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-83 is used as the second electron transport layer, TRZ-85 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-227 + 9 wt% IrPPy + 1 wt% Rm (30 nm) / TRZ-83 (10 nm) / TRZ-85 (30 nm) LiF (1 nm) / Al (100 nm)].

[0299] The performance data of the device embodiment are shown in Table D5. The device life (T50, hours) in Table D5 refers to the device initial brightness of 1000 cd / m 2When the brightness of the device drops to 50% of the initial brightness (i.e. the brightness of the device drops to 500cd / m 2 The time required for

[0300] Table 5

[0301]

[0302]

[0303] Table D5

[0304]

[0305] The applicant states that while the above-described embodiments illustrate the boron-nitrogen compounds and their applications, the present invention is not limited to these embodiments. This does not necessarily mean that the present invention must rely on these embodiments for implementation. Those skilled in the art will appreciate that any improvements to the present invention, equivalent substitutions for the raw materials used, additions of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that: The boron nitrogen compound has a structure shown in the following formula I or formula II: R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R a Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R a substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R a substituted diphenylamino groups; R a Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R b substituted diphenylamino groups; R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R c substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R c substituted diphenylamino groups; R c Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R d substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R d substituted diphenylamino groups; R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or replaced by one or more R e substituted C6-C14 aryl; R e Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 and R 18 Independent existence or R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 and R 18 At least one of them forms a ring with the connected aromatic ring; R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 Can exist independently or R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 At least one of them forms a ring with the connected aromatic ring; R 31 、R 32 、R 33 and R 34 independently selected from H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, one or more R f Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R f substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R f substituted diphenylamino groups; R f Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C18 aryl, g Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R g substituted diphenylamino groups; R g Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c substituted C6-C14 aryl, 5- to 18-membered heteroaryl; R 31 、R 32 、R 33 and R 34 Exist independently or R 31 、R 32 、R 33 and R 34 At least one of them forms a ring with the connected aromatic ring; R 10 and R 20 are independently H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, h Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R h substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R h substituted diphenylamino groups; R h Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, or 5- to 18-membered heteroaryl or diphenylamino; R i Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c substituted C6-C14 aryl, 5- to 18-membered heteroaryl; R is H, 6-C14 aryl, one or more R i Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R i substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R i substituted diphenylamino, and when R is H, R 10 Not for H; R i Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, 5- to 18-membered heteroaryl, or diphenylamino R x1 、R y1 、R x2 and R y2 independently H, D (deuterium), C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R m1 Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R m1 substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R m1 substituted diphenylamino groups; R m1 Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, m2 Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R m2 substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R m2 substituted diphenylamino groups; R m2 Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or 5- to 18-membered heteroaryl; R x1 and R y1 Independent existence or R x1 and R y1 form a ring with each other; R x2 and R y2 Independent existence or R x2 and R y2 form a ring with each other; The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl groups.

2. The boron nitrogen compound according to claim 1, characterized in that The R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 are independently H, D (deuterium), C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl, C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R a Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R b Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R c Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R d Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, carbazolyl, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 are independently H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexyloxy, Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl, The wavy lines represent the attachment sites of the groups; Preferably, the R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 are independently H, methyl, 2-methyl-phenyl, Phenyl, The wavy lines represent the attachment sites of the groups; Preferably, R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 and R 28 At least one of them forms any one of the following ring structures with the connected aromatic ring: The bond with * is the bond shared with the aromatic ring; Preferably, the R 31 、R 32 、R 33 and R 34 independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl; Preferably, the R 31 、R 32 、R 33 and R 34 independently selected from H or phenyl; Preferably, the R 31 、R 32 、R 33 and R 34 At least one of them forms any one of the following ring structures with the aromatic ring connected to it: The bond with * is the bond shared with the aromatic ring; Preferably, the R is selected from C6-C18 aryl or 5- to 24-membered heteroaryl; Preferably, R is selected from hydrogen, phenyl, Biphenyl, The wavy lines represent the attachment sites of the groups; Preferably, the R 10 and R 20 independently selected from H, deuterium, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl; Preferably, the R 10 and R 20 are independently selected from H, phenyl, pyridyl, phenyl substituted pyridyl, cyano substituted phenyl, The wavy lines represent the attachment sites of the groups; Preferably, the R 31 、R 32 、R 33 and R 34 Independently selected from H, methyl, ethyl, isopropyl, phenyl, biphenyl, carbazolyl, diphenylamino, The wavy lines represent the attachment sites of the groups; Preferably, the R 31 、R 32 、R 33 and R 348 At least one of them forms any one of the following ring structures with the connected aromatic ring: The bond with * is the bond shared with the aromatic ring; Preferably, R is selected from phenyl or biphenyl; Preferably, the R 10 and R 20 are independently selected from hydrogen, deuterium, phenyl or biphenyl.

3. The boron nitrogen compound according to claim 1 or 2, characterized in that The boron nitrogen compound is any one of the following compounds:

4. An organic electroluminescent composition, characterized in that It comprises the boron nitrogen compound according to any one of claims 1 to 3 and a host material as a doping material; Preferably, the host material is a material having electron transport capability and / or hole transport capability and a triplet excited state energy thereof being higher than or equal to the triplet excited state energy of the doped light-emitting material.

5. The organic electroluminescent composition according to claim 4, characterized in that The host material is a compound having a structure as shown in any one of formulas (H-1) to (H-10): wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N; where R 1H and R 2H Independently any of the following groups: wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N; where R aH and R bH are independently H, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or C1-C 20 Alkoxy-substituted C6-C 20 Aryl, * represents the attachment site of the group; W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 independently S or O; R 3H 、R 4H 、R 5H 、R 6H 、R 7H 、R 8H 、R 9H 、R 10H 、R 11H 、R 12H 、R 13H and R 14H are independently H, deuterium, C1-C6 alkyl or C6-C24 aryl; Preferably, the organic electroluminescent composition contains 0.3-30.0 wt% of the boron nitrogen compound according to any one of claims 1-3 as a dopant material, and the remaining 99.7-70.0 wt% of the components are a host material composed of 1-2 compounds having structures of formula (H-1) to formula (H-10); Preferably, the host material contains two compounds having structures of formula (H-1) to formula (H-10), and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains 0.3-30.0 wt% of the boron nitrogen compound according to any one of claims 1 to 3, and the remaining 99.7-70.0 wt% of the components are one or two compounds selected from compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains two compounds selected from compounds H1-1 to H1-254 as host materials, and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds according to any one of claims 1 to 3; the host material is composed of any one of the compounds represented by formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds having the structures represented by formulas H-1 to H-10; where R 1a 、R 1b 、R 2a 、R 2b 、R 3a and R 3b One or two of them are independently R Tz , the rest are the same or different and are independently hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 C6-C8 substituted aryl or C1-C8 alkoxy 18 Aryl; R Tz is any one of the substituent groups shown below: The asterisk represents the attachment site of the group; Preferably, the amount ratio between the compound represented by Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compound represented by H-1, H-2, H-3, H-4, H-5H-6, H-7, H-8, H9 or H-10 in the host material is 1:20 to 20:1; Preferably, the weight ratio of the compound represented by formulae TRZ-1 to TRZ-86 to the carbazole or carboline derivative represented by any one of formulae (H-1) to (H-10) in the host material is 1:20 to 20:1; Preferably, the weight ratio between the compounds represented by formulas TRZ-1 to TRZ-86 and the compounds H1-1 to H1-254 in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the compounds of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by formulas H-1 to H-10; in the host material, the weight ratio between the Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II; the host material is composed of any one of the 1,3,5-triazine derivatives represented by Formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by Formulas H1-1 to H1-254; in the host material, the weight ratio of the 1,3,5-triazine derivative to the carbazole or carboline derivative is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288; the host material is composed of any one of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254; in the host material, the weight ratio of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A to the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288; the host material is composed of any one of the 1,3,5-triazine derivatives represented by formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254; in the host material, the weight ratio between the 1,3,5-triazine derivative represented by formulas TRZ-1 to TRZ-86 and the carbazole or carboline derivative represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, in the organic electroluminescent composition, the host material is composed of any one of the compounds having the structures represented by formulae H-1 to H-10 and any one of the compounds represented by formulae Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6; Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur); R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl; R si (i=7-39) are independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl; Preferably, R s1 、R s2 、R s3 、R s4 、R s5 and R s6 Independently selected from any of the following 24 groups: Asterisks represent the attachment sites of the groups; Preferably, R si (i=7-39) are independently selected from any one of the following five groups: Asterisks represent the attachment sites of the groups; Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds according to any one of claims 1 to 3, and the host material is composed of any one of the compounds represented by formulae 2CN-1 to 2CN-60 and any one of the compounds represented by formulae H1-1 to H1-254; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the compounds of formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds represented by formulas H-1 to H-10; preferably, in the host material, the weight ratio between the compounds of Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and the compounds represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the dicyanobenzene derivatives represented by formulae 2CN-1 to 2CN-60 and any one of the carbazole derivatives represented by formulae H1-1 to H1-254; preferably, in the host material, the weight ratio of the dicyanobenzene derivative to the carbazole derivative is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288, and the host material is composed of any one of the compounds represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds represented by formulas H1-1 to H1-254; preferably, in the host material, the weight ratio between the compound represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and the compound represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-288, and the host material is composed of any one of the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and any one of the compounds represented by formulas H1-1 to H1-254; preferably, in the host material, the weight ratio between the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and the carbazole derivatives represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3, and the main material is composed of any one of the compounds shown in Formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir or Pt as shown in Formulas Ir-1, Ir-2 and Pt-; preferably, in the main material, the weight ratio between the compounds shown in Formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is 1:20 to 20:

1. R ri are independently hydrogen, deuterium, C1-C18 alkyl, or C6-C18 aryl, wherein i is an integer from 1 to 22, and wherein the dashed line represents that two of the four bonds included are double bonds; R ri Any of the groups can form a ring with the aromatic ring or aromatic heterocycle to which it is connected; Preferably, the phosphorescent compound containing metal Ir is any one of the following compounds: Preferably, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formulas BN-1 to BN-288, and the main material is composed of any one of the carbazole or carbidine derivatives shown in formulas H1-1 to H1-254 and the phosphorescent compounds containing metal Ir shown in formulas Ir-1 and Ir-2. Preferably, in the main material, the weight ratio between the carbazole or carbidine derivatives shown in formulas H1-1 to H1-254 and the phosphorescent compounds containing metal Ir is 1:20 to 20:

1.

6. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the boron nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5.

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the boron nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, and an optional electron injection layer, wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer comprises the boron nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5.

9. The organic electroluminescent device according to claim 7 or 8, characterized in that: The material of the light-emitting layer in the organic electroluminescent device comprises the boron nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5; Preferably, the organic electroluminescent device further comprises an optional hole blocking layer, an optional electron blocking layer and an optional capping layer.

10. Use of the organic electroluminescent device according to any one of claims 7 to 9 in an organic electroluminescent display or an organic electroluminescent lighting source.

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