Boron-nitrogen compound with helical structure and application thereof

Abstract

The invention provides a boron-nitrogen compound with a helical structure and an application thereof, the boron-nitrogen compound has a structure shown as a formula I. According to the boron-nitrogen compound provided by the invention, through extension conjugation and introduction of nitrogen atoms, not only is fine adjustment of a spectrum realized, but also the luminous efficiency is further improved. 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 and belongs to green-red light region emission, the half-peak width is less than 50nm, and the highest electroluminescent external quantum efficiency of the device is as high as 30% or above.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and relates to a boron nitride compound with a helical structure and its application. 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 solar cells (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 at home and abroad. OLED displays have the characteristics of self-luminescence, wide viewing angles, short response times, high luminous efficiency, wide color gamuts, low operating voltages, thin panels, the ability to fabricate large-sized flexible panels, and low costs, and are hailed as the star flat panel display products of the 21st century.

[0003] Regarding the history of organic electroluminescence, it can be traced back to the report by Bernanose et al. in 1953 (Holst G A, Kster T, Voges E, et al. FLOX—an oxygen-flux-measuring system using a phase-modulation method to evaluate the oxygen-dependent fluorescence lifetime, ScienceDirect. Sensors and Actuators B: Chemical, 1995, 29, 213.). Approximately 10 years later, in 1963, Pope et al. at New York University applied a voltage to a crystal of anthracene 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, C.W. Tang et al. from Eastman Kodak Company in the United States used ultra-thin film technology, with an aromatic amine with good hole transport effect 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 to fabricate a light-emitting device. This device achieved a green light emission with a brightness as high as 1000 cd / m2 under a driving voltage of 10 V, and the efficiency of the device was 1.5 lm / W (C.W. Tang and S.A. Van Slyke, Organic electroluminescent diodes, Appl. Phys. Lett., 1987, 51, 913). This breakthrough progress enabled the research on organic electroluminescence to be rapidly and deeply carried out worldwide. In 1990, Burroughes et al. at the University of Cambridge proposed the first light-emitting diode based on a polymer (PPV). It was shown that in a single-layer device, PPV could be used as a highly fluorescent emission material with a relatively high luminous efficiency (Burroughes J.H. et al., Light-emitting diodes based on conjugated polymers, Nature, 1990, 347, 539.).In 1998, Baldo, Forrest et al. from Princeton University reported the first phosphorescent device based on electroluminescence, which could in principle have an internal quantum yield of 100% (M.A. Baldo, D.F. O'Brien et al., 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, for deep blue phosphorescent materials, there are still problems such as chemical instability and large efficiency roll-off of the device at high current density. Therefore, it is extremely important to develop an OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission.

[0004] In 2012, the research group of Adachi from Kyushu University reported a highly efficient all-fluorescent OLED device based on the mechanism of thermally activated delayed fluorescence (TADF) (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 energy level difference between S1 and T1 of the molecule is small enough, triplet excitons can absorb thermal energy, return to the singlet state through the RISC process, and then emit fluorescence. The internal quantum efficiency (IQE) of its device can theoretically reach 100%, and the external quantum efficiency (EQE) is even as high as 30%, comparable to the level of phosphorescent devices. As the next-generation luminescent material, the research on TADF materials is in full swing.

[0005] TADF molecules are mainly doped as guest materials in wide-bandgap host materials to achieve high-efficiency 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). Different from the emission of traditional fluorescent molecules from the local (LE) state, TADF emission mainly originates from the transition of the ICT state. Therefore, it is easily affected by the vibrational and rotational motions between the donor and acceptor, resulting in a relatively wide spectrum and a long excited-state lifetime of delayed fluorescence. As a result, the stability of electroluminescent devices based on TADF luminescent materials is poor. Although pure organic TADF luminescent materials get rid of the dependence on precious metals and have the advantage of low cost, due to their poor color purity of the emission spectrum and defects in stability, these are the main problems faced by organic TADF luminescent materials. Summary of the Invention

[0006] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a boron-nitrogen compound with a helical structure and its application.

[0007] To achieve the purpose of this invention, the following technical solutions are adopted in the present invention:

[0008] On the one hand, the present invention provides a boron-nitrogen compound, and the boron-nitrogen compound has the structure shown in the following formula I:

[0009]

[0010] R 1 、R 2 、R 3and R 4 are each independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted with one or more R a , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R a , diphenylamino, or diphenylamino substituted with one or more R a ;

[0011] R a is independently, each time it appears, deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R b , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R b , diphenylamino, or diphenylamino substituted with one or more R b ;

[0012] R b is independently, each time it appears, deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R c , diphenylamino, or diphenylamino substituted with one or more R c ;

[0013] R c is independently, each time it appears, deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R d , diphenylamino, or diphenylamino substituted with one or more R d ;

[0014] R d is independently, each time it appears, deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 aryl substituted with one or more R e ;

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

[0016] R 1 , R 2 , R 3 and R 4 may exist independently or R 1 , R 2 , R 3 and R 4 at least one of them forms a ring with the adjacent aromatic ring;

[0017] R 11 , R 12 , R 13 and R 14 are independently selected from H, deuterium, fluorine, CN, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C6-C18 aryl group, a C6-C18 aryl group substituted with one or more R f , a 5- to 18-membered heteroaryl group, a 5- to 18-membered heteroaryl group substituted with one or more R f , a diphenylamino group, or a diphenylamino group substituted with one or more R f ;

[0018] R f Each occurrence is independently deuterium, fluorine, CN, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 cycloalkyl group, a C6-C14 aryl group, a C6-C14 aryl group substituted with one or more R g , a 5- to 18-membered heteroaryl group, a 5- to 18-membered heteroaryl group substituted with one or more R b , a diphenylamino group, or a diphenylamino group substituted with one or more R g ;

[0019] R g Each occurrence is independently deuterium, fluorine, CN, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C10 cycloalkyl group, a C6-C14 aryl group, a C6-C14 aryl group substituted with one or more R c , a 5- to 18-membered heteroaryl group;

[0020] R 11 , R 12 , R 13 and R 14 exist independently of each other or at least one of R 11 , R 12 , R 13 and R 14 forms a ring with the adjacent aromatic ring;

[0021] E is wherein the wavy line represents the attachment site of the group;

[0022] X is S or O;

[0023] R 21 , R 22 , R 23 , R 24 , R 25 and R 26 are independently H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted with one or more R h , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R h , diphenylamino, or diphenylamino substituted with one or more R h ;

[0024] R h is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R i , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R i , diphenylamino, or diphenylamino substituted with one or more R g ;

[0025] R i is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c , 5- to 18-membered heteroaryl;

[0026] R 21 , R 22 , R 23 and R 24 exist independently or at least one of R 21 , R 22 , R 23 and R 24 forms a ring with the attached aromatic ring;

[0027] R 25 and R 26 exist independently or at least one of R 25 and R 26 forms a ring with the attached aromatic ring.

[0028] The alkyl group, alkoxy group, cycloalkyl group, aryl group, and heteroaryl group are optionally substituted with one or more substituents selected from the following: halogen, -CN, C1-C12 alkyl group, C1-C12 alkoxy group, C1-C12 haloalkyl group, C3-C10 cycloalkyl group, C6-C14 aryl group, and 5- to 18-membered heteroaryl group.

[0029] In some embodiments of the present invention, the R 1 , R 2 , R 3 and R 4 are independently H, D (deuterium), C1-C12 alkyl group, C1-C 12 alkoxy group, C3-C 10 cycloalkyl group, phenyl group, aryl group substituted with at least one C1-C 12 alkyl group, aryl group substituted with at least one C1-C 12 alkoxy group, phenyl-C1-C 12 alkyl group, diphenylamino group, diphenylamino group substituted with at least one C1-C 12 alkyl group, carbazolyl group, carbazolyl group substituted with at least one C1-C 12 alkyl group;

[0030] Preferably, each occurrence of the R a is independently deuterium, fluorine, C1-C 12 alkyl group, C1-C 12 alkoxy group, C3-C 10 cycloalkyl group, phenyl group substituted with at least one C1-C 12 alkyl group, phenyl group substituted with at least one C1-C 12 alkoxy group, phenyl-C1-C 12 alkyl group, diphenylamino group, diphenylamino group substituted with at least one C1-C 12 alkyl group, carbazolyl group, carbazolyl group substituted with at least one C1-C 12 alkyl group;

[0031] Preferably, each occurrence of the R b is independently deuterium, fluorine, C1-C 12 alkyl group, C1-C 12 alkoxy group, C3-C 10 cycloalkyl group, phenyl group substituted with at least one C1-C 12 alkyl group, phenyl group substituted with at least one C1-C 12 alkoxy group, phenyl-C1-C 12 alkyl group, diphenylamino group, diphenylamino group substituted with at least one C1-C 12 alkyl group, carbazolyl group, carbazolyl group substituted with at least one C1-C 12 alkyl group;

[0032] Preferably, the R c is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted with at least one C1-C 12 alkyl, phenyl substituted with at least one C1-C 12 alkoxy, phenyl-C1-C 12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C 12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C 12 alkyl;

[0033] Preferably, the R d is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted with at least one C1-C 12 alkyl, phenyl substituted with at least one C1-C 12 alkoxy, carbazolyl, carbazolyl substituted with at least one C1-C 12 alkyl;

[0034] Preferably, the R 1 , R 2 , R 3 and R 4 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,

[0035] or, where the wavy line represents the attachment site of the group;

[0036] Preferably, the R 1 , R 2 , R 3 and R 4 are independently H, methyl, phenyl, 2-methyl-phenyl,

[0037] Wherein the wavy line represents the connection site of the group.

[0038] Preferably, the R 1 , R 2 , R 3 and R 4 are the same and are selected from any one of H, methyl, phenyl, 2-methyl-phenyl, ;

[0039] Wherein R j is H, methyl, isopropyl, tert-butyl or

[0040] Preferably, at least one of R 1 , R 2 , R 3 and R 4 forms any one of the following ring structures with the connected aromatic ring:

[0041] Wherein the bond where the * sign is located is the bond shared with the aromatic ring;

[0042] Preferably, the R 11 , R 12 , R 13 and R 14 are independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl or 5- to 24-membered heteroaryl.

[0043] Preferably, the R 21 , R 22 , R 23 , R 24 , R 25 and R 26 are independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl or 5- to 24-membered heteroaryl.

[0044] In some embodiments of the present invention, the boron nitride compound is any one of the following compounds:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050] In the present invention, the boron nitride compound has a helical chiral structure. For the sake of clearly showing without overlapping aromatic rings, some bonds in the specific compound structures given above are intentionally elongated. However, in fact, the compound has a helical chiral structure as shown below:

[0051]

[0052] On the other hand, the present invention provides an organic electroluminescent material, and the organic electroluminescent material includes the boron nitride compound as described above.

[0053] On the other hand, the present invention provides an organic electroluminescent device, and the organic electroluminescent device includes an anode and a cathode, and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer includes the boron nitride compound as described above.

[0054] 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, and 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 includes the boron nitride compound as described above.

[0055] In the present invention, the boron nitride compound having the structures shown in Formula I and Formula II can be used as a functional material in 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 of an organic electroluminescent device.

[0056] 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, etc.

[0057] In one embodiment, the organic electroluminescent device has a structure as shown in Figure 1 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.

[0058] In a certain embodiment, the boron nitride compound having the structure shown in Formula I is used to prepare the light-emitting layer in an organic electroluminescent device.

[0059] In a certain embodiment, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer formed in sequence on the substrate; in the organic light-emitting functional layer, it includes a light-emitting layer containing the boron nitride compound as described above, and may further include any one or a combination of at least two 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.

[0060] On the other hand, the present invention provides an organic electroluminescent composition comprising the above-described boron nitride compound as a doping material and a host material;

[0061] Preferably, the host material is a material having electron transporting ability and / or hole transporting ability and whose triplet excited state energy is equal to or higher than the triplet excited state energy of the doping material.

[0062] In one embodiment of the present invention, the host material is a carbazole derivative and / or a carboline derivative having a structure represented by any one of formulas (H-1) to (H-10):

[0063]

[0064]

[0065] wherein X1, Y1, and Z1 are CH or N, and at most one of X1, Y1, and Z1 is N;

[0066] wherein R 1H and R 2H are independently any one of the following groups:

[0067]

[0068] wherein X1, Y1, and Z1 are CH or N, and at most one of X1, Y1, and Z1 is N;

[0069] wherein 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, and the * represents the connection site of the group;

[0070] W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 are independently S or O;

[0071] 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.

[0072] In one embodiment of the present invention, in the organic electroluminescent composition, preferably 0.3-30.0 wt% (such as 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 nitride compound as described above is contained as a doping material, and the remaining 99.7-70.0 wt% (such as 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 components are host materials composed of one or two compounds having the structures of formula (H-1) to formula (H-10);

[0073] In one embodiment of the present invention, the host material contains two compounds having the structures of formula (H-1) to formula (H-10), and the weight ratio of the two compounds is 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0074] Preferably, the host material in the organic electroluminescent composition is one or two of the compounds H1-1 to H1-254;

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] In one embodiment of the present invention, in the organic electroluminescent composition, 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 nitride compound having the structure shown in Formula I as described above is contained, 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 components are one or two compounds among Compounds H1-1 to H1-254.

[0086] In a preferred embodiment of the present invention, the organic electroluminescent composition contains two compounds among Compounds H1-1 to H1-254 as host materials, and the weight ratio of these two compounds is 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0087] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the boron nitride compounds having the structure shown in Formula I (content: 0.3 wt%-30.0 wt%); the host material (content: 99.7 wt%-70.0 wt%) 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.

[0088] In a preferred embodiment, the quantitative ratio between the compound shown in Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compound shown in H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H9 or H-10 in the host material is 1:20 to 20:1, such as 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.

[0089]

[0090] wherein R 1a 、R 1b 、R 2a 、R 2b 、R 3a and R 3b one or two of them are independently R Tz , and the rest are the same or different and independently are hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, C6-C 18 aryl, C1-C8 alkyl-substituted C6-C 18 aryl or C1-C8 alkoxy-substituted C6-C 18 aryl; R Tz is any one of the substituted groups shown by the following formulae:

[0091]

[0092]

[0093] wherein the asterisk represents the connection site of the group.

[0094] In a preferred embodiment, the weight ratio between the compounds shown by the formulae TRZ-1 to TRZ-82 and the carbazole or carboline derivatives shown by the formulae (H-1) to (H-10) in the host material is 1:20 to 20:1, such as 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.

[0095] 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 (with a content of 0.3 wt% - 30.0 wt%); the host material (with a content of 99.7 wt% - 70.0 wt%) is composed of any one of the compounds such as those represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by Formula H-1 to H-10. For example, in the host material, the weight 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-5, H-6, H-7, H-8, H-9 or H-10 is from 1:20 to 20:1, such as 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.

[0096] 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 (with a content of 0.3 wt% - 30.0 wt%); the host material (with a content of 99.7 wt% - 70.0 wt%) is composed of any one of the 1,3,5-triazine derivatives represented by Formula TRZ-1 to TRZ-82 and any one of the carbazole or carbazoline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carbazoline derivative represented by Formula H1-1 to H1-254 is from 1:20 to 20:1, such as 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.

[0097] 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 BN-1 to BN-105 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of the compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A and any one of the carbazole or carboline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carboline derivatives represented by Formula H1-1 to H1-254 is 1:20 to 20:1, such as 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.

[0098] 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 BN-1 to BN-105 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of the 1,3,5-triazine derivatives represented by Formula TRZ-1 to TRZ-82 and any one of the carbazole or carboline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the 1,3,5-triazine derivatives represented by Formula TRZ-1 to TRZ-82 and the carbazole or carboline derivatives represented by Formula H1-1 to H1-254 is 1:20 to 20:1, such as 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.

[0099]

[0100]

[0101]

[0102]

[0103] In the present invention, in the organic electroluminescent composition, the main material is composed of any one of the compounds having the structures shown in formulas H-1 to H-10 and any one of the compounds shown in formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6.

[0104]

[0105]

[0106] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur);

[0107] R 1s , R 2s , R 3s , R 4s , R 5s and R 6s 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 1s , R 2s , R 3s , R 4s , R 5s and R 6s Independently selected from any of the following 24 groups:

[0108] The asterisk represents the attachment site of the group.

[0109] Preferably, R si (i=7-39) is independently selected from any one of the following five groups:

[0110]

[0111] Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds having the structure shown in formula I as described above, and the main material is composed of any one of the compounds shown in formulas 2CN-1 to 2CN-60 and any one of the compounds shown in formulas H1-1 to H1-254;

[0112]

[0113]

[0114]

[0115] In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition may be a carbazole derivative and / or a carboline derivative represented by formula (H-1) to formula (H-10). In a preferred embodiment, in the organic electroluminescent composition, any one of the compounds represented by formula I is contained in an amount of 0.3-30.0 wt%, and the remaining 99.7-70.0 wt% of the components are a host composed of 1-2 compounds having the structures of formula (H-1) to formula (H-10). For example, when the host 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, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0116] In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the host material in the composition is 1-2 of compounds H1-1 to H1-254. In a preferred embodiment, in the organic electroluminescent composition, any one of the compounds represented by formula I is contained in an amount of 0.3-30.0 wt%, and the remaining 99.7-70.0 wt% of the components are 1-2 of compounds H1-1 to H1-254. For example, when the composition contains 2 compounds of H1-1 to H1-254, the weight ratio of the two compounds is 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0117] In a certain 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 (content: 0.3 wt%-30.0 wt%); the host material (content: 99.7 wt%-70.0 wt%) is composed of any one of compounds such as Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by formula H-1 to H-10. For example, in the host material, the weight ratio between the compound of 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-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1, such as 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 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 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of 1,3,5-triazine derivatives represented by Formulae TRZ-1 to TRZ-82 and any one of carbazole or carboline derivatives represented by Formulae H1-1 to H1-254. For example, in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:20 to 20:1, such as 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] 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 Formulae BN-1 to BN-105 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of the compounds represented by Formulae Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of carbazole or carboline derivatives represented by Formulae H1-1 to H1-254. For example, in the host material, the weight ratio between the compounds represented by Formulae Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carboline derivatives represented by Formulae H1-1 to H1-254 is 1:20 to 20:1, such as 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.

[0120] In an 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 (content is 0.3 wt%-30.0 wt%); the host material (content is 99.7 wt%-70.0 wt%) is composed of any one of the compounds such as 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 Formula H-1 to H-10. For example, in the host material, the weight ratio between the compound of Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 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, such as 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.

[0121] In an 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 (content is 0.3 wt%-30.0 wt%); the host material (content is 99.7 wt%-70.0 wt%) is composed of any one of the dicyanobenzene derivatives represented by Formula 2CN-1 to 2CN-60 and any one of the carbazole or carboline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the dicyanobenzene derivative and the carbazole or carboline derivative is 1:20 to 20:1, such as 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.

[0122] 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-105 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) 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 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 carbazole or carboline derivative represented by formulas H1-1 to H1-254 is 1:20 to 20:1.

[0123] 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-105 (content: 0.3 wt% - 30.0 wt%), and the host material (content: 99.7 wt% - 70.0 wt%) 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 derivative represented by formulas 2CN-1 to 2CN-60 and the carbazole or carboline derivative represented by formulas H1-1 to H1-254 is 1:20 to 20:1, such as 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.

[0124] 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 (content: 0.3 wt% - 30.0 wt%), and the host material (content: 99.7 wt% - 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 between the carbazole or carboline derivative represented by Formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is from 1:20 to 20:1, such as 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.

[0125]

[0126] R ri independently represents hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, where i is an integer from 1 to 22, and the dotted line represents that two of the four included bonds are double bonds at intervals;

[0127] R ri any one of the groups can form a ring with the aromatic ring or aromatic heterocycle to which it is attached;

[0128] Preferably, the phosphorescent compound containing metal Ir is any one of the following compounds:

[0129]

[0130] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the compounds represented by Formulas BN-1 to BN-105 (content: 0.3 wt% - 30.0 wt%), and the host material (content: 99.7 wt% - 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 between the carbazole or carboline derivative represented by Formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is from 1:20 to 20:1.

[0131] On the other hand, the present invention provides an organic electroluminescent material, and the organic electroluminescent material includes the organic electroluminescent composition as described above.

[0132] On the other hand, the present invention provides an organic electroluminescent device, which comprises an anode and a cathode, and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer contains the organic electroluminescent composition as described above.

[0133] 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.

[0134] In the present invention, the organic electroluminescent composition can be used as a functional material in 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 of the organic electroluminescent device.

[0135] In one embodiment of the present invention, the material of the light-emitting layer in the organic electroluminescent device contains the organic electroluminescent composition as described above.

[0136] 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 the energy transfer from the host material to any one of the compounds shown in Formula I or the carrier capture of the light-emitting material itself.

[0137] In one embodiment of the present invention, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer formed in sequence on the substrate; in the organic light-emitting functional layer, it includes a light-emitting layer containing the organic electroluminescent composition as described above, and may further include any one or at least two combinations 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.

[0138] On the other hand, the present invention provides an application of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0139] Term Explanation

[0140] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present invention belongs.

[0141] As used herein, the term "comprising" or "including" can be open-ended, semi-closed, and closed. In other words, the term also includes "consisting essentially of...", or "consisting of...".

[0142] Group Definition

[0143] In this specification, groups and their substituents can be selected by those skilled in the art to provide stable structural moieties and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes the chemically equivalent substituent obtained when the structural formula is written from right to left.

[0144] The section headings used in this specification are for the purpose of organizing the article only and should not be construed as limiting the subject matter described. All documents or portions of documents cited in this invention, including but not limited to patents, patent applications, articles, books, manuals of operations, and theses, are incorporated herein by reference in their entirety.

[0145] Unless otherwise specified, all technical and scientific terms used herein have the standard meanings in the field to which the claimed subject matter pertains. If there are multiple definitions for a term, the definition herein shall prevail.

[0146] It should be understood that the singular forms used in this invention, such as "a", include plural referents unless otherwise specified. In addition, the term "comprising" is an open-ended limitation and not a closed one, that is, it includes what is specified in this invention but does not exclude other aspects.

[0147] Unless otherwise indicated, the present invention employs the conventional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.

[0148] Unless otherwise specified, the present invention employs the standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, organic synthetic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and the performance detection of light-emitting devices.

[0149] The compounds of the present invention may contain non-natural proportions of atomic isotopes on one or more atoms constituting the compound. For example, the compound can be labeled with a radioactive isotope such as deuterium (2H). All isotopic compositions of the compounds of the present invention, whether radioactive or not, are included within the scope of the present invention.

[0150] In the present invention, unless otherwise specified, the number of "substitutions" can be one or more; when there are multiple ones, it means more than two, for example, it can be 2, 3, or 4. And when the number of "substitutions" is multiple, the "substitutions" can be the same or different. In the present invention, the position of "substitution", if not specifically stated, can be arbitrary.

[0151] In the present invention, as a group or as part of other groups (such as in groups like halogen-substituted alkyl), the term "alkyl" means a saturated aliphatic hydrocarbon group including branched and straight-chain ones with the specified number of carbon atoms. For example, C1-C 20Alkyl includes straight-chain or branched-chain alkyl groups having 1 to 20 carbon atoms. As defined in "C1-C6 alkyl", it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight-chain or branched-chain structure. For example, in the present invention, the C1-C6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; among them, 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); hexyl is a C6 alkyl group (including isomers, such as n-hexyl or isohexyl).

[0152] As used herein, the term "alkoxy" refers to an alkyl group as defined above that is connected via an oxygen bond (-O-).

[0153] In the present invention, as a group or part of other groups, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group (ring atoms are only carbon atoms) having n to m ring carbon atoms, which has at least one carbon ring with a conjugated π-electron system. Examples of the above aryl units include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthracenyl. In one embodiment, the aryl is preferably a C6-14 aryl, such as phenyl and naphthyl, and more preferably phenyl.

[0154] In the present invention, as a group or as part of other groups, the term "n-m membered heteroaryl" refers to an aromatic group having one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur in the ring atoms, the ring atoms being from n to m in number, and the heteroaryl being a monocyclic, bicyclic, tricyclic, or tetracyclic system, wherein at least one ring is an aromatic ring. Heteroaryls within this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridyl, imidazothiazolyl, imidazoxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridyl, thiophenopyridyl, furanopyridyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thiophenofuryl. In one embodiment, as preferred examples of "5-18 membered heteroaryl", furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridyl, pyrimidinyl, and carbazolyl can be cited, and more preferably carbazolyl.

[0155] As used herein, the term Cn-Cm cycloalkyl refers to a monocyclic or polycyclic alkyl 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, C3-C10 cycloalkyl is preferably adamantyl or cyclohexyl.

[0156] In the present invention, the defined carbon number range of the groups means including any integer number of carbon atoms within the defined range, e.g., C1-C 20 means that the number of carbon atoms of 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, C3-C 10 means that the number of carbon atoms of the group can be 3, 4, 5, 6, 7, 8, 9, or 10, and the defined carbon number ranges of other groups can be analogized.

[0157] On the basis of not violating the common knowledge in the art, the above preferred conditions can be arbitrarily combined to obtain various preferred examples of the present invention.

[0158] The reagents and raw materials used in the present invention are all commercially available.

[0159] Compared with the prior art, the present invention has the following beneficial effects:

[0160] By expanding the conjugation and introducing nitrogen atoms, the boron nitride compound of the present invention not only realizes the fine adjustment of the spectrum but also further improves the luminescence efficiency. The boron nitride compound of the present invention has a narrow spectrum and is used as a narrow-spectrum luminescent material for preparing the light-emitting layer of an organic electroluminescent device. The organic electroluminescent device prepared therefrom realizes narrow-spectrum TADF emission, belonging to the green-light to red-light region emission, with a full width at half maximum of less than 50 nm, and enables the maximum external quantum efficiency of the electroluminescence of the device to be as high as more than 30%. Brief Description of the Drawings

[0161] Figure 1 It is a schematic structural diagram of a vacuum evaporation type organic electroluminescent device provided by the present invention. Among them, 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.

[0162] Figure 2 It is the electroluminescence spectrum of the device using compound BN-3.

[0163] Figure 3 It is the electroluminescence spectrum of the device using compound BN-32.

[0164] Figure 4 It is the electroluminescence spectrum of the device using compound BN-51.

[0165] Figure 5 It is the electroluminescence spectrum of the device using compound BN-70.

[0166] Figure 6 It is the electroluminescence spectrum of the device using compound BN-89. Detailed Embodiments

[0167] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0168] In the embodiments of the present invention, the raw materials used for synthesizing the shown compounds are as follows:

[0169] The specific initial general raw materials used include the following molecules:

[0170]

[0171]

[0172] The specific raw material 2 used includes the following molecules:

[0173]

[0174] Synthesis route and specific operations:

[0175] Synthesis of the first type of compounds:

[0176] When the two carbazole derivative ligands coordinated with B are the same (BN-1 to BN-15):

[0177]

[0178] General synthetic reaction process route:

[0179] First, using carbazole-based raw material Ai as the substrate, synthesize intermediate BN-Ai (i = 1 - 17, considering steric hindrance problems, i ≠ 11, 12) by the method reported in the previous patent. Then, using BN-Ai (i = 1 - 17, i ≠ 11, 12) as the substrate, obtain intermediate BN-Ai-Bpin through borylation reaction by the method reported in the previous patent. Finally, obtain precursor BN-M-n through a simple Suzuki reaction and coupling with brominated heterocyclic compounds, and then obtain the final product BN-n (n = 1 - 15) through oxidative cyclization.

[0180] In the first step, add 50.0 mmol of raw material Ai (i = 1 - 17, i ≠ 11, 12), 4.73 g of raw material 1-bromo-2,6-difluorobenzene (24.5 mmol), and 21.2 g of cesium carbonate (65.0 mmol) to 150 mL of anhydrous DMF (N,N-dimethylformamide). The reaction system is stirred at 160 °C for 18 hours, then cooled to room temperature and poured into ice water (2 L). Filter out the white solid, dry it in vacuo, and then further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate Br-Ai (i = 1 - 17, i ≠ 11, 12).

[0181] Step 2: Under the protection of nitrogen atmosphere, 19.4 mL of a n-hexane solution of tert-butyllithium (25.2 mmol) was slowly added to 100 mL of a tert-butylbenzene solution containing 12.6 mmol of intermediate Br-Ai (-30 °C). The temperature was slowly raised to 60 °C, and after stirring for 2 hours, n-hexane was removed under vacuum. Then, it was cooled to -30 °C, 2.38 mL of boron tribromide (25.2 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then, 4.13 mL of N,N-diisopropylethylamine (25.2 mmol) was added at 0 °C, and then the reaction mixture was heated to 130 °C and stirred for another 5 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 under vacuum and purified by column chromatography using a mixture of dichloromethane / petroleum ether as the eluent to obtain the target intermediate BN-Ai (i = 1 - 17, i ≠ 11, 12).

[0182] Step 3: At room temperature, intermediate BN-Ai (2.6 mmol) and 680 mg of bis(pinacolato)diboron (5.2 mmol) were added to tetrahydrofuran (40 mL). The mixture was bubbled with nitrogen for 10 minutes, and 13.96 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.052 mmol) and 17.24 mg of methoxy(cyclooctadiene)iridium(III) dimer (0.026 mmol) were added under high-flow nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain intermediate BN-Ai-Bpin (i = 1 - 17, i ≠ 11, 12).

[0183] Step 4: Boronic acid B1 of indolocarbazole (4.0 mmol), 2.26 g of o-bromoiodobenzene (8.0 mmol), 2.54 g of potassium phosphate (12.0 mmol), and water (3 mL) were added to tetrahydrofuran (50 mL). The mixture was bubbled with nitrogen for 10 minutes, and 115.6 mg of tetrakis(triphenylphosphine)palladium(0) (0.1 mmol) was added under high-flow nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and dried under vacuum, and then purified by column chromatography to obtain intermediate Br-B1.

[0184] Step 5: Add brominated indolocarbazole aryl compound Br-B1 (1.2 mmol), BN-Ai-Bpin (1.0 mmol), 636 mg of potassium phosphate (3 mmol), and water (50 μL) to dioxane (25 mL). Bubble the mixture with nitrogen for 10 minutes, and add 18.5 mg of Pd(dppf)Cl2 (0.025 mmol) under a high flow of nitrogen. Heat the mixture to 90 °C and stir for 12 hours. After the reaction system cools to room temperature, extract the reaction mixture with dichloromethane and water. Heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain the precursor BN-M-n (n = 1 - 15).

[0185] Step 6: Add BN-M-n (0.6 mmol) and 283.8 mg of PIFA ([bis(trifluoroacetoxy)iodo]benzene) (0.66 mmol) to 15 mL of anhydrous dichloromethane. Bubble the mixture with nitrogen for 10 minutes, slowly drop 192.5 mg of boron trifluoride ethyl etherate (1.32 mmol) at -40 °C. After maintaining the reaction mixture at -40 °C and stirring for 1.5 hours, add 3 mL of methanol to quench the residual boron trifluoride ethyl etherate in the reaction system. Extract the reaction mixture with dichloromethane and water. Heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain the final product BN-n (n = 1 - 15).

[0186] Relevant data of the obtained target compounds are shown in Table 1.

[0187] Taking compound BN-3 as an example to illustrate the specific details of the synthesis example experiment:

[0188] Step 1: Add 14 g of raw material A3 (50.0 mmol), 4.73 g of raw material 1-bromo-2,6-difluorobenzene (24.5 mmol), and 21.2 g of cesium carbonate (65.0 mmol) to 150 mL of anhydrous DMF (N,N-dimethylformamide). Stir the reaction system at 160 °C for 18 hours, then cool to room temperature and pour it into ice water (2 L). Filter out the white solid, dry it in vacuo, and then further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain the intermediate Br-3, a white solid, with a yield of 90%.

[0189] Step 2: Under the protection of nitrogen atmosphere, 19.4 mL of a n-hexane solution of tert-butyllithium (25.2 mmol) was slowly added to 80 mL of a tert-butylbenzene solution containing 8.81 g of intermediate Br-A3 (12.6 mmol) at -30 °C. The temperature was slowly raised to 60 °C, and after stirring for 2 hours, n-hexane was removed under vacuum. Then it was cooled to -30 °C, 2.4 mL of boron tribromide (25.2 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then 4.4 mL of N,N-diisopropylethylamine (25.2 mmol) was added at 0 °C, and then the reaction mixture was heated to 130 °C and stirred for another 5 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 under vacuum and purified by column chromatography with a mixture of dichloromethane / petroleum ether as the eluent to obtain the target intermediate BN-A3 as a yellow solid with a yield of 60%.

[0190] Step 3: At room temperature, 3.33 g of BN-A3 (5.2 mmol) and 1.36 g of bis(pinacolato)diboron (10.4 mmol) were added to tetrahydrofuran (70 mL). The mixture was bubbled with nitrogen for 10 minutes, and 27.92 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.104 mmol) and 34.48 mg of methoxy(cyclooctadiene)iridium(III) dimer (0.052 mmol) were added under high-flow nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain 3.2 g of BN-A3-Bpin as a yellow solid with a yield of 81%.

[0191] Step 4: 2.86 g of indolocarbazole boronic acid B1 (10.0 mmol), 5.09 g of o-bromoiodobenzene (18.0 mmol), 6.36 g of potassium phosphate (30.0 mmol) and water (8 mL) were added to tetrahydrofuran (100 mL). The mixture was bubbled with nitrogen for 10 minutes, and 231.2 mg of tetrakis(triphenylphosphine)palladium(0) (0.2 mmol) was added under high-flow nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and dried under vacuum, and then purified by column chromatography to obtain 2.5 g of Br-B1 as a white solid with a yield of 65%.

[0192] Step 5: Add 934.6 mg of Br-B1 (2.36 mmol), 1.5 g of BN-A3-Bpin (1.97 mmol), 1.25 g of potassium phosphate (5.91 mmol) and water (100 μL) to dioxane (45 mL). Bubble the mixture with nitrogen for 10 minutes and add 36.9 mg of Pd(dppf)Cl2 (0.05 mmol) under high-flow nitrogen. Heat the mixture to 90 °C and stir for 12 hours. After the reaction system cools to room temperature, extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain 1.15 g of precursor BN-M-3, a yellow solid, with a yield of 61%.

[0193] Step 6: Add 765 mg of BN-M-3 (0.8 mmol) and 378.4 mg of PIFA ([bis(trifluoroacetoxy)iodo]benzene) (0.88 mmol) to 20 mL of anhydrous dichloromethane. Bubble the mixture with nitrogen for 10 minutes, slowly drop 256.6 mg of boron trifluoride etherate (1.76 mmol) at -40 °C. After keeping the reaction mixture at -40 °C and stirring for 1.5 hours, add 3 mL of methanol to the reaction system to quench the residual boron trifluoride etherate. Extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain 430 mg of the final product BN-3, an orange solid, with a yield of 56%.

[0194] When the two carbazole derivative ligands coordinated to B are different (BN-16 to BN-29):

[0195]

[0196] General synthetic reaction process route:

[0197] First, use carbazole-based raw materials Ai and Ar as substrates in sequence to synthesize intermediate BN-Air by the method reported in the previous patent (considering steric hindrance problems, i = 1 - 17, i ≠ 11, 12, r = 7, 8, 11, 12, 18 - 27). Then, use BN-Air (i = 1 - 17, i ≠ 11, 12, r = 7, 8, 11, 12, 18 - 27) as the substrate to obtain intermediate BN-Air-Bpin through a boron esterification reaction by the method reported in the previous patent. Finally, obtain precursor BN-M-n through a simple Suzuki reaction and coupling with a brominated heterocyclic compound, and then obtain the final product BN-n (n = 16 - 29) through oxidative cyclization.

[0198] First step: Add 25.0 mmol of raw material Ai (i = 1 - 17, i ≠ 11, 12), 9.65 g of raw material 1-bromo-2,6-difluorobenzene (50.0 mmol), and 21.2 g of cesium carbonate (65.0 mmol) into 150 ml of anhydrous DMF (N,N-dimethylformamide). Stir the reaction system at 160 °C for 18 hours, then cool it to room temperature and pour it into ice water (2 L). Filter out the white solid, dry it in vacuo, and then further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate F-Br-Ai (i = 1 - 17, i ≠ 11, 12).

[0199] Second step: Add 25.0 mmol of raw material Ar (r = 7, 8, 11, 12, 18 - 27), 16.7 mmol of raw material F-Br-Ai, and 16.3 g of cesium carbonate (50.0 mmol) into 100 ml of anhydrous DMF (N,N-dimethylformamide). Stir the reaction system at 160 °C for 18 hours, then cool it to room temperature and pour it into ice water (2 L). Filter out the white solid, dry it in vacuo, and then further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate Br-Air (i = 1 - 17, i ≠ 11, 12, r = 7, 8, 11, 12, 18 - 27).

[0200] Third step: Under the protection of a nitrogen atmosphere, slowly add 19.4 mL of a n-hexane solution of tert-butyllithium (25.2 mmol) to 100 ml of a tert-butylbenzene solution containing 12.6 mmol of intermediate Br-Air (-30 °C). Slowly warm up to 60 °C, stir for 2 hours, then remove n-hexane in vacuo, and then cool to -30 °C. Add 2.38 ml of boron tribromide (25.2 mmol), and stir the reaction mixture at room temperature for 1 hour. Then add 4.13 ml of N,N-diisopropylethylamine (25.2 mmol) at 0 °C, and then raise the reaction mixture to 130 °C and continue to stir for 5 hours, and then cool to room temperature. Add 5 ml of methanol to the reaction mixture to quench the residual boron tribromide. Concentrate the reaction system in vacuo and purify it by column chromatography using a mixture of dichloromethane / petroleum ether as the eluent to obtain the target intermediate BN-Air (i = 1 - 17, i ≠ 11, 12, r = 7, 8, 11, 12, 18 - 27).

[0201] Step 4: At room temperature, add intermediate BN-Air (2.6 mmol) and 680 mg of bis(pinacolato)diboron (5.2 mmol) to tetrahydrofuran (40 mL). Bubble the mixture with nitrogen for 10 minutes, and then add 13.96 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.052 mmol) and 17.24 mg of methoxy(cyclooctadiene)iridium(III) dimer (0.026 mmol) under a high flow of nitrogen. After stirring for 10 minutes, heat the mixture to reflux and stir for 24 hours. After the reaction system cools to room temperature, directly concentrate it under reduced pressure and purify it by column chromatography to obtain intermediate BN-Air-Bpin (i = 1 - 17, i ≠ 11, 12, r = 7, 8, 11, 12, 18 - 27).

[0202] Step 5: Add the previously obtained intermediate Br-B1 (1.2 mmol), BN-Air-Bpin (1.0 mmol), 636 mg of potassium phosphate (3 mmol), and water (50 μL) to dioxane (25 mL). Bubble the mixture with nitrogen for 10 minutes, and then add 18.5 mg of Pd(dppf)Cl2 (0.025 mmol) under a high flow of nitrogen. Heat the mixture to 90 °C and stir for 12 hours. After the reaction system cools to room temperature, extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain precursor BN-M-n (n = 16 - 29).

[0203] Step 6: Add BN-M-n (0.6 mmol) and 283.8 mg of PIFA ([bis(trifluoroacetoxy)iodo]benzene) (0.66 mmol) to 15 mL of anhydrous dichloromethane. Bubble the mixture with nitrogen for 10 minutes, and slowly drop 192.5 mg of boron trifluoride diethyl etherate (1.32 mmol) at -40 °C. After maintaining the reaction mixture at -40 °C and stirring for 1.5 hours, add 3 mL of methanol to quench the residual boron trifluoride diethyl etherate in the reaction system. Extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain the final product BN-n (n = 16 - 29).

[0204] The relevant data of the obtained target compounds are shown in Table 1.

[0205] Take compound BN-16 as an example to illustrate the specific details of the synthesis example experiment:

[0206] Step 1: Add 7 g of raw material A3 (25.0 mmol), 9.65 g of raw material 1-bromo-2,6-difluorobenzene (50 mmol), and 21.2 g of cesium carbonate (65.0 mmol) into 150 mL of anhydrous DMF (N,N-dimethylformamide). Stir the reaction system at 160 °C for 18 hours, then cool to room temperature and pour it into ice water (2 L). Filter out the white solid, dry it in vacuo, and further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate F-Br-3, a white solid, with a yield of 75%.

[0207] Step 2: Add 8.0 g of raw material A7 (25.0 mmol), 7.6 g of raw material F-Br-3 (16.7 mmol), and 16.3 g of cesium carbonate (50.0 mmol) into 100 ml of anhydrous DMF (N,N-dimethylformamide). Stir the reaction system at 160 °C for 18 hours, then cool to room temperature and pour it into ice water (2 L). Filter out the white solid, dry it in vacuo, and further purify it by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain intermediate Br-A37, a white solid, with a yield of 71%.

[0208] Step 3: Under the protection of a nitrogen atmosphere, slowly add 17.0 mL of a n-hexane solution of tert-butyllithium (22.0 mmol) to a 70 mL solution of tert-butylbenzene containing 8.27 g of intermediate Br-A37 (11.0 mmol) at -30 °C. Slowly warm up to 60 °C, stir for 2 hours, then remove n-hexane in vacuo, and then cool to -30 °C. Add 2.1 mL of boron tribromide (22.0 mmol), and stir the reaction mixture at room temperature for 1 hour. Then add 3.9 mL of N,N-diisopropylethylamine (22.0 mmol) at 0 °C, and then raise the reaction mixture to 130 °C and continue to stir for 5 hours, and then cool to room temperature. Add 5 ml of methanol to the reaction mixture to quench the residual boron tribromide. Concentrate the reaction system in vacuo and purify it by column chromatography using a mixture of dichloromethane / petroleum ether as the eluent to obtain 4.3 g of the target intermediate BN-A37, a yellow solid, with a yield of 56%.

[0209] Step 4: At room temperature, 4.0 g of BN-A37 (5.7 mmol) and 1.49 g of bis(pinacolato)diboron (11.4 mmol) were added to tetrahydrofuran (75 mL). The mixture was bubbled with nitrogen for 10 minutes, and 30.6 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.114 mmol) and 37.8 mg of methoxy(cyclooctadiene)iridium(III) dimer (0.057 mmol) were added under a high flow of nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain 3.6 g of BN-A37-Bpin, which was a yellow solid with a yield of 77%.

[0210] Step 5: 1.03 g of Br-B1 (2.6 mmol), 1.65 g of BN-A37-Bpin (2.0 mmol), 1.27 g of potassium phosphate (6.0 mmol) and water (100 μL) were added to dioxane (45 mL). The mixture was bubbled with nitrogen for 10 minutes, and 36.9 mg of Pd(dppf)Cl2 (0.05 mmol) was added under a high flow of nitrogen. The mixture was heated to 90 °C and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was heated and evaporated to dryness under vacuum, and then purified by column chromatography to obtain 1.14 g of the precursor BN-M-16, which was a yellow solid with a yield of 57%.

[0211] Step 6: 797 mg of BN-M-16 (0.8 mmol) and 378.4 mg of PIFA ([bis(trifluoroacetoxy)iodo]benzene) (0.88 mmol) were added to 20 mL of anhydrous dichloromethane. The mixture was bubbled with nitrogen for 10 minutes, and 256.6 mg of boron trifluoride ethyl etherate (1.76 mmol) was slowly added dropwise at -40 °C. After the reaction mixture was kept at -40 °C and stirred for 1.5 hours, 3 mL of methanol was added to the reaction system to quench the residual boron trifluoride ethyl etherate. The reaction mixture was extracted with dichloromethane and water. The organic phase was heated and evaporated to dryness under vacuum, and then purified by column chromatography to obtain 326 mg of the final product BN-16, which was an orange solid with a yield of 41%.

[0212] Synthesis of the second and third types of compounds (BN-30 to BN-105):

[0213]

[0214] General synthetic reaction process route:

[0215] The second type of compounds is based on the intermediate BN-Ai-Bpin (i = 1 - 19) synthesized from the first type of compounds. Using it as a raw material, the precursor BN-M-n (n = 30 - 105) is obtained through sukuzi coupling, and finally the end product BN-n (n = 30 - 105) is obtained through a one-step oxidative ring closure.

[0216] In the first step, the heterocyclic-substituted arylboronic acid compound Bj (B2 - B5) (4.0 mmol), 2.26 g of o-bromoiodobenzene (8.0 mmol), 2.54 g of potassium phosphate (12.0 mmol), and water (3 mL) are added to tetrahydrofuran (50 mL). The mixture is bubbled with nitrogen for 10 minutes, and 115.6 mg of tetrakis(triphenylphosphine)palladium(0) (0.1 mmol) is added under a high flow of nitrogen. The mixture is heated to reflux and stirred for 12 hours. After the reaction system is cooled to room temperature, the reaction mixture is extracted with dichloromethane and water. The organic phase is heated and spun dry under vacuum, and then purified by column chromatography to obtain the intermediate Br-Bj (j = 2 - 5).

[0217] In the second step, the brominated heterocyclic aryl compound Br-Bj (j = 2 - 5) (1.2 mmol), BN-Ai-Bpin (1.0 mmol), 636 mg of potassium phosphate (3 mmol), and water (0.75 mL) are added to tetrahydrofuran (25 mL). The mixture is bubbled with nitrogen for 10 minutes, and 28.9 mg of tetrakis(triphenylphosphine) (0.025 mmol) is added under a high flow of nitrogen. The mixture is heated to reflux and stirred for 12 hours. After the reaction system is cooled to room temperature, the reaction mixture is extracted with dichloromethane and water. The organic phase is heated and spun dry under vacuum, and then purified by column chromatography to obtain the precursor BN-M-n (n = 30 - 105).

[0218] In the third step, BN-M-n (0.6 mmol) is added to 20 mL of anhydrous dichloromethane. The mixture is bubbled with nitrogen for 10 minutes, and a solution of 12 mL of iron(III) chloride (6.0 mmol) in nitromethane is slowly added dropwise at 0 °C. After the reaction mixture is stirred at room temperature for 2 hours, 10 mL of methanol is added to the reaction system to quench the reaction. The reaction mixture is extracted with dichloromethane and water. The organic phase is heated and spun dry under vacuum, and then purified by column chromatography to obtain the end product BN-n (n = 30 - 105).

[0219] The relevant data of the obtained target compounds are shown in Table 2.

[0220] Taking the compound BN-32 as an example to illustrate the specific details of the synthesis example experiment:

[0221] First step: Add 1.0 g of benzofuran boronic acid B2 (6.2 mmol), 3.51 g of o-bromoiodobenzene (12.4 mmol), 3.94 g of potassium phosphate (18.6 mmol) and water (5 mL) to tetrahydrofuran (70 mL). Bubble the mixture with nitrogen for 10 minutes, and add 115.6 mg of tetrakis(triphenylphosphine)palladium(0) (0.1 mmol) under high-flow nitrogen. Heat the mixture to reflux and stir for 12 hours. After the reaction system cools to room temperature, extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain 1.18 g of Br-B2, a white solid, with a yield of 70%.

[0222] Second step: Add 644.3 mg of Br-B2 (2.36 mmol), 1.5 g of BN-A3-Bpin (1.97 mmol), 1.25 g of potassium phosphate (5.91 mmol) and water (1.5 mL) to tetrahydrofuran (40 mL). Bubble the mixture with nitrogen for 10 minutes, and add 57.8 mg of tetrakis(triphenylphosphine)palladium(0) (0.05 mmol) under high-flow nitrogen. Heat the mixture to reflux and stir for 12 hours. After the reaction system cools to room temperature, extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain 872 mg of the precursor BN-M-32, a yellow solid, with a yield of 53%.

[0223] Third step: Add 600 mg of BN-M-32 (0.72 mmol) to 25 mL of anhydrous dichloromethane. Bubble the mixture with nitrogen for 10 minutes, slowly dropwise add 15 mL of a nitromethane solution of iron(III) chloride (7.2 mmol) at 0 °C. After stirring the reaction mixture at room temperature for 2 hours, add 12 mL of methanol to quench the reaction. Extract the reaction mixture with dichloromethane and water, heat and spin-dry the organic phase under vacuum, and then purify it by column chromatography to obtain 330 mg of the final product BN-32, an orange-yellow product, with a yield of 55%.

[0224] The products were characterized. The test instrument used for elemental analysis was VarioMicro Cube from Agilent Technologies, USA, and the tested elemental types were C, H, N, and S. The instrument used for mass spectrometry testing was the Thermo Fisher TSQEndura ultra-high performance liquid chromatography tandem triple quadrupole mass spectrometer.

[0225] The results of relevant photophysical tests on the compounds showed that: Taking the compound BN-3 as an example, its emission in toluene solution (1×10 -5 M) at room temperature was 532 nm, and the full width at half maximum was 36 nm.

[0226] The test on the electroluminescence properties of the compound shows that: taking the compound BN-3 as an example, the spectral emission peak position of the device with PhCzBCz: 5wt% BN-3 as the emission layer is 540 nm, and the full width at half maximum is 39 nm.

[0227] Table 1. Summary of product data of synthesis examples (the first type of compound)

[0228]

[0229]

[0230] Table 2. Summary of product data of synthesis examples (the second and third types of compounds)

[0231]

[0232]

[0233]

[0234] Examples of electroluminescent devices

[0235] Some representative examples of electroluminescent devices are given below. The molecular structures of some materials involved in the device examples are as follows:

[0236] Examples of electroluminescent devices

[0237] 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:

[0238]

[0239]

[0240] The following are examples of electroluminescent devices prepared using the materials of the present invention. The specific device preparation process is as follows:

[0241] Preparation process of organic electroluminescent devices:

[0242] The results of the device are as Figure 1 shown, where 1 is the ITO anode, 2 is the first hole transport layer, 3 is the second hole transport layer, 4 is the emission 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.

[0243] The preparation process is as follows:

[0244] (1) Substrate treatment: The transparent ITO glass is used as the substrate material for fabricating the device. First, it is ultrasonically treated with 5% ITO cleaning solution for 30 min, and then successively ultrasonically washed with distilled water (twice), acetone (twice), and isopropanol (twice). Finally, the ITO glass is stored in isopropanol. Before each use, the surface of the ITO glass is carefully wiped with acetone cotton balls and isopropanol cotton balls, dried after being rinsed with isopropanol, and then treated with plasma for 5 min for standby. The fabrication of the device is completed by combining spin coating and vacuum evaporation processes.

[0245] (2) Preparation of hole injection layer and hole transport layer: The hole transport layer is prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reaches below 5×10 -4 Pa, evaporation starts. The deposition rate is measured by a Sciencetech film thickness gauge. Using the vacuum evaporation process, the organic hole transport layer is successively deposited on the ITO electrode surface. The deposition rate of the hole transport material is

[0246] (3) Preparation of light-emitting layer: The light-emitting layer is prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reaches below 5×10 - 4 Pa, evaporation starts. The deposition rate is measured by a Sciencetech film thickness gauge. Using the vacuum evaporation process, the light-emitting layer is successively deposited on the hole transport layer. The deposition rate of the light-emitting layer material is

[0247] (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 the vacuum evaporation system reaches below 5×10 -4 Pa, evaporation starts. The deposition rate is measured by a Sciencetech film thickness gauge. Using the vacuum evaporation process, the organic electron transport layer, LiF electron injection layer and metal Al electrode are successively deposited on the light-emitting layer (the specific device structure is shown in the following effect examples). Among them, the deposition rate of the organic material is The deposition rate of LiF is The deposition of Al

[0248] Device Example 1 - n (n = 60)

[0249] In the organic electroluminescent devices in Device Examples 1 - n (n = 1 - 60) (the structure is as Figure 1As shown in [description], HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-18 is used as the host material in the light-emitting layer, BN-m (m represents the last digit of the code of the light-emitting material used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 99 wt% H1-18 + 1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0250] The performance data of the device embodiments are shown in Table 3. The device lifetime (T50, hours) in Table 3 refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m 2 . The time required when). Comparative device embodiments D1-n (n = 1 - 14)

[0251] In the organic electroluminescent devices in comparative device embodiments 1-n (n = 1 - 14) (the structure is as Figure 1 shown), HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-18 is used as the host material in the light-emitting layer, R-m (m represents the last digit of the code of the light-emitting material used in the comparative device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 99 wt% H1-18 + 1 wt% R-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0252] The performance data of the comparative device examples are shown in Table D3. The characteristics of the device such as current, voltage, luminance, and electroluminescence spectrum are synchronously measured using a Photo Research PR 655 spectral 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 from the current density, luminance, and electroluminescence spectrum combined with the visibility function under the condition that the emission is Lambertian distribution (the same hereinafter). The device lifetime (T50, hours) in Table D3 refers to the time required when the initial luminance of the device is 1000 cd / m 2 , and the luminance of the device drops to 50% of the initial luminance (i.e., the luminance of the device drops to 500 cd / m 2 ).

[0253] Table 3

[0254]

[0255]

[0256]

[0257] Figure 2 is the electroluminescence spectrum of the device using compound BN-3, with its emission peak at 536 nm and a full width at half maximum of 38 nm.

[0258] Figure 3 is the electroluminescence spectrum of the device using compound BN-32, with its emission peak at 552 nm and a full width at half maximum of 41 nm.

[0259] Figure 4 is the electroluminescence spectrum of the device using compound BN-51, with its emission peak at 552 nm and a full width at half maximum of 40 nm.

[0260] Figure 5 is the electroluminescence spectrum of the device using compound BN-70, with its emission peak at 552 nm and a full width at half maximum of 41 nm.

[0261] Figure 6 is the electroluminescence spectrum of the device using compound BN-89, with its emission peak at 548 nm and a full width at half maximum of 42 nm.

[0262] Table D3

[0263]

[0264] Device Example 2-n (n = 1 - 60)

[0265] In the organic electroluminescent device in Device Example 2-n (n = 1 - 60) (the structure is as Figure 1As shown in [description], HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, in the light-emitting layer, H1-18 + TRZ-77 is used as the host material, 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-77 is used as the second electron transport layer, ETL-1 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 organic electroluminescent device structure of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-18 + 29 wt% TRZ-77 + 1 wt% BN-m (30 nm) / ETL-1 (10 nm) / TRZ-6 (30 nm) LiF (1 nm) / Al (100 nm)].

[0266] The performance data of the device embodiment are shown in Table 4. The device lifetime (T50, hours) in Table 4 refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m 2 ). The comparative device embodiments are D2-n (n = 1 - 14)

[0267] In the organic electroluminescent devices in the comparative device embodiments 2-n (n = 1 - 14) (the structure is as Figure 1 shown), HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, in the light-emitting layer, H1-18 + TRZ-77 is used as the host material, R-m (m represents the last digit of the light-emitting material code used in the comparative device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 organic electroluminescent device structure of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / / 70 wt% H1-18 + 29 wt% TRZ-77 + 1 wt% R-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0268] The performance data of the comparative device embodiments are shown in Table D4. The device lifetime (T50, hours) in Table D4 refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m2 The time required when...

[0269] Table 4

[0270]

[0271]

[0272] Table D4

[0273]

[0274]

[0275] Device Example 3-n (n = 1 - 60)

[0276] In the organic electroluminescent device in Device Example 3-n (n = 1 - 60) (the structure is as Figure 1 shown), the HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-245 + 2CN-47 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 example) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 Effect Example is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-245 + 29 wt% 2CN-47 + 1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0277] The performance data of the device examples are shown in Table 5. The device lifetime (T50, hours) in Table 5 refers to the time required when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., the device brightness drops to 500 cd / m 2 when). Comparative Device Example D3-n (n = 1 - 14)

[0278] In the organic electroluminescent device in Comparative Device Example 3-n (n = 1 - 14) (the structure is as Figure 1As shown, HATCN-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-245 + 2CN-47 is used as the host material in the light-emitting layer, R-m (where m represents the last digit of the code of the light-emitting material used in the comparative device example) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-78 is used as the second electron transport layer, TRZ-6 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 effect example is [ITO / 15 wt% HATCN + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-245 + 29 wt% 2CN-47 + 1 wt% R-m (30 nm) / TRZ-78 (10 nm) / TRZ-6 (30 nm) LiF (1 nm) / Al (100 nm)].

[0279] The performance data of the comparative device example are shown in Table D5. In Table D5, the device lifetime (T50, hours) refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m 2 ).

[0280] Table 5

[0281]

[0282]

[0283]

[0284] Table D5

[0285]

[0286] Device Example 4-n (n = 1 - 60)

[0287] In the organic electroluminescent device in Device Example 1-n (n = 1 - 60) (the structure is as Figure 1As shown, HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-18 + IrPPy 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 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-18 + 9 wt% IrPPy + 1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0288] The performance data of the device embodiment are shown in Table 6. In Table 6, the device lifetime (T50, hours) refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m 2 ). The comparative device embodiments are D4-n (n = 1 - 14)

[0289] In the organic electroluminescent devices in the comparative device embodiments 1-n (n = 1 - 14) (the structure is as Figure 1 shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-18 + IrPPy3 is used as the host material in the light-emitting layer, R-m (m represents the last digit of the light-emitting material code used in the comparative device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-77 is used as the second electron transport layer, ETL-1 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 effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-18 + 9 wt% IrPPy3 + 1 wt% R-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0290] The performance data of the comparative device embodiments are shown in Table D6. In Table D6, the device lifetime (T50, hours) refers to the time when the initial brightness of the device is 1000 cd / m 2 , when the brightness of the device drops to 50% of the initial brightness (i.e., when the device brightness drops to 500 cd / m2 The time required when

[0291] Table 6

[0292]

[0293]

[0294] Table D6

[0295]

[0296] The applicant declares that the present invention uses the above embodiments to illustrate the boron nitride compound and its application of the present invention, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent replacement of the raw materials selected for the present invention, the addition of auxiliary components, the selection of specific methods, etc. all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. A boron nitride compound, characterized in that, The boron nitride compound has a structure shown in the following formula I: R 1 、 R 2 、 R 3 and R 4 are independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted with one or more R a , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R a , diphenylamino, or diphenylamino substituted with one or more R a ; R a Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R b groups, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R b groups, diphenylamino, or diphenylamino substituted with one or more R b groups; R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c groups, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R c groups, diphenylamino, or diphenylamino substituted with one or more R c groups; R c each occurrence independently is deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R d groups, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R d groups, diphenylamino, or diphenylamino substituted with one or more R d groups; R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 aryl substituted by one or more R e substituents; R e Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 1 、R 2 、R 3 and R 4 may exist independently or R 1 、R 2 、R 3 and R 4 at least one of them forms a ring with the adjacent aromatic ring; R 11 、R 12 、R 13 and R 14 are independently selected from H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, C6-C18 aryl substituted with one or more R f , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R f , diphenylamino, or diphenylamino substituted with one or more R f ; R f Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R g groups, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R b groups, diphenylamino, or diphenylamino substituted with one or more R g groups; R g Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c substituted C6-C14 aryl, 5- to 18-membered heteroaryl; R 11 、R 12 、R 13 and R 14 exist independently respectively or R 11 、R 12 、R 13 and R 14 At least one of them forms a ring with the adjacent aromatic ring; E is wherein the wavy line represents the connection site of the group; X is S or O; R 21 、R 22 、R 23 、R 24 、R 25 and R 26 are independently H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted with one or more R h substituents, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R h substituents, diphenylamino, or diphenylamino substituted with one or more R h substituents; R h Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R i groups, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R i groups, diphenylamino, or diphenylamino substituted with one or more R g groups; R i Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c substituted C6-C14 aryl, 5- to 18-membered heteroaryl; R 21 、R 22 、R 23 and R 24 exist independently or at least one of R 21 、R 22 、R 23 and R 24 forms a ring with the adjacent aromatic ring; R 25 and R 26 exist independently or R 25 and R 26 at least one of them forms a ring with the adjacent aromatic ring. The alkyl group, alkoxy group, cycloalkyl group, aryl group, and heteroaryl group are optionally substituted with one or more substituents selected from the following: halogen, -CN, C1-C12 alkyl group, C1-C12 alkoxy group, C1-C12 haloalkyl group, C3-C10 cycloalkyl group, C6-C14 aryl group, and 5- to 18-membered heteroaryl group.

2. The boron nitride compound according to claim 1, wherein Said R 1 , R 2 , R 3 and R 4 are independently H, D (deuterium), C1-C12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl, aryl substituted by at least one C1-C 12 alkyl, aryl substituted by at least one C1-C 12 alkoxy, phenyl-C1-C 12 alkyl, diphenylamino, diphenylamino substituted by at least one C1-C 12 alkyl, carbazolyl, carbazolyl substituted by at least one C1-C 12 alkyl; Preferably, said R a is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted by at least one C1-C 12 alkyl, phenyl substituted by at least one C1-C 12 alkoxy, phenyl-C1-C 12 alkyl, diphenylamino, diphenylamino substituted by at least one C1-C 12 alkyl, carbazolyl, carbazolyl substituted by at least one C1-C 12 alkyl; Preferably, said R b is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted by at least one C1-C 12 alkyl, phenyl substituted by at least one C1-C 12 alkoxy, phenyl-C1-C 12 alkyl, diphenylamino, diphenylamino substituted by at least one C1-C 12 alkyl, carbazolyl, carbazolyl substituted by at least one C1-C 12 alkyl; Preferably, said R c is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted by at least one C1-C 12 alkyl, phenyl substituted by at least one C1-C 12 alkoxy, phenyl-C1-C 12 alkyl, diphenylamino, diphenylamino substituted by at least one C1-C 12 alkyl, carbazolyl, carbazolyl substituted by at least one C1-C 12 alkyl; Preferably, the R d is independently deuterium, fluorine, C1-C 12 alkyl, C1-C 12 alkoxy, C3-C 10 cycloalkyl, phenyl substituted by at least one C1-C 12 alkyl, phenyl substituted by at least one C1-C 12 alkoxy, carbazolyl, carbazolyl substituted by at least one C1-C 12 alkyl; Preferably, the R 1 , R 2 , R 3 and R 4 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, Wherein the wavy line represents the connection site of the group; Preferably, the R 1 , R 2 , R 3 and R 4 are independently H, methyl, phenyl, 2-methyl-phenyl, Wherein the wavy line represents the connection site of the group; Preferably, the R 1 , R 2 , R 3 and R 4 are the same and are selected from any one of H, methyl, phenyl, 2-methyl-phenyl, ; wherein R j is H, methyl, isopropyl, tert-butyl or Preferably, R 1 , R 2 , R 3 and R 4 at least one of them forms any one of the following ring structures with the connected aromatic ring: Among them, the key where the * is located is the shared bond with the aromatic ring; Preferably, the R 11 , R 12 , R 13 and R 14 are each independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl; Preferably, the R 21 , R 22 , R 23 , R 24 , R 25 , and R 26 are independently selected from H, deuterium, fluorine, C1-C20 alkyl, C6-C18 aryl, or 5- to 24-membered heteroaryl.

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

4. An organic electroluminescent composition, characterized in that, It includes the boron nitride compound as described in any one of claims 1-3 as a doping material and a host material; Preferably, the host material is a material having electron transport ability and / or hole transport ability and whose triplet excited state energy is higher than or equal to the triplet excited state energy of the doped luminescent material.

5. The organic electroluminescent composition according to claim 4, wherein The host material is a carbazole derivative and / or a carboline derivative having a structure 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; wherein R 1H and R 2H are each independently any one of the following groups: Wherein X1, Y1, and Z1 are CH or N, and at most one of X1, Y1, and Z1 is N; wherein 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, and the asterisk 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 are 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, in the organic electroluminescent composition, 0.3-30.0 wt% of the boron nitride compound as described in any one of claims 1-3 is contained as a doping material, and the remaining 99.7-70.0 wt% of the components are host materials composed of 1-2 compounds having the structures of formulas (H-1) to (H-10); Preferably, the host material contains 2 compounds having the structures of formulas (H-1) to (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, in the organic electroluminescent composition, 0.3-30.0 wt% of the boron nitride compound having the structure shown in formula I as described in any one of claims 1-3 is contained, and the remaining 99.7-70.0 wt% of the components are 1 or 2 compounds among compounds H1-1 to H1-254; Preferably, 2 compounds among compounds H1-1 to H1-254 are contained as host materials in the organic electroluminescent composition, 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 nitride compounds having the structure shown in formula I; the host material is composed of any one of the compounds shown in formulas 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; wherein R 1a , R 1b , R 2a , R 2b , R 3a and R 3b one or two of them are independently R Tz , and the rest are the same or different and independently are hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, C6-C 18 aryl, C1-C8 alkyl-substituted C6-C 18 aryl or C1-C8 alkoxy-substituted C6-C 18 aryl; R Tz is any one of the substituted groups represented by the following formula: Wherein the asterisk represents the connection site of the group; Preferably, the molar ratio between the compound shown in formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A and the compound shown in formulas H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H9, or H-10 in the host material is 1:20 to 20:1; Preferably, the weight ratio between the compound represented by the formulae TRZ-1 to TRZ-82 and the carbazole or carboline derivative represented by the formulae (H-1) to (H-10) in the host material is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is the boron nitride compound described in any one of claims 1-3; the host material is composed of any one of the compounds such as formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by the formulae H-1 to H-10; in the host material, the weight ratio between the compound of 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-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; the host material is composed of any one of the 1,3,5-triazine derivatives represented by the formulae TRZ-1 to TRZ-82 and any one of the carbazole or carboline derivatives represented by the formulae H1-1 to H1-254; in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative represented by the formulae 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 the formulae BN-1 to BN-105; the host material is composed of any one of the compounds such as formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A and any one of the carbazole or carboline derivatives represented by the formulae H1-1 to H1-254. In the host material, the weight ratio between the compound of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carboline derivative represented by the formulae 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 the formulae BN-1 to BN-105; the host material is composed of any one of the 1,3,5-triazine derivatives represented by the formulae TRZ-1 to TRZ-82 and any one of the carbazole or carboline derivatives represented by the formulae H1-1 to H1-254. In the host material, the weight ratio between the 1,3,5-triazine derivative represented by the formulae TRZ-1 to TRZ-82 and the carbazole or carboline derivative represented by the formulae H1-1 to H1-254 is 1:20 to 20:1; Preferably, the host material is composed of any one of the compounds having the structures represented by the formulae H-1 to H-10 and any one of the compounds represented by the 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 1s 、R 2s 、R 3s 、R 4s 、R 5s and R 6s are independently C6-C24 aryl or C12-C36 heteroaryl; R si (i = 7 - 39) is independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl; Preferably, R 1s , R 2s , R 3s , R 4s , R 5s and R 6s are independently selected from any one of the following 24 groups: The asterisk represents the connection site of the group. Preferably, R si is independently selected from any one of the following five groups, where i is an integer from 7 to 39: Preferably, the dopant material in the organic electroluminescent composition is any one of the boron nitride compounds having the structure shown in Formula I as described in any one of Claims 1-3, and the host material is composed of any one of the compounds shown in Formulae 2CN-1 to 2CN-60 and any one of the compounds shown in Formulae H1-1 to H1-254; Preferably, in the organic electroluminescent composition, 0.3-30.0 wt% of the boron nitride compound as described in any one of Claims 1-3 is contained, and the remaining 99.7-70.0 wt% of the components are the host composed of 1-2 compounds having the structures of Formulae (H-1) to (H-10); Preferably, the host material in the composition is 1-2 of the compounds H1-1 to H1-254; Preferably, in the organic electroluminescent composition, 0.3-30.0 wt% of the boron nitride compound as described in any one of Claims 1-3 is contained, and the remaining 99.7-70.0 wt% of the components are 1-2 of the compounds H1-1 to H1-254; Preferably, the dopant material in the organic electroluminescent composition is the boron nitride compound as described in any one of Claims 1-3; 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 shown in Formulae H-1 to H-10; Preferably, the dopant material in the organic electroluminescent composition is the boron nitride compound as described in any one of Claims 1-3; the host material (with a content of 99.7 wt-70.0 wt%) is composed of any one of the 1,3,5-triazine derivatives shown in Formulae TRZ-1 to TRZ-82 and any one of the carbazole or carboline derivatives shown in Formulae H1-1 to H1-254; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds shown in Formulae BN-1 to BN-105; the host material is composed of any one of the compounds of Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of the carbazole or carboline derivatives shown in Formulae H1-1 to H1-254; Preferably, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is the boron nitride compound as described in any one of Claims 1-3; 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 shown in Formulae H-1 to H-10; Preferably, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is a boron nitride compound as described in any one of claims 1-3; 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 carbazole or carboline derivatives represented by formulas H1-1 to H1-254; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-105; 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 carbazole or carboline derivatives represented by formulas H1-1 to H1-254; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-105, 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 carbazole or carboline derivatives represented by formulas H1-1 to H1-254; Preferably, the dopant material in the organic electroluminescent composition is a boron nitride compound as described in any one of claims 1-3, and the host material is composed of any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir represented by formulas Ir-1 and Ir-2; R ri independently hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, where i is an integer from 1 to 22, where the dashed line represents that two of the four included bonds that are spaced apart are double bonds; R ri Any one of the groups may form a ring with the aromatic ring or aromatic heterocycle to which it is attached; Preferably, the phosphorescent compound containing metal Ir is any one of the following compounds: Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-105, and the host material is composed of any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir represented by formulas Ir-1 and Ir-2; 6. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes a boron nitride compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer includes a boron nitride compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5.

8. The organic electroluminescent device according to claim 7, wherein 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 includes a boron nitride compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in 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 includes a boron nitride compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5; Preferably, the organic electroluminescent device further includes 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 7-9 in an organic electroluminescent display or an organic electroluminescent lighting source.

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