Boron-nitrogen compound and application thereof

Abstract

The invention provides a boron-nitrogen compound and application thereof, the boron-nitrogen compound has a structure as shown in a formula I and a formula II, the boron-nitrogen compound not only realizes fine adjustment of a spectrum, but also further improves luminous efficiency through extension conjugation and introduction of double B atoms. The boron-nitrogen compound has a narrow spectrum and is used as a narrow-spectrum luminescent material for preparing a luminescent layer of an organic electroluminescent device, the prepared organic electroluminescent device realizes narrow-spectrum TADF emission, the electroluminescent spectrum is in a green light-yellow light area, the half-peak width is less than 40nm, and the boron-nitrogen compound has a wide application prospect. And the highest external quantum efficiency of electroluminescence of the device reaches up to 30% or above.

Description

Technical Field

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

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

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

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

[0005] TADF molecules are mainly doped as guest materials in wide band gap 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). Unlike the localized (LE) state emission of traditional fluorescent molecules, TADF emission is mainly derived from the transition of ICT state, thus is easily affected by the intermolecular vibration and rotation, resulting in a wide emission spectrum and long delayed fluorescence excited state lifetime, thus leading to poor stability of the electroluminescent device based on TADF light emitting materials. Although pure organic TADF light emitting materials get rid of the dependence on noble metals and have the advantage of low cost, due to the poor color purity of the emission spectrum and the defects in stability, it is the main problem faced by organic TADF light emitting materials. SUMMARY

[0006] In view of the deficiencies of the prior art, the purpose of the present application is to provide a boron-nitrogen compound and its application. The compound provided by the present application aims to solve the defects of TADF light emitting molecules, provide light emitting materials with narrow emission spectrum and good stability, and be used for preparing light emitting layer of organic electroluminescent device, so that the organic electroluminescent device shows excellent characteristics.

[0007] In order to achieve the purpose of the present application, the following technical solutions are adopted:

[0008] In one aspect, the present application provides a boron-nitrogen compound, which has the following structure of formula I and formula II:

[0009]

[0010] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R a Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R a substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R a substituted diphenylamino groups;

[0011] R a Each occurrence is independently deuterium, fluorine, CN, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 12 Cycloalkyl, C6~C 14 Aryl, one or more R b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R b substituted diphenylamino groups;

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

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

[0014] R d independently at each occurrence is deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; e substituted C6-C14 aryl;

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

[0016] R 1 and R 2 are each present independently or R 1 and R 2 form a ring with the aromatic ring to which they are attached;

[0017] R 3 and R 4 are each present independently or R 3 and R 4 form a ring with the aromatic ring to which they are attached;

[0018] R 5 , R 6 , and R 7 are each present independently or R 5 , R 6 , and R 7 form a ring with the aromatic ring to which they are attached;

[0019] R 8 , R 9 , and R 10 are each present independently or R 8 , R 9 , and R 10 form a ring with the aromatic ring to which they are attached;

[0020] R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R43 and R 44 are independently selected from H, deuterium, fluorine, CN, C1-C20alkyl, C1-C20alkoxy, C3-C10cycloalkyl, C6-C18aryl or C6-C18aryl substituted by one or more R f substituted C6-C18aryl;

[0021] R f are independently at each occurrence deuterium, fluorine, CN, C1-C12alkyl, C1-C12alkoxy, C3-C12cycloalkyl, C6-C18aryl or C6-C18aryl substituted by one or more R g substituted C6-C18aryl;

[0022] R g are independently at each occurrence deuterium, fluorine, CN, C1-C12alkyl, C1-C12alkoxy, C3-C10cycloalkyl or C6-C14aryl;

[0023] R 11 , R 12 , R 13 , R 14 and R 15 are each present independently or at least one of R 11 , R 12 , R 13 , R 14 and R 15 forms a ring with the aromatic ring to which it is attached;

[0024] R 21 , R 22 , R 23 , R 24 and R 25 are each present independently or at least one of R 21 , R 22 , R 23 , R 24 and R 25 forms a ring with the aromatic ring to which it is attached;

[0025] R 31 , R 32 , R 33 and R 34 are each present independently or at least one of R 31 , R 32 , R 33 and R 34 forms a ring with the aromatic ring to which it is attached;

[0026] R 41 , R 42 , R 43 and R 44 are each present independently or at least one of R 41 , R42 、R 43 and R 44 At least one of them forms a ring with the connected aromatic ring;

[0027] X is S, O or Se;

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

[0029] In some embodiments of the present invention, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, D (deuterium), C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl, C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl;

[0030] Preferably, the R a Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl;

[0031] Preferably, the R b Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl;

[0032] Preferably, the R c Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl;

[0033] Preferably, the R d Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, carbazolyl, at least one C1-C 12 Alkyl-substituted carbazolyl;

[0034] Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 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]

[0036] The wavy lines represent the attachment sites of the groups;

[0037] Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, methyl, 2-methyl-phenyl, Phenyl, The wavy lines represent the attachment sites of the groups;

[0038] Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, methyl, 2-methyl-phenyl, Phenyl, Any of the following;

[0039] Preferably, the R 1 、R 2 、R 3 and R 4 are independently H, methyl, 2-methyl-phenyl, Phenyl, Any one of R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H or deuterium;

[0040] Preferably, the R 1 and R 4 are independently H or deuterium, R 2 and R 3 Same as H, methyl, 2-methyl-phenyl, Phenyl, Any one of R 5 、R6 , R 7 , R 8 , R 9 and R 10 are independently H or deuterium;

[0041] Preferably, R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 34 , R 42 , R 43 and R 44 are independently selected from H, deuterium, C1-C4 alkyl or C6-C12 aryl;

[0042] Preferably, R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 34 , R 42 , R 43 and R 44 are independently selected from H, methyl, or phenyl;

[0043] Preferably, R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 34 , R 42R 43 and R 44 at least one of R

[0044] wherein the bond marked with * is a bond shared with the aromatic ring.

[0045] Preferably, X is S.

[0046] In some embodiments of the present application, the boron-nitrogen compound is any one of the following compounds:

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] In another aspect, the present application provides an organic electroluminescent material comprising the boron-nitrogen compound as described above.

[0054] In another aspect, the present application provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising the boron-nitrogen compound as described above.

[0055] Preferably, the organic thin film layer comprises a light-emitting layer, an optional hole-injection layer, an optional hole-transport layer, an optional electron-transport layer, and an optional electron-injection layer, wherein at least one of the light-emitting layer, the electron-injection layer, the electron-transport layer, the hole-transport layer, and the hole-injection layer comprises the boron-nitrogen compound as described above.

[0056] In the present application, the boron-nitrogen compound having the structure shown in Formula I and Formula II can be used as a functional material in at least one of a light-emitting layer, an electron-injection layer, an electron-transport layer, a hole-transport layer, and a hole-injection layer of an organic electroluminescent device.

[0057] In one embodiment, the organic electroluminescent device of the present application can further comprise an optional hole-blocking layer, an optional electron-blocking layer, and an optional capping layer, etc.

[0058] In one embodiment, the organic electroluminescent device has a structure as shown in Figure 1In the structure shown, 1 is an ITO anode, 2 is a first hole transport layer, 3 is a second hole transport layer, 4 is a light-emitting layer, 5 is a second electron transport layer, 6 is a first electron transport layer, 7 is an electron injection layer, and 8 is a metal cathode.

[0059] In one embodiment, the boron nitrogen compounds having the structures shown in Formula I and Formula II are used to prepare the light-emitting layer in an organic electroluminescent device.

[0060] In one embodiment, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes a light-emitting layer containing the boron nitrogen compound as described above, and may also include any one or a combination of multiple of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0061] In another aspect, the present invention provides an organic electroluminescent composition comprising the boron nitrogen compound as described above as a doping material and a host material;

[0062] Preferably, the host material is a material having electron transport capability and / or hole transport capability and having triplet excited state energy equal to or higher than triplet excited state energy of the dopant material.

[0063] In one embodiment of the present invention, the host material is a carbazole derivative and / or a carboline derivative having a structure as shown in any one of Formula (H-1) to Formula (H-10):

[0064]

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

[0066] where R 1H and R 2H Independently any 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] where R aH and R bH are independently H, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or C1-C20 Alkoxy-substituted C6-C 20 Aryl, * represents the attachment site of the group;

[0070] W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 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, the organic electroluminescent composition preferably contains 0.3-30.0 wt% (e.g., 0.3 wt%, 0.5 wt%, 1 wt%, 3 wt%, 5 wt%, 8 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt%, 23 wt%, 25 wt%, 28 wt% or 30 wt%) of the boron nitrogen compound described above as a dopant material, and the remaining 99.7-70.0 wt% (e.g., 99.7 wt%, 99 wt%, 98 wt%, 95 wt%, 93 wt%, 90 wt%, 88 wt%, 85 wt%, 83 wt%, 80 wt%, 78 wt% or 77 wt%) of the component is a host material composed of 1-2 compounds having structures of Formula (H-1) to (H-10);

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

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

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] In one embodiment of the present application, the organic electroluminescent composition contains 0.3 to 30.0 wt% (for example, the weight percentage can be 0.3 wt%, 0.5 wt%, 1 wt%, 3 wt%, 5 wt%, 8 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt%, 23 wt%, 25 wt%, 28 wt%, or 30 wt%) of the boron-nitrogen compound having the structure of Formula I and Formula II as described above, and the remaining 99.7 to 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 is one or two compounds selected from the group consisting of compounds H1-1 to H1-254.

[0087] In one preferred embodiment of the present application, the organic electroluminescent composition contains two compounds selected from the group consisting of compounds H1-1 to H1-254 as the host material, and the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, and the like.

[0088] In a certain embodiment of the present application, the dopant material in the organic electroluminescent composition is any one of the boron-nitrogen compounds of the structures of Formula I and Formula II (0.3 wt-30.0 wt%); the host material (99.7 wt-70.0 wt%) is 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 of Formula H-1 to H-10.

[0089] In a preferred embodiment, the amount ratio between the compound of Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compound of Formula H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0090]

[0091] wherein 1 or 2 of R 1a , R 1b , R 2a , R 2b , R 3a and R 3b are independently R Tz , and the rest are the same or different and are independently hydrogen, deuterium, C1-C8alkyl, C1-C8alkoxy, C6-C 18 aryl, C1-C8alkyl-substituted C6-C 18 aryl or C1-C8alkoxy-substituted C6-C 18 aryl; R Tz is any one of the following substituent groups:

[0092]

[0093]

[0094]

[0095] wherein the asterisk represents the site of attachment of the group;

[0096] In a preferred embodiment, the weight ratio between the compound represented by any one of formulae TRZ-1 to TRZ-86 and the carbazole or carboline derivative represented by any one of formulae (H-1) to (H-10) in the host material is 1:20 to 20:1, for example 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0097] In a preferred embodiment, 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 formula I and formula II (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, 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 Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9, or H-10 is 1:20 to 20:1, for example 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0098] In a preferred embodiment, 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 formula I and formula II (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 TRZ-1 to TRZ-86 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 derivative and the carbazole or carboline derivative is 1:20 to 20:1, for example 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0099] In a preferred embodiment, the organic electroluminescence composition is a light-emitting layer; the dopant material in the organic electroluminescence composition is any one of the compounds represented by formulae BN-1 to BN-155 (content: 0.3 wt% to 30.0 wt%); the host material (content: 99.7 wt% to 70.0 wt%) consists 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 the carbazole or carboline derivatives represented by formulae H1-1 to H1-254. For example, 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 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0100] In a preferred embodiment, the organic electroluminescence composition is a light-emitting layer; the dopant material in the organic electroluminescence composition is any one of the compounds represented by formulae BN-1 to BN-155 (content: 0.3 wt% to 30.0 wt%); the host material (content: 99.7 wt% to 70.0 wt%) consists of any one of the compounds represented by formulae TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by formulae H1-1 to H1-254. For example, the weight ratio between the compounds represented by formulae TRZ-1 to TRZ-86 and the carbazole or carboline derivatives represented by formulae H1-1 to H1-254 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0101]

[0102]

[0103]

[0104]

[0105] In the present application, the host material in the organic electroluminescent composition is constituted by any one of the compounds having the structures shown in the formulae H-1 to H-10 and any one of the compounds shown in the formulae Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6.

[0106]

[0107] Y1, Y2, Y3, Y4, Y5, Y6, Y7and Y8are independently O (oxygen) or S (sulfur);

[0108] R s1 , R s2 , R s3 , R s4 , R s5 and R s6 are independently C6-C24aryl or C12-C36heteroaryl;

[0109] R si (i = 7-39) are independently H, deuterium, C1-C6alkyl, C1-C6alkoxy or C6-C24aryl;

[0110] Preferably, R s1 , R s2 , R s3 , R s4 , R s5 and R s6 are independently selected from any one of the following 24 groups:

[0111]

[0112]

[0113] The asterisk represents the connecting site of the group.

[0114] Preferably, R si (i = 7-39) are independently selected from any one of the following 5 groups:

[0115] The asterisk represents the connecting site of the group.

[0116] Preferably, the dopant material in the organic electroluminescent composition is any one of the boron-nitrogen compounds having the structures shown in the formulae I and II as described above, and the host material is constituted by any one of the compounds shown in the formulae 2CN-1 to 2CN-60 and any one of the compounds shown in the formulae H1-1 to H1-254;

[0117]

[0118]

[0119]

[0120]

[0121] In one embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition can be a carbazole derivative and / or a carbolin derivative as shown in formula (H-1) to formula (H-10). In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any one compound shown in formula I and formula II, and the remaining 99.7-70.0 wt% of the composition is a host consisting of 1-2 compounds having the structure of formula (H-1) to formula (H-10). For example, when the host contains 2 compounds having the structure of formula (H-1) to formula (H-10), the weight ratio of the two compounds is 1:5 to 5:1, for example 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0122] In one embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the host material in the composition is 1-2 compounds selected from compounds H1-1 to H1-254. In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any one compound shown in formula I, and the remaining 99.7-70.0 wt% of the composition is 1-2 compounds selected from compounds H1-1 to H1-254. For example, when the composition contains 2 compounds selected from compounds H1-1 to H1-254, the weight ratio of the two compounds is 1:5 to 5:1, for example 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0123] In an embodiment of the present application, 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 Formula I and Formula II (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 compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A and any one of the compounds represented by 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, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0124] In an embodiment of the present application, 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 Formula I and Formula II (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 1,3,5-triazine derivatives represented by Formula TRZ-1 to TRZ-86 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 derivative and the carbazole or carboline derivative is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0125] In one embodiment of the present application, 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 formula BN-1 to BN-155 (content: 0.3 wt% to 30.0 wt%); and the host material (content: 99.7 wt% to 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 the carbazole or carboline derivatives represented by formulae H1-1 to H1-254. For example, 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 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0126] In one embodiment of the present application, 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 formula I and formula II (content: 0.3 wt% to 30.0 wt%); and the host material (content: 99.7 wt% to 70.0 wt%) is composed of any one of the compounds represented by formulae Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5, or Ph-2CN-6 and any one of the compounds represented by formulae H-1 to H-10. For example, the weight ratio between the compounds represented by formulae Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5, or Ph-2CN-6 and the compounds represented by formulae H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9, or H-10 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0127] In a certain embodiment of the present application, 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 Formula I and Formula II (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 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, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, and the like.

[0128] In a certain embodiment of the present application, 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 Formula BN-1 to BN-155 (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 compounds represented by 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 carbazole or carboline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the compound represented by Formula 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 Formula H1-1 to H1-254 is 1:20 to 20:1.

[0129] In an embodiment of the present application, the organic electroluminescence composition is a light-emitting layer; the dopant material in the organic electroluminescence composition is any one of the compounds represented by formula BN-1 to BN-155 (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 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, the weight ratio between the dicyanobenzene derivative represented by formula 2CN-1 to 2CN-60 and the carbazole or carboline derivative represented by formula H1-1 to H1-254 in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0130] In an embodiment of the present application, the organic electroluminescence composition is a light-emitting layer; the dopant material in the organic electroluminescence composition is any one of the compounds represented by formula I and formula II (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 formula H1-1 to H1-254 and the phosphorescent compound containing metal Ir or Pt represented by formula Ir-1, formula Ir-2, and Pt-1. For example, the weight ratio between the carbazole or carboline derivative represented by formula H1-1 to H1-254 and the phosphorescent compound containing metal Ir in the host material is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0131]

[0132] R ri independently hydrogen, deuterium, C1-C18alkyl or C6-C18aryl, wherein i is an integer from 1 to 22, wherein the dotted line represents that of the four bonds comprised, the two bonds spaced apart are double bonds;

[0133] R ri any one of the groups can form a ring with the aromatic or aromatic heterocyclic ring to which it is attached;

[0134] Preferably, the phosphorescent compound containing metal Ir or Pt is any one of the following compounds:

[0135]

[0136]

[0137] In one embodiment of the present application, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formula BN-1 to BN-155 (content: 0.3 wt% to 30.0 wt%), and the host material (content: 99.7 wt% to 70.0 wt%) is composed of any one of the carbazole or carbolin derivatives represented by formula H1-1 to H1-254 and the phosphorescent compound containing Ir or Pt represented by formula Ir-1 and formula Ir-2. For example, the weight ratio between the carbazole or carbolin derivative represented by formula H1-1 to H1-254 and the phosphorescent compound containing Ir or Pt in the host material is 1:20 to 20:1.

[0138] In another aspect, the present application provides an organic electroluminescent material comprising the organic electroluminescent composition as described above.

[0139] In another aspect, the present application provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the organic electroluminescent composition as described above.

[0140] Preferably, the organic thin film layer comprises a light-emitting layer, an optional hole-injection layer, an optional hole-transport layer, an optional electron-transport layer, 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, the hole-injection layer comprises the organic electroluminescent composition as described above.

[0141] In the present application, 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, the hole-injection layer of an organic electroluminescent device.

[0142] In one embodiment of the present application, the material of the light-emitting layer in the organic electroluminescent device comprises the organic electroluminescent composition as described above.

[0143] In one embodiment of the present application, 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 represented by formula I and formula II or the carrier capture of the light-emitting material itself.

[0144] In one embodiment of the present application, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer comprising the organic electroluminescent composition as described above, and can further comprise 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.

[0145] In another aspect, the present application provides use of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0146] Terminology

[0147] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.

[0148] As used herein, the terms "comprising" or "including" or "containing" can be open-ended, semi-closed or closed. In other words, the terms also include "consisting essentially of" or "consisting of."

[0149] Group Definitions

[0150] In this specification, groups and substituents thereof can be selected by one of ordinary skill in the art to provide stable moieties and compounds. When a substituent is described as being "selected from a group," this term is also meant to include the substituent as written as well as chemically equivalent substituents resulting from the written structure when drawn in the opposite direction as the conventional chemical formula.

[0151] The section headings used herein are for organizational purposes only and are not to be construed as limiting the subject matter described. All documents or other literary material (including, but not limited to, patents, patent applications, articles, books, treatises, and webpages) cited in this application are hereby incorporated by reference in their entirety for all purposes.

[0152] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. In case of conflict between any reference cited herein and the disclosure of the present application, the latter controls.

[0153] It should be understood that the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. In addition, the term "comprising" is to be construed as open-ended, not limiting, and is intended to cover the components "consisting essentially of" or "consisting of."

[0154] Unless otherwise indicated, the present application employs conventional methods of mass spectroscopy, elemental analysis, and follows conventional procedures of the art in the practice of the application.

[0155] Unless otherwise indicated, the present application employs standard nomenclature for analytical chemistry, organic synthesis chemistry, and optical principles. In certain instances, standard techniques are used for chemical synthesis, chemical analysis, and testing of luminescent device performance.

[0156] The compounds of the present application can contain unnatural proportions of atomic isotopes at one or more of the atoms that constitute such compounds. For example, the compounds can be labeled with radioactive isotopes, such as for example deuterium (2H). All isotopic variations of the compounds of the present application, whether radioactive or not, are encompassed within the scope of the present application.

[0157] In the present application, the number of "substituents" can be one or more, unless otherwise specified; when more than one, it means two or more, for example, 2, 3, or 4. Also, when the number of "substituents" is more than one, the "substituents" can be the same or different. In the present application, the position of "substituents", unless otherwise specified, can be any position.

[0158] In the present application, the term "alkyl", as a group or part of a group (for example, in the groups halo-substituted alkyl and the like), means a straight-chain or branched saturated aliphatic hydrocarbon group having from one to twenty carbon atoms, for example, C1-C20alkyl. For example, C1-C6alkyl as defined herein includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched arrangement. For example, in the present application, the C1-C6alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; wherein propyl is a C3alkyl group (including isomers, for example, n-propyl or isopropyl); butyl is a C4alkyl group (including isomers, for example, n-butyl, sec-butyl, isobutyl, or t-butyl); pentyl is a C5alkyl group (including isomers, for example, n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, t-pentyl, or neopentyl); and hexyl is a C6alkyl group (including isomers, for example, n-hexyl or isohexyl). 20 Alkyl includes straight chain or branched alkyl groups having from 1 to 20 carbon atoms. As defined in "C1-C6alkyl", it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched arrangement. For example, in the present application, the C1-C6alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; wherein propyl is a C3alkyl group (including isomers, for example, n-propyl or isopropyl); butyl is a C4alkyl group (including isomers, for example, n-butyl, sec-butyl, isobutyl, or t-butyl); pentyl is a C5alkyl group (including isomers, for example, n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, t-pentyl, or neopentyl); and hexyl is a C6alkyl group (including isomers, for example, n-hexyl or isohexyl).

[0159] The term "alkoxy", as used herein, refers to an alkyl group, as defined above, attached to the parent molecular moiety through an oxygen linkage (-O-).

[0160] In the present application, the term "Cn-maryl", as a group or part of a group, means a monocyclic or polycyclic aromatic group (ring atoms are only carbon atoms) having from n to m ring carbon atoms, which has at least one carbon ring having a conjugated π-electron system. Examples of the above aryl unit include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthryl. In one embodiment, the aryl group is preferably a C6-14aryl group, for example, phenyl and naphthyl, more preferably phenyl.

[0161] In the present invention, as a group or part of other groups, the term "nm-membered heteroaryl" refers to an aromatic group whose ring atoms contain one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, and whose ring atoms are n to m, and the heteroaryl is a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, wherein at least one ring is aromatic. Heteroaryl groups within the scope of this definition include, but are not limited to, acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thienyl, benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridinyl, thienopyridinyl, furopyridinyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, preferred examples of the “5- to 18-membered heteroaryl” include furanyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyrimidinyl, and carbazolyl, with carbazolyl being more preferred.

[0162] As used herein, the term Cn-Cm cycloalkyl refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as 3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicycloheptyl. In one embodiment, the C3-C10 cycloalkyl group is preferably adamantyl or cyclohexyl.

[0163] In the present invention, the limited carbon number range of the group means any integer number of carbon atoms included in the limited range, such as C1 to C 20 The number of carbon atoms in the group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20. 10 It means that the number of carbon atoms in the group can be 3, 4, 5, 6, 7, 8, 9 or 10, and the limited carbon number ranges of other groups are similar.

[0164] Without violating the common sense in the art, the above-mentioned preferred conditions can be arbitrarily combined to obtain preferred embodiments of the present invention.

[0165] The reagents and raw materials used in the present invention are commercially available.

[0166] Compared with the prior art, the present application has the following beneficial effects:

[0167] The boron-nitrogen compound of the present application realizes fine adjustment of the spectrum and further improves the light-emitting efficiency by extending the conjugation and introducing nitrogen atoms. The boron-nitrogen compound of the present application has a narrow spectrum and is used as a narrow-spectrum light-emitting material to prepare a light-emitting layer of an organic electroluminescent device, and thus the organic electroluminescent device prepared thereby realizes narrow-spectrum TADF emission, the electroluminescent spectrum is in the green-yellow light region, the half-peak width is less than 45 nm, and the highest electroluminescent external quantum efficiency of the device is as high as 30% or more. BRIEF DESCRIPTION OF DRAWINGS

[0168] Figure 1 A schematic structural diagram of a vacuum evaporation type organic electroluminescent device provided by the present application, 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.

[0169] Figure 2 A photoluminescence spectrum using compound BN-107.

[0170] Figure 3 A photoluminescence spectrum using compound BN-151. DETAILED DESCRIPTION

[0171] The technical solutions of the present application will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only used to help understand the present application and should not be regarded as specific limitations on the present application.

[0172] In the embodiments of the present application, the raw materials used for synthesizing the compounds shown are as follows:

[0173] The initial general raw materials specifically used include the following molecules:

[0174] The raw material 1 specifically used includes the following molecules:

[0175]

[0176] The raw material 2 specifically used includes the following molecules:

[0177]

[0178] The raw material 3 specifically used includes the following molecules:

[0179]

[0180] The raw material 4 specifically used includes the following molecules:

[0181]

[0182] For the synthesis of compounds represented by Formula I, the synthetic route and specific procedures are as follows:

[0183]

[0184] First, aniline raw material B j and bromobenzene raw material C k are subjected to Buchwald-Hartwig coupling reaction to obtain intermediate I-a, then another aniline raw material D l is subjected to Buchwald-Hartwig coupling reaction with 2-bromoindolo[3,2,I-jk]carbazole to obtain intermediate I-b. Subsequently, I-bromo-3-chloro-5-fluorobenzene reacts with carbazole raw material A1 to obtain I-c, I-c reacts with I-a to obtain coupling intermediate I-d, then I-d reacts with I-b to obtain precursor I-e, and finally I-e is boronized to obtain product BN.

[0185] First, aniline raw material B j and bromobenzene raw material C k , sodium tert-butoxide, tris(dibenzylideneacetone)dipalladium, and tri-tert-butylphosphine are added to 200 ml of toluene, the reaction system is stirred at 100°C under nitrogen atmosphere for 12 h, after cooling to room temperature, the reaction mixture is extracted with ethyl acetate and water, the organic phase is heated and rotary evaporated under vacuum, and then purified by column chromatography to obtain intermediate I-a.

[0186] Second, aniline raw material D l , 2-bromoindolo[3,2,I-jk]carbazole, tris(dibenzylideneacetone)dipalladium, and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine are added to 200 ml of toluene, the reaction system is stirred at 100°C under nitrogen atmosphere for 10 h, after cooling to room temperature, the reaction mixture is extracted with ethyl acetate and water, the organic phase is heated and rotary evaporated under vacuum, and then purified by column chromatography to obtain intermediate I-b.

[0187] Third, raw material 1-bromo-3-chloro-5-fluorobenzene, carbazole raw material A1, and cesium carbonate are added to 200 ml of N,N-dimethylformamide, the reaction system is stirred at 150°C for 12 hours, after cooling to room temperature, the reaction mixture is extracted with dichloromethane and water, the organic phase is heated and rotary evaporated under vacuum, and then purified by column chromatography, and the crude product is further recrystallized with dichloromethane / anhydrous methanol to obtain intermediate I-c.

[0188] Fourth step, the raw material I-c, I-a, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium, tri-tert-butylphosphonium tetrafluoroborate were added to 200 ml of toluene, the reaction system was stirred at 90 °C for 5 h under nitrogen atmosphere, after cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phase was heated and rotary evaporated under vacuum, then purified by column chromatography to obtain intermediate I-d.

[0189] Fifth step, the raw material I-d, I-b, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium, 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl were added to 200 ml of toluene, the reaction system was stirred at 100 °C for 10 h under nitrogen atmosphere, after cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phase was heated and rotary evaporated under vacuum, then purified by column chromatography to obtain precursor I-e.

[0190] Sixth step, the precursor I-e was added to 30 ml of o-dichlorobenzene, the system was replaced with nitrogen three times, then N, N-diisopropylethylamine was slowly added dropwise under ice water bath, after the dropwise addition was completed, it was stirred at 130 °C for 12 h. After cooling to room temperature, 20 ml of water was added to quench the excess boron tribromide, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and rotary evaporated under vacuum, then purified by column chromatography, and the crude product was further recrystallized with ethyl acetate / anhydrous methanol to obtain the product BN.

[0191] The synthesis of compound BN-107 is used as an example to illustrate the specific details of the synthesis example experiment:

[0192] First step, 2,4,6-trimethylaniline (6.34 g, 46.9 mmol) and 3-tert-butylbromobenzene (10.00 g, 46.9 mmol), sodium tert-butoxide (9.02 g, 93.8 mmol), tris (dibenzylideneacetone) dipalladium, tri-tert-butylphosphonium tetrafluoroborate were added to 200 ml of toluene, the reaction system was stirred at 100 °C for 12 h under nitrogen atmosphere, after cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phase was heated and rotary evaporated under vacuum, then purified by column chromatography with petroleum ether:dichloromethane = 4:1 mixed eluent to obtain a yellowish viscous oil liquid, with a yield of 58%.

[0193] In the second step, 2,4,6-trimethylaniline (1.8 g, 13 mmol), 2-bromoindolo[3,2,I-jk]carbazole (3.19 g, 10 mmol), sodium tert-butoxide (1.44 g, 15 mmol), tris(dibenzylideneacetone)dipalladium, and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine were added to 200 ml of toluene. The reaction system was stirred at 110°C for 10 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 4:1 to obtain a green solid powder with a yield of 49%.

[0194] In the third step, 1-bromo-3-chloro-5-fluorobenzene (13.51 g, 65 mmol), 3,6-di-tert-butylcarbazole (13.96 g, 50 mmol), and cesium carbonate (24.4 g, 75 mmol) were added to 200 ml of N,N-dimethylformamide, and the reaction system was stirred at 150° C. for 12 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water, and then washed with saturated brine. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 9:1. The crude product was further recrystallized from dichloromethane / anhydrous methanol to obtain a white solid with a yield of 85%.

[0195] In the fourth step, the raw materials Ic-107 (4.68 g, 9.98 mmol), Ia-107 (2.94 g, 10.98 mmol), sodium tert-butoxide (1.44 g, 14.97 mmol), tris(dibenzylideneacetone)dipalladium, and tri-tert-butylphosphine tetrafluoroborate were added to 200 ml of toluene, and the reaction system was stirred at 90 ° C. for 5 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, and the organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 6:1 to obtain a white solid with a yield of 63%.

[0196] In the fifth step, the raw materials Id-107 (3.28 g, 5 mmol), Ib-107 (2.25 g, 6 mmol), sodium tert-butoxide (0.72 g, 7.5 mmol), tris(dibenzylideneacetone)dipalladium, and 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl were added to 200 ml of toluene. The reaction system was stirred at 100°C for 10 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 9:1 to obtain a blue-green solid powder with a yield of 29%.

[0197] Step 6, precursor I-e-107 (1.00 g, 1.00 mmol) was added into 20 ml of super dry o-dichlorobenzene, the system was replaced by nitrogen for three times, then boron tribromide (1.9 mL, 20 mmol) was slowly added dropwise under ice water bath, after the dropwise addition was completed, it was stirred at 180 °C for 24 h, then N,N-diisopropylethylamine (7 mL, 40 mmol) was slowly added dropwise under ice water bath, after the dropwise addition was completed, it was stirred at 130 °C for 12 h. After cooling to room temperature, the reaction was quenched by adding 20 ml of water, then the reaction mixture was extracted with dichloromethane and water, the organic phase was dried by heating under vacuum, then it was purified by column chromatography with petroleum ether as eluent, the crude product was further recrystallized with ethyl acetate / anhydrous methanol to obtain orange solid powder BN-107 with a yield of 25%.

[0198] For the synthesis of the compound represented by Formula II, the synthetic route and specific operations are as follows:

[0199]

[0200] First, the aniline raw material B j and the bromobenzothiophene raw material C k were subjected to Buchwald-Hartwig coupling reaction to obtain intermediate II-a, then another aniline raw material D l was subjected to Buchwald-Hartwig coupling reaction with 2-bromoindolo[3,2,I-jk]carbazole to obtain intermediate II-b. Subsequently, I-bromo-3-chloro-5-fluorobenzene was reacted with the carbazole raw material A1 to obtain II-c, II-c was reacted with II-a to obtain intermediate II-d, then II-d was reacted with II-b to obtain precursor II-e, and finally I-e was boronized to obtain product BN.

[0201] First, the aniline raw material B j and the bromobenzothiophene raw material C k , sodium tert-butoxide, tris(dibenzylideneacetone)dipalladium, and tri-tert-butylphosphine were added into 200 ml of toluene, the reaction system was stirred at 100 °C under nitrogen atmosphere for 12 h, after cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phase was dried by heating under vacuum, then it was purified by column chromatography to obtain intermediate II-a.

[0202] Second, the aniline raw material D l, 2-bromoindolo[3,2,1-jk]carbazole, tris(dibenzylideneacetone)dipalladium, dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine were added to 200 ml of toluene, the reaction mixture was stirred at 100°C under nitrogen atmosphere for 10 h, after cooling to room temperature the reaction mixture was extracted with ethyl acetate and water, the organic phase was dried over sodium sulfate and concentrated under vacuum, then purified by column chromatography to obtain intermediate II-b.

[0203] In the third step, the starting material 1-bromo-3-chloro-5-fluorobenzene, the carbazole starting material A1 and cesium carbonate were added to 200 ml of N,N-dimethylformamide, the reaction mixture was stirred at 150°C for 12 h, after cooling to room temperature the reaction mixture was extracted with dichloromethane and water, the organic phase was dried over sodium sulfate and concentrated under vacuum, then purified by column chromatography, the crude product was further recrystallized from dichloromethane / absolute methanol to obtain intermediate II-c.

[0204] In the fourth step, the starting materials II-c, II-a, sodium tert-butoxide, tris(dibenzylideneacetone)dipalladium and tri-tert-butylphosphonium tetrafluoroborate were added to 200 ml of toluene, the reaction mixture was stirred at 90°C under nitrogen atmosphere for 5 h, after cooling to room temperature the reaction mixture was extracted with ethyl acetate and water, the organic phase was dried over sodium sulfate and concentrated under vacuum, then purified by column chromatography to obtain intermediate II-d.

[0205] In the fifth step, the starting materials II-d, II-b, sodium tert-butoxide, tris(dibenzylideneacetone)dipalladium and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl were added to 200 ml of toluene, the reaction mixture was stirred at 100°C under nitrogen atmosphere for 10 h, after cooling to room temperature the reaction mixture was extracted with ethyl acetate and water, the organic phase was dried over sodium sulfate and concentrated under vacuum, then purified by column chromatography to obtain precursor II-e.

[0206] In the sixth step, the precursor II-e was added to o-dichlorobenzene, the system was replaced with nitrogen three times, then N,N-diisopropylethylamine was slowly added dropwise under ice water bath, after the dropwise addition was completed, the system was stirred at 180°C under reflux for 24 h, then N,N-diisopropylethylamine was slowly added dropwise under ice water bath, after the dropwise addition was completed, the system was stirred at 130°C for 12 h. After cooling to room temperature, 20 ml of water was added to quench the excess boron tribromide, the reaction mixture was extracted with dichloromethane and water, the organic phase was dried over sodium sulfate and concentrated under vacuum, then purified by column chromatography, the crude product was further recrystallized from ethyl acetate / absolute methanol to obtain product BN.

[0207] The synthesis of compound BN-58 is used as an example to illustrate the specific details of the synthesis example experiment:

[0208] In the first step, 2,4,6-trimethylaniline (6.34 g, 46.9 mmol) and 3-bromo-5-(tert-butyl)benzo[b]thiophene (12.62 g, 46.9 mmol), sodium tert-butoxide (9.02 g, 93.8 mmol), tris(dibenzylideneacetone)dipalladium, and tri-tert-butylphosphine tetrafluoroborate were added to 200 ml of toluene. The reaction system was stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 4:1 to obtain an off-white solid with a yield of 58%.

[0209] In the second step, 2,4,6-trimethylaniline (1.8 g, 13 mmol), 2-bromoindolo[3,2,I-jk]carbazole (3.19 g, 10 mmol), sodium tert-butoxide (1.44 g, 15 mmol), tris(dibenzylideneacetone)dipalladium, and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine were added to 200 ml of toluene. The reaction system was stirred at 110°C for 10 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 4:1 to obtain a green solid powder with a yield of 49%.

[0210] In the third step, 1-bromo-3-chloro-5-fluorobenzene (13.51 g, 65 mmol), 3,6-di-tert-butylcarbazole (13.96 g, 50 mmol), and cesium carbonate (24.4 g, 75 mmol) were added to 200 ml of N,N-dimethylformamide, and the reaction system was stirred at 150° C. for 12 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water, and then washed with saturated brine. The organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 9:1. The crude product was further recrystallized from dichloromethane / anhydrous methanol to obtain a white solid with a yield of 85%.

[0211] In the fourth step, the raw materials II-c-58 (4.68 g, 9.98 mmol), II-a-58 (3.24 g, 10.98 mmol), sodium tert-butoxide (1.44 g, 14.97 mmol), tris(dibenzylideneacetone)dipalladium, and tri-tert-butylphosphine tetrafluoroborate were added to 200 ml of toluene, and the reaction system was stirred at 90 ° C. for 5 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, and the organic phase was heated under vacuum to dryness, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 6:1 to obtain a white solid with a yield of 35%.

[0212] In the fifth step, the raw materials II-d-58 (3.28 g, 5 mmol), II-b-58 (2.02 g, 6 mmol), sodium tert-butoxide (0.72 g, 7.5 mmol), tris(dibenzylideneacetone)dipalladium, and 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl were added to 200 ml of toluene, and the reaction system was stirred at 100 ° C. for 10 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and water, and the organic phase was heated under vacuum and dried, and then purified by column chromatography with a mixed eluent of petroleum ether: dichloromethane = 9:1 to obtain a blue-green solid powder with a yield of 29%.

[0213] In the sixth step, the precursor II-e-58 (1.00 g, 1.00 mmol) was added to 20 ml of ultra-dry o-dichlorobenzene, and the system was replaced with nitrogen three times. Subsequently, boron tribromide (1.9 mL, 20 mmol) was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was stirred and refluxed at 180 ° C for 24 h. Subsequently, N, N-diisopropylethylamine (7 mL, 40 mmol) was slowly added dropwise in an ice-water bath. After the addition was complete, it was stirred at 130 ° C for 12 h. After cooling to room temperature, 20 ml of water was added to quench the reaction. The reaction mixture was then extracted with dichloromethane and water. The organic phase was heated under vacuum and dried, and then purified by column chromatography with petroleum ether as the eluent. The crude product was further recrystallized from ethyl acetate / anhydrous methanol to obtain an orange solid powder BN-58 with a yield of 23%.

[0214] The product was characterized using a VarioM1cro Cube from Ag1lent, USA, for elemental analysis, and the tested elements were C, H, N, and S. The mass spectrometry was performed using a Thermo Fisher TSQEndura ultra-high performance liquid chromatography coupled to a triple quadrupole mass spectrometer from USA.

[0215] The results of the photoluminescence test of the compounds showed that: taking compound BN-17 as an example, the compound was in a toluene solution (1×10 -5 The emission peak in M ​​is 519 nm and the half-peak width is 20 nm ( Figure 2 ), the photoluminescence spectrum of BN-151 shows that its emission peak is 520 nm and the half-peak width is 21 nm ( Figure 3 ).

[0216] Table 1. Summary of product data of synthetic examples

[0217]

[0218]

[0219] Electroluminescent device embodiments

[0220] Some representative electroluminescent device embodiments are given below, and the molecular structures of some materials involved in the device embodiments and comparative embodiments are as follows:

[0221]

[0222]

[0223] The following is an embodiment of an electroluminescent device prepared using the material of the present application, and the specific device preparation process is as follows:

[0224] Organic electroluminescent device preparation process:

[0225] The results of the device are 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.

[0226] The preparation process is as follows:

[0227] (1) Substrate treatment: transparent ITO glass is used as the substrate material for device preparation, and is first treated with 5% ITO washing solution for 30 min, then sequentially washed with distilled water (2 times), acetone (2 times), and isopropyl alcohol (2 times), and finally stored in isopropyl alcohol. Before each use, the surface of the ITO glass is carefully wiped with an acetone cotton ball and an isopropyl alcohol cotton ball, then rinsed with isopropyl alcohol and dried, and then treated with plasma for 5 min for standby. The device is prepared using a combination of spin coating and vacuum evaporation process.

[0228] (2) Hole injection layer and hole transport layer preparation: the hole transport layer is prepared using an evaporation process, and evaporation is started when the vacuum degree of the vacuum evaporation system reaches 5 x 10 -4 Pa, and the deposition rate is measured by a Syms film thickness meter. The organic hole transport layer is sequentially deposited on the surface of the ITO electrode using a vacuum evaporation process, and the deposition rate of the hole transport material is

[0229] (3) Light-emitting layer preparation: the light-emitting layer is prepared using an evaporation process, and evaporation is started when the vacuum degree of the vacuum evaporation system reaches 5 x 10 - 4 Pa, and the deposition rate is measured by a Syms film thickness meter. The light-emitting layer is sequentially deposited on the hole transport layer using a vacuum evaporation process, and the deposition rate of the light-emitting layer material is

[0230] (4) Electron transport layer, electron injection layer and metal electrode preparation: the electron transport layer, electron injection layer and metal electrode are prepared using an evaporation process, and evaporation is started when the vacuum degree of the vacuum evaporation system reaches 5 x 10 -4When the thickness is below Pa, the deposition begins, and the deposition rate is measured by a film thickness meter. The organic electron transport layer, the LiF electron injection layer, and the metal Al electrode are sequentially deposited on the light-emitting layer using a vacuum deposition process (see the following embodiment for the specific device structure). The deposition rate of the organic material is The deposition rate of LiF is The deposition rate of Al is Device Example 1-n (n=31)

[0231] In the device examples 1-n (n=1-31), the organic electroluminescent devices (structures such as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-33 is used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-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 / 15wt% HIM+85wt% HTL-1 (100nm) / HTL-2 (10nm) / 99wt% H1-33+1wt% BN-m (30nm) / TRZ-77 (10nm) / ETL-1 (30nm)LiF (1nm) / Al (100nm)].

[0232] The performance data of the device embodiment are shown in Table 2. The current, voltage, brightness, luminescence spectrum and other characteristics of the device are tested synchronously using a Photo Research PR 655 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system. The performance test of the device is carried out at room temperature and ambient atmosphere. The external quantum efficiency (EQE) of the device is calculated by combining the current density, brightness and electroluminescence spectrum with the visibility function under the condition of Lambertian distribution of luminescence (the same below). The device life (T95, hours) in Table 2 refers to the device with an initial brightness of 1000 cd / m 2 When the brightness of the device drops to 95% of the initial brightness (i.e. the brightness of the device drops to 950cd / m 2 The time required for

[0233] Comparative device examples D1-n (n=1-7)

[0234] In the comparative device examples 1-n (n=1-7), the organic electroluminescent devices (structures such as Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-33 is used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the comparative device example) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-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 of the effect example is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 99 wt% H1-33 + 1 wt% Rm (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0235] The performance data of the comparative device embodiment are shown in Table D2. The device life (T95, hours) in Table D2 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 95% of the initial brightness (i.e. the brightness of the device drops to 950cd / m 2 The time required for

[0236] Table 2

[0237]

[0238]

[0239] Table D2

[0240]

[0241] Device Example 2-n (n=1-31)

[0242] In the device examples 2-n (n=1-31), the organic electroluminescent device (structure as shown in FIG. Figure 1(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-33 + TRZ-83 are used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 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 of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-33 + 29 wt% TRZ-83 + 1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0243] The performance data of the device embodiment are shown in Table 3. The device life (T95, hours) in Table 3 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 95% of the initial brightness (i.e. the brightness of the device drops to 950cd / m 2 The time required for

[0244] Comparative device example D2-n (n=1-3)

[0245] In the comparative device examples 2-n (n=1-3), the organic electroluminescent devices (structures such as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-33 + TRZ-83 are used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 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 of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-33 + 29 wt% TRZ-83 + 1 wt% Rm (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)]. This device structure is only suitable for three contrasting luminescent materials: R-5, R-6 and R-7.

[0246] The performance data of the comparative device embodiment are shown in Table D3. The device life (T95, hours) in Table D3 refers to the device initial brightness of 1000 cd / m2 the time required for the luminance of the device to decrease to 95% of the initial luminance (i.e. the time required for the luminance of the device to decrease to 950 cd / m 2 .

[0247] Table 3

[0248]

[0249]

[0250] Table D3

[0251]

[0252] Device Examples 3-n (n = 1-31)

[0253] In the organic electroluminescent devices (structures as shown in Figure 1 HIM-doped HTL-1 was used as the first hole transport layer, HTL-2 was used as the second hole transport layer, H1-223+2CN-13 was used as the host material in the light-emitting layer, BN-m (m represents the last number of the code of the light-emitting material used in the device example) was used as the doped light-emitting material (doping concentration was 1 wt%), TRZ-77 was used as the second electron transport layer, ETL-1 was used as the first electron transport layer, LiF was used as the electron injection layer, and Al was used as the metal cathode. The structure of the organic electroluminescent device of the effect example was [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-223+29 wt% 2CN-13+1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) / LiF (1 nm) / Al (100 nm)].

[0254] The performance data of the device examples are shown in Table 4. In Table 4, the device lifetime (T95, hours) refers to the time required for the luminance of the device to decrease to 95% of the initial luminance (i.e. the time required for the luminance of the device to decrease to 950 cd / m 2 , when the luminance of the device decreased to 95% of the initial luminance (i.e. when the luminance of the device decreased to 950 cd / m 2 .

[0255] Comparative Device Examples 3-n (n = 1-3)

[0256] In the organic electroluminescent devices (structures as shown in Figure 1HIM-doped HTL-1 as the first hole transport layer, HTL-2 as the second hole transport layer, H1-223+2CN"13 as the host material in the light-emitting layer, R-m (m represents the last number of the code of the light-emitting material used in the device example) as the doped light-emitting material (the doping concentration is 1 wt%), TRZ-77 as the second electron transport layer, ETL-1 as the first electron transport layer, LiF as the electron injection layer, and Al as the metal cathode. The structure of the organic electroluminescent device of the effect example is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 70 wt% H1-223+29 wt% 2CN"13+1 wt% R-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) / LiF (1 nm) / Al (100 nm)]. This device structure is only suitable for three comparative light-emitting materials R-5, R-6 and R-7.

[0257] The performance data of the device examples are shown in Table D4. In Table D4, the device lifetime (T95, hours) refers to the time required for the luminance of the device to decrease to 95% of the initial luminance (i.e., the luminance of the device to decrease to 950 cd / m 2 . 2

[0258] Table 4

[0259]

[0260]

[0261] Table D4

[0262]

[0263] Device example 4-n (n = 1-31)

[0264] The organic electroluminescent devices in device examples 1-n (n = 1-31) (the structure is as shown in Table 1) were prepared according to the following steps: Figure 1 ​(as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-223 + IrPPy are used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-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 of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-223 + 9 wt% IrPPy + 1 wt% BN-m (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)].

[0265] The performance data of the device embodiment are shown in Table 5. The device life (T95, hours) in Table 5 refers to the device initial brightness of 1000 cd / m 2 When the brightness of the device drops to 95% of the initial brightness (i.e. the brightness of the device drops to 900cd / m 2 The time required for

[0266] Comparative device example 4-n (n=1-3)

[0267] In the device examples 1-n (n=1-3), the organic electroluminescent devices (structures such as Figure 1 (as shown), HTL-1 doped with HIM is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-223 + IrPPy are used as the host material in the light-emitting layer, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1 wt%), TRZ-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 of the effect embodiment is [ITO / 15 wt% HIM + 85 wt% HTL-1 (100 nm) / HTL-2 (10 nm) / 90 wt% H1-223 + 9 wt% IrPPy + 1 wt% Rm (30 nm) / TRZ-77 (10 nm) / ETL-1 (30 nm) LiF (1 nm) / Al (100 nm)]. This device structure is only suitable for three contrasting luminescent materials: R-5, R-6 and R-7.

[0268] The performance data of the device embodiment are shown in Table D5. The device life (T95, hours) in Table D5 refers to the device initial brightness of 1000 cd / m2 the time required when the luminance of the device decreases to 95% of the initial luminance (i.e. when the luminance of the device decreases to 950 cd / m 2 .

[0269] Table 5

[0270]

[0271]

[0272] Table D5

[0273]

[0274] Applicants state that the boron-nitrogen compounds of the present application and the use thereof are illustrated by the above examples, but the present application is not limited to the above examples, i.e. it is not meant that the present application must rely on the above examples to be implemented. It should be apparent to those skilled in the art that any improvement to the present application, equivalent replacement of the raw materials selected by the present application, addition of auxiliary ingredients, selection of specific modes, etc. all fall within the scope of protection and disclosure of the present application.

Claims

1. A boron-nitrogen compound, characterized in that: The boron nitrogen compound has the structure shown in the following formula I and formula II: R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, one or more R a Substituted C6-C18 aryl, 5- to 18-membered heteroaryl, substituted by one or more R a substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R a substituted diphenylamino groups; R a Each occurrence is independently deuterium, fluorine, CN, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 12 Cycloalkyl, C6~C 14 Aryl, one or more R b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R b substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R b substituted diphenylamino groups; R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R c substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R c substituted diphenylamino groups; R c Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, substituted by one or more R d substituted 5- to 18-membered heteroaryl, diphenylamino, or one or more R d substituted diphenylamino groups; R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or replaced by one or more R e Substituted C6-C14 aryl; R e Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 1 and R 2 Exist independently or R 1 and R 2 At least one of them forms a ring with the connected aromatic ring; R 3 and R 4 Exist independently or R 3 and R 4 At least one of them forms a ring with the connected aromatic ring; R 5 、R 6 and R 7 Exist independently or R 5 、R 6 and R 7 At least one of them forms a ring with the connected aromatic ring; R 8 、R 9 and R 10 Exist independently or R 8 、R 9 and R 10 At least one of them forms a ring with the connected aromatic ring; R 11 、R 12 、R 13 、R 14 、R 15 、R 21 、R 22 、R 23 、R 24 、R 25 、R 31 、R 32 、R 33 、R 34 、R 41 、R 42 、R 43 and R 44 independently selected from H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl or one or more R f Substituted C6-C18 aryl; R f Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C18 aryl, or replaced by one or more R g Substituted C6-C18 aryl; R g Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 11 、R 12 、R 13 、R 14 and R 15 Exist independently or R 11 、R 12 、R 13 、R 14 and R 15 At least one of them forms a ring with the connected aromatic ring; R 21 、R 22 、R 23 、R 24 and R 25 Exist independently or R 21 、R 22 、R 23 、R 24 and R 25 At least one of them forms a ring with the connected aromatic ring; R 31 、R 32 、R 33 and R 34 Exist independently or R 31 、R 32 、R 33 and R 34 At least one of them forms a ring with the connected aromatic ring; R 41 、R 42 、R 43 and R 44 Exist independently or R 41 、R 42 、R 43 and R 44 At least one of them forms a ring with the connected aromatic ring; X is S, O or Se; The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl groups.

2. The boron nitrogen compound according to claim 1, characterized in that The R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, deuterium, C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl, C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R a Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R b Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R c Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, at least one C1-C 12 Alkyl-substituted diphenylamine, carbazole, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R d Each occurrence is independently deuterium, fluorine, C1~C 12 Alkyl, C1~C 12 Alkoxy, C3-C 10 Cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, at least one C1-C 12 Alkoxy-substituted phenyl, carbazolyl, at least one C1-C 12 Alkyl-substituted carbazolyl; Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexyloxy, Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl, The wavy lines represent the attachment sites of the groups; Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, methyl, 2-methyl-phenyl, Phenyl, The wavy lines represent the attachment sites of the groups; Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H, methyl, 2-methyl-phenyl, Phenyl, Any of the following; Preferably, the R 1 、R 2 、R 3 and R 4 are independently H, methyl, 2-methyl-phenyl, Phenyl, Any one of R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H or deuterium; Preferably, the R 1 and R 4 are independently H or deuterium, R 2 and R 3 Same, H, methyl, 2-methyl-phenyl Phenyl, Any one of R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently H or deuterium; Preferably, the R 11 、R 12 、R 13 、R 14 、R 15 、R 21 、R 22 、R 23 、R 24 、R 25 、R 31 、R 32 、R 33 、R 34 、R 34 、R 42 、R 43 and R 44 independently selected from H, deuterium, C1-C4 alkyl or C6-C12 aryl; Preferably, R 11 、R 12 、R 13 、R 14 、R 15 、R 21 、R 22 、R 23 、R 24 、R 25 、R 31 、R 32 、R 33 、R 34 、R 34 、R 42 、R 43 and R 44 Independently selected from H, methyl, or phenyl; Preferably, R 11 、R 12 、R 13 、R 14 、R 15 、R 21 、R 22 、R 23 、R 24 、R 25 、R 31 、R 32 、R 33 、R 34 、R 34 、R 42 、R 43 and R 44 At least one of them is connected to the aromatic ring to form the following ring structure: The bond with * is the bond shared with the aromatic ring; Preferably, X is S.

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

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

5. The organic electroluminescent composition according to claim 4, characterized in that The host material is a compound having a structure as shown in any one of formulas (H-1) to (H-10): wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N; where R 1H and R 2H Independently any of the following groups: wherein X1, Y1 and Z1 are CH or N, and at most one of X1, Y1 and Z1 is N; where R aH and R bH are independently H, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or C1-C 20 Alkoxy-substituted C6-C 20 Aryl, * represents the attachment site of the group; W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 independently S or O; R 3H 、R 4H 、R 5H 、R 6H 、R 7H 、R 8H 、R 9H 、R 10H 、R 11H 、R 12H 、R 13H and R 14H are independently H, deuterium, C1-C6 alkyl or C6-C24 aryl; Preferably, the organic electroluminescent composition contains 0.3-30.0 wt% of the boron nitrogen compound according to any one of claims 1-3 as a dopant material, and the remaining 99.7-70.0 wt% of the components are a host material composed of 1-2 compounds having structures of formula (H-1) to formula (H-10); Preferably, the host material contains two compounds having structures of formula (H-1) to formula (H-10), and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains 0.3-30.0 wt% of the boron nitrogen compound according to any one of claims 1 to 3, and the remaining 99.7-70.0 wt% of the components are one or two compounds selected from compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains two compounds selected from compounds H1-1 to H1-254 as host materials, and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds according to any one of claims 1 to 3; the host material is composed of any one of the compounds represented by formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds having the structures represented by formulas H-1 to H-10; where R 1a 、R 1b 、R 2a 、R 2b 、R 3a and R 3b One or two of them are independently R Tz , the rest are the same or different and are independently hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 C6-C8 substituted aryl or C1-C8 alkoxy 18 Aryl; R Tz is any one of the substituent groups shown below: The asterisk represents the attachment site of the group; Preferably, the amount ratio between the compound represented by Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compound represented by H-1, H-2, H-3, H-4, H-5H-6, H-7, H-8, H9 or H-10 in the host material is 1:20 to 20:1; Preferably, the weight ratio of the compound represented by formulae TRZ-1 to TRZ-86 to the carbazole or carboline derivative represented by any one of formulae (H-1) to (H-10) in the host material is 1:20 to 20:1; Preferably, the weight ratio between the compounds represented by formulas TRZ-1 to TRZ-86 and the compounds H1-1 to H1-254 in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the compounds of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds represented by formulas H-1 to H-10; in the host material, the weight ratio between the Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compound and the compound represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by Formula I and Formula II; the host material is composed of any one of the 1,3,5-triazine derivatives represented by Formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by Formulas H1-1 to H1-254; in the host material, the weight ratio of the 1,3,5-triazine derivative to the carbazole or carboline derivative is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-155; the host material is composed of any one of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254; in the host material, the weight ratio of the compounds represented by formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A and Trz6-A to the carbazole or carboline derivatives represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-155; the host material is composed of any one of the 1,3,5-triazine derivatives represented by formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives represented by formulas H1-1 to H1-254; in the host material, the weight ratio between the 1,3,5-triazine derivative represented by formulas TRZ-1 to TRZ-86 and the carbazole or carboline derivative represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, in the organic electroluminescent composition, the host material is composed of any one of the compounds having the structures represented by formulae H-1 to H-10 and any one of the compounds represented by formulae Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6; Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur); R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl; R si (i=7-39) are independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl; Preferably, R s1 、R s2 、R s3 、R s4 、R s5 and R s6 Independently selected from any of the following 24 groups: Asterisks represent the attachment sites of the groups; Preferably, R si (i=7-39) are independently selected from any one of the following five groups: *-H *-D *-CH3 Asterisks represent the attachment sites of the groups; Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds according to any one of claims 1 to 3, and the host material is composed of any one of the compounds represented by formulae 2CN-1 to 2CN-60 and any one of the compounds represented by formulae H1-1 to H1-254; Preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the compounds of formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds represented by formulas H-1 to H-10; preferably, in the host material, the weight ratio between the compounds of Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and the compounds represented by H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron-nitrogen compound according to any one of claims 1 to 3; the host material is composed of any one of the dicyanobenzene derivatives represented by formulae 2CN-1 to 2CN-60 and any one of the carbazole derivatives represented by formulae H1-1 to H1-254; preferably, in the host material, the weight ratio of the dicyanobenzene derivative to the carbazole derivative is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-155, and the host material is composed of any one of the compounds represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds represented by formulas H1-1 to H1-254; preferably, in the host material, the weight ratio between the compound represented by formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and the compound represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the dopant material in the organic electroluminescent composition is any one of the compounds represented by formulas BN-1 to BN-155, and the host material is composed of any one of the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and any one of the compounds represented by formulas H1-1 to H1-254; preferably, in the host material, the weight ratio between the dicyanobenzene derivatives represented by formulas 2CN-1 to 2CN-60 and the carbazole derivatives represented by formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds described in claims 1-3, and the main material is composed of any one of the compounds represented by formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir or Pt represented by formulas Ir-1, Ir-2 and Pt-; preferably, in the main material, the weight ratio between the compounds represented by formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is 1:20 to 20:

1. R ri are independently hydrogen, deuterium, C1-C18 alkyl, or C6-C18 aryl, wherein i is an integer from 1 to 22, and wherein the dashed line represents that two of the four bonds included are double bonds; R ri Any of the groups can form a ring with the aromatic ring or aromatic heterocycle to which it is connected; Preferably, the phosphorescent compound containing metal Ir or Pt is any one of the following compounds: Preferably, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formulas BN-1 to BN-155, and the main material is composed of any one of the carbazole or carbidine derivatives shown in formulas H1-1 to H1-254 and the phosphorescent compounds containing metal Ir shown in formulas Ir-1 and Ir-2. Preferably, in the main material, the weight ratio between the carbazole or carbidine derivatives shown in formulas H1-1 to H1-254 and the phosphorescent compounds containing metal Ir is 1:20 to 20:

1.

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

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

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

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

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