Boron-nitrogen compound and application thereof

Abstract

The invention provides a boron-nitrogen compound and application thereof, the boron-nitrogen compound has a structure as shown in a formula I or a formula II, and the boron-nitrogen compound not only realizes fine adjustment of a spectrum but also further improves luminous efficiency through extension conjugation and introduction of nitrogen atoms. The boron-nitrogen compound provided by the invention has a narrow spectrum, the organic electroluminescent device prepared from the boron-nitrogen compound realizes narrow-spectrum TADF emission, the electroluminescent spectrum is in a green-yellow light region, the half-peak width is less than 45nm, and the highest electroluminescent external quantum efficiency of the device is up to 34% or above.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescence, and relates to a boron-nitrogen compound and application thereof. BACKGROUND

[0002] Organic optoelectronic materials are a class of organic materials with the characteristics of generation, conversion and transmission of photons and electrons. At present, the controllable photoelectric performance of organic optoelectronic materials has been applied to organic light-emitting diodes (OLED), organic photovoltaic cells (OPV), organic field effect transistors (OFET), and even organic lasers. In recent years, OLED has become a very popular new type of flat panel display product at home and abroad. OLED display has the characteristics of self-emission, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low working voltage, thin panel, large size flexible panel, and low cost, and is known as the star flat panel display product in the 21st century.

[0003] The history of organic electroluminescence can be traced back to the report of Bernanose et al. in 1953 (Holst G A, Kster T, Voges E, et al. FLOX—an oxygen-flux-measuring system using a phase-modulation method to evaluate the oxygen-dependent fluorescence lifetime, ScienceDirect. Sensors and Actuators B: Chemical, 1995, 29, 213.), about 10 years later, in 1963, Pope et al. of New York University applied voltage on the crystal of anthracene, and the fluorescence emission of anthracene could be observed (M. Pope, H. Kallmann and P. Magnante, Electroluminescence in Organic Crystals, J. Chem. Phys., 1963, 38, 2042). In 1987, C. W. Tang et al. of Kodak Company in the United States used super-thin film technology to prepare a light-emitting device, using aromatic amine with good hole transport effect as a hole transport layer, and 8-hydroxyquinoline aluminum complex as a light-emitting layer, and indium tin oxide (ITO) thin film and metal alloy as anode and cathode respectively. The device obtained a brightness of 1000 cd / m2 at a driving voltage of 10 V.2 The breakthrough of the green light emission with an efficiency of 1.5 lm / W (C. W. Tang and S. A. Van Slyke, Organic electroluminescent diodes, Appl. Phys. Lett., 1987, 51, 913) made the research of organic electroluminescence develop rapidly and deeply in the world. In 1990, Burroughes et al. from Cambridge University proposed the first light-emitting diode based on polymer (PPV), which showed that PPV could be used as a highly fluorescent emission material in a single-layer device with high luminous efficiency (Burroughes J. H. 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 electrophosphorescent device, which could theoretically have an internal quantum efficiency of 100% (M. A. Baldo, D. F. O'Brien et al., Highly efficient phosphorescent emission from organic electroluminescent devices, Nature, 1998, 395, 151). However, on the one hand, phosphorescent materials generally use expensive noble metals such as iridium and platinum, and on the other hand, the chemical instability of deep blue phosphorescent materials and the large efficiency roll-off of the device under high current density still exist. Therefore, it is extremely important to develop an OLED device using cheap and stable organic small molecule materials while achieving high-efficiency light emission.

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

[0005] TADF molecules are mainly doped as guest materials in wide band gap host materials to achieve high efficiency of 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, and thus is easily affected by the intermolecular vibration and rotation, resulting in a wide emission spectrum and a 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 eliminate 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, the main problem faced by organic TADF light-emitting materials is solved. 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 layers of organic electroluminescent devices, so that the organic electroluminescent devices show excellent characteristics.

[0007] 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 or formula II:

[0009]

[0010] Y1, Y2, Y3and Y4are independently C-H, C-R 13 , C-R 14 or N;

[0011] Y5, Y6, Y7and Y8are independently C-H, C-R 11 , C-R 12 or N;

[0012] R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 1 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently selected from H, deuterium, C1-C20alkyl, C1-C20alkoxy, C3-C10cycloalkyl, C6-C18aryl, C6-C18aryl substituted by one or more R a , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R a , diphenylamino, or diphenylamino substituted by one or more R a ;

[0013] R a is independently at each occurrence deuterium, fluorine, CN, C1-C12alkyl, C1-C12alkoxy, C3-C12cycloalkyl, C6-C14aryl, C6-C14aryl substituted by one or more R b , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R b , diphenylamino, or diphenylamino substituted by one or more R b ;

[0014] R b is independently at each occurrence deuterium, fluorine, CN, C1-C12alkyl, C1-C12alkoxy, C3-C10cycloalkyl, C6-C14aryl, C6-C14aryl substituted by one or more R c , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R c , diphenylamino, or diphenylamino substituted by one or more R c ;

[0015] R c independently for each occurrence deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R d substituted C6-C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted with one or more R d substituted 5- to 18-membered heteroaryl, diphenylamino, or diphenylamino substituted with one or more R d substituted diphenylamino;

[0016] R d independently for each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or C6-C14 aryl substituted with one or more R e substituted C6-C14 aryl;

[0017] R e independently for each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl;

[0018] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are independently present or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 at least one of R

[0019] said alkyl, alkoxy, cycloalkyl, aryl, heteroaryl 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.

[0020] In some embodiments of the application, said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 1 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently H, D (deuterium), C1-C12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 10 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl.

[0021] Preferably, said R a are independently at each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 10 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl.

[0022] Preferably, said R b are independently at each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 10 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12 alkyl, C1-C12 haloalkyl, C3-C10 cycloalkyl, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl. 12Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group.

[0023] Preferably, the R c Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group.

[0024] Preferably, the R d Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, carbazole, or alkyl-substituted phenyl groups with at least one C1-C bond 12 Alkyl-substituted carbazole group.

[0025] Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independently, H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexoxy Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl

[0026]

[0027] wherein the wavy line represents the point of attachment of the group;

[0028] Preferably, said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 1 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently H, methyl, 2-methyl-phenyl, phenyl,

[0029] wherein the wavy line represents the point of attachment of the group.

[0030] Preferably, R is selected from H, D, phenyl, biphenyl, C1-C10 alkyl substituted phenyl, C6-C12 aryl substituted biphenyl, C5-C20 nitrogen containing heteroaryl, C6-C12 aryl substituted C5-C20 nitrogen containing heteroaryl.

[0031] Further preferably, said R is selected from H, D or phenyl.

[0032] In some embodiments of the application, said boron-nitrogen compound is any one of the following compounds:

[0033]

[0034]

[0035]

[0036]

[0037] In another aspect, the present application provides an organic electroluminescent material comprising a boron-nitrogen compound as described above.

[0038] 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 at least one of the boron-nitrogen compounds as described above.

[0039] Preferably, the organic thin film layer comprises a light-emitting layer, optionally a hole-injection layer, optionally a hole-transport layer, optionally an electron-transport layer, and optionally an 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 at least one of the boron-nitrogen compounds as described above.

[0040] In the present application, the boron-nitrogen compounds having the structures of Formula I and Formula II can be used as functional materials 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 the organic electroluminescent device.

[0041] 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.

[0042] In one embodiment, the organic electroluminescent device has a structure as shown in Figure 1 wherein 1 is an ITO anode, 2 is a first hole-transport layer, 3 is a second hole-transport layer, 4 is a light-emitting layer, 5 is a second electron-transport layer, 6 is a first electron-transport layer, 7 is an electron-injection layer, and 8 is a metal cathode.

[0043] In one embodiment, the boron-nitrogen compounds having the structures of Formula I and Formula II are used to prepare a light-emitting layer in an organic electroluminescent device.

[0044] In one embodiment, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer formed in sequence on the substrate; the organic light-emitting functional layer comprises a light-emitting layer comprising the boron-nitrogen compound 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.

[0045] In another aspect, the present application provides an organic electroluminescent composition comprising a boron-nitrogen compound as described above as a dopant material and a host material;

[0046] Preferably, the host material is a material having an electron-transporting ability and / or a hole-transporting ability and having a triplet excited state energy equal to or higher than that of the dopant material.

[0047] In certain embodiments of the present application, the host material is a carbazole derivative and / or a carbolin derivative having a structure according to any one of formulae (H-1) to (H-10):

[0048]

[0049] wherein X1, Y1and Z1are CH or N, and at most one of X1, Y1and Z1is N; wherein R 1H and R 2H are independently any one of the following groups:

[0050]

[0051]

[0052] wherein X2, Y2and Z2are CH or N, and at most one of X2, Y2and Z2is N;

[0053] wherein R aH and R bH are independently H, C1-C 20 alkyl, C1-C 20 alkoxy, C6-C 20 aryl, C1-C 20 alkyl-substituted C6-C 20 aryl, or C1-C 20 alkoxy-substituted C6-C 20 aryl, the asterisk denoting the site of attachment of the group;

[0054] W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , W 7 , W 8 and W 9 are independently S or O;

[0055] 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-C6alkyl or C6-C24aryl.

[0056] In one embodiment of the present application, the organic electroluminescent composition contains 0.3 to 30.0 wt% (for example, 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 as described above as a dopant material, 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 are host materials composed of 1 to 2 compounds having the structures of Formulas (H-1) to (H-10).

[0057] In one embodiment of the present application, the host material contains 2 compounds having the structures of Formulas (H-1) to (H-10), and the weight ratio of the two compounds is 1:5 to 5:1, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0058] Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] 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 are one or two compounds selected from the group consisting of Compounds H1-1 to H1-254.

[0071] 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.

[0072] In one embodiment of the present application, the dopant material in the organic electroluminescent composition is any one of the boron-nitrogen compounds having the structure of Formula I and Formula II (0.3 to 30.0 wt%), and the host material (99.7 to 70.0 wt%) is composed of any one of the compounds having the structure of Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A and any one of the compounds having the structure of Formula H-1 to H-10.

[0073] In one preferred embodiment, the amount ratio between the compound of Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A and the compound of 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, and the like.

[0074]

[0075] wherein R 1a , R 1b , R 2a , R 2b , R3a and 1 or 2 of R 3b independently R Tz , the others being identical or different, 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 substituents:

[0076]

[0077]

[0078] wherein the asterisk denotes the site of attachment of the group;

[0079] In a preferred embodiment, the weight ratio between the compound of formula TRZ-1 to TRZ-86 and the carbazole or carboline derivative of any one of formula (H-1) to formula (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.

[0080] In a preferred embodiment, the organic electroluminescent composition is an emission layer; the dopant material in the organic electroluminescent composition is any one of the compounds of formula I and formula II (in an amount of 0.3 wt-30.0 wt%); the host material (in an amount of 99.7 wt-70.0 wt%) consists 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 of 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 of 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.

[0081] 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 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 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.

[0082] 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 Formula BN-1 to BN-48 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of the compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of the carbazole or carboline derivatives represented by Formula H1-1 to H1-254. For example, in the host material, the weight ratio between the compounds represented by Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carboline derivatives represented by Formula H1-1 to H1-254 is 1:20 to 20:1, 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.

[0083] 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-48 (content: 0.3 wt% - 30.0 wt%); the host material (content: 99.7 wt% - 70.0 wt%) is composed of any one of the 1,3,5-triazine derivatives represented by 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, in the host material, the weight ratio between the 1,3,5-triazine derivative represented by formulae TRZ-1 to TRZ-86 and the carbazole or carboline derivative represented by formulae H1-1 to H1-254 is 1:20 to 20:1, for example, 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0084]

[0085]

[0086]

[0087]

[0088] In the present application, the host material in the organic electroluminescence composition is composed of any one of the compounds 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.

[0089]

[0090]

[0091] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur);

[0092] R s1 , R s2 , R s3 , R s4 , R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl;

[0093] R si(i = 7-39) are independently H, deuterium, C1-C6alkyl, C1-C6alkoxy, or C6-C24aryl;

[0094] 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:

[0095]

[0096] The asterisk represents the point of attachment of the group.

[0097] Preferably, R si (i = 7-39) are independently selected from any one of the following 5 groups:

[0098] * -H -D * -CH3 The asterisk represents the point of attachment of the group.

[0099] Preferably, 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 as described above, and the host material is composed of any one of the compounds of Formula 2CN-1 to 2CN-60 and any one of the compounds of Formula H1-1 to H1-254;

[0100]

[0101]

[0102]

[0103] In an 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 of Formula (H-1) to Formula (H-10). In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any one of the compounds of Formula I and Formula II, and the remaining 99.7-70.0 wt% of the composition is a host composed of 1-2 compounds having the structures of Formula (H-1) to Formula (H-10). For example, when the host contains 2 compounds having the structures of Formula (H-1) to Formula (H-10), the weight ratio of the two compounds is 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0104] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the main material in the composition is one or two compounds selected from H1-1 to H1-254. In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any compound represented by Formula I, and the remaining 99.7-70.0 wt% is one or two compounds selected from H1-1 to H1-254. For example, when the composition contains two compounds selected from H1-1 to H1-254, the weight ratio of the two compounds is 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0105] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the compounds shown in Formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds shown in Formulas H-1 to H-10. For example, in the host material, the weight ratio between the Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compound and the compound shown in H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0106] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in Formula TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives shown in Formula H1-1 to H1-254. For example, in the main material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0107] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-48 (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the compounds shown in formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of the carbazole or carboline derivatives shown in formula H1-1 to H1-254. For example, in the main material, the weight ratio between compounds of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and carbazole or carbline derivatives of formulas H1-1 to H1-254 is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1.

[0108] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the compounds of Formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds shown in Formulas H-1 to H-10. For example, in the host material, the weight ratio between the compounds Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5, or Ph-2CN-6 and the compounds H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9, or H-10 is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0109] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the dicyanobenzene derivatives shown in Formula 2CN-1 to 2CN-60 and any one of the carbazole or carboline derivatives shown in Formula H1-1 to H1-254. For example, in the main material, the weight ratio between the dicyanbenzene derivative and the carbazole or carboline derivative is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0110] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-48 (content of 0.3wt-30.0wt%); the host material (content of 99.7wt-70.0wt%) is composed of any one of the compounds of formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-254. For example, in the host material, the weight ratio between the compound of 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 derivatives shown in formulas H1-1 to H1-254 is 1:20 to 20:1.

[0111] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-48 (content of 0.3wt-30.0wt%), and the host material (content of 99.7wt-70.0wt%) is composed of any one of the dicyanobenzene derivatives shown in formula 2CN-1 to 2CN-60 and any one of the carbazole or carboline derivatives shown in formula H1-1 to H1-254. For example, in the main material, the weight ratio between the dicyanobenzene derivatives shown in formulas 2CN-1 to 2CN-60 and the carbazole or carbline derivatives shown in formulas H1-1 to H1-254 is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0112] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content of 0.3wt-30.0wt%), and the host material (content of 99.7wt-70.0wt%) is composed of any one of the carbazole or carboline derivatives shown in Formulas H1-1 to H1-254 and a phosphorescent compound containing metal Ir or Pt shown in Formulas Ir-1, Ir-2 and Pt-1. For example, in the main material, the weight ratio between carbazole or carbline derivatives as shown in formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is 1:20 to 20:1, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1 or 20:1, etc.

[0113]

[0114] R ri Independently hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, where i is an integer from 1 to 22, and the dashed line represents two double bonds that are separated by two of the four bonds contained.

[0115] R ri Any one of the groups can form a ring with the aromatic ring or aromatic heterocycle attached to it;

[0116] Preferably, the phosphorescent compound containing metallic Ir is any one of the following compounds:

[0117]

[0118]

[0119] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the compounds shown in formulas BN-1 to BN-48 (content of 0.3wt-30.0wt%), and the host material (content of 99.7wt-70.0wt%) is composed of any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-254 and a phosphorescent compound containing metallic Ir shown in formulas Ir-1 and Ir-2. For example, in the host material, the weight ratio between the carbazole or carboline derivatives shown in formulas H1-1 to H1-254 and the phosphorescent compound containing metallic Ir is 1:20 to 20:1.

[0120] On the other hand, the present invention provides an organic electroluminescent material comprising the organic electroluminescent composition as described above.

[0121] On the other hand, the present invention 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 organic electroluminescent composition as described above.

[0122] Preferably, the organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, and an optional electron injection layer, wherein at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer comprises the organic electroluminescent composition as described above.

[0123] In this invention, the organic electroluminescent composition can be used as a functional material in at least one of the following layers of an organic electroluminescent device: the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer.

[0124] In one embodiment of the present invention, the material of the light-emitting layer in the organic electroluminescent device comprises the organic electroluminescent composition as described above.

[0125] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on energy transfer from the host material to any of the compounds shown in Formula I and Formula II or carrier capture of the light-emitting material itself.

[0126] In one embodiment of the present invention, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes a light-emitting layer containing the organic electroluminescent composition as described above, and may also include any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0127] On the other hand, the present invention provides an application of the described organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0128] Terminology Explanation

[0129] 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 invention pertains.

[0130] As used herein, the terms “containing” or “including (comprise)” can be open-ended, semi-closed, or closed. In other words, the terms also include “consistently made of” or “composed of”.

[0131] Group definition

[0132] In this specification, groups and their substituents may be selected by those skilled in the art to provide stable structural moieties and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the structural formula is written from right to left.

[0133] The chapter headings used in this specification are for organizational purposes only and should not be construed as limiting the subject matter. All references or portions thereof cited in this invention, including but not limited to patents, patent applications, articles, books, user manuals, and papers, are incorporated herein by reference in their entirety.

[0134] Unless otherwise specified, all technical and scientific terms used herein have the standard meaning in the field to which the claimed subject matter pertains. Where multiple definitions exist for a term, the definition herein shall prevail.

[0135] It should be understood that the singular forms used in this invention, such as "a," include plural references unless otherwise specified. Furthermore, the term "comprising" is an open-ended limitation, not a closed one; that is, it includes the contents specified in this invention but does not exclude other aspects.

[0136] Unless otherwise stated, this invention employs traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can be referred to conventional operating procedures and conditions in the field.

[0137] Unless otherwise specified, this invention employs standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, organic synthetic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.

[0138] The compounds of the present invention may contain atomic isotopes in non-natural proportions on one or more atoms constituting the compound. For example, the compounds may be labeled with radioactive isotopes, such as deuterium (₂H). All variations in the isotopic composition of the compounds of the present invention, regardless of radioactivity, are included within the scope of the present invention.

[0139] In this invention, unless otherwise specified, the number of "substitutes" can be one or more; when there are multiples, it means two or more, such as two, three, or four. Furthermore, when there are multiple "substitutes," the "substitutes" can be the same or different. In this invention, unless otherwise specified, the position of the "substitute" can be arbitrary.

[0140] In this invention, as a group or part of other groups (e.g., in halogen-substituted alkyl groups), the term "alkyl" means a saturated aliphatic hydrocarbon group comprising branched and straight chains having a specified number of carbon atoms. For example, C1-C1...20 Alkyl groups include straight-chain or branched alkyl groups having 1 to 20 carbon atoms. As defined in "C1-C6 alkyl," it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight-chain or branched structure. For example, in this invention, each of the C1-C6 alkyl groups is independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; wherein, propyl is a C3 alkyl group (including isomers, such as n-propyl or isopropyl); butyl is a C4 alkyl group (including isomers, such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is a C5 alkyl group (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl, or neopentyl); and hexyl is a C6 alkyl group (including isomers, such as n-hexyl or isohexyl).

[0141] As used herein, the term "alkoxy" refers to an alkyl group as defined above, which is connected via an oxygen bond (-O-).

[0142] In this invention, as a group or part of other groups, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group (with only carbon atoms as ring atoms) having n to m ring carbon atoms, possessing at least one carbon ring with a conjugated π-electron system. Examples of the aforementioned aryl unit include phenyl, naphthyl, indene, azulel, fluorenyl, phenanthryl, or anthraceneyl. In one embodiment, the aryl group is preferably a C6-14 aryl group, such as phenyl and naphthyl, more preferably phenyl.

[0143] In this invention, as a group or part of other groups, the term "nm-aryl" refers to an aromatic group whose ring atoms comprise one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, having n to m ring atoms. The heteroaryl group is a monocyclic, bicyclic, tricyclic, or tetracyclic system, wherein at least one ring is an aromatic ring. Heteroaryl groups within this definition include, but are not limited to: acridinel, carbazolyl, cyclophosphinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thiophene, benzothiophene, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridinyl, pyrimidinel, pyrroleyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazolyl, thiadiazolyl, etc. Oxadiazole, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purine, pteridinyl, naphridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazinyl, benzothiazolyl, benzooxazinyl, benzoimidazolyl, isoindolyl, indazole, pyrrolopyridinyl, thienopyridinyl, furanolopyridinyl, benzothiadiazole, benzooxadiazole, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, as preferred examples of "5- to 18-membered heteroaryl groups", furanyl, thienoyl, pyrrololyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyrimidinyl, and carbazoleyl are listed, more preferably carbazoleyl.

[0144] 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 dicycloheptyl. In one embodiment, the C3-C10 cycloalkyl group is preferably adamantyl or cyclohexyl.

[0145] In this invention, the defined carbon number range of the group refers to any integer number of carbon atoms included within the defined range, such as C1 to C2. 20 This refers to the fact that the number of carbon atoms in the stated group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, C3-C. 10 This means that the number of carbon atoms in the group can be 3, 4, 5, 6, 7, 8, 9 or 10, and the range of carbon atoms for other groups can be deduced similarly.

[0146] Without violating common sense in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain various preferred embodiments of the present invention.

[0147] The reagents and raw materials used in this invention are all commercially available.

[0148] Compared with the prior art, the present invention has the following beneficial effects:

[0149] The boron-nitrogen compound of this invention, through extended conjugation and the introduction of nitrogen atoms, not only achieves fine-tuning of the spectrum but also further improves luminescence efficiency. The boron-nitrogen compound of this invention exhibits a narrow spectrum and can be used as a narrow-spectrum luminescent material to prepare the luminescent layer of organic electroluminescent devices. The organic electroluminescent devices prepared thereby achieve narrow-spectrum TADF emission, with the electroluminescence spectrum located in the green-yellow light region, a full width at half maximum (FWHM) of less than 45 nm, and achieve a maximum external quantum efficiency of over 34%. Attached Figure Description

[0150] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device of the present invention, wherein 1 is the ITO anode, 2 is the first hole transport layer, 3 is the second hole transport layer, 4 is the light-emitting layer, 5 is the second electron transport layer, 6 is the first electron transport layer, 7 is the electron injection layer, and 8 is the metal cathode.

[0151] Figure 2 This is the photoluminescence spectrum of compound BN-1.

[0152] Figure 3 This is the photoluminescence spectrum of compound BN-25.

[0153] Figure 4 This is the photoluminescence spectrum of compound BN-26.

[0154] Figure 5 The photoluminescence spectrum of compound BN-27 is shown.

[0155] Figure 6 The photoluminescence spectrum of compound BN-33 is shown.

[0156] Figure 7 This is the electroluminescence spectrum of compound BN-1. Detailed Implementation

[0157] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0158] In embodiments of the present invention, the raw materials used to synthesize the shown compounds are as follows:

[0159] The specific raw material An (n = 1-2) used includes the following molecules:

[0160]

[0161] The specific raw material Bn (n = 1-14) used includes the following molecules:

[0162]

[0163]

[0164] The synthetic route and specific operations used for the synthesis of the compound represented by Formula I are as follows:

[0165]

[0166] First, an arylboronic ester starting material An (n = 1-2) is coupled with a bromocarbazole derivative starting material Bn (n = 1-11) via a Suzuki reaction to obtain the intermediate BN-n-Pro (n = 1-2, 9, 14, 17-18, 22, 24, 25-28). Then, the target product BN-n (n = 1-2, 9, 14, 17-18, 22, 24, 25-28) is obtained using a Scholl oxidative coupling reaction.

[0167] In the first step, aryl borate ester raw material An (n = 1-2) (100.0 mmol), bromocarbazole derivative raw material Bn (n = 1-11) (105.0 mmol), and anhydrous potassium carbonate (200.0 mmol) were dispersed in a ternary solvent system of toluene, ethanol, and water (330 mL toluene, 80 mL ethanol, and 80 mL distilled water). Nitrogen gas was bubbled into the mixture for 10 minutes, and 2.0 mmol of tetrakis(triphenylphosphine)palladium was added under a nitrogen flow. The system was heated to 110 °C and stirred for 14 hours. After the reaction system cooled to room temperature, the solvent was first evaporated under vacuum, and then the product was extracted three times with dichloromethane and water. The combined organic phases were concentrated under vacuum and then purified by column chromatography to obtain the intermediate BN-n-Pro (n = 1-2, 9, 14, 17-18, 22, 24, 25-28).

[0168] In the second step, the intermediate BN-n-Pro (n = 1-2, 9, 14, 17-18, 22, 24, 25-28) was heated at 90°C under vacuum for 2 hours to remove residual organic solvents. Then, 50.0 mmol of the intermediate was dissolved in 500 mL of ultra-dry dichloromethane and cooled to 0°C using an ice-water bath. Under a nitrogen atmosphere, 130.0 mmol of DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) was added, and the mixture was stirred for 10-15 minutes. Then, 50 mL of a dichloromethane solution of methanesulfonic acid (10 mol / L) was added dropwise. After the addition was complete, the system was gradually brought to room temperature and stirred for 3 hours. After the starting material disappeared, 35.0 mmol of triethylamine was added to quench the reaction using TLC. The reaction system was then extracted three times with dichloromethane and water. The organic phases were combined, the product was concentrated under vacuum, and purified by column chromatography to obtain the target product BN-n (n=1-2,9,14,17-18,22,24,25-28).

[0169] The synthetic route and specific details of the experiment are illustrated using the example of compound BN-1 synthesis:

[0170]

[0171] In the first step, 76.7 g of starting material A1 (100.0 mmol), 33.8 g of starting material B1 (105.0 mmol), and 27.6 g of anhydrous potassium carbonate (200.0 mmol) were dispersed in a ternary solvent system of toluene, ethanol, and water (330 mL toluene, 80 mL ethanol, and 80 mL distilled water). Nitrogen gas was bubbled into the mixture for 10 minutes, and then 2.3 g of tetrakis(triphenylphosphine)palladium (2.0 mmol) was added under a nitrogen flow. The system was heated to 110 °C and stirred for 14 hours. After the reaction system cooled to room temperature, the solvent was first evaporated under vacuum, and then the product was extracted three times with dichloromethane and water. The combined organic phases were concentrated under vacuum and then purified by column chromatography to obtain intermediate BN-1-Pro (yellow solid, 85% yield).

[0172] In the second step, intermediate BN-1-Pro was heated to 90°C under vacuum for 2 hours to remove residual organic solvents. Then, 50.0 mmol of intermediate BN-1-Pro was dissolved in 500 mL of ultra-dry dichloromethane and cooled to 0°C using an ice-water bath. Under a nitrogen atmosphere, 29.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone (130.0 mmol) was added, and the mixture was stirred for 15 minutes. Then, 50 mL of a dichloromethane solution of methanesulfonic acid (10 mol / L) was added dropwise. After the addition was complete, the system was gradually brought to room temperature and stirred for 3 hours. After the starting material disappeared using TLC, 4.9 mL of triethylamine (35.0 mmol) was added to quench the reaction. The reaction mixture was then extracted three times with dichloromethane and water. The organic phases were combined, and the product was concentrated under vacuum and purified by column chromatography to obtain the target product BN-1 (orange solid, 91% yield).

[0173] The synthetic route and specific procedures used for the synthesis of the compound represented by Formula II are as follows:

[0174]

[0175] First, an arylboronic ester raw material An (n = 1-2) is coupled with a bromocarbazole derivative raw material Bn (n = 12-14) via a Suzuki reaction to obtain the intermediate BN-n-Pro (n = 33-34, 41, 43). Then, the target product BN-n (n = 33-34, 41, 43) is obtained by Scholl oxidative coupling reaction.

[0176] In the first step, aryl borate ester raw material An (n = 1-2) (100.0 mmol), bromocarbazole derivative raw material Bn (n = 12-14) (105.0 mmol), and anhydrous potassium phosphate (300.0 mmol) were dispersed in a binary solvent system of 1,4-dioxane and water (350 mL 1,4-dioxane and 6 mL distilled water). Nitrogen gas was bubbled into the mixture for 10 minutes, and then 2.0 mmol of 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride was added under a nitrogen flow. The system was heated to 100 °C and stirred for 14 hours. After the reaction system cooled to room temperature, the solvent was first evaporated under vacuum, and then the product was extracted three times with dichloromethane and water. The combined organic phases were concentrated under vacuum and then purified by column chromatography to obtain the intermediate BN-n-Pro (n = 33-34, 41, 43).

[0177] In the second step, the intermediate BN-n-Pro (n = 33-34, 41, 43) was heated at 90°C under vacuum for 2 hours to remove residual organic solvents. Then, 50.0 mmol of the intermediate was dissolved in 500 mL of ultra-dry dichloromethane and cooled to 0°C using an ice-water bath. Under a nitrogen atmosphere, 150.0 mmol of DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) was added, and the mixture was stirred for 10-15 minutes. Then, 60 mL of a dichloromethane solution of methanesulfonic acid (10 mol / L) was added dropwise. After the addition was complete, the system was gradually brought to room temperature and stirred for 3 hours. After the starting material disappeared using TLC, 42.0 mmol of triethylamine was added to quench the reaction. The reaction system was then extracted three times with dichloromethane and water. The organic phases were combined, the product was concentrated under vacuum, and purified by column chromatography to obtain the target product BN-n (n = 33-34, 41, 43).

[0178] The synthetic route and specific details of the experiment are illustrated using the synthesis examples of compound BN-33:

[0179]

[0180] In the first step, 76.7 g of raw material A1 (100.0 mmol), 33.8 g of raw material Bn (n = 12-14) (105.0 mmol), and 63.7 g of anhydrous potassium phosphate (300.0 mmol) were dispersed in a binary solvent system of 1,4-dioxane and water (350 mL of 1,4-dioxane and 6 mL of distilled water). Nitrogen gas was bubbled into the mixture for 10 minutes, and then 1.5 g of 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (2.0 mmol) was added under a nitrogen flow. The system was heated to 100 °C and stirred for 14 hours. After the reaction system cooled to room temperature, the solvent was first evaporated under vacuum, and then the product was extracted three times with dichloromethane and water. The combined organic phases were concentrated under vacuum and then purified by column chromatography to obtain intermediate BN-33-Pro (yellow solid, 56% yield).

[0181] In the second step, intermediate BN-33-Pro was heated to 90°C under vacuum for 2 hours to remove residual organic solvents. Then, 50.0 mmol of intermediate BN-33-Pro was dissolved in 500 mL of ultra-dry dichloromethane and cooled to 0°C using an ice-water bath. Under a nitrogen atmosphere, 34.1 g of 2,3-dichloro-5,6-dicyanobenzoquinone (150.0 mmol) was added, and the mixture was stirred for 15 minutes. Then, 60 mL of a dichloromethane solution of methanesulfonic acid (10 mol / L) was added dropwise. After the addition was complete, the system was gradually brought to room temperature and stirred for 3 hours. After the starting material disappeared using TLC, 5.9 mL of triethylamine (42.0 mmol) was added to quench the reaction. The reaction mixture was then extracted three times with dichloromethane and water. The organic phases were combined, and the product was concentrated under vacuum and purified by column chromatography to obtain the target product BN-33 (orange-yellow solid, 92% yield).

[0182] The products were characterized using an Agilent Technologies VarioMicro Cube instrument for elemental analysis, testing for C, H, and N. Mass spectrometry was performed using a Thermo Fisher TSQEndura ultra-high performance liquid chromatography-tandem triple quadrupole mass spectrometer.

[0183] The results of relevant photoluminescence tests on the compound showed that:

[0184] Taking compound BN-1 as an example, at room temperature, this compound emits at 519 nm and has a full width at half maximum (FWHM) of 37 nm in toluene solution (e.g., Figure 2 (As shown).

[0185] Taking compound BN-25 as an example, at room temperature, this compound emits at 535 nm and has a full width at half maximum (FWHM) of 44 nm in toluene solution (e.g., Figure 3 (As shown).

[0186] Taking compound BN-26 as an example, at room temperature, this compound emits at 520 nm and has a full width at half maximum (FWHM) of 37 nm in toluene solution (e.g., Figure 4 (As shown).

[0187] Taking compound BN-27 as an example, at room temperature, this compound emits at 530 nm and has a full width at half maximum (FWHM) of 44 nm in toluene solution (e.g., Figure 5 (As shown).

[0188] Taking compound BN-33 as an example, at room temperature, this compound emits at 521 nm and has a full width at half maximum (FWHM) of 44 nm in toluene solution (e.g., Figure 6 (As shown).

[0189] Table 1. Summary of product data from the synthesis examples

[0190]

[0191] Photoluminescence Examples and Electroluminescence Device Examples

[0192] The following are some representative examples of photoluminescent and electroluminescent devices. The molecular structures of some materials involved in the photoluminescence testing and device examples and comparative examples are as follows:

[0193]

[0194]

[0195] The following are examples of electroluminescent devices fabricated using the materials of the present invention, and the specific device fabrication process is as follows:

[0196] Fabrication process of organic electroluminescent devices:

[0197] The results of the device are as follows Figure 1 As shown, 1 is the ITO anode, 2 is the first hole transport layer, 3 is the second hole transport layer, 4 is the light-emitting layer, 5 is the second electron transport layer, 6 is the first electron transport layer, 7 is the electron injection layer, and 8 is the metal cathode.

[0198] The preparation process is as follows:

[0199] (1) Substrate treatment: Transparent ITO glass was used as the substrate material for device fabrication. It was first ultrasonically treated with 5% ITO cleaning solution for 30 minutes, then sequentially ultrasonically washed with distilled water (twice), acetone (twice), and isopropanol (twice). Finally, the ITO glass was stored in isopropanol. Before each use, the surface of the ITO glass was carefully wiped with acetone and isopropanol cotton balls, rinsed with isopropanol, dried, and then plasma-treated for 5 minutes before use. Device fabrication was completed using a combination of spin coating and vacuum evaporation processes.

[0200] (2) Preparation of hole injection layer and hole transport layer: The hole transport layer was prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reached 5×10 -4 Vacuum deposition begins when the pressure is below a certain level. The deposition rate is determined using a SAINS film thickness gauge. Organic hole transport layers are sequentially deposited on the ITO electrode surface using a vacuum evaporation process. The deposition rate of the hole transport material is [missing information].

[0201] (3) Preparation of the light-emitting layer: The light-emitting layer is prepared by evaporation deposition process. When the vacuum degree of the vacuum evaporation deposition system reaches 5×10 - 4 Vacuum deposition begins when the pressure is below a certain level (Pa). The deposition rate is determined using a SAINS film thickness gauge. The luminescent layer is sequentially deposited on the hole transport layer using a vacuum evaporation process. The deposition rate of the luminescent layer material is [missing information].

[0202] (4) Fabrication of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are fabricated using a vapor deposition process. When the vacuum degree of the vacuum deposition system reaches 5×10 -4 Vapor deposition begins when the pressure is below a certain level (Pa). The deposition rate is measured using a SAINS film thickness gauge. An organic electron transport layer, a LiF electron injection layer, and a metal Al electrode are sequentially deposited on the light-emitting layer using a vacuum evaporation process (see the following effect example for specific device structure). The deposition rate of the organic material is [missing information - likely a specific value]. The deposition rate of LiF is The deposition rate of Al is

[0203] Device Example 1-n (n=16)

[0204] Organic electroluminescent devices (structures as shown in Device Examples 1-n (n = 1-16)) Figure 1 In the example shown, HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-172 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-79 is used as the second electron transport layer, TRZ-4 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%H1-172+1wt%BN-m(30nm) / TRZ-79(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0205] Performance data for the device embodiments are shown in Table 2. The current, voltage, luminance, and emission spectrum characteristics of the device were simultaneously tested using a Photo Research PR 655 spectral scanning luminance meter and a Keithley K 2400 digital source meter system. The device performance tests were conducted at room temperature and under ambient atmosphere. The external quantum efficiency (EQE) of the device was calculated based on the Lambaugh distribution of emission, using current density, luminance, and electroluminescence spectrum combined with the apparent function (the same applies below). In Table 2, the device lifetime (T97, hours) refers to the device with an initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 97% of its initial brightness (i.e., the device brightness drops to 970 cd / m²), 2 The time required (in hours).

[0206] Comparative device embodiments D1-n (n=1-8)

[0207] Organic electroluminescent devices (structures as shown in the comparative device examples 1-n (n=1-8)) Figure 1 In the example shown, HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-172 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 1wt%), TRZ-79 is used as the second electron transport layer, TRZ-4 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the effect example is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 99wt%H1-172+1wt%Rm(30nm) / TRZ-79(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0208] Performance data for the comparative device examples are shown in Table D2. In Table D2, device lifetime (T97, hours) refers to the device's initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 97% of its initial brightness (i.e., the device brightness drops to 970 cd / m²), 2 The time required (in hours).

[0209] Figure 7 The image shows the electroluminescence spectrum of compound BN-1, with an emission peak at 524 nm and a full width at half maximum (FWHM) of 41 nm.

[0210] Table 2

[0211]

[0212] Table D2

[0213]

[0214] Device Example 2-n (n = 1-16)

[0215] Organic electroluminescent devices (structures as shown in Device Examples 2-n (n = 1-16)) Figure 1In the example shown, HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-172+TRZ-79 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-79 is used as the second electron transport layer, TRZ-4 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the effect embodiment is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 70wt%H1-172+29wt%TRZ-79+1wt%BN-m(30nm) / TRZ-79(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0216] Performance data for the device embodiments are shown in Table 3. In Table 3, the device lifetime (T97, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 97% of its initial brightness (i.e., the device brightness drops to 970 cd / m²), 2 The time required (in hours).

[0217] The device structure is not suitable for R1, R2, R3, R4, R5, R6, R7 and R8 because the energy transfer from the subject to the object is incomplete.

[0218] Table 3

[0219]

[0220] Device Example 3-n (n=1-16)

[0221] Organic electroluminescent devices (structures as shown in Device Examples 3-n (n = 1-16)) Figure 1In the example shown, HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-215+2CN-47 is used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-77 is used as the second electron transport layer, TRZ-4 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the effect embodiment is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 70wt%H1-215+29wt%2CN-47+1wt%BN-m(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0222] Performance data for the device embodiments are shown in Table 4. In Table 4, the device lifetime (T97, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 97% of its initial brightness (i.e., the device brightness drops to 970 cd / m²), 2 The time required (in hours).

[0223] The device structure is not suitable for R1, R2, R3, R4, R5, R6, R7 and R8 because the energy transfer from the subject to the object is incomplete.

[0224] Table 4

[0225]

[0226] Device Example 4-n (n = 1-16)

[0227] Organic electroluminescent devices (structures as shown in Device Examples 1-n (n = 1-16)) Figure 1In the example shown, HIM-doped HTL-1 is used as the first hole transport layer, HTL-2 is used as the second hole transport layer, H1-215+IrPPy is used as the host material in the light-emitting layer, BN-m (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-77 is used as the second electron transport layer, TRZ-4 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the effect embodiment is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 90wt%H1-215+9wt%IrPPy+1wt%BN-m(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0228] Performance data for the device embodiments are shown in Table 5. In Table 5, the device lifetime (T97, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 97% of its initial brightness (i.e., the device brightness drops to 970 cd / m²), 2 The time required (in hours).

[0229] The device structure is not suitable for R1, R2, R3, R4, R5, R6, R7 and R8 because the energy transfer from the subject to the object is incomplete.

[0230] Table 5

[0231]

[0232]

[0233] The applicant declares that the boron-nitrogen compounds and their applications are illustrated through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound has the structure shown in Formula I or Formula II: Y1, Y2, Y3, and Y4 are independently CH and CR. 13 CR 14 Or N; Y5, Y6, Y7, and Y8 are independently CH and CR. 11 CR 12 Or N; R, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, and dominated by one or more R a Substituted C6-C18 aryl, 5- to 18-heteroaryl, and substituted with one or more R a Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R a Substituted diphenylamine group; R a Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R b Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R b Substituted diphenylamine group; R b Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R c Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R c Substituted diphenylamine group; R c Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R d Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R d Substituted diphenylamine group; R d Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or is affected by one or more R groups. e Substituted C6-C14 aryl groups; R e Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independent existence or R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them forms a ring with the connected aromatic ring; The alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl groups are optionally substituted with one or more substituents selected from the following: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl.

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 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independently H, deuterium, C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R a Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R b Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R c Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R d Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, carbazole, or alkyl-substituted phenyl groups with at least one C1-C bond 12 Alkyl-substituted carbazole group; Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independently, H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexoxy 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 connection sites of the functional groups; Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 1 R 9 R 10 R 11 R 12 R 13 and R 14 Independently, H, methyl, 2-methyl-phenyl, phenyl, The wavy lines represent the connection sites of the functional groups; Preferably, R is selected from H, D, phenyl, biphenyl, and C1-C10 alkyl-substituted phenyl. More preferably, R is selected from H, D, or phenyl.

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 includes, as a dopant material, a boron nitride compound as described in any one of claims 1-3 and a host material; Preferably, the host material is a material with electron transport capability and / or hole transport capability and whose triplet excited state energy is higher than or equal to the triplet excited state energy of the doped luminescent material.

5. The organic electroluminescent composition according to claim 4, characterized in that, The host material is a compound having a structure as shown in any one of formulas (H-1) to (H-10): Where 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, it can be any of the following groups: Where X2, Y2, and Z2 are CH or N, and at most one of X2, Y2, and Z2 is N; Where R aH and R bH Independent of 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 group, * indicates the linkage 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 It is 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 as described in any one of claims 1-3 as a dopant material, and the remaining 99.7-70.0 wt% is a host material composed of 1-2 compounds having the structure of formula (H-1) to formula (H-10); Preferably, the main material contains two compounds having structures of formula (H-1) to (H-10), and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains 0.3-30.0 wt% of the boron nitrogen compound as described in any one of claims 1-3, and the remaining 99.7-70.0 wt% is one or two compounds selected from compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition contains two compounds selected from H1-1 to H1-254 as the main material, 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 1-3; the main material is composed of any one of the compounds shown in formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds having the structure shown in 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 independent as R Tz The remaining elements are, independently and identically, hydrogen, deuterium, C1-C8 alkyl, C1-C8 alkoxy, or C6-C4. 18 Aryl, C1-C8 alkyl substituted C6-C 18 Aryl or C1-C8 alkoxy-substituted C6-C 18 aryl; R Tz It can be any of the substituents shown in the following formula: The asterisk represents the linking site of the functional group; Preferably, the ratio of the compounds shown in Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A to the compounds shown in H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H9 or H-10 in the main material is 1:20 to 20:1; Preferably, the weight ratio between the compound represented by formula TRZ-1 to TRZ-86 in the main material and the carbazole or carbline derivative with the structure represented by any one of formulas (H-1) to (H-10) is 1:20 to 20:1; Preferably, the weight ratio of the compounds represented by formulas TRZ-1 to TRZ-86 to the compounds represented by formulas H1-1 to H1-254 in the main material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is a boron nitrogen compound according to any one of claims 1-3; the host material is composed of any one of the compounds of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds of formulas H-1 to H-10; in the host material, the weight ratio between the compounds of formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A and the compounds of formulas 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 any one of the compounds shown in Formula I and Formula II; the host material is composed of any one of the 1,3,5-triazine derivatives shown in Formula TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives shown in Formula H1-1 to H1-254; in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one of the compounds shown in formulas BN-1 to BN-48; the host material is composed of any one of the compounds of formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-254; in the host material, the weight ratio between the compounds of formulas Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A and the carbazole or carboline derivatives shown in 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 shown in formulas BN-1 to BN-48; the host material is composed of any one of the 1,3,5-triazine derivatives shown in formulas TRZ-1 to TRZ-86 and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-254; in the host material, the weight ratio between the 1,3,5-triazine derivatives shown in formulas TRZ-1 to TRZ-86 and the carbazole or carboline derivatives shown in formulas H1-1 to H1-254 is 1:20 to 20:

1. Preferably, in the organic electroluminescent composition, the main material is composed of any one of the compounds having the structure shown in formulas H-1 to H-10 and any one of the compounds shown in formulas Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6; 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 It is independently C6-C24 aryl or C12-C36 heteroaryl; R si (i = 7-39) 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 one of the following 24 groups: An asterisk (*) represents a linking site of a functional group. Preferably, Rs i (i = 7-39) Independently selected from any one of the following 5 groups: *H*- D *-CH3 An asterisk (*) represents a linking site of a functional group. Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds as described in any one of claims 1-3, and the host material is any one of the compounds shown in formulas 2CN-1 to 2CN-60 and any one of the compounds shown in formulas H1-1 to H1-254; Preferably, the doping material in the organic electroluminescent composition is a boron-nitrogen compound as described in any one of claims 1-3; the host material is composed of any one of 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 compounds of formulas H-1 to H-10; preferably, in the host material, the weight ratio between compounds of formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and compounds of formulas 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 a boron nitrogen compound as described in any one of claims 1-3; the main material is composed of any one of the dicyanophenyl derivatives shown in formula 2CN-1 to 2CN-60 and any one of the carbazole derivatives shown in formula H1-1 to H1-254; preferably, in the main material, the weight ratio between the dicyanophenyl derivative and the carbazole derivative is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-48, and the host material is composed of any one of the compounds shown in formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and any one of the compounds shown in formula H1-1 to H1-254; preferably, in the host material, the weight ratio between the compound of formula Ph-2CN-1, Ph-2CN-2, Ph-2CN-3, Ph-2CN-4, Ph-2CN-5 or Ph-2CN-6 and the compound shown in formula 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 shown in formulas BN-1 to BN-48, and the host material is composed of any one of the dicyanophenyl derivatives shown in formulas 2CN-1 to 2CN-60 and any one of the compounds shown in formulas H1-1 to H1-254; preferably, in the host material, the weight ratio between the dicyanophenyl derivatives shown in formulas 2CN-1 to 2CN-60 and the carbazole derivatives shown in formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is a boron nitrogen compound as described in any one of claims 1-3, and the main material is composed of any one of the compounds shown in formulas H1-1 to H1-254 and phosphorescent compounds containing metal Ir or Pt as shown in formulas Ir-1, Ir-2 and Pt-; preferably, in the main material, the weight ratio between the compound shown in formulas H1-1 to H1-254 and the phosphorescent compound containing metal Ir is 1:20 to 20:

1. R ri Independently hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, where i is an integer from 1 to 22, and the dashed line represents two double bonds that are separated by two of the four bonds contained. R ri Any one of the groups can form a ring with the aromatic ring or aromatic heterocycle attached to it; Preferably, the phosphorescent compound containing metallic Ir is any one of the following compounds: Preferably, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any compound shown in formulas BN-1 to BN-48, and the main material is composed of any carbazole or carboline derivatives shown in formulas H1-1 to H1-254 and phosphorescent compounds containing metallic Ir shown in formulas Ir-1 and Ir-2. Preferably, in the main material, the weight ratio between carbazole or carboline derivatives shown in formulas H1-1 to H1-254 and phosphorescent compounds containing metallic Ir is 1:20 to 20:

1.

6. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes any boron nitrogen compound as described in any one of claims 1-3 or the organic electroluminescent composition as described in claim 4 or 5.

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

8. The organic electroluminescent device according to claim 7, 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, electron injection layer, electron transport layer, hole transport layer, and hole injection layer comprises a boron nitride compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5.

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

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

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