Boron-nitrogen compounds and their use

Abstract

The present application provides a kind of boron-nitrogen compound and its application, the boron-nitrogen compound has the structure shown in formula I and formula II, the boron-nitrogen compound of the present application is based on the compound formed by optimizing the structure of carbazole derivative-boron-nitrogen compound.The boron-nitrogen compound of the present application has narrow spectrum luminescence characteristics, as narrow spectrum luminescence material for preparing the light-emitting layer of organic electroluminescence device, the organic electroluminescence device prepared thereby realizes narrow spectrum TADF emission, half peak width is less than 45nm, and makes the highest electroluminescence external quantum efficiency of device be as high as 30% or more.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology and relates to a boron nitrogen compound and its applications. Background Technology

[0002] Organic optoelectronic materials are a class of organic materials that possess properties such as the generation, conversion, and transmission of photons and electrons. Currently, the controllable optoelectronic properties of organic optoelectronic materials have been applied to organic light-emitting diodes (OLEDs), organic solar cells (OPVs), organic field-effect transistors (OFETs), and even organic lasers. In recent years, OLEDs have become a very popular new type of flat panel display product both domestically and internationally. OLED displays feature self-emissive characteristics, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panels, the ability to manufacture large-size flexible panels, and low cost, earning them the reputation as 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, ScienceDirect. Sensors and Actuators B: Chemical, 1995, 29, 213.). About 10 years later, in 1963, Pope et al. of New York University observed the fluorescence emission of anthracene by applying a voltage to anthracene crystals (M. Pope, H. Kallmann and P. Magnante, Electroluminescence in Organic Crystals, J. Chem. Phys., 1963, 38, 2042). In 1987, CWTang et al. of Kodak Corporation in the United States used ultrathin film technology, employing 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 a metal alloy as the anode and cathode, respectively, to fabricate a light-emitting device. This device achieved a brightness of 1000 cd / m² at a driving voltage of 10V. 2The green light emission of the device, with an efficiency of 1.5 lm / W (CWTangandS.A.VanSlyke, Organic electroluminescent diodes, Appl. Phys. Lett., 1987, 51, 913), was a breakthrough that led to the rapid and in-depth development of organic electroluminescence research worldwide. In 1990, Burroughes et al. of Cambridge University proposed the first light-emitting diode based on polymer (PPV). This showed that PPV, in monolayer devices, can serve as a highly fluorescent emitting material with high luminous efficiency (Burroughes J Hetal., Light-emitting diodes based on conjugated polymers, Nature, 1990, 347, 539). In 1998, Baldo and Forrest et al. from Princeton University reported the first phosphorescent device based on electroluminescence, which in principle could have 100% internal quantum yield (MA Baldo, DFO' Brinetal., 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 still have chemical instability and large efficiency roll-off problems at high current densities. Therefore, it is extremely important to develop an OLED device that can achieve high-efficiency light emission using inexpensive and stable small organic molecule materials.

[0004] In 2012, the Adachi research group at Kyushu University reported a highly efficient all-fluorescent OLED device 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 energy difference between the S1 and T1 levels of a molecule is sufficiently small, the triplet exciton can absorb thermal energy, return to the singlet state through a RISC process, and then emit fluorescence. Theoretically, the internal quantum efficiency (IQE) of this device can reach 100%, and the external quantum efficiency (EQE) can even reach 30%, comparable to the level of phosphorescent devices. As a next-generation luminescent material, research on TADF materials is booming.

[0005] TADF molecules are mainly used as guest materials to dope in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (Q. Zhang, J. Li, K. Shizu, et al. Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes, J. Am. Chem. Soc. 2012, 134, 14706; H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, 2012, 492, 234; T. Nishimoto, T. Yasuda, et al. A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs, Mater. Horiz. 2014, 1, 264). Unlike traditional localized (LE) state luminescence in fluorescent molecules, TADF emission primarily originates from transitions in the ICT state. Therefore, it is easily affected by vibrational and rotational motions between the donor and acceptor, resulting in a broader spectrum and a longer delayed fluorescence excitation lifetime. Consequently, electroluminescent devices based on TADF luminescent materials exhibit poor stability. Although pure organic TADF luminescent materials eliminate dependence on noble metals and offer the advantage of low cost, their poor emission spectral color purity and stability remain major challenges. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide a boron-nitrogen compound and its applications. The compound provided by the present invention aims to solve the defects of TADF luminescent molecules, providing a luminescent material with a narrow emission spectrum and good stability, which can be used to prepare the luminescent layer of organic electroluminescent devices, thereby enabling organic electroluminescent devices to exhibit excellent characteristics.

[0007] To achieve this objective, the present invention employs the following technical solution:

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

[0009]

[0010] E 1 This indicates whether there are single-key links or not.

[0011] E 2 E 3 and E 4 This indicates whether there are single-key links or not, and E 2 E 3 and E 4 One of (E 2 E 3 or E 4 ) represents no single-key link, and the other two represent single-key links, specifically including the following three cases: (1) E 2 and E 3 Represents a single-key link, E 4 This indicates that there are no single-key links; (2) E 3 and E 4 Represents a single-key link, E 2 This indicates that there are no single-key links; (3)E 2 and E 4 Represents a single-key link, E 3 This indicates that there are no single-key links.

[0012] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 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;

[0013] 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. bSubstituted 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;

[0014] 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;

[0015] 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;

[0016] 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;

[0017] R e Each time it appears, it is independently 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 8 R 9 R 10 R 11 R 12 R 13 and R 14 Independent existence or R 1 R 2 R3 R 4 R 5 R 6 R 7 R 8 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;

[0019] R 15 and R 16 It is H, D (deuterium), C1-C18 alkyl, C6-C18 aryl, or with one or more R a Substituted C6-C18 aryl, 5- to 24-membered heteroaryl, or substituted with one or more R a Substituted 5- to 18-membered heteroaryl groups.

[0020] 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.

[0021] 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 R 10 R 11 R 12 R 13 and R 14 Independently 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.

[0022] Preferably, the R a Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10cycloalkyl, 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] Preferably, the R 1 R 2 R3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 Independently, it is hydrogen, 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

[0027]

[0028] The wavy lines represent the connection sites of the functional groups;

[0029] Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 Independently hydrogen, methyl, 2-methyl-phenyl, Phenyl,

[0030] The wavy lines represent the connection sites of the functional groups.

[0031] Preferably, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R12 R 13 and R 14 At least one of them forms a ring structure with the connected aromatic ring as follows:

[0032] The bond marked with an asterisk (*) is a bond shared with the aromatic ring.

[0033] In some embodiments of the present invention, the boron nitrogen compound is any one of the following compounds:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] On the other hand, the present invention provides an organic electroluminescent material, wherein the organic electroluminescent material comprises the boron nitrogen compound as described above.

[0043] 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 a boron nitrogen compound as described above.

[0044] 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 a boron-nitrogen compound as described above.

[0045] In this invention, the boron nitride compound having the structure shown in Formula I and Formula II can be used as a functional material in at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer of an organic electroluminescent device.

[0046] In one embodiment, the organic electroluminescent device of the present invention may further include an optional hole blocking layer, an optional electron blocking layer, and an optional capping layer, etc.

[0047] In one embodiment, the organic electroluminescent device has, for example... Figure 1 The structure shown is as follows: 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.

[0048] In one embodiment, the boron nitride compound having the structures shown in Formula I and Formula II is used to prepare the light-emitting layer in an organic electroluminescent device.

[0049] 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.

[0050] On the other hand, the present invention provides an organic electroluminescent composition comprising, as described above, a boron nitride compound as a dopant and a host material;

[0051] Preferably, the host material is a material having electron transport capability and / or hole transport capability and whose triplet excited state energy is equal to or higher than the triplet excited state energy of the doped material.

[0052] In one embodiment of the present invention, the host material is a carbazole derivative and / or a carbline derivative having a structure as shown in any one of formulas (H-1) to (H-10):

[0053]

[0054]

[0055] Where X1, Y1, and Z1 are CH or N, and at most one of X1, Y1, and Z1 is N;

[0056] Where R 1H and R 2H Independently, it can be any of the following groups:

[0057]

[0058] Where X2, Y2, and Z2 are CH or N, and at most one of X2, Y2, and Z2 is N;

[0059] Where R aH and R bH Independent of H, C1-C 20 Alkyl, C1-C 20Alkoxy, 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;

[0060] W 1 W 2 W 3 W 4 W 5 W 6 W 7 W 8 and W 9 Independently S or O;

[0061] 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.

[0062] 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 nitride compound as 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%) is a host material composed of one or two compounds having the structure of formula (H-1) to formula (H-10);

[0063] In one embodiment of the present invention, 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, for example 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0064] Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-254;

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] In one embodiment of the present invention, the organic electroluminescent composition contains 0.3-30.0 wt% (e.g., 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 boron nitrogen compounds with the structures shown in Formula I and Formula II as described above, 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%) is one or two compounds selected from H1-1 to H1-254.

[0076] In a preferred embodiment of the present invention, 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, for example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0077] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds with the structure 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 having the structure shown in Formulas H-1 to H-10.

[0078] In a preferred embodiment, the ratio of the compounds shown as Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, or Trz6-A in the main material to the compounds shown as H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H9, or H-10 is from 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.

[0079]

[0080] 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:

[0081]

[0082]

[0083] The asterisk represents the linking site of the functional group.

[0084] In a preferred embodiment, the weight ratio between the compound represented by formula TRZ-1 to TRZ-86 in the host 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, 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.

[0085] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in Formula I and Formula II (content 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.

[0086] 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 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.

[0087] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-136 (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.

[0088] In a preferred embodiment, the organic electroluminescent composition is a light-emitting layer; the dopant in the organic electroluminescent composition is any one of the compounds shown in formula BN-1 to BN-136 (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 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, such as 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:5, 1:3, 1:1, 2:1, 3:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 19:1, or 20:1, etc.

[0089]

[0090]

[0091]

[0092]

[0093] In this invention, the main material of the organic electroluminescent composition 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.

[0094]

[0095]

[0096] Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are independently O (oxygen) or S (sulfur);

[0097] R s1 R s2 R s3 R s4 R s5 and R s6 It is independently C6-C24 aryl or C12-C36 heteroaryl;

[0098] R si (i = 7-39) independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl;

[0099] Preferably, R s1 R s2 R s3 R s4 R s5 and R s6 Independently selected from any one of the following 24 groups:

[0100]

[0101] An asterisk (*) represents the linking site of a functional group.

[0102] Preferably, R si (i = 7-39) Independently selected from any one of the following 5 groups:

[0103] *-H *—D *-CH3 An asterisk (*) represents the linking site of a functional group.

[0104] Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds with the structure shown in Formula I and Formula II as described above, and the host material is any one of the compounds shown in Formula 2CN-1 to 2CN-60 and any one of the compounds shown in Formula H1-1 to H1-254.

[0105]

[0106]

[0107]

[0108] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition may be a carbazole derivative and / or a carbline derivative as shown in formulas (H-1) to (H-10). In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any compound shown in formulas I and II, and the remaining 99.7-70.0 wt% is a host composed of 1-2 compounds having the structure of formulas (H-1) to (H-10). For example, when the host contains two compounds having the structure of formulas (H-1) to (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.

[0109] 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.

[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 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.

[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 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.

[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 BN-1 to BN-136 (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.

[0113] 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.

[0114] 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.

[0115] 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-136 (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.

[0116] 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-136 (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.

[0117] 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.

[0118]

[0119] R ri (rn is an integer from 1 to 22) is independently hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, where i is an integer from 1 to 22, and the dashed line represents that the two bonds separated by each other in the four bonds contained are double bonds;

[0120] R ri Any one of the groups can form a ring with the aromatic ring or aromatic heterocycle attached to it;

[0121] Preferably, the phosphorescent compound containing metallic Ir or Pt is any one of the following compounds:

[0122]

[0123]

[0124] 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-136 (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.

[0125] On the other hand, the present invention provides an organic electroluminescent material comprising the organic electroluminescent composition as described above.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] Terminology Explanation

[0134] 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.

[0135] 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”.

[0136] Group definition

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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).

[0146] As used herein, the term "alkoxy" refers to an alkyl group as defined above, which is connected via an oxygen bond (-O-).

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] The reagents and raw materials used in this invention are all commercially available.

[0153] Compared with the prior art, the present invention has the following beneficial effects:

[0154] 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 a full width at half maximum (FWHM) of less than 45 nm, and achieve a maximum external quantum efficiency of over 30% for electroluminescence. Attached Figure Description

[0155] 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.

[0156] Figure 2 The photoluminescence spectrum of compound BN-53 is shown.

[0157] Figure 3 The photoluminescence spectrum of compound BN-59 is shown.

[0158] Figure 4 This is the photoluminescence spectrum of compound BN-60. Detailed Implementation

[0159] 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.

[0160] When E1 represents the absence of single bonds, the general formula for the synthesis reaction of Equation I is as follows:

[0161]

[0162] When E1 represents the absence of single bonds, the general formula for the synthesis reaction of Equation II is as follows:

[0163]

[0164] When E1 represents a single bond connection, the general formula for the synthesis reaction of Equation I is as follows:

[0165] When E1 represents a single bond connection, the general formula for the synthesis reaction of Equation II is as follows:

[0166] In a specific synthetic embodiment of the present invention, the raw materials used to synthesize the compound are as follows: The raw material R specifically used includes the following molecules:

[0167]

[0168] The specific raw material Ai used includes the following molecules:

[0169] The specific raw material Bi used includes the following molecules:

[0170] The specific raw material Ci used includes the following molecules:

[0171] The specific raw material Di used includes the following molecules:

[0172]

[0173] The specific raw material Ei used includes the following molecules:

[0174]

[0175] The specific raw material Fi used includes the following molecules:

[0176]

[0177] The specific raw material Gi used includes the following molecules:

[0178]

[0179] The specific synthetic route details are illustrated using the synthesis of BN-53 as an example:

[0180]

[0181] In the first step, under a nitrogen atmosphere, 27.9 g of starting material A1 (100.0 mmol), 20.8 g of starting material 1-bromo-2-chloro-3-fluorobenzene (100 mmol), and 48.9 g of cesium carbonate (150.0 mmol) were added to 500 mL of DMF (N,N-dimethylformamide). The mixture was stirred at 150 °C for 24 hours, then cooled to room temperature. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried under vacuum by heating, and then purified by column chromatography to obtain intermediate F-A1 in 92% yield.

[0182] In the second step, 37.4 g of starting material F-A1(I) (80.0 mmol), 12.1 g of starting material B1 (80.0 mmol), and 39.1 g of cesium carbonate (120.00 mmol) were added to 300 mL of dry toluene. The mixture was bubbled with nitrogen for 10 minutes, and 0.2 mmol of palladium acetate and 0.2 mmol of XantPhos were added under high flow rate nitrogen. The mixture was heated to 110 °C and stirred for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was dried under vacuum by heating, and then purified by column chromatography to obtain intermediate F-A1B in 87% yield.

[0183] In the third step, a solution of 240.0 mmol of 4-tert-butylphenyl magnesium bromide in diethyl ether was slowly added dropwise to a 500 mL solution of tetrahydrofuran (-40°C) containing 32.3 g of intermediate F-A1B (60.0 mmol). After slowly heating to room temperature and stirring for 12 hours, the reaction system was concentrated under vacuum. Then, a mixed solution of 500 mL of acetic acid and 100 mL of hydrochloric acid was added to the system, and the mixture was heated to 100°C and stirred for another 6 hours. After cooling to room temperature, the reaction system was poured into ice water, extracted with dichloromethane, concentrated under vacuum, and purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to obtain the target product F-A1BC1 in 85% yield.

[0184] In the fourth step, 22.7 g of starting material F-A1BC1 (30.0 mmol), 9.6 g of starting material D1 (30.0 mmol), and 5.8 g of sodium tert-butoxide (60.0 mmol) were added to dry toluene (500 ml). The mixture was bubbled with nitrogen for 10 minutes, and 0.2 mmol of tris(dibenzyl)palladium and 0.4 mmol of X-Phos were added under high flow nitrogen. The mixture was heated to 110 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was dried under vacuum by heating, and then purified by column chromatography to obtain the target product Pre-BN in 87% yield.

[0185] In step 5, a hexane solution of 50.0 mmol of tert-butyllithium was slowly added to a 300 mL tert-butylbenzene solution (-30°C) containing 19.9 g of intermediate Pre-BN (20.0 mmol). The mixture was slowly heated to room temperature and stirred for 2 hours, then cooled to -30°C, and 15.0 g of boron tribromide (60.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. Then, 15.5 g of DIEA (120.0 mmol) was added at 0°C, and the reaction mixture was heated to 150°C and stirred for 12 hours, then cooled to room temperature. The reaction mixture was concentrated under vacuum and purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give the yellow target product BN-53 in 23% yield.

[0186] The specific synthetic route details are illustrated using the synthesis of BN-69 as an example:

[0187]

[0188] In the first step, under a nitrogen atmosphere, 27.9 g of starting material A1 (100.0 mmol), 33.4 g of starting material 1-bromo-3-chloro-4-fluoro-2-iodobenzene (100 mmol), and 48.9 g of cesium carbonate (150.0 mmol) were added to 500 mL of DMF (N,N-dimethylformamide). The mixture was stirred at 135 °C for 24 hours, then cooled to room temperature. The reaction mixture was extracted with dichloromethane and water. The organic phase was dried under vacuum by heating, and then purified by column chromatography to obtain intermediate FF-A1 in 80% yield.

[0189] In the second step, 35.6 g of starting material FF-A1 (60.0 mmol), 5.6 g of starting material F1 (60.0 mmol), and 11.5 g of sodium tert-butoxide (120.00 mmol) were added to 300 mL of dry toluene. The mixture was bubbled under nitrogen for 10 minutes, and then 0.2 mmol of tris(dibenzyl)palladium and 0.4 mmol of tri-tert-butylphosphine tetrafluoroborate were added under high flow rate nitrogen. The mixture was heated to 110 °C and stirred for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, and the organic phase was dried under vacuum by heating. The resulting product was then purified by column chromatography to obtain intermediate FF-A1F in 87% yield.

[0190] In the third step, 27.9 g of starting material FF-A1F (50.0 mmol) and 0.1 mmol of 4-dimethylaminopyridine (DMAP) were added to 300 mL of acetonitrile. Under ice bath conditions, 10.9 g of Boc2O (50.0 mmol) was slowly added dropwise to the system, and then the mixture was slowly heated to room temperature for 3 hours. Subsequently, the reaction mixture was extracted with dichloromethane and water, and the organic phase was dried under vacuum by heating. The mixture was then purified by column chromatography to obtain intermediate A1FB in 87% yield.

[0191] In the fourth step, under a nitrogen atmosphere, a hexane solution of 60 mmol of n-butyllithium was slowly added to a 300 mL tetrahydrofuran solution (-30°C) containing 26.3 g of intermediate A1FB (40.0 mmol), and the reaction was carried out at this temperature for 1 hour. Subsequently, a tetrahydrofuran solution of 14.4 g of G1 (9-fluorenone, 80 mmol) was slowly added, and the system was stirred at room temperature for 24 hours. The reaction mixture was extracted with dichloromethane and an aqueous solution of ammonium chloride, and the organic phase was evaporated to dryness under vacuum to obtain the hydroxyl intermediate. This intermediate was then dissolved in dichloromethane, and 200.0 mmol of methanesulfonic acid was slowly added with stirring at room temperature, and the reaction was continued at room temperature for 6 hours. The reaction mixture was then extracted with dichloromethane and an aqueous solution, and the organic phase was evaporated to dryness under vacuum to obtain intermediate A1-SF, yield: 62%.

[0192] In the fifth step, 14.8 g of raw material A1-SF (20.0 mmol) was added to a mixed solution containing 50 ml HCl and 200 ml ethanol. The mixture was heated to 85 °C and stirred for 3 hours. After the reaction was complete, the reaction mixture was extracted with dichloromethane and water. The organic phase was dried under vacuum and then purified by column chromatography to obtain intermediate A1SF with a yield of 87%.

[0193] In step six, 9.6 g of starting material A1SF (15.0 mmol), 4.8 g of starting material D1 (15.0 mmol), and 2.9 g of sodium tert-butoxide (30.0 mmol) were added to dry toluene (300 ml). The mixture was bubbled with nitrogen for 10 minutes, and 0.2 mmol of tris(dibenzyl)palladium and 0.4 mmol of X-Phos were added under high flow nitrogen. The mixture was heated to 110 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was dried under vacuum, and then purified by column chromatography to obtain the target product PreBN in 87% yield.

[0194] Step 7: A hexane solution of 30.0 mmol tert-butyllithium was slowly added to a 100 mL tert-butylbenzene solution containing 8.8 g of intermediate PreBN (10.0 mmol) (-30 °C). The mixture was slowly heated to room temperature and stirred for 2 hours, then cooled to -30 °C. 12.5 g boron tribromide (50.0 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then, 12.9 g DIEA (100.0 mmol) was added at 0 °C, and the reaction mixture was heated to 150 °C and stirred for 12 hours, then cooled to room temperature. The reaction mixture was concentrated under vacuum and purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give the yellow target product BN-69 in 32% yield.

[0195] Table 1. Summary of product data from the synthesis examples

[0196]

[0197]

[0198]

[0199] Figure 2 The photoluminescence spectrum of compound BN-53 is shown, with an emission peak at 531 nm and a full width at half maximum (FWHM) of 28 nm.

[0200] Figure 3 The photoluminescence spectrum of compound BN-59 is shown, with an emission peak at 520 nm and a full width at half maximum (FWHM) of 31 nm.

[0201] Figure 4 The image shows the photoluminescence spectrum of compound BN-60, with an emission peak at 520 nm and a full width at half maximum (FWHM) of 27 nm.

[0202] Examples of electroluminescent devices

[0203] 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:

[0204]

[0205]

[0206] The following are examples of electroluminescent devices fabricated using the materials of the present invention, and the specific device fabrication process is as follows:

[0207] Fabrication process of organic electroluminescent devices:

[0208] 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.

[0209] The preparation process is as follows:

[0210] (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.

[0211] (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 Sines 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].

[0212] (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].

[0213] (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 vapor 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

[0214] Device Example 1-n (n=51)

[0215] Organic electroluminescent devices (structures as shown in Device Examples 1-n (n = 1-51)) 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, H1-58 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 device effect embodiment is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 99wt%H1-58+1wt%BN-m(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0216] 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. Device performance testing was 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, device lifetime (T95, hours) refers to the device with an initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0217] Comparative device embodiments D1-n (n=1-16)

[0218] Organic electroluminescent devices (structures as shown in the comparative 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, H1-58 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-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 example is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 99wt%H1-58+1wt%Rm(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0219] Performance data for the comparative device examples are shown in Table D2. In Table D2, device lifetime (T95, hours) refers to the device's initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0220] Table 2

[0221]

[0222]

[0223] Table D2

[0224]

[0225]

[0226] Device Example 2-n (n = 1-51)

[0227] Organic electroluminescent devices (structure as shown in Device Examples 2-n (n = 1-51)) 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, H1-58+TRZ-4 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%H1-58+29wt%TRZ-4+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 3. In Table 3, the device lifetime (T95, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0229] Comparative device embodiment D2-n (n=1-16)

[0230] Organic electroluminescent devices (structure as shown in the comparative 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, H1-58+TRZ-4 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 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%H1-58+29wt%TRZ-4+1wt%Rm(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0231] The performance data of the comparative device examples are shown in Table D3. In Table D3, the device lifetime (T95, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0232] Table 3

[0233]

[0234]

[0235] Table D3

[0236]

[0237]

[0238] Device Examples 3-n (n = 1-51)

[0239] Organic electroluminescent devices (structure as shown in Device Examples 3-n (n = 1-51)) 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)].

[0240] Performance data for the device embodiments are shown in Table 4. In Table 4, the device lifetime (T95, hours) refers to the device's initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0241] Comparative device examples 3-n (n = 1-16)

[0242] Organic electroluminescent devices (structures as shown in Device Examples 3-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, H1-215+2CN-47 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 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%Rm(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0243] Performance data for the device embodiment are shown in Table D4. In Table D4, device lifetime (T95, hours) refers to the device's initial luminance of 1000 cd / m². 2When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0244] Table 4

[0245]

[0246]

[0247] Table D4

[0248]

[0249] Device Examples 4-n (n = 1-51)

[0250] Organic electroluminescent devices (structures as shown in Device Examples 1-n (n = 1-51)) 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, H1-215+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)].

[0251] Performance data for the device embodiments are shown in Table 5. In Table 5, the device lifetime (T95, hours) refers to the device's initial brightness of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0252] Comparative device examples 4-n (n = 1-16)

[0253] 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, Rm (m represents the last digit of the light-emitting material code used in the device embodiment) is used as the doped light-emitting material (doping concentration is 1wt%), TRZ-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%Rm(30nm) / TRZ-77(10nm) / TRZ-4(30nm)LiF(1nm) / Al(100nm)].

[0254] Performance data for the device embodiment are shown in Table D5. In Table D5, the device lifetime (T95, hours) refers to the device's initial luminance of 1000 cd / m². 2 When the brightness of the device drops to 95% of its initial brightness (i.e., the device brightness drops to 950 cd / m²), 2 The time required (in hours).

[0255] Table 5

[0256]

[0257]

[0258]

[0259] Table D5

[0260]

[0261] The organic electroluminescent device prepared by this invention achieves narrow-spectrum TADF emission, with the electroluminescence spectrum located in the green-red light region and a full width at half maximum (FWHM) of less than 45 nm. Furthermore, the device achieves a maximum external quantum efficiency of over 30% and a high lifetime.

[0262] The applicant declares that the present invention is illustrated by the above embodiments, but the present invention is not limited to the above process steps, that is, it does not mean that the present invention must rely on the above process steps 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: E 1 This indicates whether there are single-key links or not. E 2 E 3 and E 4 This indicates whether there are single-key links or not, and E 2 E 3 and E 4 One of them represents no single-key links, and the other two represent single-key links. R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 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 8 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 8 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; R 15 and R 16 It is H, deuterium, C1-C18 alkyl, C6-C18 aryl, or surrounded by one or more R a Substituted C6-C18 aryl, 5- to 24-membered heteroaryl, or substituted with one or more R a Substituted 5- to 18-membered heteroaryl groups; 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 8 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 8 R 9 R 10 R 11 R 12 R 13 and R 14 Independently, it is hydrogen, 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 8 R 9 R 10 R 11 R 12 R 13 and R 14 Independently hydrogen, methyl, 2-methyl-phenyl, Phenyl, The wavy lines represent the connection sites of the functional groups; Preferably, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them forms a ring structure with the connected aromatic ring as follows: The bond marked with an asterisk (*) is a bond shared with the aromatic ring.

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, The organic electroluminescent composition comprises, as a dopant material, a boron nitrogen 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 bonding 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 compounds 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 a boron-nitrogen compound as described in any one of claims 1-3; 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-136; 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-136; 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, R si (i = 7-39) Independently selected from any one of the following 5 groups: 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 main material is composed of any one of the compounds shown in formulas 2CN-1 to 2CN-60 and any one of the compounds shown in formulas H1-1 to H1-254; 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 host material is composed of any one of the dicyanophenyl derivatives shown in formulas 2CN-1 to 2CN-60 and any one of the carbazole derivatives shown in formulas H1-1 to H1-254; preferably, in the host 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-136, 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-128, 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 a phosphorescent compound containing metal Ir or Pt as shown in formulas Ir-1, Ir-2 and Pt-1; 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 or Pt 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 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 formula BN-1 to BN-136, and the main material is composed of any one of the carbazole or carboline derivatives shown in formula H1-1 to H1-254 and a phosphorescent compound containing metallic Ir shown in formula Ir-1 and Ir-2. Preferably, in the main material, the weight ratio between the carbazole or carboline derivatives shown in formula H1-1 to H1-254 and the phosphorescent compound 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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