A boron-nitrogen compound containing selenium and its use

Abstract

The present application provides a kind of selenium-containing boron-nitrogen compound and its application, the selenium-containing boron-nitrogen compound has the structure shown in formula I, the boron-nitrogen compound of the present application has luminescent property, as sensitizing agent material is used to prepare the light-emitting layer of organic electroluminescent device, and the organic electroluminescent device prepared thereby shows high efficiency and low efficiency roll-down.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology and relates to a sulfur-containing 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 photovoltaics (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.2 The green light emission of the device, with an efficiency of 1.5 lm / W (CWTang and S.A. Van Slyke, 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 He 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 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 light-emitting material, TADF materials have attracted widespread attention from industry due to their high efficiency and low cost, and related research has broad prospects.

[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 emission of fluorescent molecules, TADF emission primarily originates from transitions to the ICT state. Therefore, its excited-state lifetime is relatively long, leading to a rapid decrease in the efficiency of organic light-emitting devices based on TADF luminescent materials as the luminance increases—a phenomenon known as severe efficiency roll-off. Because of this severe efficiency roll-off, organic light-emitting devices with high luminance (≥1000 cd / m²) exhibit significant performance degradation. 2 The efficiency of the device is low, which will significantly increase the power consumption and stability of the device. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide a selenium-containing boron-nitrogen compound and its applications. The compound provided by this invention aims to solve the severe efficiency roll-off defect in organic electroluminescent devices based on TADF luminescent materials, providing a sensitizer material that achieves high efficiency at high brightness. This sensitizer material is used to prepare the luminescent layer of organic electroluminescent devices, resulting in high-performance organic electroluminescent devices.

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

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

[0009]

[0010] Indicates non-existence, single-key connection, An asterisk represents a bond site;

[0011] R 13 R 14 R 15 and R 16 Independently selected from H, deuterium, F, C1-C20 alkyl, C1-C20 alkoxy, C6-C24 aryl or, 5- to 24-heteroaryl;

[0012] R 13 R 14 R 15 and R 16 Independent existence or R 13 R 14 R 15 and R 16 At least one of them forms a ring with the connected aromatic ring;

[0013] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 Independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 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;

[0014] 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;

[0015] Rb 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;

[0016] 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;

[0017] 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;

[0018] R e Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl;

[0019] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 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 and R 12At least one of them forms a ring with the connected aromatic ring;

[0020] The alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl groups may be 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, in the selenium-containing boron nitrogen compound, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 Independently H, D (deuterium), C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, phenyl, with at least one C1-C 12 Alkyl-substituted aryl group, with at least one C1-C 12 Alkoxy-substituted aryl, 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 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.

[0023] Preferably, the R b 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.

[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 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 Independently, H, deuterium, 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 and R 12 Independently H, methyl, Phenyl, 2-methyl-phenyl

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

[0031] More preferably, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 H independently Phenyl, 2-methyl-phenyl The wavy lines represent the connection sites of the functional groups.

[0032] Preferably, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12When at least one of them forms a ring with the adjacent aromatic ring, the resulting ring has the following ring structure:

[0033] The * indicates a shared bond with the adjacent aromatic ring.

[0034] Preferably, R 13 R 14 R 15 and R 16 Independently selected from H, tert-butyl, phenyl or Preferably, Indicates non-existent, single-key connection, In some embodiments of the present invention, the selenium-containing boron nitrogen compound is any one of the following compounds:

[0035]

[0036]

[0037]

[0038]

[0039] On the other hand, the present invention provides an organic electroluminescent sensitizer material, wherein the organic electroluminescent sensitizer material comprises the selenium-containing boron nitrogen compound as described above.

[0040] 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 selenium-containing boron nitrogen compound as described above.

[0041] 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 selenium-containing boron nitrogen compound as described above.

[0042] In this invention, the boron-nitrogen compound having the structure shown in Formula I 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.

[0043] 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.

[0044] In one embodiment, the organic electroluminescent device has, for example... Figure 1The 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.

[0045] In one embodiment, the boron nitride compound having the structure shown in Formula I is used to prepare the light-emitting layer in an organic electroluminescent device.

[0046] 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.

[0047] On the other hand, the present invention provides an organic electroluminescent composition comprising, as described above, a selenium-containing boron nitrogen compound as a sensitizer material and a host material;

[0048] 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 sensitizer material.

[0049] In one embodiment, the organic electroluminescent composition comprises a host material, a sensitizer material, and a doped luminescent material; the sensitizer material in the organic electroluminescent composition is any one of the selenium-containing boron nitrogen compounds as described above; the doped luminescent material is some organic red or near-infrared fluorescent material (including thermally activated delayed fluorescence material) luminescent material (such as red material RD), whose emission peak is located at 615-750 nm and whose ultraviolet-visible absorption spectrum has an absorption peak in the 550-650 nm region;

[0050]

[0051] The main material is any one of the compounds shown in formula Trz1-A, Trz2-A or Trz3-A;

[0052]

[0053] Z is either N or CH;

[0054] Where R z1 As for R z10 Independently hydrogen, deuterium, F, CN, C1-C8 alkyl, C1-C8 alkoxy, C6-C 30 Aryl, R za Replacement C6-C 30Aryl, C6-C30 heteroaryl or R za β-substituted C6-C 30 Mixed aromatics;

[0055] R za It is a C1-C8 alkyl, C1-C8 alkoxy, C6-C 24 Aryl or C6-C 24 Mixed aromatics;

[0056] R z9 Or R z10 Aromatic rings, either independently or connected to them, form a ring.

[0057] Preferably, the organic electroluminescent composition contains 96.0 wt% to 70.0 wt% of the host material (e.g., 96 wt%, 94 wt%, 90 wt%, 85 wt%, 80 wt%, 75 wt%, 73 wt%, or 70 wt%), 3.0 wt% to 30.0 wt% of the sensitizer (e.g., 3 wt%, 5 wt%, 8 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt%, 25 wt%, 28 wt%, or 30 wt%), and 0.5 wt% to 5.0 wt% of the dopant material (e.g., 0.5 wt%, 0.8 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, or 5 wt%).

[0058] Preferably, the sensitizer material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-64, and the main material is composed of any one of the compounds shown in formula Trz1-A, Trz2-A or Trz3-A.

[0059] Preferably, the host material is at least one of the specific compounds shown in TRZ-1 to TRZ-48;

[0060]

[0061]

[0062]

[0063] Preferably, the sensitizer material in the organic electroluminescent composition is any one of the selenium-containing boron nitrogen compounds as described above, and the main material is composed of any one of the compounds shown in formulas TRZ-1 to TRZ-48.

[0064] Preferably, the sensitizer material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-64, and the main material is composed of any one of the compounds shown in formula TRZ-1 to TRZ-48.

[0065] On the other hand, the present invention provides an organic electroluminescent material comprising the organic electroluminescent composition as described above.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on the sensitization and energy transfer of the host material to any compound shown in Formula I.

[0071] 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.

[0072] 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.

[0073] Terminology Explanation

[0074] 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.

[0075] 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 “made of”.

[0076] Group definition

[0077] 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.

[0078] The section 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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).

[0086] As used herein, the term "alkoxy" refers to an alkyl group as defined above, which is connected via an oxygen bond (-O-).

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] The reagents and raw materials used in this invention are all commercially available.

[0093] Compared with the prior art, the present invention has the following beneficial effects:

[0094] The selenium-boron-nitrogen compounds of this invention, through extended conjugation and the introduction of different ligands, not only enable electroluminescent devices to achieve high luminous efficiency at high brightness but also significantly improve device stability. These selenium-boron-nitrogen compounds possess the property of sensitizing luminescent materials and can be used as sensitizers in the preparation of the luminescent layer of organic electroluminescent devices. The organic electroluminescent devices prepared thereby exhibit high efficiency at high brightness, reaching 1000 cd / m². 2 At a brightness of [insert value here], the external quantum efficiency of the device for electroluminescence is as high as 15% or more. Attached Figure Description

[0095] Figure 1 This is a schematic diagram of the structure of the vacuum evaporation type organic electroluminescent device provided by 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.

[0096] Figure 2 The photoluminescence spectrum of the device based on compound BN-1.

[0097] Figure 3 This is the absorption spectrum of RD.

[0098] Figure 4 The electroluminescence spectrum of the device based on compound BN-1 is shown. Detailed Implementation

[0099] 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.

[0100] In embodiments of the present invention, the raw materials used to synthesize the shown compounds are described below.

[0101] The raw materials used specifically include the following molecules:

[0102]

[0103] The synthesis methods for BN-1, BN-17, BN-21, BN-41, and BN-53 are the same. The synthetic route and specific details used in the experiment are illustrated using the synthesis example of compound BN-1:

[0104]

[0105] In the first step, under a nitrogen atmosphere, 55.8 g of 3,6-di-tert-butylcarbazole (A1) (200.0 mmol), 22.6 g of 1-bromo-3-chloro-2,4-difluorobenzene (100.0 mmol), and 97.8 g of cesium carbonate (300.0 mmol) were added to 800 mL of N,N-dimethylformamide. The mixture was bubbled with nitrogen for 10 minutes, then heated to 120 °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 and recrystallization to give a white solid intermediate M-1, in 91% yield.

[0106] In the second step, under a nitrogen atmosphere, 24.0 mL of a hexane solution of 2.5 M n-butyllithium (60.0 mmol) was slowly added to a 200 mL tetrahydrofuran solution (-30 °C) containing 37.3 g of intermediate M-1 (50.0 mmol), and the reaction was carried out at this temperature for 2 hours. Subsequently, a tetrahydrofuran solution of 10.8 g of 9-fluorenone (B1) (60.0 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 M-2 in 51% yield.

[0107] In the third step, under a nitrogen atmosphere, 30.8 mL of 1.3 M (40.0 mmol) hexane solution of tert-butyllithium was slowly added to 100 mL of tert-butylbenzene solution (-30°C) containing 16.6 g of intermediate M-2 (20.0 mmol). The mixture was slowly heated to 60°C and stirred for 2 hours, then cooled to -30°C, and 20.0 mmol of boron tribromide was added. The reaction mixture was stirred at room temperature for 1 hour. Next, N,N-diisopropylethylamine (40.0 mmol) was added at 0°C, and the reaction mixture was then heated to 150°C and stirred for 12 hours, followed by cooling to room temperature. The reaction system was concentrated under vacuum and purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give intermediate M-3 in 39% yield.

[0108] In the fourth step, under a nitrogen atmosphere, 4.0 g of intermediate M-2 (5.0 mmol), 64 mg of iodine granules (0.25 mmol), 395 mg of selenium powder (5.0 mmol), and 555 mg of selenium dioxide (5.0 mmol) were added to 50 mL of o-dichlorobenzene. The mixture was bubbled with nitrogen for 10 minutes, heated to 180 °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 and recrystallization to obtain the final product BN-7, with a yield of 57%.

[0109] The synthetic methods for BN-5, BN-7, BN-10, BN-11, BN-13, BN-15, BN-25, BN-27, BN-30, BN-32, BN-34, BN-36, BN-62, and BN-64 are the same. The synthetic route and specific details used in the experiment are illustrated by the example of the synthesis of compound BN-7.

[0110]

[0111] In the first step, under a nitrogen atmosphere, 27.9 g of starting material 3,6-di-tert-butylcarbazole (A1) (100.0 mmol), 22.6 g of starting material 1-bromo-3-chloro-2,4-difluorobenzene (100.0 mmol), and 48.9 g of cesium carbonate (150.0 mmol) were added to 800 mL of N,N-dimethylformamide. The mixture was bubbled with nitrogen for 10 minutes, then heated to 120 °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 and recrystallization to give a white solid intermediate M-1 in 65% yield.

[0112] In the second step, under a nitrogen atmosphere, 29.2 g of intermediate M-1 (60.0 mmol), 25.9 g of starting material A3 (60.0 mmol), and 29.3 g of cesium carbonate (90.0 mmol) were added to 400 mL of N,N-dimethylformamide. The mixture was bubbled with nitrogen for 10 minutes, then heated to 150 °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 and recrystallization to obtain a white solid intermediate M-2 in 90% yield.

[0113] In the third step, under a nitrogen atmosphere, 24.0 mL of a hexane solution of 2.5 M n-butyllithium (60.0 mmol) was slowly added to a 200 mL tetrahydrofuran solution (-30 °C) containing 44.9 g of intermediate M-2 (50.0 mmol), and the reaction was carried out at this temperature for 2 hours. Subsequently, a tetrahydrofuran solution of 10.8 g of 9-fluorenone (B1) (60.0 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 M-3 in 48% yield.

[0114] In the fourth step, under a nitrogen atmosphere, 30.8 mL of 1.3 M (40.0 mmol) hexane solution of tert-butyllithium was slowly added to 100 mL of tert-butylbenzene solution (-30°C) containing 19.6 g of intermediate M-3 (20.0 mmol). The mixture was slowly heated to 60°C and stirred for 2 hours, then cooled to -30°C, and 20.0 mmol of boron tribromide was added. The reaction mixture was stirred at room temperature for 1 hour. Next, N,N-diisopropylethylamine (40.0 mmol) was added at 0°C, and the reaction mixture was then heated to 150°C and stirred for 12 hours, followed by cooling 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 intermediate M-4 in 35% yield.

[0115] In the fifth step, under a nitrogen atmosphere, 5.16 g of intermediate M-4 (5.0 mmol), 64 mg of iodine granules (0.25 mmol), 395 mg of selenium powder (5.0 mmol), and 555 mg of selenium dioxide (5.0 mmol) were added to 50 mL of o-dichlorobenzene. The mixture was bubbled with nitrogen for 10 minutes, heated to 180 °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 and recrystallization to obtain the final product BN-7, with a yield of 53%.

[0116] The products were characterized using an Agilent Technologies Vario Micro Cube instrument for elemental analysis, testing for C, H, and N. Mass spectrometry was performed using a Thermo Fisher TSQ Endura ultra-high performance liquid chromatography-tandem triple quadrupole mass spectrometer (USA), and relevant data are shown in Table H1.

[0117] Table H1

[0118]

[0119] Figure 2 The photoluminescence spectrum of BN-1 is shown, with an emission peak at 607 nm.

[0120] Examples of electroluminescent devices

[0121] The following are some representative examples of electroluminescent devices. The molecular structures of some materials involved in the device examples and comparative examples are as follows:

[0122]

[0123]

[0124] Figure 3 The absorption spectrum of RD shows an absorption peak at 616 nm.

[0125] The following are examples of electroluminescent devices fabricated using the materials of the present invention, and the specific device fabrication process is as follows:

[0126] Fabrication process of organic electroluminescent devices:

[0127] The structure of the device is 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.

[0128] The preparation process is as follows:

[0129] (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.

[0130] (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].

[0131] (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].

[0132] (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

[0133] Device Example Sn (n = 1-19)

[0134] Organic electroluminescent devices (structures as shown in the device embodiment Sn (n = 1-19)) 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, TRZ-45 is used as the host material in the light-emitting layer, the selenium-boron-nitrogen compound BN-n described in this invention is used as the sensitizer material (doping concentration of 15wt%), RD is used as the doped light-emitting material (doping concentration of 1wt%), ET-2 is used as the second electron transport layer, ET-1 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the example is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 84wt%TRZ-45+15wt%BN-n+1wt%RD(30nm) / ET-1(10nm) / ETL-1(30nm)LiF(1nm) / Al(100nm)].

[0135] Performance data for the device embodiments are shown in Table 1. The device's current, voltage, luminance, and emission spectrum characteristics were simultaneously tested using a Photo Research PR 655 spectral scanning luminance meter and a Keithley K 2400 digital source meter system. 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).

[0136] Comparative Device Example R

[0137] The organic electroluminescent device in comparative device embodiment R (structure as shown) 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, TRZ-45 is used as the host material in the light-emitting layer, RD is used as the doped light-emitting material (doping concentration is 1wt%), ET-2 is used as the second electron transport layer, ET-1 is used as the first electron transport layer, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the example is [ITO / 15wt%HIM+85wt%HTL-1(100nm) / HTL-2(10nm) / 99wt%TRZ-45+1wt%Rm(30nm) / ET-2(10nm) / ET-1(30nm)LiF(1nm) / Al(100nm)].

[0138] Performance data for the comparative device embodiments are shown in Table R1.

[0139] Figure 4 The electroluminescence spectrum of the device using compound BN-1 as a sensitizer is shown, with an emission peak at 648 nm and a full width at half maximum (FWHM) of 47 nm.

[0140] Table 1

[0141]

[0142] Table R1

[0143]

[0144] The applicant declares that this invention illustrates the application of the selenium-containing boron nitrogen compound and its sensitizer in electroluminescent devices through the above embodiments, but this invention is not limited to the above embodiments, that is, it does not mean that this invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of the raw materials used in this invention, additions of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. A selenium-containing boron-nitrogen compound, characterized in that, The selenium-containing boron nitride luminescent material has the structure shown in Formula I: Indicates non-existent, single-key connection, An asterisk represents a bond site; R 13 R 14 R 15 and R 16 Independently selected from H, deuterium, F, C1-C20 alkyl, C1-C20 alkoxy, C6-C24 aryl or, 5- to 24-heteroaryl; R 13 R 14 R 15 and R 16 Independent existence or R 13 R 14 R 15 and R 16 At least one of them forms a ring with the connected aromatic ring; R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 Independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 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 and R 12 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 and R 12 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 selenium-containing 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 and R 12 Independently H, D (deuterium), C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, phenyl, with at least one C1-C 12 Alkyl-substituted aryl group, with at least one C1-C 12 Alkoxy-substituted aryl, 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 and R 12 Independently, H, deuterium, 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 and R 12 Independently H, methyl, Phenyl, 2-methyl-phenyl The wavy lines represent the connection sites of the functional groups; More preferably, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 and R 12 H independently Phenyl, 2-methyl-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 and R 12 When at least one of them forms a ring with the adjacent aromatic ring, the resulting ring has the following ring structure: The * indicates a shared bond with the adjacent aromatic ring. Preferably, R 13 R 14 R 15 and R 16 Independently selected from H, tert-butyl, phenyl or Preferably, Indicates non-existent, single-key connection, 3. The selenium-containing boron nitrogen compound according to claim 1 or 2, characterized in that, The selenium-containing boron nitrogen compound is any one of the following compounds:

4. An organic electroluminescent composition, characterized in that, It includes a selenium-containing boron nitrogen compound as a sensitizing material as described in any one of claims 1-3 and a host material; 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 sensitizing material.

5. The organic electroluminescent composition according to claim 4, characterized in that, The organic electroluminescent composition comprises a host material, a sensitizer material, and a doped luminescent material; the sensitizer material in the organic electroluminescent composition is any one of the selenium-containing boron nitrogen compounds according to any one of claims 1-3; Preferably, the doped luminescent material is an organic red or near-infrared fluorescent material with an emission peak at 615-750 nm and an absorption peak in the 550-650 nm region in the ultraviolet-visible absorption spectrum. Preferably, the host material is any one of the compounds represented by formula Trz1-A, Trz2-A or Trz3-A; Z is either N or CH; Where R z1 As for R z10 Independently hydrogen, deuterium, F, CN, C1-C8 alkyl, C1-C8 alkoxy, C6-C 30 Aryl, R za Replacement C6-C 30 Aryl, C6-C30 heteroaryl or R za β-substituted C6-C 30 Mixed aromatics; R za It is a C1-C8 alkyl, C1-C8 alkoxy, C6-C 24 Aryl or C6-C 24 Mixed aromatics; R z9 or R z10 Aromatic rings, either independently or connected to them, form a ring; Preferably, the organic electroluminescent composition contains 96.0 wt%-70.0 wt% of the main material, 3.0 wt%-30.0 wt% of the sensitizer, and 0.5 wt%-5.0 wt% of the dopant material. Preferably, the sensitizer material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-64, and the main material is composed of any one of the compounds shown in formula Trz1-A, Trz2-A or Trz3-A. Preferably, the host material is any one of the specific compounds shown in TRZ-1 to TRZ-48; Preferably, the sensitizer material in the organic electroluminescent composition is any one of the compounds in any one of claims 1-3, and the main material is composed of any one of the compounds shown in formulas TRZ-1 to TRZ-48; Preferably, the sensitizer material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-64, and the main material is composed of any one of the compounds shown in formula TRZ-1 to TRZ-48.

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

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises 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 selenium-containing 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 selenium-containing boron nitrogen 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 selenium-containing boron nitrogen compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claims 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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