Boron-nitrogen compound and organic electroluminescent device using same

Abstract

The invention discloses a boron-nitrogen compound and an organic electroluminescent device using the same, and relates to the technical field of organic electroluminescence. According to the boron-nitrogen compound provided by the invention, spiro and electron donor groups are introduced, so that the reverse intersystem crossing rate of molecules is favorably improved, triplet state exciton quenching is overcome, intermolecular close packing is effectively inhibited, the problem of spectrum broadening under high doping concentration is relieved, and the color purity of a device is improved; the compound is applied to a luminescent layer doping material of an organic electroluminescent device, so that the stability of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more specifically to a boron-nitrogen compound and an organic electroluminescent device using the compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of high brightness, wide range of material selection, low driving voltage, and active light emission. They also have advantages such as high definition, wide viewing angle, and fast response speed, making them a hot research area in the last ten years or so.

[0003] In 1987, CWTang et al. developed devices composed of various functional materials stacked together, thus putting organic electroluminescent devices using organic materials into practical applications. A typical OLED can have the following structure: an anode is formed on the upper part of the substrate, and a hole transport region, an emissive layer, an electron transport region, and a cathode are sequentially formed on the upper part of the anode.

[0004] The luminescent material in the emissive layer is the core functional material of OLED devices, directly determining key performance characteristics such as luminous efficiency, color purity, and lifetime. In recent years, multiple resonance thermally activated delayed fluorescence (MR-TADF) materials have shown great potential for achieving high-efficiency, high-color-purity OLEDs due to their high luminous efficiency and narrow emission half-width. However, limited by their rigid planar structure and the distribution of molecular orbitals at the atomic localization frontier, most reported MR-TADF molecules still face severe molecular aggregation and triplet exciton quenching, greatly restricting further improvements in device performance and hindering the commercialization of MR-TADF materials. Therefore, suppressing the aggregation of MR-TADF molecules and triplet exciton quenching has become a key scientific challenge in achieving high-color-purity, high-efficiency, and high-stability MR-TADF OLED devices. Summary of the Invention

[0005] To address the aforementioned problems, the present invention aims to provide a boron-nitrogen compound and an organic electroluminescent device using the compound, which can improve the luminous efficiency and stability of the organic electroluminescent device.

[0006] This invention provides a boron-nitrogen compound, wherein the boron-nitrogen compound is selected from the structure shown in Formula 1:

[0007]

[0008] The M is selected from the structure shown in Equation 1-1, Equation 1-2, or Equation 1-3.

[0009]

[0010] The X4 is selected from single bonds, O, S, CRdRe, and NRf;

[0011] The Rd and Re are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rd and Re are interconnected to form substituted or unsubstituted rings;

[0012] The Rf and R are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0013] Ar1 and Ar2 are each independently selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring;

[0014] X1 and X2 are each independently selected from none, single bond, O, S, Se, CRaRb, SiRaRb, GeRaRb, NRc, and at least one of X1 and X2 is selected from O, S, Se, CRaRb, SiRaRb, GeRaRb or NRc;

[0015] The X3 is selected from single bonds, O, S, Se, CRgRh, SiRgRh, GeRgRh, or NRi;

[0016] Ra and Rb are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Ra and Rb are interconnected to form substituted or unsubstituted rings.

[0017] The Rg and Rh are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rg and Rh are interconnected to form substituted or unsubstituted rings.

[0018] Rc and Ri are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0019] Each of the terms 'a' is independently selected from CR1 or N;

[0020] Each of the R1s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl, deuterium, tritium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1, C1, C2, C2, C2, C2, C2, C3 ...

[0021] Each of the b's is independently selected from CR2 or N;

[0022] Each of the R2s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R2s are connected to form a substituted or unsubstituted ring;

[0023] Each of the c's is independently selected from CR0 or N;

[0024] Each of the R0s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R0s are connected to form substituted or unsubstituted rings.

[0025] Each of the d is independently selected from CR4 or N, and the d connected to M is selected from C;

[0026] Each of the R4s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R4s are connected to form substituted or unsubstituted rings.

[0027] Each of the e is independently selected from CR3 or N;

[0028] Each of the R3s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 fused cycloalcoholic group ...

[0029] L1 and L2 are each independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring.

[0030] The asterisk (*) indicates a connection point.

[0031] The present invention also provides an organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the organic layer is disposed between the cathode and the anode, and the organic layer comprises a light-emitting layer comprising at least one or more of the boron nitrogen compounds described in the present invention.

[0032] Beneficial effects

[0033] The boron-nitrogen compound provided by this invention introduces spirocyclic rings and electron donor groups into the rigid structure of boron-nitrogen, which not only helps to increase the reverse intersystem crossing rate of MR-TADF molecules and overcome triplet exciton quenching, but also effectively suppresses close packing between molecules, alleviates the problem of spectral broadening at high doping concentrations, and improves the color purity of the device. When applied to organic electroluminescent devices, it can improve the stability of the device and extend its service life. Detailed Implementation

[0034] Before providing a detailed description of the invention, it should be understood that the terminology used in this specification is for describing specific embodiments only and is not intended to limit the scope of the invention. The scope of the invention should be defined only by the scope of the appended claims. Unless otherwise expressly stated, all technical and scientific terms used in this specification have the same meaning as commonly understood by one of ordinary skill in the art.

[0035] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0036] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0037] In the specification, "*-" can be attached to any optional position of the group / fraction to which it is attached. For example express And so on.

[0038] In the specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent And so on.

[0039] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0040] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. Examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, etc., but are not limited thereto.

[0041] The silyl group referred to in this invention is a -Si(R)3 group, wherein each R is the same or different and is selected from any of the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring. Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, halogen, nitro, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, vinyl, propynyl, 1,3-butadienyl, ethynyl, propynyl, butynyl, methoxy, ethoxy, propoxy, phenoxy, 1-naphthoxy, 9-anthraoxy, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, tetrahydronaphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0042] The cycloalkyl group described in this invention refers to a monovalent group in a cyclic alkane molecule after removing one hydrogen atom, preferably having 3 to 20 carbon atoms, more preferably having 3 to 12 carbon atoms, and particularly preferably having 3 to 6 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto.

[0043] The alkoxy group described in this invention is represented by -O-alkyl and can be a straight-chain alkoxy group or a linear alkoxy group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. Specific examples may include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, isobutoxy, 2-methylbutoxy, 3-methylbutoxy, 2-ethylhexoxy, etc., but are not limited thereto.

[0044] The alkenyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited thereto.

[0045] The alkynyl group mentioned in this invention refers to a monovalent group in an alkyne molecule after removing one hydrogen atom. It can be a straight-chain alkynyl group or a branched-chain alkynyl group, preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include ethynyl, 1-propynyl, 1-butynyl, 1-pentynyl, 1-hexynyl, 1-heptyynyl, 1-octyynyl, 1-nonynyl, 1-decynyl, 2-butynyl, 3-methyl-1-butynyl, 4-methyl-2-pentynyl, phenylethynyl, 1-phenyl-2-propynyl, 3-phenyl-1-propynyl, 2-naphthylethynyl, 1-naphthylethynyl, diphenylethynyl, 1-benzocyclobutenylethynyl, 2-biphenylethynyl, 9-phenanthylethynyl, 2-anthraylethynyl, 2-thienylethynyl, 3-pyridylethynyl, 2-furanylethynyl, etc., but are not limited to these.

[0046] The aryloxy group described in this invention is represented by -O-aryl. The aromatic hydrocarbon portion of the aryloxy group includes monocyclic aromatic hydrocarbons, polycyclic aromatic hydrocarbons, fused-ring aromatic hydrocarbons, and heterocyclic aromatic hydrocarbons, etc., preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 14 carbon atoms. Specific examples may include phenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy, 2-ethylphenoxy, 3-ethylphenoxy, 4-ethylphenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-methoxyphenoxy, 4-ethoxyphenoxy, biphenyl-2-oxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthoxy, 2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 9-phenanthoxy, 2-furanoxy, 3-furanoxy, 2 -Thiophenoxy, 3-thiophenoxy, 2-pyridinoxy, 3-pyridinoxy, 4-pyridinoxy, 2-quinolinoxy, 3-quinolinoxy, 4-quinolinoxy, 8-quinolinoxy, 2-benzofuranoxy, 2-benzothiophenoxy, benzyloxy, 2-phenylethoxy, 3-phenylpropoxy, 4-phenylbutoxy, 1-naphthylmethyloxy, 2-naphthylmethyloxy, 9-anthracitemethyloxy, 4-methylbenzyloxy, 4-methoxybenzyloxy, 4-chlorobenzyloxy, 4-nitrobenzyloxy, etc., but not limited to these.

[0047] The aryl group described in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Specific examples may include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, anthracene, phenanthryl, pyrene, triphenylene, perylene, 1-phenylnaphthyl, 2-phenylnaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, spirofluorenoxanthyl, spirofluorenthixanthyl, etc., but are not limited thereto.

[0048] The heteroaryl group described in this invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, o-phenanthrolinel, naphridyl, indoleyl, benzothiopheneyl, benzofuranyl, N-hexabenzothiopheneyl, N-hexabenzofuran. The following are examples of compounds, but not limited to: benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, N-hexabenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, N-hexabenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, N-hexacarbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethionthanthraceneyl, etc.

[0049] The aliphatic and aromatic ring fused cyclic groups mentioned in this invention refer to the general term for divalent groups formed by removing two hydrogen atoms after an aromatic ring and an aliphatic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Specific examples may include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited to these.

[0050] The sub-fused cyclic groups of aliphatic and heteroaromatic rings mentioned in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused aliphatic and heteroaromatic rings. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The aliphatic ring preferably has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Specific examples may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc., but are not limited thereto.

[0051] In the invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not replaced by a non-hydrogen group.

[0052] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroaryl," refers to being independently monosubstituted or polysubstituted by the following groups: hydrogen, deuterium, tritium, nitro, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted... Substituted C2-C20 alkynyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcohol groups of substituted or unsubstituted C3-C20 aliphatic rings and C6-C30 aromatic rings, fused cycloalcohol groups of substituted or unsubstituted C3-C20 aliphatic rings and C2-C30 heteroaromatic rings, etc., but not limited to these. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, anthracene, phenanthrene, triphenylene. Phenyl, peryl, pyrene, benzyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, etc., but not limited to these.

[0053] The "linked ring" described in this invention refers to two groups linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0054] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, benzocyclopentane, cyclohexene, cyclohexane, benzocyclohexane, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0055] This invention provides a boron-nitrogen compound, wherein the boron-nitrogen compound is selected from the structure shown in Formula 1:

[0056]

[0057] The M is selected from the structure shown in Equation 1-1, Equation 1-2, or Equation 1-3.

[0058]

[0059] The X4 is selected from single bonds, O, S, CRdRe, and NRf;

[0060] The Rd and Re are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rd and Re are interconnected to form substituted or unsubstituted rings;

[0061] The Rf and R are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0062] Ar1 and Ar2 are each independently selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring;

[0063] X1 and X2 are each independently selected from none, single bond, O, S, Se, CRaRb, SiRaRb, GeRaRb, NRc, and at least one of X1 and X2 is selected from O, S, Se, CRaRb, SiRaRb, GeRaRb or NRc;

[0064] The X3 is selected from single bonds, O, S, Se, CRgRh, SiRgRh, GeRgRh, or NRi;

[0065] Ra and Rb are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Ra and Rb are interconnected to form substituted or unsubstituted rings.

[0066] The Rg and Rh are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rg and Rh are interconnected to form substituted or unsubstituted rings.

[0067] Rc and Ri are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0068] Each of the terms 'a' is independently selected from CR1 or N;

[0069] Each of the R1s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl, deuterium, tritium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1, C1, C2, C2, C2, C2, C2, C3 ...

[0070] Each of the b's is independently selected from CR2 or N;

[0071] Each of the R2s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R2s are connected to form a substituted or unsubstituted ring;

[0072] Each of the c's is independently selected from CR0 or N;

[0073] Each of the R0s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R0s are connected to form substituted or unsubstituted rings.

[0074] Each of the d is independently selected from CR4 or N, and the d connected to M is selected from C;

[0075] Each of the R4s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R4s are connected to form substituted or unsubstituted rings.

[0076] Each of the e is independently selected from CR3 or N;

[0077] Each of the R3s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 fused cycloalcoholic group ...

[0078] L1 and L2 are each independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring.

[0079] The asterisk (*) indicates a connection point.

[0080] Preferably, the boron-nitrogen compound is selected from any one of the structures shown in Formula 2-1 to Formula 2-3.

[0081]

[0082] The definitions of X1, X2, X3, X4, a, b, c, d, e, R, Ar1, Ar2, L1, and L2 are the same as those in Equation 1.

[0083] Preferably, R is selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, triphenylsilyl, and tripyridylsilane. Cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornel, adamantyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, phenoxy, methylphenoxy, ethylphenoxy, biphenoxy, naphthoxy, anthraquinone, phenoxy, phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenytoyl, phenylene, 9,9-dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinocyclobutane, pyridinocyclopentane, pyridinocyclohexane, pyridinocycloheptane, pyridinocyclopentenyl, pyridinocyclopentenyl Cyclohexenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthraceneyl, deuterated phenanthryl, deuterated triphenylene, deuterated furanyl, deuterated benzofuranyl, deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzyl Thiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoro The following is a list of methyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, and deuterated tert-butyl-substituted biphenyl.

[0084] Ar1 and Ar2 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, phenyl Biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinylcyclobutane, pyridinylcyclopentane, pyridinylcyclohexane, pyridinylcycloheptane, pyridinylcyclopentenyl, pyridinylcyclohexenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornelyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthraceneyl, deuterated phenanthryl, deuterated triphenylene, deuterated furanyl, deuterated benzofuranyl, deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzothiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl The substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl.

[0085] L1 and L2 are each independently selected from single bonds, phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9-methyl-9-phenylfluorene, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclocyclo Hexylene, benzocycloheptanylene, pyridinoid cyclobutylene, pyridinoid cyclopentylene, pyridinoid cyclohexylene, pyridinoid cycloheptanylene, pyridinoid cyclopentenylene, deuterated methylene, deuterated ethylene, deuterated n-propylene, deuterated isopropylene, deuterated n-butylene, deuterated isobutylene, deuterated sec-butylene, deuterated tert-butylene, deuterated phenylene, deuterated biphenylene, deuterated terphenylene, deuterated naphthylene, deuterated anthraceneylene, deuterated phenanthrene, deuterated triphenylene, deuterated furanylene, deuterated benzofuranylene, deuterated Deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzothiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenylene, fluorinated biphenylene, cyano-substituted phenylene, cyano-substituted biphenylene, methyl-substituted phenylene, methyl-substituted biphenylene, ethyl-substituted phenylene, ethyl-substituted biphenylene, isopropyl-substituted phenylene, isopropyl-substituted biphenylene, tert-butyl-substituted phenylene, tert-butyl-substituted phenylene The following are all of the following: butyl-substituted biphenylene, trifluoromethyl-substituted biphenylene, trifluoromethyl-substituted biphenylene, adamantyl-substituted biphenylene, adamantyl-substituted biphenylene, norbornyl-substituted biphenylene, norbornyl-substituted biphenylene, methyl-substituted naphthylene, ethyl-substituted naphthylene, isopropyl-substituted naphthylene, tert-butyl-substituted naphthylene, deuterated methyl-substituted biphenylene, deuterated methyl-substituted biphenylene, deuterated isopropyl-substituted biphenylene, deuterated tert-butyl-substituted biphenylene, and deuterated tert-butyl-substituted biphenylene.

[0086] Preferably, the boron-nitrogen compound is selected from any one of the structures shown in Formulas 3-1 to 3-5.

[0087]

[0088] The X5 is selected from O, S, Se, CRaRb, SiRaRb, GeRaRb or NRc;

[0089] The definitions of X3, M, a, b, c, d, Ra, Rb, and Rc are the same as those in Equation 1.

[0090] Preferably, Ra, Rb, and Rc are each independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenyl ... Pyridylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, adamantyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, phenoxy, methylphenoxy, ethylphenoxy, biphenyloxy, naphthoxy, anthraquinoneoxy, phenoxy, phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthrene, 9,9-dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinocyclobutane, pyridinocyclopentane, pyridinocyclohexane, pyridinocycloheptane, pyridinocyclopentenyl, pyridinocyclopentenyl Cyclohexenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthraceneyl, deuterated phenanthryl, deuterated triphenylene, deuterated furanyl, deuterated benzofuranyl, deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzyl Thiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoro The following is a list of methyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, and deuterated tert-butyl-substituted biphenyl.

[0091] More preferably, the boron-nitrogen compound is selected from those shown in Formulas 4-1 to 4-15.

[0092]

[0093]

[0094] a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2 or 3.

[0095] Preferably, the formula Selected from any one of the following groups,

[0096]

[0097]

[0098] The definitions of R, R3, Rd, Re, Rf, and L1 are the same as those in Equation 1;

[0099] b1 is selected from 0, 1, 2, 3 or 4; b2 is selected from 0, 1, 2 or 3; b3 is selected from 0, 1 or 2; b4 is selected from 0 or 1.

[0100] Preferably, the formula Selected from any one of the following groups,

[0101]

[0102]

[0103] The definitions of R3, Rd, Re, Rf, and L1 are the same as those in Equation 1;

[0104] c1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c3 is selected from 0, 1, 2, 3, 4, 5 or 6; c4 is selected from 0, 1, 2, 3, 4 or 5.

[0105] Preferably, Rd, Re, and Rf are each independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenyl ... Pyridylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, adamantyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, phenoxy, methylphenoxy, ethylphenoxy, biphenyloxy, naphthoxy, anthraquinoneoxy, phenoxy, phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthrene, 9,9-dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinocyclobutane, pyridinocyclopentane, pyridinocyclohexane, pyridinocycloheptane, pyridinocyclopentenyl, pyridinocyclopentenyl Cyclohexenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthraceneyl, deuterated phenanthryl, deuterated triphenylene, deuterated furanyl, deuterated benzofuranyl, deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzyl Thiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoro The following is a list of methyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, and deuterated tert-butyl-substituted biphenyl.

[0106] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or any one of the following groups:

[0107]

[0108] The X6 is selected from O, S, CR6R7, NR5, SiR6R7, GeR6R7 or Se;

[0109] The Y is selected from CR8 or N;

[0110] R5 and R8 are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0111] R6 and R7 are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R6 and R7 are interconnected to form substituted or unsubstituted rings.

[0112] The ring A is selected from substituted or unsubstituted C3 to C20 aliphatic rings;

[0113] Each of the v values ​​is independently selected from CR9 or N;

[0114] Each of the R9s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted R9s connected to form substituted or unsubstituted rings.

[0115] Preferably, at most two or at most one v in each group is selected from N.

[0116] Preferably, L1 and L2 are each independently selected from single bonds or any one of the following groups:

[0117]

[0118] The X7 is selected from O, S, and CR. 10 R 11 NR 12 SiR 10 R 11 GeR 10 R 11 Or Se;

[0119] The Q is selected from CR 13 Or N;

[0120] The R 12 R 13 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring;

[0121] The R 10 R 11 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R 10 R 11 They connect to each other to form substituted or unsubstituted rings;

[0122] The ring B is selected from substituted or unsubstituted C3 to C20 aliphatic rings;

[0123] The n is selected from CR 14 Or N;

[0124] The R 14 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R 14 They connect to form substituted or unsubstituted rings.

[0125] Preferably, at most two or at most one n in each group is selected from N.

[0126] Preferably, R0, R1, R2, and R4 are each independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenyl ... Pyridylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, adamantyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, phenoxy, methylphenoxy, ethylphenoxy, biphenyloxy, naphthoxy, anthraquinoneoxy, phenoxy, phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthrene, 9,9-dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinocyclobutane, pyridinocyclopentane, pyridinocyclohexane, pyridinocycloheptane, pyridinocyclopentenyl, pyridinocyclopentenyl Cyclohexenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthraceneyl, deuterated phenanthryl, deuterated triphenylene, deuterated furanyl, deuterated benzofuranyl, deuterated dibenzofuranyl, deuterated thiopheneyl, deuterated benzyl Thiopheneyl, deuterated dibenzothiopheneyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoro The following is a list of methyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, and deuterated tert-butyl-substituted biphenyl.

[0127] Preferably, adjacent R0s are interconnected to form any one of the following: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, indene ring, pyridine ring, pyrimidine ring, indole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, oxazole ring, and thiazole ring.

[0128] Preferably, adjacent R1s are interconnected to form any one of the following: benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, triphenylene ring, indene ring, pyridine ring, pyrimidine ring, indole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, oxazole ring, and thiazole ring.

[0129] Preferably, adjacent R2 rings are interconnected to form any one of the following: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, indene ring, pyridine ring, pyrimidine ring, indole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, oxazole ring, and thiazole ring.

[0130] Preferably, adjacent R4 rings are interconnected to form any one of the following: benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, triphenylene ring, indene ring, pyridine ring, pyrimidine ring, indole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, oxazole ring, and thiazole ring.

[0131] Most preferably, the boron-nitrogen compound is selected from any one of the following structures:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] The above lists some specific structural forms of the compounds of Formula 1 described in this invention. However, this invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1, with substituents as defined above, should be included.

[0161] The main reaction types involved in this invention are the Suzuki coupling reaction and the Buchwald–Hartwig coupling reaction. The amounts of each substance used are those used in a single coupling reaction.

[0162] Furthermore, the present invention also provides an organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the organic layer is disposed between the cathode and the anode, and the organic layer comprises a light-emitting layer comprising at least one or more of the boron nitrogen compounds.

[0163] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material comprises at least one or more of the boron nitride compounds.

[0164] Specifically, the organic layer includes, but is not limited to, a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a light-emitting auxiliary layer.

[0165] As the anode of the present invention, a transmission electrode, a reflection electrode, or a semi-transmission electrode can be selected. When the anode is a transmission electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the anode is a semi-transmission electrode or a reflection electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0166] As the hole injection layer of the present invention, a material with good hole-accepting ability is preferred. Specific examples include, but are not limited to, metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrene compounds, quinacridones, perylene compounds, etc.

[0167] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Specific examples may include, but are not limited to, materials such as diphenylamine compounds, fluorene compounds, carbazole compounds, and benzidine compounds.

[0168] The light-emitting layer material described in this invention typically contains a dopant material and a host material. The dopant material uses a boron-nitrogen compound as shown in Formula 1 of this invention. The host material of the light-emitting layer not only needs to possess bipolar charge transport properties, but also needs appropriate energy levels to effectively transfer excitation energy to the dopant material.

[0169] The main material can include a single main material or two main materials.

[0170] The dual-body material may include a first body material and a second body material, and preferably at least one of the first body material and the second body material is a TADF material.

[0171] TADF materials refer to materials exhibiting thermally activated delayed fluorescence (TADF). TADF is a process of thermally activated re-emission of triplet excitons; that is, after thermal activation, the triplet exciton transitions to a higher vibrational energy level, then reaches a singlet vibrational energy level close to it via anti-intersystem crossing, and then emits fluorescence. Therefore, both singlet and triplet excitons generated can be utilized simultaneously in a device, allowing the exciton utilization rate of electroinduced excitons within the device to be as close to 100% as possible. Compared to traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0172] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0173] Exciton-sensitized materials may play functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron nitride compound shown in Formula 1 of this invention, when used in combination with the exciton-sensitized material, has a significant effect on improving device efficiency, exciton annihilation in the device, and efficiency reduction.

[0174] As the electron transport layer material of the present invention, materials with high electron mobility are preferred. Specific examples may include, but are not limited to, quinoline compounds, imidazole compounds, o-phenanthroline compounds, triazole compounds, metal chelates, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, benzimidazole compounds, etc.

[0175] As the electron injection layer material of the present invention, a material with a low work function is preferred. Specific examples may include: metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, etc. Examples may include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0176] As the cathode of the present invention, a transmission electrode, a semi-reflective electrode, or a reflective electrode can be selected. When the cathode is a transmission electrode, the cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the cathode material can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0177] The organic layer of the aforementioned organic electroluminescent device can be deposited by vacuum deposition, spin coating, casting, Langmuir-Brønder (LB) method, etc. When using vacuum deposition, the vacuum deposition conditions vary depending on the compound.

[0178] The fabrication of the above-described organic electroluminescent device is specifically described in the following embodiments. However, the following embodiments are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.

[0179] Preparation and characterization of compounds

[0180] Description of raw materials, reagents, and characterization equipment:

[0181] The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0182] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0183] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0184] [Synthetic Example 1] Preparation of intermediate D-11:

[0185]

[0186] Under nitrogen protection, a-11 (77.73 g, 300.00 mmol), b-11 (50.77 g, 300.00 mmol), sodium tert-butoxide (57.66 g, 600.00 mmol), 1500 mL of toluene, Pd(OAc)₂ (0.67 g, 3.00 mmol), and tri-tert-butylphosphine (0.61 g, 3.00 mmol) were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then purified by silica gel column chromatography (dichloromethane:n-hexane = 1:5) to give intermediate D-11 (82.34 g, yield 79%); HPLC analysis showed that the solid purity was ≥99.79%. Mass spectrometry m / z: 347.1326 (theoretical value: 347.1310).

[0187] By substituting the raw materials accordingly, intermediate D can be prepared according to the preparation method of intermediate D-11 in Synthesis Example 1. The raw materials are shown in the table below:

[0188]

[0189]

[0190] [Synthetic Example 2] Preparation of intermediate D-81:

[0191] Under nitrogen protection, a-11 (77.73 g, 300.00 mmol), c-81 (86.14 g, 300.00 mmol), K2CO3 (62.19 g, 450.00 mmol), Pd(PPh3)4 (3.47 g, 3.00 mmol), and 1500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at an 8:1 ratio to give intermediate D-81 (94.84 g, yield 75%). HPLC analysis showed that the purity of the solid was ≥99.73%. Mass spectrometry m / z: 421.1481 (theoretical value: 421.1467).

[0192] By substituting the raw materials accordingly, intermediate D can be prepared according to the preparation method of intermediate D-81 in Synthesis Example 2. The raw materials are shown in the table below:

[0193]

[0194]

[0195] [Synthetic Example 3] Preparation of Compound 11:

[0196]

[0197] Preparation of intermediate C-11:

[0198] Under a nitrogen atmosphere, compound A-11 (98.51 g, 350.00 mmol) and cesium carbonate (228.07 g, 700.00 mmol) were dissolved in 17500 mL of anhydrous DMF solution and stirred for 20 min. Then, compound B-11 (117.37 g, 350.00 mmol) was added, and the mixture was heated to 150 °C for 12 hours and then cooled to room temperature. The reagents were removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 650 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography. The eluent (petroleum ether: dichloromethane = 4:1) gave intermediate C-11 (156.65 g, yield 75%). HPLC analysis showed a solid purity ≥99.69%. Mass spectrometry m / z: 595.0127 (theoretical value: 595.0138).

[0199] Preparation of intermediate E-11:

[0200] Under a nitrogen atmosphere, intermediate C-11 (149.19 g, 250.00 mmol) was dissolved in 500 mL of dry THF, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 312 mL) was added. The reaction was carried out at this temperature for 1 h. Compound D-11 (86.85 g, 250.00 mmol) was dissolved in 1875 mL of dry THF pre-cooled to -78 °C. This solution was then slowly injected into the solution of intermediate C-11 at -78 °C, and the temperature was slowly raised to room temperature for 12 h. After the reaction was completed, a small amount of methanol was added to quench the reaction, the solvent was evaporated under reduced pressure, 4690 mL of glacial acetic acid and 469 mL of concentrated hydrochloric acid were added, and the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with saturated sodium carbonate aqueous solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:dichloromethane in a 5:1 eluent to give intermediate E-11 (146.05 g, yield 73%). HPLC analysis showed a solid purity ≥99.74%. Mass spectrometry m / z: 798.2389 (theoretical value: 798.2376).

[0201] Preparation of intermediate G-11:

[0202] Under a nitrogen atmosphere, intermediate E-11 (120.04 g, 150.00 mmol), compound F-11 (27.48 g, 150.00 mmol), Pd2(dba)3 (2.75 g, 3.00 mmol), tri-tert-butylphosphine tetrafluoroborate (1.74 g, 6.00 mmol), and sodium tert-butoxide (28.83 g, 300.00 mmol) were added to a two-necked flask, followed by 1500 mL of dry toluene and heating to 110 °C. The reaction was allowed to proceed for 12 h. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was then separated by silica gel column chromatography using petroleum ether:dichloromethane in a 10:1 eluent to give intermediate G-11 (94.77 g, 70% yield). HPLC analysis showed a solid purity ≥99.83%. Mass spectrometry m / z: 901.3781 (theoretical value: 901.3799).

[0203] Preparation of compound 11:

[0204] Intermediate G-11 (63.18 g, 70.00 mmol) was dissolved in 1850 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 175 mL) was added, followed by heating to 30 °C and reacting for 1 h. The mixture was then cooled again to -78 °C, and BBr3 (52.61 g, 210.00 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 h. After cooling to 0 °C, N,N-diisopropylethylamine (45.23 g, 350.00 mmol) was added, followed by heating to 160 °C and reacting for 12 h. The solution was dried under vacuum and passed through a silica gel column eluent of petroleum ether:dichloromethane = 10:1 to give compound 11 (20.85 g, yield 34%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 875.4033 (theoretical value: 875.4047). Theoretical elemental content (%) C 63 H 50 BN3O: C, 86.39; H, 5.75; N, 4.80. Actual elemental content (%): C, 86.37; H, 5.74; N, 4.83.

[0205] [Synthetic Example 4] Preparation of Compound 81:

[0206]

[0207] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-81 and D-81, respectively, with all other steps remaining the same, to obtain compound 81 (20.79 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 989.3561 (theoretical value: 989.3577). Theoretical elemental content (%) C73 H 44 BN3O: C, 88.57; H, 4.48; N, 4.24. Actual elemental content (%): C, 88.58; H, 4.46; N, 4.23.

[0208] [Synthetic Example 5] Preparation of Compound 151:

[0209]

[0210] Following the same preparation method as compound 11 in Example 3, A-11 was replaced with an equimolar amount of A-151, with all other steps remaining the same, to obtain compound 151 (21.41 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 873.3879 (theoretical value: 873.3890). Theoretical elemental content (%) C 63 H 48 BN3O: C, 86.59; H, 5.54; N, 4.81. Actual elemental content (%): C, 86.56; H, 5.55; N, 4.83.

[0211] [Synthetic Example 6] Preparation of Compound 156:

[0212]

[0213] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-156 and D-156, respectively, with all other steps remaining the same, to obtain compound 156 (20.80 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 873.3879 (theoretical value: 873.3890). Theoretical elemental content (%) C 63 H 48 BN3O: C, 86.59; H, 5.54; N, 4.81. Actual elemental content (%): C, 86.58; H, 5.56; N, 4.80.

[0214] [Synthetic Example 7] Preparation of Compound 167:

[0215]

[0216] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 was replaced with an equimolar amount of A-167, with all other steps remaining the same, to obtain compound 167 (19.47 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1029.4844 (theoretical value: 1029.4829). Theoretical elemental content (%) C 75 H 60BN3O: C, 87.45; H, 5.87; N, 4.08. Actual element content (%): C, 87.46; H, 5.86; N, 4.06.

[0217] [Synthetic Example 8] Preparation of Compound 187:

[0218]

[0219]

[0220] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-187, respectively, with all other steps remaining the same, to obtain compound 187 (20.11 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1025.4525 (theoretical value: 1025.4516). Theoretical elemental content (%) C 73 H 56 BN3O: C, 87.79; H, 5.50; N, 4.10. Actual elemental content (%): C, 87.78; H, 5.51; N, 4.12.

[0221] [Synthetic Example 9] Preparation of Compound 196:

[0222]

[0223] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-196, respectively, with all other steps remaining the same, to obtain compound 196 (20.23 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 875.3781 (theoretical value: 875.3795). Theoretical elemental content (%) C 61 H 46 BN5O: C, 83.65; H, 5.29; N, 8.00. Actual elemental content (%): C, 83.63; H, 5.28; N, 8.02.

[0224] [Synthetic Example 10] Preparation of Compound 240:

[0225]

[0226] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and F-11 were replaced with equimolar amounts of F-11 and A-240, respectively, with all other steps remaining the same, to obtain compound 240 (19.64 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 904.5129 (theoretical value: 904.5114). Theoretical elemental content (%) C64 H 33 D 17 BN3O: C, 84.94; H, 7.46; N, 4.64. Actual element content (%): C, 84.96; H, 7.47; N, 4.62.

[0227] [Synthetic Example 11] Preparation of Compound 251:

[0228]

[0229] Following the same preparation method as compound 11 in Synthesis Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of F-11, D-156, and A-251, respectively, with all other steps remaining the same, to obtain compound 251 (20.30 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 905.3410 (theoretical value: 905.3429). Theoretical elemental content (%) C 61 H 48 BN3OSi2: C, 80.86; H, 5.34; N, 4.64. Actual elemental content (%): C, 80.85; H, 5.36; N, 4.63.

[0230] [Synthetic Example 12] Preparation of Compound 292:

[0231]

[0232] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and B-11 were replaced with equimolar amounts of A-151 and B-292, respectively, with all other steps remaining the same, to obtain compound 292 (19.95 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 949.4214 (theoretical value: 949.4203). Theoretical elemental content (%) C 69 H 52 BN3O: C, 87.24; H, 5.52; N, 4.42. Actual elemental content (%): C, 87.26; H, 5.51; N, 4.40.

[0233] [Synthetic Example 13] Preparation of Compound 300:

[0234]

[0235] Following the same preparation method as compound 11 in Synthesis Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of A-151, D-300, and F-300, respectively, with all other steps remaining the same, yielding compound 300 (20.56 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 889.3653 (theoretical value: 889.3662). Theoretical elemental content (%) C 63 H 48 BN3S: C, 85.02; H, 5.44; N, 4.72. Actual elemental content (%): C, 85.00; H, 5.43; N, 4.71.

[0236] [Synthetic Example 14] Preparation of Compound 369:

[0237]

[0238] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-369 and D-369, respectively, with all other steps remaining the same, yielding compound 369 (20.96 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 767.2995 (theoretical value: 767.2984). Theoretical elemental content (%) C 55 H 22 D8BN3O: C, 86.05; H, 4.99; N, 5.47. Actual elemental content (%): C, 86.06; H, 4.97; N, 5.46.

[0239] [Synthetic Example 15] Preparation of Compound 385:

[0240]

[0241] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-385, respectively, with all other steps remaining the same, yielding compound 385 (21.97 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 871.3721 (theoretical value: 871.3734). Theoretical elemental content (%) C 63 H 46 BN3O: C, 86.79; H, 5.32; N, 4.82. Actual elemental content (%): C, 86.77; H, 5.33; N, 4.80.

[0242] [Synthetic Example 16] Preparation of Compound 387:

[0243]

[0244] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-387, respectively, with all other steps remaining the same, to obtain compound 387 (22.58 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 871.3752 (theoretical value: 871.3734). Theoretical elemental content (%) C 63 H 46 BN3O: C, 86.79; H, 5.32; N, 4.82. Actual element content (%): C, 86.78; H, 5.30; N, 4.81.

[0245] [Synthetic Example 17] Preparation of Compound 391:

[0246]

[0247] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-391, respectively, with all other steps remaining the same, to obtain compound 391 (21.17 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 1007.3470 (theoretical value: 1007.3482). Theoretical elemental content (%) C 65 H 44 BF6N3O: C, 77.46; H, 4.40; N, 4.17. Actual element content (%): C, 77.44; H, 4.41; N, 4.16.

[0248] [Synthetic Example 18] Preparation of Compound 393:

[0249]

[0250] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-393, respectively, with all other steps remaining the same, to obtain compound 393 (21.23 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 947.4061 (theoretical value: 947.4047). Theoretical elemental content (%) C 69 H 50 BN3O: C, 87.42; H, 5.32; N, 4.43. Actual element content (%): C, 87.41; H, 5.34; N, 4.42.

[0251] [Synthetic Example 19] Preparation of Compound 396:

[0252]

[0253] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-396, respectively, with all other steps remaining the same, yielding compound 396 (20.63 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1015.4510 (theoretical value: 1015.4524). Theoretical elemental content (%) C 69 H 62 BN3OSi2: C, 81.55; H, 6.15; N, 4.13. Actual elemental content (%): C, 81.54; H, 6.17; N, 4.11.

[0254] [Synthetic Example 20] Preparation of Compound 408:

[0255]

[0256] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-408 and D-385, respectively, with all other steps remaining the same, to obtain compound 408 (19.96 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1055.3882 (theoretical value: 1055.3898). Theoretical elemental content (%) C 73 H 54 BN3OSi2: C, 83.01; H, 5.15; N, 3.98. Actual elemental content (%): C, 83.00; H, 5.17; N, 3.97.

[0257] [Synthetic Example 21] Preparation of Compound 410:

[0258]

[0259] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-410, respectively, with all other steps remaining the same, to obtain compound 410 (21.36 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 983.4978 (theoretical value: 983.4986). Theoretical elemental content (%) C 71 H 62 BN3O: C, 86.66; H, 6.35; N, 4.27. Actual elemental content (%): C, 86.67; H, 6.34; N, 4.29.

[0260] [Synthetic Example 22] Preparation of Compound 416:

[0261]

[0262] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-416 and D-385, respectively, with all other steps remaining the same, to obtain compound 416 (20.79 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1023.4376 (theoretical value: 1023.4360). Theoretical elemental content (%) C 75 H 54 BN3O: C, 87.96; H, 5.32; N, 4.10. Actual elemental content (%): C, 87.93; H, 5.34; N, 4.11.

[0263] [Synthetic Example 23] Preparation of Compound 430:

[0264]

[0265] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-430, respectively, with all other steps remaining the same, to obtain compound 430 (20.41 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 971.4034 (theoretical value: 971.4047). Theoretical elemental content (%) C 71 H 50 BN3O: C, 87.73; H, 5.19; N, 4.32. Actual element content (%): C, 87.75; H, 5.18; N, 4.31.

[0266] [Synthetic Example 24] Preparation of Compound 470:

[0267]

[0268] Following the same preparation method as compound 11 in Synthesis Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of A-151, D-385, and F-300, respectively, with all other steps remaining the same, yielding compound 470 (21.75 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 887.3519 (theoretical value: 887.3505). Theoretical elemental content (%) C 63 H 46 BN3S: C, 85.22; H, 5.22; N, 4.73. Actual elemental content (%): C, 85.21; H, 5.24; N, 4.71.

[0269] [Synthetic Example 25] Preparation of Compound 562:

[0270]

[0271] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-562 and D-562, respectively, with all other steps remaining the same, to obtain compound 562 (20.58 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1049.2719 (theoretical value: 1049.2706). Theoretical elemental content (%) C 73 H 40 BN3OS2: C, 83.50; H, 3.84; N, 4.00. Actual elemental content (%): C, 83.51; H, 3.86; N, 4.01.

[0272] [Synthetic Example 26] Preparation of Compound 564:

[0273]

[0274] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-562, respectively, with all other steps remaining the same, to obtain compound 564 (21.95 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 949.4218 (theoretical value: 949.4203). Theoretical elemental content (%) C 69 H 52 BN3O: C, 87.24; H, 5.52; N, 4.42. Actual element content (%): C, 87.26; H, 5.54; N, 4.41.

[0275] [Synthetic Example 27] Preparation of Compound 565:

[0276]

[0277] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-565, respectively, with all other steps remaining the same, to obtain compound 565 (20.83 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 959.4817 (theoretical value: 959.4831). Theoretical elemental content (%) C 69 H 42 D 10 BN3O: C, 86.32; H, 6.51; N, 4.38. Actual elemental content (%): C, 86.34; H, 6.50; N, 4.39.

[0278] [Synthetic Example 28] Preparation of Compound 576:

[0279]

[0280] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-576, respectively, with all other steps remaining the same, to obtain compound 576 (20.70 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 953.4472 (theoretical value: 953.4455). Theoretical elemental content (%) C 69 H 48 D4BN3O: C, 86.87; H, 5.92; N, 4.40. Actual elemental content (%): C, 86.88; H, 5.91; N, 4.41.

[0281] [Synthetic Example 29] Preparation of Compound 598:

[0282]

[0283] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-598 and D-598, respectively, with all other steps remaining the same, yielding compound 598 (20.54 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 977.4506 (theoretical value: 977.4516). Theoretical elemental content (%) C 71 H 56 BN3O: C, 87.19; H, 5.77; N, 4.30. Actual elemental content (%): C, 87.17; H, 5.76; N, 4.32.

[0284] [Synthetic Example 30] Preparation of Compound 623:

[0285]

[0286] Following the same preparation method as compound 11 in Synthesis Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of F-11, D-623, and A-151, respectively, with all other steps remaining the same, yielding compound 623 (21.28 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 949.4217 (theoretical value: 949.4203). Theoretical elemental content (%) C 69 H 52 BN3O: C, 87.24; H, 5.52; N, 4.42. Actual element content (%): C, 87.21; H, 5.54; N, 4.43.

[0287] [Synthetic Example 31] Preparation of Compound 656:

[0288]

[0289] Following the same preparation method as compound 11 in Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of A-151, D-562, and F-300, respectively, with all other steps remaining the same, yielding compound 656 (21.64 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 965.3988 (theoretical value: 965.3975). Theoretical elemental content (%) C 69 H 52 BN3S: C, 85.79; H, 5.43; N, 4.35. Actual elemental content (%): C, 85.78; H, 5.41; N, 4.36.

[0290] [Synthetic Example 32] Preparation of Compound 698:

[0291]

[0292] Following the same preparation method as compound 11 in Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of A-151, D-562, and F-698, respectively, with all other steps remaining the same, yielding compound 698 (21.18 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 975.4711 (theoretical value: 975.4724). Theoretical elemental content (%) C 72 H 58 BN3: C, 88.60; H, 5.99; N, 4.31. Actual elemental content (%): C, 88.62; H, 5.98; N, 4.33.

[0293] [Synthetic Example 33] Preparation of Compound 725:

[0294]

[0295] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-369 and D-725, respectively, with all other steps remaining the same, to obtain compound 725 (22.28 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 837.2709 (theoretical value: 837.2700). Theoretical elemental content (%) C 59 H 32 BN5O: C, 84.59; H, 3.85; N, 8.36. Actual element content (%): C, 84.58; H, 3.83; N, 8.37.

[0296] [Synthetic Example 34] Preparation of Compound 729:

[0297]

[0298] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-81, respectively, with all other steps remaining the same, yielding compound 729 (22.56 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 947.4036 (theoretical value: 947.4047). Theoretical elemental content (%) C 69 H 50 BN3O: C, 87.42; H, 5.32; N, 4.43. Actual element content (%): C, 87.40; H, 5.33; N, 4.41.

[0299] [Synthetic Example 35] Preparation of Compound 745:

[0300]

[0301] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-745, respectively, with all other steps remaining the same, to obtain compound 745 (19.25 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1099.4688 (theoretical value: 1099.4673). Theoretical elemental content (%) C 81 H 58 BN3O: C, 88.43; H, 5.31; N, 3.82. Actual element content (%): C, 88.41; H, 5.30; N, 3.83.

[0302] [Synthetic Example 36] Preparation of Compound 751:

[0303]

[0304] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-751 and D-81, respectively, with all other steps remaining the same, yielding compound 751 (21.07 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1037.3312 (theoretical value: 1037.3326). Theoretical elemental content (%) C 75 H 40 BN5O: C, 86.79; H, 3.88; N, 6.75. Actual elemental content (%): C, 86.77; H, 3.89; N, 6.74.

[0305] [Synthetic Example 37] Preparation of Compound 764:

[0306]

[0307] Following the same preparation method as compound 11 in Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of A-151, D-81, and F-764, respectively, with all other steps remaining the same, yielding compound 764 (21.86 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 975.4379 (theoretical value: 975.4360). Theoretical elemental content (%) C 71 H 54 BN3O: C, 87.37; H, 5.58; N, 4.31. Actual elemental content (%): C, 87.39; H, 5.57; N, 4.34.

[0308] [Synthetic Example 38] Preparation of Compound 777:

[0309]

[0310] Following the same preparation method as compound 11 in Synthesis Example 3, A-11, D-11, and F-11 were replaced with equimolar amounts of F-11, D-777, and A-151, respectively, with all other steps remaining the same, yielding compound 777 (21.33 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 951.4279 (theoretical value: 951.4298). Theoretical elemental content (%) C 69 H 46 D4BN3O: C, 87.05; H, 5.72; N, 4.41. Actual elemental content (%): C, 87.03; H, 5.71; N, 4.40.

[0311] [Synthetic Example 39] Preparation of Compound 790:

[0312]

[0313]

[0314] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-790, respectively, with all other steps remaining the same, yielding compound 790 (21.59 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 963.3983 (theoretical value: 963.3996). Theoretical elemental content (%) C 69 H 50 BN3O2: C, 85.97; H, 5.23; N, 4.36. Actual elemental content (%): C, 85.94; H, 5.24; N, 4.37.

[0315] [Synthetic Example 40] Preparation of Compound 847:

[0316]

[0317] Following the same preparation method as compound 11 in Synthesis Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-847, respectively, with all other steps remaining the same, yielding compound 847 (21.97 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 950.4171 (theoretical value: 950.4156). Theoretical elemental content (%) C 68 H 51 BN4O: C, 85.88; H, 5.41; N, 5.89. Actual element content (%): C, 85.87; H, 5.40; N, 5.88.

[0318] [Synthetic Example 41] Preparation of Compound 851:

[0319]

[0320] Following the same preparation method as compound 11 in Example 3, A-11 and D-11 were replaced with equimolar amounts of A-151 and D-851, respectively, with all other steps remaining the same, to obtain compound 851 (20.79 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1023.4343 (theoretical value: 1023.4360). Theoretical elemental content (%) C 75 H 54 BN3O: C, 87.96; H, 5.32; N, 4.10. Actual elemental content (%): C, 87.95; H, 5.34; N, 4.11.

[0321] [Synthetic Example 42] Preparation of Compound 875:

[0322]

[0323] Preparation of intermediate K-875:

[0324] Under a nitrogen atmosphere, F-11 (64.12 g, 350.00 mmol) and cesium carbonate (228.07 g, 700.00 mmol) were dissolved in 17500 mL of anhydrous DMF solution and stirred for 20 min. Then, compound B-875 (39.80 g, 175.00 mmol) was added, and the mixture was heated to 150 °C for 12 hours and then cooled to room temperature. The reagents were removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 650 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography. The eluent (petroleum ether: dichloromethane = 4:1) gave intermediate K-875 (153.14 g, yield 79%). The solid purity was ≥99.67% as determined by HPLC. Mass spectrometry m / z: 552.0255 (theoretical value: 552.0240).

[0325] Preparation of intermediate L-875:

[0326] Under a nitrogen atmosphere, intermediate K-875 (83.08 g, 150.00 mmol) was dissolved in 300 mL of dry THF, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 180 mL) was added. The reaction was carried out at this temperature for 1 h. Compound D-875 (68.94 g, 150.00 mmol) was dissolved in 1200 mL of dry THF pre-cooled to -78 °C. This solution was then slowly injected into the solution of intermediate K-875 at -78 °C, and the temperature was slowly raised to room temperature for 12 h. After the reaction was completed, a small amount of methanol was added to quench the reaction, the solvent was evaporated under reduced pressure, 3000 mL of glacial acetic acid and 300 mL of concentrated hydrochloric acid were added, and the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with saturated sodium carbonate aqueous solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:dichloromethane in a 5:1 eluent to give intermediate L-875 (96.24 g, 70% yield). HPLC analysis showed a solid purity ≥99.73%. Mass spectrometry m / z: 915.3583 (theoretical value: 915.3592).

[0327] Preparation of compound 875:

[0328] Intermediate L-875 (64.16 g, 70.00 mmol) was dissolved in 1850 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 175 mL) was added, followed by heating to 30 °C and reacting for 1 h. The mixture was then cooled again to -78 °C, and BBr3 (52.61 g, 210.00 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 h. After cooling to 0 °C, N,N-diisopropylethylamine (45.23 g, 350.00 mmol) was added, followed by heating to 160 °C and reacting for 12 h. The solution was dried under vacuum and passed through a silica gel column eluent of petroleum ether:dichloromethane = 10:1 to give compound 875 (22.43 g, yield 36%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 889.3832 (theoretical value: 889.3840). Theoretical elemental content (%) C 63 H 48 BN3O2: C, 85.03; H, 5.44; N, 4.72. Actual elemental content (%): C, 85.04; H, 5.42; N, 4.73.

[0329] Device Example 1:

[0330] First, the ITO (10nm) / Ag (100nm) / ITO (10nm) glass substrate was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then, it was dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaner and cleaned for 5 minutes. After that, the substrate was transferred to an evaporation machine.

[0331] Then, HI-1 and HT-1 with a thickness of 10 nm are deposited on the glass substrate as hole injection layers, with a mass ratio of HI-1 to HT-1 of 3:97. HT-1 with a thickness of 60 nm is deposited on the hole injection layer as a first hole transport layer. EB-1 with a thickness of 20 nm is deposited on the first hole transport layer as an electron blocking layer. A light-emitting layer with a thickness of 30 nm is deposited on the electron blocking layer. The light-emitting layer structure includes GH-1 as the host material and compound 11 as the dopant material. GH-1 and compound 11 are... The mass ratio of compound 11 is 96:4. Then, an HB-1 film with a thickness of 5 nm is deposited on the light-emitting layer as a hole blocking layer. An ET-1 and Liq film with a thickness of 30 nm is deposited on the hole blocking layer as an electron transport layer with a mass ratio of 1:1. A LiF film with a thickness of 1 nm is deposited on the electron transport layer as an electron injection layer. Then, a Mg:Ag alloy with a thickness of 15 nm (the mass ratio of Mg to Ag is 1:9) is deposited on the electron injection layer as a cathode, thereby preparing an organic light-emitting device.

[0332] Device Examples 2 to 40:

[0333] Compounds 81, 151, 156, 167, 187, 196, 240, 251, 292, 300, 369, 385, 387, 391, 393, 396, 408, 410, 416, 430, 470, 562, 564, 565, 576, 598, 623, 656, 698, 725, 729, 745, 751, 764, 777, 790, 847, 851, and 875 of the present invention were used to replace compound 11 in device example 1 as doping materials. Otherwise, organic light-emitting devices were prepared using the same preparation method as in device example 1.

[0334] Comparative Examples 1 to 7:

[0335] Comparative compounds 1, 2, 3, 4, 5, 6, and 7 were used to replace compound 11 in device example 1 as doping materials. Otherwise, organic light-emitting devices were prepared using the same preparation method as in device example 1.

[0336] Device Example 41:

[0337] First, the ITO (10nm) / Ag (100nm) / ITO (10nm) glass substrate was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then, it was dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaner and cleaned for 5 minutes. After that, the substrate was transferred to an evaporation machine.

[0338] Then, HI-1 and HT-1 with a thickness of 10 nm are deposited on the glass substrate as hole injection layers, with a mass ratio of HI-1 to HT-1 of 3:97. HT-1 with a thickness of 60 nm is deposited on the hole injection layer as a first hole transport layer. EB-1 with a thickness of 20 nm is deposited on the first hole transport layer as an electron blocking layer. A light-emitting layer with a thickness of 30 nm is deposited on the electron blocking layer. The light-emitting layer structure includes GH-1 and GH-2 as host materials and compound 11 as a dopant. The mass ratio of compound 2 to compound 11 is 69:30:1. Then, an HB-1 film with a thickness of 5 nm is deposited on the light-emitting layer as a hole blocking layer. An ET-1 and Liq film with a thickness of 30 nm is deposited on the hole blocking layer as an electron transport layer with a mass ratio of 1:1. A LiF film with a thickness of 1 nm is deposited on the electron transport layer as an electron injection layer. Then, a Mg:Ag alloy with a thickness of 15 nm (the mass ratio of Mg to Ag is 1:9) is deposited on the electron injection layer as a cathode, thereby preparing an organic light-emitting device.

[0339] Device Examples 42 to 80:

[0340] Compounds 81, 151, 156, 167, 187, 196, 240, 251, 292, 300, 369, 385, 387, 391, 393, 396, 408, 410, 416, 430, 470, 562, 564, 565, 576, 598, 623, 656, 698, 725, 729, 745, 751, 764, 777, 790, 847, 851, and 875 of the present invention were used to replace compound 11 in device example 41 as doping materials. Otherwise, organic light-emitting devices were prepared using the same preparation method as in device example 41.

[0341] Comparative Examples 8-14:

[0342] Comparative compounds 1, 2, 3, 4, 5, 6, and 7 were used to replace compound 11 in device example 41 as doping materials. Otherwise, organic light-emitting devices were prepared using the same preparation method as in device example 41.

[0343] The molecular structural formulas of the relevant materials are shown below:

[0344]

[0345] A combined IVL testing system was used to test the luminous efficiency and peak emission of organic electroluminescent devices (OLEDs). This system consisted of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The full width at half maximum (FWHM) in the thin-film state was measured using a Horiba Fluorolog-3 series fluorescence spectrometer. The lifetime of the OLEDs was tested using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0346] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known driving circuit, and the device's current efficiency, half-maximum width at half-maximum (FWHM), external quantum efficiency, emission peak value, and lifetime were measured. The test results of the obtained device are shown in Tables 1 and 2.

[0347] Table 1: Luminescence characteristics test results of Device Examples 1 to 40 and Comparative Examples 1 to 7:

[0348]

[0349]

[0350] As can be seen from the device data results in Table 1, compared with Comparative Examples 1 to 7, the current efficiency, device lifetime, and half-width of the device examples 1 to 40 of the present invention have been improved, the color purity of the device has been improved, and the device lifespan has been extended. They are high-performance organic light-emitting device doping materials.

[0351] Table 2: Luminescence characteristics test results of Device Examples 41 to 80 and Comparative Examples 8 to 14:

[0352]

[0353]

[0354]

[0355] As can be seen from the device data results in Table 2, compared with comparative examples 8 to 14, the current efficiency, external quantum efficiency, and device lifetime of device examples 41 to 80 of the present invention have been greatly improved. As can be seen from the full width at half maximum (FWHM), the device examples have an effective multiple resonance effect, which greatly enriches the material system and emission color range of MR-TADF and has good application prospects.

[0356] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound is selected from the structure shown in Formula 1: The M is selected from the structure shown in Equation 1-1, Equation 1-2, or Equation 1-3. The X4 is selected from single bonds, O, S, CRdRe, and NRf; The Rd and Re are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rd and Re are interconnected to form substituted or unsubstituted rings; The Rf and R are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring; Ar1 and Ar2 are each independently selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring; X1 and X2 are each independently selected from none, single bond, O, S, Se, CRaRb, SiRaRb, GeRaRb, NRc, and at least one of X1 and X2 is selected from O, S, Se, CRaRb, SiRaRb, GeRaRb or NRc; The X3 is selected from single bonds, O, S, Se, CRgRh, SiRgRh, GeRgRh, or NRi; Ra and Rb are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Ra and Rb are interconnected to form substituted or unsubstituted rings. The Rg and Rh are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or Rg and Rh are interconnected to form substituted or unsubstituted rings. Rc and Ri are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring; Each of the terms 'a' is independently selected from CR1 or N; Each of the R1s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl, deuterium, tritium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1, C1, C2, C2, C2, C2, C2, C3 ... Each of the b's is independently selected from CR2 or N; Each of the R2s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R2s are connected to form a substituted or unsubstituted ring; Each of the c's is independently selected from CR0 or N; Each of the R0s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R0s are connected to form substituted or unsubstituted rings. Each of the d is independently selected from CR4 or N, and the d connected to M is selected from C; Each of the R4s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R4s are connected to form substituted or unsubstituted rings. Each of the e is independently selected from CR3 or N; Each of the R3s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted alkyl groups of aliphatic ring and C2-C30 fused cycloalcoholic group ... L1 and L2 are each independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring. The asterisk (*) indicates a connection point.

2. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the structures shown in Formula 2-1 to Formula 2-3. The definitions of X1, X2, X3, X4, a, b, c, d, e, R, Ar1, Ar2, L1, and L2 are the same as those in Equation 1.

3. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the structures shown in Formulas 3-1 to 3-5. The X5 is selected from O, S, Se, CRaRb, SiRaRb, GeRaRb or NRc; The definitions of X3, M, a, b, c, d, Ra, Rb, and Rc are the same as those in Equation 1.

4. The boron-nitrogen compound according to claim 1, characterized in that, Equation 1-1 Selected from any one of the following groups, The definitions of R, R3, Rd, Re, Rf, and L1 are the same as those in Equation 1; b1 is selected from 0, 1, 2, 3 or 4; b2 is selected from 0, 1, 2 or 3; b3 is selected from 0, 1 or 2; b4 is selected from 0 or 1.

5. The boron-nitrogen compound according to claim 1, characterized in that, Formulas 1-2 Selected from any one of the following groups, The definitions of R3, Rd, Re, Rf, and L1 are the same as those in Equation 1; c1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c3 is selected from 0, 1, 2, 3, 4, 5 or 6; c4 is selected from 0, 1, 2, 3, 4 or 5.

6. The boron-nitrogen compound according to claim 1, characterized in that, Ar1 and Ar2 are each independently selected from any one of the following groups: substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or groups listed below. The X6 is selected from O, S, CR6R7, NR5, SiR6R7, GeR6R7 or Se; The Y is selected from CR8 or N; R5 and R8 are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring; R6 and R7 are each independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R6 and R7 are interconnected to form substituted or unsubstituted rings. The ring A is selected from substituted or unsubstituted C3 to C20 aliphatic rings; Each of the v values ​​is independently selected from CR9 or N; Each of the R9s is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or substituted or unsubstituted R9s connected to form substituted or unsubstituted rings.

7. The boron-nitrogen compound according to claim 1, characterized in that, L1 and L2 are each independently selected from single bonds or any of the following groups. The X7 is selected from O, S, and CR. 10 R 11 NR 12 SiR 10 R 11 GeR 10 R 11 Or Se; The Q is selected from CR 13 Or N; The R 12 R 13 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring; The R 10 R 11 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R 10 R 11 They connect to each other to form substituted or unsubstituted rings; The ring B is selected from substituted or unsubstituted C3 to C20 aliphatic rings; The n is selected from CR 14 Or N; The R 14 Each is independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or adjacent R 14 They connect to form substituted or unsubstituted rings.

8. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the following structures.

9. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is disposed between the cathode and the anode, and the organic layer comprises a light-emitting layer, characterized in that, The light-emitting layer comprises at least one or more boron nitrogen compounds according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material and a dopant material, characterized in that, The doped material comprises at least one or more boron nitride compounds according to any one of claims 1 to 8.

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