Boron-nitrogen heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a boron-nitrogen heterocyclic compound and an organic electroluminescent device thereof. The boron-nitrogen heterocyclic compound provided by the invention has relatively large steric hindrance, on one hand, molecular vibration is reduced, and the boron-nitrogen heterocyclic compound has relatively narrow half-peak width and can effectively improve the color purity of light emitted by a device; on the other hand, the distance between molecules is increased, the acting force between the molecules is weakened, quenching caused by aggregation is overcome, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic photoelectric materials, and in particular relates to a boron-nitrogen heterocyclic compound and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the characteristics of light weight, wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity, and good flexibility. It has been widely used in the lighting and display fields and is considered by the industry to be one of the most promising display and lighting technologies.

[0003] OLED devices have a cathode and an anode, with a light-emitting layer sandwiched between them. This layer contains a luminescent substance (guest material). When the device is powered on, holes and electrons are injected from the anode and cathode, respectively, into the light-emitting layer, where they recombine to form excitons and release energy. Under the action of the electric field, the excitons migrate, transferring energy to the luminescent substance. Electrons in the luminescent substance molecules transition from the ground state to the excited state. Because the excited state is unstable, the electrons return from the excited state to the ground state, releasing energy in the form of light, producing luminescence. Traditional OLED fluorescent materials prohibit the radiative transition of electrons from the triplet energy level to the ground state, and the triplet energy is deactivated in the form of non-radiative transitions, resulting in a device internal quantum efficiency of only 25%. Phosphorescent materials, on the other hand, utilize the spin-orbit coupling effect, and the device internal quantum efficiency can reach 100%. However, most phosphorescent materials contain precious metals, which can be expensive and have poor color purity.

[0004] In recent years, novel thermally activated delayed fluorescence (MR-TADF) materials with multiple resonance effects have become a research hotspot in the OLED field due to their advantages such as high efficiency and narrow emission spectrum. Generally speaking, boron-nitrogen heterocyclic compounds with resonant structures are more likely to achieve narrow half-width (FWHM) emission. However, they can experience aggregation-induced quenching in doped thin films, resulting in reduced luminous efficiency and color purity in the resulting devices. Therefore, the development of MR-TADF materials with even better performance is urgently needed. Summary of the Invention

[0005] To solve the above technical problems, the present invention provides a boron-nitrogen heterocyclic compound having a structure shown in formula (I):

[0006]

[0007] Wherein, the ring E, ring F, ring G, and ring H are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0008] Said X1, X2, X3 are independently selected from CR or nitrogen atoms, and at least two of them are not selected from nitrogen atoms;

[0009] Wherein, at least one R is selected from the group represented by formula (II-A) or formula (II-B):

[0010]

[0011] Wherein, the ring P and ring Q are independently selected from one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0012] The Ar is selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0013] The L1 and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0014] Furthermore, at least one R is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a combination thereof;

[0015] The remaining R is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C10 cycloalkyl group;

[0016] The condition is that the molecule contains at least one deuterium atom.

[0017] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer contains the boron-nitrogen heterocyclic compound of the present invention.

[0018] Beneficial effects:

[0019] The boron-nitrogen heterocyclic compound provided by the present invention has a large steric hindrance. On the one hand, it reduces the vibration of the molecules and has a narrow half-peak width, which can effectively improve the color purity of the light emitted by the device. On the other hand, it increases the distance between molecules, weakens the intermolecular forces, overcomes the quenching caused by aggregation, and can improve the luminous efficiency and service life of the device. DETAILED DESCRIPTION

[0020] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0021] In the compounds of the present invention, any atom not designated as a specific isotope includes any stable isotope of that atom and includes atoms at both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain approximately 0.0156 atomic % deuterium per hydrogen atom.

[0022] As used herein, the use of "H" and "hydrogen atom" means that the hydrogen atoms in a chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium atom" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is deuterium. "T" and "tritium atom" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is tritium. As used herein, the omitted hydrogen represents "H" or "hydrogen atom".

[0023] The halogen mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0024] The "silyl group" in the present invention refers to a -SiH3 group, and the "substituted or unsubstituted silyl group" refers to one or more H groups on the silyl group being substituted or unsubstituted. The "substituted or unsubstituted silyl group" can be -Si(R k )3 indicates that each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic ring and C6-C60 aromatic ring fused ring group, substituted or unsubstituted C3-C30 alicyclic ring and C2-C60 heteroaryl ring fused ring group. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms in the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms in the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R kand the like or different groups selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, and substituted or unsubstituted isoquinoline. Preferably, the substituted silyl group specifically includes trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, isopropyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, diphenylpyridylsilyl, phenyldipyridylsilyl, tripyridylsilyl, etc., but is not limited thereto. The above-mentioned substituted silyl group is preferably trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, isopropyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl.

[0025] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but is not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0026] The cycloalkyl group described herein refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane. Preferred cycloalkyl groups include cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, and norbornane.

[0027] The cycloalkenyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. The cycloalkenyl groups are preferably cyclopentenyl and cyclohexenyl.

[0028] The heterocycloalkyl group described herein refers to a group formed by removing a hydrogen atom from a heterocyclic molecule containing at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, with nitrogen, oxygen, and sulfur atoms being preferred. It preferably contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It preferably has 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples include, but are not limited to, oxiranyl, thioranyl, propidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl. Preferred heterocyclic groups are tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0029] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. It can be a monocyclic aryl group, a polycyclic aryl group, or a condensed ring aryl group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aromatic group refers to an aromatic group having only one aromatic ring in the molecule, for example, phenyl, etc., but not limited thereto; the polycyclic aromatic group refers to an aromatic group containing two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aromatic group refers to an aromatic group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited thereto. The above-mentioned aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0030] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include, but are not limited to, furyl, thienyl, pyrrolyl, imidazolyl, pyridyl, pyrimidinyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, phenylfuranyl, phenylthienyl, etc.; the condensed-ring heteroaryl groups include, but are not limited to, benzothienyl, benzofuranyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, etc., but are not limited to. The heteroaryl group is preferably a benzothiophenyl group, a benzofuranyl group, an indolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a pyridyl group.

[0031] The monovalent group formed by the fusion of an aliphatic ring and an aromatic ring of the present invention refers to a general term for a monovalent group formed by the fusion of an aliphatic ring (cycloalkane, cycloalkene, cycloalkyne) with an aromatic ring and removing one hydrogen atom. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, most preferably 6 to 12 carbon atoms, and may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of the monovalent group formed by the condensation of an aliphatic ring and an aromatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.

[0032] The monovalent group formed by the fusion of an aliphatic ring and a heteroaromatic ring according to the present invention refers to a general term for a monovalent group after aliphatic rings (cycloalkanes, cycloalkenes, cycloalkynes) and heteroaromatic rings are fused together and a hydrogen atom is removed. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, which may include furyl, thienyl, pyrrolyl, imidazolyl, pyridyl, pyrimidine, benzothienyl, benzofuranyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothiophene ... benzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiol, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, etc., but not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, which may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, cycloheptyne. Preferably, examples of the monovalent group formed by the condensation of the aliphatic ring and the heteroaromatic ring may include pyridocyclobutane, pyridocyclopentane, pyridocyclohexane, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidocyclopentane, pyrimidocyclohexane, etc., but not limited thereto.

[0033] The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0034] The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the heteroaryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0035] The divalent group formed by the fusion of an aliphatic ring and an aromatic ring described herein refers to a group formed by the fusion of an aliphatic ring and an aromatic ring having two bonding sites, i.e., a divalent group. The description of the group formed by the fusion of an aliphatic ring and an aromatic ring provided above applies, except that the divalent group formed by the fusion of an aliphatic ring and an aromatic ring is a divalent group.

[0036] The divalent group formed by the fusion of an aliphatic ring and a heteroaromatic ring described herein refers to a group formed by the fusion of an aliphatic ring and an aromatic ring having two bonding sites, i.e., a divalent group. The description of the group formed by the fusion of an aliphatic ring and a heteroaromatic ring provided above applies, except that the divalent group formed by the fusion of an aliphatic ring and a heteroaromatic ring is a divalent group.

[0037] The term "substituted" as used herein means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., a substituent), and the position of the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0038] The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of a deuterium atom, a tritium atom, a halogen, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, or a C3-C12 cycloalkenyl group. , C3-C12 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, substituted or unsubstituted silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated cyclobutane, cyclopentane, methyl-substituted Cyclopentanyl, ethyl-substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl-substituted cyclohexanyl, ethyl-substituted cyclohexanyl, n-propyl-substituted cyclohexanyl, n-butyl-substituted cyclohexanyl, cyclohexane-substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl , deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, benzoxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted by multiple substituents, the multiple substituents are the same or different from each other, and two adjacent substituents may be linked to form a ring.

[0039] In this specification, when the position of a substituent or a connection site on a ring is not fixed, it means that it can be connected to any of the optional sites of the ring. For example, Can be represented Can be represented Can be represented And so on.

[0040] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the rings. For example, Can be represented or Can be represented Can represent or And so on.

[0041] The linked ring structures (e.g., saturated or unsaturated C3-C10 carbocyclic rings, substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic rings) mentioned in the present invention refer to groups connected to each other by chemical bonds, optionally forming double bonds / triple bonds, and may constitute aromatic groups, as shown in the following examples:

[0042]

[0043] In the present invention, the ring formed by 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 connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0044] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0045] When a layer in the present invention is “on” another layer or electrode, it can be interpreted as being directly on the other layer or electrode, or there can be other layer structures in between.

[0046] The term "a layer between two layers, two electrodes, or a layer and an electrode" in the present invention may be interpreted as a single layer structure between the two layers, or one or more layer structures may exist between the two layers.

[0047] The present invention provides a boron-nitrogen heterocyclic compound having a structure shown in formula (I):

[0048]

[0049] Wherein, the ring E, ring F, ring G, and ring H are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0050] Said X1, X2, X3 are independently selected from CR or nitrogen atoms, and at least two of them are not selected from nitrogen atoms;

[0051] Wherein, at least one R is selected from the group represented by formula (II-A) or formula (II-B):

[0052]

[0053] Wherein, the ring P and ring Q are independently selected from one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0054] The Ar is selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0055] The L1 and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0056] Furthermore, at least one R is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a combination thereof;

[0057] The remaining R is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C10 cycloalkyl group;

[0058] The condition is that the molecule contains at least one deuterium atom.

[0059] Preferably, the substituents in the "substituted or unsubstituted" are independently selected from one or more of a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring. When there are multiple substituents, the multiple substituents are the same or different.

[0060] Preferably, the substituents in the "substituted or unsubstituted" are independently selected from deuterium atoms; fluorine atoms; cyano groups; methyl groups substituted or unsubstituted by deuterium atoms or fluorine atoms; ethyl groups; n-propyl groups; isopropyl groups substituted or unsubstituted by deuterium atoms or fluorine atoms; n-butyl groups; sec-butyl groups; isobutyl groups; tert-butyl groups substituted or unsubstituted by deuterium atoms or fluorine atoms; the following groups substituted or unsubstituted by one or more of deuterium atoms, methyl groups, ethyl groups, isopropyl groups and tert-butyl groups: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl and norbornane; the following groups substituted or unsubstituted by one or more of deuterium atoms, fluorine atoms, cyano groups, methyl groups, ethyl groups, isopropyl groups, tert-butyl groups, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl and norbornane: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl; one or more of silyl groups substituted with one or more of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine atom-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, phenanthrenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl or unsubstituted; when there are multiple substituents, the multiple substituents are the same or different.

[0061] Preferably, the ring E, ring F, ring G, ring H, ring P, and ring Q are independently selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted benzocyclopropane ring, a substituted or unsubstituted benzocyclobutane ring, a substituted or unsubstituted benzocyclopentane ring, a substituted or unsubstituted benzocyclohexane ring, a substituted or unsubstituted benzocycloheptane ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted quinoline ring, and a substituted or unsubstituted isoquinoline ring.

[0062] Preferably, R in X1 and / or X3 is selected from the group represented by formula (II-A) or formula (II-B); or, R in X2 is selected from the group represented by formula (II-A) or formula (II-B).

[0063] Preferably, the formula (II-A) is selected from one of the following groups:

[0064]

[0065] wherein each occurrence of a2 is the same or different selected from 0, 1, 2 or 3; each occurrence of b2 is the same or different selected from 0, 1, 2, 3 or 4; each occurrence of c2 is the same or different selected from 0, 1 or 2;

[0066] The R 21 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0067] The Ar is selected from trimethylsilyl, triphenylsilyl, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, or one of the following groups:

[0068]

[0069] Each occurrence of a3 is the same or different selected from 0, 1, 2, 3, 4, or 5; each occurrence of b3 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of c3 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of d3 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; each occurrence of e3 is the same or different selected from 0, 1, 2 or 3; each time f3 occurs, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time g3 occurs, it is selected from 0, 1 or 2 in the same or different manner; each time h3 occurs, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time i3 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time j3 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner;

[0070] The R 31Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0071] The R 32 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0072] The X3 is selected from O, S, CR 33 R 34 or NR 35 , the R 33 、R 34 、R 35 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 33 、R 34 Can be connected to form a ring;

[0073] The R 36 One selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0074] The X4 is selected from O, S or NR 37 , the R 37One selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0075] The L1 and L2 are independently selected from a single bond and one of the following groups:

[0076]

[0077] The a 101 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said c 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 101 Each occurrence is identically or differently selected from 0, 1 or 2; said e 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said f 101 Each occurrence is identically or differently selected from 0, 1, 2 or 3;

[0078] The R 101 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0079] The R 102 Each occurrence is identically or differently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group.

[0080] Preferably, the formula (II-B) is selected from one of the following groups:

[0081]

[0082]

[0083] Each occurrence of a4 is the same or different and is selected from 0, 1, 2, 3 or 4; each occurrence of b4 is the same or different and is selected from 0, 1, 2, 3, 4 or 5; each occurrence of c4 is the same or different and is selected from 0, 1 or 2;

[0084] The R 41 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0085] The L1 is as described in the present invention.

[0086] Preferably, in formula (II-A), at least one of Ar, L1, L2, ring P, and ring Q contains a deuterium atom.

[0087] Preferably, in formula (II-A), Ar is selected from deuterated methyl, deuterated isopropyl, deuterated tert-butyl, and one of the following groups:

[0088]

[0089]

[0090] Preferably, in formula (II-A), at least one of L1 and L2 is selected from one of the following groups:

[0091]

[0092] Preferably, in formula (II-A), the ring P is selected from one of the following groups:

[0093]

[0094] Among them, the It is the bond connecting ring P and L2.

[0095] Preferably, in formula (II-A), the ring Q is selected from one of the following groups:

[0096]

[0097] Preferably, there are no hydrogen atoms in formula (II-A).

[0098] Preferably, in formula (II-B), at least one of L1, ring P, and ring Q contains a deuterium atom.

[0099] Preferably, in formula (II-B), L1 is selected from one of the following groups:

[0100]

[0101] Preferably, in formula (II-B), at least one group in the ring P and the ring Q is selected from one of the following groups:

[0102]

[0103] Preferably, there are no hydrogen atoms in formula (II-B).

[0104] Preferably, at least one R is selected from one of the groups shown below (more preferably, R in X1 and / or X3 is selected from a group represented by formula (II-A) or formula (II-B), and R in X2 is selected from one of the groups shown below):

[0105]

[0106]

[0107] Each occurrence of a1 is the same or different selected from 0, 1, 2, 3, 4, or 5; each occurrence of b1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of c1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of d1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; each occurrence of e1 is the same or different selected from 0, 1, 2 or 3; each time f1 occurs, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time g1 occurs, it is selected from 0, 1 or 2 in the same or different manner; each time h1 occurs, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time i1 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time j1 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner;

[0108] The R 11Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0109] The R 12 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0110] The X0 is selected from O, S or CR 10 R 20 , the R 10 、R 20 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 10 、R 20 Can be connected to form a ring;

[0111] The X1 is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 、R 15 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 13 、R 14 Can be connected to form a ring;

[0112] The R16 One selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0113] The X2 is selected from O, S or NR 17 , the R 17 One selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring.

[0114] Preferably, said R contains at least one deuterium atom.

[0115] Preferably, at least one R is selected from one of the following groups:

[0116]

[0117]

[0118] Preferably, at least one of the rings E, F, G, and H contains a deuterium atom.

[0119] Preferably, at least one of the rings E, F, G, H, P, and Q is selected from a deuterated benzene ring, a deuterated naphthalene ring, a deuterated anthracene ring, a deuterated phenanthrene ring, a deuterated triphenylene ring, a deuterated benzocyclopropane ring, a deuterated benzocyclobutane ring, a deuterated benzocyclopentane ring, a deuterated benzocyclohexane ring, a deuterated benzocycloheptane ring, a deuterated pyridine ring, a deuterated pyrimidine ring, a deuterated quinoline ring, and a deuterated isoquinoline ring.

[0120] Preferably, the ring E and ring F are both selected from deuterated benzene rings.

[0121] Preferably, the ring G and the ring H are both selected from deuterated benzene rings.

[0122] Preferably, when ring E, ring F, ring G, ring H, ring P, and ring Q are deuterated rings, the rings are fully deuterated, which means that all "-CH=" on the rings are replaced with "-CD=".

[0123] Preferably, the remaining R is selected from one of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, a tert-butyl group, and a deuterated tert-butyl group.

[0124] Preferably, the boron-nitrogen heterocyclic compound has a structure shown in formula (IA) or formula (IB):

[0125]

[0126] Wherein, the R is selected from the aforementioned substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a combination thereof;

[0127] The ring E, ring F, ring G, ring H, ring P, ring Q, Ar, L1, and L2 are as described in the present invention.

[0128] Preferably, the boron nitrogen heterocyclic compound is selected from one of the following compounds:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] The boron nitrogen heterocyclic compound represented by formula (I) of the present invention can be prepared by the following synthetic route:

[0153]

[0154] When the boron nitrogen heterocyclic compound of the present invention has the structure shown in formula (IA), it can also be prepared by the following synthetic route:

[0155]

[0156] When the boron nitrogen heterocyclic compound of the present invention has the structure shown in formula (IB), it can also be prepared by the following synthetic route:

[0157]

[0158] Wherein, the ring E, ring F, ring G, ring H, X1, X2, X3, L1, L2, Ar, and R are as described in the present invention;

[0159] The X and Z are independently selected from fluorine atoms, chlorine atoms, bromine atoms or iodine atoms;

[0160] Said V1 and V2 are independently selected from B(OH)2 or

[0161] The above-mentioned synthetic route adopts the reaction type commonly used in organic synthesis, and the reaction conditions (for example, the selection of the type of reaction solvent, catalyst, ligand, base, etc., the amount used, and the order and method of addition) are not particularly limited. The above-mentioned preparation method has readily available raw materials, a simple preparation process, and an excellent yield. The present invention can also be synthesized using the conventional reaction type in other organic synthesis without particular limitation. The above is only an example of the synthetic route.

[0162] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer contains the boron-nitrogen heterocyclic compound of the present invention.

[0163] Preferably, the light-emitting layer comprises a host material and a guest material, and the guest material contains the boron-nitrogen heterocyclic compound described in the present invention.

[0164] Preferably, the light-emitting layer comprises a first host material, a second host material and a guest material, and the guest material contains the boron-nitrogen heterocyclic compound described in the present invention.

[0165] Preferably, the light-emitting layer comprises a host material, an exciton-sensitizing material and a guest material, and the guest material contains the boron-nitrogen heterocyclic compound described in the present invention.

[0166] Preferably, the light-emitting layer comprises a first host material, a second host material, an exciton-sensitizing material and a guest material, and the guest material contains the boron-nitrogen heterocyclic compound described in the present invention.

[0167] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer, the hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, the hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer.

[0168] The hole injection layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, radialene compounds, and other substances with high hole injection properties can be used, for example, 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-17, and compounds p-1 to p-3, but are not limited thereto.

[0169]

[0170] The hole transport layer of the present invention can be a single layer structure composed of a single substance, or a single layer structure or a multilayer structure composed of different substances. Triarylamine compounds can be used, or other materials with hole mobility in the range of 10 -6 cm 2 / Vs or above, for example, N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-17 shown above, but not limited thereto.

[0171] The light-emitting auxiliary layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives can be used, and other substances with appropriate HOMO and T1 energy levels can also be used. Examples include TPD, NPB, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and compounds HT-1 to HT-17 shown above, but are not limited thereto.

[0172] The light-emitting layer of the present invention includes a guest material and a host material, and a dual host material formed by two host materials can be used. The host material includes heterocyclic compounds, metal complexes, aromatic amine compounds, etc., but is not limited thereto. Specific examples may include 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(N-carbazol-9-yl)benzene (MCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), 9,10-di(2-naphthyl)anthracene (ADN), etc., but are not limited thereto. The guest material includes aromatic amine derivatives, boron complexes, metal complexes, etc., but is not limited thereto. Specific examples may include tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenyl-isoquinolinato)(acetylacetonato)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinolinato)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), the boron nitrogen heterocyclic compound of the present invention, etc., but are not limited thereto. The boron nitrogen heterocyclic compound of the present invention is preferred.

[0173] The exciton-sensitizing material described herein refers to a material that enables the luminescent material in the light-emitting layer to fully utilize electrically generated excitons, thereby causing the light-emitting layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers in organic electroluminescent devices may perform functions such as exciton capture, exciton conversion, and exciton transfer. The exciton-sensitizing material may be a complex containing a metal element, such as an iridium complex, but is not limited thereto.

[0174] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer, the electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, the electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0175] The electron injection layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. One or more of the following substances may be selected: 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, and other substances with high electron injection properties. Examples include, but are not limited to, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, and the like.

[0176] The electron transport layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, etc. with high electron transport properties can be used. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), and 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited thereto.

[0177] The hole blocking layer of the present invention can be a single layer structure composed of a single material, or a single layer structure or a multilayer structure composed of different materials. The selected material requires a T1 energy level higher than the light-emitting layer, so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material must be lower than the HOMO energy level of the main material of the light-emitting layer, so as to play a role in blocking holes. Furthermore, the electron mobility of the hole blocking layer material used is 10 -6 cm 2 / Vs or above, which facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymer compounds, etc. Examples include, but are not limited to, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq.

[0178] The anode described in the present invention can be a reflective anode, such as a reflective film formed by silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb) or their alloys, or a layer structure with a high work function and being transparent or translucent, such as a layer structure formed by indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3) or tin oxide (SnO2). The specific type of anode depends on the type of device to be prepared. If the device to be prepared is a bottom-emitting device (emitting light on the anode side), a transparent or translucent anode needs to be made. If the device to be prepared is a top-emitting device (emitting light on the cathode side), a reflective anode needs to be made.

[0179] The cathode described in the present invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc., and can be made into a reflective electrode, a transparent electrode or a semi-transparent electrode by adjusting the thickness of the film. If a bottom-emitting device is to be prepared, a reflective cathode needs to be made. If a top-emitting device is to be prepared, a transparent or semi-transparent cathode needs to be made.

[0180] Preferably, the organic electroluminescent device further comprises a covering layer on the side of the cathode facing away from the anode.

[0181] The cover layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The cover layer material may be an organic or inorganic substance with an appropriate refractive index, such as a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic hydrocarbon compound, aromatic amine compound, etc. Examples include, but are not limited to, LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, and compound CP-4.

[0182]

[0183] The above-mentioned organic layers, cathode, and anode can be prepared by any method including vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There is no special restriction on the thickness of each layer, as long as good device performance is obtained.

[0184] The above-mentioned organic layers are preferably prepared by vacuum evaporation, inkjet printing or spin coating.

[0185] The thickness of each organic layer is generally between 1 nm and 100 μm, preferably between 5 nm and 1000 nm, and more preferably between 5 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0186] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, VR and car taillights.

[0187] The technical solutions and technical effects of the present invention are further described below with reference to embodiments and comparative examples.

[0188] The mass spectra of the compounds of the present invention were determined using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, using chloroform as the solvent.

[0189] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0190] Synthesis Example 1: Synthesis of Compound 83

[0191]

[0192] Compound AA-83 (34.11 g, 150 mmol), compound BB-83 (22.85 g, 180 mmol), and potassium carbonate (37.32 g, 270 mmol) were dissolved in 675 mL of a mixture of THF and water (volume ratio 4:1). Pd(PPh3)4 (5.20 g, 4.5 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate CC-83 (31.99 g, 92.86% yield). HPLC analysis of the solid showed a purity of ≥99.75%. Mass spectrum: m / z: 229.0527 (theoretical value: 229.0518).

[0193] Intermediate CC-83 (22.97 g, 100 mmol), compound DD-83 (61.47 g, 220 mmol), and cesium carbonate (107.52 g, 330 mmol) were dissolved in DMF (1250 mL) and refluxed under nitrogen for 9 hours. After completion of the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate EE-83 (68.47 g, 91.47% yield). HPLC analysis of the solid showed a purity of ≥99.83%. Mass spectrum: m / z: 747.4355 (theoretical value: 747.4368).

[0194] Intermediate EE-83 (59.88 g, 80 mmol) was dissolved in tert-butylbenzene (1350 mL). n-Butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was added dropwise at 0°C under nitrogen. The mixture was then heated to 70°C and stirred for 2 hours. After cooling to 0°C, BBr3 (15.33 mL, 160 mmol) was added dropwise. The reaction system was returned to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (26.40 mL, 160 mmol, DIEA) was added dropwise again at 0°C. The reaction system was heated to 150°C and stirred for 12 hours. After completion of the reaction, the reaction was quenched with 135 mL of methanol and then washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain intermediate FF-83 (20.28 g, 35.11% yield). HPLC analysis of the solid showed a purity of ≥99.31%. Mass spectrum: m / z: 721.4625 (theoretical value: 721.4616).

[0195] Under nitrogen, intermediate FF-83 (14.44 g, 20 mmol) and NBS (3.56 g, 20 mmol) were dissolved in 450 mL of chloroform and allowed to react at room temperature for 12 hours. Upon completion, the solvent was evaporated and the product was passed through a neutral silica gel column (eluents: dichloromethane and petroleum ether) to obtain intermediate GG-83 (13.63 g, 85.12% yield). HPLC analysis revealed a purity of 99.45% and a mass spectrum of m / z: 799.3729 (theoretical value: 799.3721).

[0196] Under nitrogen protection, intermediate GG-83 (8.01 g, 10 mmol) and compound HH-83 (5.74 g, 20 mmol) were dissolved in 80 mL of a mixture of tetrahydrofuran and water (volume ratio 3:1). Pd(PPh3)4 (0.35 g, 0.3 mmol) and potassium carbonate (5.53 g, 40 mmol) were then added and refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, the solvent was dried, and passed through a neutral silica gel column (eluent: dichloromethane and petroleum ether) to obtain compound 83 (6.29 g, yield 65.34%). The solid purity was determined by HPLC to be ≥99.91%. Mass spectrum m / z: 962.5520 (theoretical value: 962.5507). Theoretical element content (%) C 70 H 59 D5BN3: C, 87.29; H, 7.22; N, 4.36. Measured element content (%): C, 87.27; H, 7.26; N, 4.33.

[0197] Synthesis Example 2: Synthesis of Compound 104

[0198]

[0199] BB-83 was replaced with an equal molar amount of BB-104, and HH-83 was replaced with an equal molar amount of HH-104. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 104 (6.27 g, 61.76% yield). HPLC analysis of the solid showed a purity of ≥99.93%. Mass spectrum: m / z: 1014.5798 (theoretical value: 1014.5789). Theoretical element content (%): C 74 H 59 D7BN3: C, 87.55; H, 7.25; N, 4.14. Measured element content (%): C, 87.58; H, 7.27; N, 4.12.

[0200] Synthesis Example 3: Synthesis of Compound 126

[0201]

[0202] BB-83 was replaced with an equal molar amount of BB-126, and HH-83 was replaced with an equal molar amount of HH-126. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 126 (6.24 g, 60.07% yield). The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 1038.5838 (theoretical value: 1038.5820). Theoretical element content (%): C 76 H 63 D5BN3: C, 87.84; H, 7.08; N, 4.04. Measured element content (%): C, 87.86; H, 7.03; N, 4.06.

[0203] Synthesis Example 4: Synthesis of Compound 132

[0204]

[0205] HH-83 was replaced with an equal molar amount of HH-132. The other steps were the same as those in Synthesis Example 1 to obtain Compound 132 (6.88 g, 66.17% yield). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1038.5836 (theoretical value: 1038.5820). Theoretical element content (%): C 76 H 63 D5BN3: C, 87.84; H, 7.08; N, 4.04. Measured element content (%): C, 87.81; H, 7.05; N, 4.09.

[0206] Synthesis Example 5: Synthesis of Compound 152

[0207]

[0208] BB-83 was replaced with an equal molar amount of BB-152, DD-83 was replaced with an equal molar amount of DD-152, and HH-83 was replaced with an equal molar amount of HH-152. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 152 (5.24 g, 61.14% yield). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum: m / z: 856.3769 (theoretical value: 856.3755). Theoretical element content (%): C 63 H 33 D7BN3: C, 88.31; H, 5.53; N, 4.90. Measured element content (%): C, 88.32; H, 5.58; N, 4.86.

[0209] Synthesis Example 6: Synthesis of Compound 164

[0210]

[0211] BB-83 was replaced with an equal molar amount of BB-164, DD-83 was replaced with an equal molar amount of DD-152, and HH-83 was replaced with an equal molar amount of HH-164. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 164 (4.79 g, 60.08% yield). HPLC analysis of the solid showed a purity of ≥99.96%. Mass spectrum: m / z: 796.3542 (theoretical value: 796.3551). Theoretical element content (%): C 57 H 21 D 12 BN4: C, 85.92; H, 5.69; N, 7.03. Measured element content (%): C, 85.99; H, 5.64; N, 7.01.

[0212] Synthesis Example 7: Synthesis of Compound 219

[0213]

[0214] BB-83 was replaced with an equal molar amount of BB-219, and DD-83 was replaced with an equal molar amount of DD-219. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 219 (5.19 g, 61.97% yield). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum: m / z: 837.3688 (theoretical value: 837.3674). Theoretical element content (%): C 60 H 20 D 14 BN3O: C, 86.01; H, 5.77; N, 5.02. Measured element content (%): C, 86.08; H, 5.73; N, 5.00.

[0215] Synthesis Example 8: Synthesis of Compound 274

[0216]

[0217] Compound AA-274 (31.65 g, 150 mmol), compound BB-83 (22.85 g, 180 mmol), and potassium carbonate (37.32 g, 270 mmol) were dissolved in 675 mL of a 4:1 volume ratio mixture of THF and water. Pd(PPh3)4 (5.20 g, 4.5 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate CC-274 (30.16 g, 94.31% yield). HPLC analysis of the solid showed a purity of ≥99.82%. Mass spectrum: m / z: 213.0829 (theoretical value: 213.0814).

[0218] Compound CC-274 (21.32 g, 100 mmol) was dissolved in 335 mL of tetrahydrofuran. Lithium diisopropylamide (LDA, 50 mL, 100 mmol, 2 M solution in tetrahydrofuran) was added dropwise at -20°C under nitrogen. Stirring was continued for 1 hour, followed by the addition of elemental iodine (25.38 g, 100 mmol). The mixture was allowed to return to room temperature and stirred for another 4 hours. After completion of the reaction, the mixture was washed with sodium thiosulfate solution and dichloromethane. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate DD-274 (30.03 g, 88.55% yield). HPLC analysis of the solid showed a purity of ≥99.85%. Mass spectrum: m / z: 338.9790 (theoretical value: 338.9780).

[0219] Intermediate DD-274 (27.13 g, 80 mmol), compound DD-152 (16.05 g, 96 mmol), and cesium carbonate (39.10 g, 120 mmol) were dissolved in DMF (800 mL) and refluxed under nitrogen for 8 hours. After completion of the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate FF-274 (35.69 g, 91.73% yield). HPLC analysis of the solid showed a purity of ≥99.88%. Mass spectrum: m / z: 486.0468 (theoretical value: 486.0453).

[0220] Intermediate FF-274 (24.32 g, 50 mmol), compound DD-83 (30.74 g, 110 mmol), and cesium carbonate (53.76 g, 165 mmol) were dissolved in DMF (625 mL) and refluxed under nitrogen for 9 hours. After completion of the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate HH-274 (45.66 g, 90.85% yield). HPLC analysis of the solid showed a purity of ≥99.79%. Mass spectrum: m / z: 1004.4317 (theoretical value: 1004.4302).

[0221] Intermediate HH-274 (30.15 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). n-Butyllithium (18 mL, 45 mmol, 2.5 M solution in n-hexane) was added dropwise at 0°C under nitrogen. The mixture was then heated to 70°C and stirred for 2 hours. BBr (5.75 mL, 60 mmol) was added dropwise after cooling to 0°C. The reaction system was returned to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0°C. The reaction system was heated to 150°C and stirred for 12 hours. After completion of the reaction, the reaction was quenched with 51 mL of methanol and washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain compound 274 (9.23 g, 34.69% yield). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 886.5182 (theoretical value: 886.5194). Theoretical element content (%) C 64 H 55 D5BN3: C, 86.66; H, 7.39; N, 4.74. Measured element content (%): C, 86.68; H, 7.35; N, 4.75.

[0222] Synthesis Example 9: Synthesis of Compound 278

[0223]

[0224] DD-83 was replaced with an equal molar amount of GG-278. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 278 (10.03 g, 34.56% yield). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum m / z: 966.3931 (theoretical value: 966.3942). Theoretical element content (%): C 72 H 39 D5BN3: C, 89.43; H, 5.11; N, 4.35. Measured element content (%): C, 89.41; H, 5.17; N, 4.32.

[0225] Synthesis Example 10: Synthesis of Compound 280

[0226]

[0227] DD-83 was replaced with an equal molar amount of GG-280. The other steps were the same as those in Synthesis Example 8 to obtain Compound 280 (12.35 g, 34.54% yield). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 1190.6459 (theoretical value: 1190.6446). Theoretical element content (%): C 88 H 71 D5BN3: C, 88.71; H, 6.85; N, 3.53. Measured element content (%): C, 88.73; H, 6.81; N, 3.56.

[0228] Synthesis Example 11: Synthesis of Compound 299

[0229]

[0230] DD-83 was replaced with an equal molar amount of GG-299. The other steps were the same as those in Synthesis Example 8 to obtain Compound 299 (8.25 g, 36.07% yield). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 762.3019 (theoretical value: 762.3003). Theoretical element content (%): C 56 H 27 D5BN3: C, 88.18; H, 4.89; N, 5.51. Measured element content (%): C, 88.16; H, 4.84; N, 5.59.

[0231] Synthesis Example 12: Synthesis of Compound 302

[0232]

[0233] DD-83 was replaced with an equal molar amount of GG-302. The other steps were the same as those in Synthesis Example 8 to obtain Compound 302 (7.22 g, 36.20% yield). HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum m / z: 664.2584 (theoretical value: 664.2595). Theoretical element content (%): C 46 H 21 D5BN5: C, 83.13; H, 4.70; N, 10.54. Measured element content (%): C, 83.11; H, 4.76; N, 10.52.

[0234] Synthesis Example 13: Synthesis of Compound 308

[0235]

[0236] DD-152 was replaced with an equal molar amount of EE-308, and DD-83 was replaced with an equal molar amount of DD-152. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 308 (9.41 g, 34.27% yield). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum: m / z: 914.3617 (theoretical value: 914.3629). Theoretical element content (%): C 68 H 35 D5BN3: C, 89.27; H, 4.96; N, 4.59. Measured element content (%): C, 89.25; H, 4.99; N, 4.56.

[0237] Synthesis Example 14: Synthesis of Compound 310

[0238]

[0239] Under nitrogen, compound aa-310 (48.75 g, 150 mmol), compound bb-310 (48.60 g, 300 mmol), potassium carbonate (62.20 g, 450 mmol), and palladium acetate (1.36 g, 6 mmol) were dissolved in 3000 mL of a 2:1:1 mixture of toluene / ethanol / water. The mixture was stirred and heated under reflux for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added, and extraction was performed with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The product was recrystallized from toluene / methanol (9:1 volume ratio) to obtain intermediate EE-310 (42.68 g, 71.22% yield). The solid purity was ≥99.86% as determined by HPLC. Mass spectrum: m / z: 399.1976 (theoretical value: 399.1987).

[0240] DD-152 was replaced with an equal molar amount of EE-310, and DD-83 was replaced with an equal molar amount of DD-152. The remaining steps were the same as those in Synthesis Example 8 to obtain compound 310 (9.23 g, 34.38% yield). The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 894.3956 (theoretical value: 894.3942). Theoretical element content (%): C 66 H 39 D5BN3: C, 88.58; H, 5.52; N, 4.70. Measured element content (%): C, 88.56; H, 5.51; N, 4.75.

[0241] Synthesis Example 15: Synthesis of Compound 327

[0242]

[0243] DD-152 was replaced with an equal molar amount of EE-327, and DD-83 was replaced with an equal molar amount of DD-152. The remaining steps were the same as those in Synthesis Example 8 to obtain compound 327 (8.08 g, 35.31% yield). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 762.3019 (theoretical value: 762.3003). Theoretical element content (%): C 56 H 27 D5BN3: C, 88.18; H, 4.89; N, 5.51. Measured element content (%): C, 88.15; H, 4.85; N, 5.56.

[0244] Synthesis Example 16: Synthesis of Compound 329

[0245]

[0246] Substituting DD-152 with an equal molar amount of EE-329 and DD-83 with an equal molar amount of DD-152, and following the same procedures as in Example 8, compound 329 (7.01 g, 35.14% yield) was obtained. HPLC analysis revealed a solid purity of ≥99.92%. Mass spectrum: m / z: 664.2585 (theoretical value: 664.2595). Theoretical element content (%): C 46 H 21 D5BN5: C, 83.13; H, 4.70; N, 10.54. Measured element content (%): C, 83.18; H, 4.72; N, 10.50.

[0247] Synthesis Example 17: Synthesis of Compound 330

[0248]

[0249] Compound AA-274 (31.65 g, 150 mmol), compound BB-83 (22.85 g, 180 mmol), and potassium carbonate (37.32 g, 270 mmol) were dissolved in 675 mL of a 4:1 volume ratio mixture of THF and water. Pd(PPh3)4 (5.20 g, 4.5 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate CC-274 (30.16 g, 94.31% yield). HPLC analysis of the solid showed a purity of ≥99.82%. Mass spectrum: m / z: 213.0829 (theoretical value: 213.0814).

[0250] Compound CC-274 (21.32 g, 100 mmol) was dissolved in 335 mL of tetrahydrofuran. Lithium diisopropylamide (LDA, 50 mL, 100 mmol, 2 M solution in tetrahydrofuran) was added dropwise at -20°C under nitrogen. Stirring was continued for 1 hour, followed by the addition of elemental iodine (25.38 g, 100 mmol). The mixture was allowed to return to room temperature and stirred for another 4 hours. After completion of the reaction, the mixture was washed with sodium thiosulfate solution and dichloromethane. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate DD-274 (30.03 g, 88.55% yield). HPLC analysis of the solid showed a purity of ≥99.85%. Mass spectrum: m / z: 338.9790 (theoretical value: 338.9780).

[0251] Intermediate DD-274 (27.13 g, 80 mmol), compound DD-83 (80.47 g, 288 mmol), and cesium carbonate (117.30 g, 360 mmol) were dissolved in DMF (3000 mL) and refluxed under nitrogen for 9 hours. After completion of the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate HH-330 (83.34 g, 93.23% yield). HPLC analysis of the solid showed a purity of ≥99.79%. Mass spectrum: m / z: 1116.5568 (theoretical value: 1116.5554).

[0252] Intermediate HH-330 (33.52 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). n-Butyllithium (18 mL, 45 mmol, 2.5 M solution in n-hexane) was added dropwise at 0°C under nitrogen. The mixture was then heated to 70°C and stirred for 2 hours. BBr (5.75 mL, 60 mmol) was added dropwise after cooling to 0°C. The reaction system was returned to room temperature and stirred for 1 hour. N,N-Diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0°C. The reaction system was heated to 150°C and stirred for 12 hours. After completion of the reaction, the reaction was quenched with 51 mL of methanol and washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain compound 330 (10.48 g, 34.97% yield). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 998.6457 (theoretical value: 998.6446). Theoretical element content (%) C 72 H 71 D5BN3: C, 86.54; H, 8.17; N, 4.21. Measured element content (%): C, 86.58; H, 8.11; N, 4.22.

[0253] Synthesis Example 18: Synthesis of Compound 331

[0254]

[0255] Substituting DD-152 with an equal molar amount of GG-278, the remaining steps were the same as those in Synthesis Example 8 to obtain compound 331 (10.76 g, 34.52% yield). HPLC analysis of the solid showed a purity of ≥99.96%. Mass spectrum: m / z: 1038.5829 (theoretical value: 1038.5820). Theoretical element content (%): C 76 H 63 D5BN3: C, 87.84; H, 7.08; N, 4.04. Measured element content (%): C, 87.81; H, 7.05; N, 4.09.

[0256] Synthesis Example 19: Synthesis of Compound 357

[0257]

[0258] Substituting BB-83 with an equal molar amount of BB-357 and DD-83 with an equal molar amount of DD-152, the remaining steps were the same as those in Example 17 to obtain compound 357 (7.79 g, 35.15% yield). HPLC analysis of the solid showed a purity of ≥99.97%. Mass spectrum: m / z: 738.3018 (theoretical value: 738.3003). Theoretical element content (%): C 54 H 27 D5BN3: C, 87.80; H, 5.05; N, 5.69. Measured element content (%): C, 87.81; H, 5.08; N, 5.64.

[0259] Synthesis Example 20: Synthesis of Compound 368

[0260]

[0261] BB-83 was replaced with an equal molar amount of BB-368. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 368 (10.07 g, 34.86% yield). HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum m / z: 962.5517 (theoretical value: 962.5507). Theoretical element content (%): C 70 H 59 D5BN3: C, 87.29; H, 7.22; N, 4.36. Measured element content (%): C, 87.28; H, 7.27; N, 4.33.

[0262] Synthesis Example 21: Synthesis of Compound 405

[0263]

[0264] BB-83 was replaced with an equal molar amount of BB-405. The other steps were the same as those in Synthesis Example 8 to obtain Compound 405 (9.71 g, 34.47% yield). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 938.5483 (theoretical value: 938.5476). Theoretical element content (%): C 68 H 55 D7BN3: C, 86.97; H, 7.40; N, 4.47. Measured element content (%): C, 86.92; H, 7.42; N, 4.49.

[0265] Synthesis Example 22: Synthesis of Compound 420

[0266]

[0267]

[0268] Compound aa-420 (42.03 g, 150 mmol) was dissolved in 680 mL of THF and maintained at -78°C using a dry ice-acetone bath. 66 mL (165 mmol) of 2.5M n-BuLi was added dropwise. One hour later, 18.71 g (180 mmol) of trimethyl phosphate was added dropwise. After the reaction was complete, the mixture was warmed to room temperature, the solvent was removed by distillation, and the mixture was extracted with 215 mL of water and 215 mL of ethylamine. The solvent was evaporated and the mixture was recrystallized from petroleum ether / dichloromethane to obtain intermediate BB-420 (32.98 g, 89.69% yield).

[0269] BB-83 was replaced with an equal molar amount of BB-420, and DD-83 was replaced with an equal molar amount of GG-420. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 420 (11.13 g, 34.07% yield). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 1088.4511 (theoretical value: 1088.4504). Theoretical element content (%): C 77 H 41 D7BN7: C, 84.92; H, 5.09; N, 9.00. Measured element content (%): C, 84.99; H, 5.03; N, 9.01.

[0270] Synthesis Example 23: Synthesis of Compound 447

[0271]

[0272] HH-83 was replaced with an equal molar amount of HH-447. The remaining steps were the same as those in Synthesis Example 1 to obtain Compound 447 (6.34 g, 65.85% yield). HPLC analysis of the solid showed a purity of ≥99.98%. Mass spectrum m / z: 962.5519 (theoretical value: 962.5507). Theoretical element content (%): C 70 H 59 D5BN3: C, 87.29; H, 7.22; N, 4.36. Measured element content (%): C, 87.27; H, 7.28; N, 4.33.

[0273] Synthesis Example 24: Synthesis of Compound 479

[0274]

[0275] BB-83 was replaced with an equal molar amount of BB-479, DD-152 was replaced with DD-83, and DD-83 was replaced with DD-219. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 479 (9.02 g, 34.91% yield). HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum: m / z: 860.4895 (theoretical value: 860.4883). Theoretical element content (%): C 62 H 33 D 15 BN3: C, 86.49; H, 7.37; N, 4.88. Measured element content (%): C, 86.44; H, 7.33; N, 4.94.

[0276] Synthesis Example 25: Synthesis of Compound 503

[0277]

[0278] BB-83 was replaced with an equal molar amount of BB-503, and DD-83 was replaced with DD-219. The remaining steps were the same as those in Example 8 to obtain compound 503 (7.36 g, 34.42% yield). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum: m / z: 712.3279 (theoretical value: 712.3267). Theoretical element content (%): C 50 H 13 D 15 BN3O: C, 84.26; H, 6.08; N, 5.90. Measured element content (%): C, 84.21; H, 6.09; N, 5.94.

[0279] Synthesis Example 26: Synthesis of Compound 520

[0280]

[0281] BB-83 was replaced with an equal molar amount of BB-520, and DD-83 was replaced with GG-520. The remaining steps were the same as those in Example 8 to obtain Compound 520 (10.24 g, 34.75% yield). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 981.4875 (theoretical value: 981.4884). Theoretical element content (%): C 72 H 24 D 20 BN3: C, 88.06; H, 6.56; N, 4.28. Measured element content (%): C, 88.02; H, 6.54; N, 4.32.

[0282] Synthesis Example 27: Synthesis of Compound 562

[0283]

[0284] Substituting BB-83 with an equal molar amount of BB-562 and DD-152 with an equal molar amount of DD-219, the remaining steps were the same as those in Example 8 to obtain compound 562 (10.80 g, 35.21% yield). HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum: m / z: 1021.5318 (theoretical value: 1021.5306). Theoretical element content (%): C 71 H 56 D7BN4S: C, 83.42; H, 6.90; N, 5.48. Measured element content (%): C, 83.48; H, 6.85; N, 5.44.

[0285] Synthesis Example 28: Synthesis of Compound 571

[0286]

[0287] BB-83 was replaced with an equal molar amount of BB-520, and DD-152 was replaced with an equal molar amount of EE-571. The remaining steps were the same as those in Synthesis Example 8 to obtain Compound 571 (10.68 g, 34.09% yield). HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum: m / z: 1043.6119 (theoretical value: 1043.6134). Theoretical element content (%): C 76 H 58 D 10 BN3: C, 87.41; H, 7.53; N, 4.02. Measured element content (%): C, 87.44; H, 7.50; N, 4.04.

[0288] Synthesis Example 29: Synthesis of Compound 578

[0289]

[0290] DD-83 was replaced with an equal molar amount of DD-219. The remaining steps were the same as those in Synthesis Example 17 to obtain Compound 578 (7.26 g, 35.32% yield). HPLC analysis of the solid showed a purity of ≥99.99%. Mass spectrum: m / z: 684.4086 (theoretical value: 684.4071). Theoretical element content (%): C 48 HD 27 BN3: C, 84.20; H, 8.09; N, 6.14. Measured element content (%): C, 84.26; H, 8.04; N, 6.11.

[0291] Synthesis Example 30: Synthesis of Compound 585

[0292]

[0293] BB-83 was replaced with an equal molar amount of BB-585, and DD-83 was replaced with an equal molar amount of DD-219. The remaining steps were the same as those in Synthesis Example 17 to obtain Compound 585 (8.73 g, 35.14% yield). HPLC analysis of the solid showed a purity of ≥99.97%. Mass spectrum: m / z: 827.4476 (theoretical value: 827.4465). Theoretical element content (%): C 57 H 18 D 22 BN3Si: C, 82.68; H, 7.54; N, 5.08. Measured element content (%): C, 82.66; H, 7.59; N, 5.04.

[0294] Synthesis Example 31: Synthesis of Compound 593

[0295]

[0296] AA-274 was replaced with an equal molar amount of AA-593. The remaining steps were the same as those in Synthesis Example 17 to obtain Compound 593 (9.28 g, 34.88% yield). HPLC analysis of the solid showed a purity of ≥99.96%. Mass spectrum m / z: 886.5181 (theoretical value: 886.5194). Theoretical element content (%): C 64 H 55 D5BN3: C, 86.66; H, 7.39; N, 4.74. Measured element content (%): C, 86.61; H, 7.35; N, 4.79.

[0297] Synthesis Example 32: Synthesis of Compound 611

[0298]

[0299] Compound AA-611 (50.53 g, 150 mmol), compound BB-520 (51.67 g, 180 mmol), and potassium carbonate (37.32 g, 270 mmol) were dissolved in 675 mL of a 4:1 volume ratio mixture of THF and water. Pd(PPh3)4 (5.20 g, 4.5 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate CC-611 (39.22 g, 91.08% yield). HPLC analysis of the solid showed a purity of ≥99.80%. Mass spectrum: m / z: 285.9617 (theoretical value: 285.9605).

[0300] Intermediate CC-611 (28.71 g, 100 mmol), compound BB-83 (15.24 g, 120 mmol), and potassium carbonate (24.88 g, 180 mmol) were dissolved in 450 mL of a mixture of THF and water (volume ratio 4:1). Pd(PPh3)4 (3.47 g, 3.0 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate EE-611 (26.20 g, 90.57% yield). The solid purity was ≥99.84% as determined by HPLC. Mass spectrum: m / z: 289.1138 (theoretical value: 289.1127).

[0301] Intermediate EE-611 (23.14 g, 80 mmol) was dissolved in 270 mL of tetrahydrofuran. Lithium diisopropylamide (LDA, 40 mL, 80 mmol, 2 M solution in tetrahydrofuran) was added dropwise at -20°C under nitrogen. Stirring was maintained for 1 hour, followed by the addition of elemental iodine (20.30 g, 80 mmol). The mixture was allowed to return to room temperature and stirred for another 4 hours. After completion of the reaction, the mixture was washed with sodium thiosulfate solution and dichloromethane. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate FF-611 (29.61 g, 89.13% yield). The solid purity was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 415.0081 (theoretical value: 415.0093).

[0302] Intermediate FF-611 (20.76 g, 50 mmol), compound DD-83 (50.30 g, 180 mmol), and cesium carbonate (73.31 g, 225 mmol) were dissolved in DMF (1880 mL) and refluxed under nitrogen for 9 hours. After completion of the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate HH-611 (53.86 g, 90.26% yield). HPLC analysis of the solid showed a purity of ≥99.76%. Mass spectrum: m / z: 1192.5853 (theoretical value: 1192.5867).

[0303] Intermediate HH-611 (35.80 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). n-Butyllithium (18 mL, 45 mmol, 2.5 M solution in n-hexane) was added dropwise at 0°C under nitrogen. The mixture was then heated to 70°C and stirred for 2 hours. BBr (5.75 mL, 60 mmol) was added dropwise after cooling to 0°C. The reaction system was returned to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0°C. The reaction system was heated to 150°C and stirred for 12 hours. After completion of the reaction, the reaction was quenched with 51 mL of methanol and washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain compound 611 (11.21 g, 34.76% yield). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1074.6773 (theoretical value: 1074.6759). Theoretical element content (%) C 78 H 75 D5BN3: C, 87.12; H, 7.97; N, 3.91. Measured element content (%): C, 87.15; H, 7.91; N, 3.94.

[0304] Synthesis Example 33: Synthesis of Compound 616

[0305]

[0306] Compound AA-616 (41.40 g, 150 mmol), compound BB-83 (22.85 g, 180 mmol), and potassium carbonate (37.32 g, 270 mmol) were dissolved in 675 mL of a 4:1 volume ratio mixture of THF and water. Pd(PPh3)4 (5.20 g, 4.5 mmol) was added under nitrogen, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate CC-616 (32.18 g, 92.78% yield). HPLC analysis of the solid showed a purity of ≥99.82%. Mass spectrum: m / z: 231.0707 (theoretical value: 231.0719).

[0307] Intermediate CC-616 (23.12 g, 100 mmol) was dissolved in 340 mL of tetrahydrofuran. Lithium diisopropylamide (LDA, 50 mL, 100 mmol, 2 M solution in tetrahydrofuran) was added dropwise at -20°C under nitrogen. Stirring was continued for 1 hour, followed by the addition of elemental iodine (25.38 g, 100 mmol). The mixture was allowed to return to room temperature and stirred for another 4 hours. After completion of the reaction, the mixture was washed with sodium thiosulfate solution and dichloromethane. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate DD-616 (32.02 g, 89.66% yield). The solid purity was ≥99.89% as determined by HPLC. Mass spectrum: m / z: 356.9671 (theoretical value: 356.9686).

[0308] Intermediate DD-616 (17.86 g, 50 mmol), compound DD-83 (67.07 g, 240 mmol) and cesium carbonate (97.75 g, 300 mmol) were dissolved in DMF (2500 mL) and refluxed under nitrogen for 9 hours. After the reaction, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized with dichloromethane and methanol to obtain intermediate HH-616 (63.25 g, yield 90.69%). The solid purity was ≥ 100% by HPLC.

[0309] 99.87%. Mass spectrum m / z: 1393.7397 (theoretical value: 1393.7385).

[0310] Intermediate HH-616 (41.84 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). n-Butyllithium (18 mL, 45 mmol, 2.5 M solution in n-hexane) was added dropwise at 0°C under nitrogen. The mixture was then heated to 70°C and stirred for 2 hours. BBr (5.75 mL, 60 mmol) was added dropwise after cooling to 0°C. The reaction system was returned to room temperature and stirred for 1 hour. N,N-Diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0°C. The reaction system was heated to 150°C and stirred for 12 hours. After completion of the reaction, the reaction was quenched with 51 mL of methanol and washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain compound 616 (13.23 g, 34.55% yield). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1275.8289 (theoretical value: 1275.8277). Theoretical element content (%) C 92 H 94 D5BN4: C, 86.55; H, 8.21; N, 4.39. Measured element content (%): C, 86.58; H, 8.25; N, 4.38.

[0311] The following are other compounds used in the device preparation examples except the boron nitrogen heterocyclic compound represented by formula (I):

[0312]

[0313] A combined IVL test system was constructed by using test software, a computer, a K2400 digital source meter from Keithley, USA, and a PR788 spectrum scanning luminance meter from Photo Research, USA. The luminescence spectrum of the device prepared in the present invention was tested at atmospheric pressure and room temperature, as well as its luminescence performance at a current density of 10 mA / cm 2 The luminous efficiency at 100 nm was 0.1 1 / 4 ...

[0314] Comparative device preparation example 1: Comparative device 1

[0315] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0316] The following layers were deposited layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a, HT-12 and p-1 (mass ratio of 100:1) as a hole injection layer with a thickness of 10 nm; b, HT-12 as a hole transport layer with a thickness of 120 nm; c, GH-1, GH-2 and compound ref-1 (mass ratio of 66:33:1) as a light-emitting layer with a thickness of 30 nm; d, TPBi as a hole blocking layer with a thickness of 5 nm; e, BCP and Liq (mass ratio of 1:1) as an electron transport layer with a thickness of 25 nm; f, LiF as an electron injection layer with a thickness of 1 nm; g, Mg and Ag (mass ratio of 1:9) as a cathode with a thickness of 15 nm; h: CP-1 as a covering layer with a thickness of 75 nm.

[0317] Comparative device preparation examples 2 to 8: Comparative devices 2 to 8

[0318] Replace ref-1 in the light-emitting layer with ref-2, ref-3, ref-4, ref-5, ref-6, ref-7, and ref-8 in sequence. The other steps are the same as those in comparative device preparation example 1 to obtain comparative devices 2 to 8.

[0319] Device Preparation Examples 1-33: Light-Emitting Devices 1-33

[0320] The ref-1 in the light-emitting layer is replaced with compound 83, compound 104, compound 126, compound 132, compound 152, compound 164, compound 219, compound 274, compound 278, compound 280, compound 299, compound 302, compound 308, compound 310, compound 327, compound 329, compound 330, compound 331, compound 357, compound 368, compound 405, compound 420, compound 447, compound 479, compound 503, compound 520, compound 562, compound 571, compound 578, compound 585, compound 593, compound 611, and compound 616 in sequence, and the other steps are the same as those in comparative device preparation example 1, to obtain light-emitting devices 1 to 33.

[0321] Table 1

[0322]

[0323]

[0324] Comparative device preparation example 9: Comparative device 9

[0325] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0326] The following layers were deposited layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a. HT-12 and p-1 (mass ratio of 100:1) as a hole injection layer with a thickness of 10 nm; b. HT-12 as a hole transport layer with a thickness of 120 nm; c. GH-1, GH-2, Ir(ppy)3 and compound ref-1 (mass ratio of 64:32:3:1) as a light-emitting layer with a thickness of 30 nm; d. TPBi as a hole blocking layer with a thickness of 5 nm; e. BCP and Liq (mass ratio of 1:1) as an electron transport layer with a thickness of 25 nm; f. LiF as an electron injection layer with a thickness of 1 nm; g. Mg and Ag (mass ratio of 1:9) as a cathode with a thickness of 15 nm; h. CP-1 as a covering layer with a thickness of 75 nm.

[0327] Comparative device preparation examples 10 to 16: Comparative devices 10 to 16

[0328] Replace ref-1 in the light-emitting layer with ref-2, ref-3, ref-4, ref-5, ref-6, ref-7, and ref-8 in sequence, and the other steps are the same as those in comparative device preparation example 9 to obtain comparative devices 10 to 16.

[0329] Device Preparation Examples 34-66: Light-Emitting Devices 34-66

[0330] The ref-1 in the light-emitting layer is replaced with compound 83, compound 104, compound 126, compound 132, compound 152, compound 164, compound 219, compound 274, compound 278, compound 280, compound 299, compound 302, compound 308, compound 310, compound 327, compound 329, compound 330, compound 331, compound 357, compound 368, compound 405, compound 420, compound 447, compound 479, compound 503, compound 520, compound 562, compound 571, compound 578, compound 585, compound 593, compound 611, and compound 616 in sequence, and the other steps are the same as those in comparative device preparation example 9 to obtain light-emitting devices 34 to 66.

[0331] Table 2

[0332]

[0333]

[0334] The device data in Tables 1 and 2 show that the boron-nitrogen heterocyclic compound provided by the present invention is used as a doping material for the light-emitting layer. Compared with the prior art, the half-maximum width of the light emitted by the device is narrowed, thereby improving the color purity of the device, while also increasing the luminous efficiency and service life of the device.

[0335] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A boron-nitrogen heterocyclic compound, characterized in that The boron-nitrogen heterocyclic compound has a structure shown in formula (I): Wherein, the ring E, ring F, ring G, and ring H are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; Said X1, X2, X3 are independently selected from CR or nitrogen atoms, and at least two of them are not selected from nitrogen atoms; Wherein, at least one R is selected from the group represented by formula (II-A) or formula (II-B): Wherein, the ring P and ring Q are independently selected from one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The Ar is selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The L1 and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof; Furthermore, at least one R is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a combination thereof; The remaining R is selected from one of hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C10 cycloalkyl group; The condition is that the molecule contains at least one deuterium atom.

2. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that The ring E, ring F, ring G, ring H, ring P, and ring Q are independently selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted benzocyclopropane ring, a substituted or unsubstituted benzocyclobutane ring, a substituted or unsubstituted benzocyclopentane ring, a substituted or unsubstituted benzocyclohexane ring, a substituted or unsubstituted benzocycloheptane ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted quinoline ring, and a substituted or unsubstituted isoquinoline ring.

3. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that The formula (II-A) is selected from one of the following groups: wherein each occurrence of a2 is the same or different selected from 0, 1, 2 or 3; each occurrence of b2 is the same or different selected from 0, 1, 2, 3 or 4; each occurrence of c2 is the same or different selected from 0, 1 or 2; The R 21 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring; The Ar is selected from trimethylsilyl, triphenylsilyl, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, or one of the following groups: Each occurrence of a3 is selected from 0, 1, 2, 3, 4, or 5, the same or different; each occurrence of b3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, the same or different; each occurrence of c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, the same or different; each occurrence of d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, the same or different; each occurrence of e3 is selected from 0, 1, 2 or 3; each time f3 occurs, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time g3 occurs, it is selected from 0, 1 or 2 in the same or different manner; each time h3 occurs, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time i3 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time j3 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner; The R 31 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring; The R 32 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group; The X3 is selected from O, S, CR 33 R 34 or NR 35 , the R 33 、R 34 、R 35 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 33 、R 34 Can be connected to form a ring; The R 36 One selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The X4 is selected from O, S or NR 37 , the R 37 One selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The L1 and L2 are independently selected from a single bond and one of the following groups: The a 101 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said c 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 101 Each occurrence is identically or differently selected from 0, 1 or 2; said e 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said f 101 Each occurrence is identically or differently selected from 0, 1, 2 or 3; The R 101 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring; The R 102 Each occurrence is identically or differently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group.

4. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that The formula (II-B) is selected from one of the following groups: Each occurrence of a4 is the same or different and is selected from 0, 1, 2, 3 or 4; each occurrence of b4 is the same or different and is selected from 0, 1, 2, 3, 4 or 5; each occurrence of c4 is the same or different and is selected from 0, 1 or 2; The R 41 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring; The L1 is as described in claim 3.

5. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that At least one R is selected from one of the following groups: Each occurrence of a1 is the same or different selected from 0, 1, 2, 3, 4, or 5; each occurrence of b1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of c1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of d1 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; each occurrence of e1 is the same or different selected from 0, 1, 2 or 3; each time f1 occurs, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time g1 occurs, it is selected from 0, 1 or 2 in the same or different manner; each time h1 occurs, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time i1 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time j1 occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner; The R 11 Each occurrence is identically or differently selected from one of the following: a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring; The R 12 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group; The X0 is selected from O, S or CR 10 R 20 , the R 10 、R 20 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 10 、R 20 Can be connected to form a ring; The X1 is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 、R 15 is independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring with a substituted or unsubstituted C3-C7 aliphatic ring, wherein R 13 、R 14 Can be connected to form a ring; The R 16 One selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The X2 is selected from O, S or NR 17 , the R 17 One selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring.

6. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that At least one R is selected from one of the following groups:

7. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that At least one of the rings E, F, G and H contains a deuterium atom.

8. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that The boron-nitrogen heterocyclic compound has a structure shown in formula (IA) or formula (IB): wherein R is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by condensing a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof; The ring E, ring F, ring G, ring H, ring P, ring Q, Ar, L1, and L2 are as described in claim 1.

9. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that The boron-nitrogen heterocyclic compound is selected from one of the following compounds:

10. An organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that: The light-emitting layer contains the boron-nitrogen heterocyclic compound according to any one of claims 1 to 9.

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