Boron-nitrogen-containing organic compound, application thereof and organic electroluminescent device

Abstract

The invention provides an organic compound and application thereof, and an organic electroluminescent device comprising the same, the organic compound has a structure as shown in a formula (I), through the design of a molecular structure, the organic compound has good TADF characteristics, meanwhile, the carrier transport performance and stability are remarkably improved, and the organic compound is endowed with excellent photoelectric properties. The organic compound is used for a light-emitting layer of an organic electroluminescent device, so that the device has higher light-emitting efficiency and excellent color purity, the external quantum efficiency is improved, and the driving voltage is reduced. # imgabs0 #

Description

Technical Field

[0001] The invention relates to a boron-nitrogen-containing organic compound, belonging to the technical field of organic luminescent materials. The invention also relates to the application of the compound in an organic electroluminescent device and the organic electroluminescent device. Background Art

[0002] With the progress and development of social sciences, display technology has become crucial in people's lives. Organic light-emitting diodes (OLEDs) have become one of the mainstream display devices due to their many advantages such as flexibility, bendability, self-luminescence, high contrast, large size, and low power consumption.

[0003] The luminescence mechanism of OLED is that electrons and holes recombine to form excitons under electrical excitation. Excitons obey probability statistical distribution, with singlet excitons accounting for about 25% and triplet excitons accounting for about 75%. The first generation of luminescence technology is collectively referred to as fluorescence technology, which uses singlet excitons to emit light, and the efficiency is low; the second generation of luminescence technology is collectively referred to as phosphorescence technology, which uses triplet excitons to emit light, and theoretically can achieve 100% internal quantum efficiency, but the heavy metals required to construct phosphorescent dyes are not only expensive but also pollute the environment. Therefore, the third generation of thermally excited delayed fluorescence technology constructed using organic small molecules is currently widely used. When the singlet-triplet energy level difference is very small, the triplet exciton can reverse intersystem crossing to the singlet state, and then return to the ground state to emit light. Among them, red and green dyes as the three primary colors have become the mainstream of current commercial display devices due to their high electroluminescence efficiency and low power consumption. However, the chromaticity and life of blue light materials do not meet the current commercial display requirements. Blue light devices still use the first generation of traditional fluorescent materials to achieve high color purity and long device life.

[0004] At present, optoelectronic devices using organic materials are becoming more and more popular. The vast majority of materials used to manufacture such optoelectronic devices are organic materials, and the price of organic materials is relatively low, making organic devices more cost-effective than inorganic devices. At present, in organic electroluminescent devices in the field of display and lighting, red fluorescence is generally used in combination with red and green phosphorescent materials. Recently, patents CN112645968A, CN112174992A, etc. disclose a class of multiple resonance fluorescent compounds based on TADF (Thermally Activated Delayed Fluorescence) of BN resonance structure, and such compounds are composed of B, N and benzene rings to form a rigid polycyclic aromatic skeleton. Nitrogen atoms have a resonance effect opposite to that of boron atoms, and the opposite resonance effect will be enhanced at their para position, so this effect can clearly separate HOMO and LUMO orbits, and thus have certain TADF characteristics. Although this series of materials has broad application prospects, due to the serious intramolecular rotation, this type of material will lose energy due to vibrational-rotational energy levels, resulting in low external quantum efficiency; even if the dimethylfluorene structure is used in some compound structures to suppress the intramolecular rotational energy level as disclosed in the prior art, the device life is poor due to the unbalanced charge transfer. Therefore, the existing organic electroluminescent materials still have a lot of room for improvement in luminescence performance, and the industry urgently needs to develop new luminescent material systems to meet commercial needs. Summary of the invention

[0005] In order to solve the above technical problems, the purpose of the present invention is to provide a boron-nitrogen-containing organic compound and its application, and an organic electroluminescent device containing the same. Through the design of the molecular structure, the organic compound has higher carrier mobility and stability. It is used in an organic electroluminescent device to improve the luminous efficiency and life of the device. Specifically, the present invention provides a boron-nitrogen-containing organic compound having a structure shown in formula (I):

[0006]

[0007] Wherein, Ring A, Ring B, and Ring C are each independently selected from any one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, Ar 1 ,Ar 2 Independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0008] Ar 1 ,Ar 2 At least one of them has a structure of formula (b), and / or at least one of ring A, ring B, and ring C has a substituent of the structure of formula (b),

[0009]

[0010] Ring N and ring M each independently represent a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0011] L represents a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;

[0012] Ra and Rb each independently represent one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, and substituted or unsubstituted C3-C20 cycloalkyl;

[0013] The above-mentioned substituents are each independently selected from any one of C1~C20 chain alkyl, C1~C20 chain halogenated alkyl, C2~C20 alkenyl, C3~C20 cycloalkyl, C1~C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6~C30 aryl, C3~C30 heteroaryl, or a combination of at least two thereof; the * indicates the connection site.

[0014] The parent core structure of the compound of the present invention containing boron nitrogen structure (i.e., the basic skeleton structure of formula (I)) is very important, so that the triplet energy level of such compounds is suitable, suitable for use as TADF luminescent material. In the parent core structure, the planarity of the bicyclic rings and rings A, B, and C containing nitrogen and boron is more favorable for maintaining the triplet energy level. In the present invention, it is very important that there is at least one group of formula (b) in the substituent. The inventor has found that such a group is to connect the BN aromatic ring skeleton to the biphenyl branched structure, while enhancing the charge transfer ability, the charge accumulation in the material is suppressed, and the voltage drop, the improvement of the external quantum efficiency and the extension of the device life are achieved. More specifically, the arylene or heteroarylene of the above-mentioned L part enhances the charge transfer ability, while suppressing the charge accumulation in the material, and also due to its special steric effect affects the film-forming properties, so that the formed film can achieve better stability, thereby directly improving the device life.

[0015] It should be noted that, unless otherwise defined below, the meanings of all technical terms and scientific terms used herein are intended to be the same as those generally understood by those skilled in the art. Reference to the technology used herein is intended to refer to the technology generally understood in the art, including those changes in technology or replacement of equivalent technology that are obvious to those skilled in the art. Although it is believed that the following terms are well understood by those skilled in the art, the following definitions are still set forth to better explain the present invention.

[0016] In this specification, the expression of Ca to Cb indicates that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent. When describing C1 to C30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.

[0017] The terms "comprises," "comprising," "having," "containing," or "involving" and other variations thereof herein are inclusive or open-ended and do not exclude additional unrecited elements or method steps.

[0018] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes 12 C. 13 C, etc., no further details.

[0019] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0020] As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O and S and the remaining ring atoms being C.

[0021] As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl and alkyl groups are as defined herein.

[0022] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0023] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced by a selection from the indicated group, provided that the normal valence of the designated atom in the present context is not exceeded and the substitution forms a stable compound. Combinations of substituents and / or variables are permitted only if such combinations form stable compounds.

[0024] If substituents are described as being "independently selected" from a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.

[0025] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0026] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0027] When a bond to a substituent is shown to pass through a bond connecting two atoms in a ring, then such substituent may be bonded to any ring atom in the substitutable ring.

[0028] The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

[0029] In the structural formula disclosed in this specification, the expression of the ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0030] The above-mentioned C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention, unless otherwise specified, are aromatic groups satisfying the π conjugated system, including both monocyclic residues and condensed ring residues. The so-called monocyclic residue refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; a fused ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing the ring edge, such as naphthyl, anthracenyl, phenanthryl, etc.; a monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or composed of at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0031] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, and more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aromatic ring in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl.

[0032] In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[0033] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, which can be a nitrogen-containing heteroaromatic group, an oxygen-containing heteroaromatic group, a sulfur-containing heteroaromatic group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridinyl , benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1, 1,2,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaromatic rings in the present invention include heteroaromatic rings of furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole.

[0034] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridine yl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidazinyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or / and fusion.

[0035] In the present invention, the aryl ether group and heteroaryl ether group include the above-mentioned aryl group and heteroaryl group and oxygen. 2 A group consisting of one or two H in the group.

[0036] In this specification, the chain alkyl group includes both straight-chain and branched-chain alkyl groups. Examples of C1-C20 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc. Examples of C1-C20 chain halogenated alkyl groups include: trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, etc.

[0037] In the present specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

[0038] The C2-C20 alkenyl group includes both straight-chain and branched alkenyl groups, and the number of carbon atoms of the alkenyl group is preferably 2 to 10. Specific examples include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0039] The C2-C20 alkynyl group includes the concepts of both straight-chain and branched alkenyl groups, and the number of carbon atoms of the alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0040] In the present specification, an alkoxy group refers to a group consisting of the above-mentioned chain alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0041] Examples of C1-C20 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0042] In the present specification, examples of C1-C20 silyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two or three hydrogen atoms on the silyl group with the above-mentioned chain alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0043] In a preferred embodiment of the present invention, Ar 1 ,Ar 2 One of them is a structure of formula (b) or Ar 1 ,Ar 2 All of them are of formula (b);

[0044] Ra and Rb are one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C3-C10 cycloalkyl. Ra and Rb are preferably one of hydrogen, substituted or unsubstituted C1-C4 chain alkyl, and substituted or unsubstituted C3-C10 cycloalkyl.

[0045] Preferably, the structure of formula (b) is a structure as shown in formula (b-1):

[0046]

[0047] Wherein, L represents one of a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group;

[0048] X 1 -X 5 and X 1’ -X 5’ Represents CR 0 or N, where R 0 are independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl,

[0049] The above-mentioned substituents are each independently selected from any one or a combination of at least two of C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl or C3-C30 heteroaryl; the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond, and the * indicates the connection site.

[0050] In a preferred embodiment of the present invention, in formula (b-1), R 0 are independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl,

[0051] Preferably, R 0Each is independently selected from one of hydrogen, C1-C6 chain alkyl, C1-C6 chain halogenated alkyl, C2-C6 alkenyl, C6-C12 aryl, and C3-C12 heteroaryl;

[0052] More preferably, R 0 Each is independently selected from one of hydrogen, C1-C6 chain alkyl, C2-C6 alkenyl, C6-C12 aryl and C3-C12 heteroaryl.

[0053] In a preferred embodiment of the present invention, L represents a substituted or unsubstituted C6-C12 arylene group, a substituted or unsubstituted C3-C12 heteroarylene group;

[0054] Preferably, L is selected from one or a combination of at least two of the following substituted or unsubstituted groups:

[0055]

[0056] Y 1 , Y 2 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 , R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl;

[0057] More preferably, L is selected from one of the following substituted or unsubstituted groups:

[0058]

[0059] The above-mentioned substituents are each independently selected from any one or a combination of at least two of C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl or C3-C30 heteroaryl; the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond, and the * indicates the connection site.

[0060] In a preferred embodiment of the present invention, the ring A and the ring B each independently have a structure as shown in formula (C) or formula (D):

[0061]

[0062] The dashed single or double bonds indicate the fusion positions of the groups;

[0063] Z 1 ~Z 8 Each independently is CR 2 or N; R 2 Each is independently selected from hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, C3-C30 heteroaryl; adjacent R 2 are not connected or connected to form a ring through chemical bonds; the R 2 Not connected to adjacent ring structures or connected to form a ring through chemical bonds;

[0064] Preferably, R 2 Selected from the following groups:

[0065]

[0066] * indicates the connection site;

[0067] X is selected from O, S, NR 21 or CR 22 R 23 ;

[0068] R 21 , R 22 , R 23 Each is independently selected from any one of a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group,

[0069] The substituents mentioned above are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group.

[0070] In a preferred embodiment of the present invention, the organic compound has a structure shown in formula (II-1) to formula (II-5):

[0071]

[0072]

[0073] Among them, Z 1 ~Z 8 Each independently has the same limitations as above;

[0074] Z 1’ ~Z 4’ Each independently is CR2 or N; R 2 Each is independently selected from hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, C3-C30 heteroaryl; adjacent R 2 are not connected or connected to form a ring through chemical bonds; the R 2 Not connected to adjacent ring structures or connected to form a ring through chemical bonds;

[0075] Z 9 ~Z 17 , Z 9’ ~Z 12’ Independently selected from CR 4 or N, R 4 Each of the following groups is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0076] R 3 is selected from substituted or unsubstituted C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, R 3 Not connected to adjacent ring structures or connected to form a ring through chemical bonds;

[0077] E represents the following group,

[0078]

[0079] Wavy lines indicate junction sites;

[0080] The substituents mentioned above are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group.

[0081] Furthermore, the organic compound of the present invention can preferably include the specific structural compounds M1 to M161 shown below, which are only representative and do not limit the scope of the present invention:

[0082] The structure shown in any one of M1-M161:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] The preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, it is suitable for mass production and amplification, and it is very suitable for industrial application.

[0093] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0094] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, and an organic electroluminescent device is further preferred.

[0095] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0096] Preferably, the organic compound is used as a luminescent dye of a light-emitting layer in an organic electroluminescent device.

[0097] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode; the organic layer comprises at least one organic compound as described in the first aspect, preferably comprises at least one organic compound with the structure shown in the above-mentioned present invention.

[0098] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound as described in the first aspect, and preferably comprises at least one organic compound having the structure shown in the above-mentioned present invention.

[0099] Preferably, the light-emitting layer comprises a host material and a dye, and the dye comprises at least one organic compound as described in the first aspect, and further preferably comprises at least one organic compound having the structure shown in the present invention.

[0100] As a preferred technical solution of the present invention, the organic compound, when used as a dye of the light-emitting layer, especially as a luminescent dye, has good luminescent properties, can improve the life and external quantum efficiency of the device, and make the device have high luminescent efficiency and better color purity, which can meet the current requirements of panel and display manufacturers for high-performance materials.

[0101] The organic compound provided by the present invention can be used as a TADF material, as a dye (guest material) of the light-emitting layer, and is suitable for organic electroluminescent devices with a TADF mechanism or an organic electroluminescent device with a TASF (thermally activated sensitized fluorescence) mechanism, and can effectively improve the performance of the device. Its good carrier transport performance and high luminous efficiency have potential applications in solving the efficiency roll-off of OLED devices at high current density and extending the life of the device.

[0102] Preferably, the organic layer further comprises any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, or a combination of at least two thereof.

[0103] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0104] Compared with the prior art, the present invention has the following beneficial effects:

[0105] In the organic compound provided by the present invention, through the design of the molecular structure, especially through the interaction between the B-containing aromatic skeleton in the parent core structure and the specific N-containing heterocycle and the aromatic ring or heteroaromatic ring structure substituted with phenylisopropyl in structure (b), the organic compound has good TADF characteristics and significantly improved carrier transport performance and stability, giving it excellent photoelectric performance. The organic compound is used in the light-emitting layer of an organic electroluminescent device, and is particularly suitable as a luminescent dye, so that the device has higher luminous efficiency and excellent color purity, improves external quantum efficiency, prolongs life, and reduces driving voltage. DETAILED DESCRIPTION

[0106] The technical solution of the present invention is further described in more detail below.

[0107] Synthesis methods of compounds

[0108] The compound of the present invention can be obtained by a known method, for example, by synthesis by a known organic synthesis method.

[0109] The organic compound represented by Formula I of the present invention can be synthesized by known organic synthesis methods. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods.

[0110] For example, the organic compound can be prepared by the following synthetic route:

[0111]

[0112]

[0113]

[0114]

[0115] The specific preparation method of the organic compound of the present invention will be described in detail in the specification by taking multiple preparation examples and synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that obtaining the organic compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art can also select other methods or routes to obtain the organic compound proposed in the present invention.

[0116] The compounds not mentioned in the present invention are all raw materials obtained from commercial sources, or are prepared by themselves according to known methods. The solvents and reagents used in the present invention can all be purchased from the chemical product market.

[0117] In addition, although representative exemplary synthetic routes of the compounds of the present invention are described in the examples, those skilled in the art can also obtain the compounds by other methods known in the art.

[0118] Organic EL devices

[0119] The OLED structure of the present invention can refer to the known technology, for example, the organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer between the electrodes. The organic layer can be divided into multiple regions, for example, including a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer comprises at least one boron-containing organic compound as described in the first aspect, and further preferably comprises at least one organic compound having the structure shown in the present invention.

[0120] In a preferred technical solution, the organic electroluminescent device includes a substrate, and a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode sequentially arranged on the substrate; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer sequentially arranged, and the hole injection layer is in contact with the first electrode. The organic layer (preferably the light-emitting layer) comprises at least one organic compound as described in the first aspect, and further preferably comprises at least one organic compound having the structure shown in the present invention.

[0121] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0122] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like and any combination thereof can be used.

[0123] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0124] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0125] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0126]

[0127]

[0128]

[0129] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0130]

[0131] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0132] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0133] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0134]

[0135] In one aspect of the present invention, the barrier layer around the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0136]

[0137]

[0138]

[0139]

[0140] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0141] The OLED organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0142] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0143]

[0144]

[0145]

[0146]

[0147] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0148] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li 2 O、Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Yb.

[0149] Specific embodiments are described below. Those skilled in the art should understand that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0150] Example

[0151] Synthesis of compounds

[0152] The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art can also select other methods or routes to obtain the compound proposed by the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained through commercial channels, or are made by these raw materials according to known methods. The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, tert-butylbenzene, boron tribromide, carbazole, diphenylamine, and other chemical reagents, can all be purchased from the domestic chemical product market, such as from Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. The analysis and detection of the intermediates and compounds in the present invention uses an ABSCIEX mass spectrometer (4000QTRAP). The structural analysis and detection of the intermediates and compounds in the present invention uses a gas chromatography-mass spectrometer (GC-MS, Shimadzu QP2010 SE).

[0153] Synthesis of the compounds of the present invention

[0154] Preparation Example 1: Synthesis of Intermediate A1

[0155]

[0156] α-Cinnamyl phenol (50 g, 235.52 mmol), triethylamine (25.75 g, 353.29 mmol) and 300 mL of dichloromethane were added to a 1 L single-necked flask. Trifluoromethanesulfonate (86.38 g, 306.18 mmol) was slowly added at -50 °C under nitrogen protection. After the addition was completed, the reaction was restored to room temperature for 1 hour. TLC detection showed that the raw material reaction was complete. 300 mL of water was added, the washing fraction was dried and concentrated, and purified by vacuum distillation to obtain 76.62 g of the target intermediate with a yield of 94.5%.

[0157] Structural characterization: MS:344.07 / 344.45.

[0158] Preparation Example 2: Synthesis of Intermediate B1

[0159]

[0160] The intermediate A1 (30 g, 87.12 mmol), 4-aminophenylboronic acid (11.93 g, 87.12 mmol), tetrakistriphenylphosphine palladium (2 g, 1.74 mmol), and potassium carbonate (15.65 g, 113.26 mmol) were added into a 1 L single-necked flask, and 300 mL of a 5:1 mixed solvent of 1,4-dioxane and water was added. The mixture was reacted at 100 °C under nitrogen protection for 10 hours, and then the heating was stopped. 200 mL of dichloromethane was added for dilution, the separated liquid was washed with water, dried, concentrated, and purified by reduced pressure distillation to obtain 23.31 g of the target product intermediate B1 with a yield of 93.1%.

[0161] Structural characterization: MS:287.10 / 287.54.

[0162] Preparation Example 3: Synthesis of Intermediate B2

[0163]

[0164] Referring to the synthetic method of intermediate B1, intermediate B2 (18.67 g, 74.3%) was synthesized.

[0165] Structural characterization: MS:288.16 / 288.39.

[0166] Preparation Example 4: Synthesis of Intermediate C1

[0167]

[0168] The raw material 4-tert-butyl-2,6-dibromochlorobenzene (25 g, 76.58 mmol) and intermediate B1 (22.01 g, 76.58 mmol) were added to a 1L single-necked flask, and the catalyst 1,1'-bis(diphenylphosphinoferrocene)palladium dichloride Pd(dppf)Cl was added. 2(1.53mmol, 1.11g), sodium tert-butoxide (99.55mmol, 10g), add 300mL of toluene, react at 100℃ under nitrogen protection for 10h, stop heating, wash with water, concentrate, and purify by reduced pressure distillation to obtain the target intermediate C1 (34.81g, 85.3%).

[0169] Structural characterization: MS:531.13 / 532.95.

[0170] Preparation Example 5: Synthesis of Intermediate C2

[0171]

[0172] The raw material 4-tert-butyl-2,6-dibromochlorobenzene (25 g, 76.58 mmol) and intermediate B1 (48.42 g, 168.48 mmol) were added to a 1L single-necked flask, and the catalyst 1,1'-bis(diphenylphosphinoferrocene)palladium dichloride Pd(dppf)Cl 2 (3.06mmol, 2.22g), sodium tert-butoxide (191.45mmol, 18.40g), add 300mL of toluene, react at 100℃ under nitrogen protection for 10h, stop heating, wash with water, concentrate, and purify by reduced pressure distillation to obtain the target intermediate C2 (41.22g, 72.8%).

[0173] Structural characterization: MS:738.37 / 739.44.

[0174] Preparation Example 6: Synthesis of Intermediate C3

[0175]

[0176] Referring to the synthesis method of intermediate C1, intermediate C3 (27.62 g, 84.4%) was synthesized.

[0177] Structural characterization: MS:532.13 / 533.94.

[0178] Preparation Example 7: Synthesis of Intermediate C4

[0179]

[0180] Referring to the synthesis method of intermediate C2, intermediate C4 (47.39 g, 83.5%) was synthesized.

[0181] Structural characterization: MS:740.36 / 741.42.

[0182] Preparation Example 8: Synthesis of Intermediate D1

[0183]

[0184] The intermediate C1 (40 g, 75.05 mmol), Boc anhydride (20 g, 90.06 mmol), and 4-dimethylaminopyridine (4.6 g, 37.53 mmol) were added to a 1 L single-necked flask, and 300 mL of THF was added. The mixture was heated at 60°C for 3 h, and then the heating was stopped. The reaction system was concentrated and purified by column chromatography to synthesize the intermediate D1 (39.65 g, 83.5%).

[0185] Structural characterization: MS:631.19 / 633.07.

[0186] Preparation Example 9: Synthesis of Intermediate D2

[0187]

[0188] Referring to the synthesis method of intermediate D1, intermediate D2 (35.52 g, 74.8%) was synthesized.

[0189] Structural characterization: MS:632.18 / 634.06.

[0190] Preparation Example 10: Synthesis of Intermediate D3

[0191]

[0192] Referring to the synthesis method of intermediate D1, intermediate D3 (30.86 g, 67.9%) was synthesized.

[0193] Structural characterization: MS:838.43 / 839.56.

[0194] Preparation Example 11: Synthesis of Intermediate D4

[0195]

[0196] Referring to the synthesis method of intermediate D1, intermediate D4 (27.66 g, 60.92%) was synthesized.

[0197] Structural characterization: MS:840.42 / 841.54.

[0198] Preparation Example 12: Synthesis of Intermediate D5

[0199]

[0200] Intermediate D3 (30 g, 35.73 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (11.46 g, 42.88 mmol), Pd 2 (dba) 3(1.64 g, 1.79 mmol), tri-tert-butylphosphine tetrafluoroborate (2.20 g, 5.30 mmol), sodium tert-butoxide (5.15 g, 53.60 mmol) were added into a 1 L single-necked flask, and 300 mL of toluene was added. The mixture was reacted at 100 ° C under nitrogen protection for 3 h, and then the heating was stopped. After post-treatment, column chromatography was performed for purification to obtain 30.16 g of the target compound with a yield of 82.3%.

[0201] Structural characterization: MS:1024.57 / 1025.86.

[0202] Preparation Example 13: Synthesis of Intermediate D6

[0203]

[0204] Referring to the synthesis method of intermediate D5, intermediate D6 (28.98 g, 79.1%) was synthesized.

[0205] Structural characterization: MS:1026.56 / 1027.84.

[0206] Preparation Example 14: Synthesis of Intermediate E1

[0207]

[0208] Intermediate D1 (30 g, 47.39 mmol), diphenylamine (9.62 g, 56.87 mmol), Pd 2 (dba) 3 (2.17 g, 2.37 mmol), tri-tert-butylphosphine tetrafluoroborate (2.06 g, 7.11 mmol), sodium tert-butoxide (6.83 g, 71.08 mmol) were added into a 1 L single-necked flask, and 300 mL of toluene was added. The mixture was reacted at 100 ° C under nitrogen protection for 2 hours. The intermediate D1 was completely reacted. The washed liquid was dried and concentrated, and purified by column chromatography to obtain 27.44 g of the target intermediate E1. The yield was 80.25%.

[0209] Structural characterization: MS:720.35 / 721.38.

[0210] Preparation Example 15: Synthesis of Intermediate E2

[0211]

[0212] Referring to the synthetic method of synthetic intermediate E1, intermediate E2 (25.63 g, 75.2%) was synthesized.

[0213] Structural characterization: MS:718.33 / 719.37.

[0214] Preparation Example 16: Synthesis of Intermediate E3

[0215]

[0216] Referring to the synthetic method of synthetic intermediate E1, intermediate E3 (31.16 g, 79.8%) was synthesized.

[0217] Structural characterization: MS:832.47 / 833.60.

[0218] Preparation Example 17: Synthesis of Intermediate E4

[0219]

[0220] Referring to the synthetic method of synthetic intermediate E1, intermediate E4 (34.98 g, 85.9%) was synthesized.

[0221] Structural characterization: MS:1002.56 / 1003.86.

[0222] Preparation Example 18: Synthesis of Intermediate E5

[0223]

[0224] Referring to the synthetic method of synthetic intermediate E1, intermediate E5 (29.68 g, 72.9%) was synthesized.

[0225] Structural characterization: MS:1004.55 / 1005.83.

[0226] Preparation Example 19: Synthesis of Intermediate E6

[0227]

[0228] Referring to the synthetic method of synthetic intermediate E1, intermediate E6 (24.17 g, 70.2%) was synthesized.

[0229] Structural characterization: MS:833.47 / 834.59.

[0230] Preparation Example 20: Synthesis of Intermediate E7

[0231]

[0232] The intermediate D5 (30 g, 29.24 mmol) was added into a 1 L single-necked flask, and 300 mL of THF and 20 mL of concentrated hydrochloric acid were added. The mixture was reacted at 60 ° C for 5 h. Samples were taken for TLC test. The raw material reaction was complete. 200 mL of dichloromethane and 200 mL of water were added. The separated liquid was washed with water, dried and concentrated. The organic phase was evaporated to dryness and slurried with methanol. It was then filtered and dried to obtain the target intermediate E7, 24.33 g, with a yield of 89.9%.

[0233] Structural characterization: MS:924.51 / 925.74.

[0234] Preparation Example 21: Synthesis of Intermediate E8

[0235]

[0236] Referring to the synthesis method of intermediate E7, intermediate E8 (22.76 g, 84.0%) was synthesized. Structural characterization: MS: 926.51 / 927.72.

[0237] Preparation Example 22: Synthesis of Intermediate E9

[0238]

[0239] Referring to the synthesis method of the synthetic intermediate E7, the synthetic intermediate E9 (20.56 g, 79.6%) was synthesized. Structural characterization: MS: 620.30 / 621.27.

[0240] Preparation Example 23: Synthesis of Intermediate E10

[0241]

[0242] Referring to the synthesis method of the synthetic intermediate E7, the intermediate E10 (21.17 g, 80.2%) was synthesized. Structural characterization: MS: 732.42 / 733.48.

[0243] Preparation Example 24: Synthesis of Intermediate E11

[0244]

[0245] Referring to the synthesis method of the synthetic intermediate E7, the intermediate E11 (19.82 g, 75.1%) was synthesized. Structural characterization: MS: 733.42 / 734.47.

[0246] Preparation Example 25: Synthesis of Intermediate E12

[0247]

[0248] Referring to the synthetic method of synthetic intermediate E7, intermediate E12 (22.24 g, 86.1%) was synthesized.

[0249] Structural characterization: MS:618.28 / 619.25.

[0250] Preparation Example 26: Synthesis of Intermediate E13

[0251]

[0252] Referring to the synthetic method of synthetic intermediate E7, intermediate E13 (20.03 g, 77.5%) was synthesized.

[0253] Structural characterization: MS:619.28 / 620.24.

[0254] Preparation Example 27: Synthesis of Intermediate F1

[0255]

[0256] Intermediate E1 (25 g, 40.18 mmol), 3-bromo-6,6,7,7-tetrahydro-5,5,8,8-tetramethylnaphtho[2,3-b]thiophene (15.6 g, 48.21 mmol), Pd 2 (dba) 3 (1.84 g, 2.01 mmol), tri-tert-butylphosphine tetrafluoroborate (1.75 g, 6.03 mmol), sodium tert-butoxide (5.8 g, 60.26 mmol) were added into a 1 L single-necked flask, and 300 mL of toluene was added. The mixture was reacted at 100 ° C under nitrogen protection for 2 hours. The intermediate E1 was reacted completely. The washed liquid was dried and concentrated, and purified by column chromatography to obtain intermediate F1 (26.54 g, 76.4%).

[0257] Structural characterization: MS:863.40 / 864.63.

[0258] Preparation Example 28: Synthesis of Intermediate F2

[0259]

[0260] Referring to the synthesis method of intermediate F1, intermediate F2 (25.96 g, 72.2%) was synthesized.

[0261] Structural characterization: MS:975.53 / 976.85.

[0262] Preparation Example 29: Synthesis of Intermediate F3

[0263]

[0264] Referring to the synthesis method of synthetic intermediate F1, intermediate F3 (27.88 g, 88.7%) was synthesized. Structural characterization: MS: 920.49 / 921.77.

[0265] Preparation Example 30: Synthesis of Intermediate F4

[0266]

[0267] Referring to the synthesis method of synthetic intermediate F1, intermediate F4 (23.74 g, 75.6%) was synthesized. Structural characterization: MS: 921.48 / 922.76.

[0268] Preparation Example 31: Synthesis of Intermediate F5

[0269]

[0270] Referring to the synthesis method of intermediate F1, intermediate F5 (26.94 g, 77.5%) was synthesized. Structural characterization: MS: 861.39 / 862.62.

[0271] Preparation Example 32: Synthesis of Intermediate F6

[0272]

[0273] Referring to the synthesis method of intermediate F1, intermediate F6 (21.46 g, 61.7%) was synthesized. Structural characterization: MS: 860.39 / 861.63.

[0274] Preparation Example 33: Synthesis of Intermediate F7

[0275]

[0276] Referring to the synthesis method of synthetic intermediate F1, intermediate F7 (26.95 g, 74.8%) was synthesized. Structural characterization: MS: 974.53 / 975.86.

[0277] Preparation Example 34: Synthesis of Intermediate F8

[0278]

[0279] Referring to the synthesis method of synthetic intermediate F1, intermediate F8 (26.55 g, 89.9%) was synthesized. Structural characterization: MS: 864.51 / 865.69.

[0280] Preparation Example 35: Synthesis of Intermediate F9

[0281]

[0282] Referring to the synthesis method of synthetic intermediate F1, intermediate F9 (23.86 g, 78.08%) was synthesized. Structural characterization: MS: 865.51 / 866.68.

[0283] Preparation Example 36: Synthesis of Intermediate F10

[0284]

[0285] Referring to the synthesis method of the synthetic intermediate F1, the synthetic intermediate F10 (29.68 g, 87.4%) was synthesized. Structural characterization: MS: 1002.56 / 1003.86.

[0286] Preparation Example 37: Synthesis of Intermediate F11

[0287]

[0288] Referring to the synthesis method of intermediate F1, intermediate F11 (30.14 g, 88.8%) was synthesized.

[0289] Structural characterization: MS:1004.55 / 1005.83.

[0290] Preparation Example 38: Synthesis of Intermediate F12

[0291]

[0292] Referring to the synthesis method of synthetic intermediate F1, intermediate F12 (30.52, 84.54%) was synthesized.

[0293] Structural characterization: MS:1112.58 / 1114.03.

[0294] Preparation Example 39: Synthesis of Intermediate F13

[0295]

[0296] Referring to the synthetic method of synthetic intermediate F1, intermediate F13 (29.67 g, 78.40) was synthesized.

[0297] Structural characterization: MS:1168.62 / 1170.10.

[0298] Preparation Example 40: Synthesis of Material M-14

[0299]

[0300] The intermediate F1 (20 g, 23.16 mmol) was added to a 1L three-necked flask, and 100 mL of ultra-dry xylene was added. Then, under nitrogen protection at -60°C, tert-butyl lithium (36.2 mL, 1.6 M, 57.89 mmol) was slowly added. The mixture was then restored to room temperature and heated to 60°C for activation for 2 hours. The mixture was then restored to room temperature and cooled to -60°C. Boron tribromide (17.40 g, 69.47 mmol) and diisopropylethylamine (11.97 g, 92.63 mmol) were added successively. The mixture was then restored to room temperature and heated to 100°C for reaction for 3 hours. The reaction was stopped after the reaction was stopped. 200 mL of dichloromethane was added for dilution. The separated liquid was washed with water, dried and concentrated. The mixture was purified by column chromatography to obtain 5.11 g of the target product with a yield of 26.4%.

[0301] Structural characterization: MS:836.43 / 836.99.

[0302] Preparation Example 41: Synthesis of Material M-13

[0303]

[0304] Referring to the synthesis method of synthetic material M-14, synthetic material M-13 (4.30 g, 22.1%) was synthesized. Structural characterization: MS: 834.42 / 834.97.

[0305] Preparation Example 31: Synthesis of Material M-15

[0306]

[0307] Referring to the synthesis method of synthetic material M-14, synthetic material M-15 (3.91 g, 20.1%) was synthesized. Structural characterization: MS: 835.41 / 835.96.

[0308] Preparation Example 42: Synthesis of Material M-29

[0309]

[0310] Referring to the synthesis method of synthetic material M-14, synthetic material M-29 (4.52 g, 23.3%) was synthesized. Structural characterization: MS: 894.51 / 895.11.

[0311] Preparation Example 43: Synthesis of Material M-31

[0312]

[0313] Referring to the synthesis method of synthetic material M-14, synthetic material M-31 (3.87 g, 19.9%) was synthesized. Structural characterization: MS: 895.51 / 896.10.

[0314] Preparation Example 44: Synthesis of Material M-44

[0315]

[0316] Referring to the synthesis method of synthetic material M-14, synthetic material M-44 (4.06 g, 20.8%) was synthesized. Structural characterization: MS: 948.56 / 949.21.

[0317] Preparation Example 45: Synthesis of Material M-46

[0318]

[0319] Referring to the synthesis method of synthetic material M-14, synthetic material M-46 (3.38 g, 17.4%) was synthesized. Structural characterization: MS: 949.55 / 950.19.

[0320] Preparation Example 46: Synthesis of Material M-72

[0321]

[0322] Referring to the synthesis method of synthetic material M-14, synthetic material M-72 (4.35 g, 22.3%) was synthesized. Structural characterization: MS: 1086.61 / 1087.37.

[0323] Preparation Example 47: Synthesis of Material M-97

[0324]

[0325] Referring to the synthesis method of synthetic material M-14, synthetic material M-97 (4.17 g, 21.5%) was synthesized. Structural characterization: MS: 838.54 / 839.03.

[0326] Preparation Example 48: Synthesis of Material M-126

[0327]

[0328] Referring to the synthesis method of synthetic material M-14, synthetic material M-126 (3.81 g, 19.6%) was synthesized. Structural characterization: MS: 839.53 / 840.02.

[0329] Preparation Example 49: Synthesis of Material M-115

[0330]

[0331] Referring to the synthesis method of synthetic material M-14, synthetic material M-115 (4.42 g, 22.7%) was synthesized.

[0332] Structural characterization: MS:976.59 / 977.20.

[0333] Preparation Example 50: Synthesis of Material M-125

[0334]

[0335] Referring to the synthesis method of synthetic material M-14, synthetic material M-125 (3.86 g, 19.8%) was synthesized.

[0336] Structural characterization: MS:978.58 / 979.18.

[0337] Preparation Example 51: Synthesis of Material M-76

[0338]

[0339] Referring to the synthesis method of synthetic material M-14, synthetic material M-76 (4.15 g, 16.98%) was obtained.

[0340] Structural characterization: MS:1142.64 / 1143.44.

[0341] The present invention exemplifies the specific synthesis methods of the above compounds. For other compounds for which no specific synthesis methods are given, they can be prepared by similar methods, and they can be obtained by simply replacing the raw materials. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0342] Device Example 1

[0343] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0344] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0345] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0346] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0347] (4) vacuum evaporating compound HT-14 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0348] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer comprises a binary mixture of a main material BFH-4 and a dye (the organic compound M-1 provided by the present invention), BFH-4:M-1 (100:3, w / w), using a multi-source co-evaporation method, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 20 nm;

[0349] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0350] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0351] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0352] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0353] Device Examples 2 to 16 and Device Comparative Examples 1 to 5 are all organic electroluminescent devices, which differ from Device Example 1 only in that the dyes of the light-emitting layer are the compounds shown in Table 1; other levels, thicknesses, materials and preparation methods are the same as those of Device Example 1.

[0354] The structures of dyes N-1 to N-5 in device comparative examples 1 to 5 are as follows. The synthesis methods are similar to those of the compounds of the present invention and are not described in detail here:

[0355]

[0356] Device performance test:

[0357] (1) using an integrating sphere to measure the external quantum efficiency (EQE, %) of an organic electroluminescent device; setting the test value of the external quantum efficiency of device comparative example 1 to 1.0, and calculating the ratio of the test value of the external quantum efficiency of other devices to the test value of the external quantum efficiency of device comparative example 1;

[0358] (2) Voltage: Under the same brightness, use a digital source meter and a brightness meter to measure the driving voltage of the organic electroluminescent device. Specifically, increase the voltage at a rate of 0.1V per second and measure the voltage when the brightness of the organic electroluminescent device reaches 10000cd / m 2 The voltage at this time is the driving voltage;

[0359] (3) The LT97 life test is as follows: Use a brightness meter at 10mA / cm 2The initial brightness value of the device under the current density, maintaining a constant current, and measuring the time for the device brightness to drop to 97% of the initial brightness, the unit is h; the LT97 life test value of the device comparison example 1 is recorded as 1.0, and the ratio of the LT97 life test value of other devices to the LT97 life test value of the device comparison example 1 is calculated;

[0360] The test results are shown in Table 1:

[0361] Table 1

[0362]

[0363]

[0364] According to the data in Table 1, when the materials and preparation processes of the other functional layers of the organic electroluminescent device are exactly the same, the organic electroluminescent devices provided by the device embodiments 1 to 16 of the present invention can effectively reduce the operating voltage by 0.2-1.0V, the external quantum efficiency EQE can be improved by 15%, and the LT97 life can be improved by 20%, relative to the device comparison examples 1 and 2. This is probably because the BN aromatic ring skeleton is connected to the biphenyl branched structure (the group of formula (b)), which enhances the charge transfer ability while inhibiting the charge accumulation in the material, thereby achieving a voltage drop, an improvement in the external quantum efficiency and an extension of the device life. The compounds of device comparison examples 3 to 5 are very similar to the compounds of device embodiments 1 to 3, but better device performance is achieved by the introduction of L. The mechanism is not clear, and it may be due to the following: when L is not a single bond, the carrier transport and electronic tolerance of the material are further enhanced, which is reflected in the device performance as a reduced operating voltage, an increased EQE, and an extended life.

[0365] The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements. The attached claims summarize the scope of the present invention. The equivalent replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-nitrogen-containing organic compound having a structure shown in formula (I): in, Ring A, Ring B, and Ring C are each independently selected from any one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, Ar 1 ,Ar 2 Each is independently selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; Ar 1 ,Ar 2 At least one of them has a structure of formula (b), and / or at least one of ring A, ring B, and ring C has a substituent of the structure of formula (b), Ring N and ring M each independently represent a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring; L represents a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ra and Rb each independently represent one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, and substituted or unsubstituted C3-C20 cycloalkyl; The above-mentioned substituents are each independently selected from any one of C1~C20 chain alkyl, C1~C20 chain halogenated alkyl, C2~C20 alkenyl, C3~C20 cycloalkyl, C1~C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6~C30 aryl, C3~C30 heteroaryl, or a combination of at least two thereof; the * indicates the connection site.

2. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: Ar 1 ,Ar 2 One of them is a structure of formula (b) or Ar 1 ,Ar 2 All of them are of formula (b); Ra and Rb are one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C3-C10 cycloalkyl. Ra and Rb are preferably one of hydrogen, substituted or unsubstituted C1-C4 chain alkyl, and substituted or unsubstituted C3-C10 cycloalkyl. Preferably, the structure of formula (b) is a structure as shown in formula (b-1): Wherein, L represents one of a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group; X 1 -X 5 and X 1’ -X 5’ Represents CR 0 or N, where R 0 are independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl, The substituents mentioned above are each independently selected from any one or a combination of at least two of C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl or C3-C30 heteroaryl. The expression of a ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond, and the * indicates the connection site.

3. The organic compound according to claim 2, characterized in that In formula (b-1), R 0 are independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl, Preferably, R 0 Each is independently selected from one of hydrogen, C1-C6 chain alkyl, C1-C6 chain halogenated alkyl, C2-C6 alkenyl, C6-C12 aryl, and C3-C12 heteroaryl; More preferably, R 0 Each is independently selected from one of hydrogen, C1-C6 chain alkyl, C2-C6 alkenyl, C6-C12 aryl and C3-C12 heteroaryl.

4. The organic compound according to claim 1, characterized in that L represents a substituted or unsubstituted C6-C12 arylene group, or a substituted or unsubstituted C3-C12 heteroarylene group; Preferably, L is selected from one or a combination of at least two of the following substituted or unsubstituted groups: Y 1 , Y 2 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 , R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, L is selected from one of the following substituted or unsubstituted groups: The substituents mentioned above are each independently selected from any one or a combination of at least two of C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl or C3-C30 heteroaryl. The expression of a ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond, and the * indicates the connection site.

5. The organic compound according to claim 1, characterized in that The ring A and the ring B each independently have a structure as shown in formula (C) or formula (D): The dashed single or double bonds indicate the fusion positions of the groups; Z 1 ~Z 8 Each independently is CR 2 or N; R 2 Each is independently selected from hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, C3-C30 heteroaryl; adjacent R 2 are not connected or connected to form a ring through chemical bonds; the R 2 Not connected to adjacent ring structures or connected to form a ring through chemical bonds; Preferably, R 2 Selected from the following groups: *- *-F *-CN * indicates the connection site; X is selected from O, S, NR 21 or CR 22 R 23 ; R 21 , R 22 , R 23 Each is independently selected from any one of a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, The substituents mentioned above are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group.

6. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in formula (II-1) to formula (II-5): Among them, Z 1 ~Z 8 Each independently has the same definition as claim 5; Z 1’ ~Z 4’ Each independently is CR 2 or N; R 2 Each is independently selected from hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, C3-C30 heteroaryl; adjacent R 2 are not connected or connected to form a ring through chemical bonds; the R 2 Not connected to adjacent ring structures or connected to form a ring through chemical bonds; Z 9 ~Z 17 , Z 9’ ~Z 12’ Independently selected from CR 4 or N, R 4 Each of the following groups is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R 3 is selected from substituted or unsubstituted C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, R 3 Not connected to adjacent ring structures or connected to form a ring through chemical bonds; E represents the following group, Wavy lines indicate junction sites; The substituents mentioned above are each independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group.

7. The boron-nitrogen-containing organic compound according to claim 1, which is the following specific compound, 8. Use of the organic compound according to any one of claims 1 to 7 in an organic electronic device; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the application is application as a light-emitting layer material in an organic electroluminescent device.

9. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, characterized in that: The organic layer contains the organic compound according to any one of claims 1 to 7; Preferably, at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 7. Preferably, the light-emitting layer comprises a host material and a dye, and the dye comprises at least one organic compound according to any one of claims 1 to 7.

10. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 9.

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