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 containing the organic compound, particularly relates to a boron-nitrogen-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in the organic electroluminescent device. The organic compound has the structure shown in the formula (1), stability and steric configuration are good, high luminous efficiency can be achieved through molecular axial extension, excellent carrier transport efficiency is achieved, the organic compound serves as a material of a luminous layer to be used for an organic electroluminescent device, the service life of the device can be effectively prolonged, and the luminous efficiency is improved. # 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] OLED (Organic Light-Emitting Diode) refers to an organic semiconductor that is made of an extremely thin organic material coating and a glass substrate and emits light when current passes through it. As a new generation of display technology, OLED has better display performance than LCD, with the advantages of self-luminescence, good display effect, low power consumption, high flexibility and ultra-thinness. It is widely used in the screens of smart phones, automotive electronics, smart wearable devices, VR devices and other products.

[0003] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. In 2016, Professor Takuji Hatakeyama of Japan proposed a TADF (Thermally Activated Delayed Fluorescence) material design strategy based on BN resonance (Adv. Mater. 2016, 28, 2777-2781). At present, BN resonance blue light dyes are mainly used in the TTA system of the production line. They have the advantages of narrow luminescence half-peak width and high color purity. This type of material is composed of boron atoms, nitrogen atoms and multiple benzene rings, showing a rigid polycyclic aromatic hydrocarbon structure. However, due to its particularly planar rigid structure, it is easy to cause molecular stacking and exciton annihilation, resulting in serious efficiency roll-off. Therefore, this type of organic electroluminescent material still has a lot of room for improvement in terms of luminescence performance, and the industry urgently needs to develop new luminescent material systems to meet commercial needs. 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; some solutions are to use dimethylfluorene structure to suppress intramolecular rotational energy levels, but at the same time, it will produce charge transfer imbalance, resulting in poor device life.

[0004] Therefore, the existing organic electroluminescent materials still have a lot of room for improvement in terms of luminescent performance, and the industry urgently needs to develop new luminescent material systems to meet commercial needs. The researchers of the present invention have discovered an ingenious molecular design scheme through careful thinking and continuous experiments, which is described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLEDs and improve device life. 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 present invention provides a boron-nitrogen-containing organic compound. In the structure of this series of compounds, peripheral substituent structures such as tert-butylphenyl are introduced outwardly on both sides of the mother core, which is beneficial to improving the efficiency of the device.

[0006] More specifically, the present invention provides a boron-nitrogen-containing organic compound having a structure shown in formula (1):

[0007] It has the structure shown in formula (1):

[0008]

[0009] In formula (1), ring A, ring B, and ring C are each independently a C6-C50 aromatic ring or a C3-C50 heteroaromatic ring;

[0010] R 4 , R 5 are each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 4 , R 5 They are independently connected to each other by chemical bonds to form a ring or are not connected;

[0011] R 2 are each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, the two R c They are connected to each other by chemical bonds to form a ring or not;

[0012] Ar is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; L, L' are each independently selected from a single bond, a C1-C20 straight or branched alkylene group, a substituted or unsubstituted C2-C10 alkenylene group, a substituted or unsubstituted C3-C20 cycloalkylene group;

[0013] R 1, R 1’ is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; said R 1 , R 1’ The aromatic ring or heteroaromatic ring is not connected to the connected aromatic ring or is connected to each other by chemical bonds to form a ring;

[0014] b is an integer selected from 0 to 3; d and e are each independently selected from 0 to the maximum substitutable integer;

[0015] M is a group represented by the structure of formula (1-a), c is an integer selected from 0 to 4, R 3 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; said R 3 The aromatic ring or heteroaromatic ring is not connected to the connected aromatic ring or is connected to each other by chemical bonds to form a ring;

[0016] The above-mentioned substituents are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, unsubstituted or substituted C1-C20 straight or branched alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C1-C20 alkoxy, unsubstituted or substituted C1-C20 alkylsilyl, unsubstituted or substituted C1-C20 alkylamino, unsubstituted or substituted C6-C30 arylamino, unsubstituted or substituted C3-C30 heteroarylamino, unsubstituted or substituted C6-C30 aryloxy, unsubstituted or substituted C3-C30 heteroaryloxy, unsubstituted or substituted C6-C60 aryl, and unsubstituted or substituted C3-C60 heteroaryl. The expression of the ring structure crossed out by “—” indicates that the connection site is at any bonding position on the ring structure, and the * indicates the connection site.

[0017] The boron-nitrogen organic compound provided by the present invention has a specific molecular structure shown in formula (1). By adopting the thiophene aromatic amine phenyl meta-position connecting steric hindering groups to inhibit molecular vibration and rotation, the molecular vibration and rotation energy is weakened and the radiation energy loss is reduced. At the same time, the extension of the benzene ring increases the molecular horizontal dipole orientation and improves the light extraction efficiency. N-ortho-substituted 3,5-di-tert-butylbenzene can enhance the dissociation energy of the molecule and improve the stability of the molecule.

[0018] Of course, the parent core structure is also very important. The boron-nitrogen-containing organic compound has good stability and spatial configuration, can utilize triplet excitons to achieve higher luminescence efficiency, has excellent carrier transport properties, and effectively avoids molecular aggregation, which improves the stability and efficiency of the device.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0024] 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.

[0025] 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.

[0026] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0027] 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.

[0028] 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.

[0029] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0030] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0031] 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.

[0032] The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

[0033] 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.

[0034] The above-mentioned C6-C60 aromatic ring (or C6-C50 aromatic ring) and C3-C60 heteroaromatic ring (or C6-C50 heteroaromatic ring) in the present invention, unless otherwise specified, are aromatic groups that satisfy the π conjugated system, including 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.

[0035] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring (or C6-C50 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.

[0036] In the present specification, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 aryl group) is preferably a C6-C30 aryl 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 (or C6-C50 aryl group) of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[0037] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring (or C3-C50 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, yl, 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, benzopyridazine 1,5-diazaanthenyl, 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 , 1,2,4-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, indolizinyl, 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.

[0038] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group (or C3-C50 heteroaryl group) is preferably a C3-C30 heteroaryl group, and more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, quinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalin imidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzo pyridazinyl, 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, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, 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.

[0039] In the present invention, the aryloxy group and heteroaryloxy group include groups formed by the above-mentioned aryl group and heteroaryl group and oxygen. In the present invention, the arylamino group and heteroarylamino group include groups formed by replacing one or two H in the -NH2 group with the above-mentioned aryl group and heteroaryl group.

[0040] In the present specification, examples of C1-C20 straight-chain or branched 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.

[0041] 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, cycloheptyl, cyclooctyl, adamantyl and the like.

[0042] 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.

[0043] 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.

[0044] In the present specification, the alkoxy group refers to a group consisting of the above-mentioned straight-chain or branched alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0045] 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.

[0046] In the present specification, examples of C1-C20 alkylsilyl 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 straight or branched alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0047] In a preferred embodiment of the present invention, the ring C has a structure as shown in formula (f):

[0048]

[0049] Among them, the dotted lines represent the fused bonds of the groups;

[0050] Z 1 , Z 2 , Z 3 Each independently is CR 31 or N;

[0051] R 31 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 31 Not connected to adjacent ring structures or connected to form a ring through chemical bonds;

[0052] The substituents of the above substitutions are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0053] Preferably, the Z 1 , Z 2 , Z 3 At most one of them is N; further preferably, the Z 1 , Z 2 , Z 3 Each independently is CR 31 ;

[0054] More preferably, Z 1 , Z 3 for CH, the Z 2 CR 31 , the R 31 It is one or a combination of two of hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, cyclopentyl, cyclohexyl and adamantyl.

[0055] In a preferred embodiment of the present invention, ring A or ring B is a structure represented by formula A-1 or A-2:

[0056]

[0057] Indicates the fusion position, Y is O, S, NR 21 , CR 21 R 22 One of the 21 , R 22 Each is independently selected from any one of hydrogen, C1-C20 straight chain or branched chain alkyl;

[0058] X 1 -X 4 Each is independently denoted as CR 11 or N; R 11 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, condensed ring aryl, substituted or unsubstituted C3-C30 heteroaryl; each R 11 Same or different, adjacent R 11 The bases are not connected or connected to form a ring through chemical bonds.

[0059] Preferably, Y is S; the adjacent R 11 The base is not connected.

[0060] The substituents mentioned above are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0061] In a preferred embodiment of the present invention, the compound represented by formula (1) is a compound represented by formula 1-1 to formula 1-5,

[0062]

[0063]

[0064] R 1 , R 1 '、R 2 , R 4 , R 5 , b, d, e, Ar, and M have the same meanings as in formula (1); L and L' are each independently a single bond, methylene, ethylene, propylene, isopropylidene, or ethylidene;

[0065] R 1 , L and Ar are connected to form a ring or not, R 1 ', L' and Ar are connected to form a ring or not,

[0066] Preferably R 1 , R 1 ' are each independently selected from a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R 1 , R 1 'Not connected to adjacent groups or connected to form a ring through chemical bonds;

[0067] More preferably, R 1 , R 1 ' are independently selected from C1-C10 chain alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl; more preferably R 1 , R 1 ' are each independently selected from one or a combination of two of methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, isopropylphenyl, pyridyl, furyl, and thienyl,

[0068] The substituents mentioned above are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0069] In a preferred embodiment of the present invention, the M group is one selected from the following groups,

[0070]

[0071]

[0072] In a preferred embodiment of the present invention, Ar is substituted or unsubstituted and is selected from the following groups:

[0073]

[0074] The substitution in the above-mentioned "substituted or unsubstituted" refers to substitution by at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, isobutyl, dimethylpropyl, cyclohexane and adamantane.

[0075] Furthermore, the organic compound of the present invention can preferably include the specific structural compounds shown below, which are only representative and do not limit the scope of the present invention:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] The preparation process of the boron-nitrogen-containing organic compound is simple and easy, the raw materials are easily available, and it is suitable for mass production and expansion. It is used as a material for the light-emitting layer in an organic electroluminescent device, so that the device can achieve high-quality light-emitting effects, effectively extend the life of the device, and improve the light-emitting efficiency.

[0083] 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.

[0084] 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.

[0085] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0086] Preferably, the organic compound is used as a luminescent dye of a light-emitting layer in an organic electroluminescent device.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0094] The OLED device prepared by using the compound of the present invention has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials. DETAILED DESCRIPTION

[0095] The technical solution of the present invention is further described in more detail below.

[0096] Synthesis methods of compounds

[0097] The specific synthesis examples of the boron-nitrogen-containing organic compounds can be synthesized by the methods described in Synthesis Examples 1 to 8 described later, and the desired compounds can be obtained by replacing the corresponding raw materials and appropriately converting the functional groups. It should be noted that obtaining the boron-nitrogen-containing organic compounds is not limited to the synthesis methods and raw materials used in the present invention, and those skilled in the art can also choose other methods or routes to obtain the boron-nitrogen-containing organic compounds proposed in the present invention. The compounds for which the synthesis methods are not mentioned in the present invention are all raw material products obtained through commercial channels, or are made by themselves according to known methods using these raw material products.

[0098] The following synthesis examples of the present invention illustratively provide specific synthesis methods for representative compounds. The solvents and reagents, intermediates, ethyl acetate, methanol, ethanol and other chemical reagents used in the following synthesis examples can all be purchased or customized from the domestic chemical product market.

[0099] 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.

[0100] 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.

[0101] Organic EL devices

[0102] The OLED structure of the present invention can refer to the known technology. For example, the organic electroluminescent device OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region. The compound of the present invention can be contained in the organic material layer, and is particularly suitable for being contained in the light emitting layer.

[0103] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0104] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy 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 any combination thereof can be used.

[0105] 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.

[0106] 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.

[0107] 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 vinylene, polyaniline / dodecylbenzene sulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate)

[0108] (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.

[0109]

[0110]

[0111]

[0112]

[0113] 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.

[0114]

[0115] 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.

[0116] 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.

[0117] 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.

[0118]

[0119] The OLED organic material 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 multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0120] 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.

[0121]

[0122]

[0123]

[0124]

[0125] 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, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0126] 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.

[0127] Example

[0128] Synthesis of compounds

[0129] 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 raw materials and intermediates used in the present invention are all obtained through commercial channels. The solvents and reagents used in the present invention, such as chemical reagents such as dichloromethane, petroleum ether, ethanol, tert-butylbenzene, boron tribromide, diphenylamine, etc., can be purchased from the domestic chemical product market, such as purchased 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 raw materials in the present invention uses a gas chromatography-mass spectrometer (GC-MS, Shimadzu QP2010 SE).

[0130] Synthesis Example 1: Synthesis of S1

[0131]

[0132] Synthesis of intermediate M1-1:

[0133] At room temperature, raw material 1 (80 g, 283.69 mmol), raw material 2 (146.59 g, 312.05 mmol), Pd2dba3 (6.46 g, 5.67 mmol), tri-tert-butylphosphine tetrafluoroborate (3.29 g, 11.35 mmol), sodium tert-butoxide (40.9 g, 425.53 mmol), toluene (500 ml) as solvent were added to a 1000 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography on a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 130 g of white solid M2-1, with a yield of 68.31%. The molecular ion mass determined by mass spectrometry was 669.41 (theoretical value: 669.39).

[0134] Synthesis of intermediate M1-2:

[0135] At room temperature, M1-1 (15 g, 22.36 mmol), raw material 3 (11.55 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 10 g of white solid M1-2, with a yield of 40.51%. The molecular ion mass determined by mass spectrometry was: 1102.71 (theoretical value: 1102.69).

[0136] Synthesis of final product S1:

[0137] At room temperature, add M1-2 (10 g, 9.06 mmol) and xylene (40 ml) to a 250 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (11.32 ml, 18.11 mmol, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (1.75 ml, 18.11 mmol, 2.60 g / ml) to the system at -40 ° C, stir at room temperature for 1 h, the system changes from white turbid to red solution. Then add N, N-diisopropylethylamine (4.75 ml, 27.17 mmol, 0.74 g / ml) at -40 ° C, heat to 120 ° C and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE:DCM=20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.1 g of the sample before sublimation, with a yield of 21.52%. The molecular ion mass determined by mass spectrometry was 1076.74 (theoretical value: 1076.72).

[0138] Synthesis Example 2: Synthesis of S2

[0139]

[0140] Synthesis of intermediate M2-1:

[0141] At room temperature, M1-1 (15 g, 22.36 mmol), raw material 4 (12.78 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 11.3 g of white solid M2-1, with a yield of 43.79%. The molecular ion mass determined by mass spectrometry was: 1152.73 (theoretical value: 1152.71).

[0142] Synthesis of final product S2:

[0143] At room temperature, add M2-1 (11 g, 9.53 mmol) and xylene (40 ml) to a 250 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (11.91 ml, 19.06 mmol, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (1.84 ml, 19.06 mmol, 2.60 g / ml) to the system at -40 ° C, stir at room temperature for 1 h, the system changes from white turbid to red solution. Then add N, N-diisopropylethylamine (4.99 ml, 28.59 mmol, 0.74 g / ml) at -40 ° C, heat to 120 ° C and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.3 g of the sample before sublimation, with a yield of 21.40%. The molecular ion mass determined by mass spectrometry was 1126.74 (theoretical value: 1126.73).

[0144] Synthesis Example 3: Synthesis of S5

[0145]

[0146] Synthesis of intermediate M3-1:

[0147] At room temperature, M1-1 (15 g, 22.36 mmol), raw material 5 (13.77 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 12.1 g of white solid M3-1, with a yield of 45.31%. The molecular ion mass determined by mass spectrometry was: 1192.71 (theoretical value: 1192.70).

[0148] Synthesis of final product S5:

[0149] At room temperature, add M3-1 (12g, 10.05mmol) and xylene (40ml) to a 250ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (12.56ml, 20.10mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to deep red. Add boron tribromide (1.94ml, 20.10mmol, 2.60g / ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (5.27ml, 30.15mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE: DCM = 20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.2 g of the pre-sublimation sample, with a yield of 18.75%. The molecular ion mass determined by mass spectrometry was 1166.74 (theoretical value: 1166.73).

[0150] Synthesis Example 4: Synthesis of S12

[0151]

[0152] Synthesis of intermediate M4-1:

[0153] At room temperature, M1-1 (15 g, 22.36 mmol), raw material 6 (12.04 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography on a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 13.1 g of white solid M4-1, with a yield of 52.12%. The molecular ion mass determined by mass spectrometry was 1122.61 (theoretical value: 1122.59).

[0154] Synthesis of final product S12:

[0155] At room temperature, add M4-1 (13g, 11.57mmol) and xylene (40ml) to a 250ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (14.46ml, 23.13mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.23ml, 23.13mmol, 2.60g / ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (6.06ml, 34.70mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE: DCM = 20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.5 g of the sample before sublimation, with a yield of 19.70%. The molecular ion mass determined by mass spectrometry was 1096.62 (theoretical value: 1096.61).

[0156] Synthesis Example 5: Synthesis of S20

[0157]

[0158] Synthesis of intermediate M5-1:

[0159] At room temperature, raw material 1 (80 g, 283.69 mmol), raw material 3 (159.91 g, 340.42 mmol), Pd2dba3 (6.46 g, 5.67 mmol), tri-tert-butylphosphine tetrafluoroborate (3.29 g, 11.35 mmol), sodium tert-butoxide (40.9 g, 425.53 mmol), toluene (500 ml) as solvent were added to a 1000 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography on a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 132.3 g of white solid M5-1, with a yield of 69.52%. The molecular ion mass determined by mass spectrometry was 669.31 (theoretical value: 669.30).

[0160] Synthesis of intermediate M5-2:

[0161] At room temperature, M5-1 (15 g, 22.36 mmol), raw material 7 (12.88 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography on a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 12.3 g of white solid M5-2, with a yield of 47.49%. The molecular ion mass determined by mass spectrometry was: 1156.75 (theoretical value: 1156.74).

[0162] Synthesis of final product S20:

[0163] At room temperature, add M5-2 (12.3 g, 10.62 mmol) and xylene (40 ml) to a 250 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (13.27 ml, 21.24 mmol, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.05 ml, 21.24 mmol, 2.60 g / ml) to the system at -40 ° C, stir at room temperature for 1 h, the system changes from white turbid to red solution. Then add N, N-diisopropylethylamine (5.56 ml, 31.86 mmol, 0.74 g / ml) at -40 ° C, heat to 120 ° C and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added and mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.3 g of the sample before sublimation, with a yield of 19.14%. The molecular ion mass determined by mass spectrometry was 1130.77 (theoretical value: 1130.76).

[0164] Synthesis Example 6: Synthesis of S22

[0165]

[0166] Synthesis of intermediate M6-1:

[0167] At room temperature, M5-1 (15 g, 22.36 mmol), raw material 8 (12.05 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 13.2 g of white solid M6-1, with a yield of 52.51%. The molecular ion mass determined by mass spectrometry was: 1122.67 (theoretical value: 1122.66).

[0168] Synthesis of final product S22:

[0169] At room temperature, add M6-1 (13g, 11.56mmol) and xylene (40ml) to a 250ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (14.46ml, 23.13mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to deep red. Add boron tribromide (2.23ml, 23.13mmol, 2.60g / ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (6.06ml, 34.69mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE: DCM = 20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.35 g of the pre-sublimation sample, with a yield of 18.52%. The molecular ion mass determined by mass spectrometry was 1096.69 (theoretical value: 1096.68).

[0170] Synthesis Example 7: Synthesis of S27

[0171]

[0172] Synthesis of intermediate M7-1:

[0173] At room temperature, M5-1 (15 g, 22.36 mmol), raw material 9 (12.39 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography on a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 12.8 g of white solid M7-1, with a yield of 50.30%. The molecular ion mass determined by mass spectrometry was: 1136.65 (theoretical value: 1136.64).

[0174] Synthesis of final product S27:

[0175] At room temperature, add M7-1 (12.8 g, 11.25 mmol) and xylene (40 ml) to a 250 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (14.06 ml, 22.49 mmol, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.17 ml, 22.49 mmol, 2.60 g / ml) to the system at -40 ° C, stir at room temperature for 1 h, the system changes from white turbid to red solution. Then add N, N-diisopropylethylamine (5.89 ml, 33.74 mmol, 0.74 g / ml) at -40 ° C, heat to 120 ° C and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE:DCM=20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.41 g of the pre-sublimation sample, with a yield of 19.28%. The molecular ion mass determined by mass spectrometry was 1110.67 (theoretical value: 1110.66).

[0176] Synthesis Example 8: Synthesis of S36

[0177]

[0178] Synthesis of intermediate M8-1:

[0179] At room temperature, M5-1 (15 g, 22.36 mmol), raw material 10 (14.24 g, 24.60 mmol), Pd132 (0.32 g, 0.45 mmol), sodium tert-butoxide (4.30 g, 44.72 mmol), toluene (100 ml) as solvent were added to a 250 ml single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C for 4 hours. After the reaction solution was cooled, it was subjected to rapid column chromatography in a silica gel column filled with silica gel, with dichloromethane as the eluent, concentrated, and washed with ethanol to obtain 13.3 g of white solid M8-1, with a yield of 49.03%. The molecular ion mass determined by mass spectrometry was: 1211.70 (theoretical value: 1211.69).

[0180] Synthesis of final product S36:

[0181] At room temperature, add M8-1 (13g, 10.72mmol) and xylene (40ml) to a 250ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (13.39ml, 21.43mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.06ml, 21.43mmol, 2.60g / ml) to the system at -40℃, stir at room temperature for 1h, the system changes from white turbid to red solution. Then add N,N-diisopropylethylamine (5.61ml, 32.15mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (100 ml) was added, and the mixture was concentrated by silica gel, and then column chromatography (PE:DCM=20:1) was performed. The crude product was recrystallized twice from toluene / ethanol to obtain 2.45 g of the pre-sublimation sample, with a yield of 19.27%. The molecular ion mass determined by mass spectrometry was 1185.72 (theoretical value: 1185.71).

[0183] Device Example 1

[0184] The following organic electroluminescent device was prepared, and the device structure is shown below:

[0185] ITO(150nm) / HI-2(10nm) / HT-2(40nm) / HT14(5nm) / BFH-3:S1(30nm, 5%wt) / ET-59(25nm) / LiF(0.5nm) / Al(150nm).

[0186] The organic electroluminescent device was prepared as follows: a glass plate coated with a transparent conductive layer of ITO (thickness 150 nm) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, 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;

[0187] The glass substrate with the anode is placed in a vacuum chamber, and the vacuum is evacuated to 1×10-5~1×10-4Pa. HI-2 and HT-2 are vacuum-deposited on the anode layer as a hole injection layer and a hole transport layer, respectively, and HT14 is used as an electron blocking layer. The evaporation rate is 0.1nm / s, and the evaporation film thicknesses are 10nm, 40nm and 5nm, respectively.

[0188] "BFH-3: S1 (30nm, 5%wt)" is vacuum evaporated on the hole transport layer as the light-emitting layer of the organic electroluminescent device. The evaporation rate is 0.1nm / s and the total film thickness of the evaporation is 30nm; "5%wt" refers to the doping ratio of the blue light dye, that is, the weight ratio of the main material to S2 is 95:5.

[0189] ET-59 was vacuum-deposited on the light-emitting layer as the electron transport layer of the organic electroluminescent device, with a deposition rate of 0.1 nm / s and a total deposition film thickness of 20 nm;

[0190] 0.5 nm of LiF as an electron injection layer and 150 nm of Al as a cathode were vacuum-deposited on the electron transport layer.

[0191] Device Examples 2-9, Device Comparative Examples 1-3

[0192] The manufacturing process of these examples is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced with R-1, R-2, and R-3.

[0193]

[0194] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0195] At the same brightness, a digital source meter and a brightness meter are used to measure the driving voltage and current efficiency of the organic electroluminescent devices prepared in Examples 1-9 and Comparative Examples 1-3, as well as the life of the devices. Specifically, the voltage is increased at a rate of 0.1V per second, and the voltage when the brightness of the organic electroluminescent device reaches 1000cd / m2, i.e., the driving voltage, is measured, and the current density at this time is measured; the external quantum efficiency is measured using an integrating sphere; the LT95 life test is as follows: a brightness meter is used to maintain a constant current at a brightness of 1000cd / m2, and the time it takes for the brightness of the organic electroluminescent device to drop to 950cd / m2 is measured, and the LT95 life test value of Comparative Example 1 is recorded as 1, and the LT95 life of each device embodiment and other comparative examples is the ratio of their respective LT95 life test values ​​to the test value of Comparative Example 1 (relative life). The results are shown in the following table:

[0196]

[0197] As can be seen from Table 1 above, compared with devices prepared using prior art compounds R-1, R-2, and R-3, organic electroluminescent devices prepared using the compounds of the present invention as luminescent dyes have higher luminous efficiency and longer life. The compounds of the present invention use thiophene aromatic amine phenyl meta-positions to connect steric groups to inhibit molecular vibration and rotation, weaken the molecular vibration and rotation energy, and reduce radiation energy loss. At the same time, extending the benzene ring increases the molecular horizontal dipole orientation and improves the light extraction efficiency. N-ortho-substituted 3,5-di-tert-butylbenzene can enhance the dissociation energy of the molecule and improve the stability of the molecule. In summary, the organic electroluminescent device using the compounds of the present invention significantly improves the device external quantum efficiency, reduces the device operating voltage, and increases the working life.

[0198] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

[0199] 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 (1): In formula (1), ring A, ring B, and ring C are each independently a C6-C50 aromatic ring or a C3-C50 heteroaromatic ring; R 4 , R 5 are each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 4 , R 5 They are independently connected to each other by chemical bonds to form a ring or are not connected; R 2 are each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, the two R 2 They are connected to each other by chemical bonds to form a ring or not; Ar is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; L, L ’ Each is independently selected from a single bond, a C1-C20 straight or branched alkylene group, a substituted or unsubstituted C2-C10 alkenylene group, and a substituted or unsubstituted C3-C20 cycloalkylene group; R 1 , R 1’ is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; said R 1 , R 1’ The aromatic ring or heteroaromatic ring is not connected to the connected aromatic ring or is connected to each other by chemical bonds to form a ring; b is an integer selected from 0 to 3; d and e are each independently selected from 0 to the maximum substitutable integer; M is a group represented by the structure of formula (1-a), c is an integer selected from 0 to 4, R 3 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; said R 3 The aromatic ring or heteroaromatic ring is not connected to the connected aromatic ring or is connected to each other by chemical bonds to form a ring; The above-mentioned substituents are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, unsubstituted or substituted C1-C20 straight or branched alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C1-C20 alkoxy, unsubstituted or substituted C1-C20 alkylsilyl, unsubstituted or substituted C1-C20 alkylamino, unsubstituted or substituted C6-C30 arylamino, unsubstituted or substituted C3-C30 heteroarylamino, unsubstituted or substituted C6-C30 aryloxy, unsubstituted or substituted C3-C30 heteroaryloxy, unsubstituted or substituted C6-C60 aryl, and unsubstituted or substituted C3-C60 heteroaryl. The expression of the ring structure crossed by "—" indicates that the connection site is at any bonding position on the ring structure, and the * indicates the connection site.

2. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: The ring C has a structure as shown in formula (f): Among them, the dotted lines represent the fused bonds of the groups; Z 1 , Z 2 , Z 3 Each independently is CR 31 or N; R 31 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 31 Not connected to adjacent ring structures or connected to form a ring through chemical bonds; The substituents of the above substitutions are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Preferably, the Z 1 , Z 2 , Z 3 At most one of them is N; further preferably, the Z 1 , Z 2 , Z 3 Each independently is CR 31 ; More preferably, Z 1 , Z 3 for CH, the Z 2 CR 31 , the R 31 It is one or a combination of two of hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, cyclopentyl, cyclohexyl and adamantyl.

3. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: Ring A or Ring B is a structure represented by Formula A-1 or A-2: Indicates the fusion position, Y is O, S, NR 21 , CR 21 R 22 One of the 21 , R 22 Each is independently selected from any one of hydrogen, C1-C20 straight chain or branched chain alkyl; X 1 -X 4 Each is independently denoted as CR 11 or N; R 11 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, condensed ring aryl, substituted or unsubstituted C3-C30 heteroaryl; each R 11 Same or different, adjacent R 11 The bases are not connected or connected to form a ring through chemical bonds. Preferably, Y is S; the adjacent R 11 The base is not connected. The substituents mentioned above are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

4. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: The compound represented by formula (1) is a compound represented by formula 1-1 to formula 1-5, R 1 , R 1 '、R 2 , R 4 , R 5 , b, d, e, Ar, and M have the same meanings as in formula (1); L, L ’ Each is independently a single bond, methylene, ethylene, propylene, isopropylidene, or ethylidene; R 1 , L and Ar are connected to form a ring or not, R 1 ', L ’ It is connected to Ar to form a ring or not, Preferably R 1 , R 1 ' are each independently selected from a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R 1 , R 1 'Not connected to adjacent groups or connected to form a ring through chemical bonds; More preferably, R 1 , R 1 ' are independently selected from C1-C10 chain alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl; more preferably R 1 , R 1 ' are each independently selected from one or a combination of two of methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, isobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, isopropylphenyl, pyridyl, furyl, and thienyl, The substituents mentioned above are each independently selected from at least one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

5. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: The M group is one selected from the following groups, 6. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: Ar is substituted or unsubstituted and is selected from the following groups: The substitution in the above-mentioned "substituted or unsubstituted" refers to substitution by at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, isobutyl, dimethylpropyl, cyclohexane and adamantane.

7. The boron-nitrogen-containing organic compound according to claim 1, comprising the following specific compounds:

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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