Boron-containing organic compound and application thereof

Abstract

The invention provides a boron-containing organic compound and application thereof, the boron-containing organic compound has a structure as shown in formula I, ring A and ring B are independently selected from one of unsubstituted or R'substituted C6-C60 aromatic rings and unsubstituted or R 'substituted C3-C60 heteroaromatic rings; ar1 is selected from any one of unsubstituted or R '-substituted C6-C60 aryl and unsubstituted or R'-substituted C3-C60 heteroaryl, and Ar1 and an adjacent ring structure are not connected or are connected into a ring through a chemical bond. When the compound is used in an organic electroluminescent device, and particularly used as a luminescent dye material, the efficiency roll-off of the device can be improved, and the service life of the device can be prolonged. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a boron-containing organic compound and its application. Background Art

[0002] The main way for people to obtain information is through vision. Therefore, in the process of human interaction with information, display devices are crucial. Organic light-emitting diodes (OLEDs) have many advantages such as flexibility, self-luminescence, high contrast, large size, and low power consumption, and have become one of the current mainstream display devices.

[0003] In the light-emitting layer of OLED devices, as the red and green light dyes of the three primary colors, since they generally contain heavy atoms such as Ir, Pt, etc., theoretically, 100% internal quantum efficiency can be achieved, the electroluminescence efficiency is relatively high, and the power consumption is low, making them the mainstream of current commercial display devices. However, due to the strong MLCT 3 absorption of green phosphorescent materials, the chromaticity and efficiency of their optoelectronic devices have currently reached bottlenecks and cannot meet higher display requirements. There is an urgent need to develop new technologies to achieve a breakthrough in green performance.

[0004] Recently, researchers such as Takuji Hatakeyama and Junji Kido in Japan reported a series of organic materials DABNA-1 based on boron-containing resonance-type thermally activated delayed fluorescence (TADF) (Adv. Mater., 2016, 28, pp. 2777-2781; J. Mater. Chem. C, 2019, 7, pp. 3082-3089), and its structure is as follows:

[0005]

[0006] The boron atom, nitrogen atom, and phenyl group in this type of compound constitute a rigid polycyclic aromatic skeleton, thus having a relatively high fluorescence quantum yield. Compared with traditional blue fluorescent dyes, this type of compound has a narrower spectrum and excellent color purity. However, the rigid planar structure also leads to a large energy difference between the singlet and triplet energy levels, and the reverse intersystem crossing from the triplet state to the singlet state is relatively slow. After excitons recombine on the dye, it will cause serious efficiency roll-off and the device life is relatively short. In addition, the overly planar rigid structure often also leads to adverse effects such as spectral broadening and red shift due to too high doping concentration.

[0007] There is still much room for improvement in the luminescence performance of existing organic electroluminescent materials. The industry urgently needs to develop new luminescent material systems to meet commercial needs. Boron-containing resonance materials have the advantages of high color purity and high luminescence efficiency, which have attracted extensive attention in the scientific research community and the industrial community. However, due to the relatively planar structural characteristics of resonance dyes, they are extremely prone to molecular aggregation, resulting in a decrease in color purity and a decline in device performance. Therefore, the research on organic electroluminescent materials with better optoelectronic properties remains the research focus in this field. Summary of the Invention

[0008] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a boron-containing organic compound and its application. The boron-containing organic compound has excellent optoelectronic properties. When it is used in an organic electroluminescent device, the device can maintain its efficiency while having a longer lifespan.

[0009] To achieve the purpose of this invention, the following technical solutions are adopted:

[0010] In the first aspect, the present invention provides a boron-containing organic compound, and the boron-containing organic compound has a structure shown in Formula I:

[0011]

[0012] Wherein, ring A and ring B are each independently selected from one of an unsubstituted or R'-substituted C6-C60 aromatic ring and an unsubstituted or R'-substituted C3-C60 heteroaromatic ring;

[0013] Ar1 is selected from any one of an unsubstituted or R''-substituted C6-C60 aryl group and an unsubstituted or R''-substituted C3-C60 heteroaryl group; Ar1 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring;

[0014] X1 is selected from CR 11 or N; R 11 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring;

[0015] Z1, Z2, and Z3 are each independently CR 12 or N; two adjacent Rs 12 are not connected or are connected by a chemical bond to form a ring; R 12 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring;

[0016] R1 and R2 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R”-substituted C1-C20 linear or branched alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C2-C20 alkenyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C1-C20 alkylamino, unsubstituted or R”-substituted C6-C60 arylsilyl, unsubstituted or R”-substituted C6-C30 heteroarylsilyl, unsubstituted or R”-substituted C6-C60 arylamino, unsubstituted or R”-substituted C3-C60 heteroarylamino, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C3-C30 heteroaryloxy, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0017] R1 and R2 are not connected by a chemical bond to form a ring, and at least one of R1 and R2 is not hydrogen;

[0018] R 11 、R 12 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R”-substituted C1-C20 linear or branched alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C2-C20 alkenyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C1-C20 alkylamino, unsubstituted or R”-substituted C6-C60 arylsilyl, unsubstituted or R”-substituted C6-C30 heteroarylsilyl, unsubstituted or R”-substituted C6-C60 arylamino, unsubstituted or R”-substituted C3-C60 heteroarylamino, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C3-C30 heteroaryloxy, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0019] Each of the above R' and R” is independently selected from any one of halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, and unsubstituted or R-substituted C3-C60 heteroaryl; each of the substituents of the substituted ones is independently not connected to the adjacent ring structure or forms a ring through a chemical bond;

[0020] Each R is independently selected from any one of halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two of them. Adjacent Rs are not connected or form a ring through a chemical bond, and the R is not connected to the adjacent ring structure or forms a ring through a chemical bond.

[0021] In the general formula structure of the compound of the present invention, the boron atom contained has a resonance effect with the nitrogen atom in the same ring, and at the same time has a strong central rigid structure, which is beneficial to reducing the Stokes shift of the molecule, enabling the series of materials of the present invention to have the characteristic of narrow spectral emission, and is beneficial to improving the light emission efficiency in the device.

[0022] In the present invention, a class of heterocyclic carbazole substituents is introduced on one side of the boron-containing compound skeleton, which is beneficial to restricting molecular vibration and rotation, narrowing the emission spectrum of the material, and at the same time can improve the molecular transport ability and enhance the carrier balance in the device; at the same time, a class of benzindole substituents is introduced on the other side of the boron-containing compound skeleton, which is beneficial to reducing the triplet energy level, eliminating the delayed fluorescence property, and is beneficial to improving the lifetime of the device. Further, a class of large steric hindrance groups is introduced into the compound of the present invention, so that the steric hindrance effect of the molecule is increased, which can effectively reduce the interaction between dye molecules, help reduce the aggregation and quenching of dye molecule concentration, inhibit the efficiency roll-off of organic electroluminescent devices, and is beneficial to improving the device efficiency.

[0023] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of substituents is as shown above and will not be elaborated one by one.

[0024] In this specification, the expression of Ca - Cb means that the group has a carbon atom number of a - b. Generally, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0025] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure.

[0026] In this specification, "independently of each other" means that when there are multiple subjects, they may be the same or different from each other.

[0027] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression of "hydrogen (H)" includes its isotopes 1 H (protium or H), 2 H (deuterium or D); carbon (C) includes 12 C, 13 C, etc., and will not be elaborated further.

[0028] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0029] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0030] In the present invention, unless otherwise specified, aryl and heteroaryl both include monocyclic and fused-ring cases.

[0031] In the present invention, the C6 - C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0032] The C3 - C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0033] Any of C1-C20 can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0034] Any of C3-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0035] Any of C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] Any of C3-C30 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0037] Any of C2-C10 can be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0038] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and polycyclic aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The so-called monocyclic aryl group means that the molecule contains at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by single bonds. Exemplarily, such as: phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl 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 polycyclic aryl group means that the molecule contains at least two aromatic rings, and the aromatic rings are not independent of each other but are fused together by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, Groups such as a base, a tetracenyl group, and their derivative groups. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; the tetracenyl group is selected from a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. The derivative group of fluorene is selected from a 9,9-dimethylfluorenyl group, a 9,9-diethylfluorenyl group, a 9,9-dipropylfluorenyl group, a 9,9-dibutylfluorenyl group, a 9,9-dipentylfluorenyl group, a 9,9-dihexylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-dinaphthylfluorenyl group, a 9,9'-spirobifluorenyl group, and a benzofluorenyl group.

[0039] The C3-C60 heteroaryl groups mentioned in the present invention include monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by a single bond. Examples of the monocyclic heteroaryl group include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, etc. The fused-ring heteroaryl group means that the molecule contains at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aryl ring), and the two are not independent of each other but are fused to each other by sharing two adjacent atoms. Examples of the fused-ring heteroaryl group include a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuryl group, an isobenzothienyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, a phenazinyl group, a 9-phenylcarbazolyl group, a 9-naphthylcarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, etc.

[0040] Specific examples of the arylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above aryl groups. The number of carbon atoms of the arylene group includes but is not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of the heteroarylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above heteroaryl groups.

[0041] The aryloxy group in the present invention can be a monovalent group composed of the above aryl group, heteroaryl group, and oxygen.

[0042] In the present invention, the arylamino group represents a group formed by substituting one or two hydrogens on the amino group with aryl groups, wherein the connection site of the arylamino group can be connected to the aryl group in the arylamino group or to the N in the arylamino group, and the exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as those above.

[0043] The C6-C30 arylamines mentioned in the present invention include, for example: phenylamine, methylphenylamine, naphthylamine, anthrylamine, phenanthrylamine, biphenylamine, etc.

[0044] The C3-C30 heteroarylamines mentioned in the present invention include, for example: pyridylamine, pyrimidinylamine, dibenzofuranyl amine, etc.

[0045] In the present invention, the linear alkyl group, unless otherwise specified, includes a straight-chain alkyl group and a branched-chain alkyl group. Specifically, the substituted or unsubstituted C1-C30 linear alkyl group is preferably a substituted or unsubstituted C1-C16 linear alkyl group, more preferably a substituted or unsubstituted C1-C10 linear alkyl group. Examples of the substituted or unsubstituted C1-C10 linear alkyl group 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.

[0046] In the present invention, the cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group; wherein, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on the ring; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0047] In this specification, as the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group, examples of the C1-C10 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are preferred, and methoxy is more preferred.

[0048] In this specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group may be silyl groups substituted by the groups exemplified in the above C1-C10 alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0049] In this specification, the C2-C10 alkenyl group is a hydrocarbon group containing at least 1 C═C double bond, and exemplary examples include, but are not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0050] It should be noted that in this application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0051] Further preferably, ring B is selected from an unsubstituted or R'-substituted C6 aromatic ring, an unsubstituted or R'-substituted C5-C6 heteroaromatic ring; R' is selected from halogen, cyano, nitro, hydroxyl, amino, C1-C10 straight-chain or branched-chain alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 aryl ether, C3-C30 heteroaryl ether, C6-C30 arylthioether, C3-C30 heteroarylthioether, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of one or two of them;

[0052] More preferably, ring B is selected from an unsubstituted or R'-substituted C6 aromatic ring; R' is selected from halogen, cyano, C1-C10 straight-chain or branched-chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of one or two of them.

[0053] Furthermore, in the above general formula, ring B is selected from an unsubstituted or R'-substituted C6 aromatic ring, an unsubstituted or R'-substituted C4-C6 heteroaromatic ring;

[0054] R' is selected from any one of halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0055] Preferably, ring B is selected from unsubstituted or R'-substituted C6 aromatic rings;

[0056] R' is selected from any one of halogen, unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C2-C10 alkenyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylsilyl, unsubstituted or R-substituted C1-C10 alkylamino, cyano, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0057] More preferably, R' is selected from any one of unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0058] Further preferably, the compounds of the present invention have the structure shown in the following formula II:

[0059]

[0060] Wherein, the definitions of ring A, X1, Ar1, Z1, Z2, Z3, R1, and R2 are the same as those in formula I;

[0061] R3, R4, R5, and R6 are each independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, and unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substituted groups are each independently not connected to the adjacent ring structure or connected by a chemical bond to form a ring;

[0062] Two adjacent ones of R3, R4, R5, and R6 are connected or not connected.

[0063] Still further, the compounds of the present invention have the structure shown in the following formula III:

[0064]

[0065] Wherein, the definitions of Ar1, X1, Z1, Z2, Z3, R1, and R2 are the same as those in formula I, and R3, R4, R5, and R6 have the same definitions as in formula II;

[0066] X2, X3, X4, and X5 are each independently selected from CR 21 or N;

[0067] R 21Each is independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0068] Continuing preferably, in the above general formula, at least one of Z1, Z2, Z3 is CR 12 ; and at least one CR 12 is a group G, and the G is selected from any one of the following structural formulas G1-G8:

[0069]

[0070] Wherein, * represents the connection site of the group;

[0071] X 11 、X 12 、X 13 、X 14 、X 15 are each independently N or CR 20 ;

[0072] R 20Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C1-C20 straight or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0073] Each R is independently selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, and a combination of one or two of them; adjacent Rs are not connected or connected into a ring through a chemical bond, and the R is not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0074] The two adjacent Rs 20 are not connected or connected into a ring through a chemical bond, and the R 20 is each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0075] R A1 each independently represents a single substitution to the maximum allowable substituent, and R A1 each independently is selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, and any one or a combination of at least two of them;

[0076] R A2 each independently represents a single substitution to the maximum allowable substituent, and RA2 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C1-C20 straight or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substituted groups are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0077] Said R A2 The substituents on each of the substituted groups in it are selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, one or a combination of two; adjacent Rs are not connected or connected into a ring through a chemical bond, and said R is not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0078] Preferably, Z1, Z2, and Z3 are each independently CR 12 , and at least one R in CR 12 is group G; 12

[0079] Preferably, Z1, Z2, and Z3 are each independently selected from CH or CR G , and one of them is CR G ;

[0080] Preferably, Z1 and Z3 are CH, and Z2 is CR G .

[0081] More preferably, the compound of the present invention has the structure shown in Formula IV:

[0082]

[0083] Among them, ring A, X1, Ar1, Z1, Z2, Z3, R1, and R2 have the same defined ranges as in Formula I;

[0084] R3, R4, R5, and R6 have the same defined ranges as in Formula II;

[0085] G is selected from any one of the structural formulas G1 - G8;

[0086] Preferably, the connecting position of G is the para-position of the carbon atom connected to the B atom;

[0087] Preferably, when G is selected from the structural formula G1, X 11 、X 12 、X 13 、X 14 、X 15 are each independently CR 20 ; R 20 are each independently selected from hydrogen, halogen, cyano, unsubstituted or R-substituted C1-C10 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylsilyl, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substituted ones are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0088] More preferably, in the above general formula, X1 is selected from CR 11 ; preferably, R 11 is selected from hydrogen, halogen, cyano, unsubstituted or R''-substituted C1-C10 straight-chain or branched-chain alkyl, unsubstituted or R''-substituted C3-C10 cycloalkyl, unsubstituted or R''-substituted C6-C20 aryl, unsubstituted or R''-substituted C3-C20 heteroaryl; more preferably hydrogen;

[0089] Each of R1 and R2 is independently selected from any one of hydrogen, unsubstituted or R”-substituted C1-C20 linear or branched alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl. R1 and R2 are not connected by a chemical bond to form a ring, and at least one of R1 and R2 is not hydrogen; each of R” is independently selected from any one of halogen, cyano, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C6-C60 aryl, and unsubstituted or R-substituted C3-C60 heteroaryl.

[0090] Further preferably, in the above general formula, one group of any two adjacent groups among R3, R4, R5, and R6 is connected by a chemical bond to form a ring C, and the other groups except for forming the ring C are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; the ring C has the structure shown in Formula C:

[0091]

[0092] The dotted line represents a fused bond;

[0093] Y1, Y2, Y3, and Y4 are each independently N or CR 22 ;

[0094] R 22 is each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of any one or at least two of them; adjacent Rs 22 are not connected or are connected by a chemical bond to form a ring, and the Rs 22 are not connected to the adjacent ring structure or are connected by a chemical bond to form a ring;

[0095] M1 and M2 are each independently selected from any one of a single bond, NR 14 , O, S, or CR 15 R 16 , and M1 and M2 are not both a single bond at the same time;

[0096] R 14 、R 15 、R 16Each independently selected from any one or a combination of at least two of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl;

[0097] Preferably, M1 is selected from NR 14 , O, S, or CR 15 R 16 Any one of them, and M2 is a single bond.

[0098] More preferably, in the above general formula, Ar1 has the structure shown in Formula D:

[0099]

[0100] Wherein, * represents the connection site of the group;

[0101] Q1, Q2, Q3, Q4, Q5 are each independently N or CR 23 ;

[0102] R 23 Each independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0103] R is each independently selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, any one or a combination of at least two of them; adjacent Rs are not connected or connected into a ring through a chemical bond, and the R is not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0104] Preferably, at most one of Q1, Q2, Q3, Q4, and Q5 is N;

[0105] Preferably, Q1, Q2, Q3, Q4, and Q5 are each independently CR 23 ;

[0106] More preferably, R 23 is selected from any one of unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, and unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected by a chemical bond to form a ring;

[0107] Each R is independently selected from halogen, cyano, C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, and adjacent Rs are not connected or connected by a chemical bond to form a ring, and the R is not connected to the adjacent ring structure or connected by a chemical bond to form a ring.

[0108] Further preferably, the compounds of the present invention are selected from the structures shown in the following formula IV-1 or formula IV-2,

[0109]

[0110] M3 is selected from any one of a single bond, NR 17 , O, S, Se, CR 18 R 19 or SiR 13 R 13 ’ ;

[0111] Preferably, it has the structure shown in the following formula IV-2,

[0112] More preferably, M3 in formula (2) is a single bond.

[0113] Further preferably, the compounds of the present invention are selected from the structures shown in the following formula V-1 to formula V-4,

[0114]

[0115] Preferably, M1 is selected from NR 14 , O, CR 15 R 16 Any one of them, and more preferably, M1 is NR 14 ;

[0116] Preferably, X1 is CR 11 , and the R 11 is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl, and more preferably hydrogen;

[0117] Preferably, Y1, Y2, Y3, and Y4 are each independently selected from CR 22 ;

[0118] The R 22 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two of them; adjacent R 22 are not connected or are connected by a chemical bond to form a ring, and the R 22 is not connected or is connected by a chemical bond to the adjacent ring structure to form a ring.

[0119] Preferably, the R 22 are each independently selected from any one of hydrogen, halogen, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two of them; adjacent R 22 are not connected or are connected by a chemical bond to form a ring, and the R 22 is not connected or is connected by a chemical bond to the adjacent ring structure to form a ring; more preferably hydrogen;

[0120] X2, X3, X4, and X5 are each independently selected from CR 21 ;

[0121] Preferably, the R 21Each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and is further preferably hydrogen;

[0122] Preferably, Q1, Q2, Q3, Q4, Q5 are each independently CR 23 ;

[0123] More preferably, the R 23 is selected from hydrogen, halogen, unsubstituted or R-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0124] R is each independently selected from halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; adjacent Rs are not connected or connected into a ring through a chemical bond, and the R is not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0125] Preferably, more preferably, the R 23 is selected from hydrogen, halogen, unsubstituted or R-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0126] Each R is independently selected from any one of halogen, cyano, C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Adjacent Rs are not connected or are connected by a chemical bond to form a ring. The R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring;

[0127] More preferably, R 23 is hydrogen.

[0128] More preferably, each of R1 and R2 is independently selected from any one of unsubstituted or R''-substituted C1-C10 linear or branched alkyl, unsubstituted or R''-substituted C6-C20 aryl, and unsubstituted or R''-substituted C3-C20 heteroaryl;

[0129] Preferably, each of R1 and R2 is independently selected from substituted or unsubstituted C1-C6 linear or branched alkyl and any one of the following; represents the connection site of the group;

[0130] R X is independently selected from any one of unsubstituted or R'-substituted C1-C20 linear or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl;

[0131] n is an integer from 0 to 5;

[0132] Preferably, at least one of R1 and R2 is selected from More preferably, each of R1 and R2 is independently selected from

[0133] Preferably, each of R1 and R2 is independently selected from and any one of the following;

[0134] More preferably, the compound of the present invention is selected from the structures shown in any one of the following formulas VI-1, VI-2, VI-3, and VI-4:

[0135]

[0136] wherein Y1, Y2, Y3, and Y4 have the same defined range as in formula C;

[0137] M1 is selected from NR 14 , O, S, or CR 15 R16 any one of the following;

[0138] Q1, Q2, Q3, Q4, Q5 have the same defined range as in formula D;

[0139] R7 is selected from any one of hydrogen, halogen, unsubstituted or R''-substituted C1-C10 linear or branched alkyl, unsubstituted or R''-substituted C3-C10 cycloalkyl, unsubstituted or R''-substituted C6-C20 aryl, unsubstituted or R''-substituted C3-C20 heteroaryl;

[0140] R8 and R9 are each independently selected from halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond;

[0141] Preferably, the connecting position of G is the para position of the carbon atom connected to the B atom;

[0142] Preferably, G has the structure shown in any one of G1-G5, and preferably has the structure shown in G1;

[0143] Preferably, the said X 11 , X 12 , X 13 , X 14 , X 15 are each independently selected from CR 20 ;

[0144] Preferably, the number of CH in the said X 11 , X 12 , X 13 , X 14 and X 15 is 2-5, and more preferably 3-4;

[0145] Preferably, the said R 20Each independently selected from any one of hydrogen, cyano, halogen, unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C2-C10 alkenyl, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl;

[0146] Preferably, the R G is selected from any one of the following groups:

[0147]

[0148]

[0149] represents the connection site of the group; preferably, the R G is selected from any one of the following groups:

[0150]

[0151]

[0152] Preferably, Y1, Y2, Y3, Y4 are each independently CR 22 ; more preferably, Y1, Y2, Y3, Y4 are all CH;

[0153] Preferably, R7 is hydrogen; more preferably, R7, R8, R9 are all hydrogen.

[0154] Furthermore, the boron-containing organic compound of the present invention has a structure shown in any one of M1-M337 as follows:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] In a second aspect, the present invention provides an application of a boron-containing organic compound as described in the first aspect, wherein the boron-containing organic compound is applied to an organic electronic device.

[0174] 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 an electronic paper, and more preferably an organic electroluminescent device.

[0175] Preferably, the boron-containing organic compound is applied to an organic electroluminescent device.

[0176] Preferably, the boron-containing organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0177] Preferably, the boron-containing organic compound is used as a dye (also referred to as "doping material", "dopant", "guest material") in the light-emitting layer of an organic electroluminescent device.

[0178] In a third aspect, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer includes at least one boron-containing organic compound as described in the first aspect.

[0179] Preferably, the organic layer includes at least one boron-containing organic compound having a structure shown in M1-M337.

[0180] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one boron-containing organic compound as described in the first aspect. More preferably, it includes at least one boron-containing organic compound having the structure shown in M1-M337.

[0181] Preferably, the light-emitting layer includes a host material and a dopant material, and the dopant material includes at least one boron-containing organic compound as described in the first aspect.

[0182] Preferably, the compound provided by the present invention is used as a fluorescent dopant material (fluorescent dye) of the light-emitting layer.

[0183] Preferably, the mass percentage content of the dopant material in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%, etc. More preferably, it is 0.3-3%.

[0184] Preferably, the host material includes any one or a combination of at least two of a P-type host material, an N-type host material, and a single-molecule exciplex host material.

[0185] Preferably, the light-emitting layer further includes a sensitizer.

[0186] Preferably, the sensitizer includes any one or a combination of at least two of a thermally activated delayed fluorescence material and a phosphorescent material.

[0187] Preferably, the mass percentage content of the sensitizer in the light-emitting layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0188] Preferably, the sensitizer includes a phosphorescent material, and the mass percentage content of the phosphorescent material in the light-emitting layer is 0.1-10%.

[0189] Preferably, the sensitizer is a thermally activated delayed fluorescence material, and the mass percentage content of the thermally activated delayed fluorescence material in the light-emitting layer is 1-40%.

[0190] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0191] Preferably, the hole transport region includes any one or a combination of at least two of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0192] Preferably, the electron transport region includes any one or a combination of at least two of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0193] In a preferred technical solution, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one boron-containing organic compound as described in the first aspect, and further preferably contains at least one boron-containing organic compound having the structure shown by M1-M337.

[0194] In a preferred technical solution, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode arranged in sequence; 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 arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one boron-containing organic compound as described in the first aspect, and further preferably contains at least one boron-containing organic compound having the structure shown by M1-M337.

[0195] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, thin film transistors (TFTs) can also be provided on the substrate for a display.

[0196] 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 the anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc., and any combination thereof can be used. When the first electrode is used as the 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), etc., and any combination thereof can be used.

[0197] The organic layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compounds used as the organic layer can be organic small molecules, organic macromolecules, or polymers, and combinations thereof.

[0198] 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 multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); where the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0199] 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 poly(phenylene vinylene), 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, where the aromatic amine derivatives include the compounds shown as HT-1 to HT-51 below; or any combination thereof.

[0200]

[0201]

[0202]

[0203]

[0204] 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 adopt one or more of the above-mentioned compounds of HT-1 to HT-51, or one or more of the following compounds of HI-1 - HI-3; it can also adopt one or more of the compounds of HT-1 to HT-51 doped with one or more of the following compounds of HI-1 - HI-3.

[0205]

[0206] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and can also include a host material and a sensitizer material at the same time. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0207] According to different technologies, the light-emitting layer material can be a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermally activated delayed fluorescence material, or other different materials. In an OLED device, a single light-emitting technology can be adopted, 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.

[0208] In one aspect of the present invention, the host of the light-emitting layer can be selected from, but not limited to, one or a combination of more than one of PH-1 to PH-85.

[0209]

[0210]

[0211]

[0212]

[0213] In one aspect of the present invention, the sensitizer of the light-emitting layer can be selected from TADF materials or phosphorescent materials, and the TADF materials can be selected from, but not limited to, one or a combination of more than one of the following listed TDE1-TDE37.

[0214]

[0215]

[0216] In one aspect of the present invention, the sensitizer of the light-emitting layer can be selected from TADF materials and phosphorescent materials, and the phosphorescent materials can be selected from, but not limited to, one or a combination of more than one of the following listed GPD-1 to GPD-47.

[0217]

[0218]

[0219] In one aspect of the present invention, the electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer can be made of, but not limited to, one or more compounds of HT-1 to HT-51 described above, or can be made of, but not limited to, one or more compounds of PH-47 to PH-77 described above; it can also be made of a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77.

[0220] 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 multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0221] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0222]

[0223]

[0224]

[0225]

[0226] In one aspect of the present invention, the hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may be made of, but not limited to, one or more compounds among the above ET-1 to ET-73, or may be made of, but not limited to, one or more compounds among PH-1 to PH-46; it may also be made of, but not limited to, a mixture of one or more compounds among ET-1 to ET-73 and one or more compounds among PH-1 to PH-46.

[0227] The device may further include an electron injection layer between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations listed below.

[0228] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb, Mg.

[0229] In a fourth aspect, the present invention provides a display device, which includes the organic electroluminescent device as described in the third aspect.

[0230] The preparation process of the compounds of the present invention is simple and easy to implement, and the raw materials are easily available, which is suitable for mass production and amplification.

[0231] In the boron-containing organic compound provided by the present invention, through the design and mutual compounding of a specific fused-ring skeleton structure and groups, it has excellent optoelectronic properties and narrow spectral characteristics. The boron-containing organic compound is used in an organic electroluminescent device and can be used as a fluorescent doping material for a light-emitting layer, enabling the device to have high color purity, suppressing the efficiency roll-off of the device, improving the light-emitting efficiency of the device, extending the service life, reducing the voltage and energy consumption, and fully meeting the requirements of current display devices and panels for high-performance materials.

[0232] Introducing a fused structure benzindole on one side of the B-N skeleton structure can effectively reduce the T1 energy level of the material and suppress stability problems (such as TTA, TPA, etc. in the device) caused by the high-energy T1 energy level of the molecule, which is beneficial to the improvement of the device life.

[0233] The R1 and R2 groups can play a role in adjusting the molecular energy level and molecular steric hindrance, which is beneficial to the improvement of the device efficiency; introducing a fused structure shown in Formula C on one side of the B-N skeleton structure is beneficial to restricting the structural relaxation of the molecule in the excited state, narrowing the emission spectrum of the material, and at the same time can improve the molecular transport ability, enhance the carrier balance in the device, and is beneficial to the improvement of the device efficiency. Specific embodiments

[0234] The following will detail the specific preparation methods of the above new compounds of the present invention with multiple synthesis examples as examples, but the preparation methods of the present invention are not limited to these synthesis examples.

[0235] It should be noted that obtaining this compound is not limited to the synthesis methods and raw materials used in the present invention. Those skilled in the art can also select other methods or routes to obtain the compounds proposed by 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 self-made based on these raw material products according to well-known methods.

[0236] 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 purchased from Sinopharm Chemical Reagent Co., Ltd., TCI Co., Ltd., Shanghai Bide Pharmaceutical Co., Ltd., J&K Scientific Ltd., etc.

[0237] The following briefly describes the synthesis method of the compound of the present invention.

[0238] Synthesis examples

[0239] Synthesis route:

[0240]

[0241] In the present invention, the intermediate and compound are analyzed and detected using an ABSCIEX mass spectrometer (4000 QTRAP).

[0242] Synthesis Example 1

[0243] Synthesis of Compound M3:

[0244]

[0245] Synthesis of Intermediate M3-1:

[0246] Put SM2 (16.55 g) and DMF (165 mL) into a 500 mL three-necked flask, displace with nitrogen three times, stir and cool down to 0 °C, and add sodium hydride (2.07 g) to it in batches. After the addition is complete, react at 0 °C for 1 hour and record it as Solution A;

[0247] Put SM1 (10 g) and DMF (100 mL) into another 500 mL three-necked flask, displace with nitrogen three times. Cool down to 0 °C, and dropwise add Solution A to the system. After the addition is complete, react at 0 °C for 5 hours.

[0248] Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and purify it by column chromatography to obtain 12.5 g of Intermediate M3-1 as a white solid.

[0249] Synthesis of Intermediate M3-2:

[0250] Put M3-1 (10 g), SM3 (6.5 g), cesium carbonate (13.2), and DMF (100 mL) into a 250 mL single-necked flask, displace with nitrogen three times, and heat up to 100 °C to react overnight.

[0251] Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and recrystallize it with toluene / ethanol to obtain 14.5 g of Intermediate M3-2 as a white solid.

[0252] Synthesis of Product M3:

[0253] Add intermediate M3-2 (10 g) to a 250 mL three-necked flask, add xylene (100 mL), displace with nitrogen 3 times, cool the reaction system to -40 °C, dropwise add n-butyllithium (7.58 mL) to the system, and then heat to 60 °C and react for 2.5 h. Cool the temperature of the reaction system to -40 °C, add boron tribromide (2.43 mL), and then heat to 60 °C and react for 1.5 h. Cool the system temperature to -40 °C again and add diisopropylethylamine (6.28 mL). Finally, heat the reaction system to 130 °C and react for 12 h. After the reaction is cooled to room temperature, dropwise add methanol (180 mL) to the system, filter and dry, and recrystallize with o-dichlorobenzene / ethanol to obtain 2.8 g of an orange-red solid, which is the target product M3. The molecular ion mass determined by mass spectrometry: 720.38 (theoretical value: 720.27).

[0254] Synthesis Example 2

[0255] Synthesis of Compound M45:

[0256]

[0257] Synthesis of Intermediate M45-1:

[0258] The synthesis procedure is the same as that of M3-1, and the intermediate M45-1 13.1 g of white solid is obtained by column chromatography purification.

[0259] Synthesis of Intermediate M45-2:

[0260] Put M45-1 (10 g), SM3 (6.06 g), cesium carbonate (11.88 g), and DMF (100 mL) into a 250 mL single-necked flask, displace with nitrogen 3 times, and heat to 100 °C and react overnight.

[0261] Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and recrystallize with toluene / ethanol to obtain 13.6 g of white solid of intermediate M45-2.

[0262] Synthesis of Product M45:

[0263] The synthesis procedure is the same as that of M3, and recrystallize with o-dichlorobenzene / ethanol to obtain 2.3 g of an orange-red solid, which is the target product M45. The molecular ion mass determined by mass spectrometry: 789.46 (theoretical value: 789.33).

[0264] Synthesis Example 3

[0265] Synthesis of Compound M88:

[0266]

[0267] Synthesis of Intermediate M88-1:

[0268] Add SM2 (21 g) and DMF (210 mL) into a 500 mL three-necked flask, displace the air with nitrogen three times, stir and cool down to 0 °C, and add sodium hydride (2.64 g) to it in batches. After the addition is complete, react at 0 °C for 1 hour and record it as A;

[0269] Add SM1 (15 g) and DMF (150 mL) into another 500 mL three-necked flask, displace the air with nitrogen three times. Cool down to 0 °C, and add A dropwise to the system. After the addition is complete, react at 0 °C for 5 hours.

[0270] Pour the reaction solution into water for quenching, filter, collect the solid, dry it, and purify it by column chromatography to obtain 113.8 g of intermediate M88-1 as a white solid.

[0271] Synthesis of intermediate M88-2:

[0272] Add M88-1 (10 g), SM3 (4.88 g), cesium carbonate (12.37 g), and DMF (100 mL) into a 250 mL single-necked flask, displace the air with nitrogen three times, and heat up to 100 °C to react overnight.

[0273] Pour the reaction solution into water for quenching, filter, collect the solid, dry it, and recrystallize it with toluene / ethanol to obtain 13.3 g of intermediate M88-2 as a white solid.

[0274] Synthesis of intermediate M88-3:

[0275] Add intermediate M88-2 (12 g), SM4 (3.68 g), tetrakis(triphenylphosphine)palladium (363 mg), potassium carbonate (3.26 g), dioxane (120 mL), and water (40 mL) into a 250 ml single-necked flask, displace the air with nitrogen three times, and heat up to reflux to react overnight.

[0276] Concentrate the reaction solution under reduced pressure to remove dioxane, add water to the remaining residue and filter, collect the solid, dry it, pass it through a flash column with dichloromethane, concentrate to dryness, and recrystallize it with toluene / ethanol to obtain 11.5 g of intermediate M88-3 as a white solid.

[0277] Synthesis of product M88:

[0278] Add the intermediate M88-3 (10 g) to a 250 mL three-necked flask, add xylene (100 mL), displace with nitrogen three times, cool the reaction system to -40 °C, dropwise add tert-butyllithium (17.9 mL) to the system, and then heat to 60 °C for reaction for 2.5 h. Cool the temperature of the reaction system to -40 °C, add boron tribromide (3.31 mL), and then heat to 60 °C for reaction for 1.5 h. Cool the system temperature to -40 °C again and add diisopropylethylamine (9.5 mL). Finally, heat the reaction system to 130 °C for reaction for 12 h. After the reaction is cooled to room temperature, dropwise add methanol (180 mL) to the system, filter and dry, and recrystallize with o-dichlorobenzene / ethanol to obtain 3.1 g of an orange-red solid, which is the target product M88. The molecular ion mass determined by mass spectrometry: 846.66 (theoretical value: 846.38).

[0279] Synthesis Example 4

[0280] Synthesis of Compound M124:

[0281]

[0282] Synthesis of Intermediate M124-1:

[0283] The synthesis procedure is the same as that of M88-1, and the intermediate M124-1 13.6 g of white solid is obtained by column chromatography purification.

[0284] Synthesis of Intermediate M124-2:

[0285] Put M124-1 (9.5 g), SM3 (5.11 g), cesium carbonate (11.75 g), and DMF (95 mL) into a 250 mL single-necked flask, displace with nitrogen three times, and heat to 100 °C for reaction overnight.

[0286] Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and recrystallize with toluene / ethanol to obtain the intermediate M124-2 12.7 g of white solid.

[0287] Synthesis of Intermediate M124-3:

[0288] Add the intermediate M124-2 (11 g), SM4 (2.25 g), tetrakis(triphenylphosphine)palladium (322 mg), potassium carbonate (2.89 g), dioxane (110 mL), and water (37 mL) to a 250 ml single-necked flask, displace with nitrogen three times, and heat to reflux for reaction overnight.

[0289] Concentrate the reaction solution under reduced pressure to remove dioxane, add water to the remaining residue and filter, collect the solid and dry it, use dichloromethane for flash column chromatography, concentrate to dryness, and recrystallize with toluene / ethanol to obtain the intermediate M124-3 9.7 g of white solid.

[0290] Synthesis of Product M124:

[0291] The synthesis procedure is the same as that of M88. Recrystallization from o - dichlorobenzene / ethanol gave 2.4 g of an orange - red solid, which is the target product M124. The molecular ion mass determined by mass spectrometry: 785.56 (theoretical value: 785.30).

[0292] Synthesis Example 5

[0293] Synthesis of Compound M193:

[0294]

[0295] Synthesis of Intermediate M193 - 1:

[0296] The synthesis procedure is the same as that of M88 - 1. Purification by column chromatography gave 14.1 g of a white solid of Intermediate M193 - 1.

[0297] Synthesis of Intermediate M193 - 2:

[0298] Charge M193 - 1 (12.5 g), SM3 (7.89 g), cesium carbonate (15.46 g), and DMF (125 mL) into a 250 - mL single - necked flask. Replace the air with nitrogen three times and heat to 100 °C for overnight reaction.

[0299] Pour the reaction solution into water for quenching, filter, collect the solid, dry it, and recrystallize from toluene / ethanol to obtain 17.5 g of a white solid of Intermediate M193 - 2.

[0300] Synthesis of Intermediate M193 - 3:

[0301] Charge Intermediate M193 - 2 (13 g), SM4 (5.29 g), tetrakis(triphenylphosphine)palladium (358 mg), potassium carbonate (3.21 g), dioxane (130 mL), and water (44 mL) into a 250 - ml single - necked flask. Replace the air with nitrogen three times and heat to reflux for overnight reaction.

[0302] Concentrate the reaction solution under reduced pressure to remove dioxane. Add water to the remaining residue, filter, collect the solid, dry it, use dichloromethane for flash column chromatography, concentrate to dryness, and recrystallize from toluene / ethanol to obtain 13.6 g of a white solid of Intermediate M193 - 3.

[0303] Synthesis of Product M193:

[0304] The synthesis procedure is the same as that of M88. Recrystallization from o - dichlorobenzene / ethanol gave 2.8 g of an orange - red solid, which is the target product M193. The molecular ion mass determined by mass spectrometry: 997.68 (theoretical value: 997.46).

[0305] Device Example

[0306] An organic electroluminescent device, whose structure includes an anode 1 (ITO), a hole injection layer 2, a hole transport layer 3, an electron blocking layer 4, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8, and a cathode 9 (Al) that are stacked in sequence. The preparation method of the organic electroluminescent device is as follows:

[0307] (1) Ultrasonically treat the glass substrate coated with the ITO transparent conductive layer in a commercial cleaning agent, rinse it in deionized water, ultrasonically degrease it in an acetone / ethanol mixed solvent, bake it in a clean environment until all moisture is removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam;

[0308] (2) Place the glass substrate with the anode in a vacuum chamber, evacuate to 1×10 -5 Pa, and vacuum deposit a mixture of HT-4:HI-3 (97 / 3, w / w) on the anode layer film as the hole injection layer at a deposition rate of 0.1 nm / s and a deposited film thickness of 10 nm;

[0309] (3) Vacuum deposit the compound HT-4 on the hole injection layer as the hole transport layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 60 nm;

[0310] (4) Vacuum deposit the compound HT-40 on the hole transport layer as the electron blocking layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 5 nm;

[0311] (5) Vacuum deposit the light-emitting layer on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a fluorescent dye (also known as "fluorescent dopant"). Using the method of co-evaporation from multiple sources, adjust the doping ratio by adjusting the deposition rate of each material. The deposition rate is 0.1 nm / s and the total deposited film thickness is 40 nm;

[0312] The light-emitting layer adopts the technology of phosphorescent sensitized luminescence. The ratio of the host material, phosphorescent sensitizer, and fluorescent dye is 94.2:5:0.8 (w / w / w); among them, the host material is a mixed host of PH-61:PH-3 (50 / 50, w / w), the phosphorescent sensitizer is GPD-41, and the fluorescent dye is the boron-containing organic compound M3 provided by the present invention;

[0313] (6) Vacuum deposit the compound ET-23 on the light-emitting layer as the hole blocking layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 5 nm;

[0314] (7) Vacuum deposit a mixture of the compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as the electron transport layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 25 nm;

[0315] (8) Vacuum deposit LiF as the electron injection layer on the electron transport layer at a deposition rate of 0.1 nm / s and a thickness of 1 nm;

[0316] (9) Vacuum deposit an Al layer with a thickness of 150 nm as the cathode of the device on the electron injection layer at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0317] Device Examples 2 - 17, Device Comparative Examples 1 - 2

[0318] An organic electroluminescent device, which is different from Device Example 1 only in that the fluorescent dyes in the light-emitting layer are the compounds shown in Table 1 respectively; other layers, thicknesses, materials and preparation methods are the same as those in Device Example 1.

[0319]

[0320] Performance test of the device:

[0321] At the same brightness, use a digital source meter and a luminance meter to measure the driving voltage, the lifetime of the device and the external quantum efficiency of each organic electroluminescent device. Specifically, increase the voltage at a rate of 0.1 V per second, and measure the voltage when the current density of the organic electroluminescent device reaches 10 mA / cm 2 That is the driving voltage, and at the same time measure the luminous brightness and the external quantum efficiency (EQE, %) at this time; The LT95 lifetime test is as follows: Use a luminance meter at a brightness of 10000 cd / m 2 Keep a constant current and measure the time when the brightness of the organic electroluminescent device drops to 9500 cd / m 2 The unit is h; In Table 1, the measured value of the LT95 lifetime of Comparative Example 2 is recorded as 1.00, and the LT95 lifetimes of Device Examples 1 - 17 are all the ratios of their respective measured values to the measured value of Comparative Example 2 (relative lifetime);

[0322] The performance of the organic electroluminescent device is shown in Table 1 below:

[0323]

[0324]

[0325] Compared with Comparative Example 1, in the present invention, a fused structure benzindole is introduced on one side of the B-N skeleton structure of the compound. The fused position of the benzene ring is at the 4,5 positions of indole. Compared with Comparative Example 1, the molecular planarity is better and the molecule is more stable, which is beneficial to improving the lifetime of the device. In addition, good molecular planarity is beneficial to improving the molecular carrier transport ability and reducing the device voltage.

[0326] Compared with Comparative Example 2, a fused structure benzindole is introduced on one side of the B-N skeleton structure of the compound provided by the present invention, which reduces the T1 energy level of the material, inhibits the stability problems caused by the high-energy T1 energy level, and is beneficial to the improvement of the device lifetime. In addition, such groups have good molecular planarity, which is beneficial to the improvement of the molecular carrier transport ability and the reduction of the device voltage.

[0327] The above results show that when the novel organic material of the present invention is used in an organic light-emitting device, Examples 1-17 can effectively improve the lifetime compared with Comparative Examples 1-2, and it is a green light material with good performance.

[0328] The present invention illustrates the detailed method of the present invention through the above embodiments, but the present invention is not limited to the above detailed method, that is, it does not mean that the present invention must rely on the above detailed method to be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent substitution of each raw material 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 the disclosure scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, It has the structure shown in Formula I: Wherein, ring A and ring B are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring, or an unsubstituted or R'-substituted C3-C60 heteroaromatic ring; Ar1 is selected from any one of an unsubstituted or R''-substituted C6-C60 aryl group, or an unsubstituted or R''-substituted C3-C60 heteroaryl group; Ar1 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; X1 is selected from CR 11 or N; R 11 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Z1, Z2, and Z3 are each independently CR 12 or N; two adjacent Rs 12 are not connected or are connected by a chemical bond to form a ring; R 12 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, an unsubstituted or R''-substituted C1-C20 straight-chain or branched-chain alkyl group, an unsubstituted or R''-substituted C3-C20 cycloalkyl group, an unsubstituted or R''-substituted C2-C20 alkenyl group, an unsubstituted or R''-substituted C1-C20 alkoxy group, an unsubstituted or R''-substituted C1-C20 alkylsilyl group, an unsubstituted or R''-substituted C1-C20 alkylamino group, an unsubstituted or R''-substituted C6-C60 arylsilyl group, an unsubstituted or R''-substituted C6-C30 heteroarylsilyl group, an unsubstituted or R''-substituted C6-C60 arylamino group, an unsubstituted or R''-substituted C3-C60 heteroarylamino group, an unsubstituted or R''-substituted C6-C30 aryloxy group, an unsubstituted or R''-substituted C3-C30 heteroaryloxy group, an unsubstituted or R''-substituted C6-C60 aryl group, or an unsubstituted or R''-substituted C3-C60 heteroaryl group; Said R1 and R2 are not connected by a chemical bond to form a ring, and at least one of R1 and R2 is not hydrogen; R 11 、R 12 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R”-substituted C1-C20 linear or branched alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C2-C20 alkenyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C1-C20 alkylamino, unsubstituted or R”-substituted C6-C60 arylsilyl, unsubstituted or R”-substituted C6-C30 heteroarylsilyl, unsubstituted or R”-substituted C6-C60 arylamino, unsubstituted or R”-substituted C3-C60 heteroarylamino, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C3-C30 heteroaryloxy, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl; Said R' and R'' are each independently selected from halogen, an unsubstituted or R-substituted C1-C20 straight-chain or branched-chain alkyl group, an unsubstituted or R-substituted C3-C20 cycloalkyl group, an unsubstituted or R-substituted C2-C20 alkenyl group, an unsubstituted or R-substituted C1-C20 alkoxy group, an unsubstituted or R-substituted C1-C20 alkylsilyl group, an unsubstituted or R-substituted C1-C20 alkylamino group, cyano, nitro, hydroxyl, amino, an unsubstituted or R-substituted C6-C30 arylsilyl group, an unsubstituted or R-substituted C6-C30 heteroarylsilyl group, an unsubstituted or R-substituted C6-C30 arylamino group, an unsubstituted or R-substituted C3-C30 heteroarylamino group, an unsubstituted or R-substituted C6-C30 aryloxy group, an unsubstituted or R-substituted C3-C30 heteroaryloxy group, an unsubstituted or R-substituted C6-C60 aryl group, or an unsubstituted or R-substituted C3-C60 heteroaryl group; the substituents of said substitution are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; Each R is independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Adjacent Rs are not connected or are connected by a chemical bond to form a ring, and the R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring.

2. The boron-containing organic compound according to claim 1, characterized in that, The ring B is selected from an unsubstituted or R'-substituted C6 aryl ring or an unsubstituted or R'-substituted C4-C6 heteroaryl ring. R' is selected from any one of halogen, an unsubstituted or R-substituted C1-C20 straight-chain or branched alkyl, an unsubstituted or R-substituted C3-C20 cycloalkyl, an unsubstituted or R-substituted C2-C20 alkenyl, an unsubstituted or R-substituted C1-C20 alkoxy, an unsubstituted or R-substituted C1-C20 alkylsilyl, an unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, an unsubstituted or R-substituted C6-C30 arylsilyl, an unsubstituted or R-substituted C6-C30 heteroarylsilyl, an unsubstituted or R-substituted C6-C30 arylamino, an unsubstituted or R-substituted C3-C30 heteroarylamino, an unsubstituted or R-substituted C6-C30 aryloxy, an unsubstituted or R-substituted C3-C30 heteroaryloxy, an unsubstituted or R-substituted C6-C60 aryl, and an unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring. Preferably, the ring B is selected from an unsubstituted or R'-substituted C6 aryl ring. R' is selected from any one of halogen, an unsubstituted or R-substituted C1-C10 straight-chain or branched alkyl, an unsubstituted or R-substituted C3-C10 cycloalkyl, an unsubstituted or R-substituted C2-C10 alkenyl, an unsubstituted or R-substituted C1-C10 alkoxy, an unsubstituted or R-substituted C1-C10 alkylsilyl, an unsubstituted or R-substituted C1-C10 alkylamino, cyano, an unsubstituted or R-substituted C6-C30 arylsilyl, an unsubstituted or R-substituted C6-C30 heteroarylsilyl, an unsubstituted or R-substituted C6-C30 arylamino, an unsubstituted or R-substituted C3-C30 heteroarylamino, an unsubstituted or R-substituted C6-C30 aryloxy, an unsubstituted or R-substituted C3-C30 heteroaryloxy, an unsubstituted or R-substituted C6-C30 aryl, and an unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring. More preferably, R' is selected from any one of unsubstituted or R-substituted C1-C10 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, and unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substituted ones are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

3. The boron-containing organic compound according to claim 1, wherein It has the structure shown in Formula II below: Wherein, the defined ranges of ring A, X1, Ar1, Z1, Z2, Z3, R1, and R2 are the same as those defined in Formula I; R3, R4, R5, and R6 are each independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, and unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substituted ones are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Two adjacent ones among R3, R4, R5, and R6 are connected or not connected.

4. The boron-containing organic compound according to claim 3, characterized in that, It has the structure shown in Formula III below: Wherein, the defined ranges of Ar1, X1, Z1, Z2, Z3, R1, and R2 are the same as those defined in Formula I, and R3, R4, R5, and R6 have the same defined ranges as those in Formula II; X2, X3, X4, and X5 are each independently selected from C, R 21 or N; R 21 each independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or are connected into a ring through a chemical bond.

5. The boron-containing organic compound according to any one of claims 1-4, characterized in that, At least one of Z1, Z2, and Z3 is CR 12 ; and at least one CR 12 is a group G, and the G is selected from any one of the following structural formulas G1 - G8: Wherein, * represents the connection site of the group; X 11 、 X 12 、 X 13 、 X 14 、 X 15 each independently is N or CR 20 ; R 20 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Each of the Rs is independently selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 straight-chain or branched-chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of one or two of them. The adjacent Rs are not connected or connected into a ring through a chemical bond, and the R is not connected to the adjacent ring structure or connected into a ring through a chemical bond; The two adjacent Rs 20 are not connected or are connected by a chemical bond to form a ring, and each of the Rs 20 is independently not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; R A1 each independently represents a mono-substituted to maximum allowable substituent, R A1 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or any combination of at least two of these; R A2 each independently represents a mono-substituted to maximally allowable substituent, R A2 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or are connected into a ring through a chemical bond; The R A2 The substituents on each of the substituted groups in are selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched-chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. The adjacent Rs are not connected or are connected by a chemical bond to form a ring. The R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring. Preferably, each of Z1, Z2, and Z3 is independently CR 12 , and at least one R 12 in CR 12 is a group G; Preferably, each of Z1, Z2, and Z3 is independently selected from CH or CR G , and one of them is CR G ; Preferably, Z1 and Z3 are CH, and Z2 is CR G .

6. The boron-containing organic compound according to claim 4, wherein It has the structure shown in Formula IV: Among them, ring A, X1, Ar1, R1, and R2 have the same defined ranges as in formula I; R3, R4, R5, and R6 have the same defined ranges as in formula II; G is selected from any one of the structural formulas G1 - G8; Preferably, the connection position of G is the para position of the carbon atom connected to the B atom; Preferably, when G is selected from the structural formula G1, X 11 , X 12 , X 13 , X 14 , X 15 are each independently CR 20 ; R 20 are each independently selected from hydrogen, halogen, cyano, unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylsilyl, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

7. The boron-containing organic compound according to any one of claims 1-6, characterized in that, X1 is selected from CR 11 ; Preferably, the R 11 is selected from any one of hydrogen, halogen, cyano, unsubstituted or R”-substituted C1-C10 linear or branched alkyl, unsubstituted or R”-substituted C3-C10 cycloalkyl, unsubstituted or R”-substituted C6-C20 aryl, and unsubstituted or R”-substituted C3-C20 heteroaryl; more preferably hydrogen; Each of R1 and R2 is independently selected from hydrogen, unsubstituted or R''-substituted C1 - C20 straight-chain or branched-chain alkyl, unsubstituted or R''-substituted C3 - C20 cycloalkyl, unsubstituted or R''-substituted C6 - C60 aryl, unsubstituted or R''-substituted C3 - C60 heteroaryl, and R1 and R2 are not connected by a chemical bond to form a ring, and at least one of R1 and R2 is not hydrogen; each of R'' is independently selected from halogen, cyano, unsubstituted or R-substituted C1 - C20 straight-chain or branched-chain alkyl, unsubstituted or R-substituted C3 - C20 cycloalkyl, unsubstituted or R-substituted C6 - C60 aryl, unsubstituted or R-substituted C3 - C60 heteroaryl.

8. The boron-containing organic compound according to any one of claims 3-6, characterized in that, Any one of the adjacent two groups among R3, R4, R5, and R6 is connected by a chemical bond to form ring C, and the other groups except for forming ring C are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; ring C has the structure shown in formula C: The dotted line represents a fused bond; Y1, Y2, Y3, Y4 are each independently N or CR 22 ; R 22 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; adjacent R 22 are not connected or connected by a chemical bond to form a ring, and the R 22 is not connected to the adjacent ring structure or connected by a chemical bond to form a ring; M1 and M2 are each independently selected from a single bond, NR 14 , O, S or CR 15 R 16 wherein any one of them is selected, and M1 and M2 are not simultaneously a single bond; R 14 、R 15 、R 16 Each independently selected from any one or a combination of at least two of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, M1 is selected from NR 14 , O, S or CR 15 R 16 , and M2 is a single bond.

9. The boron-containing organic compound according to any one of claims 1-7, characterized in that, Ar1 has the structure shown in formula D: Wherein, * represents the connection site of the group; Q1, Q2, Q3, Q4, and Q5 are each independently N or CR 23 ; R 23 each independently selected from hydrogen, halogen, unsubstituted or R-substituted C1-C20 linear or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, unsubstituted or R-substituted C3-C60 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Each of R is independently selected from halogen, cyano, nitro, hydroxyl, amino, C1 - C20 straight-chain or branched-chain alkyl, C2 - C20 alkenyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, C1 - C20 alkylsilyl, C1 - C20 alkylamino, C6 - C60 arylsilyl, C3 - C60 heteroarylsilyl, C6 - C60 arylamino, C3 - C60 heteroarylamino, C6 - C30 aryloxy, C3 - C30 heteroaryloxy, C6 - C60 aryl, C3 - C60 heteroaryl, or a combination of any one or at least two of them, adjacent Rs are not connected or are connected by a chemical bond to form a ring, and R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Preferably, at most one of Q1, Q2, Q3, Q4, and Q5 is N; Preferably, Q1, Q2, Q3, Q4, and Q5 are each independently CR 23 ; More preferably, the R 23 is selected from any one of unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, and unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or are connected into a ring through a chemical bond; Each of R is independently selected from halogen, cyano, C1 - C20 straight-chain or branched-chain alkyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, C1 - C1 - C20 alkylamino, C6 - C60 arylamino, C3 - C60 heteroarylamino, C6 - C30 aryloxy, C3 - C30 heteroaryloxy, C6 - C60 aryl, C3 - C60 heteroaryl, adjacent Rs are not connected or are connected by a chemical bond to form a ring, and R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring.

10. The boron-containing organic compound according to claim 9, characterized in that, Selected from the structures represented by the following formula IV-1 or formula IV-2, M3 is selected from a single bond, NR 17 , O, S, Se, CR 18 R 19 or SiR 13 R 13 '; Preferably, it has the structure shown in formula IV - 2 as follows, More preferably, M3 in formula (2) is a single bond.

11. The boron-containing organic compound according to claim 10, wherein Selected from the structures shown in formula V - 1 to formula V - 4 as follows, Preferably, the M1 is selected from NR 14 , O, CR 15 R 16 ; more preferably, the M1 is NR 14 ; Preferably, X1 is CR 11 , and R 11 is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl, and more preferably hydrogen; Preferably, each of Y1, Y2, Y3, and Y4 is independently selected from CR 22 ; R 22 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of any one or at least two thereof; adjacent R 22 are not connected or are connected by a chemical bond to form a ring, and the R 22 is not connected or is connected by a chemical bond to an adjacent ring structure to form a ring. Preferably, the R 22 are each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; adjacent R 22 are not connected or are connected by a chemical bond to form a ring, and the R 22 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; more preferably, it is hydrogen; X2, X3, X4, and X5 are each independently selected from CR 21 ; Preferably, the R 21 each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C10 linear or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and more preferably hydrogen; Preferably, each of Q1, Q2, Q3, Q4, and Q5 is independently CR 23 ; More preferably, the R 23 is selected from any one of hydrogen, halogen, unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C1-C10 alkoxy, unsubstituted or R-substituted C1-C10 alkylamino, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C30 aryl, and unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Each R is independently selected from any one of halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Adjacent Rs are not connected or are connected by a chemical bond to form a ring. The R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring. Preferably, more preferably, the R 23 is selected from any one of hydrogen, halogen, unsubstituted or R-substituted C1-C10 linear or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C6-C30 aryl, and unsubstituted or R-substituted C3-C30 heteroaryl; the substituents of the substitution are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Each R is independently selected from any one of halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Adjacent Rs are not connected or are connected by a chemical bond to form a ring. The R is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring. More preferably, R 23 is hydrogen.

12. The boron-containing organic compound according to any one of claims 1-11, characterized in that, Each of R1 and R2 is independently selected from any one of unsubstituted or R''-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R''-substituted C6-C20 aryl, and unsubstituted or R''-substituted C3-C20 heteroaryl. Preferably, each of R1 and R2 is independently selected from substituted or unsubstituted C1-C6 straight-chain or branched-chain alkyl groups, any one of; represents the attachment site of the group; R X each independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl; n is an integer selected from 0 to 5. Preferably, at least one of R1 and R2 is selected from More preferably, R1 and R2 are each independently selected from Preferably, each of R1 and R2 is independently selected from any one of them.

13. The boron-containing organic compound according to claim 9, characterized in that, is selected from the structures shown in any one of the following formulas VI-1, VI-2, VI-3, and VI-4: wherein Y1, Y2, Y3, and Y4 have the same defined range as in formula C; M1 is selected from NR 14 , O, S or CR 15 R 16 ; any one of them Q1, Q2, Q3, Q4, and Q5 have the same defined range as in formula D; R7 is selected from hydrogen, halogen, unsubstituted or R''-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R''-substituted C3-C10 cycloalkyl, unsubstituted or R''-substituted C6-C20 aryl, and unsubstituted or R''-substituted C3-C20 heteroaryl. Each of R8 and R9 is independently selected from halogen, unsubstituted or R-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R-substituted C3-C20 cycloalkyl, unsubstituted or R-substituted C2-C20 alkenyl, unsubstituted or R-substituted C1-C20 alkoxy, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R-substituted C6-C30 arylsilyl, unsubstituted or R-substituted C6-C30 heteroarylsilyl, unsubstituted or R-substituted C6-C30 arylamino, unsubstituted or R-substituted C3-C30 heteroarylamino, unsubstituted or R-substituted C6-C30 aryloxy, unsubstituted or R-substituted C3-C30 heteroaryloxy, unsubstituted or R-substituted C6-C60 aryl, and unsubstituted or R-substituted C3-C60 heteroaryl. The substituents of the substitution are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring. Preferably, the connecting position of G is the para position of the carbon atom connected to the B atom. Preferably, G has the structure shown in any one of G1 - G5, and preferably has the structure shown in G1; Preferably, said X 11 、X 12 、X 13 、X 14 、X 15 are each independently selected from CR 20 ; Preferably, the number of CH in the said X 11 , X 12 , X 13 , X 14 and X 15 is 2 - 5, more preferably 3 - 4; Preferably, the R 20 each independently selected from hydrogen, cyano, halogen, unsubstituted or R-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R-substituted C3-C10 cycloalkyl, unsubstituted or R-substituted C2-C10 alkenyl, unsubstituted or R-substituted C1-C20 alkylsilyl, unsubstituted or R-substituted C6-C30 aryl, unsubstituted or R-substituted C3-C30 heteroaryl; Preferably, the R G is selected from any one of the following groups: * represents the linking site of the group; preferably, said R G is selected from any one of the following groups: Preferably, each of Y1, Y2, Y3, and Y4 is independently CR 22 ; More preferably, each of Y1, Y2, Y3, and Y4 is CH; Preferably, R7 is hydrogen; more preferably, R7, R8, and R9 are all hydrogen.

14. The boron-containing organic compound according to claim 1, wherein Has the following structure:

15. Use of the organic compound according to any one of claims 1 to 14, wherein the use is as a functional material in an organic electronic device, and the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin - film transistor, an organic field - effect transistor, an information tag, an electronic artificial skin sheet, a sheet - type scanner, or an electronic paper; Preferably, the use of the organic compound is as a light - emitting layer material in an organic electroluminescent device, and more preferably as a light - emitting dye in the light - emitting layer.

16. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light - emitting functional layers inserted between the first electrode and the second electrode, wherein the light - emitting functional layer contains the organic compound according to any one of claims 1 to 14; Preferably, the light - emitting functional layer includes an electron - blocking layer and at least one of a hole - injection layer, a hole - transport layer, a light - emitting layer, and an electron - transport layer, and the light - emitting layer contains the organic compound according to any one of claims 1 to 14; More preferably, the light - emitting functional layer includes an electron - blocking layer and at least one of a hole - injection layer, a hole - transport layer, a light - emitting layer, and an electron - transport layer, the light - emitting layer includes a host material and a dye, and the dye includes at least one organic compound according to any one of claims 1 to 14.

17. A display device, characterized in that, The display device includes the organic electroluminescent device according to claim 16.

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