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. Through design and mutual compounding of a specific fused ring skeleton structure and groups, the boron-containing organic compound has excellent photoelectric properties and narrow spectrum characteristics. The boron-containing organic compound is used for the organic electroluminescent device and can be used as a fluorescent doping material of a light-emitting layer, so that the device has high color purity, the efficiency roll-off of the device can be inhibited, the light-emitting efficiency of the device is improved, the service life is prolonged, the voltage and the energy consumption are reduced, and the requirements of a current display device and a current panel on a high-performance material are fully met.

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] In recent years, electroluminescent devices based on organic materials (such as organic light-emitting diodes, OLEDs) have become increasingly popular. Compared with electroluminescent devices based on inorganic materials, the inherent flexibility of organic materials makes them very suitable for manufacturing flexible and thin electroluminescent devices, and beautiful and cool screens, displays, lighting devices, etc. can be designed and produced according to requirements, having advantages unparalleled by inorganic materials. Currently, OLED-based screens and displays already have good efficiency and lifespan, but OLED devices with long lifespan, high efficiency, and high color purity are still difficult points in research and development.

[0003] With the rapid development of information technology, display technology faces higher requirements, such as meeting the color gamut standard BT-2020 of image signals in the 4K and 8K eras, where the CIEy of green light is 0.797, significantly increasing the color gamut coverage. Currently, using luminescent materials with narrow full-width at half-maximum emission spectra is one of the important means to achieve high color purity. Especially among currently commercialized OLED materials, green light-emitting materials use phosphorescent materials with relatively wide full-width at half-maximum and strong shoulders at long wavelengths, and it is difficult to simultaneously meet the requirements of high efficiency and excellent color purity. In recent years, scientists have developed thermally activated delayed fluorescence materials (TADF) that not only have 100% theoretically exciton utilization efficiency but also have narrow emission spectra. Using them as OLED luminescent materials is expected to meet the high color purity requirements of BT-2020 and can also ensure relatively high efficiency. However, the efficiency roll-off of such materials is serious at high brightness, and the device lifespan is short, far from meeting the standards for mass production and use. To solve this problem, scientists have proposed a strategy of super fluorescence, that is, through energy transfer, the excited state energy of TADF materials or phosphorescent materials is transferred to narrow-spectrum fluorescent materials for luminescence, thereby achieving both 100% theoretically exciton utilization efficiency and obtaining narrow emission spectra, and it is expected to obtain OLED devices with good efficiency, long lifespan, and high color purity. In addition, phosphorescent materials are usually based on transition metals, such as iridium, platinum, etc. Due to their usually low abundance, they are very expensive among many OLED materials. Therefore, reducing the usage amount of phosphorescent materials is crucial for reducing the cost of OLEDs.

[0004] Therefore, developing more types of organic narrow-spectrum luminescent materials with better electroluminescent performance is one of the key issues to achieve the above expectations and is the research focus in this field. Summary of the Invention

[0005] In view of 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 used in an organic electroluminescent device, it can effectively improve the luminous efficiency of the device, reduce the operating voltage, and comprehensively improve the luminous performance of the device.

[0006] To achieve this purpose, the present invention adopts the following technical solutions:

[0007] In the first aspect, the present invention provides a boron-containing organic compound having a structure shown in Formula I:

[0008]

[0009] In Formula I, ring A is selected from any one of substituted or unsubstituted C6-C60 aromatic rings.

[0010] In Formula I, Ar 1 is selected from any one of substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups; the Ar 1 is not connected to the adjacent ring structure or is connected into a ring through a chemical bond.

[0011] In the present invention, "Ar 1 is not connected to the adjacent ring structure" means that Ar 1 is only connected to the N atom through a single bond; "Ar 1 is connected to the adjacent ring structure through a chemical bond to form a ring" means that Ar 1 , in addition to being connected to the N atom through a chemical bond, is also connected to the adjacent ring (such as the benzene ring where R 6 is located) through a chemical bond, thereby forming a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0012] In Formula I, X 1 is selected from CR 11 or N.

[0013] In Formula I, Z 1 , Z 2 , Z 3 are each independently selected from CR 12 or N; the R 12 in multiple (such as 2, 3) CR 12 are the same or different groups.

[0014] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 11 , R12 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 heteroarylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 1 and R 2 are not connected by a chemical bond; said R 11 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; adjacent R 12 are not connected or are connected by a chemical bond to form a ring, and said R 12 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring.

[0015] Said R 1 and R 2 At least one of them is selected from substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.

[0016] Ring A, Ar 1 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 11 、R 12The substituents in the [description] are each 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 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 are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0017] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different substituents; when the same expression is involved hereinafter, it shall have the same meaning. Unless otherwise specified, the selection range of the substituents is as shown above and will not be elaborated further.

[0018] The R 3 、R 4 、R 5 、R 6 Among them, one group of any two adjacent groups is connected into ring B through a chemical bond, and the other groups except those forming ring B are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0019] Ring B has a structure as shown in formula a:

[0020]

[0021] In formula a, the dotted line represents the fused bond of ring B.

[0022] In formula a, Y 1 、Y 2 、Y 3 、Y 4 are each independently selected from N or CR 13 ; R 13 in multiple (such as 2, 3, 4) CR 13 are the same or different groups.

[0023] R 13Each independently selected from hydrogen, 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 C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, 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 R 13 Each is independently not connected to the adjacent ring structure or connected by a chemical bond to form a ring.

[0024] In formula a, M 1 and M 2 Each independently selected from a single bond, NR 14 , O, S, Se, CR 15 R 16 or SiR 17 R 18 , and at most one of the M 1 and M 2 is a single bond. Among them, when one of M 1 and M 2 is a single bond, the ring B shown in formula a can be understood as a structure in which a six-membered ring (such as a benzene ring) is fused with a five-membered ring (such as a pyrrole ring, a furan ring, a thiophene ring, cyclopentadiene); when neither M 1 nor M 2 is a single bond, the ring B shown in formula a can be understood as a structure formed by the fusion of two six-membered rings.

[0025] R 14 , R 15 , R 16 , R 17 , R 18 Each independently selected from 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 C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; the R 15 and R 16 are not connected or connected by a chemical bond to form a ring; the R 17 and R 18 are not connected or connected by a chemical bond to form a ring.

[0026] Each R' independently represents any one or a combination of at least two 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-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C60 heteroaryl; adjacent R's are not connected or are connected by a chemical bond to form a ring, and the R' is not connected or is connected by a chemical bond to the adjacent ring structure to form a ring.

[0027] In the present invention, the group of "unsubstituted or R'-substituted" may be substituted with one substituent R' or may be substituted with multiple substituents R'. When there are multiple (at least 2) substituents R', they may be the same or different substituents; when the same expression is involved hereinafter, it has the same meaning. Unless otherwise specified, the selection range of R' is as shown above and will not be elaborated further.

[0028] The molecular structure of the boron-containing organic compound provided by the present invention is shown in Formula I and has the following structural features and technical effects: (1) The molecular skeleton contains a B-N structure. The boron atom and the nitrogen atom in the same ring have a resonance effect and have a strong central rigid structure, which is beneficial to reducing the Stokes shift of the molecule, making the boron-containing organic compound have the characteristics of narrow spectral emission and high color purity, and is beneficial to improving the luminescence efficiency in the device; (2) A fused ring structure shown in Formula a is introduced on one side of the B-N skeleton structure, which is beneficial to restricting the structural relaxation of the molecule in the excited state, further 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 improving the device efficiency; (3) A benzindole fused structure is introduced on the other side of the B-N skeleton structure, which is beneficial to reducing the T 1 energy level and suppressing stability problems (such as TTA, TPA, etc. in the device) caused by the high-energy T 1 energy level of the molecule, which is beneficial to improving the lifetime of the device. In addition, such groups have good molecular planarity, which is beneficial to improving the molecular carrier transport ability and reducing the device voltage. R 1 and R 2 groups can also play a certain role in adjusting the molecular energy level and molecular steric hindrance, which is beneficial to improving the device efficiency.

[0029] Through the design, mutual compounding and synergistic effect of the fused-ring skeleton and groups, the boron-containing organic compound of the present invention has excellent optoelectronic properties and narrow spectral characteristics. When used as a fluorescent doping material (fluorescent dye) for the light-emitting layer, the device has high color purity, can suppress the efficiency roll-off of the device, improve the light-emitting efficiency and lifespan, and reduce the operating voltage and energy consumption. In addition, the preparation process of the boron-containing organic compound 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.

[0030] It should be noted that in the present invention, 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 essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect between various groups, rather than the effect of a single group / feature.

[0031] The following are the preferred technical solutions of the present invention, but do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved.

[0032] In the present invention, the halogens can all be fluorine, chlorine, bromine or iodine. The same description involved below has the same meaning.

[0033] In the present invention, for the expression of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0034] In the present invention, unless otherwise specified, the heteroatoms of the heteroaryl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0035] In the present invention, the expression of the ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure where bonding can occur.

[0036] In the present invention, both "-*" and "*" represent the connection sites of the groups.

[0037] In the present invention, the expression Ca-Cb represents that the group has a carbon atom number of a-b. Unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0038] In the present invention, "independently of each other" means that when the subject has multiple ones, they can be the same or different from each other.

[0039] In the present invention, the C6-C60 can all 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.

[0040] The C3-C60 can all 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.

[0041] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0042] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0043] The C2-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0044] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0045] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0046] In the present invention, the C6-C60 aryl group, preferably the C6-C30 aryl group, more preferably the C6-C20 aryl group, includes monocyclic aryl groups and polycyclic aryl groups; the monocyclic aryl group means a group containing at least 1 phenyl group, and when containing at least 2 phenyl groups, the phenyl groups are connected by single bonds. Exemplarily, it includes but is not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the polycyclic aryl group means a group containing at least 2 aromatic rings, and the aromatic rings are fused to each other by sharing two adjacent carbon atoms. Exemplarily, it includes but is not limited to: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, -yl, tetraphenylenyl, acenaphthylenyl, benzoacenaphthylenyl, etc. It should be noted that monocyclic aryl groups and polycyclic aryl groups connected by single bonds also belong to the scope of aryl groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0047] The C3-C60 heteroaryl group, preferably the C6-C30 heteroaryl group, more preferably the C3-C20 heteroaryl group, includes monocyclic heteroaryl groups or polycyclic heteroaryl groups. The monocyclic heteroaryl group means a molecule containing at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl groups, heteroaryl groups, etc.), the heteroaryl group and other groups are connected by single bonds. Exemplarily, it includes but is not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The polycyclic heteroaryl group means a molecule containing at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aromatic ring), and the two are fused to each other by sharing two adjacent atoms. Exemplarily, it includes but is not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl groups connected by single bonds and heteroaryl groups, aryl groups and heteroaryl groups connected by single bonds also belong to the scope of heteroaryl groups, such as phenylpyridyl, phenylpyrimidinyl, diphenylpyridyl, diphenylpyrimidinyl, etc.

[0048] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl group with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl group with O.

[0049] In the present invention, a specific example of the C6-C60 arylamino group and the C6-C30 arylamino group is -NH 2 The monovalent group obtained by replacing at least one hydrogen in the group with the above-mentioned aryl group includes, but is not limited to, phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino and C3-C30 heteroarylamino are -NH 2 The monovalent group in which at least one hydrogen in the amino group is replaced by the above-mentioned heteroaryl group includes, but is not limited to, pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.

[0050] A specific example of the C6-C30 aryl silicon group is -SiH 3 A monovalent group obtained by replacing at least one hydrogen in the group with the above-mentioned aryl group. A specific example of the C6-C30 heteroarylsilyl group is -SiH 3 A monovalent group obtained by replacing at least one hydrogen atom in the cyclopentane group with the above-mentioned heteroaryl group.

[0051] The C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, and further preferably a C1-C10 straight chain or branched alkyl group, illustratively includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0052] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0053] A specific example of the C1-C20 alkylsilyl group is -SiH 3 A monovalent group obtained by replacing at least one hydrogen in the group with the straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is -NH 2 A monovalent group obtained by replacing at least one hydrogen atom in the alkyl group with the above-mentioned straight-chain or branched-chain alkyl group.

[0054] The C3-C20 cycloalkyl, preferably C3-C10 cycloalkyl, includes monocycloalkyl or polycycloalkyl. Monocycloalkyl refers to an alkyl group containing a single cyclic structure, and polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; exemplary examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0055] The C2-C20 alkenyl group, preferably a C2-C10 alkenyl group, which contains at least one C═C, exemplarily includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0056] Preferably, the ring A is The dotted line represents the fused bond of ring A.

[0057] Preferably, the boron-containing organic compound has the structure shown in Formula II:

[0058]

[0059] In Formula II, Ar 1 , X 1 , Z 1 , Z 2 , Z 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Have the same defined range as in Formula I.

[0060] X 2 , X 3 , X 4 , X 5 Each independently selected from CR 21 or N; multiple (such as 2, 3, 4) CR 21 in which the R 21 are the same or different groups.

[0061] R 21 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, unsubstituted or R'-substituted C3-C60 heteroaryl; the R 21Each is independently unconnected to an adjacent ring structure or connected into a ring through a chemical bond.

[0062] Preferably, the Ar 1 is -* represents the connection site of Ar 1

[0063] Preferably, the boron-containing organic compound has a structure shown in Formula III-1:

[0064]

[0065] In Formula III-1, X 1 , X 2 , X 3 , X 4 , X 5 , Z 1 , Z 2 , Z 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 have the same defined range as in Formula II.

[0066] In Formula III-1, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 are each independently selected from CR 31 or N; the R 31 in a plurality (e.g., 2, 3, 4, 5) of CR 31 are the same or different groups.

[0067] R 31 ​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 R 31 Each is independently not connected to the adjacent ring structure or connected into a ring through a chemical bond.

[0068] Preferably, the Q 5 is CR 31 and the R in Q 5 is connected into a ring with the adjacent ring structure through a chemical bond. 31

[0069] Preferably, the boron-containing organic compound has the structure shown in Formula III-2:

[0070]

[0071]

[0071] wherein X 1 X 2 X 3 X 4 X 5 Z 1 Z 2 Z 3 R 1 R 2 R 3 R 4 R 5 Q 1 Q 2 Q 3 Q 4 has the same defined range as in Formula III-1.

[0072] Preferably, in Formula a, the M 1 is selected from any one of O, S, NR 14 O, S, Se, CR 15 R 16 or SiR 17 R 18 and the M2 is a single bond, whereby the ring B is

[0073] Preferably, the boron-containing organic compound has a structure represented by any one of Formula IV-1, Formula IV-2, Formula IV-3, and Formula IV-4:

[0074]

[0075] wherein X 1 , X 2 , X 3 , X 4 , X 5 , Z 1 , Z 2 , Z 3 , R 1 , R 2 , R 3 , R 5 , Q 1 , Q 2 , Q 3 , Q 4 has the same defined range as Formula III-1; Y 1 , Y 2 , Y 3 , Y 4 has the same defined range as Formula a.

[0076] M 1 is selected from any one of NR 14 , O, S, CR 15 R 16 or SiR 17 R 18 .

[0077] R 14 , R 15 , R 16 , R 17 , R 18 are each independently selected from 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 C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; there is no connection or a chemical bond connection to form a ring between the R 15 and R 16 ; there is no connection or a chemical bond connection to form a ring between the R 17 and R 18 .

[0078] Preferably, the M 1 is selected from NR14 , O, CR 15 R 16 Any one of, more preferably NR 14 .

[0079] Preferably, the boron-containing organic compound has a structure as shown in Formula IV-1 or Formula IV-2.

[0080] Preferably, the Z 1 , Z 2 and Z 3 At least one of them is CR 12 , at least one of the R 12 For the group R G , the R G Having any of the following structures G1-G8:

[0081]

[0082]

[0083] -* represents the attachment site of the group.

[0084] X 11 , X 12 , X 13 , X 14 , X 15 Each independently selected from N or CR 20 ; Multiple (e.g. 2, 3, 4, 5) CR 20 R 20 are the same or different groups.

[0085] R 20 each independently selected from hydrogen, halogen, 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, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6- any one of C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, 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; the adjacent R 20 are not connected or connected to form a ring through chemical bonds, the R 20It is not connected to an adjacent ring structure or is connected into a ring through a chemical bond.

[0086] R A1 and R A2 each independently represent unsubstituted, mono-substituted to the maximum allowable substitution.

[0087] Among them, R A1 represents unsubstituted (R A1 is hydrogen), mono-substituted, di-substituted, tri-substituted, tetra-substituted or penta-substituted; when R A1 represents di-substituted or tri-substituted, multiple R A1 are the same or different groups; the description of R A2 is the same, for the sake of brevity, it will not be elaborated here.

[0088] R A1 and R A2 each independently selected from any one or a combination of at least two of hydrogen, 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-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C60 heteroaryl.

[0089] As a preferred technical solution of the present invention, a class of sterically hindered groups R G are introduced into the molecular structure of the boron-containing organic compound, and R G as a steric hindrance group can effectively improve the quenching and adverse effects caused by molecular aggregation, inhibit the efficiency roll-off of organic electroluminescent devices, and is beneficial to the improvement of device efficiency.

[0090] Preferably, the Z 1 , Z 2 , Z 3 each independently selected from CR 12 , and at least one of the R 12 is the group R G .

[0091] Preferably, the Z 1 , Z 2 , Z 3 each independently selected from CH or CR G , and one of them is CR G .

[0092] Preferably, the Z 1 and Z 3 are CH, and the Z 2is CR G ; that is, the R G is connected to the para-position of the carbon atom connected to the B atom.

[0093] Preferably, the X 1 is CR 11 .

[0094] Preferably, the R 11 is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably hydrogen, that is, X 1 is preferably CH.

[0095] Preferably, at most 1 (0 or 1) of the Y 1 , Y 2 , Y 3 and Y 4 is N.

[0096] Preferably, the Y 1 , Y 2 , Y 3 , Y 4 are each independently selected from CR 13 .

[0097] Preferably, the R 13 are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, unsubstituted or R'-substituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably hydrogen.

[0098] Preferably, the X 2 , X 3 , X 4 and X 5At most one (0 or 1) of them is N.

[0099] Preferably, the X 2 and X 3 and X 4 and X 5 are each independently selected from CR 21 .

[0100] Preferably, the R 21 are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, unsubstituted or R'-substituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably hydrogen.

[0101] Preferably, at most one (0 or 1) of the Q 1 and Q 2 and Q 3 and Q 4 is N.

[0102] Preferably, the Q 1 and Q 2 and Q 3 and Q 4 are each independently selected from CR 31 .

[0103] Preferably, the R 31 are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, unsubstituted or R'-substituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably hydrogen.

[0104] Preferably, the boron-containing organic compound has a structure shown in any one of Formula V-1, Formula V-2, Formula V-3, and Formula V-4:

[0105]

[0106] Among them, R 1 and R 2 have the same defined range as formula I; R G has any one of the structures G1-G8.

[0107] M 1 is selected from any one of NR 14 , O, S or CR 15 R 16 ;

[0108] R 14 , R 15 , and R 16 are each independently selected from 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 C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R 15 and R 16 are either not connected or connected by a chemical bond to form a ring.

[0109] Preferably, R 14 is selected from unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, more preferably unsubstituted or R'-substituted phenyl.

[0110] Preferably, R' in R 14 is selected from any one of C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, more preferably any one of methyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, phenyl, biphenyl, naphthyl.

[0111] Preferably, R 15 , R 16Each independently selected from unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl groups, unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl groups, and more preferably methyl or phenyl.

[0112] R 13 、R 21 、R 31 Each independently represents unsubstituted, mono-substituted to the maximum allowable substitution; wherein, R 13 represents unsubstituted (R 13 is hydrogen), mono-substituted, di-substituted, tri-substituted or tetra-substituted; when R 13 represents di-substituted, tri-substituted or tetra-substituted, multiple R 13 are the same or different groups; the same applies to R 21 、R 31 , for the sake of brevity, will not be elaborated further.

[0113] R 13 、R 21 、R 31 Each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched-chain alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, cyano groups, nitro groups, hydroxyl groups, amino groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, unsubstituted or R'-substituted C6-C30 arylamino groups, unsubstituted or R'-substituted C3-C30 heteroarylamino groups, unsubstituted or R'-substituted C6-C30 aryloxy groups, unsubstituted or R'-substituted C3-C30 heteroaryloxy groups, unsubstituted or R'-substituted C6-C60 aryl groups, unsubstituted or R'-substituted C3-C60 heteroaryl groups.

[0114] Preferably, the boron-containing organic compound has a structure shown in Formula V-1 or Formula V-2.

[0115] Preferably, the R G is connected to the para-position of the carbon atom to which the B atom is attached.

[0116] Preferably, the R 1 、R 2Each independently selected from a substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl group, a substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group.

[0117] Preferably, the R 1 , R 2 Each independently selected from a substituted or unsubstituted C1-C6 straight-chain or branched-chain alkyl group, Any one of them; -* represents the connection site of the group.

[0118] R X Each independently selected from 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 C6-C30 aryl group, an unsubstituted or R'-substituted C3-C30 heteroaryl group, more preferably an unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl group, an unsubstituted or R'-substituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl group, an unsubstituted or R'-substituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, an unsubstituted or R'-substituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group, and even more preferably any one of methyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, phenyl or biphenyl.

[0119] n represents the number of substituents R X , selected from integers from 0 to 5, for example, it can be 0, 1, 2, 3, 4 or 5; when n≥2, multiple R X Are the same or different groups.

[0120] Exemplarily, the R 1 , R 2 Each independently selected from methyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, Any one of them.

[0121] Preferably, at least one of the R 1 and R 2 Is selected from More preferably R1 and R 2 are each independently

[0122] Preferably, the said R 1 and R 2 are each independently selected from methyl, any one of the following.

[0123] Preferably, at least one of the said R 1 and R 2 is selected from any one of Further preferably, the said R 1 and R 2 are each independently selected from any one of the following.

[0124] Preferably, the said R G has the structure shown in any one of G1 - G5, and more preferably has the structure shown in G1.

[0125] Preferably, the said X 11 and X 12 and X 13 and X 14 and X 15 are each independently selected from CR 20 .

[0126] Preferably, the number of CH in the said X 11 and X 12 and X 13 and X 14 and X 15 is 2 - 5, and more preferably 3 - 4.

[0127] Preferably, the said R 20Each independently selected from hydrogen, cyano, halogen, unsubstituted or R'-substituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, unsubstituted or R'-substituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, unsubstituted or R'-substituted C1-C20 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C14, C15, C16 or C18, etc.) alkylsilyl, unsubstituted or R'-substituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl, unsubstituted or R'-substituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryl, and further preferably any one of hydrogen, cyano, fluorine, C1-C6 straight-chain or branched-chain alkyl, C3-C10 cycloalkyl, C1-C10 alkylsilyl, C6-C18 aryl, C6-C18 heteroaryl, and even more preferably any one of hydrogen, cyano, fluorine, methyl, trifluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, trimethylsilyl, phenyl, biphenyl, naphthyl, carbazolyl, pyridyl, dibenzofuranyl, dibenzothiophenyl.

[0128] Preferably, R 20 wherein the R' is selected from cyano, halogen, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, and further preferably any one of cyano, fluorine, methyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, trimethylsilyl, phenyl, biphenyl, naphthyl.

[0129] Preferably, the R 20 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring Cy 1 and the ring Cy1 Selected from any one of substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclics, substituted or unsubstituted C4-C20 (such as C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroalicyclics, substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic rings, substituted or unsubstituted C3-C20 (such as C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic rings, and further preferably The dashed line represents the ring Cy 1 The fusion site.

[0130] Preferably, the R G Is selected from any one of the following groups:

[0131] -* represents the connection site of the group.

[0132] Preferably, the R G Is selected from Any one of them.

[0133] Preferably, the boron-containing organic compound has a structure shown in any one of M1-M242 as follows:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] 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.

[0148] 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.

[0149] Preferably, the boron-containing organic compound is applied to an organic electroluminescent device.

[0150] Preferably, the boron-containing organic compound serves as a light-emitting layer material in the organic electroluminescent device.

[0151] Preferably, the boron-containing organic compound serves as a dye (also referred to as "doping material", "dopant", "guest material") of the light-emitting layer in the organic electroluminescent device.

[0152] 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; at least one boron-containing organic compound as described in the first aspect is included in the organic layer.

[0153] Preferably, at least one boron-containing organic compound having a structure shown by M1-M242 is included in the organic layer.

[0154] Preferably, the organic layer includes a light-emitting layer, and at least one boron-containing organic compound as described in the first aspect is included in the light-emitting layer, and more preferably at least one boron-containing organic compound having a structure shown by M1-M242 is included.

[0155] Preferably, the light-emitting layer includes a host material and a doping material, and the doping material includes at least one boron-containing organic compound as described in the first aspect.

[0156] Preferably, the compound provided by the present invention serves as a fluorescent doping material (fluorescent dye) of the light-emitting layer.

[0157] Preferably, the mass percentage content of the doping 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., and more preferably 0.3-3%.

[0158] 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.

[0159] Preferably, the light-emitting layer further includes a sensitizer.

[0160] Preferably, the sensitizer includes any one or a combination of at least two of a thermally activated delayed fluorescence material and a phosphorescent material.

[0161] 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.

[0162] 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%.

[0163] 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%.

[0164] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0165] 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.

[0166] 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.

[0167] 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. This organic layer can be further divided into multiple regions, for example, including 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 more preferably contains at least one boron-containing organic compound with the structure shown in M1-M242.

[0168] 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 disposed 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 disposed 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 more preferably contains at least one boron-containing organic compound having the structure shown in M1-M242.

[0169] In a preferred technical solution, a substrate can be used under the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, thin film transistors (TFTs) can also be provided on the substrate for use as a display.

[0170] 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 (SnO 2 ) and zinc oxide (ZnO), 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), and magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0171] 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.

[0172] 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.

[0173] 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.

[0174]

[0175]

[0176]

[0177]

[0178] 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 be one or more of the compounds of HT-1 to HT-51 above, or one or more of the compounds of HI-1 to HI-3 below; it can also be one or more of the compounds of HT-1 to HT-51 doped with one or more of the compounds of HI-1 to HI-3.

[0179]

[0180] The light-emitting layer includes a light-emitting dye (i.e., a doping material, dopant) and a host material that can emit light spectra of different wavelengths. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color such as red, green, or blue. Multiple monochromatic 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 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.

[0181] According to different technologies, the light-emitting layer material can be different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, etc. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0182] In one aspect of the present invention, the host material of the light-emitting layer is selected from, but not limited to, one or a combination of more than one of PH-1 to PH-85.

[0183]

[0184]

[0185]

[0186]

[0187] In one aspect of the present invention, the light-emitting layer employs the technology of thermally activated sensitized fluorescence emission. The sensitizer of the light-emitting layer, i.e., the thermally activated delayed fluorescence material, can be selected from, but not limited to, one or a combination of more than one of the following listed TDE1-TDE37.

[0188]

[0189]

[0190]

[0191] In one aspect of the present invention, the light-emitting layer employs the technology of phosphorescent sensitized fluorescence electroluminescence, and the sensitizer phosphorescent material 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.

[0192]

[0193]

[0194] Where D is deuterium.

[0195] 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 the above HT-1 to HT-51, or can be made of, but not limited to, one or more compounds of the above PH-47 to PH-77; 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.

[0196] The OLED organic layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can 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 can 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).

[0197] 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.

[0198]

[0199]

[0200]

[0201]

[0202] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be made of, but not limited to, one or more compounds of the above-mentioned ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; it may also be a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0203] The device may further include an electron injection layer between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Yb.

[0204] In a fourth aspect, the present invention provides a display device, which includes the organic electroluminescent device as described in the third aspect.

[0205] Preferably, the display device includes a display screen or a display panel.

[0206] The present invention also provides an electronic device, which includes the aforementioned display device.

[0207] Compared with the prior art, the present invention has the following beneficial effects:

[0208] In the boron-containing organic compound provided by the present invention, through the design and mutual compounding of a specific polycyclic 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 the 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. Detailed embodiments

[0209] The technical solution of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0210] The boron-containing organic compound shown in Formula I of the present invention can be synthesized by organic synthesis methods known in the art. The following gives exemplary synthetic routes, but those skilled in the art can also obtain it by other known methods.

[0211] In a specific embodiment, the boron-containing organic compound has the structure shown in Formula I, wherein Z 1 、Z 2 、Z 3 are each independently selected from CH or CR G , and one of them is CR G , and can be prepared through the synthetic route shown below:

[0212]

[0213] Among them, ring A, Ar 1 、X 1 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 have the same defined ranges as in Formula I; Hal 1 、Hal 2 、Hal 3 are each independently selected from any one of F, I, Br or Cl; U 1 is selected from The order of Reaction I and Reaction II can be adjusted according to the synthesis situation, that is, Reaction I can be carried out first and then Reaction II, or Reaction II can be carried out first and then Reaction I. Reaction I, Reaction II and Reaction III are carried out in the presence of a palladium catalyst; Reaction IV is carried out in the presence of N,N-diisopropylethylamine and n-butyllithium (n-BuLi) or tert-butyllithium (t-BuLi).

[0214] The following will take multiple synthesis examples as an example to detail the specific preparation method of the boron-containing organic compound of the present invention, but the preparation method of the present invention is not limited to these synthesis examples.

[0215] It should be noted that the acquisition of the boron-containing organic 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 boron-containing organic compound proposed in the present invention. Compounds, solvents, and reagents of synthesis methods not mentioned in the present invention are all raw material products obtained through commercial channels, which can be purchased from the domestic chemical product market or prepared by oneself according to well-known methods based on these raw material products.

[0216] In the following synthesis examples of the present invention, the analysis and detection of intermediates and target products use a high-resolution mass spectrometer and adopt matrix-assisted laser desorption ionization (MALDI) technology.

[0217] Synthesis Example 1: Synthesis of Boron-Containing Organic Compound M1

[0218]

[0219] (1) Synthesis of Intermediate M1-1:

[0220] Put SM2 (22.5 g, 70.35 mmol) and N,N-dimethylformamide DMF (220 mL) into a 500 mL three-necked flask, displace with nitrogen three times, stir and cool down to 0 °C, and add sodium hydride (2.81 g, 70.35 mmol) to it in batches. After the addition is completed, react at 0 °C for 1 h and record it as A. Put SM1 (16 g, 70.35 mmol) and DMF (160 mL) into another 500 mL three-necked flask, displace with nitrogen three times. Cool down to 0 °C, and drip A into the system. After the dripping is completed, react at 0 °C for 5 h. Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and purify it by column chromatography to obtain 14.8 g of white solid of intermediate M1-1.

[0221] (2) Synthesis of Intermediate M1-2:

[0222] Put M1-1 (11 g, 20.88 mmol), SM3 (6.9 g, 20.88 mmol), cesium carbonate (20.41 g, 62.64 mmol), and DMF (110 mL) into a 250 mL single-necked flask, displace with nitrogen three times, and heat up to 100 °C for reaction overnight. Pour the reaction solution into water for quenching, filter, collect the solid and dry it, and recrystallize it with toluene / ethanol to obtain 15.2 g of white solid of intermediate M1-2.

[0223] (3) Synthesis of Intermediate M1-3:

[0224] Put intermediate M1-2 (9 g, 10.72 mmol), SM4 (2.76 g, 11.8 mmol), tetrakis(triphenylphosphine)palladium Pd(PPh 3 ) 4(248 mg, 0.21 mmol), potassium carbonate (2.2 g, 16 mmol), dioxane (90 mL), and water (30 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to reflux for overnight reaction. The reaction solution was concentrated under reduced pressure to remove dioxane. Water was added to the remaining residue and filtered. The collected solid was dried, purified by flash column chromatography using dichloromethane, concentrated to dryness, and recrystallized from toluene / ethanol to obtain 38.6 g of intermediate M1 as a white solid.

[0225] (4) Synthesis of target product M1:

[0226] Intermediate M1-3 (8 g) was added to a 250 mL three-necked flask, and xylene (80 mL) was added. The flask was purged with nitrogen three times, and the reaction system was cooled to -40 °C. tert-Butyllithium (13.18 mL) was added dropwise to the system, and then the temperature was raised to 60 °C for 2.5 h. The temperature of the reaction system was cooled to -40 °C, boron tribromide (2.44 mL) was added, and then the temperature was raised to 60 °C for 1.5 h. The temperature of the system was cooled to -40 °C again, and N,N-diisopropylethylamine (7 mL) was added. Finally, the reaction system was heated to 130 °C for 12 h. After the reaction cooled to room temperature, methanol (180 mL) was added dropwise to the system. After filtration and drying, recrystallization from ortho-dichlorobenzene / ethanol was carried out to obtain 2.5 g of an orange-red solid, which was the target product M1. The molecular ion mass determined by mass spectrometry: 921.56 (theoretical value: 921.43).

[0227] Synthesis Example 2: Synthesis of boron-containing organic compound M14

[0228]

[0229]

[0230] (1) Synthesis of intermediate M14-1:

[0231] The synthesis procedure was the same as that of M1-1, and intermediate M14-1 (13.6 g) as a white solid was obtained by column chromatography purification.

[0232] (2) Synthesis of intermediate M14-2:

[0233] M14-1 (11.5 g), SM3 (7.26 g), cesium carbonate (21.34 g), and DMF (115 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to 100 °C for overnight reaction. The reaction solution was quenched by pouring it into water, filtered, and the collected solid was dried. Recrystallization from toluene / ethanol gave 14.5 g of intermediate M14-2 as a white solid.

[0234] (3) Synthesis of intermediate M14-3:

[0235] Intermediate M14-2 (10 g), SM4 (5.14 g), Pd(PPh 3 ) 4 (275.4 mg), potassium carbonate (2.47 g), dioxane (100 mL), and water (30 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to reflux for overnight reaction. The reaction solution was concentrated under reduced pressure to remove dioxane. Water was added to the remaining residue and filtered. The collected solid was dried, purified by flash column chromatography using dichloromethane, concentrated to dryness, and recrystallized from toluene / ethanol to obtain 9.5 g of white solid intermediate M14-3.

[0236] (4) Synthesis of the target product M14:

[0237] The synthesis procedure was the same as that for M1. The product was recrystallized from o-dichlorobenzene / ethanol to obtain 2.7 g of orange-red solid, which was the target product M14. The molecular ion mass determined by mass spectrometry: 997.66 (theoretical value: 997.46).

[0238] Synthesis Example 3: Synthesis of the boron-containing organic compound M27

[0239]

[0240]

[0241] (1) Synthesis of intermediate M27-1:

[0242] The synthesis procedure was the same as that for M1-1. The intermediate M27-1 was purified by column chromatography to obtain 13.2 g of white solid.

[0243] (2) Synthesis of intermediate M27-2:

[0244] M27-1 (10 g), SM3 (4.88 g), cesium carbonate (18.55 g), and DMF (100 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to 100 °C for overnight reaction. The reaction solution was quenched by pouring it into water, filtered, and the collected solid was dried. The solid was recrystallized from toluene / ethanol to obtain 12.5 g of white solid intermediate M27-2.

[0245] (3) Synthesis of intermediate M27-3:

[0246] Intermediate M27-2 (10 g), SM4 (2.12 g), Pd(PPh 3 ) 4(302.5 mg), potassium carbonate (2.71 g), dioxane (100 mL), and water (30 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to reflux for overnight reaction. The reaction solution was concentrated under reduced pressure to remove dioxane. Water was added to the remaining residue and filtered. The collected solid was dried, passed through a flash column with dichloromethane, concentrated to dryness, and recrystallized from toluene / ethanol to obtain 9.3 g of intermediate M27-3 as a white solid.

[0247] (4) Synthesis of the target product M27:

[0248] The synthesis procedure was the same as that for M1. Recrystallization from o-dichlorobenzene / ethanol gave 2.3 g of an orange-red solid, which was the target product M27. The molecular ion mass determined by mass spectrometry: 759.36 (theoretical value: 759.25).

[0249] Synthesis Example 4: Synthesis of the boron-containing organic compound M44:

[0250]

[0251]

[0252] (1) Synthesis of intermediate M44-1:

[0253] The synthesis procedure was the same as that for M1-1. Purification by column chromatography gave 13.0 g of intermediate M44-1 as a white solid.

[0254] (2) Synthesis of intermediate M44-2:

[0255] M44-1 (9.5 g), SM3 (5.11 g), cesium carbonate (17.63 g), and DMF (95 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to 100 °C for overnight reaction. The reaction solution was quenched by pouring it into water, filtered, and the collected solid was dried. Recrystallization from toluene / ethanol gave 12.0 g of intermediate M44-2 as a white solid.

[0256] (3) Synthesis of intermediate M44-3:

[0257] Intermediate M44-2 (10.5 g), SM4 (2.05 g), tetrakis(triphenylphosphine)palladium Pd(PPh 3 ) 4 (330.7 mg), potassium carbonate (2.75 g), dioxane (105 mL), and water (31 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and then heated to reflux for overnight reaction. The reaction solution was concentrated under reduced pressure to remove dioxane. Water was added to the remaining residue and filtered. The collected solid was dried, passed through a flash column with dichloromethane, concentrated to dryness, and recrystallized from toluene / ethanol to obtain 9.5 g of intermediate M44-3 as a white solid.

[0258] (4) Synthesis of target product M44:

[0259] The synthesis procedure is the same as that of M1. Recrystallization from o-dichlorobenzene / ethanol gave 2.1 g of orange-red solid, which is the target product M44. The molecular ion mass determined by mass spectrometry: 778.56 (theoretical value: 778.30).

[0260] Synthesis Example 5: Synthesis of boron-containing organic compound M67:

[0261]

[0262]

[0263] (1) Synthesis of intermediate M67-1:

[0264] The synthesis procedure is the same as that of M1-1. Purification by column chromatography gave 12.6 g of white solid of intermediate M67-1.

[0265] (2) Synthesis of intermediate M67-2:

[0266] M67-1 (9.8 g), SM3 (5.27 g), cesium carbonate (18.18 g), and DMF (98 mL) were added to a 250 mL single-necked flask. The flask was purged with nitrogen three times and heated to 100 °C for overnight reaction. The reaction mixture was quenched by pouring it into water, filtered, and the collected solid was dried. Recrystallization from toluene / ethanol gave 11.6 g of white solid of intermediate M67-2.

[0267] (3) Synthesis of intermediate M67-3:

[0268] Intermediate M67-2 (11 g), SM4 (3.49 g), tetrakis(triphenylphosphine)palladium Pd(PPh 3 ) 4 (321.7 mg), potassium carbonate (2.89 g), dioxane (110 mL), and water (35 mL) were added to a 250 ml single-necked flask. The flask was purged with nitrogen three times and heated to reflux for overnight reaction. The reaction mixture was concentrated under reduced pressure to remove dioxane. Water was added to the remaining residue and filtered. The collected solid was dried, and the solid was purified by flash column chromatography using dichloromethane and concentrated to dryness. Recrystallization from toluene / ethanol gave 10.2 g of white solid of intermediate M67-3.

[0269] (4) Synthesis of target product M67:

[0270] The synthesis procedure is the same as that of M1. Recrystallization from o-dichlorobenzene / ethanol gave 2.6 g of orange-red solid, which is the target product M67. The molecular ion mass determined by mass spectrometry: 866.68 (theoretical value: 866.29).

[0271] Device Embodiment 1

[0272] An organic electroluminescent device includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) which are sequentially stacked.

[0273] The preparation method of the organic electroluminescent device is as follows:

[0274] (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 a mixed solvent of acetone / ethanol, bake it in a clean environment until all moisture is completely removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam;

[0275] (2) Place the glass substrate with the anode in a vacuum chamber, evacuate it 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, with a deposited film thickness of 10 nm;

[0276] (3) Vacuum deposit the compound HT-4 on the hole injection layer as the hole transport layer, with a total deposited film thickness of 60 nm;

[0277] (4) Vacuum deposit the compound HT-36 on the hole transport layer as the electron blocking layer, with a total deposited film thickness of 5 nm;

[0278] (5) Vacuum deposit the light-emitting layer on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a doping material (fluorescent dye). Using the multi-source co-evaporation method, adjust the doping ratio by adjusting the evaporation rates of various materials, with a total deposited film thickness of 40 nm;

[0279] Among them, when using the phosphorescent sensitized luminescence technology, the ratio of the host material, phosphorescent sensitizer, and doping material is 94.2:5:0.8 (w / w / w). The host material is a mixed host of PH-61:PH-3 (50 / 50, w / w), the phosphorescent sensitizer is GPD-1, and the doping material is the organic compound provided by the present invention;

[0280] (6) Vacuum deposit the compound ET-23 on the light-emitting layer as the hole blocking layer, with a total deposited film thickness of 5 nm;

[0281] (7) Vacuum deposit a mixture of ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as the electron transport layer, with a total deposited film thickness of 25 nm;

[0282] (8) Vacuum deposit LiF on the electron transport layer as the electron injection layer, with a thickness of 1 nm;

[0283] (9) An Al layer with a thickness of 150 nm was vacuum-evaporated on the electron injection layer as the cathode of the device, obtaining the organic electroluminescent device; the total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / s, and the evaporation rate of the metal electrode was controlled at 1 nm / s.

[0284] Device Example 2-22, Device Comparative Example 1-2

[0285] 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; other layers, thicknesses, materials, and preparation methods are the same as those in Device Example 1.

[0286] The structures of the fluorescent dyes in Device Comparative Example 1-4 are as follows:

[0287]

[0288] Performance test of the device:

[0289] At the same brightness, the driving voltage, the lifetime of the device, and the external quantum efficiency of each organic electroluminescent device were measured using a digital source meter and a luminance meter.

[0290] Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent device reached 10 mA / cm 2 was measured as the driving voltage, and at the same time, the emission brightness and the external quantum efficiency (EQE, %) were measured; the LT95 lifetime test was as follows: using a luminance meter at a brightness of 10000 cd / m 2 and keeping a constant current, the time when the brightness of the organic electroluminescent device dropped to 9500 cd / m 2 was measured, with the unit of h; in Table 1, the test value of the LT95 lifetime of Comparative Example 2 was recorded as 1.00, and the LT95 lifetimes of Device Examples 1-22 were all the ratios of their respective test values to the test value of Comparative Example 2 (relative lifetimes); the test results are shown in Table 1:

[0291] Table 1

[0292]

[0293]

[0294] Combined with the performance data in Table 1, it can be seen that compared with Device Comparative Examples 1-4, the boron-containing organic compound provided by the present invention as the dye of the organic electroluminescent device has excellent performance due to its specific molecular structure advantages, can effectively reduce the working voltage, improve the external quantum efficiency of the device, and improve the device lifetime, and is a green light-emitting material with good performance.

[0295] Compared with Comparative Example 2, introducing a fused structure benzindole on one side of the B-N skeleton structure of the compound of the present invention can reduce the T1 energy level of the material, inhibit the decomposition of the material caused by the thermal radiation of T1, 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.

[0296] Compared with Comparative Examples 1, 3, and 4, the compound of the present invention introduces a fused structure of Formula a at the R 3 ~R 6 position, which is beneficial to restricting the structural relaxation of the molecule in the excited state, further 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.

[0297] Compared with Comparative Examples 2 and 3, the compound of the present invention introduces an R 1 ~Z 3 group at the Z G position, which can inhibit the aggregation between molecules, inhibit the efficiency roll-off of the organic electroluminescent device, and is beneficial to the improvement of the device efficiency.

[0298] The applicant declares that the present invention uses the above embodiments to illustrate the boron-containing organic compound and its application of the present invention, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments 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, and 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, the boron-containing organic compound has a structure shown in Formula I: wherein, Ring A is selected from any one of substituted or unsubstituted C6-C60 aromatic rings; Ar 1 is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the Ar 1 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; X 1 selected from CR 11 or N; Z 1 、Z 2 、Z 3 are each independently selected from CR 12 or N; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 11 、R 12 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 heteroarylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 1 and R 2 are not connected by a chemical bond; said R 11 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; adjacent R 12 are not connected or are connected by a chemical bond to form a ring, and said R 12 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; The R 1 and R 2 at least one of which is selected from any one of substituted or unsubstituted C1-C20 straight-chain or branched-chain alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; Ring A, Ar 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 11 , R 12 The substituents in the above-mentioned substitution are each independently selected from any one of 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 in the above-mentioned substitution are each independently not connected to the adjacent ring structure or are connected into a ring through a chemical bond; The R 3 , R 4 , R 5 , R 6 Among them, one group of any two adjacent groups is connected by a chemical bond to form ring B, and the other groups except for forming ring B are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; the Ring B has a structure shown in Formula a: The dotted line represents the fused bond of Ring B; Y 1 、Y 2 、Y 3 、Y 4 each independently selected from N or CR 13 ; R 13 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 C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, 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 R 13 Each is independently not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; M 1 and M 2 are each independently selected from a single bond, NR 14 , O, S, Se, CR 15 R 16 or SiR 17 R 18 wherein at most one of the M 1 and M 2 is a single bond; R 14 、R 15 、R 16 、R 17 、R 18 are each independently selected from any one of unsubstituted or R'-substituted C1-C20 linear or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; the R 15 and R 16 are not connected or are connected by a chemical bond to form a ring; the R 17 and R 18 are not connected 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, 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-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; adjacent R's are not connected or are connected by a chemical bond to form a ring, and the R' is not connected or is connected by a chemical bond to the adjacent ring structure to form a ring.

2. The boron-containing organic compound according to claim 1, characterized in that, the boron-containing organic compound has a structure shown in Formula II: Among them, Ar 1 , X 1 , Z 1 , Z 2 , Z 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 have the same defined range as Formula I; X 2 、X 3 、X 4 、X 5 are each independently selected from CR 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 R 21 each is independently not connected to the adjacent ring structure or is connected into a ring through a chemical bond.

3. The boron-containing organic compound according to claim 2, characterized in that, the boron-containing organic compound has a structure shown in Formula III-1: Among them, X 1 、X 2 、X 3 、X 4 、X 5 、Z 1 、Z 2 、Z 3 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 have the same defined range as Formula II; Q 1 、Q 2 、Q 3 、Q 4 、Q 5 each independently selected from CR 31 or N; R 31 Each independently selected from hydrogen, 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, unsubstituted or R'-substituted C3-C60 heteroaryl; the R 31 Each is independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; Preferably, the boron-containing organic compound has a structure shown in Formula III-2: Among them, X 1 、X 2 、X 3 、X 4 、X 5 、Z 1 、Z 2 、Z 3 、R 1 、R 2 、R 3 、R 4 、R 5 、Q 1 、Q 2 、Q 3 、Q 4 has the same defined range as Formula III-1.

4. The boron-containing organic compound according to claim 3, characterized in that, the boron-containing organic compound has a structure shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4: Among them, X 1 、X 2 、X 3 、X 4 、X 5 、Z 1 、Z 2 、Z 3 、R 1 、R 2 、R 3 、R 5 、Q 1 、Q 2 、Q 3 、Q 4 have the same defined range as formula III-1; Y 1 、Y 2 、Y 3 、Y 4 have the same defined range as formula a; M 1 selected from NR 14 , O, S, CR 15 R 16 or SiR 17 R 18 any one of; R 14 、R 15 、R 16 、R 17 、R 18 each independently selected from any one of 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 C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the R 15 and R 16 are not connected or are connected by a chemical bond to form a ring; the R 17 and R 18 are not connected or are connected by a chemical bond to form a ring; Preferably, the M 1 is selected from NR 14 , O, CR 15 R 16 , and more preferably NR 14 ; Preferably, the boron-containing organic compound has a structure shown in Formula IV-1 or Formula IV-2.

5. The boron-containing organic compound according to any one of claims 1-4, characterized in that, The said Z 1 , Z 2 and Z 3 at least one of which is CR 12 , at least one of the said R 12 is the group R G , the said R G has any one of the following structures G1 - G8: -* represents the connection site of the group; X 11 、X 12 、X 13 、X 14 、X 15 Each independently selected from N or CR 20 ; R 20 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 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, 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, unsubstituted or R'-substituted C3-C60 heteroaryl; adjacent R 20 are not connected or are connected by a chemical bond to form a ring, and the R 20 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; R A1 、R A2 each independently represents unsubstituted, mono-substituted to the maximum allowable substitution; R A1 and R A2 each independently selected from any one or a combination of at least two of hydrogen, 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-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, said Z 1 , Z 2 , Z 3 are each independently selected from CR 12 , and at least one of said R 12 is the group R G ; Preferably, the Z 1 , Z 2 , Z 3 are each independently selected from CH or CR G , and one of them is CR G ; Preferably, the Z 1 and Z 3 are CH, and the Z 2 is CR G .

6. The boron-containing organic compound according to any one of claims 1-4, characterized in that, The said X 1 is CR 11 ; Preferably, the R 11 is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 straight-chain 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, said Y 1 、Y 2 、Y 3 、Y 4 are each independently selected from CR 13 ; Preferably, the R 13 each independently 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, and more preferably hydrogen.

7. The boron-containing organic compound according to any one of claims 2-4, characterized in that, Said X 2 and X 3 and X 4 and X 5 each independently selected from CR 21 ; Preferably, the R 21 each independently selected from any one of 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 more preferably hydrogen.

8. The boron-containing organic compound according to claim 4, characterized in that, Said Q 1 、Q 2 、Q 3 、Q 4 Each independently selected from CR 31 ; Preferably, the R 31 each 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 more preferably hydrogen.

9. The boron-containing organic compound according to claim 5, characterized in that, the boron-containing organic compound has a structure shown in any one of Formula V-1, Formula V-2, Formula V-3, Formula V-4: Among them, R 1 , R 2 has the same defined range as formula I; R G has any one of the structures G1 - G8: M 1 Selected from NR 14 , O, S or CR 15 R 16 Any one of; R 14 、R 15 、R 16 are each 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 C2-C20 alkenyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the R 15 and R 16 are not connected or are connected by a chemical bond to form a ring; R 13 、R 21 、R 31 each independently represents unsubstituted, mono-substituted to the maximum allowable substitution; R 13 、R 21 、R 31 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; Preferably, the boron-containing organic compound has a structure shown in Formula V-1 or Formula V-2; Preferably, the R G is connected to the para-position of the carbon atom connected to the B atom.

10. The boron-containing organic compound according to any one of claims 1-9, characterized in that, The R 1 , R 2 are each independently selected from any one of substituted or unsubstituted C1-C10 linear or branched alkyl groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups; Preferably, the R 1 , R 2 are each independently selected from a substituted or unsubstituted C1-C6 straight-chain or branched-chain alkyl group, 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 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; n is an integer selected from 0-5; Preferably, the R 1 and R 2 at least one of which is selected from More preferably, R 1 and R 2 each independently selected from Preferably, the R 1 and R 2 are each independently selected from any one of them.

11. The boron-containing organic compound according to any one of claims 5-9, characterized in that, The R G has the structure shown in any one of G1 - G5, 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 are each independently selected from 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, and unsubstituted or R'-substituted C3-C30 heteroaryl.

12. The boron-containing organic compound according to any one of claims 5-9, characterized in that, Said R G Selected from any one of the following groups: - *Represents the attachment site of the group; Preferably, the R G is selected from any one of the following groups:

13. The boron-containing organic compound according to claim 1, characterized in that, the boron-containing organic compound has a structure shown in any one of M1-M242 below:

14. An application of the boron-containing organic compound according to any one of claims 1-13, characterized in that, the boron-containing organic compound is applied to an organic electronic device; Preferably, the organic electronic device includes an organic electroluminescent device; Preferably, the boron-containing organic compound serves as a light-emitting layer material in the organic electroluminescent device.

15. An organic electroluminescent device, characterized in that the organic electroluminescent device 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 according to any one of claims 1-13; Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one boron-containing organic compound according to any one of claims 1-13; Preferably, the light-emitting layer includes a host material and a doping material, and the doping material includes at least one boron-containing organic compound according to any one of claims 1-13; Preferably, the light-emitting layer further includes a sensitizer; Preferably, the sensitizer includes any one or a combination of at least two of a thermally activated delayed fluorescence material and a phosphorescent material.

16. A display device, characterized in that the display device includes the organic electroluminescent device according to claim 15.

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