Boron-containing compound and application thereof

Abstract

The invention relates to a boron-containing compound and application thereof. The boron-containing compound provided by the invention has a structure as shown in a formula (I). The OLED device prepared from the boron-containing compound has the characteristics of low voltage and long service life, and has more excellent comprehensive performance. # imgabs0 #

Description

Technical Field

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

[0002] Organic electroluminescent display is known as the "third display technology revolution" because of its series of advantages such as self-luminescence, wide viewing angle, high contrast ratio, fast response, low power consumption, thinner and more power-saving, and flexible display, and is widely used in display and lighting fields such as mobile phones, televisions, computers, and vehicles.

[0003] With the development of organic electroluminescent materials, due to the characteristics of wide bandgap of blue light materials, it is difficult to inject charges, and they lag behind red and green lights in terms of efficiency and lifespan. Therefore, the performance of blue light emission, especially deep blue light, has an important impact on improving display quality and reducing power consumption.

[0004] Commercially promising blue light-emitting materials are required to have high efficiency and long lifespan. Chinese Patent CN103222082A discloses an aromatic vinyl compound used as a blue electroluminescent material, but this compound has poor heat resistance and is prone to cracking during the sublimation process. Another example is a series of anthracene derivatives disclosed in Chinese Patent CN1394195A, which can be used as OLED blue light materials, but the efficiency of this anthracene derivative is relatively low and cannot meet the requirements of current displays during actual application. Another example is a series of arylamine derivatives disclosed in Chinese Patent CN101018760A, but due to the imbalance between hole transport performance and electron transport performance, its service life is still not ideal. Therefore, the research and development of high-efficiency and long-lifespan blue light-emitting materials is of great significance for promoting the development of organic electroluminescent display and lighting technologies. Summary of the Invention

[0005] In view of the various defects and deficiencies in the prior art, the purpose of the present invention is to provide a boron-containing compound as an organic electroblue light-emitting material (also known as a doping material).

[0006] In the first aspect, the present invention provides a boron-containing compound having a structure shown in formula (I):

[0007]

[0008] In formula (I), ring A is selected from any one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0009] M1 and X are each independently selected from O, S, Se, NR 11 , CR 12 R 13 or SiR14 R 15 ;;

[0010] R 11 、R 12 、R 13 、R 14 、R 15 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R 11 、R 12 、R 13 、R 14 、R 15 are each independently not connected to the adjacent ring structure or connected by a chemical bond to form a ring, and the R 12 、R 13 are not connected or connected by a chemical bond to form a ring, and the R 14 、R 15 are not connected or connected by a chemical bond to form a ring;

[0011] Y1 to Y4 are each independently selected from CR Y or N;

[0012] The R Y are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C3-C30 heteroarylthio, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R Y are not connected or connected by a chemical bond to form a ring;

[0013] Ring D has the structure shown in formula (a);

[0014] In formula (a), Z1 to Z 10 are each independently selected from C, CR Z or N; wherein any one group of Z1-Z3, Z2-Z4, Z5-Z7, and Z8-Z 10 is selected from C and is fused and connected to formula (I);

[0015] The R ZEach independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and adjacent R Z are not connected or connected by a chemical bond to form a ring;

[0016] The substituents in the ring A, R Y , R Z , R 11 , R 12 , R 13 , R 14 , R 15 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 aryl, C3-C30 heteroaryl.

[0017] It is understood that any one group selected from C in Z1-Z3, Z2-Z4, Z5-Z7 and Z8-Z 10 is fused to the formula (I), and the rest are each independently selected from CR Z or N.

[0018] In the present invention, R 11 being connected to the adjacent ring structure by a chemical bond to form a ring means that R 11 is not only connected to the N atom by a chemical bond, but also connected to the adjacent ring (such as ring A or ring D) by a chemical bond (such as a single bond, O or S, etc.), 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.

[0019] 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 each group, rather than the effect of a single group / feature.

[0020] The following are the preferred technical solutions of the present invention, but not a limitation to the technical solutions provided by the present invention. Through the following preferred technical solutions, the objects and beneficial effects of the present invention can be better achieved and realized.

[0021] In some embodiments, one group selected from Z1 to Z3, or Z2 to Z4 is C and is fused to formula (I).

[0022] In some embodiments, formula (I) has a structure represented by any one of formula (I-1) to formula (I-4):

[0023]

[0024] In formula (I-1) to formula (I-4), ring A, X, M1, Y1 - Y4, Z5 - Z 10 are defined in the same manner as in formula (I).

[0025] In some embodiments, the ring A has a structure represented by formula (b) or formula (c):

[0026]

[0027] In formula (b) and formula (c), the dashed line represents the fusion position of the group;

[0028] A1 to A8 are each independently selected from CR A or N;

[0029] The R A are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 - C20 alkyl, substituted or unsubstituted C1 - C20 alkoxy, substituted or unsubstituted C1 - C20 alkylsilyl, substituted or unsubstituted C2 - C20 alkenyl, substituted or unsubstituted C3 - C20 cycloalkyl, substituted or unsubstituted C2 - C20 heterocycloalkyl, substituted or unsubstituted C6 - C30 aryloxy, substituted or unsubstituted C3 - C30 heteroaryloxy, substituted or unsubstituted C6 - C30 arylthio, substituted or unsubstituted C3 - C30 heteroarylthio, substituted or unsubstituted C6 - C30 arylamino, substituted or unsubstituted C3 - C30 heteroarylamino, substituted or unsubstituted C6 - C30 aryl, substituted or unsubstituted C3 - C30 heteroaryl, and adjacent R A are not connected to each other or are connected by a chemical bond to form a ring;

[0030] In formula (c), M2 represents O, S, NR 21 or CR 22 R 23 wherein R 21 , R 22 , R 23 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 - C20 alkyl, substituted or unsubstituted C3 - C20 cycloalkyl, substituted or unsubstituted C6 - C30 aryl, substituted or unsubstituted C3 - C30 heteroaryl, and the R22 and R 23 are not connected or are connected by a chemical bond to form a ring;

[0031] The R A , R 21 , R 22 , R 23 substituents in are each independently selected from deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 aryl, C3-C30 heteroaryl, or a combination of any one or at least two of them.

[0032] In some preferred embodiments, ring A has the structure shown in formula (b).

[0033] In some preferred embodiments, the compound has the structure shown in any one of formulae (II-1) to (III-4):

[0034]

[0035] In formulae (II-1) to (III-4), the definitions of A1, A2, A3, and A4 are the same as those in formula (b); the definitions of X, M1, Y1-Y4, Z5-Z 10 are the same as those in formula (I).

[0036] In some preferred embodiments, the compound has the structure shown in formula (II-1), formula (II-3), formula (III-1), or formula (III-3).

[0037] In some preferred embodiments, in formulae (II-1) to (III-4), X is each independently selected from O, S, or NR 11 , and R 11 has the same definition as in formula (I).

[0038] In some more preferred embodiments, the compound has the structure shown in any one of formulae (IV-1) to (IV-4):

[0039]

[0040]

[0041] In Formulas (IV-1) to (IV-4), A1, A2, A3, and A4 are defined the same as in Formula (b); M1, Y1-Y4, Z5-Z 10 , R 11 are defined the same as in Formula (I).

[0042] In some preferred embodiments, the compound has the structure shown in Formula (IV-1) or Formula (IV-2).

[0043] In some preferred embodiments, each X is independently selected from O, S, or NR 11 ;

[0044] The R 11 are each independently selected from any one of substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl; the R 11 is not connected to the adjacent ring structure or forms a ring through a chemical bond.

[0045] In some preferred embodiments, the substituents in the R 11 are each independently selected from any one or at least two combinations of deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.

[0046] In some preferred embodiments, R 11Each independently selected from any one of substituted or unsubstituted phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorene, benzofluorenyl, pyridyl, benzoxanthenyl, benzothioxanthenyl, benzonaphthofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; wherein the R 11 in the substituents of the substitution are each independently selected from deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, deuterated methyl, trifluoromethyl, deuterated tert-butyl, phenyl-substituted tert-butyl (e.g., ), cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, or any combination of one or two of them.

[0047] In some preferred embodiments, the R 11 are each independently selected from any one of the following groups, * represents the connection site of the group:

[0048]

[0049]

[0050] In some preferred embodiments, M1 represents O or S.

[0051] In some embodiments, M1 is selected from NR 11 or CR 12 R 13 , wherein the definitions of R 11 , R 12 and R 13 are the same as those defined in formula (I).

[0052] In some preferred embodiments, when M1 is selected from NR 11 or CR 12 R 13 , R 11 , R 12 and R 13 are each independently selected from hydrogen, deuterium, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl), C6-C12 aryl (such as phenyl or naphthyl).

[0053] In some preferred embodiments, at most one (0 or 1) of A1, A2, A3, A4 is selected from N, and the rest are independently selected from CR A ; preferably, A1, A2, A3, A4 are each independently selected from CR A . Multiple (such as 2, 3, 4) CR A in the RA are the same or different groups. Further preferably, A1 and A4 are selected from CH, and A2 and A3 are each independently selected from CR A .

[0054] In some preferred embodiments, at most one (0 or 1) of Y1, Y2, Y3, and Y4 is selected from N, and the rest are independently selected from CR Y ; preferably, Y1, Y2, Y3, and Y4 are each independently selected from CR Y . A plurality (such as 2, 3, or 4) of CR Y in which the R Y are the same or different groups. Further preferably, Y1 and Y4 are selected from CH, and Y2 and Y3 are each independently selected from CR Y .

[0055] In some preferred embodiments, the R A , R Y are each independently selected from hydrogen, deuterium, halogen (such as F, Cl, Br, I), cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C2-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl; the adjacent R Aare not connected or are connected into a ring through a chemical bond, and / or adjacent R Y are not connected or are connected into a ring through a chemical bond;

[0056] The R A , R Y The substituents in are each independently selected from any one or a combination of at least two of deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (C6, C9, C10, C12, C14, C15, C16, C18, C19, etc.) aryl, and C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C19, etc.) heteroaryl.

[0057] In some preferred embodiments, the R A , R Y are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0058] The R A , R Y The substituents in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0059] In some preferred embodiments, the R A , R Y are each independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, where * represents the connection site of the group:

[0060] *-CH3, *-CD3, *-CF3,

[0061] In some embodiments, adjacent R Aare not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) carbocyclic ring, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C19, etc.) heteroaromatic ring or a substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, and / or adjacent R Y are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) carbocyclic ring, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C19, etc.) heteroaromatic ring or a substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring.

[0062] In some preferred embodiments, the substituents of the "substituted or unsubstituted" in the above rings are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, and C3-C8 cycloalkyl.

[0063] In some preferred embodiments, adjacent R A are not connected or are connected by a chemical bond to form a ring, and / or adjacent R Y are not connected or are connected by a chemical bond to form a ring (such as forming etc., the dashed line represents a fused bond).

[0064] In some preferred embodiments, at most one (0 or 1) of Z5, Z6, Z7 is selected from N, and the rest are independently selected from CR Z ; and / or at most one (0 or 1) of Z8, Z9, Z 10 is selected from N, and the rest are independently selected from CR Z ; preferably, Z5, Z6, Z7, Z8, Z9, Z 10 are each independently selected from CR Z . Multiple (such as 2, 3, 4, 5, 6, 7, 8) CR Z in which R Z are the same or different groups. Further preferably, Z5, Z 10 is selected from CH; Z6, Z7, Z8, Z9 are each independently selected from CR Z .

[0065] In some preferred embodiments, the R ZEach independently selected from hydrogen, deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, any one or a combination of at least two; preferably, the R Z Each independently selected from hydrogen, deuterium, halogen, cyano, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.), C3-C8 cycloalkyl (such as cyclopentyl, cyclohexyl, etc.), C6-C12 aryl (such as phenyl, naphthyl, etc.), C3-C12 heteroaryl (such as pyridine, etc.), any one or a combination of two; more preferably, R Z Each independently selected from hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, or phenyl; further preferably, R Z All are selected from hydrogen.

[0066] In some embodiments, the boron-containing compound has a structure represented by any one of Formula (V-1) to Formula (VI-4):

[0067]

[0068]

[0069] For Formula (V-1) to Formula (VI-4), the definition of R A is the same as its definition in Formula (b), and the definitions of M1, R Y 、R Z and X are the same as their definitions in Formula (I), m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3 or 4, and p is 0, 1, 2, 3, 4, 5 or 6.

[0070] In some embodiments, M1 is selected from O or S.

[0071] In some embodiments, R A 、R YEach independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C3-C20 heteroarylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl; adjacent R A are not connected or are connected by a chemical bond to form a ring, and / or adjacent R Y are not connected or are connected by a chemical bond to form a ring;

[0072] Optionally, the substituents in the substituted R A and R Y are each independently selected from any one or a combination of at least two of deuterium, fluorine, chlorine, bromine, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl.

[0073] In some embodiments, R Z are each independently preferably selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl.

[0074] In some embodiments, X is each independently selected from O, S or NR 11 ;

[0075] The R 11 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; optionally, the substituents in the substituted R 11 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl.

[0076] In some embodiments, the boron-containing compound has a structure represented by any one of formula (V-1-1), formula (V-1-2), formula (V-3-1), formula (V-3-2), formula (VI-1-1), formula (VI-1-2), formula (VI-3-1), formula (VI-3-2):

[0077]

[0078] In formula (V-1-1), formula (V-1-2), formula (V-3-1), formula (V-3-2), formula (VI-1-1), formula (VI-1-2), formula (VI-3-1), and formula (VI-3-2), R A is defined in the same manner as in formula (b), and M1, R Y , R Z and R 11 are defined in the same manner as in formula (I), m is 0, 1, 2, 3, or 4, m' is 0, 1, 2, or 3, n is 0, 1, 2, 3, or 4, p is 0, 1, 2, 3, 4, 5, or 6, and q is 0, 1, 2, 3, or 4;

[0079] In formula (VI-1-2) and formula (VI-3-2), W represents a single bond, O, or S;

[0080] In formula (V-1-2), formula (V-3-2), formula (VI-1-2), and formula (VI-3-2), R 11a are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R 11a are not connected or are connected by a chemical bond to form a ring; the substituents of the substituted R 11a are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0081] In some preferred embodiments, adjacent R 11a are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) carbocyclic ring, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C19, etc.) heteroaromatic ring, or a substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring.

[0082] In some preferred embodiments, the substituents of the "substituted or unsubstituted" in the above rings are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, and C3-C8 cycloalkyl.

[0083] In some preferred embodiments, adjacent R 11aare not connected or are connected by a chemical bond to form a ring (for example, forming , etc., and the dashed line represents a fused bond).

[0084] In some embodiments, M1 is selected from O or S.

[0085] In some embodiments, R A , R Y are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl, and optionally, the substituents of the substituted R A , R Y are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, or a combination of any one or at least two of them.

[0086] In some embodiments, the R A , R Y are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, or any of the following groups:

[0087] *-CH3, *-CD3, *-CF3,

[0088] In some embodiments, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, or a combination of any one or two of them.

[0089] In some embodiments, R Z are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl.

[0090] In some embodiments, R 11 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl, and optionally, the substituents of the substituted R 11 are each independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, or a combination of any one or at least two of them.

[0091] In some embodiments, the R 11Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, benzonaphthofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl.

[0092] In some embodiments, the R 11 Substituents of the substitution are each independently selected from one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl, pivalyl, deuterated methyl, trifluoromethyl, deuterated tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl.

[0093] In some embodiments, the R 11 Each independently selected from any one of the following groups:

[0094]

[0095] In some embodiments, the boron-containing compound has a structure represented by formula (V-1-3) or formula (V-3-3):

[0096]

[0097] In formula (V-1-3) and formula (V-3-3), the definition of R A is the same as its definition in formula (b), the definitions of M1, R Y and R Z are the same as their definitions in formula (I), m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3 or 4, p is 0, 1, 2, 3, 4, 5 or 6;

[0098] Q each independently represents O, S, or NR 11 ; where at least one Q is selected from O or S;

[0099] The R 11 Each independently selected from any one of C1-C10 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C10 alkyl-substituted or unsubstituted C3-C30 aryl, preferably selected from any one of C1-C6 alkyl-substituted or unsubstituted C6-C12 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C12 aryl.

[0100] In some embodiments, the organic boron-containing compound of the present invention has a structure represented by any one of the following:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] In a second aspect, the present invention provides an application of the above boron-containing compound in the preparation of an organic electroluminescent device.

[0129] According to some preferred embodiments of the present invention, the boron-containing compound is used as a doping material (also known as a dopant or fluorescent dye or dye or luminescent material or guest material) in the light-emitting layer of the organic electroluminescent device.

[0130] In a third aspect, the present invention provides an organic electroluminescent device, comprising a light-emitting layer, wherein the light-emitting layer comprises a host material and a doping material, and the doping material contains the above boron-containing compound of the present invention.

[0131] In some embodiments, the mass ratio of the host material to the doping material is from 99:1 to 70:30 (such as 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 88:12, 85:15, 83:17, 80:20, 77:23, 75:25, 73:27, etc.). The doping material is dispersed in the host material, and the mass ratio of the host material to the doping material being from 99:1 to 70:30 is beneficial to suppressing crystallization of the light-emitting layer and suppressing concentration quenching caused by high concentration of the doping material, thereby improving the light-emitting efficiency of the device.

[0132] According to some preferred embodiments of the present invention, the organic electroluminescent device comprises: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In some embodiments, the light-emitting layer comprises a doping material.

[0133] According to some preferred embodiments of the present invention, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0134] In a fourth aspect, the present invention provides a display component / device, which comprises the boron-containing compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention.

[0135] The OLED device prepared by using the boron-containing compound of the present invention has low voltage and high lifespan, and can meet the requirements of current panel manufacturing enterprises for high-performance materials.

[0136] The beneficial effects of the present invention are as follows:

[0137] The boron-containing compound provided by the present invention has the structure shown in formula (I). By fusing a bulky group on the parent nucleus, a larger conjugated system and a larger rigid plane are formed, thereby improving the material properties. When it is applied to the light-emitting layer of an organic electroluminescent device, the efficiency and lifespan of the device can be enhanced. Detailed Embodiments

[0138] The technical solutions of the present invention will be described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention. Any equivalent changes or modifications made without departing from the spirit disclosed by the present invention shall be included within the scope of the corresponding claims.

[0139] Definition of Substituent Terms

[0140] In the present invention, for the description 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.

[0141] In the present invention, unless otherwise specified, the heteroatoms of heteroaryl are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms in heterocycloalkyl are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0142] In the present invention, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure where a bond can be formed.

[0143] In the present invention, both "-*" and "*" represent the connection sites of groups.

[0144] In the present invention, "independently of each other" means that when the subject has a plurality of them, they can be the same or different from each other.

[0145] 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 substituents.

[0146] In the present invention, 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.

[0147] In the present invention, C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0148] In the present invention, C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0149] In the present invention, C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0150] In the present invention, C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0151] In the present invention, unless otherwise specified, the C6-C30 aryl group (C6-C30 aromatic ring) includes monocyclic aryl groups and polycyclic aryl groups; the monocyclic aryl group means that the group contains at least 1 phenyl group, and when there are 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 that the group contains at least 2 rings (and at least 1 ring is an aromatic ring), and the rings are fused to each other by sharing two adjacent carbon atoms. Exemplarily, it includes but is not limited to: naphthyl, anthracenyl, 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-methyl-9-phenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl, benzofluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl, etc.), fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, base, tetraphenyl, acenaphthylenyl, benzacenaphthylenyl, etc. It should be noted that the monocyclic aryl group and the polycyclic aryl group connected by single bonds also belong to the scope of aryl groups, such as phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0152] In the present invention, unless otherwise specified, the C6-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes a monocyclic heteroaryl group or a fused-ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl groups, heteroaryl groups, etc.), the heteroaryl group and other groups are connected by a single bond. Exemplarily, it includes but is not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused-ring heteroaryl group means that the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aryl 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, benzonaphthofuryl (benzo[B]naphtho[2,3-D]furyl, benzo[B]naphtho[1,2-D]furyl, benzo[B]naphtho[2,1-D]furyl), dibenzothienyl, benzonaphthothienyl (benzo[B]naphtho[2,3-D]thienyl, benzo[B]naphtho[1,2-D]thienyl, benzo[B]naphtho[2,1-D]thienyl), carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.

[0153] In the present invention, specific examples of the C6-C30 arylamino group are monovalent groups obtained by substituting at least one hydrogen in -NH2 with the above-mentioned aryl groups. Exemplarily, it includes but is not limited to: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups obtained by substituting at least one hydrogen in -NH2 with the above-mentioned heteroaryl groups. Exemplarily, it includes but is not limited to: pyridylamino, pyrimidinylamino, dibenzofurylamino, etc.

[0154] 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.

[0155] In the present invention, the C6-C30 arylthio group is a monovalent group formed by connecting the above-mentioned aryl group with S, and the C3-C30 heteroarylthio group is a monovalent group formed by connecting the above-mentioned heteroaryl group with S.

[0156] In the present invention, the C1-C20 alkyl group, preferably the C1-C16 alkyl group, more preferably the C1-C10 alkyl group, exemplarily 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.

[0157] In the present invention, specific examples of the C1-C20 alkoxy group can be a monovalent group obtained by connecting an oxygen atom to the examples of the above alkyl groups.

[0158] In the present invention, specific examples of the C1-C20 alkylsilyl group are monovalent groups obtained by substituting at least one hydrogen in -SiH3 with the above alkyl groups, exemplarily including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0159] In the present invention, the C3-C20 cycloalkyl group, preferably the C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. Among them, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms, exemplarily including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0160] In the present invention, specific examples of the C2-C20 heterocycloalkyl group can be groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), exemplarily including but not limited to: epoxy group, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxanyl, morpholinyl, etc.

[0161] In the present invention, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, contains at least one C═C, exemplarily including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0162] In the present invention, the "substituted or unsubstituted" group can be substituted with one substituent or multiple substituents. When there are multiple substituents (at least 2), they can be the same or different substituents; when the same expression is involved above, it has the same meaning. Unless otherwise specified, the selection range of the substituents is as shown in the present invention and will not be elaborated herein.

[0163] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used in the present invention, these different ways of specifying substituents or linking fragments are considered equivalent.

[0164] In the compounds mentioned in the present invention, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0165] In the compounds mentioned in the present invention, multiple substitution refers to the range including double substitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present invention indicates multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linking structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.

[0166] In the compounds mentioned in the present invention, unless explicitly defined, for example, adjacent substituents can optionally link to form a ring, otherwise adjacent substituents in the compounds cannot link to form a ring. In the compounds mentioned in the present invention, adjacent substituents can optionally link to form a ring, which includes both the case where adjacent substituents can link to form a ring and the case where adjacent substituents do not link to form a ring. When adjacent substituents can optionally link to form a ring, the formed ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this description, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0167] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combination of these materials is described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122M, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed in the present invention, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0168] The materials described for specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed in the present invention can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of US Patent Application US2015 / 0349273M, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed in the present invention, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0169] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.) by methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art (including but not limited to the evaporation coater produced by Nanjing Microelectronics Institute, the optical test system and lifetime test system produced by Suzhou Fosida, the ellipsometer produced by Wuhan Yiguang Technology, etc.) by methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above devices, test methods, etc., and can obtain the inherent data of the samples determinately and without interference, the above relevant content will not be elaborated further in this invention.

[0170] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0171] Example 1: Synthesis of Compound I-1

[0172]

[0173] (1-1) Synthesis of Intermediate S1-1:

[0174] Under nitrogen protection, raw material M1-1 (37.99 g), raw material M1-2 (19.20 g), anhydrous potassium carbonate (27.64 g), Pd(PPh3)4 (2.31 g), toluene (300 mL), ethanol (100 mL) and deionized water (100 mL) were added to a dry three-necked reaction flask, and the temperature was raised to 100 °C and reacted for 5 h. After the reaction was completed, the temperature was lowered to room temperature, washed with water and separated by liquid separation. The aqueous phase was extracted with toluene, the organic phase was collected, purified by column chromatography, recrystallized, and dried to obtain intermediate S1-1 (28.34 g, yield 70.9%).

[0175] (1-2) Synthesis of intermediate S1-2:

[0176] Under nitrogen protection, intermediate S1-1 (28.00 g) and tetrahydrofuran (150 mL) were added to a dry three-necked reaction flask, the temperature was lowered to -78 °C, stirred for 0.5 h, and a pentane solution of tert-butyllithium (52.5 mL, 1.6 M) was slowly added dropwise. The temperature was controlled at -78 °C and reacted for 1 h, then the solution of raw material M1-3 (10.51 g) in tetrahydrofuran (70 mL) was added dropwise while maintaining the temperature, and the reaction was continued for 1 h while maintaining the temperature, and then slowly raised to room temperature and continued to react for 8 h. The reaction was quenched by adding a saturated ammonium chloride solution, diluted with water, separated by liquid separation, the aqueous phase was extracted with dichloromethane (60 mL), the organic phases were combined, concentrated to remove the solvent, and an oily substance was obtained. Then acetic acid (50 mL) and concentrated hydrochloric acid (10 mL) were added, and the temperature was raised to 70 °C and reacted overnight. After cooling, the solvent was removed by concentration, dichloromethane (20 mL) and water (20 mL) were separated by liquid separation, the organic phases were combined, washed with saturated sodium bicarbonate until neutral, washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate S1-2 (15.49 g, yield 54.5%).

[0177] (1-3) Synthesis of intermediate S1-3:

[0178] Under nitrogen protection, intermediate S1-2 (14.21 g), raw material M1-4 (3.29 g), potassium carbonate (9.67 g) and NMP (150 mL) were added to a dry three-necked reaction flask, and the temperature was raised to 150 °C and reacted for 6 h. After the reaction was completed, the temperature was lowered to room temperature, distilled under reduced pressure, water (100 mL) and ethyl acetate (100 mL) were added, separated by liquid separation and then distilled under reduced pressure, and purified by column chromatography to obtain intermediate S1-3 (13.55 g, yield 80.6%).

[0179] MS (m / e) of intermediate S1-3: 480.23; 1HNMR(400MHz,CDCl3): δ 8.00 - 7.92(m, 2H), 7.60(t, 1H), 7.52(dd, 1H), 7.46 - 7.32(m, 4H), 7.14 - 7.06(m, 1H), 7.05 - 6.99(m, 2H), 6.83(s, 1H), 2.24 - 2.16(m, 2H), 2.02 - 1.91(m, 2H), 1.81 - 1.68(m, 10H) 。 (1 - 4) Synthesis of Intermediate S1 - 4:

[0180] Under nitrogen protection, add Intermediate S1 - 3 (9.60 g), raw material M1 - 5 (2.68 g), potassium carbonate (5.53 g) and NMP (120 mL) to a dry three - necked reaction flask, heat up to 120 °C and react for 12 h. After the reaction is completed, cool down to room temperature, distill under reduced pressure, add water (100 mL) and ethyl acetate (100 mL), separate the layers by liquid - liquid extraction and then distill under reduced pressure, and purify by column chromatography to obtain Intermediate S1 - 4 (9.46 g, yield 79.6%).

[0181] (1 - 5) Synthesis of Compound I - 1:

[0182] Under nitrogen protection, add Intermediate S1 - 4 (5.94 g) and anhydrous xylene (150 mL) to a dry three - necked reaction flask, cool down to - 78 °C, slowly dropwise add tert - butyllithium pentane solution (12.5 mL, 1.6 M), then slowly heat up to 60 °C and react for 3 h. Stop heating, cool down to - 78 °C, add boron tribromide (2.4 mL), and react at room temperature for 6 h. Then cool down to 0 °C and dropwise add N,N - diisopropylethylamine (7.0 mL), react at 140 °C for 13 h. After the reaction is completed, cool down to room temperature, wash with water, separate the layers, dry and concentrate, and purify by column chromatography and recrystallization to obtain Compound I - 1 (1.07 g, yield 18.8%).

[0183] MS (m / e) of Compound I - 1: 568.47; 1 HNMR(400MHz,CDCl3): δ 8.00 - 7.91(m, 2H), 7.87(dt, 1H), 7.66(dd, 1H), 7.59(t, 1H), 7.51(d, 1H), 7.46 - 7.38(m, 3H), 7.35(dd, 1H), 7.33 - 7.21(m, 2H), 7.00(td, 1H), 6.91(dd, 1H), 6.74(s, 1H), 2.24 - 2.16(m, 2H), 2.02 - 1.91(m, 2H), 1.81 - 1.68(m, 10H).

[0184] Example 2: Synthesis of Compound I - 37

[0185]

[0186]

[0187] (2-1) Synthesis of Intermediate S2-1:

[0188] Under nitrogen protection, add raw material M2-1 (23.99 g) to a dry three-necked reaction flask, slowly drop trifluoromethanesulfonic acid (88.49 mL) at 0 °C, and react for 2 h. After the reaction is completed, pour it into ice water (800 mL), precipitate a solid, filter, wash three times with water (100 mL) and methanol (100 mL) to obtain intermediate S2-1 (19.28 g, yield 51.9%).

[0189] (2-2) Synthesis of Intermediate S2-2:

[0190] The synthesis route of intermediate S2-2 is the same as that of intermediate S1-1. Only replace raw material M1-1 with intermediate S2-1 and raw material M1-2 with raw material M2-2 to obtain intermediate S2-2.

[0191] (2-3) Synthesis of Intermediate S2-3:

[0192] The synthesis route of intermediate S2-3 is the same as that of intermediate S1-2. Only replace intermediate S1-1 with intermediate S2-2 to obtain intermediate S2-3.

[0193] (2-4) Synthesis of Intermediate S2-4:

[0194] Under nitrogen protection, add intermediate S2-3 (16.87 g), raw material M2-3 (9.84 g), sodium tert-butoxide (6.73 g), Pd2(dba)3 (0.64 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.33 g) and toluene (200 mL) to a dry three-necked reaction flask, slowly heat to 105 °C with stirring, and react for 6 h. After the reaction solution is cooled, add water (100 mL), wash and concentrate, perform column chromatography, recrystallize, and dry to obtain intermediate S2-3 (14.91 g, yield 62.3%).

[0195] (2-5) Synthesis of Intermediate S2-5:

[0196] Under nitrogen protection, add intermediate S2-4 (13.67 g), raw material M2-4 (6.74 g), sodium tert-butoxide (3.84 g), Pd2(dba)3 (0.37 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.76 g) and toluene (150 mL) into a dry three-necked reaction flask. Slowly heat up to 100 °C with stirring and react for 8 h. After the reaction solution is cooled, add water (100 mL), wash with water and concentrate, carry out column chromatography, recrystallize, and dry to obtain intermediate S2-5 (12.03 g, yield 61.1%).

[0197] (2-6) Synthesis of compound I-37:

[0198] The synthesis route of compound I-37 is the same as that of compound I-1. Only by replacing intermediate S1-4 with intermediate S2-5 can compound I-37 be obtained.

[0199] MS (m / e) of compound I-37: 958.21; 1 1H NMR (400 MHz, CDCl3): δ 8.00 - 7.92 (m, 2H), 7.82 (d, 1H), 7.73 (d, 1H), 7.63 - 7.57 (m, 1H), 7.51 (d, 1H), 7.45 - 7.34 (m, 3H), 7.31 - 7.24 (m, 5H), 7.21 (dd, 1H), 7.08 - 6.97 (m, 6H), 2.24 - 2.16 (m, 2H), 2.02 - 1.91 (m, 2H), 1.81 - 1.68 (m, 10H), 1.37 - 1.32 (m, 36H).

[0200] Example 3: Synthesis of compound I-87

[0201]

[0202] The synthesis route of compound I-87 is the same as that of compound I-37. Only by replacing raw material M2-3 with raw material M3-1 can compound I-87 be obtained.

[0203] MS (m / e) of compound I-87: 1166.07; 1HNMR(400MHz, CDCl3): δ 8.00 - 7.92 (m, 2H), 7.81 (dd, 2H), 7.73 (d, 1H), 7.64 - 7.58 (m, 2H), 7.53 - 7.48 (m, 3H), 7.46 - 7.25 (m, 13H), 7.21 (dd, 1H), 7.07 - 6.97 (m, 4H), 2.25 - 2.17 (m, 2H), 2.02 - 1.92 (m, 2H), 1.81 - 1.68 (m, 10H), 1.36 - 1.32 (m, 45H).

[0204] Example 4: Synthesis of Compound I - 184

[0205]

[0206] (4 - 1) Synthesis of Raw Material M4 - 1:

[0207] The synthesis route of raw material M4 - 1 is the same as that of intermediate S2 - 4. Just replace intermediate S2 - 3 with raw material M4 - 1a and raw material M2 - 3 with raw material M4 - 1b to obtain raw material M4 - 1.

[0208] (4 - 2) Synthesis of Compound I - 184:

[0209] The synthesis route of Compound I - 184 is the same as that of Compound I - 37. Just replace raw material M2 - 4 with raw material M4 - 1 to obtain Compound I - 184.

[0210] MS (m / e) of Compound I - 184: 967.36; 1 HNMR(400MHz, CDCl3): δ 8.00 - 7.92 (m, 2H), 7.69 (dd, 1H), 7.60 (t, 1H), 7.54 - 7.47 (m, 4H), 7.46 - 7.34 (m, 3H), 7.31 - 7.24 (m, 3H), 7.21 (dd, 1H), 7.18 - 7.13 (m, 2H), 7.08 - 6.97 (m, 4H), 2.25 - 2.17 (m, 2H), 2.01 - 1.92 (m, 2H), 1.81 - 1.68 (m, 10H), 1.37 - 1.32 (m, 27H).

[0211] Example 5: Synthesis of Compound II - 32

[0212]

[0213] (5 - 1) Synthesis of Intermediate S5 - 2:

[0214] The synthetic route of intermediate S5-2 is the same as that of intermediate S1-2. By simply replacing raw material M1-2 with raw material M5-1, intermediate S5-2 can be obtained. (5-2) Synthesis of intermediate S5-3:

[0215] Under nitrogen protection, add intermediate S5-2 (9.32 g), raw material M5-2 (5.58 g), cesium carbonate (13.03 g) and DMF (120 mL) to a dry three-necked reaction flask. Heat the mixture to 90 °C and react for 12 h. After the reaction is completed, cool the mixture to room temperature, add water (400 mL), precipitate a solid, filter, and wash the filter cake with ethanol by boiling to obtain intermediate S5-3 (7.35 g, yield 50.7%).

[0216] (5-3) Synthesis of compound II-32:

[0217] The synthetic route of compound II-32 is the same as that of compound I-37. By simply replacing intermediate S2-4 with intermediate S5-3, compound II-32 can be obtained.

[0218] MS (m / e) of compound II-32: 956.78; 1 1H NMR (400 MHz, CDCl3): δ 8.35 (d, 1H), 8.00 - 7.92 (m, 3H), 7.82 (d, 1H), 7.73 (dd, 2H), 7.63 - 7.54 (m, 2H), 7.51 (d, 1H), 7.45 - 7.34 (m, 3H), 7.30 - 7.23 (m, 3H), 7.17 (s, 1H), 7.06 - 7.01 (m, 2H), 2.25 - 2.17 (m, 2H), 2.01 - 1.92 (m, 2H), 1.81 - 1.68 (m, 10H), 1.37 - 1.32 (m, 36H).

[0219] Example 6: Synthesis of compound II-131

[0220]

[0221] (6-1) Synthesis of raw material M6-2:

[0222] The synthetic route of raw material M6-2 is the same as that of raw material M4-1. By simply replacing raw material M4-1a with raw material M6-2a and raw material M4-1b with raw material M6-2b, raw material M6-2 can be obtained.

[0223] (6-2) Synthesis of compound II-131:

[0224] The synthetic route of compound II-131 is the same as that of compound I-37. By simply replacing raw material M2-1 with raw material M6-1, raw material M2-3 with raw material M6-2, and raw material M2-4 with raw material M6-3, compound II-131 can be obtained.

[0225] MS (m / e) of compound II-131: 1042.76; 1 HNMR (400 MHz, CDCl3): δ 8.35 (d, 1H), 8.18 (d, 1H), 8.05 (d, 1H), 8.00 - 7.84 (m, 4H), 7.69 (dd, 2H), 7.64 - 7.48 (m, 5H), 7.46 - 7.34 (m, 3H), 7.31 - 7.19 (m, 5H), 7.05 - 6.96 (m, 4H), 2.25 - 2.17 (m, 2H), 2.02 - 1.92 (m, 2H), 1.81 - 1.68 (m, 10H), 1.37 - 1.32 (m, 27H).

[0226] Example 7: Synthesis of compound II-192

[0227]

[0228] (7-1) Synthesis of raw material M7-2:

[0229] The synthetic route of raw material M7-2 is the same as that of raw material M4-1. By simply replacing raw material M4-1a with raw material M7-2a and raw material M4-1b with raw material M7-2b, raw material M7-2 can be obtained.

[0230] (7-2) Synthesis of compound II-192:

[0231] The synthetic route of compound II-192 is the same as that of compound II-131. By simply replacing raw material M6-2 with raw material M7-1 and raw material M6-3 with raw material M7-2, compound II-192 can be obtained.

[0232] MS (m / e) of compound II-192: 1121.21; 1 HNMR (400 MHz, CDCl3): δ 8.17 - 8.11 (m, 2H), 8.00 - 7.92 (m, 2H), 7.81 (d, 1H), 7.73 (d, 1H), 7.68 - 7.57 (m, 3H), 7.51 (d, 1H), 7.46 - 7.12 (m, 14H), 7.02 - 6.92 (m, 4H), 2.25 - 2.17 (m, 2H), 2.02 - 1.92 (m, 2H), 1.84 - 1.58 (m, 14H), 1.37 - 1.28 (m, 30H).

[0233] Example 8: Synthesis of Compound III-33

[0234]

[0235] (8-1) Synthesis of Raw Material M8-2:

[0236] The synthesis route of raw material M8-2 is the same as that of raw material M7-2. By only replacing raw material M7-2b with raw material M8-2b, raw material M8-2 can be obtained. (8-2) Synthesis of Intermediate S8-1:

[0237] The synthesis route of intermediate S8-1 is the same as that of intermediate S1-1. By only replacing raw material M1-2 with raw material M8-1, intermediate S8-1 can be obtained. (8-3) Synthesis of Intermediate S8-2a and Intermediate S8-2b:

[0238] The synthesis routes of intermediate S8-2a and intermediate S8-2b are the same as those of intermediate S1-2. By only replacing intermediate S1-1 with intermediate S8-1, intermediate S8-2a and intermediate S8-2b can be obtained.

[0239] MS (m / e) of intermediate S8-2a: 482.39; 1 HNMR (400 MHz, CDCl3): δ 8.27 (d, 1H), 8.00 - 7.92 (m, 2H), 7.81 (s, 1H), 7.66 - 7.59 (m, 1H), 7.46 - 7.38 (m, 2H), 2.26 - 2.19 (m, 2H), 2.02 - 1.92 (m, 2H), 1.82 - 1.68 (m, 10H).

[0240] MS (m / e) of intermediate S8-2b: 482.64; 1 HNMR (400 MHz, CDCl3): δ 8.27 (d, 1H), 8.00 - 7.92 (m, 2H), 7.80 (s, 1H), 7.66 - 7.59 (m, 1H), 7.46 - 7.35 (m, 2H), 2.20 - 2.12 (m, 2H), 2.01 - 1.93 (m, 2H), 1.82 - 1.68 (m, 10H).

[0241] (8-4) Synthesis of Compound III-33:

[0242] The synthesis route of compound III-33 is the same as that of compound I-37. By only replacing intermediate S2-3 with intermediate S8-2a and raw material M2-4 with raw material M8-2, compound III-33 can be obtained.

[0243] MS (m / e) of Compound III-33: 1090.87; 1 HNMR (400 MHz, CDCl3): δ 8.25 (dd, 1H), 8.00 - 7.92 (m, 2H), 7.82 (d, 1H), 7.73 (d, 1H), 7.65 - 7.47 (m, 5H), 7.46 - 7.18 (m, 11H), 7.06 - 6.97 (m, 3H), 2.24 - 2.15 (m, 2H), 2.02 - 1.92 (m, 2H), 1.82 - 1.68 (m, 10H), 1.37 - 1.32 (m, 45H).

[0244] Example 9: Synthesis of Compound IV-47

[0245]

[0246] The synthetic route of Compound IV-47 is the same as that of Compound III-33, except that intermediate S8-2a is replaced by intermediate S8-2b, raw material M2-3 is replaced by raw material M9-1, and raw material M8-2 is replaced by raw material M9-2, then Compound IV-47 can be obtained.

[0247] MS (m / e) of Compound IV-47: 1052.27; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.00 - 7.92 (m, 2H), 7.69 (d, 1H), 7.64 - 7.60 (m, 1H), 7.54 (d, 1H), 7.48 (s, 1H), 7.46 - 7.34 (m, 3H), 7.28 (dd, 1H), 7.24 - 7.18 (m, 2H), 7.16 - 7.13 (m, 1H), 7.02 - 6.93 (m, 5H), 2.23 - 2.15 (m, 2H), 2.02 - 1.92 (m, 2H), 1.84 - 1.59 (m, 14H), 1.37 - 1.28 (m, 48H).

[0248] Specific synthetic methods of several above compounds are exemplarily given in the present invention. For compounds without specific synthetic methods, they are also prepared by similar methods, only by replacing raw materials, which will not be elaborated here, or those skilled in the art can also prepare them by other methods in the prior art.

[0249] Device Example 1

[0250] Clean the glass substrate, which has a 120-nm-thick indium tin oxide (ITO) anode, and then treat it with UV ozone and oxygen plasma. After treatment, dry the substrate in a nitrogen-filled glove box to remove moisture, then mount the substrate on a substrate holder and load it into a vacuum chamber.

[0251] At a vacuum of about 10 -8 Torr, sequentially deposit films on the ITO anode by thermal vacuum at a rate of . At the same time, co-deposit compounds HT and HI (weight ratio 97:3) as the hole injection layer (HIL), with a thickness of Compound HT is used as the hole transport layer (HTL), with a thickness of Compound EB is used as the electron blocking layer (EBL), with a thickness of Then, co-deposit compound BH as the blue light host and compound I-1 as the doping material (weight ratio 98:2) as the emitting layer (EML), with a thickness of Use compound HB as the hole blocking layer (HBL), with a thickness of On the hole blocking layer, co-deposit compound ET and lithium 8-hydroxyquinolate (Liq) (weight ratio 50:50) as the electron transport layer (ETL), with a thickness of Finally, deposit Thickness of lithium 8-hydroxyquinolate (Liq) as the electron injection layer (EIL), and deposit Aluminum of

[0252] Device Examples 2-9, Device Comparative Examples 1-3

[0253] The difference from Device Example 1 is only that the doping materials of the emitting layer are the compounds shown in Table 1 respectively; other layers, thicknesses, materials, and preparation methods are the same as those of Device Example 1.

[0254] The molecular structural formulas of the related materials are shown as follows:

[0255]

[0256] Table 1 lists the measured voltage (V), external quantum efficiency (EQE), and lifetime (h) under the condition of a current density of 10 mA / cm 2 . To better show the data comparison, the voltage, external quantum efficiency, and lifetime of Device Comparative Example 1 are set to 100% respectively. The voltage, efficiency, and lifetime data of Device Examples 1-9 and Device Comparative Examples 2-3 are all converted relative to the corresponding data of Device Comparative Example 1, and the relevant data and conversion results are shown in Table 1.

[0257] Table 1

[0258] Device Doped material Voltage (V) EQE Lifetime (h) Device Example 1 I-1 96％ 105％ 111％ Device Example 2 I-37 93％ 114％ 120％ Device Example 3 I-87 92％ 120％ 128％ Device Example 4 I-184 92％ 117％ 126％ Device Example 5 II-32 91％ 121％ 124％ Device Example 6 II-131 93％ 119％ 123％ Device Example 7 II-192 92％ 118％ 122％ Device Example 8 III-33 94％ 113％ 119％ Device Example 9 IV-47 94％ 115％ 117％ Device Comparative Example 1 Ref-1 100％ 100％ 100％ Device Comparative Example 2 Ref-2 116％ 82％ 78％ Device Comparative Example 3 Ref-3 129％ 77％ 71％

[0259] As shown in Table 1, at a current density of 10 mA / cm 2 the voltage of Device Examples 1-9 can be reduced by 4-9% compared to Device Comparative Examples 1-3, the external quantum efficiency is increased by 5%-21%, and the device lifetime is extended, with a maximum extension of 28%. The above data show that the device prepared from the boron-containing compound provided by the present invention has a lower driving voltage, higher current efficiency and longer lifetime.

[0260] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A boron-containing compound having the structure shown in formula (I): In formula (I), ring A is selected from any one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring; M1 and X are each independently selected from O, S, Se, NR 11 , CR 12 R 13 or SiR 14 R 15 ; R 11 、R 12 、R 13 、R 14 、R 15 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R 11 、R 12 、R 13 、R 14 、R 15 are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond, and the R 12 、R 13 are not connected or connected into a ring through a chemical bond, and the R 14 、R 15 are not connected or connected into a ring through a chemical bond; Y1 to Y4 are each independently selected from CR Y or N; The R Y are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C3-C30 heteroarylthio, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and any two adjacent R Y are not connected or are connected by a chemical bond to form a ring; Ring D has the structure shown in formula (a); In formula (a), Z1 to Z 10 are each independently selected from C, CR Z or N; wherein any one of Z1-Z3, Z2-Z4, Z5-Z7 and Z8-Z 10 is selected from C and is fused and linked to formula (I); The R Z are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R Z are not connected or are connected by a chemical bond to form a ring; The substituents substituted in the rings A, R Y , R Z , R 11 , R 12 , R 13 , R 14 , R 15 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 aryl, and C3-C30 heteroaryl.

2. The boron-containing compound according to claim 1, characterized in that, The boron-containing compound has the structure shown in any one of formula (I-1) to formula (I-4): In formulas (I-1) to (I-4), ring A, X, M1, Y1-Y4, Z5-Z 10 are defined in the same manner as in formula (I); Preferably, ring A has the structure shown in formula (b) or formula (c), preferably the structure shown in formula (b): In formula (b) and formula (c), the dotted line indicates the fusion position of the group; A1 to A8 are each independently selected from C, R A or N; The R A are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C3-C30 heteroarylthio, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R A are not connected or are connected by a chemical bond to form a ring; In formula (c), M2 represents O, S, NR 21 or CR 22 R 23 , where R 21 , R 22 , R 23 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and the R 22 , R 23 are not connected or are connected by a chemical bond to form a ring; The R A , R 21 , R 22 , R 23 The substituents in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 aryl, and C3-C30 heteroaryl.

3. The boron-containing compound according to claim 1 or 2, characterized in that, The boron-containing compound has the structure shown in any one of formula (II-1) to formula (III-4): In formulas (II-1) to (III-4), A1, A2, A3, and A4 are defined the same as in formula (b); X, M1, Y1 - Y4, Z5 - Z 10 are defined the same as in formula (I); Preferably, each X is independently selected from O, S or NR 11 , R 11 is as defined in formula (I); More preferably, the boron-containing compound has the structure shown in any one of formula (IV-1) to formula (IV-4): In Formula (IV-1) to Formula (IV-4), A1, A2, A3, and A4 are defined in the same manner as in Formula (b); M1, Y1-Y4, Z5-Z 10 , R 11 are defined in the same manner as in Formula (I); Preferably, at most one of Z5, Z6, and Z7 is selected from N, and / or at most one of Z8, Z9, and Z 10 is selected from N; preferably, each of Z5, Z6, Z7, Z8, Z9, and Z 10 is independently selected from CR Z ; Further preferably, R Z is independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; R Z is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

4. The boron-containing compound according to any one of claims 1 to 3, characterized in that, X is independently selected from O, S or NR 11 , The R 11 is independently selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; the R 11 is not connected to the adjacent ring structure or forms a ring by a chemical bond; Preferably, the R 11 is independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorene, benzofluorenyl, pyridyl, benzoxanthenyl, benzothioxanthenyl, benzonaphthofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; Optionally, the substituents substituted in the R 11 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, preferably selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, deuterated methyl, trifluoromethyl, deuterated tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl; More preferably, the R 11 is independently selected from any of the following groups:

5. The boron-containing compound according to any one of claims 1-4, characterized in that M1 is selected from O, S, NR 11 or CR 12 R 13 , wherein R 11 , R 12 and R 13 are defined the same as in formula (I). Preferably, M1 is selected from NR 11 or CR 12 R 13 . When M1 is selected from O or S; and / or 11 , R 12 and R 13 are each independently selected from any one of hydrogen, deuterium, C1-C6 alkyl, and C6-C12 aryl. More preferably, M1 is selected from O or S; and / or At most one of A1, A2, A3, A4 is selected from N, preferably, A1, A2, A3, A4 are each independently selected from CR A ; and / or At most one of Y1, Y2, Y3, Y4 is selected from N, and preferably, Y1, Y2, Y3, Y4 are each independently selected from CR Y ; Preferably, the R A , R Y are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the adjacent R A are not connected or are connected by a chemical bond to form a ring, and / or the adjacent R Y are not connected or are connected by a chemical bond to form a ring; More preferably, the R A , R Y are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Optionally, the substituents in the R A , R Y are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl, preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Further preferably, the R A , R Y are each independently selected from hydrogen, deuterium, halogen, cyano or any one of the following groups: Further preferably, the adjacent R A are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 carbocyclic ring, a substituted or unsubstituted C3-C20 heteroaromatic ring or a substituted or unsubstituted C6-C20 aromatic ring, and / or the adjacent R Y are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 carbocyclic ring, a substituted or unsubstituted C3-C20 heteroaromatic ring or a substituted or unsubstituted C6-C20 aromatic ring. Optionally, the substituents in the ring are selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, and C3-C8 cycloalkyl.

6. The boron-containing compound according to any one of claims 1-5, characterized in that, The boron-containing compound has the structure shown in any one of formula (V-1) to formula (VI-4): Formulas (V-1) to (VI-4), R A is defined the same as in formula (b), M1, R Y , R Z and X are defined the same as in formula (I), m is 0, 1, 2, 3 or 4, n is 0, 1, 2, 3 or 4, p is 0, 1, 2, 3, 4, 5 or 6; Preferably, M1 is selected from O or S; Preferably, R A , R Y are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C3-C20 heteroarylamino, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; the adjacent R A are not connected or are connected by a chemical bond to form a ring, and / or the adjacent R Y are not connected or are connected by a chemical bond to form a ring; Optionally, the substituents in the R A and R Y are each independently selected from any one or a combination of at least two of deuterium, fluorine, chlorine, bromine, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Preferably, R Z is independently preferably selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Preferably, each X is independently selected from O, S or NR 11 ; Said R 11 Each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Optionally, the substituents substituted in the R 11 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

7. The boron-containing compound according to any one of claims 1-6, characterized in that The boron-containing compound has the structure shown in any one of formula (V-1-1), formula (V-1-2), formula (V-3-1), formula (V-3-2), formula (VI-1-1), formula (VI-1-2), formula (VI-3-1), formula (VI-3-2): In Formula (V-1-1), Formula (V-1-2), Formula (V-3-1), Formula (V-3-2), Formula (VI-1-1), Formula (VI-1-2), Formula (VI-3-1), and Formula (VI-3-2), R A is defined in the same manner as in Formula (b), and M1, R Y , R Z , and R 11 are defined in the same manner as in Formula (I), m is 0, 1, 2, 3, or 4, m' is 0, 1, 2, or 3, n is 0, 1, 2, 3, or 4, p is 0, 1, 2, 3, 4, 5, or 6, and q is 0, 1, 2, 3, or 4; W represents a single bond, O or S; R 11a Each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R 11a are not connected or are connected by a chemical bond to form a ring; the substituents of the substituted R 11a each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, M1 is selected from O or S; Preferably, R A , R Y are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C12 heteroaryl. Optionally, the substituents in the R A , R Y are each independently selected from any one or a combination of at least two of deuterium, fluorine, chlorine, bromine, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; More preferably, the R A , R Y are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano or any one of the following groups: Preferably, R Z is independently preferably selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Preferably, R 11 is independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl. Optionally, the substituents of the substituted R 11 are independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl.

8. The boron-containing compound according to any one of claims 1-7, characterized in that, The boron-containing compound is selected from the group consisting of the following compounds:

9. Use of the boron-containing compound according to any one of claims 1-8 in the preparation of an organic electroluminescent device.

10. An organic electroluminescent device comprising a light-emitting layer, the light-emitting layer comprising a host material and a doping material, the doping material comprising the boron-containing compound according to any one of claims 1-8.

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