Organic boron-containing compound and application thereof

Abstract

The invention relates to an organic boron-containing compound and application thereof. The organic boron-containing compound provided by the invention has a structure as shown in a formula (I). When the organic boron-containing compound provided by the invention is applied to a luminescent layer of an organic electroluminescent device, the efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged. # imgabs0 #

Description

Technical Field

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

[0002] Organic electroluminescent displays are widely used in display and lighting fields such as mobile phones, televisions, computers, and cars due to their advantages such as self-luminescence, wide viewing angle, high contrast, fast response, low power consumption, lighter weight and power saving, and flexible display.

[0003] With the development of organic electroluminescent materials, red and green light-emitting materials have basically met the needs of displays. However, blue light-emitting materials, due to their wide bandgap characteristics and difficulty in charge injection, lag behind red and green light in terms of efficiency and lifespan. However, the performance of blue light, especially deep blue light, has a significant impact on improving display quality and reducing power consumption.

[0004] Blue light-emitting materials with commercial prospects require high efficiency and long life. Chinese patent CN103222082A discloses an aromatic vinyl compound used as a blue electroluminescent material, but this compound has poor heat resistance and is easily cracked during the sublimation process. For example, Chinese patent CN1394195A discloses a series of anthracene derivatives that can be used as OLED blue light materials, but the efficiency of such anthracene derivatives is low and cannot meet the current display requirements in actual applications. For another example, Chinese patent CN101018760A discloses a series of aromatic amine derivatives, but due to the imbalance between their hole transport performance and electron transport performance, their service life is still not ideal. Therefore, the research and development of high-efficiency and long-life blue light-emitting materials is of great significance to promoting the development of organic electroluminescent display and lighting technology. Summary of the Invention

[0005] In view of the various defects and deficiencies in the prior art, the object of the present invention is to provide an organic boron-containing compound as an organic electroluminescent blue light-emitting material (or doping material).

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

[0007]

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

[0009] X is independently selected from O, S, Se, NR X1 , CR X2R X3 or SiR X4 R X5 ;

[0010] R X1 、R X2 、R X3 、R X4 、R X5 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 X1 、R X2 、R X3 、R X4 、R X5 are each independently unconnected to or connected into a ring by a chemical bond with the adjacent ring structure; the R X2 、R X3 are unconnected to or connected into a ring by a chemical bond; the R X4 、R X5 are unconnected to or connected into a ring by a chemical bond;

[0011] wherein, at least one of the R X1 、R X2 、R X3 、R X4 、R X5 is a structure represented by formula (a); and / or at least one of ring A, ring C, and ring D is substituted by formula (a);

[0012] In formula (a), the expression of the ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure, and * represents the connection site of the group;

[0013] R1 and R2 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and R1 and R2 are unconnected to or connected into a ring by a chemical bond;

[0014] Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 are each independently selected from C, CR Z or N;

[0015] 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 the adjacent RZ are not connected or are connected by a chemical bond to form a ring;

[0016] Ring E is selected from any one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0017] The substituted substituents in the ring A, ring C, ring D, ring E, R1, R2, R Z , R X1 , R X2 , R X3 , R X4 , R X5 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, ester group, amino group, C1-C20 alkyl group, C1-C20 alkoxy group, C1-C20 alkylsilyl group, C2-C20 alkenyl group, C3-C20 cycloalkyl group, C2-C20 heterocycloalkyl group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C30 aryloxy group, C3-C30 heteroaryloxy group, C6-C30 arylthio group, C3-C30 heteroarylthio group, C6-C30 aryl group, C3-C30 heteroaryl group, or a combination of any one or at least two of them.

[0018] In the present invention, R X1 forming a ring by connecting with an adjacent ring structure through a chemical bond means that R X1 is not only connected to the N atom through a chemical bond, but also connected to an adjacent ring (such as ring A or ring D) through 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 can be understood that one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 is selected from C and is connected to formula (I), and the rest are each independently selected from CR Z or N.

[0020] 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.

[0021] 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.

[0022] In some preferred embodiments, each of ring A and ring C is independently a structure represented by formula (b) or formula (c):

[0023]

[0024] In formula (b) and formula (c), the dotted line represents the fusion position of the group;

[0025] A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from CR A or N;

[0026] Said 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 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, 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 aryl, substituted or unsubstituted C3-C30 heteroaryl. Adjacent said R A are not connected or are connected by a chemical bond to form a ring;

[0027] In formula (c), M represents O, S, NR M1 or CR M2 R M3 , wherein R M1 , R M2 , R M3 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. Said R M2 , R M3 are not connected or are connected by a chemical bond to form a ring;

[0028] Said R A , R M1 , R M2 , R M3The substituents in the formula 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.

[0029] In some preferred embodiments, ring D has the structure shown in formula (d):

[0030]

[0031] In formula (d), the dashed line represents the fusion position of the group;

[0032] U1, U2, and U3 are each independently selected from CR U or N;

[0033] The R U 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 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, 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 aryl, and substituted or unsubstituted C3-C30 heteroaryl. Adjacent R U are not connected or are connected by a chemical bond to form a ring;

[0034] The substituents in the R U 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. [[ID=X]] [[ID=Y]]

[0035] In some preferred embodiments, X is each independently selected from O, S, or NR X1; Preferably, at least one X is selected from NR X1 ; R X1 has the same definition as that in formula (I).

[0036] In some preferred embodiments, the organoboron-containing compound has a structure represented by any one of formulas (II-1) to (IV-5) as follows:

[0037]

[0038] In formulas (II-1) to (IV-5), A1, A2, A3, and A4 have the same definitions as those in formula (b); A 1’ , A 2’ , A 3’ , A 4’ have the same definitions as those of A1, A2, A3, and A4; M, A5, A6, A7, and A8 have the same definitions as those in formula (c); U1, U2, and U3 have the same definitions as those in formula (d); R X1 has the same definition as that in formula (I); R X1’ has the same definition as R X1 .

[0039] In some preferred embodiments, in formulas (II-1) to (IV-5), at least one of R A , R U , R X1 , R X1’ is a structure represented by formula (a). Preferably, at least one of R U , R X1 , R X1’ is a structure represented by formula (a). More preferably, U2 is selected from CR U and R U is selected from the structure represented by formula (a); or at least one of R X1 , R X1’ is a structure represented by formula (a). Further preferably, at least one of R X1 , R X1’ is a structure represented by formula (a).

[0040] In some preferred embodiments, the organoboron-containing compound has a structure represented by formula (II-3), formula (III-5), or formula (IV-5), more preferably a structure represented by formula (II-3) or formula (III-5).

[0041] In some preferred embodiments, formula (a) has a structure represented by any one of formulas (a-1) to (a-3), where * represents the connection site of the group:

[0042]

[0043] In Formulas (a-1) to (a-3), the definitions of R1, R2, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, and Ring E are the same as those in Formula (a).

[0044] In some preferred embodiments, Formula (a) has the structure shown in Formula (a-1) or Formula (a-2). Preferably, Formula (a) has the structure shown in Formula (a-2).

[0045] In some preferred embodiments, R1 and R2 are each independently selected from hydrogen, deuterium, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) 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-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, or any combination of at least two of them; preferably, R1 and R2 are each independently selected from any one or a combination of two of methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl; more preferably, R1 and R2 are each independently selected from methyl or phenyl.

[0046] In some preferred embodiments, Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from CR Z . A plurality (such as 2, 3, 4, 5, 6, 7, 8) of CR Z wherein the R Z are the same or different groups.

[0047] In some preferred embodiments, the number of CH in Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is 1-8 (such as 1, 2, 3, 4, 5, 6, 7, 8).

[0048] 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 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, said R Z Each independently selected from hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, any one or a combination of two; more preferably, said R Z Each independently selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl or phenyl.

[0049] In some more preferred embodiments, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 are all selected from CH.

[0050] In some preferred embodiments, in formulas (a-1) to (a-3), the ring E has the structure shown in formula (e):

[0051]

[0052] In formula (e), the dotted line indicates the fusion position of the groups;

[0053] E1, E2, E3, E4 each independently selected from CR E or N;

[0054] Said R E Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, any one, and adjacent said R E are not connected or connected by a chemical bond to form a ring;

[0055] Said R E The substituents in are each independently selected from deuterium, halogen, cyano, C1-C20 alkyl, C2-C20 alkenyl, C6-C30 aryl, C3-C30 heteroaryl, any one or a combination of at least two.

[0056] In some preferred embodiments, at most one (such as 0 or 1) of E1, E2, E3, E4 is selected from N, and the rest are independently selected from CR E. Preferably, E1, E2, E3, and E4 are each independently selected from CR E . A plurality (e.g., 2, 3, 4) of CR E The R E in is the same or different groups.

[0057] In some preferred embodiments, the number of CH in E1, E2, E3, and E4 is 1 - 4 (e.g., 1, 2, 3, 4).

[0058] In some preferred embodiments, the R E are each independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1 - C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C2 - C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6 - C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3 - C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, and adjacent R E are not connected or are connected by a chemical bond to form a ring.

[0059] In some preferred embodiments, the R E are each independently selected from any one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, n - propyl, isopropyl, tert - butyl, deuterated methyl, phenyl, naphthyl, pyridyl.

[0060] In some preferred embodiments, adjacent R E are not connected or are connected by a chemical bond to form a C1 - C6 (e.g., C2, C3, C4, C5, etc.) alkyl - substituted or unsubstituted C3 - C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) alicyclic ring, or a C1 - C6 (e.g., C2, C3, C4, C5, etc.) alkyl - substituted or unsubstituted C6 - C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring.

[0061] In some preferred embodiments, adjacent R E are not connected or are connected by a chemical bond to form a ring (e.g., forming etc., and the dashed line indicates the fusion position of the group).

[0062] In some more preferred embodiments, the ring E is selected from any of the following structures shown, and the dashed line indicates the fusion position of the group:

[0063]

[0065] In some preferred embodiments, the formula (a) has any of the following structures, where * represents the connection site of the group:

[0066]

[0067] In some preferred embodiments, the organoboron compound has any of the structures represented by formula (V-1) to formula (V-3):

[0068]

[0069] Wherein, the definitions of A1, A2, A3, and A4 are the same as those in formula (b); the definitions of A 1’ , A 2’ , A 3’ , A 4’ are the same as the definitions of A1, A2, A3, and A4; the definitions of M, A5, A6, A7, and A8 are the same as those in formula (c); the definitions of U1, U2, and U3 are the same as those in formula (d); the definition of R X1 is the same as the definition in formula (I); the definition of R X1’ is the same as the definition of R X1 ; the definitions of R1, R2, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, and ring E are the same as those in formula (a).

[0070] In some preferred embodiments, there is no connection or a chemical bond connection to form a ring between R X1 and A1. For example, it has the following structures:

[0071]

[0072] In formula (V-1-1) and formula (V-2-1), Y independently represents a single bond, O, S, or does not exist.

[0073] In some preferred embodiments, in formula (II-1) to formula (II-3), formula (V-1), and formula (V-1-1), at most one (for example, 0 or 1) of A1, A2, A3, and A4 is selected from N, and the rest are independently selected from CR A ; and / or at most one (for example, 0 or 1) of A 1’ , A 2’ , A 3’ , A 4’ is selected from N, and the rest are independently selected from CR A . Preferably, A1, A2, A3, A4, A1’ 、A 2’ 、A 3’ 、A 4’ Each independently selected from CR A 。Multiple (e.g., 2, 3, 4, 5, 6, 7, 8) CR A The R in A are the same or different groups. Further preferably, the number of CH in A1, A2, A3, A4, A 1’ 、A 2’ 、A 3’ 、A 4’ is 1 - 8 (e.g., 1, 2, 3, 4, 5, 6, 7, 8). Further preferably, A1, A4, A 1’ 、A 4’ are selected from CH, and A2, A3, A 2’ 、A 3’ Each independently selected from CR A 。

[0074] In some preferred embodiments, in formula (III-1) to formula (IV-5), formula (V-2), formula (V-3), formula (V-2-1), at most one (e.g., 0 or 1) of A1, A2, A3, A4 is selected from N, and the rest are independently selected from CR A ; and / or at most one (e.g., 0 or 1) of A5, A6, A7, A8 is selected from N, and the rest are independently selected from CR A 。Preferably, A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from CR A 。Multiple (e.g., 2, 3, 4, 5, 6, 7, 8) CR A The R in A are the same or different groups. Further preferably, the number of CH in A1, A2, A3, A4, A5, A6, A7, A8 is 1 - 8 (e.g., 1, 2, 3, 4, 5, 6, 7, 8). Further preferably, A1, A4, A5, A8 are selected from CH, and A2, A3, A6, A7 are each independently selected from CR A 。

[0075] In some preferred embodiments, in formula (II-1) to formula (IV-5), formula (V-1) to formula (V-3), formula (V-1-1), formula (V-2-1), at most one (e.g., 0 or 1) of U1, U2, U3 is selected from N, and the rest are independently selected from CR U 。Preferably, U1, U2, U3 are each independently selected from CR U 。Multiple (e.g., 2 or 3) CR U The R in Uare the same or different groups. Further preferably, the number of CH in U1, U2, and U3 is 1 - 3 (e.g., 1, 2, 3). Further preferably, U1 and U3 are selected from CH, and U2 is selected from CR U .

[0076] In some preferred embodiments, the R A , R U each independently selected from hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, substituted or unsubstituted C1 - C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C1 - C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1 - C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C2 - C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3 - C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2 - C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6 - C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3 - C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6 - C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3 - C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, any one of which, adjacent R A are not connected or connected by a chemical bond to form a ring, and adjacent R U are not connected or connected by a chemical bond to form a ring.

[0077] In some preferred embodiments, the R A , R UEach independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0078] In some preferred embodiments, the R A , R U The substituents in are each independently selected from 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 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, or any one or a combination of at least two of them.

[0079] In some preferred embodiments, the R A , R U The substituents in are each independently selected from deuterium, fluorine, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, etc.), C6-C10 aryl (such as phenyl, etc.), deuterated C1-C6 alkyl (such as deuterated methyl, deuterated ethyl or deuterated tert-butyl, etc.). In some embodiments, the R A , R U The substituents in are each independently selected from deuterated methyl.

[0080] In some preferred embodiments, the R A , R U Each independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, * represents the connection site of the group: *-CH3, *-CD3, *-CF3,

[0081] In some embodiments, the adjacent R A Do not connect or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) alicyclic ring, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, 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 embodiments, adjacent R's U are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) alicyclic ring, a substituted or unsubstituted C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, or a substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring.

[0083] In some embodiments, the substituents of the above-mentioned rings 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-C6 (such as C2, C3, C4, C5, etc.) alkyl, C3-C8 (such as C4, C5, C6, C7, etc.) cycloalkyl, C6-C12 (such as C6, C9, C10, etc.) aryl, and C3-C12 (such as C3, C4, C5, C6, C9, C10, etc.) heteroaryl.

[0084] In some preferred embodiments, adjacent R's A are not connected or are connected by a chemical bond to form a ring, and / or adjacent R's U are not connected or are connected by a chemical bond to form a ring (such as forming etc., the dotted line indicates the fusion position of the group). Among them, the ring is optionally substituted by any one or more substituents selected from deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0085] In some preferred embodiments, in formulas (III-1) to (IV-5), formula (V-2), formula (V-3), and formula (V-2-1), M represents O or S.

[0086] In some preferred embodiments, in formulas (III-1) to (IV-5), formula (V-2), formula (V-3), and formula (V-2-1), M represents NR M1 or CR M2 R M3 , wherein the definitions of R M1 , R M2 , and R M3 are the same as those in formula (c).

[0087] In some preferred embodiments, when M is selected from NR M1 or CR M2 R M3 , the RM1 , R M2 , R M3 Each independently selected from hydrogen, deuterium, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, etc.), C6-C12 aryl (such as phenyl or naphthyl, etc.) of any one.

[0088] In some preferred embodiments, in formula (II-1) to formula (IV-5), formula (V-1) to formula (V-3), formula (V-1-1), formula (V-2-1), R X1 , R X1’ Each independently selected from 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 of any one; the R X1 , R X1’ Each independently not connected to the adjacent ring structure or connected by a chemical bond to form a ring.

[0089] In some preferred embodiments, the substituents in the R X1 , R X1’ Each independently selected from 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 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 of any one or a combination of at least two.

[0090] In some preferred embodiments, the R X1 , R X1’Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, benzoxanthenyl, benzothioxanthenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl.

[0091] In some preferred embodiments, the R X1 , R X1’ The substituents in the substitution are each independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl.

[0092] In some preferred embodiments, the substituent in R X1 or R X1’ is each independently selected from deuterated methyl (e.g., *-CD3), deuterated tert-butyl (e.g., ), tert-butyl substituted with phenyl isopropyl substituted with phenyl deuterated phenyl 1,2,3,4-tetrahydronaphthyl substituted with methyl (e.g., ) or a combination of any one or two of them.

[0093] In some preferred embodiments, the R X1 , R X1’ are each independently selected from any one of the following groups, * represents the connection site of the group:

[0094]

[0095] In some embodiments, the organoboron compound of the present invention has any one of the following structures:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] In a second aspect, the present invention provides the use of the above-mentioned organoboron compound in the preparation of an organic electroluminescent device.

[0116] According to some preferred embodiments of the present invention, the organoboron compound is used as a doping material (also known as a dopant or fluorescent dye or dye or luminescent material) in the light-emitting layer of the organic electroluminescent device.

[0117] In some embodiments, the doping concentration of the doping material is 1 wt% to 20 wt% (such as 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt% or 19 wt%) relative to the host material in the light-emitting layer, preferably 1 wt% to 15 wt%, more preferably 2 wt% to 10 wt%.

[0118] In a third aspect, the present invention provides an organic electroluminescent device, which includes a light-emitting layer, the light-emitting layer includes a host material and a doping material, and the doping material contains the above-mentioned organoboron compound of the present invention.

[0119] According to some preferred embodiments of the present invention, the organic electroluminescent device includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In some embodiments, the light-emitting layer includes a doping material.

[0120] According to some preferred embodiments of the present invention, the organic electroluminescent device further includes 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.

[0121] In a fourth aspect, the present invention provides a display component / device, which includes the organic 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.

[0122] The OLED device prepared by using the organic 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.

[0123] The above-mentioned organic boron-containing compound of the present invention has excellent performance as a doping material in the light-emitting layer of an organic electroluminescent device. It is speculated that the possible reasons are as follows: The organic compound provided by the present invention has the structure shown in formula (I). By introducing the bulky group of formula (a), the overall molecular conjugation is larger. When it is applied to the light-emitting layer of an organic electroluminescent device, the efficiency and lifespan of the device can be improved. Specific Embodiments

[0124] 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 used 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 appended claims.

[0125] Definition of Substituent Terms

[0126] 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.

[0127] 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 of heterocycloalkyl are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms of alicyclic heterocycles are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0128] In the present invention, the expression of the ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure.

[0129] In the present invention, both "-*" and "*" represent the connection sites of groups.

[0130] In the present invention, "each independently" means that when the subject has multiple ones, they can be the same or different from each other.

[0131] In the present invention, the expression of Ca-Cb represents that the group has a carbon atom number of a - b. Without special instructions, the carbon atom number does not include the carbon atom numbers of substituents.

[0132] 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.

[0133] In the present invention, 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.

[0134] In the present invention, the C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0135] In the present invention, the C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0136] In the present invention, the C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0137] 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. When there are at least 2 phenyl groups, the phenyl groups are connected by single bonds. Exemplarily, but 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, but not limited to: naphthyl, anthracenyl, phenanthrenyl, 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, and so on. 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, binaphthyl, etc.

[0138] In the present invention, unless otherwise specified, the C6-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes monocyclic heteroaryl groups or polycyclic heteroaryl groups. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl groups, heteroaryl groups, etc.), the heteroaryl group and other groups are connected by single bonds. Exemplarily, but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The polycyclic heteroaryl group means that the molecule contains 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, but 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.

[0139] 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, and exemplary include but are 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, and exemplary include but are not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0140] 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.

[0141] 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.

[0142] In the present invention, the C3-C10 alicyclic ring includes a saturated alicyclic ring or an unsaturated alicyclic ring, preferably a saturated alicyclic ring. The C2-C10 heteroalicyclic ring includes a saturated heteroalicyclic ring or an unsaturated heteroalicyclic ring, preferably a saturated heteroalicyclic ring, and can be understood as a ring structure formed by replacing at least 1 ring carbon atom in the alicyclic ring with a heteroatom (such as N, S, O, etc.).

[0143] In the present invention, the C1-C20 alkyl group, preferably a C1-C16 alkyl group, more preferably a C1-C10 alkyl group, and exemplary include but are 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.

[0144] In the present invention, specific examples of the C1-C20 alkoxy group can be monovalent groups obtained by connecting the examples of the above-mentioned alkyl groups with O.

[0145] 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-mentioned alkyl groups, and exemplary include but are not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0146] In the present invention, the C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0147] In the present invention, specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0148] In the present invention, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, contains at least one C=C, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0149] In the present invention, the "substituted or unsubstituted" group may be substituted with one or more substituents. When there are multiple substituents (at least two), they may be the same or different. The same expressions used above have the same meaning. Unless otherwise specified, the range of substituents is as described in the present invention and will not be further described.

[0150] It should be understood that when describing a molecular fragment 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 an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered equivalent.

[0151] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms, such as carbon and nitrogen, may also be replaced by their other stable isotopes. The replacement of compounds with other stable isotopes may be preferred because it enhances device efficiency and stability.

[0152] In the compounds described herein, multiple substitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on the structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0153] Among the compounds referred to in the present invention, unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring, adjacent substituents in the said compounds cannot be linked to form a ring. Among the compounds referred to in the present invention, adjacent substituents can optionally be linked to form a ring, which includes both the case where adjacent substituents can be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be linked to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this expression, 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.

[0154] The materials for specific layers described in the present invention for use in organic light-emitting devices can be used in combination with various other materials present in the device. The combinations of these materials are 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.

[0155] The materials described in the present invention as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the said devices. 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 combinations of these materials are described in detail in paragraphs 0080 - 0,101 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.

[0156] 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 liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimators, 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 evaporation coaters from Nanjing Institute of Microelectronics Technology, optical test systems and lifetime test systems from Suzhou Fosida, ellipsometers from Wuhan Yiguang Technology, etc.) by methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and test methods 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.

[0157] There is no limitation on the preparation method of the compounds of the present invention. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0158] Example 1: Synthesis of Compound I-8

[0159]

[0160]

[0161] (1-1) Synthesis of Intermediate S1-1:

[0162] Under nitrogen protection, raw materials M1-1 (69.02 g), M1-2 (94.75 g), Pd(PPh3)4 (6.93 g), anhydrous K2CO3 (82.92 g), dioxane (400 mL) and water (40 mL) were added to a dry three-necked reaction flask, and the temperature was raised to 100 °C for reaction for 7 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 three times, the organic phase was collected, purified by column chromatography, recrystallized, and dried to obtain Intermediate S1-1 (81.32 g, yield 72.5%).

[0163] (1-2) Synthesis of Intermediate S1-2:

[0164] Under nitrogen protection, Intermediate S1-1 (74.79 g) and methanesulfonic acid (56.67 g) were added to a dry three-necked reaction flask, and the temperature was raised to 55 °C for reaction for 5 h. After the reaction was completed, the temperature was lowered to 0 °C, water (100 mL) was added, filtered, extracted with dichloromethane (100 mL) three times, the organic phases were combined, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain Intermediate S1-2 (28.81 g, yield 42.1%).

[0165] Synthesis of Intermediate S1-3 (1-3):

[0166] Under nitrogen protection, add Intermediate S1-2 (27.36 g) and ethylene glycol (400 mL) to a dry three-necked reaction flask. After stirring and dissolving, add hydrazine hydrate (120 mL) and KOH (11.22 g), and heat up to 190 °C for reaction for 8 h. After the reaction is completed, cool down to 0 °C, add water (100 mL), filter, extract three times with dichloromethane (100 mL), combine the organic phases, dry with anhydrous magnesium sulfate, concentrate under reduced pressure, purify by column chromatography, and recrystallize to obtain Intermediate S1-3 (20.92 g, yield 79.7%).

[0167] Synthesis of Intermediate S1-4 (1-4):

[0168] Under nitrogen protection, add Intermediate S1-3 (16.40 g), potassium tert-butoxide (16.83 g) and DMF (400 mL) to a dry three-necked reaction flask. Stir at 0 °C for 20 min, then heat up to room temperature, add methyl iodide (10 mL), and react for 3 h. After the reaction is completed, filter, extract three times with dichloromethane (50 mL) and water (50 mL), dry with anhydrous magnesium sulfate, concentrate under reduced pressure, purify by column chromatography, and recrystallize to obtain Intermediate S1-4 (15.04 g, yield 84.5%).

[0169] Synthesis of Intermediate S1-5 (1-5):

[0170] Under nitrogen protection, add Intermediate S1-4 (14.24 g), raw material M1-3 (6.24 g), Pd(PPh3)4 (0.92 g), anhydrous K2CO3 (11.06 g), dioxane (200 mL) and water (20 mL) to a dry three-necked reaction flask. Heat up to 90 °C for reaction for 4 h. After the reaction is completed, cool down to room temperature, wash with water and separate the layers. Extract the aqueous phase three times with toluene, collect the organic phase, purify by column chromatography, recrystallize, and dry to obtain Intermediate S1-5 (12.35 g, yield 79.6%).

[0171] Synthesis of Intermediate S1-6 (1-6):

[0172] Under nitrogen protection, add Intermediate S1-5 (11.64 g), Pd(OAc)2 (1.68 g), tricyclohexylphosphine (4.21 g), cesium carbonate (29.32 g) and anhydrous o-xylene (300 mL) to a dry three-necked reaction flask. Heat up to 80 °C for reaction for 10 h. After the reaction is completed, cool down to room temperature, filter, add toluene (200 mL) to dissolve, concentrate under reduced pressure, purify by column chromatography, and recrystallize to obtain Intermediate S1-6 (8.01 g, yield 75.9%). (1-7) Synthesis of Intermediate S1-7:

[0173] Under nitrogen protection, add intermediate S1-6 (7.04 g), raw material M1-4 (2.98 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. Heat the mixture to 100 °C and react for 2 h. After the reaction solution is cooled, add water (100 mL), wash with water and concentrate. Purify by column chromatography, recrystallize, and dry to obtain intermediate S1-7 (6.63 g, yield 71.2%).

[0174] (1-8) Synthesis of Intermediate S1-8:

[0175] Under nitrogen protection, add raw material M1-5 (8.40 g), raw material M1-6 (8.44 g), sodium tert-butoxide (5.77 g), Pd2(dba)3 (0.55 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.14 g) and toluene (200 mL) into a dry three-necked reaction flask. Heat the mixture to 100 °C and react for 2 h. After the reaction solution is cooled, add water (100 mL), wash with water and concentrate. Purify by column chromatography, recrystallize, and dry to obtain intermediate S1-8 (11.80 g, yield 81.7%).

[0176] (1-9) Synthesis of Intermediate S1-9:

[0177] Under nitrogen protection, add intermediate S1-7 (9.31 g), intermediate S1-8 (9.62 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. Heat the mixture to 100 °C and react for 2 h. After the reaction solution is cooled, add water (100 mL), wash with water and concentrate. Purify by column chromatography, recrystallize, and dry to obtain intermediate S1-9 (12.65 g, yield 69.5%).

[0178] (1-10) Synthesis of Compound I-8:

[0179] Under nitrogen protection, add intermediate S1-9 (9.11 g) and tert-butylbenzene (120 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 warm up to 60 °C and react for 3 h, stop heating. After cooling down to -78 °C, add boron tribromide (2.4 mL), restore to room temperature and react for 6 h, then cool down to 0 °C and dropwise add N,N-diisopropylethylamine (7.0 mL) and react at 120 °C for 10 h. After the reaction is completed, cool to room temperature, wash with water, separate the layers, dry and concentrate, purify by column chromatography, and recrystallize to obtain compound I-8 (1.87 g, yield 21.1%).

[0180] MS (m / e) of compound I-8: 884.33; 1 1H NMR (400 MHz, CDCl3): δ 8.29 - 8.19 (m, 2H), 8.18 - 8.12 (m, 1H), 8.06 - 7.96 (m, 2H), 7.72 - 7.63 (m, 2H), 7.62 - 7.47 (m, 3H), 7.42 (d, 1H), 7.35 (d, 2H), 7.30 - 7.18 (m, 4H), 7.08 - 6.98 (m, 4H), 6.91 - 6.85 (m, 2H), 1.70 (s, 6H), 1.38 - 1.32 (m, 36H).

[0181] Example 2: Synthesis of compound I-13

[0182]

[0183] (2-1) Synthesis of intermediate S2-7:

[0184] The synthesis route of intermediate S2-7 is the same as that of intermediate S1-7. Just replace raw material M1-2 with raw material M2-1 to obtain intermediate S2-7. (2-2) Synthesis of intermediate S2-8:

[0185] Under nitrogen protection, add raw material M2-2 (10.56 g), raw material M2-3 (11.17 g), cesium carbonate (26.07 g) and DMF (200 mL) to a dry three-necked reaction flask, warm up to 80 °C and react for 6 h. After the reaction is completed, cool down to room temperature, dropwise add water to crystallize, filter, dry, and wash with ethanol to obtain intermediate S2-8 (11.16 g, yield 53.3%).

[0186] (2-3) Synthesis of compound I-13:

[0187] The synthetic route of compound I-13 is the same as that of compound I-8. By simply replacing intermediate S1-8 with intermediate S2-8 and intermediate S1-7 with intermediate S2-7, compound I-13 can be obtained.

[0188] MS (m / e) of compound I-13: 882.64; 1 1H NMR (400 MHz, CDCl3): δ 8.48 (d, 1H), 8.33 (d, 1H), 8.25 - 8.12 (m, 3H), 8.06 - 8.00 (m, 2H), 7.93 (d, 1H), 7.67 - 7.46 (m, 5H), 7.37 - 7.32 (m, 2H), 7.30 - 7.17 (m, 4H), 7.08 (d, 1H), 7.00 (d, 1H), 1.68 (s, 6H), 1.38 - 1.32 (m, 36H).

[0189] Example 3: Synthesis of compound I-38

[0190]

[0191] (3-1) Synthesis of raw material M3-1:

[0192] The synthetic route of raw material M3-1 is the same as that of intermediate S1-7. By simply replacing intermediate S1-6 with raw material M3-1a, raw material M3-1 can be obtained. (3-2) Synthesis of compound I-38:

[0193] The synthetic route of compound I-38 is the same as that of compound I-8. By simply replacing raw material M1-6 with raw material M3-1, compound I-38 can be obtained.

[0194] MS (m / e) of compound I-38: 984.12; 1 1H NMR (400 MHz, CDCl3): δ 8.29 - 8.12 (m, 6H), 8.06 - 7.89 (m, 3H), 7.77 - 7.63 (m, 3H), 7.62 - 7.45 (m, 6H), 7.42 (d, 1H), 7.37 - 7.31 (m, 3H), 7.22 (dd, 2H), 7.00 (d, 2H), 6.91 - 6.84 (m, 2H), 1.70 (s, 6H), 1.35 (d, 27H).

[0195] Example 4: Synthesis of compound I-82

[0196]

[0197] The synthetic route of Compound I-82 is the same as that of Compound I-8. By simply replacing raw material M1-3 with raw material M4-1 and intermediate S1-7 with intermediate S4-3, Compound I-82 can be obtained.

[0198] MS (m / e) of Compound I-82: 934.76; 1 HNMR (400 MHz, CDCl3): δ 9.13 - 9.07 (m, 2H), 8.26 (d, 1H), 8.06 - 7.98 (m, 4H), 7.71 (d, 1H), 7.65 (dd, 1H), 7.56 - 7.48 (m, 3H), 7.43 (d, 1H), 7.35 (d, 2H), 7.30 - 7.18 (m, 4H), 7.08 - 6.98 (m, 4H), 6.91 - 6.85 (m, 2H), 1.70 (s, 6H), 1.38 - 1.32 (m, 36H).

[0199] Example 5: Synthesis of Compound I-140

[0200]

[0201] The synthetic route of Compound I-140 is the same as that of Compound I-8. By simply replacing raw material M1-2 with raw material M5-1, raw material M1-4 with raw material M5-2, and intermediate S1-7 with intermediate S5-7, Compound I-140 can be obtained.

[0202] MS (m / e) of Compound I-140: 924.31; 1 HNMR (400 MHz, CDCl3): δ 8.43 - 8.37 (m, 1H), 8.28 - 8.19 (m, 2H), 8.06 - 7.97 (m, 2H), 7.71 - 7.64 (m, 2H), 7.59 - 7.47 (m, 5H), 7.39 - 7.33 (m, 2H), 7.31 - 7.24 (m, 3H), 7.21 (dd, 1H), 7.08 - 7.02 (m, 2H), 7.00 (d, 1H), 6.91 - 6.85 (m, 2H), 1.68 (s, 6H), 1.38 - 1.32 (m, 36H).

[0203] Example 6: Synthesis of Compound I-147

[0204]

[0205] The synthetic route of Compound I-147 is the same as that of Compound I-8. By simply replacing raw material M1-4 with raw material M6-1, raw material M1-6 with raw material M6-2, and intermediate S1-7 with intermediate S6-1, Compound I-147 can be obtained.

[0206] MS (m / e) of Compound I-147: 996.72; 1 HNMR (400 MHz, CDCl3): δ 8.29 - 8.19 (m, 2H), 8.18 - 8.12 (m, 1H), 8.06 - 7.96 (m, 2H), 7.82 (d, 1H), 7.76 - 7.69 (m, 2H), 7.65 (dd, 1H), 7.62 - 7.47 (m, 3H), 7.43 (d, 1H), 7.36 (dd, 1H), 7.32 (d, 1H), 7.24 - 7.18 (m, 2H), 7.02 - 6.93 (m, 3H), 6.91 - 6.85 (m, 2H), 1.70 (s, 6H), 1.35 (t, 45H).

[0207] Example 7: Synthesis of Compound I-218

[0208]

[0209] (7-1) Synthesis of raw material M7-1:

[0210] The synthetic route of raw material M7-1 is the same as that of intermediate S1-7. By simply replacing raw material M1-4 with raw material M7-1a, and intermediate S1-6 with raw material M7-1b, raw material M7-1 can be obtained.

[0211] (7-2) Synthesis of Compound I-218:

[0212] The synthetic route of Compound I-218 is the same as that of Compound I-8. By simply replacing raw material M1-6 with intermediate S1-7, and intermediate S1-7 with raw material M7-1, Compound I-218 can be obtained.

[0213] MS (m / e) of Compound I-218: 1056.47; 1HNMR(400MHz, CDCl3): δ 8.29 - 8.19 (m, 2H), 8.17 - 8.13 (m, 1H), 8.06 - 7.96 (m, 2H), 7.71 - 7.63 (m, 3H), 7.62 - 7.47 (m, 7H), 7.42 (d, 1H), 7.38 - 7.33 (m, 3H), 7.31 - 7.19 (m, 4H), 7.00 (d, 1H), 6.91 - 6.85 (m, 2H), 1.70 (s, 6H), 1.38 - 1.32 (m, 45H).

[0214] Example 8: Synthesis of Compound I - 286

[0215]

[0216] The synthetic route of Compound I - 286 is the same as that of Compound I - 8, except that raw material M1 - 3 is replaced with raw material M8 - 1, raw material M1 - 4 is replaced with M6 - 1, raw material M1 - 6 is replaced with M8 - 2, and intermediate S1 - 7 is replaced with intermediate S8 - 3, then Compound I - 286 can be obtained.

[0217] MS (m / e) of Compound I - 286: 1044.85; 1 HNMR(400MHz, CDCl3): δ 8.47 (d, 1H), 8.26 (d, 1H), 8.18 - 8.12 (m, 1H), 8.06 - 7.95 (m, 4H), 7.82 (d, 1H), 7.73 (d, 1H), 7.65 (dd, 1H), 7.59 - 7.41 (m, 5H), 7.36 (dd, 1H), 7.32 (d, 1H), 7.22 (dd, 1H), 7.16 - 7.13 (m, 1H), 7.00 (d, 1H), 6.98 - 6.93 (m, 2H), 6.91 - 6.85 (m, 2H), 1.84 - 1.73 (m, 2H), 1.70 (s, 6H), 1.68 - 1.57 (m, 2H), 1.38 - 1.28 (m, 39H).

[0218] Example 9: Synthesis of Compound I - 360

[0219] [[ID=2,1]]

[0220] (9 - 1) Synthesis of Raw Material M9 - 2:

[0221] The synthetic route of raw material M9 - 2 is the same as that of intermediate S1 - 7, except that raw material M1 - 4 is replaced with raw material M9 - 2a, and intermediate S1 - 6 is replaced with raw material M9 - 2b, then raw material M9 - 2 can be obtained.

[0222] (9-2) Synthesis of Compound I-360:

[0223] The synthetic route of Compound I-360 is the same as that of Compound I-8, except that raw material M1-3 is replaced with raw material M9-1, raw material M1-6 is replaced with intermediate S9-3, and intermediate S1-7 is replaced with raw material M9-2, then Compound I-360 can be obtained.

[0224] MS (m / e) of Compound I-360: 1142.39; 1 HNMR (400 MHz, CDCl3): δ 8.28 - 8.21 (m, 2H), 8.17 - 8.12 (m, 1H), 8.06 - 7.93 (m, 4H), 7.82 (d, 1H), 7.76 - 7.64 (m, 3H), 7.59 - 7.34 (m, 17H), 7.32 (d, 1H), 7.21 (dd, 1H), 7.00 (d, 1H), 6.92 - 6.87 (m, 2H), 1.70 (s, 6H), 1.38 - 1.32 (m, 36H).

[0225] The present invention exemplarily provides the specific synthesis methods of the above several compounds. For other compounds without specific synthesis methods, they are also prepared by similar methods, and can be obtained only by replacing the 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.

[0226] Device Example 1

[0227] Clean a glass substrate having 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, and then mount the substrate on a substrate holder and load it into a vacuum chamber.

[0228] At a vacuum of about 10 -8 Torr, thermally evaporate successively on the ITO anode at a rate of While evaporating Compound 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-evaporate Compound BH as the blue light host and Compound I-8 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, the compounds ET and lithium 8-hydroxyquinolate (Liq) are co-evaporated (weight ratio 50:50) as the electron transport layer (ETL), with a thickness of Finally, lithium 8-hydroxyquinolate (Liq) with a thickness of is evaporated as the electron injection layer (EIL), and aluminum is evaporated as the cathode. Then the device is transferred back to the glove box and encapsulated with a glass cover to complete the device.

[0229] Device Examples 2 to 9, Device Comparative Example 1

[0230] The difference between it and Device Example 1 is only that the doping materials of the light-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.

[0231] The molecular structural formulas of the related materials are shown as follows:

[0232]

[0233] Table 1 lists the voltage (V), external quantum efficiency (EQE), and lifetime (h) measured under the condition of a current density of 10 mA / cm 2 For better presentation of the data comparison, the voltage, external quantum efficiency, and lifetime of Device Comparative Example 1 are respectively set to 100%. The voltage, efficiency, and lifetime data of Device Examples 1 to 9 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.

[0234] Table 1

[0235] Device Doped material Voltage (V) EQE Lifetime (h) Device Example 1 I-8 94％ 113％ 116％ Device Example 2 I-13 93％ 111％ 114％ Device Example 3 I-38 93％ 117％ 120％ Device Example 4 I-82 92％ 119％ 122％ Device Example 5 I-140 93％ 118％ 127％ Device Example 6 I-147 92％ 123％ 132％ Device Example 7 I-218 93％ 122％ 130％ Device Example 8 I-286 91％ 124％ 136％ Device Example 9 I-360 91％ 125％ 134％ Device Comparative Example 1 Ref-1 100％ 100％ 100％

[0236] As shown in Table 1, at a current density of 10 mA / cm 2 Under the current density, compared with Device Comparative Example 1, for Device Examples 1 to 9, the voltage can be reduced by 6 - 9%, the external quantum efficiency can be increased by 11% - 25%, and the device lifetime can be extended, with the maximum extension of 36%. The above data indicate that the device prepared with the organoboron compound provided by the present invention has a lower driving voltage, a higher current efficiency, and a longer lifetime.

[0237] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be obvious to those skilled in the art, the claimed invention may include variations of the specific embodiments 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 regarding why the present invention works are not intended to be restrictive.

Claims

1. An organoboron compound having a structure represented by formula (I): In formula (I), ring A, ring C, and ring D are each independently selected from any one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring; X is independently selected from O, S, Se, NR X1 , CR X2 R X3 or SiR X4 R X5 ; R X1 、R X2 、R X3 、R X4 、R X5 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 X1 、R X2 、R X3 、R X4 、R X5 are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; the R X2 、R X3 are not connected to each other or connected into a ring through a chemical bond; the R X4 、R X5 are not connected to each other or connected into a ring through a chemical bond; Among them, The R X1 , R X2 , R X3 , R X4 , R X5 at least one of them has the structure shown in formula (a); and / or at least one of ring A, ring C, and ring D is substituted by formula (a); In formula (a), the expression of the ring structure with a "—" drawn across it indicates the bonding site at any bond-forming position on the ring structure, and * represents the bonding site of the group; R1 and R2 are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, and R1 and R2 are not connected or are connected by a chemical bond to form a ring; Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 are each independently selected from C, CR Z or N; 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; Ring E is selected from any one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring; The substituents substituted in the ring A, ring C, ring D, ring E, R1, R2, R Z , R X1 , R X2 , R X3 , R X4 , R X5 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxy, ester group, 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 organic boron-containing compound according to claim 1, characterized in that, Ring A and ring C are each independently a structure represented by formula (b) or formula (c): In formula (b) and formula (c), the dotted line represents the fusion position of the group; A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from C, R A or N; 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 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, 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 aryl, substituted or unsubstituted C3-C30 heteroaryl, and any two adjacent R A are not connected or are connected by a chemical bond to form a ring; In formula (c), M represents O, S, NR M1 or CR M2 R M3 , where R M1 , R M2 , R M3 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 M2 , R M3 are not connected or are connected by a chemical bond to form a ring; The R A , R M1 , R M2 , R M3 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; Ring D is a structure represented by formula (d): In formula (d), the dotted line represents the fusion position of the group; U1, U2, U3 are each independently selected from CR U or N; The R U 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 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, 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 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and adjacent R U are not connected or are connected by a chemical bond to form a ring; The R U 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 organoboron compound according to claim 1 or 2, characterized in that, X is independently selected from O, S or NR X1 , R X1 is as defined in formula (I), Preferably, the organoboron compound has a structure represented by any one of the following formulas (II-1) to (IV-5): In formulas (II-1) to (IV-5), A1, A2, A3, and A4 are defined the same as in formula (b); A 1’ , A 2’ , A 3’ , A 4’ are defined the same as A1, A2, A3, and A4; M, A5, A6, A7, and A8 are defined the same as in formula (c); U1, U2, and U3 are defined the same as in formula (d); R X1 is defined the same as in formula (I); R X1’ is defined the same as R X1 . Preferably, in formulas (II-1) to (IV-5), R A , R U , R X1 , R X1’ at least one of them has the structure shown in formula (a); more preferably, R U , R X1 , R X1’ at least one of them has the structure shown in formula (a); further preferably, R X1 , R X1’ at least one of them has the structure shown in formula (a).

4. The organoboron compound according to any one of claims 1-3, characterized in that, The organoboron compound has a structure represented by any one of formulas (V-1) to (V-3): Among them, the definitions of A1, A2, A3, and A4 are the same as those in formula (b); A 1’ , A 2’ , A 3’ , A 4’ have the same definitions as A1, A2, A3, and A4; the definitions of M, A5, A6, A7, and A8 are the same as those in formula (c); the definitions of U1, U2, and U3 are the same as those in formula (d); the definition of R X1 is the same as that in formula (I); the definition of R X1’ is the same as the definition of R X1 ; the definitions of R1, R2, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, and ring E are the same as those in formula (a).

5. The organoboron compound according to claim 3 or 4, characterized in that, In Formula (II-1) to Formula (II-3) and Formula (V-1), at most one of A1, A2, A3, and A4 is selected from N; and / or A 1’ , A 2’ , A 3’ , A 4’ at most one of them is selected from N; preferably, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ , A 4’ are each independently selected from CR A ; In Formula (III-1) to Formula (IV-5), Formula (V-2) and Formula (V-3), at most one of A1, A2, A3, A4 is selected from N; and / or at most one of A5, A6, A7, A8 is selected from N; preferably, A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from CR A ; In formulas (II-1) to (IV-5) and formulas (V-1) to (V-3), at most one of U1, U2, and U3 is selected from N; preferably, U1, U2, and U3 are each independently selected from CR U ; Preferably, the R A , R U 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, and adjacent R A are not connected or are connected by a chemical bond to form a ring, and adjacent R U are not connected or are connected by a chemical bond to form a ring; More preferably, the R A , R U 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 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 U are each independently selected from 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; More preferably, the R A , R U 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 alicyclic ring, a substituted or unsubstituted C3-C20 heteroaromatic ring or a substituted or unsubstituted C6-C20 aromatic ring, and / or the adjacent R U are not connected or are connected by a chemical bond to form a substituted or unsubstituted C3-C10 alicyclic ring, a substituted or unsubstituted C3-C20 heteroaromatic ring or a substituted or unsubstituted C6-C20 aromatic ring; optionally, the substituents on the ring are each independently 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; In Formulas (III-1) to (IV-5), Formula (V-2), and Formula (V-3), M represents O, S, NR M1 or CR M2 R M3 , R M1 , R M2 , R M3 are defined the same as in Formula (c); preferably, M is selected from NR M1 or CR M2 R M3 When, the R M1 , R M2 , R M3 are each independently selected from any one of hydrogen, deuterium, C1-C6 alkyl, and C6-C12 aryl; preferably, M represents O or S.

6. The organoboron compound according to claim 4 or 5, characterized in that, In formulas (II-1) to (IV-5) and formulas (V-1) to (V-3), R X1 , R X1’ are each independently selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; the R X1 , R X1’ are each independently not connected to the adjacent ring structure or connected into a ring through a chemical bond; optionally, the substituents in the R X1 , R X1’ 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; Preferably, the R X1 , R X1’ are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, benzoxanthenyl, benzothioxanthenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; optionally, the substituents in the R X1 , R X1’ are each independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl; More preferably, the R X1 , R X1’ are each independently selected from any of the following groups:

7. The organoboron compound according to any one of claims 1-6, characterized in that, Formula (a) has a structure represented by any one of formulas (a-1) to (a-3): In formulas (a-1) to (a-3), the definitions of R1, R2, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, and ring E are the same as those in formula (a); Preferably, R1 and R2 are each independently selected from any one of hydrogen, deuterium, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C6-C20 aryl group, and a C3-C20 heteroaryl group, or a combination of at least two of them, preferably selected from any one of or a combination of two of methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, and pyridyl, and more preferably selected from methyl or phenyl; Preferably, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 are each independently selected from CR Z ; The R Z are each 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; preferably selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl; more preferably selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl, or phenyl.

8. The organic boron-containing compound according to any one of claims 1-7, characterized in that, Ring E is a structure represented by formula (e): In formula (e), the dotted line represents the fusion position of the group; E1, E2, E3, and E4 are each independently selected from CR E or N. Preferably, at most one of E1, E2, E3, and E4 is selected from N. More preferably, E1, E2, E3, and E4 are each independently selected from CR E ; The R E are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; preferably selected from any one or a combination of at least two of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C2-C10 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl; more preferably selected from any one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, deuterated methyl, phenyl, naphthyl, and pyridyl; the adjacent R E are not connected or are connected by a chemical bond to form a ring; The R E The substituents in it are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C20 alkyl, C2-C20 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, ring E is selected from any one of the following structures: More preferably, formula (a) has any one of the following structures:

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

10. Use of the organoboron compound according to any one of claims 1-9 in the preparation of an organic electroluminescent device; Preferably, the organoboron compound is used as a doping material for the light-emitting layer in an organic electroluminescent device.

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