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). The OLED device prepared from the organic boron-containing compound has the characteristics of low voltage and long service life. The organic boron-containing compound provided by the invention can enable a device to have more excellent comprehensive performance. # imgabs0 #

Description

Technical Field

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

[0002] Organic electroluminescence 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, TVs, computers, and vehicles.

[0003] With the development of organic electroluminescent materials, red light materials and green light materials have basically met the needs of display. However, due to the characteristics of its wide bandgap, it is difficult to inject charges for blue light materials, and they lag behind red light and green light in terms of efficiency and lifespan. However, 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 Application 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 current display requirements during actual application. Another example is that Chinese Patent Application CN101018760A discloses a series of arylamine derivatives, but due to the imbalance between hole transport performance and electron transport performance, their 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 electroluminescence 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 an organic boron-containing compound as an organic blue electroluminescent material (also known as a doping material).

[0006] In the 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 each independently selected from any one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0009] X is selected from O, S, Se, NR X1, CR X2 R 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 not connected to the adjacent ring structure or connected by a chemical bond to form a ring;

[0011] Ar is a structure represented by formula (a);

[0012] In formula (a), the expression of the ring structure with a "-" drawn 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 C1-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 not connected or connected by a chemical bond to form a ring;

[0014] Z1 to Z 18 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 adjacent R Z are not connected or connected by a chemical bond to form a ring;

[0016] The ring A, ring C, ring D, R1, R2, R Z 、R X1 、R X2 、R X3 、R X4 、R X5The substituents in the formula 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.

[0017] In the present invention, R X1 being connected to the adjacent ring structure by a chemical bond to form a ring means that R X1 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), thereby forming a fused ring structure. When the same description is involved hereinafter, it shall have the same meaning and will not be repeated one by one.

[0018] It can be understood that one of Z1 to Z 18 in Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 is selected from C, which is connected to the N in formula (I), and the rest are each independently selected from CR Z or N.

[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 various groups, rather than the effect of a single group / feature.

[0020] 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.

[0021] In some preferred embodiments, the ring A and the ring C are each independently a structure represented by formula (b) or formula (c):

[0022]

[0023] In formula (b) and formula (c), the dotted line represents the fusion position of the group;

[0024] A1 to A8 are each independently selected from CR A or N;

[0025] The R AEach 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 or are connected by a chemical bond to form a ring;

[0026] In formula (c), M represents O, S, NR M1 or CR M2 R M3 , where R M1 , R M2 , R M3 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 R M2 , R M3 are not connected or are connected by a chemical bond to form a ring;

[0027] The substituents of the R A , R M1 , R M2 , R M3 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 any one or a combination of at least two of them.

[0028] In some preferred embodiments, each of the ring D is independently a structure represented by formula (d):

[0029]

[0030] In formula (d), the dashed line represents the fusion position of the group;

[0031] U1, U2, and U3 are each independently selected from CR U or N;

[0032] Said 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 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. Adjacent said R U are not connected or are connected by a chemical bond to form a ring;

[0033] Said R U The 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, and C3-C30 heteroaryl, or a combination of any one or at least two of them.

[0034] In some preferred embodiments, X is selected from O, S, or NR X1 , and the definition of R X1 is the same as its definition in formula (I).

[0035] In some preferred embodiments, the organoboron compound has a structure represented by any one of formula (II-1) to formula (IV-6):

[0036]

[0037] In formula (II-1) to formula (IV-6), the definitions of A1, A2, A3, and A4 are the same as their definitions 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 their definitions in formula (c); the definitions of U1, U2, and U3 are the same as their definitions in formula (d); RX1 has the same definition as that in formula (I).

[0038] In some preferred embodiments, the organoboron compound has a structure represented by formula (II-3), formula (III-3) or formula (III-6).

[0039] In some preferred embodiments, in formula (II-1) to formula (II-3), at most one (0 or 1) of A1, A2, A3, A4 is selected from N, and the rest are independently selected from CR A ; and / or A 1’ , A 2’ , A 3’ , A 4’ at most one (0 or 1) of them is selected from N, and the rest are independently selected from CR A . Preferably, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ , A 4’ are each independently selected from CR A . The Rs in multiple (such as 2, 3, 4, 5, 6, 7, 8) CR A are the same or different groups. Further preferably, A1, A4, A A are selected from CH, and A2, A3, A 1’ , A 4’ are independently selected from CR 2’ , A 3’ respectively. A

[0040] In some preferred embodiments, in formula (III-1) to formula (IV-6), at most one (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 (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 . The Rs in multiple (such as 2, 3, 4, 5, 6, 7, 8) CR A are the same or different groups. Further preferably, A1, A4, A5, A8 are selected from CH, and A2, A3, A6, A7 are independently selected from CR A respectively. A

[0041] In some preferred embodiments, in formula (II-1) to formula (IV-6), at most one (0 or 1) of U1, U2, U3 is selected from N, and the rest are independently selected from CRU Preferably, U1, U2, and U3 are each independently selected from CR U A plurality (e.g., 2 or 3) of CR U wherein R U is the same or different group. Further preferably, U1 and U3 are selected from CH, and U2 is selected from CR U .

[0042] In some preferred embodiments, the R A , R U are 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., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C2, 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, 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;

[0043] The R A , R UThe substituents in [substituent group] are each independently selected from one or a combination of at least two of deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, and C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.

[0044] In some preferred embodiments, the R A , R U are each independently selected from 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.

[0045] 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, preferably selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl.

[0046] In some preferred embodiments, the R A , R U are each independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups, where * represents the attachment site of the group:

[0047] *-CH3, *-CD3, *-CF3,

[0048] In some preferred embodiments, 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.

[0049] In some preferred embodiments, the adjacent R UThey 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.

[0050] In some preferred embodiments, the substituents for the "substituted or unsubstituted" above 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, and C3-C8 (such as C3, C4, C5, C6, C7, etc.) cycloalkyl.

[0051] In some preferred embodiments, the adjacent R A are not connected or are connected by a chemical bond to form a ring, and / or the adjacent R U are not connected or are connected by a chemical bond to form a ring (such as forming etc., the dotted line represents a fused bond). The ring is optionally substituted by one or more substituents selected from deuterium, halogen, cyano, C1-C6 alkyl or C3-C8 cycloalkyl.

[0052] In some preferred embodiments, in formulas (III-1) to (IV-6), M represents O or S.

[0053] In some preferred embodiments, in formulas (III-1) to (IV-6), M represents CR M2 R M3 R M2 and R M3 are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, such as hydrogen, deuterium, methyl, ethyl, n-propyl or isopropyl.

[0054] In some preferred embodiments, in formulas (III-1) to (IV-6), M represents NR M1 R M1 is selected from hydrogen, deuterium, substituted or unsubstituted C6-C10 aryl, such as hydrogen, deuterium, phenyl or tolyl.

[0055] In some preferred embodiments, in formulas (II-3), (III-3), (III-6), (IV-3), (IV-6), the R X1Any one 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; said R X1 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring.

[0056] In some preferred embodiments, said R X1 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, C2-C10 (such as C2, 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, or any one or a combination of at least two of them.

[0057] In some preferred embodiments, in formula (II-3), formula (III-3), formula (III-6), formula (IV-3), formula (IV-6), said R X1 has the structure shown in formula (e):

[0058]

[0059] wherein, * represents the connection site of the group,

[0060] Q1, Q2, Q3, Q4, Q5 are each independently N or CR Q ;

[0061] said R QEach 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 C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl; adjacent R Q are not connected or connected by a chemical bond to form a ring, and the R Q each independently is not connected to the adjacent ring structure or connected by a chemical bond to form a ring.

[0062] In some preferred embodiments, the substituents in the R Q each independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C3-C6 (e.g., C4, C5, etc.) cycloalkyl, C6-C10 (e.g., C7, C8, C9, etc.) aryl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) heteroaryl, or any combination of at least two of them.

[0063] In some more preferred embodiments, at most one (e.g., 0 or 1) of Q1, Q2, Q3, Q4, Q5 is N, and the rest are independently selected from CR Q .

[0064] In some more preferred embodiments, Q1, Q2, Q3, Q4, Q5 are each independently CR Q ; the R Q in a plurality (2, 3, 4, 5) of CR Q are the same or different groups.

[0065] In some more preferred embodiments, the R QEach independently selected from hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, deuterated C1-C6 alkyl, C6-C10 aryl-substituted C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, C2-C6 alkenyl, C6-C10 aryl-substituted C2-C6 alkenyl, C6-C20 aryl, C1-C6 alkyl and / or C3-C6 cycloalkyl-substituted C6-C20 aryl, C3-C20 heteroaryl, C1-C6 alkyl and / or C3-C6 cycloalkyl-substituted C3-C20 heteroaryl.

[0066] In some more preferred embodiments, the number of CH in Q1, Q2, Q3, Q4, Q5 is 2, 3, 4 or 5.

[0067] In some more preferred embodiments, in formula (II-3), formula (III-3), formula (IV-3), the R X1 in which Q1 and A1 and / or Q5 and U1 are not connected or connected by a chemical bond to form a ring. Preferably, the R X1 in which Q1 and A1 are not connected or connected by a chemical bond to form a ring (for example, Q1 and A1 are connected by a single bond, O, or S, which together with N in the parent nucleus form a five-membered or six-membered ring, etc.).

[0068] In some more preferred embodiments, the organoboron compound has a structure represented by any one of formula (II-3-1), formula (III-3-1), formula (IV-3-1):

[0069]

[0070] In formula (II-3-1), formula (III-3-1), formula (IV-3-1), the definitions of A2, A3, A4 are the same as those in formula (b); A 2’ , A 3’ , A 4’ have the same definitions as A2, A3, A4; the definition of A 1’ is the same as the definition of A1; the definitions of M, A5, A6, A7, A8 are the same as those in formula (c); the definitions of U1, U2, U3 are the same as those in formula (d); the definitions of Q2, Q3, Q4, Q5 are the same as those in formula (e); Y each independently represents a single bond, O, S or does not exist.

[0071] In some more preferred embodiments, adjacent R Q are not connected or 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 aryl ring.

[0072] In the above-mentioned "substituted or unsubstituted", the substituents of the substitution 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, and C3-C6 (such as C4, C5, etc.) cycloalkyl.

[0073] In some more preferred embodiments, the adjacent R Q are not connected or are connected by a chemical bond to form a ring (such as forming

[0074] etc., and the dashed line represents a fused bond). The ring is optionally substituted by one or more substituents selected from deuterium, halogen, cyano, C1-C6 alkyl, and C3-C6 cycloalkyl.

[0075] In some preferred embodiments, the R X1 is selected from any one of the following groups, and * represents the connection site of the group:

[0076]

[0077]

[0078] In some embodiments, the formula (a) has a structure shown in any one of formula (a-1) to formula (a-5), and * represents the connection site of the group:

[0079]

[0080] In formula (a-1) to formula (a-5), the definitions of R1, R2, Z1 to Z 18 are the same as those in formula (a).

[0081] In some preferred embodiments, the formula (a) has a structure shown in formula (a-1) or formula (a-4).

[0082] In some preferred embodiments, each of R1 and R2 is independently selected from hydrogen, deuterium, 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, or a combination of any one or at least two of them; preferably, each of R1 and R2 is independently selected from methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl, or a combination of one or two of them; more preferably, each of R1 and R2 is independently selected from methyl or phenyl.

[0083] In some preferred embodiments, Z1 to Z 18 are each independently selected from CR Z . Preferably, Z1, Z4, Z8, Z9-Z 18 are selected from CH.

[0084] In some preferred embodiments, the R Z are each independently selected from hydrogen, deuterium, halogen, 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, or a combination of any one or at least two of them; preferably, the R Z are each independently selected from hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, or a combination of one or two of them; more preferably, the R Z are each independently selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl, or phenyl.

[0085] In some preferred embodiments, the formula (a) has any of the following structures, where * represents the connection site of the group:

[0086]

[0087] In some embodiments, the organoboron compound of the present invention has any of the following structures:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] In a second aspect, the present invention provides the use of the above-mentioned organoboron compound in the preparation of an organic electroluminescent device.

[0111] 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 an organic electroluminescent device.

[0112] 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%, 12 wt%, 13 wt%, 15 wt%, 16 wt%, 18 wt%) relative to the host material in the light-emitting layer, preferably 1 wt% to 15 wt%, more preferably 2 wt% to 10 wt%.

[0113] In a third aspect, the present invention provides an organic electroluminescent device, which includes a light-emitting layer, and the doping material of the light-emitting layer contains the organic boron-containing compound of the present invention as described above.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] The specific reason for the excellent performance of the above-mentioned organic boron-containing compound of the present invention as a doping material in the light-emitting layer of an organic electroluminescent device is not yet clear. It is speculated that the possible reasons are as follows:

[0119] The organic boron-containing compound provided by the present invention has the structure shown in formula (I). By introducing the large steric hindrance group of formula (a), the conjugation effect of the overall molecule is improved, the formation of exciplexes is effectively reduced, and 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

[0120] 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 completed without departing from the spirit disclosed by the present invention shall be included within the scope of the claims.

[0121] Definition of Substituent Terms

[0122] In the present invention, for the expression of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0123] 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.

[0124] In the present invention, the expression of a ring structure with a "-" drawn across it indicates that the bonding site is at any position on the ring structure where bonding can occur.

[0125] In the present invention, both "-*" and "*" represent the bonding sites of groups.

[0126] In the present invention, "independently of each other" means that when the subject has multiple entities, they can be the same or different from each other.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] In the present invention, the C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0132] In the present invention, the C3-C30 may each independently be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0133] 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 a group containing at least 1 phenyl group, and when containing at least 2 phenyl groups, the phenyl groups are connected by a single bond. Exemplary but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the polycyclic aryl group means a group containing 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. Exemplary but 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, 9,9-dinaphthylfluorenyl, spirofluorenyl, benzofluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl), etc.), fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, -yl, tetracenyl, acenaphthylenyl, benzacenaphthylenyl, etc. It should be noted that monocyclic aryl groups and polycyclic aryl groups connected by a single bond also belong to the scope of aryl groups, such as phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0134] In the present invention, unless otherwise specified, the C6-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes a monocyclic heteroaryl group or a polycyclic 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 polycyclic 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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] In the present invention, the C1-C20 alkyl group, preferably a C1-C16 alkyl group, more preferably a 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.

[0139] 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 above-mentioned alkyl group examples.

[0140] 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 group, exemplarily including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0141] 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. 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.

[0142] 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.

[0143] In the present invention, the C2-C20 alkenyl group, preferably a 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.

[0144] 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 further.

[0145] 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.

[0146] 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. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability. 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 represents 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.

[0147] 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 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.

[0148] 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.

[0149] The materials described in the present invention as being useful for a specific layer in an organic light-emitting device 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, barrier 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 U.S. Patent Application US2015 / 0349273M, the entire contents of which are 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.

[0150] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Nanjing Institute of Micro-Science, the optical test system and life test system produced by Suzhou Fushida, the ellipsometer produced by Wuhan Yiguang Technology, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents will not be elaborated in this invention.

[0151] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0152] Example 1: Synthesis of Compound I-19

[0153]

[0154]

[0155] (1-1) Synthesis of intermediate S1-1:

[0156] Under nitrogen protection, add raw material M1-1 (33.10 g) and tetrahydrofuran (200 mL) to a dry three-necked reaction flask. Cool the temperature to -78 °C, stir for 0.5 h, and slowly dropwise add a pentane solution of tert-butyllithium (68.75 mL, 1.6 M). Control the temperature to react at -78 °C for 1 h, then keep the temperature and dropwise add a tetrahydrofuran (100 mL) solution of raw material M1-2 (23.01 g). Keep the temperature and react for 1 h, then slowly raise the temperature to room temperature and continue to react for 8 h. Add a saturated ammonium chloride solution to quench the reaction, dilute with water, separate the layers, extract the aqueous phase with dichloromethane (80 mL), combine the organic phases, concentrate to remove the solvent to obtain an oily substance. Then add acetic acid (100 mL) and concentrated hydrochloric acid (20 mL), heat to 70 °C and react overnight. Cool, concentrate to remove the solvent, separate dichloromethane (40 mL) and water (40 mL), combine the organic phases, wash with saturated sodium bicarbonate until neutral, wash with saturated brine, dry with anhydrous sodium sulfate, and perform column chromatography to obtain intermediate S1-1 (18.23 g, yield 39.1%).

[0157] (1-2) Synthesis of intermediate S1-2:

[0158] Under nitrogen protection, add intermediate S1-1 (13.98 g), raw material M1-3 (4.47 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) to a dry three-necked reaction flask. Slowly raise the temperature to 110 °C with stirring and react for 4 h. After cooling the reaction solution, add water (100 mL), wash with water and concentrate, perform column chromatography, recrystallize, and dry to obtain intermediate S1-2 (11.85 g, yield 68.2%).

[0159] (1-3) Synthesis of intermediate S1-3:

[0160] Under nitrogen protection, add raw material M1-4 (13.20 g), raw material M1-5 (13.96 g), cesium carbonate (32.58 g) and DMF (200 mL) to a dry three-necked reaction flask. Raise the temperature to 100 °C and react for 12 h. After cooling to room temperature, add water (400 mL), precipitate a solid, filter, and wash the filter cake with ethanol by boiling to obtain intermediate S1-3 (14.33 g, yield 54.8%).

[0161] (1-4) Synthesis of intermediate S1-4:

[0162] Under nitrogen protection, add intermediate S1-3 (10.46 g), intermediate S1-2 (11.59 g), sodium tert-butoxide (3.84 g), Pd2(dba)3 (0.37 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.76 g) and toluene (180 mL) into a dry three-necked reaction flask. Slowly heat up to 110 °C with stirring and react for 3 h. After the reaction solution is cooled, add water (100 mL), wash with water, concentrate, perform column chromatography, recrystallize, and dry to obtain intermediate S1-4 (13.19 g, yield 64.5%).

[0163] (1-5) Synthesis of compound I-19:

[0164] Under nitrogen protection, add intermediate S1-4 (10.23 g) and anhydrous xylene (150 mL) into a dry three-necked reaction flask. Cool down to -78 °C and 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 resume the reaction at room temperature for 6 h. Then cool down to 0 °C and dropwise add N,N-diisopropylethylamine (7.0 mL) and react at 150 °C for 15 h. After the reaction is completed, cool to room temperature, wash with water, separate the liquid, dry, concentrate, perform column chromatography, and recrystallize to obtain compound I-19 (1.74 g, yield 17.5%).

[0165] MS (m / e) of compound I-19: 996.03; 1 1H NMR (400 MHz, CDCl3): δ 8.33 (d, 1H), 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.90 (m, 3H), 7.68 - 7.43 (m, 7H), 7.42 - 7.17 (m, 11H), 7.13 (dd, 1H), 7.06 (d, 1H), 7.00 (d, 1H), 1.56 (s, 3H), 1.51 (s, 3H), 1.35 (dd, 36H).

[0166] Example 2: Synthesis of compound I-43

[0167]

[0168]

[0169] The synthesis route of compound I-43 is the same as that of compound I-19. Just replace raw material M1-1 with raw material M2-1 to obtain compound I-43.

[0170] MS (m / e) of compound I-43: 996.47; 1HNMR(400 MHz, CDCl3): δ 8.33 (d, 1H), 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.90 (m, 3H), 7.68 - 7.43 (m, 6H), 7.42 - 7.17 (m, 12H), 7.09 - 6.98 (m, 3H), 1.58 (s, 3H), 1.53 (s, 3H), 1.35 (dd, 36H).

[0171] Example 3: Synthesis of Compound II-38

[0172]

[0173] (3-1) Synthesis of Intermediate S3-1:

[0174] Under nitrogen protection, add raw material M3-1 (21.10 g), raw material M3-2 (28.12 g), sodium tert-butoxide (19.22 g), Pd2(dba)3 (1.83 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (3.81 g) and toluene (250 mL) into a dry three-necked reaction flask. Slowly heat up to 105 °C with stirring and react for 5 h. After the reaction solution cools down, add water (100 mL), wash with water and concentrate. Then perform column chromatography, recrystallization, and drying to obtain Intermediate S3-1 (27.82 g, yield 67.3%).

[0175] (3-2) Synthesis of Intermediate S3-2:

[0176] The synthesis route of Intermediate S3-2 is the same as that of Intermediate S1-2. Just replace raw material M1-3 with raw material M3-3 to obtain Intermediate S3-2. (3-3) Synthesis of Intermediate S3-3:

[0177] The synthesis route of Intermediate S3-3 is the same as that of Intermediate S3-1. Just replace raw material M3-1 with raw material M3-4 and raw material M3-2 with Intermediate S3-1 to obtain Intermediate S3-3.

[0178] (3-4) Synthesis of Intermediate S3-4:

[0179] The synthesis route of Intermediate S3-4 is the same as that of Intermediate S3-1. Just replace raw material M3-1 with Intermediate S3-3 and raw material M3-2 with Intermediate S3-2 to obtain Intermediate S3-4.

[0180] (3-5) Synthesis of Compound II-38:

[0181] The synthesis route of Compound II-38 is the same as that of Compound I-19. Just replace Intermediate S1-4 with Intermediate S3-4 to obtain Compound II-38.

[0182] MS (m / e) of Compound II-38: 1186.75; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.97 - 7.90 (m, 2H), 7.82 (d, 1H), 7.73 (d, 1H), 7.65 - 7.43 (m, 9H), 7.42 - 7.30 (m, 10H), 7.24 - 7.18 (m, 3H), 7.15 (dd, 1H), 7.00 (d, 1H), 6.91 - 6.85 (m, 2H), 1.56 (s, 3H), 1.51 (s, 3H), 1.38 - 1.32 (m, 45H).

[0183] Example 4: Synthesis of Compound II-149

[0184]

[0185] The synthetic route of Compound II-149 is the same as that of Compound II-38, except that raw material M3-1 is replaced by raw material M4-1, raw material M3-2 is replaced by raw material M4-2, intermediate S1-1 is replaced by intermediate S2-1, and raw material M3-3 is replaced by raw material M4-3, then Compound II-149 can be obtained.

[0186] MS (m / e) of Compound II-149: 1122.29; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.84 (m, 5H), 7.78 - 7.72 (m, 1H), 7.69 (d, 1H), 7.66 - 7.58 (m, 2H), 7.58 - 7.43 (m, 6H), 7.42 - 7.19 (m, 13H), 7.06 - 6.97 (m, 2H), 6.91 - 6.85 (m, 2H), 1.58 (s, 3H), 1.53 (s, 3H), 1.35 (t, 27H).

[0187] Example 5: Synthesis of Compound II-233

[0188]

[0189] (5-1) Synthesis of Intermediate S5-1:

[0190] The synthetic route of Intermediate S5-1 is the same as that of Intermediate S3-2, except that raw material M3-3 is replaced by raw material M4-3, and intermediate S1-1 is replaced by raw material M5-1, then Intermediate S5-1 can be obtained.

[0191] (5-2) Synthesis of Compound II-233:

[0192] The synthetic route of Compound II-233 is the same as that of Compound II-38. Only by replacing intermediate S3-1 with intermediate S1-2 and intermediate S3-2 with intermediate S5-1 can Compound II-233 be obtained.

[0193] MS (m / e) of Compound II-233: 1246.81; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.90 (m, 2H), 7.81 (d, 2H), 7.69 (d, 1H), 7.64 - 7.59 (m, 1H), 7.58 - 7.25 (m, 23H), 7.21 (dd, 1H), 7.13 (dd, 1H), 7.00 (d, 1H), 6.92 - 6.86 (m, 2H), 1.56 (s, 3H), 1.51 (s, 3H), 1.38 - 1.32 (m, 45H).

[0194] Example 6: Synthesis of Compound II-350

[0195]

[0196] (6-1) Synthesis of Intermediate S6-1:

[0197] The synthetic route of Intermediate S6-1 is the same as that of Intermediate S3-2. Only by replacing intermediate S1-1 with raw material M6-1 can Intermediate S6-1 be obtained. (6-2) Synthesis of Compound II-350:

[0198] The synthetic route of Compound II-350 is the same as that of Compound II-38. Only by replacing intermediate S3-1 with intermediate S2-2 and intermediate S3-2 with intermediate S6-1 can Compound II-350 be obtained.

[0199] MS (m / e) of Compound II-350: 1238.42; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.91 (m, 2H), 7.87 - 7.75 (m, 3H), 7.73 (d, 1H), 7.64 - 7.59 (m, 1H), 7.58 - 7.16 (m, 25H), 7.05 - 6.98 (m, 2H), 6.96 - 6.85 (m, 6H), 1.58 (s, 3H), 1.53 (s, 3H), 1.35 (t, 27H).

[0200] Example 7: Synthesis of Compound III-13

[0201]

[0202] (7-1) Synthesis of Intermediate S7-2:

[0203] The synthesis route of Intermediate S7-2 is the same as that of Intermediate S1-2. Just replace raw material M1-1 with raw material M7-1 and raw material M1-3 with raw material M7-2, then Intermediate S7-2 can be obtained.

[0204] (7-2) Synthesis of Intermediate S7-3:

[0205] Under nitrogen protection, add raw material M7-3 (20.79 g), raw material M7-4 (9.30 g), potassium carbonate (27.65 g) and NMP (200 mL) into a dry three-necked reaction flask, heat up to 120 °C and react for 10 h. After the reaction is completed, cool down to room temperature, perform vacuum distillation, add water (100 mL) and toluene (100 mL), separate by liquid separation and then perform vacuum distillation, and purify by column chromatography to obtain Intermediate S7-3 (21.54 g, yield 76.4%).

[0206] (7-3) Synthesis of Compound III-13:

[0207] The synthesis route of Compound III-13 is the same as that of Compound I-19. Just replace Intermediate S1-3 with Intermediate S7-3 and Intermediate S1-2 with Intermediate S7-2, then Compound III-13 can be obtained.

[0208] MS (m / e) of Compound III-13: 755.43; 1 HNMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.91 (m, 2H), 7.83 (dd, 1H), 7.75 (dd, 1H), 7.65 - 7.24 (m, 17H), 7.18 (dd, 1H), 7.04 - 7.97 (m, 1H), 6.91 (dd, 1H), 6.77 (dd, 1H), 6.67 (dd, 1H), 1.58 (s, 3H), 1.53 (s, 3H).

[0209] Example 8: Synthesis of Compound III-27

[0210]

[0211] (8-1) Synthesis of Intermediate S8-1:

[0212] Under nitrogen protection, add raw material M8-1 (22.10 g), raw material M8-2 (23.39 g), anhydrous potassium carbonate (27.64 g), Pd(PPh3)4 (2.31 g), toluene (300 mL), ethanol (100 mL) and deionized water (100 mL) into a dry three-necked reaction flask, and heat up to 100 °C for reaction for 5 h. After the reaction is completed, cool to room temperature, wash with water and separate the layers. Extract the aqueous phase with toluene, collect the organic phase, perform column chromatography, recrystallize, and dry to obtain intermediate S8-1 (22.27 g, yield 67.1%).

[0213] (8-2) Synthesis of intermediate S8-3:

[0214] The synthesis route of intermediate S8-3 is the same as that of intermediate S7-2. Only by replacing raw material M7-1 with intermediate S8-1 and raw material M7-2 with raw material M8-3 can intermediate S8-3 be obtained.

[0215] (8-3) Synthesis of compound III-27:

[0216] The synthesis route of compound III-27 is the same as that of compound III-13. Only by replacing raw material M7-4 with raw material M8-4 and intermediate S7-2 with intermediate S8-3 can compound III-27 be obtained.

[0217] MS (m / e) of compound III-27: 739.01; 1 1H NMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.91 (m, 2H), 7.65 - 7.23 (m, 18H), 7.18 (dd, 1H), 7.11 - 7.01 (m, 3H), 6.77 (dd, 1H), 6.72 (dd, 1H), 1.56 (s, 3H), 1.51 (s, 3H).

[0218] Example 9: Synthesis of compound I-68

[0219]

[0220]

[0221] The synthesis route of compound I-68 is the same as that of compound II-38. Only by replacing raw material M3-4 with raw material M9-1, intermediate S3-1 with raw material M9-2, and intermediate S3-2 with intermediate S1-2 can compound I-68 be obtained.

[0222] MS (m / e) of compound I-68: 942.22; 1HNMR(400MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 7.99 - 7.90 (m, 2H), 7.66 - 7.43 (m, 6H), 7.42 - 7.24 (m, 11H), 7.22 (dd, 2H), 7.13 (dd, 1H), 7.08 - 6.97 (m, 4H), 6.84 - 6.77 (m, 2H), 1.56 (s, 3H), 1.51 (s, 3H), 1.34 (d, 27H).

[0223] Example 10: Synthesis of Compound II-5

[0224]

[0225] (10-1) Synthesis of Intermediate S10-1:

[0226] Under nitrogen protection, add raw material M10-1 (19.41 g), pyridine (23.73 g) and dichloromethane (500 mL) to a dry three-necked reaction flask, cool down to -20 °C, and stir for 0.3 h. Slowly add trifluoromethanesulfonic anhydride (25.25 mL) dropwise, control the temperature at -20 °C and react for 1 h, then slowly warm up to room temperature and continue to react for 10 h. After the reaction is completed, wash with water, saturated sodium bicarbonate solution and water in sequence, dry with anhydrous magnesium sulfate, filter, and perform column chromatography to obtain intermediate S10-1 (16.32 g, yield 50.1%).

[0227] (10-2) Synthesis of Intermediate S10-4:

[0228] The synthesis route of intermediate S10-4 is the same as that of intermediate S8-3. Just replace raw material M8-1 with intermediate S10-1, raw material M8-2 with raw material M10-2, and raw material M8-3 with raw material M10-3 to obtain intermediate S10-4.

[0229] (10-3) Synthesis of Compound II-5:

[0230] The synthesis route of compound II-5 is the same as that of compound III-27. Just replace raw material M8-4 with raw material M10-4, and intermediate S8-3 with intermediate S10-4 to obtain compound II-5.

[0231] MS (m / e) of Compound II-5: 755.78; 11H NMR (400 MHz, CDCl3): δ 8.25 (d, 1H), 8.07 (dd, 1H), 8.00 - 7.91 (m, 2H), 7.86 - 7.80 (m, 1H), 7.70 (dd, 1H), 7.66 - 7.23 (m, 18H), 7.14 - 7.03 (m, 2H), 6.97 (dd, 1H), 6.87 (dd, 1H), 1.58 (s, 3H), 1.53 (s, 3H).

[0232] Exemplarily, the present invention gives the specific synthesis methods of the above several compounds. For the compounds without specific synthesis methods given, they are also prepared by similar methods, and can be obtained only by replacing the raw materials, which will not be elaborated here. Alternatively, those skilled in the art can also prepare them by other methods in the prior art.

[0233] Device Example 1

[0234] 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.

[0235] At a vacuum of about 10 -8 Torr, sequentially evaporate on the ITO anode by thermal vacuum at a rate of Compounds HT and HI (weight ratio 97:3) are co-evaporated as a hole injection layer (HIL) with a thickness of Compound HT is used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, BH as a blue light host and compound I-19 as a doping material (weight ratio 98:2) are co-evaporated as an emitting layer (EML) with a thickness of Compound HB is used as a hole blocking layer (HBL) with a thickness of On the hole blocking layer, compounds ET and lithium 8-hydroxyquinoline (Liq) are co-evaporated (weight ratio 50:50) as an electron transport layer (ETL) with a thickness of Finally, evaporate A thickness of lithium 8-hydroxyquinoline (Liq) as an electron injection layer (EIL), and evaporate Aluminum of as a cathode. Then transfer the device back to the glove box and encapsulate it with a glass cover to complete the device.

[0236] Device Examples 2 - 10, Device Comparative Example 1

[0237] The difference from 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.

[0238] The molecular structural formulas of the related materials are shown as follows:

[0239]

[0240] 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 In order to better show 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 1-10 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.

[0241] Table 1

[0242] Device Doped material Voltage (V) EQE Lifetime (h) Device Example 1 Compound I-19 95％ 107％ 113％ Device Example 2 Compound I-43 95％ 108％ 112％ Device Example 3 Compound II-38 91％ 113％ 117％ Device Example 4 Compound II-149 92％ 114％ 118％ Device Example 5 Compound II-233 92％ 115％ 117％ Device Example 6 Compound II-350 91％ 114％ 119％ Device Example 7 Compound III-13 93％ 109％ 112％ Device Example 8 Compound III-27 94％ 110％ 108％ Device Example 9 Compound I-68 95％ 107％ 110％ Device Example 10 Compound II-5 94％ 111％ 113％ Device Comparative Example 1 Ref-1 100％ 100％ 100％

[0243] As shown in Table 1, at a current density of 10 mA / cm 2 compared with Device Comparative Example 1, for Device Examples 1-10, the voltage can be reduced by 5-9%, the external quantum efficiency can be increased by 7%-15%, and the device lifetime can be extended, with the maximum extension of 19%. The above data show that the device prepared from the organoboron compound provided by the present invention has a lower driving voltage, higher current efficiency and longer lifetime.

[0244] 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 and preferred embodiments described herein. Many of the materials and structures described herein can 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. An organoboron compound having the structure shown in 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 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 by a chemical bond to form a ring; Ar has the structure shown in formula (a); In formula (a), the expression of the ring structure with a "—" drawn across it indicates that the bonding site is 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. R1 and R2 are either not connected or connected by a chemical bond to form a ring; Z1 to Z 18 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; The substituents substituted in the ring A, ring C, ring D, 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, 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, wherein Ring A and ring C are each independently a structure shown in formula (b) or formula (c): 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), 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 there is no connection or they are connected by a chemical bond to form a ring between the said R M2 , R M3 ; 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.

3. The organoboron compound according to claim 1 or 2, characterized in that, Ring D has the structure shown in formula (d): In formula (d), the dotted line indicates 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 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 U are not connected or are connected by a chemical bond to form a ring; The R U 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, 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.

4. The organoboron compound according to any one of claims 1 to 3, characterized in that, X is 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 formula (II-1) to formula (IV-6); In Formula (II-1) to Formula (IV-6), A1, A2, A3, and A4 are defined in the same manner as in Formula (b); A 1’ , A 2’ , A 3’ , A 4’ are defined in the same manner as A1, A2, A3, and A4; M, A5, A6, A7, and A8 are defined in the same manner as in Formula (c); U1, U2, and U3 are defined in the same manner as in Formula (d); R X1 is defined in the same manner as in Formula (I); Preferably, in formulas (II-1) to (II-3), at most one of A1, A2, A3, A4 is selected from N, and / or A 1’ , A 2’ , A 3’ , A 4’ ; preferably, at most one of A1, A2, A3, A4, A 1’ , A 2’ , A 3’ , A 4’ is independently selected from CR A ; Preferably, in formulas (III-1) to (IV-6), at most one of A1, A2, A3, and A4 is selected from N, and / or at most one of A5, A6, A7, and A8 is selected from N; preferably, A1, A2, A3, A4, A5, A6, A7, and A8 are each independently selected from CR A ; Preferably, in Formula (II-1) to Formula (IV-6), at most one of U1, U2, and U3 is selected from N, and preferably, U1, U2, and U3 are each independently selected from CR U .

5. The organoboron compound according to any one of claims 2-4, characterized in that, The R A and R U are each independently selected from any one of 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, and substituted or unsubstituted C3-C30 heteroaryl; preferably 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; the adjacent R A are not connected or are connected by a chemical bond to form a ring, and the adjacent R U are not connected or are connected by a chemical bond to form a ring; The R A , R U The substituents in 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; preferably selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; Preferably, the R A , R U are each independently selected from hydrogen, deuterium, halogen, cyano or any one of the following groups: Preferably, 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 adjacent R U 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; In the above-mentioned "substituted or unsubstituted", the substituents of the substitution are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, a C1-C6 alkyl group, and a C3-C8 cycloalkyl group.

6. The organoboron compound according to any one of claims 1-5, characterized in that, The R X1 is selected from any one of substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R X1 is not connected to the adjacent ring structure or forms a ring by chemical bonding; Optionally, the substituents substituted in the R X1 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, the R X1 is selected from any of the following groups:

7. The organoboron compound according to any one of claims 4-6, characterized in that, The organoboron compound has a structure represented by any one of formula (II-3-1), formula (III-3-1), and formula (IV-3-1); In Formula (II-3-1), Formula (III-3-1), and Formula (IV-3-1), A2, A3, and A4 are defined in the same manner as in Formula (b); A 2’ , A 3’ , A 4’ are defined in the same manner as A2, A3, and A4; A 1’ is defined in the same manner as A1; M, A5, A6, A7, and A8 are defined in the same manner as in Formula (c); U1, U2, and U3 are defined in the same manner as in Formula (d); Q2, Q3, Q4, and Q5 are each independently N or CR Q ; The R Q are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; adjacent R Q are not connected or are connected by a chemical bond to form a ring, and the R Q are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; The R Q The substituents in it are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl; Y each independently represents a single bond, O, S, or does not exist.

8. The organoboron compound according to any one of claims 1-7, characterized in that, Formula (a) has a structure shown in any one of formula (a-1) to formula (a-5); In Formula (a-1) to Formula (a-5), R1, R2, Z1 to Z 18 are defined the same as in Formula (a); Preferably, R1 and R2 are each independently selected from any one or a combination of at least two of hydrogen, deuterium, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C6-C20 aryl group, and a C3-C20 heteroaryl group; more preferably, R1 and R2 are each independently selected from one or a combination of two of methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, and pyridyl; further preferably, R1 and R2 are each independently selected from methyl or phenyl; Preferably, Z1 to Z 18 are each independently selected from CR Z , and 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 a combination of one or two of hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl; more preferably, the Rz are each independently selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl, or phenyl; 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 in the light-emitting layer of the organic electroluminescent device; More preferably, the doping concentration of the doping material is 1 wt% to 20 wt%, preferably 1 wt% to 15 wt%, and more preferably 2 wt% to 10 wt% relative to the host material in the light-emitting layer.

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