Organic boron-containing compound and application thereof

Abstract

The invention provides an organic boron-containing compound and application thereof. The organic boron-containing compound has a structure as shown in a formula (I). The organic boron-containing compound is used for the organic electroluminescent device, can be used as a doping material of a luminescent layer, and can effectively improve the luminescent efficiency of the device, prolong the service life of the device, reduce the voltage and energy consumption and enable the device to have higher color purity. # 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 the application of the organic boron-containing compound 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 vehicles due to a series of advantages such as self-luminescence, wide viewing angles, high contrast ratios, fast response speeds, low power consumption, thinner and more power-saving, and flexible display capabilities.

[0003] With the development of organic electroluminescent materials, red light materials and green light materials have basically met the needs of displays. However, due to the characteristics of their wide bandgaps, blue light materials are difficult to inject charges and are lagging behind red and green lights 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 require 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 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-lifespan blue light-emitting materials is of great significance for promoting the development of organic electroluminescent display and lighting technologies. Summary of the Invention

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

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

[0007]

[0008] In formula (I), X is selected from O, S, Se, NR X1 , CR X2 R X3 or SiR X4 R X5 ;

[0009] 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;

[0010] A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from N or CR1;

[0011] U1, U2, U3, U4, U5, U6, U7, U8, U9, U 10 、U 11 、U 12 、U 13 、U 14 are each independently selected from N or CR2;

[0012] R1 and R2 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 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino. Among R1 and R2, at least two adjacent groups are not connected or connected by a chemical bond to form a ring, and R1 and R2 are not connected to the adjacent ring structure or connected by a chemical bond to form a ring;

[0013] The R1, R2, R X1 、R X2 、R X3 、R X4 、R X5The substituents described in [reference] are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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;

[0014] represents a single bond or a double bond.

[0015] It should be noted that in the present invention, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect between each group, rather than the effect of a single group / feature.

[0016] The following are 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.

[0017] In some preferred embodiments, X is selected from O, S, or NR X1 ; preferably, the organoboron compound has a structure represented by any one of formulas (II-1) to (II-3):

[0018]

[0019] In formulas (II-1) to (II-3), A1 to A8, U1 to U 14 , R X1 are defined in the same way as in formula (I).

[0020] In some preferred embodiments, the R X1 is selected from any one of a substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl and a 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.

[0021] In some preferred embodiments, the R X1The substituents described in [reference] are independently selected from any one or a combination of at least two of deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.

[0022] In some preferred embodiments, the R X1 The substituents described in [reference] are independently selected from deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-pentyl, etc.), C1-C6 deuterated alkyl (such as deuterated methyl, deuterated tert-butyl, etc.), C1-C6 haloalkyl (such as fluoromethyl, etc.), C1-C6 alkyl substituted with C6-C20 aryl (such as tert-butyl substituted with phenyl (such as ) etc.), C3-C6 cycloalkyl (such as cyclopentyl, cyclohexyl, etc.), C6-C20 aryl (such as phenyl, naphthyl, fluorenyl, 1,2,3,4-tetrahydronaphthyl, etc.), C6-C20 deuterated aryl (such as deuterated phenyl, etc.), C6-C20 aryl substituted with C1-C6 alkyl (such as tert-butylphenyl, m-di-tert-butylphenyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, etc.), C3-C20 heteroaryl (such as carbazolyl, etc.), or C3-C20 heteroaryl substituted with C1-C6 alkyl (such as carbazolyl substituted with tert-butyl, etc.).

[0023] In some preferred embodiments, the R X1 is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring.

[0024] In the present invention, R X1 being connected by a chemical bond to the adjacent ring structure 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 the ring where A8 is located or the ring where U 14 is located) by a chemical bond (such as a single bond, O or S, etc.) to form a fused ring structure. When the same description is involved hereinafter, it shall have the same meaning and will not be elaborated one by one.

[0025] In some preferred embodiments, the R X1Selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorene, benzofluorenyl, pyridyl, benzoxanthenyl, benzothioxanthenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; wherein said R X1 The substituents of the said substitution are each independently selected from one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl.

[0026] In some preferred embodiments, said R X1 Is selected from any one of the following groups, * represents the connection site of the group:

[0027]

[0028]

[0029] 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 CR1.

[0030] In some preferred embodiments, at most one (0 or 1) of A5, A6, A7, A8 is selected from N, and the rest are independently selected from CR1.

[0031] Preferably, A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from CR1. R1 in multiple (such as 2, 3, 4, 5, 6, 7, 8) CR1s is the same or different groups. Further preferably, A1, A4, A5, A8 are selected from CH, and A2, A3, A6, A7 are each independently selected from CR1.

[0032] In some preferred embodiments, each of the R1 is 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 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.) 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, 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; preferably 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 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino.

[0033] In some preferred embodiments, the substituents of the substituted R1 are independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, 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, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, or a combination of one or at least two of them.

[0034] In some preferred embodiments, the substituents of the R1 are independently selected from deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, etc.), C1-C6 deuterated alkyl (such as deuterated methyl, deuterated tert-butyl, etc.), C1-C6 haloalkyl (such as fluoromethyl, etc.), C3-C6 cycloalkyl (such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.), C6-C20 aryl (such as phenyl, fluorenyl, naphthyl, anthryl, phenanthryl, pyrenyl, etc.), C6-C20 deuterated aryl (such as deuterated phenyl, etc.), C6-C20 aryl substituted by C1-C6 alkyl (such as tert-butylphenyl, m-di-tert-butylphenyl, etc.), or C3-C20 heteroaryl (such as pyridyl, benzofuranyl, benzothiophenyl, etc.).

[0035] In some preferred embodiments, each of the R1 is independently selected from hydrogen, deuterium, halogen, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, tetrahydropyranyl, phenyl, pyridyl, indanyl, tetrahydronaphthyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, fluorenyl, spirofluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, (wherein Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, phenanthryl, anthryl, pyrenyl, pyridyl, dibenzofuranyl or dibenzothiophenyl, and * represents the connection site of the group); the substituents of the R1 are independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, phenyl, pyridyl.

[0036] More preferably, each of the R1 is independently selected from hydrogen, deuterium, halogen, cyano or any one of the following groups, and * represents the connection site of the group:

[0037]

[0038] Preferably, at least two adjacent R1 are not connected or are connected by a chemical bond to form a ring (such as forming etc., and the dotted line represents a fused bond).

[0039] In some embodiments, any adjacent R1 and R X1 are not connected or are connected by a chemical bond (such as a single bond, O or S, etc.) to form a ring.

[0040] In some preferred embodiments, at most one (0 or 1) of U1, U2, U3, U4 is selected from N, and the rest are independently selected from CR2.

[0041] In some preferred embodiments, at most one (0 or 1) of U5, U6, U7, U8 is selected from N, and the rest are independently selected from CR2.

[0042] In some preferred embodiments, U9, U 10 、U 11 、U 12 at most one (0 or 1) of them is selected from N, and the rest are independently selected from CR2.

[0043] In some preferred embodiments, U 13 、U 14 at most one (0 or 1) of them is selected from N, and the rest are independently selected from CR2.

[0044] Preferably, U1, U2, U3, U4, U5, U6, U7, U8, U9, U 10 、U 11 、U 12 、U 13 、U 14 are each independently selected from CR2. R2 in a plurality (such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14) of CR2 is the same or different groups. Preferably, U4, U5, U 12 、U 13 、U 14 are CH, and U1, U2, U3, U6, U7, U8, U9, U 10 、U 11 are each independently selected from CR2.

[0045] Preferably, each of the R2s is 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 C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, 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; preferably selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl.

[0046] In some preferred embodiments, the substituents of the substituted R2s are independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, 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, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, or a combination of one or at least two of them.

[0047] In some preferred embodiments, the substituents of the substituted R2s are independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 alkyl (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, etc.), C1-C6 deuterated alkyl (e.g., deuterated methyl, deuterated tert-butyl, etc.), C1-C6 haloalkyl (e.g., fluoromethyl, etc.).

[0048] More preferably, each of the R2s is independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups, where * represents the attachment site of the group:

[0049]

[0050] Preferably, at least two adjacent R2s are not connected or are connected by a chemical bond to form a ring (e.g., forming etc., and the dashed line represents a fused bond).

[0051] In some preferred embodiments, the organoboron compound has a structure represented by any one of Formula (III-1) to Formula (III-3):

[0052]

[0053] In Formula (III-3), the definition of R X1 is the same as that in Formula (I).

[0054] In Formula (III-1) to Formula (III-3), Y is selected from any one of a single bond, S or O; n is 0 or 1.

[0055] Wherein, when n = 0, it means that Y does not exist. When n = 1, it means connection through a single bond, O or S (forming a five-membered ring or a six-membered ring, etc. together with N on the parent nucleus).

[0056] R a 、R b 、R c 、R d 、R e and R f each independently represent unsubstituted, mono-substituted to the maximum allowable substitution; specifically, R a represents unsubstituted (R a is hydrogen), mono-substituted, di-substituted or tri-substituted; R b represents unsubstituted (R b is hydrogen), mono-substituted, di-substituted, tri-substituted or tetra-substituted; R c 、R d 、R e and R f are the same by analogy and will not be elaborated. When R a 、R b 、R c 、R d 、R e and R f represent multi-substituted (i.e., at least di-substituted), the multiple substituents are the same or different groups.

[0057] In some preferred embodiments, the R a 、R b 、R c 、R d 、R e and R fEach independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino.

[0058] In some preferred embodiments, the R a , R b , R c , R d , R e and R f The substituents of the substitution in are independently selected from deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C6 (such as C1, C2, C3, C4, C5, C6, 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, C20, etc.) aryl, C3-C20 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of one or at least two of them.

[0059] In some preferred embodiments, the R a , R b , R c , R d , R e and R f The substituents of the substitution in are independently selected from deuterium, halogen (such as F, Cl, Br, I), cyano, C1-C6 alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, etc.), C1-C6 deuterated alkyl (such as deuterated methyl, deuterated tert-butyl, etc.), C1-C6 haloalkyl (such as fluoromethyl, etc.), C3-C6 cycloalkyl (such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.), C6-C20 aryl (such as phenyl, fluorenyl, naphthyl, anthryl, phenanthryl, pyrenyl, etc.), C6-C20 deuterated aryl (such as deuterated phenyl, etc.), C6-C20 aryl substituted with C1-C6 alkyl (such as tert-butylphenyl, m-di-tert-butylphenyl, etc.), or C3-C20 heteroaryl (such as pyridyl, benzofuranyl, benzothiophenyl, etc.).

[0060] In some preferred embodiments, the R a , R b , R c , R d , R e , and R f are not connected or are connected by a chemical bond to form a ring between at least any two adjacent groups, and the R a , R b , R c , R d , R e , and R f are not connected or are connected by a chemical bond to form a ring with the adjacent ring structure.

[0061] In some preferred embodiments, the R a , R b , R c , R d , R e , and R f are each independently selected from hydrogen, deuterium, halogen, cyano, or any one of the following groups, where * represents the connection site of the group:

[0062]

[0063] In some preferred embodiments, the organoboron compound has a structure represented by any of the following:

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] Second, the present invention provides the use of the organoboron compound described in the first aspect above in the preparation of an organic electroluminescent device.

[0075] According to some preferred embodiments of the present invention, the organoboron compound is used as a doping material (also known as a fluorescent dye or a dye or a luminescent material or a dopant or a guest material) in the light-emitting layer of an organic electroluminescent device.

[0076] In some embodiments, the doping concentration (mass percentage) of the doping material relative to the host material in the light-emitting layer is 1 wt% to 20 wt%, for example, 1 wt%, 3 wt%, 5 wt%, 7 wt%, 9 wt%, 11 wt%, 13 wt%, 15 wt%, 17 wt%, 19 wt%, 20 wt% or any value therebetween.

[0077] In some embodiments, the doping concentration (mass percentage) of the doping material relative to the host material in the light-emitting layer is 1 wt% to 10 wt%, more preferably 2 wt% to 8 wt%.

[0078] In a third aspect, the present invention provides an organic electroluminescent device, including a light-emitting layer, and the doping material of the light-emitting layer contains the organoboron compound described in the first aspect of the present invention above.

[0079] 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.

[0080] 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.

[0081] In a fourth aspect, the present invention provides a display component / device, which includes the organoboron compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention.

[0082] The OLED device prepared by using the organoboron compound of the present invention has a low voltage and a long lifespan, and can meet the requirements of current panel manufacturing enterprises for high-performance materials.

[0083] The specific reason for the excellent performance of the organoboron 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:

[0084] The organic boron-containing compound provided by the present invention has the structure shown in formula (I). Through the fusion of a boron-containing heteroaromatic ring structure and a specific seven-membered spiro ring structure, the rigidity of the molecule and the intermolecular interaction force can be improved, so that the molecule exhibits excellent optoelectronic properties and high stability. The organic boron-containing compound is used in an organic electroluminescent device and can be used as a doping material for a light-emitting layer, which can effectively improve the light-emitting efficiency of the device, extend the service life of the device, reduce the voltage and energy consumption, and make the device have higher color purity. Detailed Embodiments

[0085] 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 claims.

[0086] Definition of Substituent Terms

[0087] The term "halogen or halide" used in the present invention includes fluorine, chlorine, bromine and iodine.

[0088] For the expression of chemical elements in the present invention, 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.

[0089] In the present invention, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure that can form a bond.

[0090] In the present invention, both "-*" and "*" represent the connection sites of groups.

[0091] In the present invention, "independently of each other" means that when its subject has a plurality, they can be the same or different from each other.

[0092] 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.

[0093] 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.

[0094] Any of C3-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0095] Any of C2-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0096] Any of C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0097] Any of C3-C30 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0098] As used herein, the term "alkyl" includes straight-chain and branched-chain alkyl groups. The alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Additionally, the alkyl group can be optionally substituted. Among the above, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, the alkyl group can be optionally substituted.

[0099] As used herein, the term "alkenyl" includes straight-chain, branched-chain or cyclic non-aromatic hydrocarbon groups having one or more carbon-carbon double bonds. The alkenyl group can be a straight-chain, branched-chain or cyclic non-aromatic hydrocarbon group having 2-20 carbon atoms and having one or more carbon-carbon double bonds, preferably an alkenyl group having 2-12 carbon atoms, including but not limited to vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, isobutenyl, butadienyl, 1-pentenyl, 2-pentenyl, isopentenyl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl or 1,3,5-hexatriene, etc. Additionally, the alkenyl group can be optionally substituted.

[0100] As used herein, the term "cycloalkyl" includes cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of the cycloalkyl group include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group can be optionally substituted.

[0101] As used herein, the term "heterocycloalkyl" can refer to a group formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), and exemplary examples include, but are not limited to: epoxy group, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxanyl, morpholinyl, etc.

[0102] As used herein, the term "aryl or aromatic group" includes non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, -yl, perylenyl, and azulyl, preferably phenyl, biphenyl, terphenyl, triphenylene, fluoranthenyl, and naphthyl. In addition, the aryl group can be optionally substituted. Examples of non-fused aryl groups include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl, and m-quaterphenyl. In addition, the aryl group can be optionally substituted.

[0103] As used herein, the term "heteroaryl" includes non-fused and fused heteroaromatic groups having 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Heteroaryl also refers to heteroaromatic group. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indolocarbazolyl, pyridoindolyl, pyrrolopyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxatriazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazinyl, indolyl, benzimidazolyl, indazolyl, indenoazinyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, xanthenyl, acridinyl, phenazinyl, phenothiazinyl, benzofuranopyridyl, furanodipyridyl, benzothiophenopyridyl, thiophenodipyridyl, benzoselenophenopyridyl, selenobenzodipyridyl, preferably dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridyl, triazinyl, benzimidazolyl, 1,2-azaborolanyl, 1,3-azaborolanyl, 1,4-azaborolanyl, borazolyl and their nitrogen analogs. Additionally, the heteroaryl may be optionally substituted.

[0104] As used herein, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocycloalkyl are the same as those described above. The alkoxy may be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy may be optionally substituted.

[0105] As used herein, the term "aryloxy" refers to a monovalent group formed by connecting the above-mentioned aryl group to O. The "heteroaryloxy" refers to a monovalent group formed by connecting the above-mentioned heteroaryl group to O. The "arylthio" refers to a monovalent group formed by connecting the above-mentioned aryl group to S. The "heteroarylthio" refers to a monovalent group formed by connecting the above-mentioned heteroaryl group to S.

[0106] As used herein, the term "alkylsilyl" covers silyl groups substituted by the groups exemplified in the above alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0107] As used herein, the term "aryl amino" refers to a monovalent group in which at least one hydrogen in -NH2 is substituted by the above aryl group, and includes, but is not limited to, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc. The "heteroaryl amino" refers to a monovalent group in which at least one hydrogen in -NH2 is substituted by the above heteroaryl group, and includes, but is not limited to, pyridylamino, pyrimidinylamino, dibenzofuranyl amino, etc.

[0108] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple (at least two) substituents, they may be the same or different substituents; when the same expression is involved above, it has the same meaning. Unless otherwise specified, the selection range of the substituents is as shown in the present invention and will not be elaborated herein.

[0109] It should be understood that when a molecular fragment is described as a substituent or otherwise connected to another part, its name can be written according to whether it is a fragment (such as phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the whole molecule (such as benzene, naphthalene, dibenzofuran). As used in the present invention, these different ways of specifying substituents or connecting fragments are considered equivalent.

[0110] In the compounds mentioned in the present invention, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the devices. In the compounds mentioned in the present invention, multiple substitutions refer to the range including double substitutions up to the maximum available substitutions. When a certain substituent in the compounds mentioned in the present invention represents multiple substitutions (including disubstitutions, trisubstitutions, tetrasubstitutions, etc.), it means that the substituent can exist at multiple available substitution positions on its connecting structure, and the substituent existing at multiple available substitution positions can be of the same structure or different structures.

[0111] In the compounds mentioned in the present invention, unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring, adjacent substituents in the compounds cannot be linked to form a ring. In the compounds mentioned 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, 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.

[0112] 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.

[0113] The materials described in the present invention as being usable for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed in the present invention can be combined 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 - 0101 of US Patent Application US2015 / 0349273M, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed in the present invention, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0114] In the examples of material synthesis, unless otherwise specified, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized products were subjected to structure confirmation and property testing using one or more conventional devices in the art (including but not limited to liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimators, etc. of Agilent), by methods well-known to those skilled in the art. In the examples of devices, the properties of the devices were also tested using conventional devices in the art (including but not limited to evaporation coaters produced by Nanjing Microelectronics Institute, optical testing systems and lifetime testing systems produced by Suzhou FushiDa, ellipsometers produced by Wuhan Yiguang Technology Co., Ltd., 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 testing methods, and can obtain the inherent data of the samples determinately and without interference, the above relevant content will not be elaborated further in the present invention.

[0115] 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:

[0116] Example 1: Synthesis of Compound I-16

[0117]

[0118] (1-1) Synthesis of Intermediate S1-1:

[0119] Under nitrogen protection, raw material M1-1 (22.59 g), raw material M1-2 (33.41 g), cesium carbonate (65.16 g) and DMF (400 mL) were added to a dry three-necked reaction flask. The mixture was slowly heated to 100 °C with stirring and reacted for 12 h. After the reaction solution was cooled to room temperature, water was added dropwise for crystallization. The precipitate was filtered, dried, and recrystallized to obtain Intermediate S1-1 (34.05 g, yield 65.5%).

[0120] (1-2) Synthesis of Intermediate S1-2:

[0121] Under nitrogen protection, add intermediate S1-1 (26.00 g) and tetrahydrofuran (150 mL) to a dry three-necked reaction flask. Cool the reaction solution to -78 °C, stir for 0.5 h, slowly dropwise add tert-butyllithium pentane solution (52.6 mL, 1.9 M), control the temperature to react at -78 °C for 1 h, and then dropwise add a solution of starting material M1-3 (10.40 g) in tetrahydrofuran (80 mL). After the addition is complete, slowly warm to room temperature and continue to react for 2 h. Then add saturated ammonium chloride solution (20 mL) to quench the reaction, dilute with water, separate the layers, extract the aqueous phase with dichloromethane (30 mL) three times, combine the organic phases, concentrate to remove the solvent to obtain an oily substance. Then add acetic acid (80 mL) and concentrated hydrochloric acid (16 mL), heat to 60 °C and react overnight. Cool, concentrate to remove the solvent, separate dichloromethane (40 mL) and water (40 mL), combine the organic phases, wash, dry, to obtain intermediate S1-2 (16.54 g, yield 52.3%).

[0122] (1-3) Synthesis of compound I-16:

[0123] Under nitrogen protection, add intermediate S1-2 (6.32 g) and anhydrous xylene (150 mL) to a dry three-necked reaction flask. Cool to -78 °C, slowly dropwise add tert-butyllithium pentane solution (12.5 mL, 1.6 M), and then slowly warm to 60 °C and react for 3 h. Stop heating, cool to -78 °C, add boron tribromide (2.4 mL), and restore to room temperature and react for 6 h. Then cool to 0 °C and dropwise add N,N-diisopropylethylamine (7.0 mL). After the addition is complete, warm to 150 °C and react for 15 h. After the reaction is complete, cool to room temperature, wash with water, separate the layers, dry, concentrate, perform column chromatography, and recrystallize to obtain compound I-16 (1.32 g, yield 21.8%).

[0124] MS (m / e) of compound I-16: 606.11; 1 HNMR (400 MHz, CDCl3): δ 8.16 - 8.05 (m, 4H), 7.67 - 7.64 (m, 1H), 7.46 - 7.06 (m, 18H), 2.99 - 2.90 (m, 4H).

[0125] Example 2: Synthesis of compound I-78

[0126]

[0127] (2-1) Synthesis of intermediate S2-1:

[0128] Under nitrogen protection, raw material M2-1 (26.78 g), raw material M2-2 (14.91 g), sodium tert-butoxide (19.22 g), Pd2(dba)3 (1.83 g), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (3.81 g) and toluene (300 mL) were added to a dry three-necked reaction bottle, and the temperature was slowly raised to 100°C under stirring for 5 h. After the reaction solution was cooled, water (100 mL) was added, washed with water, concentrated, column chromatographed, recrystallized, and dried to obtain intermediate S2-1 (21.33 g, yield 63.3%).

[0129] (2-2) Synthesis of intermediate S2-2:

[0130] Under nitrogen protection, add intermediate S2-1 (16.85g), raw material M2-3 (16.49g), sodium tert-butoxide (9.61g), Pd2(dba)3 (0.92g), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.91g) and toluene (200mL) to a dry three-necked reaction bottle, slowly heat to 95°C under stirring and react for 8h. After the reaction solution is cooled, water (100mL) is added, washed with water, concentrated, column chromatographed, recrystallized, and dried to obtain intermediate S2-2 (17.81g, yield 66.1%).

[0131] (2-3) Synthesis of intermediate S2-3:

[0132] Under nitrogen protection, add intermediate S2-2 (21.56 g) and tetrahydrofuran (120 mL) to a dry three-necked reaction bottle, cool the reaction solution to -78 ° C, stir for 0.5 h, slowly drop tert-butyl lithium pentane solution (42.1 mL, 1.9 M), control the temperature at -78 ° C for 1 h, and then drop the raw material M1-3 (8.32 g) in tetrahydrofuran (60 mL) solution. After the addition is complete, slowly warm to room temperature and continue to react for 2 h. Then add saturated ammonium chloride solution (20 mL) to quench the reaction, dilute with water, separate the liquids, extract the aqueous phase with dichloromethane (30 mL) three times, combine the organic phases, concentrate and remove the solvent to obtain an oily substance, then add acetic acid (80 mL) and concentrated hydrochloric acid (16 mL), heat to 60 ° C and react overnight. The mixture was cooled and concentrated to remove the solvent. The mixture was separated by dichloromethane (40 mL) and water (40 mL). The organic phases were combined, washed and dried to obtain intermediate S2-3 (13.51 g, yield 56.0%).

[0133] (2-4) Synthesis of intermediate S2-4:

[0134] Under nitrogen protection, add intermediate S2-3 (12.06 g), raw material M2-4 (8.23 g), sodium tert-butoxide (3.84 g), Pd2(dba)3 (0.37 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.76 g) and toluene (170 mL) into a dry three-necked reaction flask. Slowly heat up to 105 °C with stirring and react for 10 h. After the reaction solution is cooled, add water (100 mL), wash with water, concentrate, carry out column chromatography, recrystallize, and dry to obtain intermediate S2-4 (11.59 g, yield 62.0%).

[0135] (2-5) Synthesis of compound I-78:

[0136] Under nitrogen protection, add intermediate S2-4 (9.35 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 react at room temperature for 6 h. Then cool down to 0 °C and dropwise add N,N-diisopropylethylamine (7.0 mL). After the addition is complete, heat up to 150 °C and react for 15 h. After the reaction is completed, cool to room temperature, wash with water, separate the liquid, dry, concentrate, carry out column chromatography, and recrystallize to obtain compound I-78 (1.42 g, yield 15.6%).

[0137] MS (m / e) of compound I-78: 908.84; 1 1H NMR (400 MHz, CDCl3): δ 7.64 - 7.58 (m, 2H), 7.38 - 6.97 (m, 24H), 6.83 (d, 1H), 3.00 - 2.88 (m, 4H), 1.84 - 1.74 (m, 2H), 1.69 - 1.59 (m, 2H), 1.34 (s, 18H), 1.30 (d, 12H).

[0138] Example 3: Synthesis of compound I-87

[0139]

[0140] The synthesis route of compound I-87 is the same as that of compound I-78. Only replace raw material M2-4 with raw material M3-1 to obtain compound I-87.

[0141] MS (m / e) of compound I-87: 986.23; 1HNMR(400MHz, CDCl3): δ 7.80 (d, 1H), 7.62 (dd, 1H), 7.54 - 7.48 (m, 2H), 7.42 - 6.97 (m, 26H), 6.83 (d, 1H), 3.00 - 2.88 (m, 4H), 1.34 (d, 36H).

[0142] Example 4: Synthesis of Compound I-108

[0143]

[0144] (4-1) Synthesis of Raw Material M4-1:

[0145] Under nitrogen protection, add raw material M2-2 (7.46 g), raw material M4-1a (14.80 g), sodium tert-butoxide (9.61 g), Pd2(dba)3 (0.92 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.91 g) and toluene (200 mL) into a dry three-necked reaction flask. Slowly heat the mixture to 106 °C with stirring and react for 5 h. After the reaction solution is cooled, add water (120 mL), wash with water, concentrate, perform column chromatography, recrystallize, and dry to obtain raw material M4-1 (11.34 g, yield 62.1%).

[0146] (4-2) Synthesis of Compound I-108:

[0147] The synthesis route of Compound I-108 is the same as that of Compound I-78. Only by replacing raw material M2-4 with raw material M4-1 can Compound I-108 be obtained.

[0148] MS (m / e) of Compound I-108: 862.67; 1 HNMR(400MHz, CDCl3): δ 8.07 (d, 1H), 8.00 - 7.89 (m, 2H), 7.71 (d, 1H), 7.55 - 7.44 (m, 3H), 7.43 - 6.96 (m, 21H), 6.81 (d, 1H), 2.99 - 2.90 (m, 4H), 1.34 (s, 18H).

[0149] Example 5: Synthesis of Compound I-123

[0150]

[0151] The synthesis route of Compound I-123 is the same as that of Compound I-78. Only by replacing raw material M2-4 with raw material M5-1 can Compound I-123 be obtained.

[0152] MS (m / e) of Compound I-123: 887.06; 1HNMR (400 MHz, CDCl3): δ 8.04 - 8.01 (m, 1H), 7.70 - 7.66 (m, 1H), 7.53 - 7.01 (m, 29H), 6.83 (d, 1H), 3.00 - 2.88 (m, 4H), 1.34 (d, 18H).

[0153] Example 6: Synthesis of Compound I-145

[0154]

[0155] The synthetic route of Compound I-145 is the same as that of Compound I-78. Only by replacing raw material M2-1 with raw material M6-1, raw material M2-3 with raw material M6-2, and raw material M2-4 with raw material M6-3 can Compound I-145 be obtained.

[0156] MS (m / e) of Compound I-145: 908.83; 1 HNMR (400 MHz, CDCl3): δ 7.62 - 7.57 (m, 2H), 7.54 (dd, 1H), 7.48 - 7.33 (m, 5H), 7.31 - 6.93 (m, 18H), 6.83 (d, 1H), 3.00 - 2.88 (m, 4H), 1.84 - 1.73 (m, 2H), 1.68 - 1.57 (m, 2H), 1.34 (s, 18H), 1.30 (d, 12H).

[0157] Example 7: Synthesis of Compound I-150

[0158]

[0159] The synthetic route of Compound I-150 is the same as that of Compound I-78. Only by replacing raw material M1-3 with raw material M7-1 and raw material M2-4 with raw material M6-3 can Compound I-150 be obtained.

[0160] MS (m / e) of Compound I-150: 932.67; 1 HNMR (400 MHz, CDCl3): δ 7.86 - 7.71 (m, 4H), 7.52 - 7.43 (m, 8H), 7.38 - 7.27 (m, 3H), 7.24 - 7.10 (m, 7H), 7.06 - 6.93 (m, 4H), 6.83 (d, 1H), 3.08 - 2.96 (m, 4H), 1.84 - 1.73 (m, 2H), 1.68 - 1.57 (m, 2H), 1.34 (s, 18H), 1.30 (d, 12H).

[0161] Example 8: Synthesis of Compound II-1

[0162]

[0163] (8-1) Synthesis of Intermediate S8-1:

[0164] The synthesis route of Intermediate S8-1 is the same as that of Intermediate S2-1. Only by replacing raw material M2-1 with raw material M8-1 and raw material M2-2 with raw material M8-2 can Intermediate S8-1 be obtained.

[0165] (8-2) Synthesis of Intermediate S8-2:

[0166] The synthesis route of Intermediate S8-2 is the same as that of Intermediate S2-3. Only by replacing Intermediate S2-2 with Intermediate S8-1 and raw material M1-3 with raw material M8-3 can Intermediate S8-2 be obtained.

[0167] (8-3) Synthesis of Intermediate S8-3:

[0168] Add Intermediate S8-2 (24.26 g), raw material M8-4 (4.70 g), potassium carbonate (20.73 g) and NMP (180 mL) to a dry three-necked reaction flask. Heat up to 100 °C and react for 12 h. After the reaction is completed, cool down to room temperature, perform vacuum distillation, add water (100 mL) and toluene (100 mL), separate the layers and then perform vacuum distillation, and carry out column chromatography to obtain Intermediate S8-3 (22.37 g, yield 80.0%).

[0169] (8-4) Synthesis of Compound II-1:

[0170] The synthesis route of Compound II-1 is the same as that of Compound I-16. Only by replacing Intermediate S1-2 with Intermediate S8-3 can Compound II-1 be obtained.

[0171] MS (m / e) of Compound II-1: 533.87; 1 HNMR (400 MHz, CDCl3): δ 7.55 (dd, 1H), 7.50 - 7.36 (m, 5H), 7.34 - 6.97 (m, 16H), 6.91 (dd, 1H), 6.63 (d, 1H).

[0172] Example 9: Synthesis of Compound II-117

[0173]

[0174] The synthetic route of compound II-117 is the same as that of compound I-78. By simply replacing raw material M2-2 with raw material M9-1, raw material M1-3 with raw material M8-3, and raw material M2-4 with raw material M6-3, compound II-117 can be obtained.

[0175] MS (m / e) of compound II-117: 884.68; 1 HNMR (400 MHz, CDCl3): δ 7.45 (dd, 2H), 7.42 - 7.37 (m, 2H), 7.34 - 7.02 (m, 19H), 6.82 (d, 1H), 1.85 - 1.74 (m, 4H), 1.69 - 1.57 (m, 4H), 1.34 (s, 9H), 1.30 (d, 24H).

[0176] Example 10: Synthesis of compound II-131

[0177]

[0178]

[0179] (10-1) Synthesis of intermediate S10-2:

[0180] The synthetic route of intermediate S10-2 is the same as that of intermediate S2-2. By simply replacing raw material M2-1 with raw material M10-1, intermediate S10-2 can be obtained.

[0181] (10-2) Synthesis of intermediate S10-3:

[0182] The synthetic route of intermediate S10-3 is the same as that of intermediate S8-2. By simply replacing intermediate S8-1 with intermediate S10-2, intermediate S10-3 can be obtained.

[0183] (10-3) Synthesis of intermediate S10-4:

[0184] Under nitrogen protection, add intermediate S10-3 (27.06 g), raw material M10-2 (15.66 g), cesium carbonate (32.58 g) and DMF (300 mL) to a dry three-necked reaction flask. Stir and slowly heat to 110 °C for reaction for 8 h; after the reaction solution cools to room temperature, add water dropwise to crystallize, filter, dry, and recrystallize to obtain intermediate S10-4 (24.99 g, yield 59.9%).

[0185] (10-4) Synthesis of compound II-131

[0186] The synthetic route of compound II-131 is the same as that of compound I-16. By simply replacing intermediate S1-2 with intermediate S10-4, compound II-131 can be obtained.

[0187] MS (m / e) of compound II-131: 808.73; 1 HNMR (400 MHz, CDCl3): δ 8.75 (d, 1H), 8.12 (s, 1H), 8.01 (dt, 1H), 7.56 (dd, 1H), 7.52 - 7.02 (m, 23H), 1.34 (d, 18H).

[0188] Example 11: Synthesis of compound I-13

[0189]

[0190] (11-1) Synthesis of intermediate S11-1:

[0191] The synthetic route of intermediate S11-1 is the same as that of intermediate S8-2. By simply replacing raw material M8-3 with raw material M1-3, intermediate S11-1 can be obtained.

[0192] (11-2) Synthesis of compound I-13:

[0193] The synthetic route of compound I-13 is the same as that of compound II-131. By simply replacing intermediate S10-3 with intermediate S11-1 and raw material M10-2 with raw material M1-2, compound I-13 can be obtained.

[0194] MS (m / e) of compound I-13: 608.52; 1 HNMR (400 MHz, CDCl3): δ 8.20 - 8.13 (m, 1H), 8.10 (dd, 1H), 7.69 - 7.63 (m, 1H), 7.50 (dd, 1H) 7.35 (dd, 1H), 7.33 - 7.24 (m, 8H), 7.23 - 7.02 (m, 12H), 3.00 - 2.88 (m, 4H).

[0195] Example 12: Synthesis of compound I-155

[0196]

[0197] The synthetic route of compound I-155 is the same as that of compound I-13. By simply replacing raw material M1-2 with raw material M12-1, compound I-155 can be obtained.

[0198] MS (m / e) of compound I-155: 720.14; 11H NMR (400 MHz, CDCl3): δ 8.33 (d, 1H), 7.92 (d, 1H), 7.61 (d, 1H), 7.50 (dd, 1H), 7.34 - 7.02 (m, 19H), 2.99 - 2.90 (m, 4H), 1.35 (d, 18H).

[0199] Exemplary specific synthesis methods of the above several compounds are given in the present invention. For 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. Alternatively, those skilled in the art can also prepare them by other methods in the prior art.

[0200] Device Example 1

[0201] An organic electroluminescent device is prepared as follows: Clean a glass substrate having an indium tin oxide (ITO) anode with a thickness of 120 nm, and then treat it with UV ozone and oxygen plasma. After treatment, dry the substrate in a glove box filled with nitrogen to remove moisture, and then mount the substrate on a substrate holder and place it in a vacuum chamber. The following specified organic layers are sequentially evaporated onto the ITO anode by thermal vacuum at a rate of -8 under a vacuum of about 10 Torr. Compounds HT and HI (weight ratio 97:3) are co-evaporated and used 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, BH as the blue light host and Compound I-16 as the doping material (weight ratio 98:2) are co-evaporated and used as the emitting layer (EML) with a thickness of Compound HB is used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, 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, thickness of lithium 8-hydroxyquinolate (Liq) is evaporated as the electron injection layer (EIL), and aluminum of

[0202] Device Examples 2 - 12, Device Comparative Examples 1 - 2

[0203] An organic electroluminescent device, which is only different from Device Example 1 in 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.

[0204] The molecular structural formulas of the related materials are as follows:

[0205]

[0206] Among them, Ref-1 and Ref-2 are prepared according to the preparation methods in CN117567490A.

[0207] 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 a better presentation of the data comparison, the voltage, external quantum efficiency, and lifetime of Device Comparative Example 1 are set to 100% respectively, and the voltage, efficiency, and lifetime data of other devices are converted relative to the corresponding data of Device Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0208] The color purity of the doping material can be characterized by the full width at half maximum (FWHM, nm) of the fluorescence emission spectrum: Using a fluorescence spectrometer F7000, the room temperature fluorescence spectrum of a 0.01 g / mL toluene solution is measured with an excitation wavelength of 365 nm, and the relevant data can be directly read from the spectrum.

[0209] Table 1

[0210] Device Doped material Voltage (V) EQE Lifetime (h) Full width at half maximum (nm) Device Example 1 I-16 94％ 113％ 117％ 22 Device Example 2 I-78 93％ 117％ 121％ 21 Device Example 3 I-87 92％ 120％ 123％ 20 Device Example 4 I-108 93％ 118％ 120％ 21 Device Example 5 I-123 92％ 115％ 119％ 21 Device Example 6 I-145 94％ 116％ 116％ 22 Device Example 7 I-150 95％ 119％ 114％ 22 Device Example 8 II-1 96％ 109％ 110％ 23 Device Example 9 II-117 96％ 112％ 115％ 22 Device Example 10 II-131 95％ 114％ 118％ 21 Device Example 11 I-13 94％ 111％ 115％ 22 Device Example 12 I-155 93％ 117％ 118％ 22 Device Comparative Example 1 Ref-1 100％ 100％ 100％ 28 Device Comparative Example 2 Ref-2 102％ 101％ 102％ 27

[0211] As shown in Table 1, at a current density of 10 mA / cm 2 For Device Examples 1-12 compared with Device Comparative Examples 1-2, the voltage can be reduced by 4-10%, the external quantum efficiency can be increased by 8%-20%, and the device lifetime can be extended, with the maximum extension of 23%. The above data show that the device prepared with the organic boron-containing compound provided by the present invention has a lower driving voltage, higher current efficiency and lifetime, and higher color purity.

[0212] 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 apparent 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 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 regarding why the present invention works are not intended to be restrictive.

Claims

1. An organoboron compound having the structure shown in formula (I): In formula (I), 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 are connected into a ring through a chemical bond; A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from N or CR1; U1, U2, U3, U4, U5, U6, U7, U8, U9, U 10 , U 11 , U 12 , U 13 , U 14 are each independently selected from N or CR2; R1 and R2 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino. Among them, at least two adjacent groups of R1 and R2 are not connected or are connected by a chemical bond to form a ring, and R1, R2 are not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; The substituents in said R1, R2, 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, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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; Represents a single bond or a double bond.

2. The organoboron compound according to claim 1, wherein The organoboron compound has the structure represented by any one of formula (II-1) to formula (II-3): In formulas (II-1) to (II-3), A1 to A8, U1 to U 14 , R X1 are as defined in formula (I).

3. The organoboron compound according to claim 1 or 2, wherein The R X1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; The R X1 The substituents described therein are 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; The R X1 is not connected to the adjacent ring structure or is connected into a ring through a chemical bond; Preferably, the R X1 is selected from any of the following groups, where * represents the attachment site of the group:

4. The organic boron-containing compound according to claim 2, wherein In formula (II-1) to formula (II-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 CR1; More preferably, A1, A4, A5, A8 are selected from CH, and A2, A3, A6, A7 are each independently selected from CR1; Preferably, each R1 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino. Preferably 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 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino; The substituents of the substituted R1 are independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, C3-C20 heteroaryl; More preferably, each R1 is independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, where * represents the attachment site of the group: -CH3, -CD3, -CF3, Preferably, at least two adjacent R1 are not connected or are connected by a chemical bond to form a ring.

5. The organoboron compound according to any one of claims 1-4, characterized in that, At most one of U1, U2, U3, U4 is selected from N; And / or at most one of U5, U6, U7, U8 is selected from N; and / or U9, U 10 , U 11 , U 12 At most one of them is selected from N; and / or U 13 、U 14 At most one of them is selected from N; Preferably, U1, U2, U3, U4, U5, U6, U7, U8, U9, U 10 、U 11 、U 12 、U 13 、U 14 are each independently selected from CR2; Preferably, U4, U5, U 12 , U 13 , U 14 are CH, and U1, U2, U3, U6, U7, U8, U9, U 10 , U 11 are each independently selected from CR2; Preferably, each of the R2s independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted 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 C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; The substituents of the substituted R2s are independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; More preferably, each of said R2 is independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, * represents the connection site of the group: *-CH3, *-CD3, *-CF3, Preferably, at least two adjacent R2s are not connected or are connected by a chemical bond to form a ring.

6. The organoboron compound according to any one of claims 1-5, characterized in that, The organoboron compound has a structure represented by any one of formulas (III-1) to (III-3): In formula (III-3), R X1 is defined in the same way as in formula (I); In formulas (III-1) to (III-3), Y is selected from any one of a single bond, S, and O; n is 0 or 1; R a 、R b 、R c 、R d 、R e and R f each independently represents unsubstituted, mono-substituted to the maximum allowable substitution; Preferably, the R a , R b , R c , R d , R e , and R f are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino. The said R a , R b , R c , R d , R e and R f The substituents described in are independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; The R a , R b , R c , R d , R e and R f Among any at least two adjacent groups, they are not connected or are connected by a chemical bond to form a ring. The R a , R b , R c , R d , R e and R f are not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; Preferably, the R a , R b , R c , R d , R e and R f are each independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, where * represents the attachment site of the group: *-CH3, *-CD3, *-CF3, 7. The organoboron compound according to any one of claims 1-6, characterized in that, The organoboron compound has a structure represented by any of the following:

8. Use of the organoboron compound according to any one of claims 1-7 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; Preferably, the doping concentration of the doping material is 1 wt% to 20 wt%, preferably 1 wt% to 10 wt%, more preferably 2 wt% to 8 wt% relative to the host material in the light-emitting layer.

9. An organic electroluminescent device, comprising a light-emitting layer, wherein the doping material of the light-emitting layer contains the organoboron compound according to any one of claims 1-7; Preferably, the organic electroluminescent device includes: An anode, a cathode, and a light-emitting layer disposed between the anode and the cathode; Preferably, the light-emitting layer includes a doping material; Preferably, 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.

10. A display component / device, which includes the compound according to any one of claims 1-7 or the organic electroluminescent device according to claim 9.

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