Organic boron-containing compound and application thereof

Abstract

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

Description

Technical Field

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

[0002] Organic electroluminescent displays are known as the "third display technology revolution" because of their advantages, including self-luminescence, wide viewing angle, high contrast, fast response, low power consumption, lighter and thinner design, and flexible display. They are widely used in display and lighting fields such as mobile phones, televisions, computers, and cars.

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

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

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

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

[0007]

[0008] In formula (I), M is selected from C, Si, Ge or Sn;

[0009] X1 and X2 are each independently selected from O, S, Se, NR X1 , CR X2 R X3 or SiRX4 R X5 ;

[0010] Y1 and Y2 are each independently selected from O, S, Se, NR Y1 , CR Y2 R Y3 or SiR Y4 R Y5 ;

[0011] R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 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; the R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds;

[0012] A1, A2, A3, A4, A5, A6 are each independently selected from N or CR A ;

[0013] U1, U2, U3 are each independently selected from N or CR U ;

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

[0015] R A 、R U 、R ZEach is 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, substituted or unsubstituted C3-C30 heteroaryl; the adjacent R A They are not connected or connected to form a ring through chemical bonds; the adjacent R U They are not connected or connected to form a ring through chemical bonds; the adjacent R Z They are not connected or connected to form a ring through chemical bonds;

[0016] R A 、R U 、R Z 、R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 The substituents substituted in the above-mentioned group are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxyl, ester, 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, or a combination of at least two thereof.

[0017] In the present invention, R X1 The adjacent groups are connected to form a ring through chemical bonds. X1 It is not only connected to the N atom by a chemical bond, but also connected to the adjacent groups (such as A1 or A6 or U1 or U3) by a chemical bond (such as a single bond, a double bond, O or S, etc.), thereby forming a fused ring structure. X2 、R X3 、R X4 、R X5 、RY1 、R Y2 、R Y3 、R Y4 、R Y5 The same applies to the descriptions below. When the same descriptions are mentioned below, they have the same meaning and will not be repeated one by one.

[0018] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, the fundamental reason for achieving good performance is the optimized combination of the entire molecular structure and the synergistic effects of the various groups, rather than the effects of a single group / feature.

[0019] The following are preferred technical solutions of the present invention, but are not intended to 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 and realized.

[0020] In some preferred embodiments, X1 and X2 are each independently selected from O, S or NR X1 , R X1 The definitions of are the same as those in formula (I).

[0021] In some preferred embodiments, the organic boron-containing compound has a structure as shown in any one of Formula (II-1) to Formula (II-6):

[0022]

[0023] In formula (II-1) to formula (II-6), A1 to A6, U1 to U3, M, Y1 to Y2, Z1 to Z6, R X1 The definitions of are the same as those in formula (I).

[0024] In some preferred embodiments, at most one (e.g., 0 or 1) of Z1, Z2, and Z3 is selected from N, and the rest are independently selected from CR Z and / or at most one (eg, 0 or 1) of Z4, Z5, and Z6 is selected from N, and the rest are independently selected from CR Z .

[0025] In some preferred embodiments, Z1, Z2, Z3, Z4, Z5, and Z6 are each independently selected from CR Z Multiple (e.g. 2, 3, 4, 5, 6) CRs Z R in Z are the same or different groups.

[0026] In some preferred embodiments, the number of CH in Z1, Z2, Z3, Z4, Z5, and Z6 is 1-6 (e.g., 1, 2, 3, 4, 5, 6).

[0027] In some preferred embodiments, Z1, Z2, Z5, and Z6 are CH, and Z3 and Z4 are each independently selected from CR Z .

[0028] In some preferred embodiments, R Z Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., 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. Preferably, R Z Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl; More preferably, the R Z Each is independently selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl or phenyl.

[0029] In some preferred embodiments, Z1, Z2, Z3, Z4, Z5, and Z6 are all selected from CH.

[0030] In some preferred embodiments, Y1 and Y2 are each independently selected from O, S, NR Y1 or CR Y2 R Y3 , R Y1 、R Y2 、R Y3 The definitions of are the same as those in formula (I).

[0031] In some preferred embodiments, R Y1 Each is independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and 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.

[0032] Among them, the R Y1The substituents substituted in the alkyl group are each independently selected from 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., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two thereof.

[0033] In some preferred embodiments, the R Y1 Any one of the following groups, substituted or unsubstituted, is selected from: phenyl, biphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, benzofluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl; wherein R Y1 The substituents substituted in the above formula (I) are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, and pyridyl.

[0034] In some preferred embodiments, the R Y1 Select any of the following groups, * represents the attachment site of the group:

[0035]

[0036] In some preferred embodiments, the R Y1 It is not connected to Z1 or Z6 or is connected to form a ring through a chemical bond (such as a single bond, a double bond, O or S, etc.). For example, it has any of the following structures:

[0037]

[0038]

[0039] In formula (III-1) to formula (III-6), A1, A2, A3, A4, A5, A6, U1, U1, U3, M, Z2, Z3, Z4, Z5 and R X1 The definitions of are the same as those in formula (I).

[0040] In some preferred embodiments, RY2 、R Y3 Each is independently selected from any one of substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and 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;

[0041] Among them, the R Y2 、R Y3 The substituents substituted in the alkyl group are each independently selected from 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., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two thereof.

[0042] In some preferred embodiments, the R Y2 、R Y3 Each independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, phenyl, biphenyl, naphthyl, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl; wherein said R Y2 、R Y3 The substituents substituted in the above formula (I) are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, naphthyl, and pyridyl.

[0043] In some preferred embodiments, the R Y2 、R Y3 Each is independently selected from methyl or phenyl.

[0044] In some preferred embodiments, M is selected from C or Si; preferably, M is selected from C.

[0045] In some preferred embodiments, at most one (e.g., 0 or 1) of A1, A2, and A3 is selected from N, and the rest are independently selected from CR A and / or A4, A5, A6 have at most 1 (eg 0 or 1) selected from N, and the rest are independently selected from CR A .

[0046] In some preferred embodiments, A1, A2, A3, A4, A5, and A6 are each independently selected from CR A Multiple (e.g. 2, 3, 4, 5, 6) CRs A R in A are the same or different groups.

[0047] In some preferred embodiments, the number of CH in A1, A2, A3, A4, A5, and A6 is 1-6 (e.g., 1, 2, 3, 4, 5, 6).

[0048] In some preferred embodiments, A2, A3, A4, and A5 are CH, and A1 and A6 are each independently selected from CR A .

[0049] In some preferred embodiments, R A Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., 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; preferably, the R A Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl; More preferably, the R A Each is independently selected from hydrogen, deuterium, methyl, deuterated methyl, tert-butyl or phenyl.

[0050] In some preferred embodiments, A1, A2, A3, A4, A5, and A6 are all selected from CH.

[0051] In some preferred embodiments, R X1 It is not connected to A1 or A6 or is connected to form a ring through a chemical bond (such as a single bond, double bond, O or S, etc.).

[0052] In some preferred embodiments, RX1 Each is independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and 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.

[0053] Among them, the R X1 The substituents substituted in the alkyl group are each independently selected from 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., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two thereof.

[0054] In some preferred embodiments, the R X1 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, pyridylphenyl, pyridyl, phenylpyridyl, bipyridyl, benzoheteroanthryl, benzothioxanthenyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; wherein R X1 The substituents substituted in the above-mentioned group are each independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindanyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, dibenzofuranyl, and dibenzothiophenyl.

[0055] Specifically, the two combined substituted substituents may include, for example, deuterated alkyl formed by a combination of alkyl and deuterium (e.g., deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, etc.); halogenated alkyl formed by a combination of halogen and alkyl (e.g., trifluoromethyl, etc.); deuterated aryl formed by a combination of aryl and deuterium (e.g., deuterated phenyl, etc.); alkyl-substituted aryl formed by a combination of alkyl and aryl (e.g., tert-butylphenyl, 2,2-dimethyl-1,3-dihydroindenyl, 1,1,3,3-tetramethyl-2,3-dihydroindenyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, etc.) or aryl-substituted alkyl (e.g., tert-butyl substituted with phenyl, etc.). The following descriptions have the same meaning when they are related to the same descriptions, and they will not be repeated one by one.

[0056] In some preferred embodiments, the R X1 Each is independently selected from any of the following groups, * represents the attachment site of the group:

[0057] In some preferred embodiments, at most one (e.g., 0 or 1) of U1, U2, and U3 is selected from N, and the rest are independently selected from CR U .

[0058] In some preferred embodiments, U1, U2, and U3 are each independently selected from CR U Multiple (e.g. 2 or 3) CRs U R in U are the same or different groups.

[0059] In some preferred embodiments, the number of CHs in U1, U2, and U3 is 1-3 (eg, 1, 2, 3).

[0060] In some preferred embodiments, U1 and U3 are CH, and U2 is selected from CR U .

[0061] In some preferred embodiments, R Uand each 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., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C any one of a 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, a substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, or a 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, the adjacent R U They are not connected or connected to form a ring through chemical bonds.

[0062] Among them, the R U The substituents substituted in the alkyl group are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, or C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.

[0063] In some preferred embodiments, the R UEach is independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, tetrahydropyrrolyl, tetrahydropyranyl, phenyl, biphenyl, terphenyl, 2,3-dihydroindanyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, (wherein Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, pyridyl, dibenzofuranyl, and dibenzothiophenyl); wherein the R U The substituents substituted in the above-mentioned group are each independently selected from any one of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, dibenzofuranyl and dibenzothiophenyl.

[0064] In some preferred embodiments, the R U Each is independently selected from hydrogen, deuterium, halogen, cyano or any of the following groups, * represents the attachment site of the group:

[0065]

[0066] In some preferred embodiments, adjacent R U They are not connected or are connected by chemical bonds to form a substituted or unsubstituted C3-C10 (for example, C4, C5, C6, C7, C8, C9, etc.) alicyclic ring, a substituted or unsubstituted C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring or a substituted or unsubstituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring.

[0067] In some preferred embodiments, the substituents substituted in the above-mentioned rings are each independently selected from any one or a combination of at least two of deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C3-C8 (e.g., C4, C5, C6, C7, etc.) cycloalkyl, C6-C12 (e.g., C6, C9, C10, etc.) aryl, C3-C12 (e.g., C3, C4, C5, C6, C9, C10, etc.) heteroaryl.

[0068] In some preferred embodiments, adjacent R U They are not connected or connected to form a ring (e.g. etc., with dotted lines representing fused bonds). wherein the ring is optionally substituted with any one or more substituents selected from deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0069] In some preferred embodiments, the organic boron-containing compound has a structure as shown in Formula (II-1), Formula (II-3) or Formula (II-6), more preferably a structure as shown in Formula (II-6).

[0070] In some embodiments, the organic boron-containing compound of the present invention has any of the following structures:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] In a second aspect, the present invention provides a use of the organic boron-containing compound as described in the first aspect in preparing an organic electroluminescent device.

[0086] In some preferred embodiments, the organic boron-containing compound is used as a doping material (also known as a dopant or fluorescent dye or dye or luminescent material) of a light-emitting layer in an organic electroluminescent device.

[0087] In some preferred embodiments, the doping concentration (mass percentage) of the doping material relative to the main material in the light-emitting layer is 1wt% to 20wt% (for example, 2wt%, 3wt%, 4wt%, 5wt%, 6wt%, 7wt%, 8wt%, 9wt%, 10wt%, 11wt%, 12wt%, 13wt%, 14wt%, 15wt%, 16wt%, 17wt%, 18wt% or 19wt%), preferably 1wt% to 15wt%, and more preferably 2wt% to 10wt%.

[0088] In a third aspect, the present invention provides an organic electroluminescent device comprising a light-emitting layer, wherein the doping material of the light-emitting layer comprises at least one organic boron-containing compound as described in the first aspect.

[0089] In some preferred embodiments, the organic electroluminescent device comprises: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In some preferred embodiments, the light-emitting layer further comprises a host material.

[0090] In some preferred embodiments, the organic electroluminescent device further comprises any 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.

[0091] In a fourth aspect, the present invention provides a display component / device comprising at least one of the organic boron-containing compound according to the first aspect or the organic electroluminescent device according to the third aspect.

[0092] The organic electroluminescent device prepared by using the organic boron-containing compound of the present invention has low voltage and long life, and can meet the requirements of current panel manufacturing companies for high-performance materials.

[0093] The specific reasons why the above-mentioned organic boron-containing compound of the present invention has excellent performance as a dopant material in the light-emitting layer of an organic electroluminescent device are still unclear. It is speculated that the reasons may be as follows:

[0094] The organic compound provided by the present invention has a structure as shown in formula (I), which has a double six-membered ring structure, can enhance the overall molecular conjugation, and is applied to the light-emitting layer of an organic electroluminescent device, thereby improving the efficiency and life of the device. DETAILED DESCRIPTION

[0095] The technical solutions of the present invention are described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention. Any other equivalent changes or modifications that do not depart from the spirit disclosed by the present invention should be included in the scope of the claims.

[0096] Definition of Substituent Terms

[0097] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine.

[0098] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0099] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom of the heterocycloalkyl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom of the alicyclic heterocycle is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0100] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0101] In the present invention, “*” indicates the attachment site of the group.

[0102] In the present invention, “each independently” means that when there are multiple subjects, they may be the same or different.

[0103] In the present invention, the expression Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0104] 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.

[0105] In the present invention, the C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0106] 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.

[0107] In the present invention, the C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0108] In the present invention, the C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0109] In the present invention, unless otherwise specified, the C6-C30 aryl group (C6-C30 aromatic ring) includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means a group containing at least one phenyl group, and when containing at least two phenyl groups, the phenyl groups are connected by a single bond, including but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed ring aryl group means a group containing at least two rings (and at least one ring is an aromatic ring), and the rings share two adjacent carbon atoms and are condensed to each other, for example The fluorenyl radical includes, but is not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that monocyclic aromatic groups and condensed aromatic groups connected by a single bond also fall within the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0110] In the present invention, unless otherwise specified, the C3-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes a monocyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and the other group are connected by a single bond, and illustratively include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two groups share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, benzonaphthofuranyl (benzo[B]naphtho[2,3-D]furanyl, benzo[B]naphtho[1,2-D] [B] naphtho[2,1-D]thiophenyl), carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.

[0111] In the present invention, specific examples of the C6-C30 arylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0112] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups with O.

[0113] In the present invention, the C6-C30 arylthio group is a monovalent group formed by connecting the above-mentioned aryl groups and S, and the C3-C30 heteroarylthio group is a monovalent group formed by connecting the above-mentioned heteroaryl groups and S.

[0114] In the present invention, the C3-C10 alicyclic ring, preferably the C4-C10 alicyclic ring, includes a saturated alicyclic ring or an unsaturated alicyclic ring, preferably a saturated alicyclic ring.

[0115] In the present invention, the C2-C10 aliphatic heterocycle, preferably the C3-C10 aliphatic heterocycle, includes a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle, preferably a saturated aliphatic heterocycle, which can be understood as a ring structure formed by replacing at least one ring carbon atom in the aliphatic ring with a heteroatom (such as N, S, O, etc.).

[0116] In the present invention, the C1-C20 alkyl group, preferably a C1-C16 alkyl group, and further preferably a C1-C10 alkyl group, includes a straight-chain alkyl group or a branched-chain alkyl group, illustratively including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, etc.

[0117] In the present invention, specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned alkyl groups to O.

[0118] In the present invention, a specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned alkyl group, including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0119] In the present invention, the C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0120] In the present invention, specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0121] In the present invention, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, contains at least one C=C, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0122] In the present invention, the "substituted or unsubstituted" group may be substituted with one or more substituents. When there are multiple substituents (at least two), they may be the same or different. The same expressions used above have the same meaning. Unless otherwise specified, the range of substituents is as described in the present invention and will not be further described.

[0123] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered equivalent.

[0124] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms, such as carbon and nitrogen, may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0125] In the compounds described herein, multiple substitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0126] In the present invention, "combination" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by a person skilled in the art from the applicable list. For example, the combination of alkyl and deuterium forms a partially or fully deuterated alkyl group (e.g., deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, etc.); the combination of halogen and alkyl forms a partially or fully halogenated alkyl group (e.g., trifluoromethyl, etc.); or the combination of halogen, alkyl and aryl forms a halogenated arylalkyl group, etc.

[0127] In the compounds mentioned in the present invention, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present invention, adjacent substituents can optionally be connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, alicyclic, aromatic or heteroaromatic rings. In this statement, 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.

[0128] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122M, paragraphs 0132-0161, 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 herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0129] The materials described in the present invention as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the 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.

[0130] 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 equipment conventional 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 is tested for structure confirmation and characteristics using methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to the vapor deposition machine of Nanjing Institute of Microbiology, the optical testing system and life test system of Suzhou Fushida, the ellipsometer of Wuhan Yiguang Technology, etc.), and are tested using methods well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the testing methods, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned relevant contents are no longer expanded and repeated in this invention.

[0131] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0132] Example 1: Synthesis of Compound I-1

[0133]

[0134] (1-1) Synthesis of intermediate S1-1:

[0135] Under nitrogen, raw material M1-1 (96.03 g), raw material M1-2 (120.55 g), trichloroacetic acid (81.70 g), and sodium lauryl sulfate (36.13 g) were added to a dry three-necked reaction flask and stirred at room temperature for 5 h. After the reaction, potassium carbonate (34.55 g) was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain intermediate S1-1 (60.31 g, yield 31.4%). (1-2) Synthesis of intermediate S1-2:

[0136] Under nitrogen, intermediate S1-1 (57.62 g) and pyridine hydrochloride (173.34 g) were added to a dry three-necked reaction flask, and the temperature was raised to 202°C with stirring for 4 h. After the reaction, the temperature was lowered to 50°C, and saturated sodium chloride solution (500 mL) and ethyl acetate (100 mL) were added. The mixture was allowed to stand for separation, and extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain intermediate S1-2 (39.37 g, 73.7% yield).

[0137] (1-3) Synthesis of intermediate S1-3:

[0138] Under nitrogen, to a dry three-necked reaction flask were added intermediate S1-2 (35.61 g), raw material M1-3 (14.80 g), potassium carbonate (55.28 g), and NMP (300 mL). The mixture was heated to 120°C with stirring and reacted for 12 h. After the reaction, the temperature was cooled to room temperature and water (600 mL) was added to precipitate a solid. The solid was filtered, dried, and washed with ethanol to obtain intermediate S1-3 (23.89 g, 51.5% yield).

[0139] (1-4) Synthesis of Compound I-1:

[0140] Under nitrogen, intermediate S1-3 (23.20 g) and tert-butylbenzene (250 mL) were added to a dry three-necked reaction flask. The temperature was lowered to -78°C, and tert-butyllithium pentane solution (62.5 mL, 1.6 M) was slowly added dropwise. The temperature was then slowly raised to 60°C and allowed to react for 3 h. Heating was stopped, and after cooling to -78°C, boron tribromide (12.0 mL) was added and the mixture was allowed to react at room temperature for 6 h. The temperature was then lowered to 0°C, and N,N-diisopropylethylamine (34.9 mL) was added dropwise. The mixture was allowed to react at 120°C for 12 h. After the reaction was completed, the mixture was cooled to room temperature, the fraction was washed with water, dried, concentrated, column chromatographed, and recrystallized to obtain compound I-1 (3.69 g, 16.8% yield).

[0141] MS (m / e) of compound I-1: 438.62; 1 HNMR (400MHz, CDCl3): δ7.58-7.52(m,2H),7.49-7.42(m,2H),7.37-7.20(m,5H),7.02(dd,2H),6.83-6.76(m,2H),6.64(d,2H).

[0142] Example 2: Synthesis of Compound I-33

[0143]

[0144] (2-1) Synthesis of intermediate S2-1:

[0145] The synthetic route of intermediate S2-1 is the same as that of intermediate S1-1. Intermediate S2-1 can be obtained by simply replacing raw material M1-1 with raw material M2-1 and raw material M1-2 with raw material M2-2.

[0146] (2-2) Synthesis of intermediate S2-2:

[0147] Under nitrogen, raw material M2-3 (64.78 g), raw material M2-4 (134.91 g), sodium tert-butoxide (76.88 g), Pd2(dba)3 (7.33 g), tri-tert-butylphosphine (6.47 g), and toluene (600 mL) were added to a dry three-necked reaction flask. The temperature was raised to 105°C with stirring and the reaction was allowed to proceed for 8 h. After the reaction was completed, the temperature was lowered to room temperature, filtered, extracted with dichloromethane, washed with water, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate S2-2 (114.89 g, 68.5% yield).

[0148] (2-3) Synthesis of intermediate S2-3:

[0149] Under nitrogen, to a dry three-necked reaction flask were added intermediate S2-2 (83.86 g), intermediate S2-1 (51.19 g), sodium tert-butoxide (38.44 g), Pd2(dba)3 (3.66 g), tri-tert-butylphosphine (3.24 g), and toluene (400 mL). The mixture was heated to 105°C with stirring and reacted for 8 h. After completion of the reaction, the mixture was cooled to room temperature, filtered, extracted with dichloromethane, washed with water, and the organic phase was purified by column chromatography to obtain intermediate S2-3 (74.53 g, 62.6% yield).

[0150] (2-4) Synthesis of Compound I-33:

[0151] The synthetic route of compound I-33 is the same as that of compound I-1, and compound I-33 can be obtained by simply replacing intermediate S1-3 with intermediate S2-3.

[0152] MS (m / e) of compound I-33: 1164.24; 1 HNMR (400MHz, CDCl3): δ7.93-7.87(m,2H),7.68(dd,2H),7.54-7.47(m,4H),7.39 -7.27(m,12H),7.20(d,2H),7.01-6.93(m,2H),6.88(dd,2H),1.38-1.33(m,63H).

[0153] Example 3: Synthesis of Compound I-79

[0154]

[0155]

[0156] (3-1) Synthesis of intermediate S3-1:

[0157] Under nitrogen, to a dry three-necked reaction flask were added raw material M3-1 (79.04 g), raw material M3-2 (128.53 g), ethanol (500 mL), and acetic acid (45 mL). The mixture was heated to 120°C with stirring for 12 h. After the reaction, the mixture was cooled to room temperature, filtered, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain intermediate S3-1 (98.21 g, 49.3% yield).

[0158] (3-2) Synthesis of intermediate S3-2:

[0159] Under nitrogen, to a dry three-necked reaction flask were added intermediate S3-1 (39.82 g), raw material M3-3 (31.20 g), sodium tert-butoxide (38.44 g), Pd2(dba)3 (3.66 g), tri-tert-butylphosphine (3.24 g), and toluene (400 mL). The mixture was heated to 105°C with stirring and reacted for 8 h. After the reaction, the mixture was cooled to room temperature, filtered, extracted with dichloromethane, washed with water, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate S3-2 (33.36 g, 60.6% yield).

[0160] (3-3) Synthesis of Compound I-79:

[0161] The synthetic route of compound I-79 is the same as that of compound I-1, and compound I-79 can be obtained by simply replacing intermediate S1-1 with intermediate S3-2.

[0162] MS (m / e) of compound I-79: 604.37; 1 HNMR (400MHz, CDCl3): δ7.52-7.45(m,3H),7.41-7.33(m,5H),7.32-7.23(m,3H) ),7.19(dd,1H),7.17-7.05(m,10H),6.99(dd,1H),6.80(dd,1H),6.72(dd,1H).

[0163] Example 4: Synthesis of Compound I-100

[0164]

[0165] (4-1) Synthesis of intermediate S4-2:

[0166] The synthetic route of intermediate S4-2 is the same as that of intermediate S3-2. Only raw material M3-2 is replaced with raw material M4-1 to obtain intermediate S4-2. (4-2) Synthesis of intermediate S4-3:

[0167] Under nitrogen, intermediate S4-2 (56.42 g), tin (94.97 g), HCl solution (125.00 g, 35 wt%), and ethanol (500 mL) were added to a dry three-necked reaction flask. The mixture was heated to 90°C with stirring for 16 h. After the reaction, the mixture was cooled to room temperature and washed with saturated sodium bicarbonate solution until neutral. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate S4-3 (34.73 g, 68.9% yield).

[0168] (4-3) Synthesis of intermediate S4-4:

[0169] The synthetic route of intermediate S4-4 is the same as that of intermediate S3-2. Intermediate S4-4 can be obtained by replacing intermediate S3-1 with intermediate S4-3 and raw material M3-3 with raw material M4-2.

[0170] (4-4) Synthesis of Compound I-100:

[0171] The synthetic route of compound I-100 is the same as that of compound I-33, except that intermediate S2-2 is replaced by intermediate S4-4, and intermediate S2-1 is replaced by raw material M2-3 to obtain compound I-100.

[0172] MS (m / e) of compound I-100: 1014.13; 1 HNMR (400MHz, CDCl3): δ7.52-7.45(m,2H),7.41-7.33(m,6H),7.29-7.23(m,2H),7.17-6.9 2(m,18H),6.88(dd,2H),1.84-1.73(m,4H),1.69-1.57(m,4H),1.36(s,9H),1.30(d,24H).

[0173] Example 5: Synthesis of Compound I-120

[0174]

[0175] (5-1) Synthesis of intermediate S5-1:

[0176] Under nitrogen, to a dry three-necked reaction flask were added intermediate S4-3 (33.28 g), raw material M5-1 (20.53 g), sodium tert-butoxide (11.53 g), Pd2(dba)3 (1.10 g), tri-tert-butylphosphine (0.97 g), and toluene (350 mL). The temperature was raised to 105°C with stirring and the reaction was allowed to proceed for 8 h. After the reaction, the temperature was cooled to room temperature, filtered, extracted with dichloromethane, washed with water, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate S5-1 (26.35 g, 57.3% yield).

[0177] (5-2) Synthesis of intermediate S5-2:

[0178] The synthetic route of intermediate S5-2 is the same as that of intermediate S5-1. Intermediate S5-2 can be obtained by replacing intermediate S4-3 with intermediate S5-1 and raw material M5-1 with raw material M5-2.

[0179] (5-3) Synthesis of Compound I-120:

[0180] The synthetic route of compound I-120 is the same as that of compound I-100, and compound I-120 can be obtained by simply replacing intermediate S4-4 with intermediate S5-2.

[0181] MS (m / e) of compound I-120: 1030.26; 1 HNMR (400MHz, CDCl3): δ7.89-7.78(m,3H),7.64-7.58(m,2H),7.55-7.42(m,5H),7.41-7.23(m,11H) ,7.22-6.98(m,15H),6.88(d,2H),1.84-1.73(m,2H),1.69-1.57(m,2H),1.36(s,9H),1.30(d,12H).

[0182] Example 6: Synthesis of Compound I-134

[0183]

[0184] The synthetic route of compound I-134 is the same as that of compound I-100, except that raw material M4-2 is replaced by raw material M5-2, and raw material M2-3 is replaced by raw material M6-1 to obtain compound I-134.

[0185] MS (m / e) of compound I-134: 1003.51; 1HNMR (400MHz, CDCl3): δ8.18-8.11(m,2H),7.90-7.77(m,6H),7.71-7.61(m,4H),7.55-7.42(m,8H),7.41-7.23(m,14H),7.17-6.98(m,12H).

[0186] Example 7: Synthesis of Compound I-154

[0187]

[0188] (7-1) Synthesis of intermediate S7-1:

[0189] Under nitrogen, raw material M7-1 (87.53 g), raw material M4-1 (136.02 g), boron trifluoride etherate (70.97 g), and chloroform (600 mL) were added to a dry three-necked reaction flask. The temperature was raised to 120°C with stirring and the reaction was allowed to proceed for 7 h. After the reaction, the mixture was cooled to room temperature, filtered, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain intermediate S7-1 (72.52 g, 33.8% yield).

[0190] (7-2) Synthesis of intermediate S7-2:

[0191] Under nitrogen, to a dry three-necked reaction flask were added intermediate S7-1 (64.36 g), raw material M7-2 (31.80 g), sodium tert-butoxide (28.83 g), Pd2(dba)3 (2.75 g), tri-tert-butylphosphine (2.43 g), and toluene (400 mL). The mixture was heated to 105°C with stirring and reacted for 8 h. After completion of the reaction, the mixture was cooled to room temperature, filtered, extracted with dichloromethane, washed with water, and the organic phase was purified by column chromatography to obtain intermediate S7-2 (46.49 g, 55.2% yield).

[0192] (7-3) Synthesis of Compound I-154:

[0193] The synthetic route of compound I-154 is the same as that of compound I-100, except that intermediate S4-2 is replaced by intermediate S7-2, raw material M4-2 is replaced by raw material M3-3, and raw material M2-3 is replaced by raw material M7-3 to obtain compound I-154.

[0194] MS (m / e) of compound I-154: 735.66; 1HNMR (400MHz, CDCl3): δ7.84-7.80(m,1H),7.70-7.65(m,1H),7.58(dd,1H),7.54-7 .44(m,2H),7.40-6.98(m,20H),6.94-6.88(m,2H),6.84-6.78(m,2H),1.34(s,9H).

[0195] Example 8: Synthesis of Compound I-160

[0196]

[0197] The synthetic route of compound I-160 is the same as that of compound I-100, except that raw material M3-3 is replaced by raw material M7-2, and raw material M4-2 is replaced by raw material M8-1 to obtain compound I-160.

[0198] MS (m / e) of compound I-160: 1068.24; 1 HNMR (400MHz, CDCl3): δ7.69(dd,2H),7.52-7.45(m,2H),7.41-7.21(m,14H),7.10(dd,2H),7.08-6.96(m,8H),6.88(dd,2H),1.35(d,27H).

[0199] Example 9: Synthesis of Compound I-173

[0200]

[0201] The synthetic route of compound I-173 is the same as that of compound I-100, except that raw material M3-3 is replaced by raw material M4-2, and raw material M4-2 is replaced by raw material M9-1 to obtain compound I-173.

[0202] MS (m / e) of compound I-173: 1278.93; 1 HNMR (400MHz, CDCl3): δ7.52-7.33(m,16H),7.31-7.23(m,4H),7.15-6.97(m,10H),6 .95-6.84(m,6H),1.84-1.73(m,4H),1.68-1.57(m,4H),1.36(d,27H),1.30(d,24H).

[0203] Example 10: Synthesis of Compound I-181

[0204]

[0205] (10-1) Synthesis of intermediate S10-2:

[0206] The synthetic route of intermediate S10-2 is the same as that of intermediate S5-2. Intermediate S10-2 can be obtained by replacing intermediate S4-3 with intermediate S4-1, raw material M5-1 with raw material M10-1, and raw material M5-2 with raw material M10-2.

[0207] (10-2) Synthesis of Compound I-181:

[0208] The synthetic route of compound I-181 is the same as that of compound I-100, except that intermediate S4-2 is replaced by intermediate S10-2, and raw material M4-2 is replaced by raw material M10-3 to obtain compound I-181.

[0209] MS (m / e) of compound I-181: 1134.26; 1 HNMR (400MHz, CDCl3): δ8.22-8.14(m,1H),7.96-7.89(m,2H),7.63(d,1H),7.52-7.45(m,4H),7.40-7.33(m,2H),7.29-7.24(m,2H),7.19-7. 07(m,5H),7.06-6.98(m,4H),6.95(dd,2H),6.91-6.84(m,4H),6.80(d ,2H),2.26(s,3H),2.13(s,6H),2.08-1.96(m,4H),1.38-1.25(m,33H).

[0210] Example 11: Synthesis of Compound I-232

[0211]

[0212] The synthetic route of compound I-232 is the same as that of compound I-120, except that raw material M5-1 is replaced by raw material M7-2, and raw material M5-2 is replaced by raw material M11-1 to obtain compound I-232.

[0213] MS (m / e) of compound I-232: 1094.31; 1 HNMR (400MHz, CDCl3): δ7.51-7.44(m,3H),7.41-7.23(m,14H),7.20(d,1m),7.17-6.97(m,14H),6.88(dd,2H),1.38-1.32(m,45H).

[0214] The present invention exemplifies the specific synthesis methods of the above compounds. For other compounds for which no specific synthesis methods are given, they can be prepared by similar methods by simply replacing the raw materials. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0215] Device Example 1

[0216] A glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, then mounted on a substrate holder and loaded into a vacuum chamber.

[0217] At a vacuum degree of about 10 -8 Torr's case The deposition rate was 1000 nm by thermal vacuum deposition on the ITO anode. At the same time, the compound HT and HI (weight ratio 97:3) were evaporated as the hole injection layer (HIL) with a thickness of Compound HT was used as the hole transport layer (HTL) with a thickness of Compound EB is used as electron blocking layer (EBL) with a thickness of Then, the compound BH as the main blue light emitting material and the compound I-1 (weight ratio 98:2) were co-evaporated to form the light emitting layer (EML) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated (weight ratio 50:50) as an electron transport layer (ETL) with a thickness of Finally, evaporation Thickness of 8-hydroxyquinoline-lithium (Liq) as the electron injection layer (EIL), and evaporated The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

[0218] Device Examples 2 to 11, Device Comparative Example 1

[0219] The only difference between it and device embodiment 1 is that the doping materials of the light-emitting layer are the compounds shown in Table 1; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0220] The molecular structure formula of the relevant materials is shown below:

[0221]

[0222]

[0223] Table 1 lists the current density of 10mA / cm 2 Under these conditions, the voltage (V), external quantum efficiency (EQE), and lifetime (h) were measured. To better illustrate the data comparison, the voltage, external quantum efficiency, and lifetime of Comparative Example 1 were set to 100%, and the voltage, external quantum efficiency, and lifetime data of Device Examples 1 to 11 were converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0224] Table 1

[0225] Device Doping materials Voltage (relative value) EQE (relative value) Lifespan (relative value) Device Example 1 I-1 95％ 114％ 117％ Device Example 2 I-33 93％ 119％ 120％ Device Example 3 I-79 93％ 117％ 119％ Device Example 4 I-100 92％ 123％ 132％ Device Example 5 I-120 91％ 126％ 135％ Device Example 6 I-134 92％ 124％ 130％ Device Example 7 I-154 93％ 121％ 124％ Device Example 8 I-160 91％ 124％ 133％ Device Example 9 I-173 92％ 126％ 134％ Device Example 10 I-181 92％ 125％ 131％ Device Example 11 I-232 91％ 126％ 136％ Device Comparative Example 1 Ref-1 100％ 100％ 100％

[0226] As shown in Table 1, at 10 mA / cm 2 At the same current density, compared to Comparative Example 1, device Examples 1-11 achieved voltage reductions of 5% to 9%, external quantum efficiencies of 14% to 26%, and extended device lifetimes by up to 36%. These data demonstrate that devices prepared using the organic boron-containing compounds provided by the present invention exhibit lower voltages, higher external quantum efficiencies, and longer lifetimes.

[0227] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments of the present invention. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. An organic boron-containing compound having a structure as shown in formula (I): In formula (I), M is selected from C, Si, Ge or Sn; X1 and X2 are each independently selected from O, S, Se, NR X1 , CR X2 R X3 or SiR X4 R X5 ; Y1 and Y2 are each independently selected from O, S, Se, NR Y1 , CR Y2 R Y3 or SiR Y4 R Y5 ; R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 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; the R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; A1, A2, A3, A4, A5, A6 are each independently selected from N or CR A ; U1, U2, U3 are each independently selected from N or CR U ; Z1, Z2, Z3, Z4, Z5, and Z6 are each independently selected from N or CR Z ; R A 、R U 、R Z Each is 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, substituted or unsubstituted C3-C30 heteroaryl; the adjacent R A They are not connected or connected to form a ring through chemical bonds; the adjacent R U They are not connected or connected to form a ring through chemical bonds; the adjacent R Z They are not connected or connected to form a ring through chemical bonds; R A 、R U 、R Z 、R X1 、R X2 、R X3 、R X4 、R X5 、R Y1 、R Y2 、R Y3 、R Y4 、R Y5 The substituents substituted in the above-mentioned group are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxyl, ester, 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, or a combination of at least two thereof.

2. The organic boron-containing compound according to claim 1, characterized in that X1 and X2 are each independently selected from O, S or NR X1 , R X1 The definition of is the same as that in formula (I), Preferably, the organic boron-containing compound has a structure as shown in any one of formula (II-1) to formula (II-6): In formula (II-1) to formula (II-6), A1, A2, A3, A4, A5, A6, U1, U2, U3, M, Y1, Y2, Z1, Z2, Z3, Z4, Z5, Z6 and R X1 The definitions of are the same as those in formula (I).

3. The organic boron-containing compound according to claim 1 or 2, characterized in that Z1, Z2, Z3, Z4, Z5, and Z6 are each independently selected from CR Z ; Preferably, R Z Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; preferably selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

4. The organic boron-containing compound according to any one of claims 1 to 3, characterized in that Y1 and Y2 are each independently selected from O, S, NR Y1 or CR Y2 R Y3 , R Y1 、R Y2 、R Y3 The definition of is the same as that in formula (I); Preferably, R Y1 Each is independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; preferably selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, benzofluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl; Optionally, the R Y1 The substituents substituted in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, R Y2 、R Y3 Each is independently selected from any one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, preferably selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, phenyl, biphenyl, naphthyl, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothienyl, and dibenzothienyl; Optionally, the R Y2 、R Y3 The substituents substituted in the alkyl group are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

5. The organic boron-containing compound according to any one of claims 1 to 4, characterized in that M is selected from C or Si; and / or, at most one of A1, A2, A3 is selected from N; and / or at most one of A4, A5, A6 is selected from N; preferably, A1, A2, A3, A4, A5, A6 are each independently selected from CR A ; Preferably, R A Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; preferably selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

6. The organic boron-containing compound according to any one of claims 1 to 5, characterized in that R X1 Each is independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; preferably selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, pyridylphenyl, pyridyl, phenylpyridyl, bipyridyl, benzoheteroanthryl, benzothioxanthenyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl, N-phenylcarbazolyl; Optionally, the R X1 The substituents substituted in the alkyl group are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

7. The organic boron-containing compound according to any one of claims 1 to 6, characterized in that At most one of U1, U2, and U3 is selected from N. Preferably, U1, U2, and U3 are each independently selected from CR U ; Preferably, R U Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted 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, it is selected from hydrogen, deuterium, halogen, cyano, or any of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, tetrahydropyrrolyl, tetrahydropyranyl, phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, Wherein, Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, pyridyl, dibenzofuranyl, and dibenzothiophenyl; the adjacent R U They are not connected or connected to form a ring through chemical bonds; Optionally, the R U The substituents substituted in the alkyl group are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl.

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

9. Use of the organic boron-containing compound according to any one of claims 1 to 8 in the preparation of an organic electroluminescent device; Preferably, the organic boron-containing compound is used as a doping material for a light-emitting layer in an organic electroluminescent device. 10 . An organic electroluminescent device comprising a light-emitting layer, wherein a doping material of the light-emitting layer comprises the organic boron-containing compound according to claim 1 .

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