Organic compound, application thereof and organic electroluminescent device

Abstract

The invention relates to an organic compound with a structure as shown in the following formula, belongs to the technical field of organic light-emitting materials, and also relates to application of the compound in an organic light-emitting device. When the compound is used as a luminescent material in an OLED device, the compound shows excellent device performance and stability, and a green light OLED device with high efficiency, low roll-off and high color purity can be realized. The invention also protects the organic light-emitting device adopting the compound with the general formula.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and particularly to a novel heterogeneous boron-nitrogen organic compound and its applications, as well as an organic electroluminescent device containing the compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine within the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and its application is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials has become increasingly focused. This is because a high-efficiency, long-lifespan OLED device is typically the result of optimized device structure and the combination of various organic materials. To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve OLED device performance, it is necessary not only to innovate OLED device structures and manufacturing processes, but also to continuously research and innovate the optoelectronic functional materials within OLED devices to prepare functional materials with higher performance. Based on this, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and superior lifespans.

[0004] TADF materials can theoretically achieve 100% internal quantum efficiency through the upconversion process from triplet to singlet states, thus enabling highly efficient luminescence. Traditional TADF molecules have a highly twisted electron donor-acceptor structure, which cannot simultaneously accommodate high reverse intersystem crossing rates and high radiative transition rates, limiting further efficiency improvements. Furthermore, because TADF materials emit light in the CT state, their broad spectrum cannot meet the color requirements of BT.2020, thus restricting their further application in the display field. Boron-nitrogen-based multiple resonance MR-TADF materials, however, possess advantages such as high color purity and high luminous efficiency, attracting widespread attention from the scientific and industrial communities. However, because the peripheral substituents have little effect on the S1 level, it is difficult to control the material's emission color, limiting it to the blue-deep blue region. Moreover, the significant overlap between its HOMO and LUMO levels restricts ΔE... ST The relatively large size and slow reverse intersystem crossing rate greatly limit the further application of MR-TADF materials in high-resolution displays, full-color displays, and white light illumination. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides a general formula compound, specifically a heterogeneous boron-nitrogen organic compound, the structure of which is shown in general formula (Ⅰ):

[0006]

[0007] In formula (Ⅰ), ring A1, ring A2 and ring A3 are each independently selected from any one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings;

[0008] The substituents in rings A1, A2, and A3 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, and R. 1 Substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, R 1 Substituted or unsubstituted C3-C20 cycloalkyl groups, R 1 Substituted or unsubstituted C1–C20 alkoxy groups, R 1 Substituted or unsubstituted C1-C20 alkylsilyl groups, R 1 Substituted or unsubstituted C1-C20 alkylamino groups, R 1 Substituted or unsubstituted C6–C30 arylamino groups, R 1 Substituted or unsubstituted C3–C30 heteroarylamino groups, R 1 Substituted or unsubstituted C6–C30 aryloxy groups, R 1 Substituted or unsubstituted C3–C30 heteroaryloxy groups, R 1 Substituted or unsubstituted C6-C60 aryl, R1 One of the C3-C60 heteroaryl groups, substituted or unsubstituted;

[0009] Furthermore, the substituents in rings A1, A2, and A3 are not connected to each other independently, or two adjacent substituents are connected to each other by chemical bonds to form a ring; the substituents in rings A1, A2, and A3 are not connected to the adjacent ring structure independently, or are connected to the adjacent ring structure by chemical bonds to form a ring.

[0010] The dashed line between rings A1 and A2 represents a disconnect or a single-key connection;

[0011] The R 1 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl.

[0012] R a R b R c R d R e Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, R 2 Substituted or unsubstituted C1-C10 chain alkyl groups, R 2 Substituted or unsubstituted C3-C10 cycloalkyl groups, R 2 Substituted or unsubstituted C1-C10 alkoxy groups, R 2 Substituted or unsubstituted C1-C10 alkylsilyl groups, R 2 Substituted or unsubstituted C1-C10 alkylamino groups, R 2 Substituted or unsubstituted C6–C30 arylamino groups, R 2 Substituted or unsubstituted C3–C30 heteroarylamino groups, R 2 Substituted or unsubstituted C6–C30 aryloxy groups, R 2 Substituted or unsubstituted C3–C30 heteroaryloxy groups, R 2 Substituted or unsubstituted C6-C60 aryl, R 2 One of the substituted or unsubstituted C3-C60 heteroaryl groups; and R a R b R c It can be hydrogen at one time or deuterium at another time;

[0013] The R a R bR c Each is independent and not connected to the adjacent ring structure;

[0014] The R 2 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl.

[0015] It should be noted that while the possible effects of each group / feature have been described separately in this application for ease of explanation, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups and structures, rather than the effect of a single group or structure.

[0016] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0017] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0018] In this specification, the ring structure indicated by "—" represents any position on the ring structure where bonding can occur; the dashed double bond represents the position where the group is fused in the parent nucleus.

[0019] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0020] In this invention, the description of chemical elements, unless otherwise specified, usually includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes the concept of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be elaborated further.

[0021] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0022] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0023] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring groups.

[0024] In this invention, the term "single bond connection or fused connection" generally refers to the substituent group being directly connected to the parent structure via a single bond, or the substituent group being fused to the parent structure, thereby forming a fused-ring aromatic hydrocarbon structure with multiple aromatic rings sharing the same edge. The aromatic rings here include six-membered aromatic rings such as benzene rings, as well as five-membered and six-membered heteroaromatic rings containing atoms such as N, O, or S.

[0025] In this invention, C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0026] C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0027] 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.

[0028] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0029] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0030] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0031] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0032] In this invention, the substituted or unsubstituted C6-C60 aryl (or C6-C50 aryl) includes monocyclic aryl and fused-ring aryl, preferably C6-C30 aryl, and more preferably C6-C20 aryl. A monocyclic aryl refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0033] The C3-C60 heteroaryl (or C6-C50 heteroaryl) mentioned in this invention includes monocyclic heteroaryl and fused-ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and even more preferably C5-C12 heteroaryl. A monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0034] The aryloxy or heteroaryloxy groups in this invention can be exemplified by the monovalent groups formed by the above-mentioned aryl or heteroaryl groups and oxygen.

[0035] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0036] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0037] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0038] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferred, substituted or unsubstituted C1-C16 chain alkyl groups are more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0039] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0040] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and more preferably methoxy.

[0041] In this specification, the substituted or unsubstituted C1-C20 silane and the substituted or unsubstituted C1-C10 silane are examples of silanes substituted with groups listed in the above-mentioned C1-C10 chain alkyl groups, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0042] In this specification, the C2-C20 alkenyl group, preferably C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0043] Furthermore, the compounds of the present invention have a structure as shown in general formula (1):

[0044]

[0045] Ring A1, Ring A2, Ring A3, R a R b R c R d R e The scope of the definition is the same as that in equation (Ⅰ);

[0046] Preferably, ring A1, ring A2 and ring A3 are one of substituted or unsubstituted C6-C30 aromatic rings or substituted or unsubstituted C6-C30 heteroaromatic rings;

[0047] More preferably, at least one of ring A1 and ring A2 is a substituted or unsubstituted C6-C30 six-membered aromatic ring or a substituted or unsubstituted C6-C30 six-membered heteroaromatic ring;

[0048] More preferably, ring A1 and ring A2 are each independently selected from one of substituted or unsubstituted benzene, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted benzoselenene, and substituted or unsubstituted N-phenylcarbazole; ring A3 is one of substituted or unsubstituted benzene ring and substituted or unsubstituted naphthyl ring; each of the substituted substituents is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0049] Furthermore, in the above-mentioned general formula compound, ring A3 is any structure shown in formula (a), (b), (c), (d), (e), (f), or (g), and rings A1 and A2 are each independently any structure shown in formula (a), (b), (c), (d), (e), or (f), wherein any of the dashed double bonds (c1), (c2), (c3), (c4), (c5), (c6), (c7), (c8), (d1), (d2), (d3), (d4), (d5), (d6) represents the fusion position of the group:

[0050]

[0051] Among them, U 1 U 2 U 3 U 4 U 5 U 6 U 7 U 8 U 9 U 10 U 11 U 12 U 13 U 14 U 15 U 16 U 17 U 18 U 19 U 20 U 21 U 22 U 23 U 24 Each is independently selected from C, CH, or N;

[0052] The U 1 U 2 U 3 U 4 In the middle, two adjacent pairs are either not connected or connected in a loop, U 5 U 6 U 7 U 8 In the middle, two adjacent pairs are either not connected or connected in a loop, U 9 U 10 Between, U 11 U 12 U 13 U 14 U 15 U 16 U 17 U 18In the middle, two adjacent pairs are either not connected or connected in a loop, U 19 U 20 U 21 U 22 U 23 U 24 Two adjacent elements in the middle are either not connected or connected in a loop;

[0053] Z 1 Z 2 Each is independently selected from O, S, Se, NR 21 or CR 22 R 23 ;

[0054] R 21 R 22 R 23 Each of the following is independently selected from one of the following: unsubstituted or R'-substituted C1-C36 chain alkyl, unsubstituted or R'-substituted C3-C36 cycloalkyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C6-C60 aryloxy, and unsubstituted or R'-substituted C5-C60 heteroaryl;

[0055] The R 22 With R 23 They are either not connected or connected in a loop;

[0056] When Z 1 Selected from NR 21 At that time, the R 21 with U 5 The R is either not connected or connected in a loop. 21 with U 9 Disconnected or connected in a loop; when Z 2 Selected from NR 21 At that time, the R 21 with U 7 Do not connect or connect in a loop;

[0057] R' is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 arylboryl, and C3-C30 heteroaryl.

[0058] Preferably, ring A3 is a structure shown in any of formula (a), formula (f), or formula (g); ring A1 and ring A2 are each independently a structure shown in any of formula (a), formula (b), formula (c), formula (d), or formula (f), and at least one of ring A1 and ring A2 is a structure shown in any of formula (b), formula (c), or formula (d).

[0059] Furthermore, the formula (g) in the above-mentioned general formula compound has the structure shown in the following formula (g1):

[0060]

[0061] Preferably, U 20 U 21 U 22 U 23 U 24 Each is independently selected from C or CH.

[0062] Furthermore, in the above-mentioned general formula compounds, in formulas (b), (c), and (d), Z 1 Z 2 Each is independently selected from O, S, and NR. 21 ;

[0063] R 21Selected from one of the following groups, either unsubstituted or R'-substituted: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimenyl, isotrimeric indo[a], spirotrimeric indo[a], spiroisotrimeric indo[a], furanyl, benzo[a]furanyl, isobenzo[a]furanyl, di[a] ... Benzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indoxarcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthiazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxalinimidazoleyl, oxazolyl, benzooxazolyl Naphtho-oxazolyl, anthraquinonexazolyl, phenanthrenexazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanthyl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazyl Azolyl, benzocarbamoyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl

[0064] 1,2,3,4-Tetraazinyl, 1,2,3,5-Tetraazinyl;

[0065] R' is selected from one of deuterium, cyano, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0066] Furthermore, in the above-mentioned general formula compound, the U 1 U 2 U 3 U 4 U 5 U 6 U 7 U 8 U 9 U 10 U11 U 12 U 13 U 14 U 15 U 16 U 17 U 18 U 19 U 20 U 21 U 22 U 23 U 24 Each is independently selected from C or CH.

[0067] Furthermore, the compounds of the present invention have a structure as shown in any of formulas (2) to (13):

[0068]

[0069] In general formulas (2) to (15), R a R b R c R d R e The definition is the same as that in equation (Ⅰ); Z 1 U 1 U 2 U 3 U 4 U 5 U 6 U 7 U 8 The definitions of and are the same as those in equations (a) and (b).

[0070] Furthermore, in the above-mentioned general formula compounds, R a R b R c R d R eThe following groups, independently selected from hydrogen, deuterium, deuterated, or undeuterated groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl Methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indofluorenyl, trimerinyl, isotrimerinyl, spirotriinyl, spiroisotriinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuran Thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, benzoselenophene, isobenzoselenophene, dibenzoselenophene, pyrrole, isoindolyl, carbazole, tert-butyl-substituted carbazole, indole-carbazole, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7, 8-Quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniummidazoleyl, pyraziniummidazoleyl, quinoxaliniummidazoleyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinonexazolyl, phenanthrenexoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, Benzopyrimidinyl, quinoxalinyl, 1,5-diazaphenanthyl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolinyl, phenanthrolinel, 1, 2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridylyl, indazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, (poly)halobenzene, (poly)cyanobenzene or (poly)trifluoromethylbenzene, diphenylamino, tert-butyl-substituted diphenylamino, triphenylamino;

[0071] Preferably, R a R b R c R e The following groups are independently selected from hydrogen, deuterium, deuterated, or undeuterated groups: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl; and R a R b R c It can be hydrogen at one time or deuterium at another time;

[0072] R d The following groups are selected from hydrogen, deuterium, deuterated or undeuterated: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl or trifluoromethyl.

[0073] Furthermore, in the above-mentioned general formula compounds, R 1 R 2 R' is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, biphenyl, terphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzo[a]furanyl, isophenyl benzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indoxocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthrozimidazoleyl, pyridinzimidazoleyl, pyrazinzimidazoleyl, quinoxalinzimidazoleyl, oxazolyl, 1, One or a combination of two of the following: 2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene, (poly)trifluoromethylbenzene.

[0074] Furthermore, the general formula compounds of the present invention can preferably include the following specific structural compounds, which are merely representative examples:

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0112] This invention also protects the application of any of the compounds shown in general formula (Ⅰ) and formulas (1) to (15) as functional materials in organic electronic devices, which include: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

[0113] The present invention also provides an organic electroluminescent device, comprising a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any of the above general formulas (1) to (15).

[0114] Specifically, an embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains a compound of the present invention represented by any one of the above general formulas (1) to (13).

[0115] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, high color purity, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials.

[0116] The specific reasons for the excellent performance of the compounds of the present invention when used in organic electroluminescent devices are not yet clear. The following are the inventors' speculations, but these speculations do not limit the scope of protection of the present invention:

[0117] (1) The general formula compound of the present invention fuses indolecarbazole on the benzene ring on the side of the parent core of the BN-type multiple resonance material. While expanding the conjugated plane to achieve red shift of light color, it maintains the rigid structure of the molecule and has a large oscillator strength, which is beneficial to improving the luminescence efficiency.

[0118] (2) The general formula compound of the present invention has a high molecular level orientation, which is beneficial to improving the light extraction efficiency of OLED devices, thereby improving the luminous efficiency of the devices.

[0119] (3) The polyalkyl-substituted phenyl groups attached to the N atom of the parent nucleus in the general formula compound of the present invention have large steric hindrance, which can suppress problems such as concentration quenching, exciton annihilation and spectral broadening caused by molecular stacking, thereby improving the performance of the device.

[0120] (4) The general formula compound of the present invention has a narrow half-width of the spectrum and high color purity, which can effectively improve the color gamut of the device, and thus is expected to further meet the demand for ultra-high-definition display.

[0121] The preparation process of the compounds of this invention is simple and easy, and the raw materials are readily available, making them suitable for mass production scale-up. When used as luminescent materials in OLED devices, the compounds of this invention exhibit excellent device performance and stability, enabling the realization of high-efficiency, low-roll-off, and high-color-purity green OLED devices. Detailed Implementation

[0122] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0123] The various chemical reagents used in this invention, such as petroleum ether, ethyl acetate, anhydrous sodium sulfate, toluene, dichloromethane, o-dichlorobenzene, potassium carbonate, 9H-carbazole, cesium carbonate, and reaction intermediates, were all purchased from Shanghai Titan Technology Co., Ltd., Shanghai Bid Pharmaceutical Technology Co., Ltd., and Anhui Zesheng Technology Co., Ltd. The molecular formulas of the following compounds were determined using a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0124] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0125] Synthesis Example:

[0126] Representative synthetic pathways:

[0127] (1) Synthesis of precursors:

[0128] The synthetic route of this invention is implemented starting from the following three types of precursors:

[0129]

[0130] The synthesis of precursor 1 and precursor 3 is obtained through two pathways: when R d When the substitution site is a carbon atom, it is prepared by the Suzuki-Miyaura CC coupling reaction; when R d When the substitution site is a nitrogen atom, it is prepared by the Buchwald-Hartwig CN coupling reaction.

[0131] The synthetic pathway for precursor 2 is as follows:

[0132]

[0133] In a 100 mL dry double-necked round-bottom flask, 3 mmol of 2-bromoindole[3,2,1-jk]carbazole derivative, 3 mmol of aniline with R substitution at positions 1,3,5, 0.09 mmol of Pd2(dba)3, 0.18 mmol of tri-tert-butylphosphine tetrafluoroborate, 9 mmol of sodium tert-butoxide, and 100 mL of toluene were added. The mixture was heated to 120 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to give precursor compound 2 as a yellow solid.

[0134] (2) Synthesis of intermediates:

[0135] When ring A1 and ring A2 are not connected to form a ring, intermediate body 1 is obtained; when ring A1 and ring A2 are connected to form a ring, intermediate body 2 is obtained.

[0136]

[0137] The synthesis path of intermediate 1 is as follows:

[0138]

[0139] In a 100 mL dry double-necked round-bottom flask, precursor 1 (3 mmol), precursor 2 (3 mmol), diarylamine (3 mmol), Pd2(dba)3 (0.09 mmol), tri-tert-butylphosphine tetrafluoroborate (0.18 mmol), sodium tert-butoxide (9 mmol), and xylene (100 mL) were added. The mixture was heated to 140 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, it was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to give intermediate compound 1 as a yellow solid.

[0140] The synthesis path of intermediate 2 is as follows:

[0141]

[0142] In a 100 mL dry double-necked round-bottom flask, precursor 3 (3 mmol), carbazole derivative (3 mmol), Cs₂CO₃ (3.3 mmol), and DMF (100 mL) were added. The mixture was heated to 150 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, it was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to give precursor compound 3-1 as a white solid.

[0143] Next, in a 100 mL dry double-necked round-bottom flask, precursor 3-1 (3 mmol), precursor 2 (3 mmol), Pd2(dba)3 (0.09 mmol), tri-tert-butylphosphine tetrafluoroborate (0.18 mmol), sodium tert-butoxide (9 mmol), and xylene (100 mL) were added. The mixture was heated to 140 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, it was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to give intermediate compound 2 as a yellow solid.

[0144] (3) The synthetic route of the final product is as follows:

[0145]

[0146] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0147] Synthesis Example 1: Synthesis of Compound G1

[0148]

[0149] Under nitrogen protection, a pentane solution of tert-butyllithium (10.56 mL, 1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 1-1 (2.57 g, 3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (1.88 g, 7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (1.94 g, 15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G1 (0.57 g, 22.8% yield, HPLC purity 99.35%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 830.36; Elemental analysis results: Theoretical values: C, 86.74; H, 5.22; B, 1.30; N, 6.74; Experimental values: C, 86.75; H, 5.21; B, 1.32; N, 6.72.

[0150] Synthesis Example 2: Synthesis of Compound G3

[0151]

[0152] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 3-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G3 (25% yield, HPLC purity 99.40%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 735.38; Elemental analysis results: Theoretical values: C, 86.52; H, 6.30; B, 1.47; N, 5.71; Experimental values: C, 86.51; H, 6.31; B, 1.48; N, 5.70.

[0153] Synthesis Example 3: Synthesis of Compound G21

[0154]

[0155] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 21-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G21 (25% yield, HPLC purity 99.40%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 802.33; Elemental analysis results: Theoretical values: C, 86.78; H, 4.90; B, 1.35; N, 6.97, Experimental values: C, 86.79; H, 4.91; B, 1.34; N, 6.96.

[0156] Synthesis Example 4: Synthesis of Compound G40

[0157]

[0158] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 40-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G40 (28% yield, HPLC purity 99.50%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 769.33; Elemental analysis results: Theoretical values: C, 85.82; H, 5.24; B, 1.40; N, 5.46; O, 2.08; Experimental values: C, 85.81; H, 5.25; B, 1.41; N, 5.43; O, 2.10.

[0159] Synthesis Example 5: Synthesis of Compound G60

[0160]

[0161] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 60-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G60 (28% yield, HPLC purity 99.32%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 917.40; Elemental analysis results: Theoretical values: C, 85.04; H, 5.71; B, 1.18; N, 4.58; S, 3.49; Experimental values: C, 85.05; H, 5.70; B, 1.17; N, 4.57; S, 3.51.

[0162] Synthesis Example 6: Synthesis of Compound G71

[0163]

[0164] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 71-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G71 (29% yield, HPLC purity 99.35%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 955.38; Elemental analysis results: Theoretical values: C, 86.69; H, 4.85; B, 1.13; N, 7.33, Experimental values: C, 86.70; H, 4.86; B, 1.12; N, 7.32.

[0165] Synthesis Example 7: Synthesis of Compound G98

[0166]

[0167] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 98-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G98 (31% yield, HPLC purity 99.42%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 788.31; Elemental analysis results: Theoretical values: C, 86.80; H, 4.73; B, 1.37; N, 7.10, Experimental values: C, 86.82; H, 4.72; B, 1.35; N, 7.11.

[0168] Synthesis Example 8: Synthesis of Compound G126

[0169]

[0170] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 126-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G126 (28% yield, HPLC purity 99.30%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1054.37; Elemental analysis results: Theoretical values: C, 80.91; H, 5.26; B, 1.03; N, 5.31; Se, 7.49; Experimental values: C, 80.90; H, 5.25; B, 1.02; N, 5.33; Se, 7.50.

[0171] Synthesis Example 9: Synthesis of Compound G154

[0172]

[0173] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 154-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G154 (26% yield, HPLC purity 99.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 814.29; Elemental analysis results: Theoretical values: C, 85.50; H, 4.33; B, 1.33; N, 6.88; O, 1.96; Experimental values: C, 85.50; H, 4.32; B, 1.32; N, 6.89; O, 1.97.

[0174] Synthesis Example 10: Synthesis of Compound G172

[0175]

[0176] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 172-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G72 (25% yield, HPLC purity 99.33%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 830.27; Elemental analysis results: Theoretical values: C, 83.85; H, 4.25; B, 1.30; N, 6.74; S, 3.86; Experimental values: C, 83.83; H, 4.26; B, 1.31; N, 6.75; S, 3.85.

[0177] Synthesis Example 11: Synthesis of Compound G183

[0178]

[0179] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 183-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G183 (27% yield, HPLC purity 99.43%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 932.33; Elemental analysis results: Theoretical values: C, 82.40; H, 4.32; B, 1.16; F, 6.11; N, 6.01; Experimental values: C, 82.40; H, 4.30; B, 1.18; F, 6.10; N, 6.02.

[0180] Synthesis Example 12: Synthesis of Compound G200

[0181]

[0182] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 200-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G200 (23% yield, HPLC purity 99.23%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 857.28; Elemental analysis results: Theoretical values: C, 81.22; H, 4.11; B, 1.26; F, 6.64; N, 4.90; O, 1.87; Experimental values: C, 81.20; H, 4.10; B, 1.27; F, 6.65; N, 4.91; O, 1.87.

[0183] Synthesis Example 13: Synthesis of Compound G223

[0184]

[0185] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 223-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G223 (22% yield, HPLC purity 99.24%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 921.20; Elemental analysis results: Theoretical values: C, 75.66; H, 3.84; B, 1.17; F, 6.19; N, 4.56; Se, 8.58; Experimental values: C, 75.65; H, 3.85; B, 1.18; F, 6.20; N, 4.55; Se, 8.57.

[0186] Synthesis Example 14: Synthesis of Compound G245

[0187]

[0188] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 245-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G245 (25% yield, HPLC purity 99.44%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 954.35; Elemental analysis results: Theoretical values: C, 86.79; H, 4.54; B, 1.12; N, 5.87; O, 1.68; Experimental values: C, 86.80; H, 4.55; B, 1.14; N, 5.85; O, 1.66.

[0189] Synthesis Example 15: Synthesis of Compound G257

[0190]

[0191] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 257-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G257 (23% yield, HPLC purity 99.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1012.38; Elemental analysis results: Theoretical values: C, 85.36; H, 4.88; B, 1.07; N, 5.53; S, 3.16; Experimental values: C, 85.37; H, 4.89; B, 1.06; N, 5.54; S, 3.14.

[0192] Synthesis Example 16: Synthesis of Compound G274

[0193]

[0194] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 274-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G274 (26% yield, HPLC purity 99.38%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 853.34; Elemental analysis results: Theoretical values: C, 85.81; H, 4.72; B, 1.27; N, 8.20; Experimental values: C, 85.82; H, 4.73; B, 1.26; N, 8.19.

[0195] Synthesis Example 17: Synthesis of Compound G295

[0196]

[0197] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 295-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G295 (25% yield, HPLC purity 99.28%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1019.39; Elemental analysis results: Theoretical values: C, 84.78; H, 4.55; B, 1.06; N, 9.61, Experimental values: C, 84.78; H, 4.54; B, 1.05; N, 9.63.

[0198] Synthesis Example 18: Synthesis of Compound G307

[0199]

[0200] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 307-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G307 (25% yield, HPLC purity 99.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 964.47; Elemental analysis results: Theoretical values: C, 87.12; H, 5.95; B, 1.12; N, 5.81, Experimental values: C, 87.10; H, 5.94; B, 1.14; N, 5.82.

[0201] Synthesis Example 19: Synthesis of Compound G318

[0202]

[0203] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 318-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G318 (27% yield, HPLC purity 99.33%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1006.27; Elemental analysis results: Theoretical values: C, 81.20; H, 4.31; B, 1.07; N, 5.57; Se, 7.85; Experimental values: C, 81.20; H, 4.32; B, 1.06; N, 5.59; Se, 7.83.

[0204] Synthesis Example 20: Synthesis of Compound G325

[0205]

[0206] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 325-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G325 (23% yield, HPLC purity 99.25%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 872.41; Elemental analysis results: Theoretical values: C, 86.68; H, 5.66; B, 1.24; N, 6.42; Experimental values: C, 86.69; H, 5.66; B, 1.24; N, 6.41.

[0207] Synthesis Example 21: Synthesis of Compound G338

[0208]

[0209] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 338-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G338 (22% yield, HPLC purity 99.28%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 721.36; Elemental analysis results: Theoretical values: C, 86.54; H, 6.15; B, 1.50; N, 5.81, Experimental values: C, 86.55; H, 6.15; B, 1.50; N, 5.80.

[0210] Synthesis Example 22: Synthesis of Compound G361

[0211]

[0212] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 361-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G361 (22% yield, HPLC purity 99.28%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 853.42; Elemental analysis results: Theoretical values: C, 85.80; H, 6.14; B, 1.27; N, 4.92; O, 1.87; Experimental values: C, 85.80; H, 6.16; B, 1.26; N, 4.90; O, 1.88.

[0213] Synthesis Example 23: Synthesis of Compound G387

[0214]

[0215] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 387-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G387 (27% yield, HPLC purity 99.48%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 986.55; Elemental analysis results: Theoretical values: C, 86.39; H, 6.84; B, 1.09; N, 5.68; Experimental values: C, 86.38; H, 6.85; B, 1.10; N, 5.67.

[0216] Synthesis Example 24: Synthesis of Compound G403

[0217]

[0218] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 403-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G403 (29% yield, HPLC purity 99.51%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1098.67; Elemental analysis results: Theoretical values: C, 86.31; H, 7.61; B, 0.98; N, 5.10; Experimental values: C, 86.30; H, 7.60; B, 0.99; N, 5.11.

[0219] Synthesis Example 25: Synthesis of Compound G435

[0220]

[0221] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 435-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G435 (28% yield, HPLC purity 99.50%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1098.67; Elemental analysis results: Theoretical values: C, 86.47; H, 7.44; B, 0.99; N, 5.10, Experimental values: C, 86.48; H, 7.45; B, 0.98; N, 5.09.

[0222] Synthesis Example 26: Synthesis of Compound G456

[0223]

[0224] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 456-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G456 (28% yield, HPLC purity 99.50%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 898.38; Elemental analysis results: Theoretical values: C, 85.52; H, 5.27; B, 1.20; N, 6.23; O, 1.78; Experimental values: C, 85.50; H, 5.27; B, 1.20; N, 6.24; O, 1.79.

[0225] Synthesis Example 27: Synthesis of Compound G459

[0226]

[0227] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 459-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G459 (27% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 914.36; Elemental analysis results: Theoretical values: C, 84.02; H, 5.18; B, 1.18; N, 6.12; S, 3.50; Experimental values: C, 84.00; H, 5.17; B, 1.18; N, 6.13; S, 3.52.

[0228] Synthesis Example 28: Synthesis of Compound G475

[0229]

[0230] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 475-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G475 (29% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 914.36; Elemental analysis results: Theoretical values: C, 84.02; H, 5.18; B, 1.18; N, 6.12; S, 3.50; Experimental values: C, 84.01; H, 5.17; B, 1.18; N, 6.13; S, 3.51.

[0231] Synthesis Example 29: Synthesis of Compound G484

[0232]

[0233] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 484-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G484 (29% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 973.43; Elemental analysis results: Theoretical values: C, 86.32; H, 5.38; B, 1.11; N, 7.19; Experimental values: C, 86.31; H, 5.38; B, 1.10; N, 7.21.

[0234] Synthesis Example 30: Synthesis of Compound G491

[0235]

[0236] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 491-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G491 (25% yield, HPLC purity 99.36%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 914.36; Elemental analysis results: Theoretical values: C, 84.02; H, 5.18; B, 1.18; N, 6.12; S, 3.50; Experimental values: C, 84.00; H, 5.18; B, 1.18; N, 6.13; S, 3.51.

[0237] Synthesis Example 31: Synthesis of Compound G517

[0238]

[0239] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 517-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G517 (26% yield, HPLC purity 99.35%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1016.42; Elemental analysis results: Theoretical values: C, 82.67; H, 5.15; B, 1.06; F, 5.60; N, 5.52; Experimental values: C, 82.67; H, 5.14; B, 1.06; F, 5.62; N, 5.51.

[0240] Synthesis Example 32: Synthesis of Compound G547

[0241]

[0242] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 547-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G547 (28% yield, HPLC purity 99.55%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1060.56; Elemental analysis results: Theoretical values: C, 87.15; H, 6.55; B, 1.02; N, 5.28; Experimental values: C, 87.16; H, 6.56; B, 1.01; N, 5.27.

[0243] Synthesis Example 33: Synthesis of Compound G554

[0244]

[0245] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 554-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G554 (24% yield, HPLC purity 99.45%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1038.45; Elemental analysis results: Theoretical values: C, 86.69; H, 5.34; B, 1.04; N, 5.39; O, 1.54; Experimental values: C, 86.69; H, 5.33; B, 1.05; N, 5.38; O, 1.55.

[0246] Synthesis Example 34: Synthesis of Compound G580

[0247]

[0248] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 580-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G580 (25% yield, HPLC purity 99.43%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1054.42; Elemental analysis results: Theoretical values: C, 85.37; H, 5.25; B, 1.03; N, 5.31; S, 3.04; Experimental values: C, 85.37; H, 5.24; B, 1.04; N, 5.32; S, 3.03.

[0249] Synthesis Example 35: Synthesis of Compound G594

[0250]

[0251] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 594-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G594 (24% yield, HPLC purity 99.40%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 938.43; Elemental analysis results: Theoretical values: C, 84.42; H, 5.48; B, 1.15; N, 8.95; Experimental values: C, 84.43; H, 5.47; B, 1.15; N, 8.95.

[0252] Synthesis Example 36: Synthesis of Compound G604

[0253]

[0254] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 604-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G604 (25% yield, HPLC purity 99.42%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1044.41; Elemental analysis results: Theoretical values: C, 82.75; H, 5.11; B, 1.03; N, 8.04; S, 3.07; Experimental values: C, 82.76; H, 5.12; B, 1.02; N, 8.03; S, 3.07.

[0255] Synthesis Example 37: Synthesis of Compound G607

[0256]

[0257] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 607-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G607 (25% yield, HPLC purity 99.38%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1092.36; Elemental analysis results: Theoretical values: C, 79.19; H, 4.89; B, 0.99; N, 7.70; Se, 7.23; Experimental values: C, 79.20; H, 4.90; B, 0.98; N, 7.70; Se, 7.22.

[0258] Synthesis Example 38: Synthesis of Compound G613

[0259]

[0260] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 613-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G613 (24% yield, HPLC purity 99.32%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1102.49; Elemental analysis results: Theoretical values: C, 86.01; H, 5.39; B, 0.98; N, 7.62, Experimental values: C, 86.00; H, 5.39; B, 0.99; N, 7.62.

[0261] Synthesis Example 39: Synthesis of Compound G627

[0262]

[0263] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 627-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G627 (26% yield, HPLC purity 99.52%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1048.56; Elemental analysis results: Theoretical values: C, 87.00; H, 6.63; B, 1.03; N, 5.34; Experimental values: C, 87.00; H, 6.64; B, 1.01; N, 5.35.

[0264] Synthesis Example 40: Synthesis of Compound G633

[0265]

[0266] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 633-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G633 (22% yield, HPLC purity 99.36%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1026.45; Elemental analysis results: Theoretical values: C, 86.54; H, 5.40; B, 1.05; N, 5.46; O, 1.55; Experimental values: C, 86.55; H, 5.40; B, 1.05; N, 5.44; O, 1.56.

[0267] Synthesis Example 41: Synthesis of Compound G643

[0268]

[0269] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 643-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G643 (28% yield, HPLC purity 99.45%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 785.39; Elemental analysis results: Theoretical values: C, 87.12; H, 6.16; B, 1.38; N, 5.34; Experimental values: C, 87.10; H, 6.17; B, 1.37; N, 5.36.

[0270] Synthesis Example 42: Synthesis of Compound G666

[0271]

[0272] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 666-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G666 (24% yield, HPLC purity 99.40%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 777.30; Elemental analysis results: Theoretical values: C, 86.48; H, 4.67; B, 1.39; N, 5.40; O, 2.06; Experimental values: C, 86.49; H, 4.67; B, 1.39; N, 5.40; O, 2.05.

[0273] Synthesis Example 43: Synthesis of Compound G676

[0274]

[0275] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 676-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target compound G676 (29% yield, HPLC purity 99.50%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1115.51; Elemental analysis results: Theoretical values: C, 87.16; H, 5.60; B, 0.97; N, 6.27, Experimental values: C, 87.15; H, 5.60; B, 0.98; N, 6.27.

[0276] Synthesis Example 44: Synthesis of Compound G700

[0277]

[0278] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 700-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G700 (24% yield, HPLC purity 99.33%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 972.35; Elemental analysis results: Theoretical values: C, 85.17; H, 4.66; B, 1.11; N, 5.77; S, 3.29; Experimental values: C, 85.18; H, 4.66; B, 1.12; N, 5.76; S, 3.28.

[0279] Synthesis Example 45: Synthesis of Compound G707

[0280]

[0281] Under nitrogen protection, a pentane solution (6.6 mmol) of tert-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 707-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 140 °C for 10 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound G707 (26% yield, HPLC purity 99.61%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1036.56; Elemental analysis results: Theoretical values: C, 86.85; H, 6.71; B, 1.04; N, 5.40, Experimental values: C, 86.86; H, 6.72; B, 1.02; N, 5.40.

[0282] The photophysical properties of the representative fused-ring compounds prepared in the above-described synthetic examples of the present invention are shown in Table 1.

[0283] Table 1:

[0284]

[0285]

[0286] Note: In Table 1, quantum efficiency is the ratio of the average number of photoelectrons generated per unit time to the number of incident photons at a specific wavelength. This is calculated by using compounds with a quantum efficiency of 10... -5 The sample was prepared by dissolving the compound in toluene at a concentration of mol / L, and then measured after deoxygenation under nitrogen. The instrument was an Edinburgh FLS1000 (UK). The half-width at half-maximum (WHM) is the width of the peak at half the peak height of the fluorescence spectrum at room temperature. It is calculated by drawing a straight line parallel to the base of the peak through the midpoint of the peak height, and finding the distance between the two points where this line intersects the peak. The fluorescence spectrum is obtained by measuring the compound at 10 mol / L concentrations. -5 The sample was prepared by dissolving it in toluene at a concentration of mol / L and then tested using a fluorescence spectrometer (Edinburg FLS1000 (UK)).

[0287] As can be seen from Table 1, the fused ring compounds in the embodiments provided by the present invention have high quantum efficiency (≥89%), while the luminescent compounds provided by the present invention exhibit narrow half-width (≤25nm).

[0288] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0289] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0290] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0291] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0292] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0293] The aromatic amine derivatives are compounds shown as HT-1 to HT-34 below. If the material of the hole transport region 3 is an aromatic amine derivative, it can be one or more of the compounds shown as HT-1 to HT-34.

[0294]

[0295]

[0296] The hole injection layer is located between the anode 2 and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-34 mentioned above, or one or more compounds of HI1 to HI3 mentioned below; it can also be one or more compounds of HT-1 to HT-34 doped with one or more compounds of HI1 to HI3 mentioned below.

[0297]

[0298] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0299] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0300] In this invention, the electron transport layer material may be selected from, but is not limited to, one or more combinations of ET-1 to ET-57 listed below.

[0301]

[0302]

[0303]

[0304] The structure of the light-emitting device may also include an electron injection layer located between the electron transport layer and the cathode 8. The electron injection layer material includes, but is not limited to, one or more combinations of the following: Liq, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca.

[0305] The fabrication process of the organic electroluminescent device of the present invention is as follows: an anode, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode are sequentially deposited on a substrate, and then encapsulated. Specifically, the organic light-emitting layer is formed by co-depositing a wide-bandgap material source, an electron donor-type material source, an electron acceptor-type material source, and a resonant TADF material source.

[0306] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0307] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0308] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~9×10 -3 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anolyte film at a deposition rate of 0.1-0.5 nm / s;

[0309] 3. A hole transport layer is vacuum-deposited on top of the hole injection layer at a deposition rate of 0.1-0.5 nm / s.

[0310] 4. The light-emitting layer of the device is vacuum-deposited on the hole transport layer. The light-emitting layer includes the host material and TADF dye. The evaporation rate of the host material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by using a multi-source co-evaporation method to make the dye reach the preset doping ratio.

[0311] 5. The electron transport layer material of the device is vacuum-deposited on top of the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0312] 6. On the electron transport layer, LiF is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer, and Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0313] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0314] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0315] Example 1

[0316] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0317] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0318] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 10 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the electron blocking layer EBL (10 nm) is a host material of the wide bandgap organic light-emitting layer, and the compound G1 of this invention is a dye with a doping concentration of 3 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the hole blocking layer HBL (10 nm) is a ET material, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0319] Example 2

[0320] The preparation method is the same as in Example 1, except that the wide-bandgap host material used in the light-emitting layer is replaced with a TADF-type host TD. The specific device structure is as follows:

[0321] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0322] Example 3

[0323] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G3 instead of G1. The device structure is as follows:

[0324] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0325] Example 4

[0326] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G3 instead of G1. The device structure is as follows:

[0327] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0328] Example 5

[0329] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G21 instead of G1. The device structure is as follows:

[0330] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G21(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0331] Example 6

[0332] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G21 instead of G1. The device structure is as follows:

[0333] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G21(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0334] Example 7

[0335] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G40 instead of G1. The device structure is as follows:

[0336] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G40(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0337] Example 8

[0338] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G40 instead of G1. The device structure is as follows:

[0339] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G40(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0340] Example 9

[0341] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G60 instead of G1. The device structure is as follows:

[0342] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G60(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0343] Example 10

[0344] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G60 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G60 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0345] Example 11

[0346] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G71 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G71 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0347] Example 12

[0348] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G71 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G71 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0349] Example 13

[0350] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G98 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G98 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0351] Example 14

[0352] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G98 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G98 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0353] Example 15

[0354] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G126 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G126 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0355] Example 16

[0356] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G126 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G126 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0357] Example 17

[0358] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G154 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G154 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0359] Example 18

[0360] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G154 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G154 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0361] Example 19

[0362] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G172 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G172 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0363] Example 20

[0364] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G172 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G172 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0365] Example 21

[0366] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G183 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G183 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0367] Example 22

[0368] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G183 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G183 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0369] Example 23

[0370] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G200 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G200 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0371] Example 24

[0372] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G200 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G200 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0373] Example 25

[0374] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G223 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G223 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0375] Example 26

[0376] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G223 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G223 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0377] Example 27

[0378] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G245 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G245 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0379] Example 28

[0380] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G245 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G245 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0381] Example 29

[0382] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G257 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G257 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0383] Example 30

[0384] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G257 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G257 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0385] Example 31

[0386] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G274 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G274 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0387] Example 32

[0388] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G274 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G274 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0389] Example 33

[0390] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G295 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G295 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0391] Example 34

[0392] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G295 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G295 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0393] Example 35

[0394] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G307 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G307 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0395] Example 36

[0396] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G307 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G307 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0397] Example 37

[0398] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G318 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G318 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0399] Example 38

[0400] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G318 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G318 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0401] Example 39

[0402] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G325 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G325 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0403] Example 40

[0404] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G325 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G325 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0405] Example 41

[0406] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G338 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G338 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0407] Example 42

[0408] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G338 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G338 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0409] Example 43

[0410] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G361 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G361 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0411] Example 44

[0412] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G361 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G361 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0413] Example 45

[0414] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G387 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G387 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0415] Example 46

[0416] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G387 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G387 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0417] Example 47

[0418] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G403 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G403 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0419] Example 48

[0420] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G403 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G403 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0421] Example 49

[0422] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G435 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G435 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0423] Example 50

[0424] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G435 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G435 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0425] Example 51

[0426] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G456 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G456 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0427] Example 52

[0428] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G456 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G456 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0429] Example 53

[0430] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G459 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G459 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0431] Example 54

[0432] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G459 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G459 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0433] Example 55

[0434] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G475 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G475 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0435] Example 56

[0436] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G475 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G475 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0437] Example 57

[0438] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G484 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G484 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0439] Example 58

[0440] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G484 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G484 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0441] Example 59

[0442] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G491 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G491 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0443] Example 60

[0444] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G491 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G491 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0445] Example 61

[0446] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G517 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G517 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0447] Example 62

[0448] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G517 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G517 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0449] Example 63

[0450] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G547 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G547 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0451] Example 64

[0452] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G547 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G547 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0453] Example 65

[0454] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G554 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G554 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0455] Example 66

[0456] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G554 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G554 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0457] Example 67

[0458] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G580 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G580 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0459] Example 68

[0460] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G580 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G580 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0461] Example 69

[0462] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G594 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G594 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0463] Example 70

[0464] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G594 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G594 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0465] Example 71

[0466] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G604 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G604 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0467] Example 72

[0468] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G604 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G604 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0469] Example 73

[0470] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G607 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G607 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0471] Example 74

[0472] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G607 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G607 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0473] Example 75

[0474] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G613 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G613 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0475] Example 76

[0476] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G613 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G613 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0477] Example 77

[0478] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G627 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% G627 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0479] Example 78

[0480] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G627 instead of G1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%G627 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0481] Example 79

[0482] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G633 instead of G1. The device structure is as follows:

[0483] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G633(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0484] Example 80

[0485] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G633 instead of G1. The device structure is as follows:

[0486] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G633(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0487] Example 81

[0488] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G643 instead of G1. The device structure is as follows:

[0489] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G643(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0490] Example 82

[0491] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G643 instead of G1. The device structure is as follows:

[0492] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G643(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0493] Example 83

[0494] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G666 instead of G1. The device structure is as follows:

[0495] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G666(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0496] Example 84

[0497] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G666 instead of G1. The device structure is as follows:

[0498] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G666(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0499] Example 85

[0500] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G676 instead of G1. The device structure is as follows:

[0501] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G676(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0502] Example 86

[0503] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G676 instead of G1. The device structure is as follows:

[0504] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G676(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0505] Example 87

[0506] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G700 instead of G1. The device structure is as follows:

[0507] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G700(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0508] Example 88

[0509] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G700 instead of G1. The device structure is as follows:

[0510] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G700(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0511] Example 89

[0512] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with G707 instead of G1. The device structure is as follows:

[0513] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%G707(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0514] Example 90

[0515] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with G707 instead of G1. The device structure is as follows:

[0516] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%G707(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0517] Comparative Device Example 1

[0518] The preparation method is the same as that of device example 1, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C1 in the prior art. The specific device structure is as follows:

[0519] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%C1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0520] Comparative Device Example 2

[0521] The preparation method is the same as that of device embodiment 2, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C1 in the prior art. The specific device structure is as follows:

[0522] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%C1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0523] Comparative Device Example 3

[0524] The preparation method is the same as that of device example 1, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C2 in the prior art. The specific device structure is as follows:

[0525] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%C2(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0526] Comparative Device Example 4

[0527] The preparation method is the same as that of device example 2, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C2 in the prior art. The specific device structure is as follows:

[0528] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%C2(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0529] Comparative Device Example 5

[0530] The preparation method is the same as that of device example 1, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C3 in the prior art. The specific device structure is as follows:

[0531] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%C3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0532] Comparative Device Example 6

[0533] The preparation method is the same as that of device example 2, except that the compound G1 of the present invention used in the light-emitting layer is replaced with compound C3 in the prior art. The specific device structure is as follows:

[0534] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%C3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0535] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0536]

[0537]

[0538] The specific performance data of the organic electroluminescent devices D1 to D80 and devices DD1 to DD6 prepared in the above embodiments are shown in Table 2.

[0539] Table 2:

[0540]

[0541]

[0542]

[0543]

[0544] As can be seen from Table 2 above, when the compounds of the present invention are used as luminescent dyes in the luminescent layer of organic electroluminescent devices, the turn-on voltage is less than 3V, the maximum external quantum efficiency is higher than 25%, and the luminance is 1000 cd / m². 2 At that time, the efficiency roll-off is small, the half-width at half-maximum is less than 30nm, and the LT90 lifetime is greater than 300h.

[0545] The experimental data above show that the general formula compound of this invention, by fused with indolecarbazole on the benzene ring side of the parent nucleus of a BN-type multi-resonance material, achieves a redshift in light color while maintaining the rigid structure of the molecule, and has a large oscillator strength which is beneficial to improving luminescence efficiency. Compared with compound C1 in the prior art, the N atom in the indolecarbazole fragment is located in the para position of the parent nucleus N atom, which more effectively expands the HOMO distribution, resulting in a significant redshift in light color. Compared with compounds C2 and C3 in the prior art, the parent nucleus N atom is individually connected to a polyalkyl-substituted benzene ring, which provides effective steric hindrance and can suppress luminescence quenching, exciton annihilation, and spectral broadening caused by intermolecular stacking, thereby improving device efficiency and lifetime. From the full width at half maximum (FWHM) of the electroluminescence spectrum, it can be seen that the examples confirm an effective multi-resonance effect, which greatly enriches the material system and emission color range of multi-resonance-thermally activated delayed fluorescence, and has good application prospects.

[0546] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

[0547] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. A compound of general formula having the structure shown in formula (I): In formula (Ⅰ), ring A1, ring A2 and ring A3 are each independently selected from any one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings; The substituents in rings A1, A2, and A3 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, and R. 1 Substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, R 1 Substituted or unsubstituted C3-C20 cycloalkyl groups, R 1 Substituted or unsubstituted C1–C20 alkoxy groups, R 1 Substituted or unsubstituted C1-C20 alkylsilyl groups, R 1 Substituted or unsubstituted C1-C20 alkylamino groups, R 1 Substituted or unsubstituted C6–C30 arylamino groups, R 1 Substituted or unsubstituted C3–C30 heteroarylamino groups, R 1 Substituted or unsubstituted C6–C30 aryloxy groups, R 1 Substituted or unsubstituted C3–C30 heteroaryloxy groups, R 1 Substituted or unsubstituted C6-C60 aryl, R 1 One of the C3-C60 heteroaryl groups, substituted or unsubstituted; Furthermore, the substituents in rings A1, A2, and A3 are not connected to each other independently, or two adjacent substituents are connected to each other by chemical bonds to form a ring; the substituents in rings A1, A2, and A3 are not connected to the adjacent ring structure independently, or are connected to the adjacent ring structure by chemical bonds to form a ring. The dashed line between rings A1 and A2 represents a disconnect or a single-key connection; The R 1 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl. R a R b R c R d R e Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, R 2 Substituted or unsubstituted C1-C10 chain alkyl groups, R 2 Substituted or unsubstituted C3-C10 cycloalkyl groups, R 2 Substituted or unsubstituted C1-C10 alkoxy groups, R 2 Substituted or unsubstituted C1-C10 alkylsilyl groups, R 2 Substituted or unsubstituted C1-C10 alkylamino groups, R 2 Substituted or unsubstituted C6–C30 arylamino groups, R 2 Substituted or unsubstituted C3–C30 heteroarylamino groups, R 2 Substituted or unsubstituted C6–C30 aryloxy groups, R 2 Substituted or unsubstituted C3–C30 heteroaryloxy groups, R 2 Substituted or unsubstituted C6-C60 aryl, R 2 One of the substituted or unsubstituted C3-C60 heteroaryl groups; and R a R b R c It can be hydrogen at one time or deuterium at another time; The R a R b R c Each is independent and not connected to the adjacent ring structure; The R 2 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl.

2. The compound of the general formula according to claim 1, characterized in that, It has a structure as shown in general formula (1): Ring A1, Ring A2, Ring A3, R a R b R c R d R e The scope of the definition is the same as that in equation (Ⅰ); Preferably, ring A1, ring A2 and ring A3 are one of substituted or unsubstituted C6-C30 aromatic rings or substituted or unsubstituted C6-C30 heteroaromatic rings; More preferably, at least one of ring A1 and ring A2 is a substituted or unsubstituted C6-C30 six-membered aromatic ring or a substituted or unsubstituted C6-C30 six-membered heteroaromatic ring; More preferably, ring A1 and ring A2 are each independently selected from one of substituted or unsubstituted benzene, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted benzoselenene, and substituted or unsubstituted N-phenylcarbazole; ring A3 is one of substituted or unsubstituted benzene ring and substituted or unsubstituted naphthalene ring. Each of the substituents is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

3. The compound of the general formula according to claim 1 or 2, characterized in that, The ring A3 is any structure shown in formula (a), (b), (c), (d), (e), (f), or (g), and the rings A1 and A2 are each independently any structure shown in formula (a), (b), (c), (d), (e), or (f), wherein any of the dashed double bonds (c1), (c2), (c3), (c4), (c5), (c6), (c7), (c8), (d1), (d2), (d3), (d4), (d5), and (d6) represents the fusion position of the group. Among them, U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 , U 14 , U 15 , U 16 , U 17 , U 18 , U 19 , U 20 , U 21 , U 22 , U 23 , U 24 Each individual chooses their own C, CH or N; The U 1 U 2 U 3 U 4 In the middle, two adjacent pairs are either not connected or connected in a loop, U 5 U 6 U 7 U 8 In the middle, two adjacent pairs are either not connected or connected in a loop, U 9 U 10 Between, U 11 U 12 U 13 U 14 U 15 U 16 U 17 U 18 In the middle, two adjacent pairs are either not connected or connected in a loop, U 19 U 20 U 21 U 22 U 23 U 24 Two adjacent elements in the middle are either not connected or connected in a loop; Z 1 Z 2 Each is independently selected from O, S, Se, NR 21 or CR 22 R 23 ; R 21 R 22 R 23 Each of the following is independently selected from one of the following: unsubstituted or R'-substituted C1-C36 chain alkyl, unsubstituted or R'-substituted C3-C36 cycloalkyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C6-C60 aryloxy, and unsubstituted or R'-substituted C5-C60 heteroaryl; The R 22 With R 23 They are either not connected or connected in a loop; When Z 1 Selected from NR 21 At that time, the R 21 with U 5 The R is either not connected or connected in a loop. 21 with U 9 Disconnected or connected in a loop; when Z 2 Selected from NR 21 At that time, the R 21 with U 7 Do not connect or connect in a loop; R' is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 arylboryl, and C3-C30 heteroaryl. Preferably, ring A3 is a structure shown in any of formula (a), formula (f), or formula (g); ring A1 and ring A2 are each independently a structure shown in any of formula (a), formula (b), formula (c), formula (d), or formula (f), and at least one of ring A1 and ring A2 is a structure shown in any of formula (b), formula (c), or formula (d).

4. The compound of the general formula according to claim 3, characterized in that, The aforementioned formula (g) has the structure shown in the following formula (g1): Preferably, U 20 U 21 U 22 U 23 U 24 Each is independently selected from C or CH.

5. The compound of the general formula according to claim 3, characterized in that, In equations (b), (c), and (d), Z 1 Z 2 Each is independently selected from O, S, and NR. 21 ;R 21 Selected from one of the following groups, either unsubstituted or R'-substituted: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthrimidazoleyl, pyridiniumimidazoleyl, pyraziniumimidazoleyl, quinoxalolineimidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinoxazol 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2, 3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetraazinyl, 1,2,3,4-Tetraazinyl, 1,2,3,5-Tetraazinyl; R' is selected from one of deuterium, cyano, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

6. The compound of the general formula according to claim 3, characterized in that, Stated U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 , U 14 , U 15 , U 16 , U 17 , U 18 , U 19 , U 20 , U 21 , U 22 , U 23 , U 24 Each individual chooses their own C or CH.

7. The compound of the general formula according to claim 3, having a structure as shown in any one of formulas (2) to (15): In equations (2) to (15), R a R b R c R d R e The definition is the same as the definition in equation (Ⅰ); Z 1 U 1 U 2 U 3 U 4 U 5 U 6 U 7 U 8 The definitions of and are the same as those in equations (a) and (b).

8. The compound of the general formula according to any one of claims 1-7, characterized in that, R a 、R b 、R c 、R d 、R e The following groups, independently selected from hydrogen, deuterium, deuterated, or undeuterated groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl Methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indofluorenyl, trimerinyl, isotrimerinyl, spirotriinyl, spiroisotriinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuran Thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, benzoselenophene, isobenzoselenophene, dibenzoselenophene, pyrrole, isoindolyl, carbazole, tert-butyl-substituted carbazole, indole-carbazole, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7, 8-Quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniummidazoleyl, pyraziniummidazoleyl, quinoxaliniummidazoleyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinonexazolyl, phenanthrenexoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, Benzopyrimidinyl, quinoxalinyl, 1,5-diazaphenanthyl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolinyl, phenanthrolinel, 1, 2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridylyl, indazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, (poly)halobenzene, (poly)cyanobenzene or (poly)trifluoromethylbenzene, diphenylamino, tert-butyl-substituted diphenylamino, triphenylamino; Preferably, R a R b R c R e The following groups are independently selected from hydrogen, deuterium, deuterated, or undeuterated groups: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl; and R a R b R c It can be hydrogen at one time or deuterium at another time; R d The following groups are selected from hydrogen, deuterium, deuterated or undeuterated: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl or trifluoromethyl.

9. The compound of the general formula according to claim 3, characterized in that, R 1 R 2 R' is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, biphenyl, terphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzo[a]furanyl, isophenyl benzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indoxocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthrozimidazoleyl, pyridinzimidazoleyl, pyrazinzimidazoleyl, quinoxalinzimidazoleyl, oxazolyl, 1, One or a combination of two of the following: 2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene, (poly)trifluoromethylbenzene.

10. The compound of the general formula according to claim 1, wherein the compound is selected from the following specific structural compounds:

11. The application of the compound according to any one of claims 1-10 as a functional material in an organic electronic device, wherein the organic electronic device is an organic electroluminescent device, an optical sensor, a solar cell, an organic thin-film transistor, or an organic field-effect transistor; Furthermore, the compound is used as a light-emitting layer material in organic electroluminescent devices, specifically as a light-emitting material in the light-emitting layer.

12. An organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; wherein the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is located between the hole transport layer and the electron transport layer, wherein the light-emitting layer contains a compound according to any one of claims 1-10.

13. A display device comprising the organic electroluminescent device of claim 12.

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