A light-emitting material, applications thereof, and an organic electroluminescent device comprising the same

Abstract

The present application relates to an organic compound, having the structure shown in the following formula, belongs to the technical field of organic light-emitting material, the present application also simultaneously relates to the application of the compound in organic electroluminescent device.The present application compound as the light-emitting material in OLED device, shows excellent device performance and stability, can realize the high efficiency, low roll-down, high color purity green light OLED device.The present application simultaneously protects the organic electroluminescent device using the compound of the above 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, ring A3 and ring A4 are each independently selected from any one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings;

[0008] Furthermore, at least one of rings A1, A2, A3, and A4 is a substituted or unsubstituted dibenzo5-membered heterocycle, wherein the heteroatom of the five-membered heterocycle is selected from S, O, Se, or N;

[0009] The substituents described in rings A1, A2, A3, and A4 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, unsubstituted, or R. 1 Substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R 1 Substituted C3–C20 cycloalkyl, unsubstituted or R 1 Substituted C1–C20 alkoxy, unsubstituted or R 1 Substituted C1–C20 alkylsilyl, unsubstituted or R 1 Substituted C1–C20 alkylamino, unsubstituted or R 1 Substituted C6–C30 arylamino groups, unsubstituted or R 1 Substituted C3–C30 heteroarylamino groups, unsubstituted or R1 Substituted C6–C30 aryloxy groups, unsubstituted or R 1 Substituted C3–C30 heteroaryloxy groups, unsubstituted or R 1 Substituted C6–C60 aryl, unsubstituted or R 1 One of the substituted C3-C60 heteroaryl groups;

[0010] Furthermore, the substituents in rings A1, A2, A3, and A4 are each independently unconnected, or two adjacent substituents are connected to form a ring by chemical bonds; the substituents in rings A1, A2, A3, and A4 are each independently unconnected to the adjacent ring structure, or are connected to the adjacent ring structure by chemical bonds to form a ring.

[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] Z1, Z2, Z3, Z4, and Z5 are each independently selected from CR. 2 Or N, the R 2 Each is independently selected from one or a combination of two of the following: hydrogen, deuterium, 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; and adjacent R 2 They are either not connected to each other or are linked together by chemical bonds to form a ring.

[0013] The compounds of the present invention are fused with at least two heteroaromatic rings on the parent nucleus of BN-based multiple resonance materials, and at least one of them is a heterocyclic ring containing S, O or Se in structure. While achieving a red shift in photochromism in the extended conjugated plane, the rigid structure of the molecule is maintained, and it has a large oscillator strength, which is beneficial to improving the luminescence efficiency. In addition, heavy atoms such as S and Se are introduced to enhance the spin-orbit coupling effect, which is beneficial to increasing the reverse intersystem crossing rate of the molecule and thus improving the TADF performance, resulting in highly efficient and low roll-off luminescence. Such a structure is also beneficial to enhancing the horizontal orientation of the molecule and thus improving the light extraction efficiency of the OLED device. When used as a luminescent material in an OLED device, it exhibits excellent device performance and stability, and can achieve a green OLED device with high efficiency, low roll-off and high color purity.

[0014] It should be noted that in this application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between each group and structure, rather than the effect of a single group or structure.

[0015] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0016] In the present invention, the heteroatoms of the heteroaryl group are selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O, S.

[0017] In the present invention, the expression of the ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure where bonding can occur.

[0018] In the present invention, the expression of Ca-Cb represents that the group has a carbon atom number of a-b. Unless otherwise specified, generally, the carbon atom number does not include the carbon atom number of the substituent.

[0019] In this specification, "independently of each other" means that when its subject has multiple ones, they can be the same or different from each other.

[0020] In the present invention, the halogen includes fluorine, chlorine, bromine or iodine.

[0021] In this invention, the C6-C30 (e.g., C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) aromatic rings include monoaromatic rings and fused aromatic rings; the monoaromatic rings include benzene rings, biphenyl rings, or terphenyl rings; the fused aromatic rings refer to rings containing at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused together, exemplarily including but not limited to: naphthalene rings, anthracene rings, phenanthrene rings, indene rings, fluorene rings and their derivatives (9,9-dimethylfluorene ring, benzo[a]fluorene ring, etc.), fluoranthene rings, triphenylene rings, pyrene rings, perylene rings, etc. Cyclic or tetraphenyl rings, etc.

[0022] The C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) heteroaromatic rings include mono-heteroaromatic rings or fused heteroaromatic rings. The mono-heteroaromatic rings include, but are not limited to, pyrrole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, furan rings, thiophene rings, and pyrrole rings. The term "fused heterocyclic aromatic ring" refers to a ring structure containing at least one heterocyclic aromatic ring and one aromatic ring (heterocyclic aromatic ring or aromatic ring), wherein the two rings share two adjacent atoms and are fused together. Examples include, but are not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring and its derivatives (N-phenylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolecarbazole ring, azacarbazole ring, etc.), acridine ring, phenothiazine ring, phenotoxazine ring, hydrogenated acridine ring, etc.

[0023] In this invention, the C1-C20 straight-chain alkyl or branched alkyl group can be, for example, a straight-chain or branched alkyl group of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18; preferably a C1-C16 straight-chain or branched alkyl group; more preferably a C1-C10 straight-chain or branched alkyl group; exemplary examples include, but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, or n-decyl, etc.

[0024] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups described in this invention can be exemplified by the monovalent groups obtained by connecting the above-mentioned straight-chain or branched alkyl groups with O.

[0025] In this invention, the C3-C20 cycloalkyl groups can all be cycloalkyl groups of C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.; exemplary, including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0026] A specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) alkylsilyl group is a monovalent group obtained by substituting at least one hydrogen in -SiH3 with the aforementioned straight-chain or branched alkyl group; a specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) alkylamino group is a monovalent group obtained by substituting at least one hydrogen in -NH2 with the aforementioned straight-chain or branched alkyl group.

[0027] Specific examples of the C2-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) heterocyclic alkyl groups described in this invention can be exemplified by a monovalent group obtained by replacing at least one ring C atom in the above-mentioned cycloalkyl examples with a heteroatom (e.g., O, S, N, or P, etc.), including but not limited to: epoxy group, tetrahydropyrrolyl group, tetrahydrofuranyl group, tetrahydrothiophenyl group, morpholinyl group, piperidinyl group, etc.

[0028] In this invention, the C6-C60 aryl groups can all be aryl groups of 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., preferably C6-C30 aryl groups, including monocyclic aryl groups or fused-ring aryl groups. The monocyclic aryl group refers to a group containing at least one phenyl group. When it contains at least two phenyl groups, the phenyl groups are linked by single bonds. Examples include, but are not limited to, phenyl, biphenyl, and terphenyl groups. The fused-ring aryl group refers to a group containing at least two aromatic rings, where the aromatic rings share two adjacent carbon atoms fused together. Examples include, but are not limited to, naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranyl, triphenylene, pyrene, perylene, etc. Groups such as alkyl or tetraphenyl; the aforementioned groups include all possible ways of connection.

[0029] In this invention, the C3-C60 heteroaryl groups can be heteroaryl groups of 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, preferably C3-C30 heteroaryl groups, and more preferably C4-C20 heteroaryl groups, including monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: furanyl, thiophene, pyrrole, pyridinyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.; the aforementioned groups include all possible linkages.

[0030] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylene groups described in this invention can be exemplified by removing one hydrogen atom from the aforementioned aryl examples to obtain a divalent group; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylene groups can be exemplified by removing one hydrogen atom from the aforementioned heteroarylene examples to obtain a divalent group.

[0031] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy groups described in this invention can be examples of monovalent groups obtained by connecting the above-mentioned aryl groups with O; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryloxy groups can be examples of monovalent groups obtained by connecting the above-mentioned heteroaryl groups with O.

[0032] The C6-C60 (e.g., 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.) arylamino groups, preferably C6-C30 arylamino groups, are monovalent groups formed by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group. Exemplary examples include, but are not limited to, phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc.

[0033] The C3-C60 (e.g., 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.) heteroarylamino groups, preferably C3-C30 heteroarylamino groups, are monovalent groups obtained by substituting at least one hydrogen in -NH2 with the aforementioned heteroaryl group, and exemplary examples include but are not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0034] Furthermore, the compounds of the present invention have a structure as shown in general formula (1):

[0035]

[0036] Rings A1, A2, A3, A4, Z1, Z2, Z3, Z4, and Z5 have the same meaning as expressed in claim 1;

[0037] Preferably, one or two of the rings A1, A2, A3 and A4 are substituted or unsubstituted dibenzo5-membered heterocycles, and the heteroatom of the five-membered heterocycle is selected from S, O, Se or N;

[0038] More preferably, two of the rings A1, A2, A3 and A4 are substituted or unsubstituted dibenzo5-membered heterocycles, and the heteroatom of the five-membered heterocycle is selected from S, Se or N.

[0039] Furthermore, the compounds of the present invention have a structure as shown in any of formulas (1-1) to (1-4):

[0040]

[0041] In equations (1-1) to (1-4), rings A1, A2, A3, A4, Z1, Z2, Z3, Z4, and Z5 have the same meaning as expressed in claim 1;

[0042] Y1-Y 14 Each independently selected from CR 3 Or N, the R 3 Each is independently selected from one or a combination of two of the following: hydrogen, deuterium, 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; and adjacent R 3 They are either not connected to each other or are linked together by chemical bonds to form a ring.

[0043] Furthermore, in the general formula of the compounds of the present invention described above, ring A1, ring A2, ring A3, and ring A4 are each independently selected from one of substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzoselenophene, and substituted or unsubstituted N-phenylcarbazole, and are not simultaneously substituted or unsubstituted N-phenylcarbazole.

[0044] The substituents described in rings A1, A2, A3, and A4 are each independently selected from deuterium, 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, and C3-C60 heteroaryl.

[0045] Furthermore, the compounds of the present invention have structures as shown in any of formulas (2) to (29):

[0046]

[0047]

[0048] In general formulas (2) to (29), X1 and X2 are each independently selected from S, O, Se, or NR. c And X1 and X2 are not both NR. c R c Indicated as C6-C that has been substituted or not substituted. 30 Aryl or C3-C 30 Mixed aromatics;

[0049] Z1, Z2, Z3, Z4, and Z5 have the same meaning as in claim 1; Y1-Y 14 The meaning is the same as that expressed in claim 3;

[0050] When R c When substituents are present, the substituents are independently selected from one or a combination of two of the following: deuterium, 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.

[0051] Preferably, the compounds of the present invention have a structure as shown in any of formulas (2), (3), (4), (5), (8), (9), (14), (15), (20), (21), (26) or (28).

[0052] Furthermore, in the general formula of the compounds of the present invention described above, R 1 R 2 R 3The 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, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl... 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, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoyindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl alkyl, pyrazolyl, indazole, imidazole, benzimidazole, naphthiazole, phenanthiazole, pyridinium-imidazolyl, pyrazinium-imidazolyl, quinoxalinium-imidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphthidyl, azacarbazolyl, benzocarbazolyl , phenanthroline, 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, pteridinyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene or (poly)trifluoromethylbenzene;

[0053] R cSelected from the following groups, whether deuterated or undeuterated: phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, 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 indendrone. Fluorenyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indoxarcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, pyrazinyl, phenazinyl, azacarbazoleyl, phenthiazinylphenanthrolineyl, benzothiadiazolyl, 9,9-dimethylacridyl, (poly)halobenzene, (poly)cyanobenzene, (poly)trifluoromethylbenzene;

[0054] Preferably, R 1 R 2 R 3 The following groups, each independently selected from hydrogen, deuterium, deuterated, or undeuterated groups, are: 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, phenanthrene, benzo[a]phenanthrene. Benzyl, 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, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indenzofluorenyl, furan Benzofuryl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indenecarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthiazoleyl, phenanthroimidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxaloyl Imidazolyl, oxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenthiazinyl, azacarbazolyl, phenanthrolinel, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene, or (poly)trifluoromethylbenzene.

[0055] Furthermore, the general formula compounds of the present invention described in formula (1) can preferably include the following specific structural compounds, which are only representative examples:

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[0106]

[0107]

[0108] This invention also protects the application of any of the compounds shown in general formula (Ⅰ) and formulas (1) to (29) 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.

[0109] The present invention also provides an organic electroluminescent device, including 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 (29).

[0110] 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 (29).

[0111] 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.

[0112] 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:

[0113] (1) The general formula compound of the present invention has at least two heteroaryl rings doped on the core of the BN-type multiple resonance material. Structurally, at least one of these heterocycles is a heterocycle containing S, O, or Se. While expanding the conjugated plane to achieve a redshift in light color, it maintains the rigid structure of the molecule and has a large oscillator strength, which is beneficial to improving luminous efficiency. (2) The general formula compound of the present invention enhances the spin-orbit coupling effect by introducing heavy atoms such as S and Se, which is beneficial to increasing the reverse intersystem crossing rate of the molecule and thus improving TADF performance, achieving efficient and low roll-off luminescence, thereby reducing the power consumption of the device. (3) The general formula compound of the present invention has a high molecular-level orientation, which is beneficial to improving the light extraction efficiency of the OLED device, thereby improving the luminous efficiency of the device. (4) The substituents connected below 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. (5) The general formula compound of the present invention has a narrow half-width of the spectrum and high light 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 displays.

[0114] 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

[0115] 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.

[0116] All the chemical reagents used in this invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, dichloromethane, o-dichlorobenzene, potassium carbonate, 9H-carbazole, cesium carbonate, and reaction intermediates, were purchased from Shanghai Titan Technology Co., Ltd. and Anhui Zesheng Technology Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0117] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0118] Synthesis Example:

[0119] Synthesis of intermediate 1:

[0120]

[0121] 2-Bromo-1,3-difluoro-5-iodobenzene (10.74 g, 33.67 mmol) and phenylboronic acid (4.52 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetraphenylphosphine palladium (1.95 g, 1.68 mmol) and 20 mL of potassium carbonate aqueous solution (9.31 g, 67.34 mmol) were added, and the mixture was heated under reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and subjected to column chromatography (petroleum ether: dichloromethane = 3:1) to give a white solid intermediate 1, weighing 6.8 g, with a yield of 75%.

[0122] Synthesis of intermediate 2-26:

[0123]

[0124] Synthesis of intermediate 2: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-(tert-butyl)phenyl)boronic acid. The resulting intermediate 2 is a white solid with a yield of 72%.

[0125] Synthesis of intermediate 3: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (3,5-di-tert-butylphenyl)boronic acid. The resulting intermediate 3 is a white solid with a yield of 68%.

[0126] Synthesis of intermediate 4: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with [1,1'-biphenyl]-4-ylboronic acid. The resulting intermediate 4 is a white solid with a yield of 72%.

[0127] Synthesis of intermediate 5: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4'-(tert-butyl)-[1,1'-biphenyl]-4-yl)boronic acid. The resulting intermediate 5 is a white solid with a yield of 67%.

[0128] Synthesis of intermediate 6: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (3',5'-di-tert-butyl-[1,1'-biphenyl]-4-yl)boronic acid. The resulting intermediate 6 is a white solid with a yield of 63%.

[0129] Synthesis of intermediate 7: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with ((2R,6r)-2-(3-(tert-butyl)-6-isopropyl-9H-carbazole-9-yl)-6-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl)boronic acid. The resulting intermediate 7 is a white solid with a yield of 56%.

[0130] Synthesis of intermediate 8: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-(3,6-bis(3,5-di-tert-butylphenyl))-9H-carbazole-9-yl)phenyl)boronic acid. The resulting intermediate 8 is a white solid with a yield of 57%.

[0131] Synthesis of intermediate 9: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-benzonitrile)boronic acid. The resulting intermediate 9 is a white solid with a yield of 68%.

[0132] Synthesis of intermediate 10: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (3-benzonitrile)boronic acid. The resulting intermediate 10 is a white solid with a yield of 66%.

[0133] Synthesis of intermediate 11: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (2-benzonitrile)boronic acid. The resulting intermediate 11 is a white solid with a yield of 51%.

[0134] Synthesis of intermediate 12: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (2,4-dicyanophenyl)boronic acid. The resulting intermediate 12 is a white solid with a yield of 55%.

[0135] Synthesis of intermediate 13: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (3,5-dicyanophenyl)boronic acid. The resulting intermediate 13 is a white solid with a yield of 52%.

[0136] Synthesis of intermediate 14: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-(trifluoromethyl)phenyl)boronic acid. The resulting intermediate 14 is a white solid with a yield of 46%.

[0137] Synthesis of intermediate 15: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (3-(trifluoromethyl)phenyl)boronic acid. The resulting intermediate 15 is a white solid with a yield of 58%.

[0138] Synthesis of intermediate 16: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (2-(trifluoromethyl)phenyl)boronic acid. The resulting intermediate 16 is a white solid with a yield of 47%.

[0139] Synthesis of intermediate 17: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with pyridin-4-ylboronic acid. The resulting intermediate 17 is a white solid with a yield of 68%.

[0140] Synthesis of intermediate 18: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with quinoline-4-ylboronic acid. The resulting intermediate 18 is a white solid with a yield of 75%.

[0141] Synthesis of intermediate 19: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4,6-diphenyl-1,3,5-triazinecyclo-2-yl)boronic acid. The resulting intermediate 19 is a white solid with a yield of 71%.

[0142] Synthesis of intermediate 20: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (9-methyl-9H-carbazole-3-yl)boronic acid. The resulting intermediate 20 is a white solid with a yield of 73%.

[0143] Synthesis of intermediate 21: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (9-phenyl-9H-carbazole-3-yl)boronic acid. The resulting intermediate 21 is a white solid with a yield of 56%.

[0144] Synthesis of intermediate 22: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (9-(4-tert-butyl))phenyl)-9H-carbazole-3-yl)boronic acid. The resulting intermediate 22 is a white solid with a yield of 58%.

[0145] Synthesis of intermediate 23: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with dibenzo[b,d]furan-2-ylboronic acid. The resulting intermediate 23 is a white solid with a yield of 59%.

[0146] Synthesis of intermediate 24: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with dibenzo[b,d]thiophene-2-ylboronic acid. The resulting intermediate 24 is a white solid with a yield of 60%.

[0147] Synthesis of intermediate 25: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-(diphenylamino)phenyl)boronic acid. The resulting intermediate 25 is a white solid with a yield of 61%.

[0148] Synthesis of intermediate 26: The synthesis method is similar to that of intermediate 1, except that phenylboronic acid is replaced with (4-(9H-carbazole-9-yl))phenyl)boronic acid. The resulting intermediate 26 is a white solid with a yield of 51%.

[0149] Synthesis Example 1: Synthesis of Compound 1

[0150] 1) Synthesis of intermediate compounds 1-2:

[0151]

[0152] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 1-1 as a white solid.

[0153] Next, in a dry, double-necked round-bottom flask, intermediate 1-1 (3 mmol), 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to give intermediate compound 1-2 as a white solid.

[0154] 2) Synthesis of Compound 1:

[0155]

[0156] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 1-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain target compound 1 (0.57 g, 25% yield, HPLC purity 99.26%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 763.23; Elemental analysis experimental values: C, 84.92; H, 3.97; B, 1.40; N, 5.52; S, 4.18.

[0157] Synthesis Example 2: Synthesis of Compound 2

[0158] 1) Synthesis of intermediate compound 2-2:

[0159]

[0160] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[3,2-a]carbazole (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 = 3:1) to give intermediate compound 2-1 as a white solid.

[0161] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 2-1 (3 mmol), 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to give intermediate compound 2-2 as a white solid.

[0162] 2) Synthesis of Compound 2:

[0163]

[0164] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 2-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain target compound 2 (0.50 g, 22% yield, HPLC purity 99.01%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 763.23; Elemental analysis experimental values: C, 84.92; H, 3.98; B, 1.41; N, 5.51; S, 4.18.

[0165] Synthesis Example 3: Synthesis of Compound 3

[0166] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.33; N, 5.13; S, 3.92.

[0167] Synthesis Example 4: Synthesis of Compound 4

[0168] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.32; N, 5.13; S, 3.91.

[0169] Synthesis Example 5: Synthesis of Compound 5

[0170] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.01; H, 5.29; B, 1.22; N, 4.80; S, 3.66.

[0171] Synthesis Example 6: Synthesis of Compound 6

[0172] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.01; H, 5.29; B, 1.23; N, 4.80; S, 3.66.

[0173] Synthesis Example 7: Synthesis of Compound 7

[0174] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 4. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 839.26; elemental analysis experimental values: C, 85.81; H, 4.07; B, 1.29; N, 5.00; S, 3.82.

[0175] Synthesis Example 8: Synthesis of Compound 8

[0176] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 4. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 839.26; elemental analysis experimental values: C, 85.81; H, 4.08; B, 1.28; N, 5.00; S, 3.82.

[0177] Synthesis Example 9: Synthesis of Compound 9

[0178] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 5. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 895.32; elemental analysis experimental values: C, 85.81; H, 4.72; B, 1.21; N, 4.69; S, 3.58.

[0179] Synthesis Example 10: Synthesis of Compound 10

[0180] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 5. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 895.32; elemental analysis experimental values: C, 85.80; H, 4.72; B, 1.24; N, 4.68; S, 3.58.

[0181] Synthesis Example 11: Synthesis of Compound 11

[0182] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 6. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 951.38; elemental analysis experimental values: C, 85.79; H, 5.29; B, 1.14; N, 4.41; S, 3.37.

[0183] Synthesis Example 12: Synthesis of Compound 12

[0184] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 6. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 951.38; elemental analysis experimental values: C, 85.78; H, 5.29; B, 1.14; N, 4.41; S, 3.37.

[0185] Synthesis Example 13: Synthesis of Compound 13

[0186] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.62; H, 5.72; B, 0.83; N, 5.37; S, 2.46.

[0187] Synthesis Example 14: Synthesis of Compound 14

[0188] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.72; B, 0.82; N, 5.37; S, 2.46.

[0189] Synthesis Example 15: Synthesis of Compound 15

[0190] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0191] Synthesis Example 16: Synthesis of Compound 16

[0192] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0193] Synthesis Example 17: Synthesis of Compound 17

[0194] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.77; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0195] Synthesis Example 18: Synthesis of Compound 18

[0196] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0197] Synthesis Example 19: Synthesis of Compound 19

[0198] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 10. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.37; N, 7.10; S, 4.08.

[0199] Synthesis Example 20: Synthesis of Compound 20

[0200] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 10. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.77; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0201] Synthesis Example 21: Synthesis of Compound 21

[0202] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 11. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0203] Synthesis Example 22: Synthesis of Compound 22

[0204] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 11. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.72; B, 1.37; N, 7.10; S, 4.06.

[0205] Synthesis Example 23: Synthesis of Compound 23

[0206] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 12. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: C, 82.66; H, 3.47; B, 1.32; N, 8.61; S, 3.94.

[0207] Synthesis Example 24: Synthesis of Compound 24

[0208] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 12. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: C, 82.66; H, 3.47; B, 1.33; N, 8.61; S, 3.94.

[0209] Synthesis Example 25: Synthesis of Compound 25

[0210] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 13. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: C, 82.65; H, 3.47; B, 1.33; N, 8.61; S, 3.94.

[0211] Synthesis Example 26: Synthesis of Compound 26

[0212] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 13. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: C, 82.66; H, 3.47; B, 1.33; N, 8.61; S, 3.94.

[0213] Synthesis Example 27: Synthesis of Compound 27

[0214] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.32; F, 6.83; N, 5.05; S, 3.85.

[0215] Synthesis Example 28: Synthesis of Compound 28

[0216] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.84; N, 5.05; S, 3.85.

[0217] Synthesis Example 29: Synthesis of Compound 29

[0218] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 15. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0219] Synthesis Example 30: Synthesis of Compound 30

[0220] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 15. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0221] Synthesis Example 31: Synthesis of Compound 31

[0222] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 16. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.52; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0223] Synthesis Example 32: Synthesis of Compound 32

[0224] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 16. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.31; F, 6.85; N, 5.05; S, 3.85.

[0225] Synthesis Example 33: Synthesis of Compound 33

[0226] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 17. The product is a yellow solid with a yield of 15%. MALDI-TOF-MS results: molecular ion peak: 764.22; elemental analysis experimental values: C, 83.25; H, 3.82; B, 1.41; N, 7.33; S, 4.19.

[0227] Synthesis Example 34: Synthesis of Compound 34

[0228] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 17. The product is a yellow solid with a yield of 28%. MALDI-TOF-MS results: molecular ion peak: 764.22; elemental analysis experimental values: C, 83.24; H, 3.83; B, 1.41; N, 7.33; S, 4.19.

[0229] Synthesis Example 35: Synthesis of Compound 35

[0230] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 18. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 814.24; elemental analysis experimental values: C, 84.03; H, 3.84; B, 1.32; N, 6.88; S, 3.93.

[0231] Synthesis Example 36: Synthesis of Compound 36

[0232] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 18. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 814.24; elemental analysis experimental values: C, 84.01; H, 3.84; B, 1.33; N, 6.88; S, 3.93.

[0233] Synthesis Example 37: Synthesis of Compound 37

[0234] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.17; S, 3.49.

[0235] Synthesis Example 38: Synthesis of Compound 38

[0236] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0237] Synthesis Example 39: Synthesis of Compound 39

[0238] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 20. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 866.27; elemental analysis experimental values: C, 84.52; H, 4.07; B, 1.25; N, 6.46; S, 3.70.

[0239] Synthesis Example 40: Synthesis of Compound 40

[0240] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 20. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 866.27; elemental analysis experimental values: C, 84.51; H, 4.08; B, 1.26; N, 6.46; S, 3.70.

[0241] Synthesis Example 41: Synthesis of Compound 41

[0242] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 21. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: C, 85.34; H, 4.01; B, 1.16; N, 6.03; S, 3.45.

[0243] Synthesis Example 42: Synthesis of Compound 42

[0244] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 21. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: C, 85.34; H, 4.03; B, 1.16; N, 6.03; S, 3.45.

[0245] Synthesis Example 43: Synthesis of Compound 43

[0246] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 22. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 984.35; elemental analysis experimental values: C, 85.34; H, 4.60; B, 1.10; N, 5.69; S, 3.25.

[0247] Synthesis Example 44: Synthesis of Compound 44

[0248] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 22. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 984.35; elemental analysis experimental values: C, 85.35; H, 4.60; B, 1.11; N, 5.69; S, 3.25.

[0249] Synthesis Example 45: Synthesis of Compound 45

[0250] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.42; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0251] Synthesis Example 46: Synthesis of Compound 46

[0252] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.42; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0253] Synthesis Example 47: Synthesis of Compound 47

[0254] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.74; B, 1.24; N, 4.83; S, 7.37.

[0255] Synthesis Example 48: Synthesis of Compound 48

[0256] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.72; B, 1.24; N, 4.83; S, 7.37.

[0257] Synthesis Example 49: Synthesis of Compound 49

[0258] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 25. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 930.30; elemental analysis experimental values: C, 85.15; H, 4.22; B, 1.16; N, 6.02; S, 3.44.

[0259] Synthesis Example 50: Synthesis of Compound 50

[0260] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 25. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 930.30; elemental analysis experimental values: C, 85.15; H, 4.22; B, 1.16; N, 6.02; S, 3.44.

[0261] Synthesis Example 51: Synthesis of Compound 51

[0262] The synthesis method is similar to that of compound 1, except that intermediate 1 is replaced with intermediate 26. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: C, 85.34; H, 4.01; B, 1.16; N, 6.03; S, 3.45.

[0263] Synthesis Example 52: Synthesis of Compound 52

[0264] The synthesis method is similar to that of compound 2, except that intermediate 1 is replaced with intermediate 26. The product is a yellow solid with a yield of 29%. MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: C, 85.34; H, 4.01; B, 1.18; N, 6.03; S, 3.45.

[0265] Synthesis Example 53: Synthesis of Compound 53

[0266] 1) Synthesis of intermediate compound 53-2:

[0267]

[0268] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 53-1 as a white solid.

[0269] Next, in a dry, double-necked round-bottom flask, intermediate 53-1 (3 mmol), 5-(4-tert-butyl)phenyl-5,11-dihydroindolo[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 53-2 as a white solid.

[0270] 2) Synthesis of compound 53:

[0271]

[0272] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 53-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 53 (27% yield, HPLC purity 98.52%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 819.29; Elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.32; N, 5.13; S, 3.92.

[0273] Synthesis Example 54: Synthesis of Compound 55

[0274] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.28; B, 1.23; N, 4.80; S, 3.66.

[0275] Synthesis Example 55: Synthesis of Compound 57

[0276] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 931.41; elemental analysis experimental values: C, 85.05; H, 5.84; B, 1.16; N, 4.52; S, 3.44.

[0277] Synthesis Example 56: Synthesis of Compound 65

[0278] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1359.64; elemental analysis experimental values: C, 85.63; H, 6.07; B, 0.79; N, 5.15; S, 2.36.

[0279] Synthesis Example 57: Synthesis of Compound 67

[0280] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 1360.66; elemental analysis experimental values: C, 86.44; H, 6.29; B, 0.79; N, 4.13; S, 2.35.

[0281] Synthesis Example 58: Synthesis of Compound 69

[0282] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 844.28; elemental analysis experimental values: C, 83.88; H, 4.41; B, 1.27; N, 6.63; S, 3.79.

[0283] Synthesis Example 59: Synthesis of Compound 79

[0284] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 887.28; elemental analysis experimental values: C, 79.82; H, 4.20; B, 1.22; F, 6.42; N, 4.73; S, 3.61.

[0285] Synthesis Example 60: Synthesis of Compound 89

[0286] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 974.34; elemental analysis experimental values: C, 82.54; H, 4.45; B, 1.12; N, 8.62; S, 3.29.

[0287] Synthesis Example 61: Synthesis of Compound 97

[0288] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 909.30; elemental analysis experimental values: C, 84.48; H, 4.43; B, 1.19; N, 4.62; O, 1.76; S, 3.52.

[0289] Synthesis Example 62: Synthesis of Compound 99

[0290] The synthesis method is similar to that of compound 53, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 925.28; elemental analysis experimental values: C, 83.02; H, 4.34; B, 1.17; N, 4.54; S, 6.92.

[0291] Synthesis Example 63: Synthesis of Compound 105

[0292] 1) Synthesis of intermediate compound 105-2:

[0293]

[0294] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 105-1 as a white solid.

[0295] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 105-1 (3 mmol), 11H-benzofurano[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 105-2 as a white solid.

[0296] 2) Synthesis of compound 105:

[0297]

[0298] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 105-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 105 (23% yield, HPLC purity 98.82%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 688.18; Elemental analysis experimental values: C, 83.72; H, 3.66; B, 1.57; N, 4.07; O, 2.32; S, 4.66.

[0299] Synthesis Example 64: Synthesis of Compound 107

[0300] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 744.24; elemental analysis experimental values: C, 83.87; H, 4.47; B, 1.45; N, 3.76; O, 2.15; S, 4.30.

[0301] Synthesis Example 65: Synthesis of Compound 109

[0302] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 800.30; elemental analysis experimental values: C, 83.99; H, 5.17; B, 1.35; N, 3.50; O, 2.00; S, 4.00.

[0303] Synthesis Example 66: Synthesis of Compound 117

[0304] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 1228.53; elemental analysis experimental values: C, 85.00; H, 5.66; B, 0.88; N, 4.56; O, 1.31; S, 2.61.

[0305] Synthesis Example 67: Synthesis of Compound 119

[0306] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 1229.55; elemental analysis experimental values: C, 85.92; H, 5.90; B, 0.88; N, 3.42; O, 1.30; S, 2.61.

[0307] Synthesis Example 68: Synthesis of Compound 121

[0308] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 713.17; elemental analysis experimental values: C, 82.47; H, 3.39; B, 1.51; N, 5.89; O, 2.24; S, 4.49.

[0309] Synthesis Example 69: Synthesis of Compound 131

[0310] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 756.17; elemental analysis experimental values: C, 77.79; H, 3.20; B, 1.42; F, 7.53; N, 3.70; O, 2.11; S, 4.24.

[0311] Synthesis Example 70: Synthesis of Compound 141

[0312] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 843.23; elemental analysis experimental values: C, 81.14; H, 3.58; B, 1.28; N, 8.30; O, 1.90; S, 3.80.

[0313] Synthesis Example 71: Synthesis of Compound 149

[0314] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 778.19; elemental analysis experimental values: C, 83.29; H, 3.50; B, 1.39; N, 3.60; O, 4.11; S, 4.12.

[0315] Synthesis Example 72: Synthesis of Compound 151

[0316] The synthesis method is similar to that of compound 105, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 794.17; elemental analysis experimental values: C, 81.61; H, 3.42; B, 1.36; N, 3.52; O, 2.01; S, 8.07.

[0317] Synthesis Example 73: Synthesis of Compound 157

[0318] 1) Synthesis of intermediate compound 157-2:

[0319]

[0320] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 157-1 as a white solid.

[0321] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 157-1 (3 mmol), 11H-benzo[4,5]thieno[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 157-2 as a white solid.

[0322] 2) Synthesis of compound 157:

[0323]

[0324] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 157-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 157 (22% yield, HPLC purity 97.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 704.16; Elemental analysis experimental values: C, 81.82; H, 3.58; B, 1.53; N, 3.98; S, 9.10.

[0325] Synthesis Example 74: Synthesis of Compound 159

[0326] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 760.22; elemental analysis experimental values: C, 82.10; H, 4.37; B, 1.42; N, 3.68; S, 8.43.

[0327] Synthesis Example 75: Synthesis of Compound 161

[0328] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 16%. MALDI-TOF-MS results: molecular ion peak: 816.28; elemental analysis experimental values: C, 82.34; H, 5.06; B, 1.33; N, 3.43; S, 7.85.

[0329] Synthesis Example 76: Synthesis of Compound 169

[0330] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 1244.51; elemental analysis experimental values: C, 83.90; H, 5.58; B, 0.87; N, 4.50; S, 5.15.

[0331] Synthesis Example 77: Synthesis of Compound 171

[0332] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 1245.53; elemental analysis experimental values: C, 84.81; H, 5.82; B, 0.87; N, 3.37; S, 5.14.

[0333] Synthesis Example 78: Synthesis of Compound 173

[0334] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 729.15; elemental analysis experimental values: C, 80.66; H, 3.32; B, 1.48; N, 5.76; S, 8.79.

[0335] Synthesis Example 79: Synthesis of Compound 183

[0336] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 772.14; elemental analysis experimental values: C, 76.17; H, 3.13; B, 1.41; F, 7.36; N, 3.63; S, 8.30.

[0337] Synthesis Example 80: Synthesis of Compound 193

[0338] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 859.20; elemental analysis experimental values: C, 79.62; H, 3.52; B, 1.26; N, 8.15; S, 7.46.

[0339] Synthesis Example 81: Synthesis of Compound 201

[0340] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 794.17; elemental analysis experimental values: C, 81.61; H, 3.42; B, 1.36; N, 3.52; O, 2.01; S, 8.07.

[0341] Synthesis Example 82: Synthesis of Compound 203

[0342] The synthesis method is similar to that of compound 157, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 810.14; elemental analysis experimental values: C, 79.99; H, 3.36; B, 1.32; N, 3.46; S, 11.86.

[0343] Synthesis Example 83: Synthesis of Compound 209

[0344] The synthesis method is similar to that of compound 157, except that 11H-benzo[4,5]thieno[3,2-b]carbazole is replaced with 11H-benzo[4,5]selenobenzo[3,2-b]carbazole. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 752.10; elemental analysis experimental values: C, 76.71; H, 3.35; B, 1.44; N, 3.73; S, 4.26; Se, 10.51.

[0345] Synthesis Example 84: Synthesis of Compound 211

[0346] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 808.16; elemental analysis experimental values: C, 77.33; H, 4.12; B, 1.34; N, 3.47; S, 3.97; Se, 9.78.

[0347] Synthesis Example 85: Synthesis of Compound 213

[0348] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 20%. MALDI-TOF-MS results: molecular ion peak: 864.22; elemental analysis experimental values: C, 77.87; H, 4.78; B, 1.25; N, 3.24; S, 3.71; Se, 9.14.

[0349] Synthesis Example 86: Synthesis of Compound 221

[0350] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 1292.45; elemental analysis experimental values: C, 80.86; H, 5.38; B, 0.84; N, 4.34; S, 2.48; Se, 6.11.

[0351] Synthesis Example 87: Synthesis of Compound 223

[0352] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 1293.47; elemental analysis experimental values: C, 81.72; H, 5.61; B, 0.86; N, 3.25; S, 2.48; Se, 6.11.

[0353] Synthesis Example 88: Synthesis of Compound 225

[0354] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 777.09; elemental analysis experimental values: C, 75.78; H, 3.12; B, 1.39; N, 5.41; S, 4.13; Se, 10.17.

[0355] Synthesis Example 89: Synthesis of Compound 235

[0356] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 820.09; elemental analysis experimental values: C, 71.81; H, 2.95; B, 1.32; F, 6.95; N, 3.42; S, 3.91; Se, 9.64.

[0357] Synthesis Example 90: Synthesis of Compound 245

[0358] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 907.15; elemental analysis experimental values: C, 75.51; H, 3.35; B, 1.16; N, 7.72; S, 3.54; Se, 8.71.

[0359] Synthesis Example 91: Synthesis of Compound 253

[0360] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 842.11; elemental analysis experimental values: C, 77.06; H, 3.23; B, 1.28; N, 3.33; O, 1.90; S, 3.81; Se, 9.38.

[0361] Synthesis Example 92: Synthesis of Compound 255

[0362] The synthesis method is similar to that of compound 209, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 858.09; elemental analysis experimental values: C, 75.63; H, 3.17; B, 1.26; N, 3.27; S, 7.48; Se, 9.21.

[0363] Synthesis Example 93: Synthesis of Compound 261

[0364] 1) Synthesis of intermediate compound 261-2:

[0365]

[0366] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 261-1 as a white solid.

[0367] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 261-1 (3 mmol), 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 261-2 as a white solid.

[0368] 2) Synthesis of compound 261:

[0369]

[0370] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 261-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 261 (23% yield, HPLC purity 99.21%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 763.23; Elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.40; N, 5.53; S, 4.18.

[0371] Synthesis Example 94: Synthesis of Compound 263

[0372] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.69; B, 1.32; N, 5.13; S, 3.91.

[0373] Synthesis Example 95: Synthesis of Compound 265

[0374] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.29; B, 1.23; N, 4.81; S, 3.66.

[0375] Synthesis Example 96: Synthesis of Compound 273

[0376] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.72; B, 0.83; N, 5.37; S, 2.46.

[0377] Synthesis Example 97: Synthesis of Compound 275

[0378] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0379] Synthesis Example 98: Synthesis of Compound 277

[0380] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.72; B, 1.38; N, 7.10; S, 4.06.

[0381] Synthesis Example 99: Synthesis of Compound 287

[0382] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0383] Synthesis Example 100: Synthesis of Compound 297

[0384] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0385] Synthesis Example 101: Synthesis of Compound 305

[0386] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.28; N, 4.92; O, 1.87; S, 3.75.

[0387] Synthesis Example 102: Synthesis of Compound 307

[0388] The synthesis method is similar to that of compound 261, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.71; B, 1.24; N, 4.83; S, 7.37.

[0389] Synthesis Example 103: Synthesis of Compound 313

[0390] The synthesis method is similar to that of compound 261, except that 12H-benzo[4,5]thieno[2,3-a]carbazole is replaced with 3,6-di-tert-butyl-12H-benzo[4,5]thieno[2,3-a]carbazole. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.28; B, 1.23; N, 4.80; S, 3.66.

[0391] Synthesis Example 104: Synthesis of Compound 315

[0392] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 931.41; elemental analysis experimental values: C, 85.07; H, 5.84; B, 1.16; N, 4.51; S, 3.44.

[0393] Synthesis Example 105: Synthesis of Compound 317

[0394] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 987.48; elemental analysis experimental values: C, 85.08; H, 6.32; B, 1.09; N, 4.25; S, 3.24.

[0395] Synthesis Example 106: Synthesis of Compound 325

[0396] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 1415.70; elemental analysis experimental values: C, 85.63; H, 6.40; B, 0.76; N, 4.94; S, 2.26.

[0397] Synthesis Example 107: Synthesis of Compound 327

[0398] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1416.72; elemental analysis experimental values: C, 86.41; H, 6.61; B, 0.78; N, 3.95; S, 2.26.

[0399] Synthesis Example 108: Synthesis of Compound 329

[0400] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 900.35; elemental analysis experimental values: C, 83.99; H, 5.03; B, 1.20; N, 6.22; S, 3.56.

[0401] Synthesis Example 109: Synthesis of Compound 339

[0402] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 943.34; elemental analysis experimental values: C, 80.16; H, 4.81; B, 1.15; F, 6.02; N, 4.45; S, 3.40.

[0403] Synthesis Example 110: Synthesis of Compound 349

[0404] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1030.40; elemental analysis experimental values: C, 82.72; H, 4.99; B, 1.05; N, 8.15; S, 3.11.

[0405] Synthesis Example 111: Synthesis of Compound 357

[0406] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 965.36; elemental analysis experimental values: C, 84.55; H, 5.01; B, 1.12; N, 4.35; O, 1.66; S, 3.32.

[0407] Synthesis Example 112: Synthesis of Compound 359

[0408] The synthesis method is similar to that of compound 313, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 981.34; elemental analysis experimental values: C, 83.16; H, 4.94; B, 1.10; N, 4.28; S, 6.53.

[0409] Synthesis Example 113: Synthesis of Compound 365

[0410] The synthesis method is similar to that of compound 1, except that 12H-benzo[4,5]thieno[2,3-a]carbazole is replaced with 12H-benzofurano[2,3-a]carbazole. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 747.25; elemental analysis experimental values: C, 86.75; H, 4.04; B, 1.45; N, 5.62; O, 2.14.

[0411] Synthesis Example 114: Synthesis of Compound 367

[0412] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 803.31; elemental analysis experimental values: C, 86.67; H, 4.77; B, 1.34; N, 5.23; O, 1.99.

[0413] Synthesis Example 115: Synthesis of Compound 369

[0414] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 859.37; elemental analysis experimental values: C, 86.60; H, 5.38; B, 1.26; N, 4.89; O, 1.86.

[0415] Synthesis Example 116: Synthesis of Compound 377

[0416] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 1287.60; elemental analysis experimental values: C, 86.69; H, 5.79; B, 0.84; N, 5.44; O, 1.24.

[0417] Synthesis Example 117: Synthesis of Compound 379

[0418] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1288.62; elemental analysis experimental values: C, 87.56; H, 6.02; B, 0.84; N, 4.35; O, 1.24.

[0419] Synthesis Example 118: Synthesis of Compound 381

[0420] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 772.24; elemental analysis experimental values: C, 85.51; H, 3.78; B, 1.40; N, 7.25; O, 2.07.

[0421] Synthesis Example 119: Synthesis of Compound 391

[0422] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 815.24; elemental analysis experimental values: C, 80.99; H, 3.58; B, 1.33; F, 6.99; N, 5.15; O, 1.96.

[0423] Synthesis Example 120: Synthesis of Compound 401

[0424] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 902.30; elemental analysis experimental values: C, 83.81; H, 3.91; B, 1.20; N, 9.31; O, 1.77.

[0425] Synthesis Example 121: Synthesis of Compound 409

[0426] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 837.26; elemental analysis experimental values: C, 86.02; H, 3.86; B, 1.28; N, 5.02; O, 3.82.

[0427] Synthesis Example 122: Synthesis of Compound 411

[0428] The synthesis method is similar to that of compound 365, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0429] Synthesis Example 123: Synthesis of Compound 417

[0430] The synthesis method is similar to that of compound 1, except that 12H-benzo[4,5]thieno[2,3-a]carbazole is replaced with 12H-benzo[4,5]selenobenzo[2,3-a]carbazole. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 811.17; elemental analysis experimental values: C, 80.01; H, 3.73; B, 1.33; N, 5.18; Se, 9.74.

[0431] Synthesis Example 124: Synthesis of Compound 419

[0432] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 867.23; elemental analysis experimental values: C, 80.38; H, 4.42; B, 1.25; N, 4.85; Se, 9.11.

[0433] Synthesis Example 125: Synthesis of Compound 421

[0434] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 923.30; elemental analysis experimental values: C, 80.69; H, 5.02; B, 1.17; N, 4.56; Se, 8.56.

[0435] Synthesis Example 126: Synthesis of Compound 429

[0436] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1351.52; elemental analysis experimental values: C, 82.65; H, 5.52; B, 0.80; N, 5.18; Se, 5.84.

[0437] Synthesis Example 127: Synthesis of Compound 431

[0438] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 1352.54; elemental analysis experimental values: C, 83.48; H, 5.74; B, 0.80; N, 4.14; Se, 5.84.

[0439] Synthesis Example 128: Synthesis of Compound 433

[0440] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 836.17; elemental analysis experimental values: C, 79.05; H, 3.50; B, 1.28; N, 6.70; Se, 9.45.

[0441] Synthesis Example 129: Synthesis of Compound 443

[0442] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 879.16; elemental analysis experimental values: C, 75.18; H, 3.33; B, 1.23; F, 6.49; N, 4.78; Se, 8.99.

[0443] Synthesis Example 130: Synthesis of Compound 453

[0444] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 966.22; elemental analysis experimental values: C, 78.35; H, 3.65; B, 1.12; N, 8.72; Se, 8.18.

[0445] Synthesis Example 131: Synthesis of Compound 461

[0446] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 901.18; elemental analysis experimental values: C, 80.01; H, 3.58; B, 1.20; N, 4.67; O, 1.78; Se, 8.77.

[0447] Synthesis Example 132: Synthesis of Compound 463

[0448] The synthesis method is similar to that of compound 417, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 917.16; elemental analysis experimental values: C, 78.62; H, 3.52; B, 1.18; N, 4.58; S, 3.51; Se, 8.61.

[0449] Synthesis Example 133: Synthesis of Compound 469

[0450] 1) Synthesis of intermediate compound 469-2:

[0451]

[0452] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (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 = 3:1) to give intermediate compound 469-1 as a white solid.

[0453] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 469-1 (3 mmol), 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to give intermediate compound 469-2 as a white solid.

[0454] 2) Synthesis of compound 469:

[0455]

[0456] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 469-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 469 (24% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 763.23; Elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.40; N, 5.52; S, 4.18.

[0457] Synthesis Example 134: Synthesis of Compound 471

[0458] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.32; N, 5.13; S, 3.91.

[0459] Synthesis Example 135: Synthesis of Compound 473

[0460] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.03; H, 5.29; B, 1.23; N, 4.80; S, 3.66.

[0461] Synthesis Example 136: Synthesis of Compound 481

[0462] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.72; B, 0.85; N, 5.35; S, 2.46.

[0463] Synthesis Example 137: Synthesis of Compound 483

[0464] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.96; B, 0.83; N, 4.29; S, 2.46.

[0465] Synthesis Example 138: Synthesis of Compound 485

[0466] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.72; B, 1.37; N, 7.10; S, 4.06.

[0467] Synthesis Example 139: Synthesis of Compound 495

[0468] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.41; H, 3.51; B, 1.30; F, 6.86; N, 5.05; S, 3.85.

[0469] Synthesis Example 140: Synthesis of Compound 505

[0470] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.16; S, 3.49.

[0471] Synthesis Example 141: Synthesis of Compound 513

[0472] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0473] Synthesis Example 142: Synthesis of Compound 515

[0474] The synthesis method is similar to that of compound 469, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.71; B, 1.24; N, 4.83; S, 7.37.

[0475] Synthesis Example 143: Synthesis of Compound 521

[0476] 1) Synthesis of intermediate compound 521-2:

[0477]

[0478] In a 100 mL dry double-necked round-bottom flask, intermediate 521 (3 mmol), 7H-benzo[4,5]thieno[2,3-b]carbazole (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 = 3:1) to obtain intermediate compound 521-1 as a white solid.

[0479] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 521-1 (3 mmol), 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 521-2 as a white solid.

[0480] 2) Synthesis of compound 521:

[0481]

[0482] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 521-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 521 (23% yield, HPLC purity 98.76%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 763.23; Elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.41; N, 5.52; S, 4.18.

[0483] Synthesis Example 144: Synthesis of Compound 523

[0484] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.96; H, 4.67; B, 1.32; N, 5.13; S, 3.91.

[0485] Synthesis Example 145: Synthesis of Compound 525

[0486] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.29; B, 1.23; N, 4.80; S, 3.66.

[0487] Synthesis Example 146: Synthesis of Compound 533

[0488] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 17%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.64; H, 5.72; B, 0.82; N, 5.37; S, 2.46.

[0489] Synthesis Example 147: Synthesis of Compound 535

[0490] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0491] Synthesis Example 148: Synthesis of Compound 537

[0492] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0493] Synthesis Example 149: Synthesis of Compound 547

[0494] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.31; F, 6.86; N, 5.06; S, 3.86.

[0495] Synthesis Example 150: Synthesis of Compound 557

[0496] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0497] Synthesis Example 151: Synthesis of Compound 565

[0498] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0499] Synthesis Example 152: Synthesis of Compound 567

[0500] The synthesis method is similar to that of compound 521, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.86; H, 3.71; B, 1.24; N, 4.82; S, 7.37.

[0501] Synthesis Example 153: Synthesis of Compound 573

[0502] The synthesis method is similar to that of compound 521, except that 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole is replaced with 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.42; N, 5.51; S, 4.18.

[0503] Synthesis Example 154: Synthesis of Compound 575

[0504] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.66; B, 1.32; N, 5.13; S, 3.91.

[0505] Synthesis Example 155: Synthesis of Compound 577

[0506] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.29; B, 1.23; N, 4.80; S, 3.66.

[0507] Synthesis Example 156: Synthesis of Compound 585

[0508] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.72; B, 0.83; N, 5.37; S, 2.45.

[0509] Synthesis Example 157: Synthesis of Compound 587

[0510] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0511] Synthesis Example 158: Synthesis of Compound 589

[0512] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.37; N, 7.10; S, 4.06.

[0513] Synthesis Example 159: Synthesis of Compound 599

[0514] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.42; H, 3.51; B, 1.30; F, 6.85; N, 5.06; S, 3.85.

[0515] Synthesis Example 160: Synthesis of Compound 609

[0516] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.35; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0517] Synthesis Example 161: Synthesis of Compound 617

[0518] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.28; N, 4.92; O, 1.87; S, 3.75.

[0519] Synthesis Example 162: Synthesis of Compound 619

[0520] The synthesis method is similar to that of compound 573, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.87; H, 3.71; B, 1.24; N, 4.83; S, 7.36.

[0521] Synthesis Example 163: Synthesis of Compound 625

[0522] The synthesis method is similar to that of compound 521, except that 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole is replaced with 5-phenyl-4a,5,8,12d-tetrahydroindolo[2,3-c]carbazole. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.41; N, 5.52; S, 4.18.

[0523] Synthesis Example 164: Synthesis of Compound 627

[0524] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.32; N, 5.13; S, 3.91.

[0525] Synthesis Example 165: Synthesis of Compound 629

[0526] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.28; B, 1.23; N, 4.80; S, 3.66.

[0527] Synthesis Example 166: Synthesis of Compound 637

[0528] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.73; B, 0.83; N, 5.37; S, 2.46.

[0529] Synthesis Example 167: Synthesis of Compound 639

[0530] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0531] Synthesis Example 168: Synthesis of Compound 641

[0532] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.38; N, 7.10; S, 4.06.

[0533] Synthesis Example 169: Synthesis of Compound 651

[0534] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0535] Synthesis Example 170: Synthesis of Compound 661

[0536] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.36; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0537] Synthesis Example 171: Synthesis of Compound 669

[0538] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.27; N, 4.93; O, 1.88; S, 3.75.

[0539] Synthesis Example 172: Synthesis of Compound 671

[0540] The synthesis method is similar to that of compound 625, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 16%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.71; B, 1.24; N, 4.83; S, 7.37.

[0541] Synthesis Example 173: Synthesis of Compound 729

[0542] 1) Synthesis of intermediate compound 729-2:

[0543]

[0544] In a 100 mL dry double-necked round-bottom flask, intermediate 1 (3 mmol), 7H-benzo[4,5]thieno[2,3-b]carbazole (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 = 3:1) to give intermediate compound 729-1 as a white solid.

[0545] Next, in a 100 mL dry double-necked round-bottom flask, intermediate 729-1 (3 mmol), 11H-benzo[4,5]thieno[3,2-b]carbazole (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, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound 729-2 as a white solid.

[0546] 2) Synthesis of compound 729:

[0547]

[0548] A pentane solution of tert-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of intermediate compound 729-2 (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 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 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 = 15:1) to obtain the target compound 729 (22% yield, HPLC purity 99.36%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 704.16; Elemental analysis experimental values: C, 81.82; H, 3.58; B, 1.53; N, 3.98; S, 9.12.

[0549] Synthesis Example 174: Synthesis of Compound 731

[0550] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 760.22; elemental analysis experimental values: C, 82.10; H, 4.37; B, 1.42; N, 3.68; S, 8.43.

[0551] Synthesis Example 175: Synthesis of Compound 733

[0552] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 816.28; elemental analysis experimental values: C, 82.33; H, 5.06; B, 1.32; N, 3.42; S, 7.85.

[0553] Synthesis Example 176: Synthesis of Compound 741

[0554] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 20%. MALDI-TOF-MS results: molecular ion peak: 1244.51; elemental analysis experimental values: C, 83.90; H, 5.58; B, 0.86; N, 4.50; S, 5.15.

[0555] Synthesis Example 177: Synthesis of Compound 743

[0556] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1245.53; elemental analysis experimental values: C, 84.80; H, 5.82; B, 0.87; N, 3.37; S, 5.14.

[0557] Synthesis Example 178: Synthesis of Compound 745

[0558] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 729.15; elemental analysis experimental values: C, 80.66; H, 3.33; B, 1.48; N, 5.76; S, 8.79.

[0559] Synthesis Example 179: Synthesis of Compound 755

[0560] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 772.14; elemental analysis experimental values: C, 76.17; H, 3.13; B, 1.40; F, 7.38; N, 3.65; S, 8.30.

[0561] Synthesis Example 180: Synthesis of Compound 765

[0562] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 859.20; elemental analysis experimental values: C, 79.61; H, 3.51; B, 1.26; N, 8.15; S, 7.46.

[0563] Synthesis Example 181: Synthesis of Compound 773

[0564] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 794.17; elemental analysis experimental values: C, 81.61; H, 3.42; B, 1.36; N, 3.52; O, 2.01; S, 8.07.

[0565] Synthesis Example 182: Synthesis of Compound 775

[0566] The synthesis method is similar to that of compound 729, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 810.14; elemental analysis experimental values: C, 79.98; H, 3.36; B, 1.35; N, 3.46; S, 11.86.

[0567] Synthesis Example 183: Synthesis of Compound 781

[0568] The synthesis method is similar to that of compound 521, except that 7H-benzo[4,5]thieno[2,3-b]carbazole is replaced with 8H-benzo[4,5]thieno[2,3-c]carbazole. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: C, 84.93; H, 3.98; B, 1.41; N, 5.52; S, 4.18.

[0569] Synthesis Example 184: Synthesis of Compound 783

[0570] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.96; H, 4.67; B, 1.32; N, 5.13; S, 3.91.

[0571] Synthesis Example 185: Synthesis of Compound 785

[0572] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.02; H, 5.29; B, 1.23; N, 4.81; S, 3.66.

[0573] Synthesis Example 186: Synthesis of Compound 793

[0574] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.73; B, 0.83; N, 5.37; S, 2.46.

[0575] Synthesis Example 187: Synthesis of Compound 795

[0576] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 23%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.83; N, 4.29; S, 2.46.

[0577] Synthesis Example 188: Synthesis of Compound 797

[0578] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 27%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.72; B, 1.37; N, 7.10; S, 4.06.

[0579] Synthesis Example 189: Synthesis of Compound 807

[0580] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.31; F, 6.85; N, 5.05; S, 3.85.

[0581] Synthesis Example 190: Synthesis of Compound 817

[0582] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.36; H, 3.84; B, 1.18; N, 9.15; S, 3.49.

[0583] Synthesis Example 191: Synthesis of Compound 825

[0584] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.28; N, 4.93; O, 1.87; S, 3.75.

[0585] Synthesis Example 192: Synthesis of Compound 827

[0586] The synthesis method is similar to that of compound 781, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 18%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.86; H, 3.71; B, 1.24; N, 4.83; S, 7.38.

[0587] Synthesis Example 193: Synthesis of Compound 833

[0588] The synthesis method is similar to that of compound 781, except that 5-phenyl-5,11-dihydroindolo[3,2-b]carbazole is replaced with 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: C, 84.93; H, 3.99; B, 1.42; N, 5.51; S, 4.18.

[0589] Synthesis Example 194: Synthesis of Compound 835

[0590] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 2. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: C, 84.97; H, 4.67; B, 1.31; N, 5.13; S, 3.91.

[0591] Synthesis Example 195: Synthesis of Compound 837

[0592] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 3. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: C, 85.01; H, 5.29; B, 1.23; N, 4.80; S, 3.66.

[0593] Synthesis Example 196: Synthesis of Compound 845

[0594] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 7. The product is a yellow solid with a yield of 22%. MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: C, 85.63; H, 5.72; B, 0.83; N, 5.37; S, 2.46.

[0595] Synthesis Example 197: Synthesis of Compound 847

[0596] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 8. The product is a yellow solid with a yield of 21%. MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: C, 86.48; H, 5.95; B, 0.82; N, 4.29; S, 2.46.

[0597] Synthesis Example 198: Synthesis of Compound 849

[0598] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 9. The product is a yellow solid with a yield of 26%. MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: C, 83.76; H, 3.71; B, 1.38; N, 7.10; S, 4.06.

[0599] Synthesis Example 199: Synthesis of Compound 859

[0600] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 14. The product is a yellow solid with a yield of 24%. MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: C, 79.43; H, 3.51; B, 1.30; F, 6.85; N, 5.05; S, 3.85.

[0601] Synthesis Example 200: Synthesis of Compound 869

[0602] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 19. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: C, 82.36; H, 3.86; B, 1.17; N, 9.15; S, 3.49.

[0603] Synthesis Example 201: Synthesis of Compound 877

[0604] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 23. The product is a yellow solid with a yield of 25%. MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: C, 84.41; H, 3.78; B, 1.27; N, 4.92; O, 1.87; S, 3.75.

[0605] Synthesis Example 202: Synthesis of Compound 879

[0606] The synthesis method is similar to that of compound 833, except that intermediate 1 is replaced with intermediate 24. The product is a yellow solid with a yield of 19%. MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: C, 82.85; H, 3.71; B, 1.24; N, 4.83; S, 7.37.

[0607] 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.

[0608] 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.

[0609] 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).

[0610] 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).

[0611] 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.

[0612] 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.

[0613]

[0614]

[0615] 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.

[0616]

[0617] 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.

[0618] 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).

[0619] 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.

[0620]

[0621]

[0622]

[0623] The structure of the light-emitting device may also include an electron injection layer located between the electron transport layer and the cathode 6. 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.

[0624] The fabrication process of the organic electroluminescent device is described as follows: An anode 2, a hole transport layer 3, an organic light-emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, followed by encapsulation. Specifically, the organic light-emitting layer 4 is formed by co-deposition using a wide-bandgap material source, an electron donor-type material source, an electron acceptor-type material source, and a resonant TADF material source.

[0625] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0626] 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.

[0627] 2. Place the glass plate with the anode in a vacuum chamber and evacuate it to 1×10-5~9×10-3 Pa. Vacuum deposit a hole injection layer on the anode film at a deposition rate of 0.1-0.5 nm / s.

[0628] 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.

[0629] 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.

[0630] 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;

[0631] 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.

[0632] 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.

[0633] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0634] Example 1

[0635] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0636] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0637] 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, where compound 1 of this invention is a dye with a doping concentration of 3 wt%, and 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 hole blocking layer; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are selected from LiF (0.5 nm) and aluminum (150 nm).

[0638] Example 2

[0639] 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:

[0640] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0641] Example 3

[0642] The preparation method is the same as in Example 1, except that dye 1 is replaced with dye 2 in the light-emitting layer. The device structure is as follows:

[0643] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%2(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0644] Example 4

[0645] The preparation method is the same as in Example 2, except that dye 1 is replaced with dye 2 in the light-emitting layer. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%2 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0646] Example 5

[0647] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 3 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host:3wt%3 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0648] Example 6

[0649] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 3 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%3 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0650] Example 7

[0651] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 4 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host:3wt%4 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0652] Example 8

[0653] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 4 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%4 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0654] Example 9

[0655] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 5 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host:3wt%5 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0656] Example 10

[0657] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 5 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%5 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0658] Example 11

[0659] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 6 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt%6 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0660] Example 12

[0661] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 6 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%6 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0662] Example 13

[0663] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 7 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt%7 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0664] Example 14

[0665] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 7 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%7 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0666] Example 15

[0667] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 8 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 8 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0668] Example 16

[0669] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 8 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%8 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0670] Example 17

[0671] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with dye 9 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt%9 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0672] Example 18

[0673] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with dye 9 instead of dye 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%9 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0674] Example 19

[0675] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 10 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 10 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0676] Example 20

[0677] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 10 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%10 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0678] Example 21

[0679] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 11 instead of 11. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 11 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0680] Example 22

[0681] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with I1 instead of 11. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%11 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0682] Example 23

[0683] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 12 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 12 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0684] Example 24

[0685] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 12 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%12 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0686] Example 25

[0687] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 13 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 13 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0688] Example 26

[0689] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 13 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 13 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0690] Example 27

[0691] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 14 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 14 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0692] Example 28

[0693] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 14 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%14 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0694] Example 29

[0695] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 15 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 15 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0696] Example 30

[0697] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 15 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%15 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0698] Example 31

[0699] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 16 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 16 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0700] Example 32

[0701] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 16 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%16 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0702] Example 33

[0703] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 17 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 17 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0704] Example 34

[0705] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 17 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%17 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0706] Example 35

[0707] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 18 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 18 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0708] Example 36

[0709] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 18 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%18 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0710] Example 37

[0711] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 19 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 19 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0712] Example 38

[0713] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 19 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%19 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0714] Example 39

[0715] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 20 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 20 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0716] Example 40

[0717] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 20 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%20 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0718] Example 41

[0719] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 21 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 21 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0720] Example 42

[0721] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 21 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%21 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0722] Example 43

[0723] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 22 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 22 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0724] Example 44

[0725] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 22 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%22 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0726] Example 45

[0727] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 23 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 23 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0728] Example 46

[0729] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 23 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%23 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0730] Example 47

[0731] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 24 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 24 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0732] Example 48

[0733] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 24 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%24 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0734] Example 49

[0735] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 25 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 25 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0736] Example 50

[0737] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 25 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%25 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0738] Example 51

[0739] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 26 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 26 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0740] Example 52

[0741] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 26 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%26 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0742] Example 53

[0743] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 27 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 27 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0744] Example 54

[0745] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 27 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%27 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0746] Example 55

[0747] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 28 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 28 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0748] Example 56

[0749] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 28 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%28 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0750] Example 57

[0751] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 29 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 29 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0752] Example 58

[0753] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 29 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%29 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0754] Example 59

[0755] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 30 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 30 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0756] Example 60

[0757] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 30 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%30 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0758] Example 61

[0759] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 31 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 31 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0760] Example 62

[0761] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 31 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%31 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0762] Example 63

[0763] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 32 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 32 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0764] Example 64

[0765] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 32 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%32 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0766] Example 65

[0767] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 33 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 33 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0768] Example 66

[0769] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 33 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%33 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0770] Example 67

[0771] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 34 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 34 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0772] Example 68

[0773] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 34 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%34 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0774] Example 69

[0775] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 35 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 35 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0776] Example 70

[0777] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 35 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%35 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0778] Example 71

[0779] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 36 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 36 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0780] Example 72

[0781] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 36 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%36 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0782] Example 73

[0783] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 37 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 37 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0784] Example 74

[0785] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 37 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%37 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0786] Example 75

[0787] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 38 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 38 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0788] Example 76

[0789] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 38 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%38 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0790] Example 77

[0791] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 39 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 39 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0792] Example 78

[0793] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 39 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%39 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0794] Example 79

[0795] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 40 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 40 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0796] Example 80

[0797] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 40 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%40 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0798] Example 81

[0799] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 41 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 41 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0800] Example 82

[0801] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 41 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%41 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0802] Example 83

[0803] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 42 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 42 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0804] Example 84

[0805] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 42 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%42 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0806] Example 85

[0807] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 43 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 43 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0808] Example 86

[0809] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 43 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 43 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0810] Example 87

[0811] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 44 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 44 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0812] Example 88

[0813] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 44 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%44 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0814] Example 89

[0815] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 45 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 45 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0816] Example 90

[0817] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 45 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%45 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0818] Example 91

[0819] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 46 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 46 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0820] Example 92

[0821] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 46 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%46 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0822] Example 93

[0823] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 47 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 47 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0824] Example 94

[0825] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 47 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%47 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0826] Example 95

[0827] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 48 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 48 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0828] Example 96

[0829] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 48 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%48 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0830] Example 97

[0831] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 49 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 49 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0832] Example 98

[0833] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 49 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%49 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0834] Example 99

[0835] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 50 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 50 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0836] Example 100

[0837] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 50 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%50 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0838] Example 101

[0839] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 51 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 51 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0840] Example 102

[0841] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 51 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%51 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0842] Example 103

[0843] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 52 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 52 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0844] Example 104

[0845] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 52 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%52 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0846] Example 105

[0847] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 105. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 105 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0848] Example 106

[0849] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 105. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 105 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0850] Example 107

[0851] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 109. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 109 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0852] Example 108

[0853] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 109 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 109 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0854] Example 109

[0855] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 117 instead of 117. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 117 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0856] Example 110

[0857] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 117 instead of 117. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 117 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0858] Example 111

[0859] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 121 instead of 11. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 121 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0860] Example 112

[0861] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 121 instead of 11. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 121 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0862] Example 113

[0863] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 141. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 141 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0864] Example 114

[0865] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 141. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 141 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0866] Example 115

[0867] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 151. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 151 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0868] Example 116

[0869] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 151. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 151 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0870] Example 117

[0871] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 157 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 157 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0872] Example 118

[0873] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 157 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 157 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0874] Example 119

[0875] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 161. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 161 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0876] Example 120

[0877] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 161. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 161 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0878] Example 121

[0879] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 169. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 169 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0880] Example 122

[0881] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 169. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 169 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0882] Example 123

[0883] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 173. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 173 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0884] Example 124

[0885] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 173. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 173 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0886] Example 125

[0887] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 193. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 193 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0888] Example 126

[0889] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 193. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 193 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0890] Example 127

[0891] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 203 instead of I. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 203 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0892] Example 128

[0893] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 203 instead of I. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 203 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0894] Example 129

[0895] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 209 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 209 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0896] Example 130

[0897] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 209 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%209 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0898] Example 131

[0899] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 213 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 213 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0900] Example 132

[0901] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 213 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 213 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0902] Example 133

[0903] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 221 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 221 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0904] Example 134

[0905] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 221 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%221 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0906] Example 135

[0907] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 225 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 225 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0908] Example 136

[0909] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 225 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 225 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0910] Example 137

[0911] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 245 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 245 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0912] Example 138

[0913] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 245 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 245 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0914] Example 139

[0915] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 255 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 255 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0916] Example 140

[0917] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 255 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%255 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0918] Example 141

[0919] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 261 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 261 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0920] Example 142

[0921] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 261 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%261 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0922] Example 143

[0923] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 265 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 265 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0924] Example 144

[0925] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 265 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 265 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0926] Example 145

[0927] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 273 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 273 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0928] Example 146

[0929] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 273 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 273 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0930] Example 147

[0931] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 277 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 277 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0932] Example 148

[0933] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 277 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%277 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0934] Example 149

[0935] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 297 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 297 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0936] Example 150

[0937] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 297 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%297 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0938] Example 151

[0939] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 307 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 307 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0940] Example 152

[0941] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 307 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%307 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0942] Example 153

[0943] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 417 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 417 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0944] Example 154

[0945] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 417 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 417 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0946] Example 155

[0947] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 421 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 421 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0948] Example 156

[0949] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 421 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 421 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0950] Example 157

[0951] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 429 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 429 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0952] Example 158

[0953] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 429 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 429 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0954] Example 159

[0955] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 433 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 433 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0956] Example 160

[0957] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 433 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 433 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0958] Example 161

[0959] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 453 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 453 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0960] Example 162

[0961] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 453 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 453 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0962] Example 163

[0963] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 463 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 463 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0964] Example 164

[0965] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 463 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 463 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0966] Example 165

[0967] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 469 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 469 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0968] Example 166

[0969] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 469 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 469 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0970] Example 167

[0971] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 473 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 473 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0972] Example 168

[0973] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 473 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 473 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0974] Example 169

[0975] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 481 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 481 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0976] Example 170

[0977] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 481 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 481 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0978] Example 171

[0979] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 485 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 485 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0980] Example 172

[0981] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 485 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 485 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0982] Example 173

[0983] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 505 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 505 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0984] Example 174

[0985] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 505 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 505 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0986] Example 175

[0987] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 515 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 515 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0988] Example 176

[0989] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 515 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 515 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0990] Example 177

[0991] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 521 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 521 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0992] Example 178

[0993] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 521 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%521 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0994] Example 179

[0995] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 525 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 525 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0996] Example 180

[0997] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 525 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 525 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0998] Example 181

[0999] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 533. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 533 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1000] Example 182

[1001] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 533 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 533 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1002] Example 183

[1003] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 537 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 537 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1004] Example 184

[1005] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 537 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 537 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1006] Example 185

[1007] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 557 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 557 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1008] Example 186

[1009] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 557 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 557 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1010] Example 187

[1011] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 567 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 567 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1012] Example 188

[1013] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 567 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 567 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1014] Example 189

[1015] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 729 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 729 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1016] Example 190

[1017] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 729 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 729 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1018] Example 191

[1019] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 733. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 733 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1020] Example 192

[1021] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 733 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 733 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1022] Example 193

[1023] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 741 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 741 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1024] Example 194

[1025] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 741 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 741 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1026] Example 195

[1027] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 745 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 745 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1028] Example 196

[1029] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 745 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 745 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1030] Example 197

[1031] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 765 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 765 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1032] Example 198

[1033] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 765 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 765 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1034] Example 199

[1035] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 775 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 775 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1036] Example 200

[1037] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 775 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 775 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1038] Example 201

[1039] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 781 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 781 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1040] Example 202

[1041] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 781 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%781 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1042] Example 203

[1043] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 785 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 785 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1044] Example 204

[1045] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 785 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 785 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1046] Example 205

[1047] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 793 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 793 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1048] Example 206

[1049] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 793 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 793 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1050] Example 207

[1051] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 797 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 797 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1052] Example 208

[1053] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 797 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 797 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1054] Example 209

[1055] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 817 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 817 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1056] Example 210

[1057] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 817 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 817 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1058] Example 211

[1059] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 827 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 827 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1060] Example 212

[1061] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 827 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 827 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1062] Example 213

[1063] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 833. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 833 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1064] Example 214

[1065] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 833 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt%833 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1066] Example 215

[1067] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 837 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 837 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1068] Example 216

[1069] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 837 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 837 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1070] Example 217

[1071] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 845 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 845 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1072] Example 218

[1073] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 845 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 845 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1074] Example 219

[1075] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 849 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 849 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1076] Example 220

[1077] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 849 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / TD:3wt% 849 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1078] Example 221

[1079] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 869 instead of 1. The device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / Host: 3wt% 869 (30nm) / HBL (10nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[1080] Example 222

[1081] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 869 instead of 1. The device structure is as follows:

[1082] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%869(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1083] Example 223

[1084] The preparation method is the same as in Example 1, except that the dye used in the light-emitting layer is replaced with 879 instead of 1. The device structure is as follows:

[1085] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%879(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1086] Example 224

[1087] The preparation method is the same as in Example 2, except that the dye used in the light-emitting layer is replaced with 879 instead of 1. The device structure is as follows:

[1088] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%879(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1089] Comparative Device Example 1

[1090] The preparation method is the same as that of device embodiment 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P1 in the prior art. The specific device structure is as follows:

[1091] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%P1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1092] Comparative Device Example 2

[1093] The preparation method is the same as that of device embodiment 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P1 in the prior art. The specific device structure is as follows:

[1094] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%P1(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1095] Comparative Device Example 3

[1096] The preparation method is the same as that of device embodiment 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P2 in the prior art. The specific device structure is as follows:

[1097] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%P2(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1098] Comparative Device Example 4

[1099] The preparation method is the same as that of device embodiment 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P2 in the prior art. The specific device structure is as follows:

[1100] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%P2(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1101] Comparative Device Example 5

[1102] The preparation method is the same as that of device embodiment 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P3 in the prior art. The specific device structure is as follows:

[1103] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%P3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1104] Comparative Device Example 6

[1105] The preparation method is the same as that of device embodiment 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced with compound P3 in the prior art. The specific device structure is as follows:

[1106] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:3wt%P3(30nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[1107] The structural formulas of the various organic materials used in the above embodiments are as follows:

[1108]

[1109]

[1110] The specific performance data of the organic electroluminescent devices D1 to D224 and devices DD1 to DD6 prepared in the above embodiments are shown in Table 1.

[1111] Table 1:

[1112]

[1113]

[1114]

[1115]

[1116]

[1117]

[1118] As can be seen from Table 1 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. 2At 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.

[1119] Comparative Examples 1 and 2 have only one fused carbazole group, while the other carbazole group has two benzene rings attached. This reduces structural rigidity and intensifies nonradiative transitions caused by vibration and rotation, resulting in decreased device efficiency and a significant increase in the full width at half maximum (FWHM). Comparative Examples 3 and 4 also have only one fused carbazole group and lack the introduction of sulfur atoms, leading to slower reverse intersystem crossing processes and reduced exciton dynamics. This results in a more severe efficiency roll-off and decreased device lifetime. Furthermore, the lack of sufficiently large steric hindrance groups to suppress luminescence quenching, exciton annihilation, and spectral broadening caused by intermolecular stacking leads to poor device performance. Comparative Examples 5 and 6 also lack steric hindrance groups, resulting in a highly planar molecular structure and severe intermolecular stacking, leading to luminescence quenching, exciton annihilation, and spectral broadening. Additionally, one donor in their molecular structure is a fused aromatic ring derived from diphenylamine, which has relatively weak structural rigidity, thus reducing device efficiency and increasing the FWHM.

[1120] The experimental data above show that the general formula compound of this invention, by doping at least two heteroaromatic rings onto the core of a BN-type multiple resonance material, with at least one of these rings being a heterocycle containing S, O, or Se, achieves a redshift in light color while maintaining the rigid structure of the molecule. The larger oscillator strength is beneficial for improving luminescence efficiency. Furthermore, the introduction of S and Se heavy atoms to enhance the spin-orbit coupling effect helps to increase the reverse intersystem crossing rate of MR-TADF, resulting in a smaller efficiency roll-off at high brightness. The full width at half maximum (FWHM) of the electroluminescence spectrum confirms the effective multiple resonance effect in the examples, thereby greatly enriching the material system and emission color range of multiple resonance-thermally activated delayed fluorescence, showing promising application prospects.

[1121] 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.

[1122] 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 a general formula having a structure as shown in any of formulas (2) to (25): in, X1 and X2 are each independently selected from S, O, Se, or NR. c And X1 and X2 are not both NR. c R c Indicated as substituted or unsubstituted C6-C 30 Aryl; when R c When substituents are present, the substituents are each independently selected from C1-C20 straight-chain or branched alkyl groups; Y1-Y 14 Each independently selected from CR 3 The R 3 Each is independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl; Z1, Z2, Z3, Z4, and Z5 are each independently selected from CR. 2 Or N, the R 2 Each is independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkylamino, C6-C30 arylamino, C6-C60 aryl, or C3-C60 heteroaryl; and two adjacent Rs are selected from... 2 They are either not connected to each other or are linked together by chemical bonds to form a ring.

2. The compound of general formula according to claim 1, having a structure as shown in any one of formulas (2), (3), (4), (5), (8), (9), (14), (15), (20), (21): 。 3. The compound of the general formula according to any one of claims 1-2, characterized in that, R c Selected from the following groups: phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, 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.

4. The compound of the general formula according to any one of claims 1-2, characterized in that, R 2 R 3 Each group is independently selected from hydrogen or the following 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, 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-indenofluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiophene, benzene Thiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoyl, indocarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthimidazoleyl, phenanthimidazoleyl, pyridiniumimidazoyl, pyraziniumimidazoyl, quinoxoliniumimidazoyl, oxazolyl, 1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxolinyl, pyrazinyl, phenazinyl, phenthiazinyl, azacarbazoyl, phenanthrololinyl, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, halobenzene, cyanobenzene, or trifluoromethylbenzene.

5. The compound of the general formula according to claim 1, wherein the compound is selected from the following specific structural compounds: 。 6. The application of the general formula compound according to any one of claims 1-5, wherein the application is as a functional material in an organic electronic device, said organic electronic device being selected from organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; The compound of the general formula is used as a light-emitting layer material in organic electroluminescent devices.

7. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, characterized in that, The light-emitting functional layer includes at least one compound as described in any one of claims 1-5.

8. The organic electroluminescent device according to claim 7, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region, wherein... The light-emitting layer contains any one of the compounds described in claims 1-5.

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